u/throwaway256897q6r72

It took me ten years to work up to a position at my job that I finally felt like I was making enough money to survive. After a decade working in operations, I moved over to the sales team, specifically outside sales. I missed staying in one spot and working with the guys I worked so long with, but it was kind of fun traveling around to different customers and helping them out.

I can't say too much about what I do, except that my company isn't that big. Big enough that we make millions of dollars a year and able to provide our employees with benefits. But small enough that, even as a worker in operations, I knew the entire upper management team and could go have a conversation with any of them and not feel like I was a bother.

The outside sales team had eight people on it, but only two of them worked in the same area I was brought on to help with. They were both only a few years away from retirement, and needed somebody to potentially take over for them. I had known both of them since I started at the company, so going out on the road with them was easy, with no awkwardness at all.

My main boss was named Amy, who was a vice president in the company. She was on the road daily, keeping up relations with customers and always on the lookout for new ones. And, since we were a middleman who sold specific products from one company to the next, we were always talking to companies that we might want to buy from, to offer their product for sale, something I quickly found out that Amy excelled at. Watching her sell our company to another, trying to convince them to use us to sell their product was magic and I knew that I had a lot to learn from her.

While I spent the first few months working for outside sales out on the road, traveling some days with Amy and other days with the other team member, a guy named Robert, I was still home every night, something that made my wife and four kids happy. When I accepted the job with them, I was warned that a few times a year, I would have to travel outside the state, visiting different plants that made the products we sold, and promoting relations with them.

The first time I had to travel somewhere, I woke up around three in the morning, planning on being at the airport around 4:30. After silencing my alarm, I went to the bathroom, took an incredibly quick shower, and then brushed my teeth. As I brushed, I looked at myself in the mirror. I had recently trimmed my brown hair down a bit, but it was still a little shaggy. My beard was cut close to my face, framing my jaw. After cleaning out my toothbrush, I put in my contacts, blinking my blue eyes a few times to get them into focus. When my deodorant was on, I tossed it, my toothbrush and paste, and contact case and solution into a bag, and put that into a suitcase packed for a couple days of travel.

I was still getting used to a newer dress code, having to change nearly my entire wardrobe with the new position. Gone were the days of wearing basketball shorts or dirty jeans and a ripped shirt or old hoodie. Now it was clean jeans or slacks and polo shirts. I grabbed a quick breakfast to eat on the go before kissing my wife goodbye and getting in my car to drive to the airport.

At the airport, I met Amy after I got through security. She gave me a quick hug, already full of energy, and almost instantly started going over the itinerary for our quick trip.

As she talked, I couldn't help but stare at her. She was in her late fifties or early sixties, and just beautiful. Long black hair, an amazing smile, and a killer petite body that I knew she used to her advantage when she felt the need to. An extra button undone on an already low cut blouse. Slacks or jeans that were too tight. It was fun to watch guys casting glances her way, especially as we got up from our seats in the terminal to grab a snack and drink for the trip.

When we sat back down at the gate, Amy answered her phone and I overheard her say, "Yeah, Ryan's here with me at the gate. Should be boarding soon. Yes, he's pretty prepared for it. I'm excited as well. I'll check in later."

As she hung up, she was shaking her head and I jokingly said, "Vice President of the company and still having to check in with others?"

Amy laughed and said, "It was Robert. He hates me traveling alone, so he's glad you're coming along. We're always checking in with each other."

The plane ride from Utah to Washington only took a couple of hours and we spent the time getting to know each other a little better. It was fun to hear about her experience as a working mom, raising three children, while working sixty hours a week and her husband was always gone, working as a contractor. I made an offhand joke about a lot of lonely nights and she threw me off guard when she said, "I didn't have a whole ton of those, even with him gone."

"The kids do seem to fill those nights, don't they?" I commented back.

"I wasn't talking about kids," Amy responded in a deadpan tone and I honestly couldn't tell if she was joking or not.

When we landed in Washington, the company we were touring that day had a car waiting for us. It drove us over to our hotel, letting us check in and drop off our bags before driving us to the plant, where we were greeted by a few of the main executives of the company.

During our tour, I mainly took a step back, watching as Amy took charge, asking all the right questions, not revealing too much, and really making a good impression on everybody she met. And, just like at the airport, I caught more than one guy doing a double check when she walked past.

After the tour of the plant, we all went to a nearby restaurant for lunch. Amy and I sat next to each other. On more than one occasion, she touched my arm, as she explained more about what I did for the company, my background, and what I would be doing in the future.

Every time she touched my arm, I felt a shiver go up it and the few times we made eye contact with each other, I felt like she held the gaze a little longer than usual. But, I could have been imagining things.

It was just us in the company car on the drive back to the plant after lunch, plus the driver behind a closed window. We were talking about our impressions of the company and people we were meeting with when Amy said, "So, what do you think about Sam, their VP of Sales? Did you see the eyes he was making at me? How bad do you think he wants to fuck me?"

She said it so nonchalantly that it caught me totally off guard and I wasn't sure how to respond, stammering out something about me not noticing.

"Relax," she said with a laugh. "I know how most of these guys see me. I know what they want. I've even given in a few times. Like I said on the plane, I don't have a lot of lonely nights and if it helps the company, even better."

When I didn't respond right away, Amy smiled and said, "But don't worry. He won't be coming back to my room tonight. Hopefully somebody else will be."

I could have sworn she was batting her eyes at me as she talked. Was she always like this? Was I reading too much into it? I had no idea but I did know that I was going to have trouble getting out of the car without somebody seeing something.

For the rest of the afternoon, we were stuck in a conference room, listening to PowerPoint presentations from three different people, explaining more about the company, the product, and what they thought they could offer us.

At one point, Amy stepped out of the conference room to take a phone call and Sam, the executive she thought was checking her out, turned to me and said, "Man, it must be great traveling with her."

"Yes, it is. I'm learning a lot from her," I responded, keeping it professional although the look on his face told me he wasn't.

He laughed a little before asking, "I bet she gets noticed a lot."

I simply shrugged my shoulders, acting like I hadn't thought about it.

As the day wrapped up, Amy and I said our goodbyes to everybody we had been meeting with, promised to stay in touch, and were driven back to our hotel. When we arrived, Amy said, "I'm going up to my room to freshen up before dinner. I'll call an Uber and meet you down here in, let's say, twenty minutes?"

I told her that sounded good to me as we entered the elevator, rode it up to our floor, and walked over to our rooms that were right next to each other. I called my wife and talked to her and the kids for a few more minutes, as I wondered just what Amy was doing to freshen up. When I heard her door open, I told them I loved them, and went to join her, riding in the elevator with her down to the lobby.

I didn't notice any changes right away but did think that maybe her blouse had an extra button undone. She still had her black hair down and was wearing the same blouse and tight slacks. She looked a little shorter, so I wondered if she switched out the heels she had been wearing for a smaller pair.

The first part of dinner was mainly Amy picking my brain about what I thought about our tour and how I thought both companies could benefit and help each other. She listened to everything I had to say, gave me her thoughts without making me feel like an idiot, and seemed to be pretty happy with what I had to say.

Just before our food came, Amy changed the subject, claiming she was tired of work talk. As we talked more about our families and our hobbies, I noticed a definite change, as she leaned forward more, her hand reaching out to touch mine, and her knees bumping and resting against mine under the table.

Halfway through dinner, as I said something about my wife, Amy asked, "So, any worries from your wife about your traveling alone? I'm guessing that after almost fifteen years of marriage, she probably trusts you completely?"

I laughed a little and said, "Yes, she does. She knows I'd much rather be in my hotel room, probably playing a game or watching a movie, than I would be out chasing somebody."

"What if you didn't have to go out chasing?" Amy asked, catching me off guard. I took a big gulp of air, as I saw the serious look on her face and was unsure how to respond. Amy smiled as she caught a passing waiter's eye and said, "Can I get the check, please?"

Our drive back to the hotel was quiet, but I noticed Amy sitting a little closer, her legs a little more open than before. We thanked the driver as we were dropped off and I saw him looking at Amy's ass as she started to walk away and part of me wondered if I was about to see more of it. And I wouldn't complain or be upset if the answer was yes.

Inside the lobby, before pressing the button for the elevator, Amy turned to face me and said, "Ryan...whatever happens tonight stays here."

When I didn't respond, instead just staring into her eyes, as she took a step towards me and placed her hand on my arm, she said, "If you're thinking of coming into my room, don't overthink it. Just enjoy it."

The elevator ride was quiet, although my mind was racing. What would happen if I followed her? What if I didn't? Was this a one-time only thing? Or would she expect it whenever we traveled together? What if it was a test? Would word spread? And then, as I was still trying to make up my mind, I glanced down at her and saw a brief glimpse of what looked like a lacy black bra. And I knew I wanted to see more.

In her room, I was still a little nervous. Unsure what to do. Amy had a smile on her face as she set her phone down and walked up to me. "Relax," she whispered as she slowly wrapped her arms around me, stepped up onto her tiptoes, and kissed me.

Her lips were softer than I expected, but there was nothing uncertain about her intentions or what she wanted. She didn't rush it, didn't need to. Every movement was deliberate and controlled, just gentle and patient, like we'd kissed a hundred times and we knew just what we were doing and what the other wanted.

I placed my hands on her hips and was surprised at how small and delicate she felt. Not fragile in any way, but like a treasure I wanted to take care of. As we continued to kiss, Amy unwrapped her arms from my neck and moved them down to my waist. She pulled me closer to her and I could feel the warmth coming from her body, plus a faint hint of perfume I hadn't smelled before.

I felt Amy move, her foot taking a step towards the bed. I hesitated and Amy slowly ended the kiss, and looked into my eyes. I saw a different look in them than I had seen before. I immediately leaned back into her and kissed her lips. As the kiss deepened, neither one of us wanting to end it, Amy's hands moved around to my groin, and started to undo the belt holding up my slacks.

We started to move together, heading towards the bed. Her hands continued to work towards getting my pants off, pushing them down towards my knees where I helped to kick them off. I knew that my cock was hard and pushing against my boxers, and moaned into her mouth when her hand briefly brushed against it.

I moved my hands up and started to undo the belt around her slacks. As I pulled it out of the belt loops, Amy finally rested her hand on my cock, through my boxers, but didn't move it. I hooked my fingers into her slacks, feeling how tight they were, and started to move them down her body. I pulled my lips away from hers, my forehead resting against her forehead, as I looked down, watching as she let go of my cock and helped pull her slacks off.

We finally reached the bed, still kissing, nearly bumping into a few objects along the way, and I felt Amy gently pushing me to sit down. She immediately climbed onto my lap, straddling my legs with hers, and giving me a brief view of her black panties before we resumed kissing.

My breath caught as we kissed and I tried to convince myself that this was really happening. I had Amy, one of the vice presidents of the company I worked for, half naked on my lap, and rubbing her groin against my hard cock. I moved my hands around to her butt and grabbed her cheeks, squeezing them as she rolled her hips and pressed down on my groin, causing Amy to lightly moan into my mouth.

Amy briefly ended the kiss as she pulled my shirt off and ran her hands down my chest, her fingers going through the hair on it. When she reached our groins, she grabbed onto my arms and brought them around to her front. "I want these somewhere else," she said before resuming the kiss.

She lifted my hands up to her chest and placed them on her breasts. The fabric of her blouse was soft under my hands and I could just feel the outline of her bra, as well as the warmth coming from her body. The shape of her breasts pressed into my hands as I lightly squeezed them.

She was softer than I expected, full but with a natural weight to her that shifted slightly as my hands settled. Not firm in the way that I'd be used to, but something else...warmer, more real.

I moved my hands over as I squeezed a few more times, letting my fingertips rub through her blouse, going right above where her bra rested. When I reached the center of her breasts, where she already had the top few buttons undone, she ended the kiss, but continued to move her groin. I looked down and watched as I used my fingers to undo the rest of the buttons.

As her fabric shifted, revealing more of her chest and black lace bra, my movements slowed, without me really thinking about it. The black lace framed her perfectly, pulling my attention in to a sight I'd wanted to see for years.

She wasn't posed or trying to be as she sat on my lap, watching me like she knew exactly what I was seeing and what I felt as I saw it. When my fingers reached the buttons closer to her stomach, I leaned my head down and started to kiss her chest and her cleavage. Amy helped me to pull her blouse off, leaving her in just her bra and panties on my lap.

"Oh, Ryan," she moaned softly, still rolling her hips.

I looked up into her eyes before kissing her lips again. She had her arms hanging loosely at her sides as I reached around and went to unclasp her bra. Amy slid it down her arms, letting it fall between us, and I immediately put my hands on her bare breasts, cupping and squeezing them as we made out.

I was a little surprised at how firm they felt, how quickly her nipples hardened against my palm, and I loved how Amy responded as I touched them. She moaned into my mouth, scooting closer to me, and pressing down more with her groin.

Ending the kiss, I moved my mouth down, going over her neck, to her chest, and ending on her breasts, kissing all over the tops of them. I used my fingers to rub her nipples, making her moan my name again.

Amy brought her hands up and placed her hands on the back of my head, gently pulling me into her breast, as I stuck out my tongue and licked around it. With her encouragement, I wrapped my lips around her nipple and sucked it into my mouth, while I continued to rub her other nipple with my fingers.

I moved back and forth between her breasts, sucking and licking on each nipple as I listened to her moan. Her hip movements never slowed and I could feel my cock aching for it.

Amy must have felt it too as she softly said, "You know, we can always come back to those later."

I understood what she meant as I moved my hand between us and slipped it into her panties, feeling the wetness through her neatly trimmed hair before finding her vagina. I rubbed her slit and lips for a few moments before she said, "Ryan..."

She placed her hands on my shoulders and leaned her body into me as our lips met again. I started to lean backwards as I wrapped my arms around her waist and we were laying on the bed within seconds, still kissing, as we awkwardly moved up to the top of the bed.

When we were there, Amy ended the kiss as she sat up on me and scooted back a bit, just enough that she could hook her fingers into the hem of my boxers and started to pull them down.

I felt like I couldn't breathe as I waited for her reaction. She didn't rush her reaction, if she had one at all. She looked at my face first, smiled slightly as she saw me watching her, then dropped her gaze down to my groin. I had been undressed plenty of times before and wasn't scared or nervous of what I had. But, to be truthful, I'd never been with a woman of Amy's maturity, and didn't want to let her down.

She smiled a little wider as she finished taking my boxers off, and wrapped her hand around my shaft. Her fingers were tiny, matching her petite body, but she knew just what she was doing as she slowly stroked my cock. I moaned a little causing Amy to look up at me and smile.

As I watched her, she used her free hand to move her hair behind her ear and out of her face, before she leaned down, going right over my cock. She lightly blew on it before opening her mouth, sticking out her tongue, and swirling it around my tip.

Amy slowly wrapped her lips around my cock and started to move her mouth up and down my shaft, timing it with her hand. Amy was in no hurry, being in total control, knowing just what to do to maximize the pleasure.

Just like I felt when we kissed, her lips were incredibly soft. She was making every second count as she went up and down. This wasn't a blowjob intended to get me off. It was just a precursor to something more.

"Amy," I softly moaned, matching the same tone she had a few minutes ago.

Amy seemed to know what I meant as she took me out of her mouth and sat back up. I watched as she took off her panties, sliding them down her legs, and then moving back up to line up my cock with her pussy.

I placed my hands on her hips as Amy easily and expertly guided the tip of my cock into her entrance, let go of my shaft, and moved her body down. She moaned softly, closing her eyes, as my cock filled her.

After taking a moment to let us get used to each other, Amy opened her eyes as she started to roll her hips, sliding my cock in and out of her. My mind went blank, enjoying the feeling, the pleasure, of her riding me.

"Oh my God," Amy moaned as she placed her hands close to my stomach, using me to help support her as she went up and down my cock.

I moved my hands off her hips, going around to her butt, where I cupped and squeezed her cheeks, holding on as she rode my cock. Her hands started to slip and she leaned down onto my body, pressing her breasts against me as she kissed my lips.

As we made out, Amy continued to move her hips, sliding her pussy up and down my cock. I kept my hands on her ass, squeezing her cheeks as I pushed up with my hips. Ending the kiss, Amy rested her head next to mine, and moaned into my ear as she slowed her body down.

I took over, using my hands on her ass to move her body, in addition to pushing up with my hips, and burying my cock into her pussy. "Oh my God. Ryan. Don't hold back," she moaned softly.

I moved my hands up and wrapped my arms around her waist as I bent my knees and planted my feet on the bed. Knowing what I was doing, Amy wrapped her arms around my neck and moaned as I flipped us around, keeping my cock inside her, and laying her flat on her back.

We kissed a little more as she spread her legs and arms out. As the kiss ended, I pushed myself above her, placing my hands on the bed, and started to move back and forth. I matched her pace from when she was riding me, going slow and steady. I made sure she got my full length every time, enjoying the feeling of her pussy.

"Hmm...yes. That's just what I needed," Amy moaned, closing her eyes and also enjoying the feeling. She lifted her legs a little and placed her hands down by my butt, as I went in and out of her.

As I looked down at her, seeing the pleasure on her face, her body reacting to mine, her breasts moving with my thrusts, I could feel my orgasm building up.

"Amy...," I moaned out, unable to stop moving.

"Yes, Ryan, yes," she moaned, her fingers digging into my back and holding me in place.

I started to orgasm, my moans joining hers as I continued to move as my cock pumped cum inside the sixty-year-old beauty. I briefly closed my eyes, losing myself in the moment, loving the moment as I climaxed.

I kept moving for as long as I could, wanting to enjoy the feeling of finishing inside her as long as possible. As I finished and could feel my cock starting to go limp, I rolled off Amy and finally thought about what had just happened. Who it was. Why and how it happened. What the consequences might be.

Amy reached over to the bedside table and grabbed a tissue, using it to wipe her groin before throwing the tissue away and rolling onto her side, placing her arm across my chest, and snuggling up against me.

As she rested against me, I wrapped my arm around her, holding her close. She let out a soft moan before saying, "We have an early morning tomorrow. Should probably get to sleep."

"Yeah, we should," I answered but neither of us moved.

She hesitated for a second before saying, "If you wanted to get your belongings from your room, you could stay the night here and who knows what could happen when we wake up."

That got me moving as I finally got up from the bed. I put on just enough clothes to exit her room and step next door to mine. As I left, Amy was still naked on her bed, telling me to hurry back.

I quickly changed into my pajamas in my room before making sure I had everything I had before going back to Amy's room. When I walked back in, I saw that Amy had pulled her black hair back into a ponytail and had put back on her black panties, along with a tight black, spaghetti-string tank top, with a lace trim along the top and bottom.

She laughed as I looked her body up and down, my eyes briefly lingering on her breasts and groin. "Come on, Ryan, let's get to sleep. This old lady needs some rest after that."

We crawled into the bed, covering ourselves with the blanket, before giving each other a small kiss and falling asleep.

When we started to wake up the next morning, Amy had her back to me, and my morning wood was pressing against her ass. I had one arm around her body. "Hmmm...," Amy moaned as she slowly woke up, and wiggled her ass against my cock. "I love waking up to that feeling."

I laughed a little as I moved my hand from her stomach. I went up to her chest and cupped her breast, squeezing it slowly, as I leaned down and started to kiss the back of her neck. She continued to moan, slowly moving her ass, as I slipped my hand inside her tank top, and used my fingers to pinch and rub her nipples.

With my free hand, I slipped it inside her panties, and made a comment about her already being wet.

"I had so many dreams about what you did to me last night. And waking up with you this hard? I'm soaked," she said, opening her legs a little for me to more easily rub her pussy.

"There was one problem with last night," I said as I slowly inserted my finger into her pussy and moved it in and out. When she asked what it was, I told her, "Getting you off."

"Keep doing what you're doing and it'll happen fast," she moaned, closing her eyes and pressing back against me as I kept rubbing her nipples and fingering her pussy.

In and out I went, listening to her wetness squish around my finger, and feeling the inside of her pussy as it clenched around my finger. I moved my other hand between her breasts, taking her nipples between my fingers and rubbing them.

Just as when I touched her nipples the night before, I was surprised with how they felt between my fingers. Softer around the edges but with a firm center that responded immediately to my touch. I alternated between her breasts and couldn't help but wonder how many deals she had sealed by someone seeing her nipples or touching them like I was.

"Oh yes. Right there, Ryan," Amy moaned as I pushed my finger deeper into her, continuing to slide it in and out. She pressed back against me harder, nearly burying my cock into her ass. I felt the tip of my cock slip out of the flap in my boxers, the hardness of it too much to contain and moaned a little as the fabric of her panties rubbed against it.

Amy's breathing started to get sharper and she started to move her body a little more as I kept fingering her. She moved her hand down to her groin, placing it on top of mine and holding my hand there. She moved it up and down a bit, getting my palm to rub her slit as she whispered that she was getting close.

Amy brought her other hand up above her head, reaching for my head. It rested on my cheek as I felt her entire body stiffen, then relax as she let out a deep breath and climaxed.

As she orgasmed, Amy closed her legs around my hand, pinning me to her, with my finger buried deep inside her. I had stopped kissing her neck, but went back to kissing it as she arched her body. I was a little surprised by how quiet her moans were but also knew that she wasn't trying to show off and just wanted to enjoy the experience.

When her orgasm started to subside, she twisted her head around and pulled my lips over to hers, giving me a passionate kiss.

As she pulled her lips away from me, she let out another deep breath and said, "That felt good."

"I'm glad," I told her, keeping my hand on her breast, but just holding it, and removing my hand from her panties as I continued to plant little kisses along her neck.

Amy moaned slightly as I started to move my hips, sliding my cock around her ass. "I want you again...but we do need to start moving. Come take a shower with me. We're not done yet."

A few minutes later, we were standing in the bathroom, the shower going, and stripping off our pajamas. In the shower, Amy briefly used her lips on me again before standing up, and finishing me off with her hand, letting my cum wash away in the water as it poured down around us.

After the shower, we dressed, both of us casting glances towards the other as we covered up, gathered up our belongings, and met an Uber at the door to the hotel. The car ride to the airport was quiet as I lost myself in my thoughts, and Amy answered emails on her phone. During the short flight home, Amy did remark that she would have to see what other mills we could visit, and soon, and I caught a look in her eyes, telling me more than she said out loud.

It took me ten years to work up to a position at my job that I finally felt like I was making enough money to survive. After a decade working in operations, I moved over to the sales team, specifically outside sales. I missed staying in one spot and working with the guys I worked so long with, but it was kind of fun traveling around to different customers and helping them out.

I can't say too much about what I do, except that my company isn't that big. Big enough that we make millions of dollars a year and able to provide our employees with benefits. But small enough that, even as a worker in operations, I knew the entire upper management team and could go have a conversation with any of them and not feel like I was a bother.

The outside sales team had eight people on it, but only two of them worked in the same area I was brought on to help with. They were both only a few years away from retirement, and needed somebody to potentially take over for them. I had known both of them since I started at the company, so going out on the road with them was easy, with no awkwardness at all.

My main boss was named Amy, who was a vice president in the company. She was on the road daily, keeping up relations with customers and always on the lookout for new ones. And, since we were a middleman who sold specific products from one company to the next, we were always talking to companies that we might want to buy from, to offer their product for sale, something I quickly found out that Amy excelled at. Watching her sell our company to another, trying to convince them to use us to sell their product was magic and I knew that I had a lot to learn from her.

While I spent the first few months working for outside sales out on the road, traveling some days with Amy and other days with the other team member, a guy named Robert, I was still home every night, something that made my wife and four kids happy. When I accepted the job with them, I was warned that a few times a year, I would have to travel outside the state, visiting different plants that made the products we sold, and promoting relations with them.

The first time I had to travel somewhere, I woke up around three in the morning, planning on being at the airport around 4:30. After silencing my alarm, I went to the bathroom, took an incredibly quick shower, and then brushed my teeth. As I brushed, I looked at myself in the mirror. I had recently trimmed my brown hair down a bit, but it was still a little shaggy. My beard was cut close to my face, framing my jaw. After cleaning out my toothbrush, I put in my contacts, blinking my blue eyes a few times to get them into focus. When my deodorant was on, I tossed it, my toothbrush and paste, and contact case and solution into a bag, and put that into a suitcase packed for a couple days of travel.

I was still getting used to a newer dress code, having to change nearly my entire wardrobe with the new position. Gone were the days of wearing basketball shorts or dirty jeans and a ripped shirt or old hoodie. Now it was clean jeans or slacks and polo shirts. I grabbed a quick breakfast to eat on the go before kissing my wife goodbye and getting in my car to drive to the airport.

At the airport, I met Amy after I got through security. She gave me a quick hug, already full of energy, and almost instantly started going over the itinerary for our quick trip.

As she talked, I couldn't help but stare at her. She was in her late fifties or early sixties, and just beautiful. Long black hair, an amazing smile, and a killer petite body that I knew she used to her advantage when she felt the need to. An extra button undone on an already low cut blouse. Slacks or jeans that were too tight. It was fun to watch guys casting glances her way, especially as we got up from our seats in the terminal to grab a snack and drink for the trip.

When we sat back down at the gate, Amy answered her phone and I overheard her say, "Yeah, Ryan's here with me at the gate. Should be boarding soon. Yes, he's pretty prepared for it. I'm excited as well. I'll check in later."

As she hung up, she was shaking her head and I jokingly said, "Vice President of the company and still having to check in with others?"

Amy laughed and said, "It was Robert. He hates me traveling alone, so he's glad you're coming along. We're always checking in with each other."

The plane ride from Utah to Washington only took a couple of hours and we spent the time getting to know each other a little better. It was fun to hear about her experience as a working mom, raising three children, while working sixty hours a week and her husband was always gone, working as a contractor. I made an offhand joke about a lot of lonely nights and she threw me off guard when she said, "I didn't have a whole ton of those, even with him gone."

"The kids do seem to fill those nights, don't they?" I commented back.

"I wasn't talking about kids," Amy responded in a deadpan tone and I honestly couldn't tell if she was joking or not.

When we landed in Washington, the company we were touring that day had a car waiting for us. It drove us over to our hotel, letting us check in and drop off our bags before driving us to the plant, where we were greeted by a few of the main executives of the company.

During our tour, I mainly took a step back, watching as Amy took charge, asking all the right questions, not revealing too much, and really making a good impression on everybody she met. And, just like at the airport, I caught more than one guy doing a double check when she walked past.

After the tour of the plant, we all went to a nearby restaurant for lunch. Amy and I sat next to each other. On more than one occasion, she touched my arm, as she explained more about what I did for the company, my background, and what I would be doing in the future.

Every time she touched my arm, I felt a shiver go up it and the few times we made eye contact with each other, I felt like she held the gaze a little longer than usual. But, I could have been imagining things.

It was just us in the company car on the drive back to the plant after lunch, plus the driver behind a closed window. We were talking about our impressions of the company and people we were meeting with when Amy said, "So, what do you think about Sam, their VP of Sales? Did you see the eyes he was making at me? How bad do you think he wants to fuck me?"

She said it so nonchalantly that it caught me totally off guard and I wasn't sure how to respond, stammering out something about me not noticing.

"Relax," she said with a laugh. "I know how most of these guys see me. I know what they want. I've even given in a few times. Like I said on the plane, I don't have a lot of lonely nights and if it helps the company, even better."

When I didn't respond right away, Amy smiled and said, "But don't worry. He won't be coming back to my room tonight. Hopefully somebody else will be."

I could have sworn she was batting her eyes at me as she talked. Was she always like this? Was I reading too much into it? I had no idea but I did know that I was going to have trouble getting out of the car without somebody seeing something.

For the rest of the afternoon, we were stuck in a conference room, listening to PowerPoint presentations from three different people, explaining more about the company, the product, and what they thought they could offer us.

At one point, Amy stepped out of the conference room to take a phone call and Sam, the executive she thought was checking her out, turned to me and said, "Man, it must be great traveling with her."

"Yes, it is. I'm learning a lot from her," I responded, keeping it professional although the look on his face told me he wasn't.

He laughed a little before asking, "I bet she gets noticed a lot."

I simply shrugged my shoulders, acting like I hadn't thought about it.

As the day wrapped up, Amy and I said our goodbyes to everybody we had been meeting with, promised to stay in touch, and were driven back to our hotel. When we arrived, Amy said, "I'm going up to my room to freshen up before dinner. I'll call an Uber and meet you down here in, let's say, twenty minutes?"

I told her that sounded good to me as we entered the elevator, rode it up to our floor, and walked over to our rooms that were right next to each other. I called my wife and talked to her and the kids for a few more minutes, as I wondered just what Amy was doing to freshen up. When I heard her door open, I told them I loved them, and went to join her, riding in the elevator with her down to the lobby.

I didn't notice any changes right away but did think that maybe her blouse had an extra button undone. She still had her black hair down and was wearing the same blouse and tight slacks. She looked a little shorter, so I wondered if she switched out the heels she had been wearing for a smaller pair.

The first part of dinner was mainly Amy picking my brain about what I thought about our tour and how I thought both companies could benefit and help each other. She listened to everything I had to say, gave me her thoughts without making me feel like an idiot, and seemed to be pretty happy with what I had to say.

Just before our food came, Amy changed the subject, claiming she was tired of work talk. As we talked more about our families and our hobbies, I noticed a definite change, as she leaned forward more, her hand reaching out to touch mine, and her knees bumping and resting against mine under the table.

Halfway through dinner, as I said something about my wife, Amy asked, "So, any worries from your wife about your traveling alone? I'm guessing that after almost fifteen years of marriage, she probably trusts you completely?"

I laughed a little and said, "Yes, she does. She knows I'd much rather be in my hotel room, probably playing a game or watching a movie, than I would be out chasing somebody."

"What if you didn't have to go out chasing?" Amy asked, catching me off guard. I took a big gulp of air, as I saw the serious look on her face and was unsure how to respond. Amy smiled as she caught a passing waiter's eye and said, "Can I get the check, please?"

Our drive back to the hotel was quiet, but I noticed Amy sitting a little closer, her legs a little more open than before. We thanked the driver as we were dropped off and I saw him looking at Amy's ass as she started to walk away and part of me wondered if I was about to see more of it. And I wouldn't complain or be upset if the answer was yes.

Inside the lobby, before pressing the button for the elevator, Amy turned to face me and said, "Ryan...whatever happens tonight stays here."

When I didn't respond, instead just staring into her eyes, as she took a step towards me and placed her hand on my arm, she said, "If you're thinking of coming into my room, don't overthink it. Just enjoy it."

The elevator ride was quiet, although my mind was racing. What would happen if I followed her? What if I didn't? Was this a one-time only thing? Or would she expect it whenever we traveled together? What if it was a test? Would word spread? And then, as I was still trying to make up my mind, I glanced down at her and saw a brief glimpse of what looked like a lacy black bra. And I knew I wanted to see more.

In her room, I was still a little nervous. Unsure what to do. Amy had a smile on her face as she set her phone down and walked up to me. "Relax," she whispered as she slowly wrapped her arms around me, stepped up onto her tiptoes, and kissed me.

Her lips were softer than I expected, but there was nothing uncertain about her intentions or what she wanted. She didn't rush it, didn't need to. Every movement was deliberate and controlled, just gentle and patient, like we'd kissed a hundred times and we knew just what we were doing and what the other wanted.

I placed my hands on her hips and was surprised at how small and delicate she felt. Not fragile in any way, but like a treasure I wanted to take care of. As we continued to kiss, Amy unwrapped her arms from my neck and moved them down to my waist. She pulled me closer to her and I could feel the warmth coming from her body, plus a faint hint of perfume I hadn't smelled before.

I felt Amy move, her foot taking a step towards the bed. I hesitated and Amy slowly ended the kiss, and looked into my eyes. I saw a different look in them than I had seen before. I immediately leaned back into her and kissed her lips. As the kiss deepened, neither one of us wanting to end it, Amy's hands moved around to my groin, and started to undo the belt holding up my slacks.

We started to move together, heading towards the bed. Her hands continued to work towards getting my pants off, pushing them down towards my knees where I helped to kick them off. I knew that my cock was hard and pushing against my boxers, and moaned into her mouth when her hand briefly brushed against it.

I moved my hands up and started to undo the belt around her slacks. As I pulled it out of the belt loops, Amy finally rested her hand on my cock, through my boxers, but didn't move it. I hooked my fingers into her slacks, feeling how tight they were, and started to move them down her body. I pulled my lips away from hers, my forehead resting against her forehead, as I looked down, watching as she let go of my cock and helped pull her slacks off.

We finally reached the bed, still kissing, nearly bumping into a few objects along the way, and I felt Amy gently pushing me to sit down. She immediately climbed onto my lap, straddling my legs with hers, and giving me a brief view of her black panties before we resumed kissing.

My breath caught as we kissed and I tried to convince myself that this was really happening. I had Amy, one of the vice presidents of the company I worked for, half naked on my lap, and rubbing her groin against my hard cock. I moved my hands around to her butt and grabbed her cheeks, squeezing them as she rolled her hips and pressed down on my groin, causing Amy to lightly moan into my mouth.

Amy briefly ended the kiss as she pulled my shirt off and ran her hands down my chest, her fingers going through the hair on it. When she reached our groins, she grabbed onto my arms and brought them around to her front. "I want these somewhere else," she said before resuming the kiss.

She lifted my hands up to her chest and placed them on her breasts. The fabric of her blouse was soft under my hands and I could just feel the outline of her bra, as well as the warmth coming from her body. The shape of her breasts pressed into my hands as I lightly squeezed them.

She was softer than I expected, full but with a natural weight to her that shifted slightly as my hands settled. Not firm in the way that I'd be used to, but something else...warmer, more real.

I moved my hands over as I squeezed a few more times, letting my fingertips rub through her blouse, going right above where her bra rested. When I reached the center of her breasts, where she already had the top few buttons undone, she ended the kiss, but continued to move her groin. I looked down and watched as I used my fingers to undo the rest of the buttons.

As her fabric shifted, revealing more of her chest and black lace bra, my movements slowed, without me really thinking about it. The black lace framed her perfectly, pulling my attention in to a sight I'd wanted to see for years.

She wasn't posed or trying to be as she sat on my lap, watching me like she knew exactly what I was seeing and what I felt as I saw it. When my fingers reached the buttons closer to her stomach, I leaned my head down and started to kiss her chest and her cleavage. Amy helped me to pull her blouse off, leaving her in just her bra and panties on my lap.

"Oh, Ryan," she moaned softly, still rolling her hips.

I looked up into her eyes before kissing her lips again. She had her arms hanging loosely at her sides as I reached around and went to unclasp her bra. Amy slid it down her arms, letting it fall between us, and I immediately put my hands on her bare breasts, cupping and squeezing them as we made out.

I was a little surprised at how firm they felt, how quickly her nipples hardened against my palm, and I loved how Amy responded as I touched them. She moaned into my mouth, scooting closer to me, and pressing down more with her groin.

Ending the kiss, I moved my mouth down, going over her neck, to her chest, and ending on her breasts, kissing all over the tops of them. I used my fingers to rub her nipples, making her moan my name again.

Amy brought her hands up and placed her hands on the back of my head, gently pulling me into her breast, as I stuck out my tongue and licked around it. With her encouragement, I wrapped my lips around her nipple and sucked it into my mouth, while I continued to rub her other nipple with my fingers.

I moved back and forth between her breasts, sucking and licking on each nipple as I listened to her moan. Her hip movements never slowed and I could feel my cock aching for it.

Amy must have felt it too as she softly said, "You know, we can always come back to those later."

I understood what she meant as I moved my hand between us and slipped it into her panties, feeling the wetness through her neatly trimmed hair before finding her vagina. I rubbed her slit and lips for a few moments before she said, "Ryan..."

She placed her hands on my shoulders and leaned her body into me as our lips met again. I started to lean backwards as I wrapped my arms around her waist and we were laying on the bed within seconds, still kissing, as we awkwardly moved up to the top of the bed.

When we were there, Amy ended the kiss as she sat up on me and scooted back a bit, just enough that she could hook her fingers into the hem of my boxers and started to pull them down.

I felt like I couldn't breathe as I waited for her reaction. She didn't rush her reaction, if she had one at all. She looked at my face first, smiled slightly as she saw me watching her, then dropped her gaze down to my groin. I had been undressed plenty of times before and wasn't scared or nervous of what I had. But, to be truthful, I'd never been with a woman of Amy's maturity, and didn't want to let her down.

She smiled a little wider as she finished taking my boxers off, and wrapped her hand around my shaft. Her fingers were tiny, matching her petite body, but she knew just what she was doing as she slowly stroked my cock. I moaned a little causing Amy to look up at me and smile.

As I watched her, she used her free hand to move her hair behind her ear and out of her face, before she leaned down, going right over my cock. She lightly blew on it before opening her mouth, sticking out her tongue, and swirling it around my tip.

Amy slowly wrapped her lips around my cock and started to move her mouth up and down my shaft, timing it with her hand. Amy was in no hurry, being in total control, knowing just what to do to maximize the pleasure.

Just like I felt when we kissed, her lips were incredibly soft. She was making every second count as she went up and down. This wasn't a blowjob intended to get me off. It was just a precursor to something more.

"Amy," I softly moaned, matching the same tone she had a few minutes ago.

Amy seemed to know what I meant as she took me out of her mouth and sat back up. I watched as she took off her panties, sliding them down her legs, and then moving back up to line up my cock with her pussy.

I placed my hands on her hips as Amy easily and expertly guided the tip of my cock into her entrance, let go of my shaft, and moved her body down. She moaned softly, closing her eyes, as my cock filled her.

After taking a moment to let us get used to each other, Amy opened her eyes as she started to roll her hips, sliding my cock in and out of her. My mind went blank, enjoying the feeling, the pleasure, of her riding me.

"Oh my God," Amy moaned as she placed her hands close to my stomach, using me to help support her as she went up and down my cock.

I moved my hands off her hips, going around to her butt, where I cupped and squeezed her cheeks, holding on as she rode my cock. Her hands started to slip and she leaned down onto my body, pressing her breasts against me as she kissed my lips.

As we made out, Amy continued to move her hips, sliding her pussy up and down my cock. I kept my hands on her ass, squeezing her cheeks as I pushed up with my hips. Ending the kiss, Amy rested her head next to mine, and moaned into my ear as she slowed her body down.

I took over, using my hands on her ass to move her body, in addition to pushing up with my hips, and burying my cock into her pussy. "Oh my God. Ryan. Don't hold back," she moaned softly.

I moved my hands up and wrapped my arms around her waist as I bent my knees and planted my feet on the bed. Knowing what I was doing, Amy wrapped her arms around my neck and moaned as I flipped us around, keeping my cock inside her, and laying her flat on her back.

We kissed a little more as she spread her legs and arms out. As the kiss ended, I pushed myself above her, placing my hands on the bed, and started to move back and forth. I matched her pace from when she was riding me, going slow and steady. I made sure she got my full length every time, enjoying the feeling of her pussy.

"Hmm...yes. That's just what I needed," Amy moaned, closing her eyes and also enjoying the feeling. She lifted her legs a little and placed her hands down by my butt, as I went in and out of her.

As I looked down at her, seeing the pleasure on her face, her body reacting to mine, her breasts moving with my thrusts, I could feel my orgasm building up.

"Amy...," I moaned out, unable to stop moving.

"Yes, Ryan, yes," she moaned, her fingers digging into my back and holding me in place.

I started to orgasm, my moans joining hers as I continued to move as my cock pumped cum inside the sixty-year-old beauty. I briefly closed my eyes, losing myself in the moment, loving the moment as I climaxed.

I kept moving for as long as I could, wanting to enjoy the feeling of finishing inside her as long as possible. As I finished and could feel my cock starting to go limp, I rolled off Amy and finally thought about what had just happened. Who it was. Why and how it happened. What the consequences might be.

Amy reached over to the bedside table and grabbed a tissue, using it to wipe her groin before throwing the tissue away and rolling onto her side, placing her arm across my chest, and snuggling up against me.

As she rested against me, I wrapped my arm around her, holding her close. She let out a soft moan before saying, "We have an early morning tomorrow. Should probably get to sleep."

"Yeah, we should," I answered but neither of us moved.

She hesitated for a second before saying, "If you wanted to get your belongings from your room, you could stay the night here and who knows what could happen when we wake up."

That got me moving as I finally got up from the bed. I put on just enough clothes to exit her room and step next door to mine. As I left, Amy was still naked on her bed, telling me to hurry back.

I quickly changed into my pajamas in my room before making sure I had everything I had before going back to Amy's room. When I walked back in, I saw that Amy had pulled her black hair back into a ponytail and had put back on her black panties, along with a tight black, spaghetti-string tank top, with a lace trim along the top and bottom.

She laughed as I looked her body up and down, my eyes briefly lingering on her breasts and groin. "Come on, Ryan, let's get to sleep. This old lady needs some rest after that."

We crawled into the bed, covering ourselves with the blanket, before giving each other a small kiss and falling asleep.

When we started to wake up the next morning, Amy had her back to me, and my morning wood was pressing against her ass. I had one arm around her body. "Hmmm...," Amy moaned as she slowly woke up, and wiggled her ass against my cock. "I love waking up to that feeling."

I laughed a little as I moved my hand from her stomach. I went up to her chest and cupped her breast, squeezing it slowly, as I leaned down and started to kiss the back of her neck. She continued to moan, slowly moving her ass, as I slipped my hand inside her tank top, and used my fingers to pinch and rub her nipples.

With my free hand, I slipped it inside her panties, and made a comment about her already being wet.

"I had so many dreams about what you did to me last night. And waking up with you this hard? I'm soaked," she said, opening her legs a little for me to more easily rub her pussy.

"There was one problem with last night," I said as I slowly inserted my finger into her pussy and moved it in and out. When she asked what it was, I told her, "Getting you off."

"Keep doing what you're doing and it'll happen fast," she moaned, closing her eyes and pressing back against me as I kept rubbing her nipples and fingering her pussy.

In and out I went, listening to her wetness squish around my finger, and feeling the inside of her pussy as it clenched around my finger. I moved my other hand between her breasts, taking her nipples between my fingers and rubbing them.

Just as when I touched her nipples the night before, I was surprised with how they felt between my fingers. Softer around the edges but with a firm center that responded immediately to my touch. I alternated between her breasts and couldn't help but wonder how many deals she had sealed by someone seeing her nipples or touching them like I was.

"Oh yes. Right there, Ryan," Amy moaned as I pushed my finger deeper into her, continuing to slide it in and out. She pressed back against me harder, nearly burying my cock into her ass. I felt the tip of my cock slip out of the flap in my boxers, the hardness of it too much to contain and moaned a little as the fabric of her panties rubbed against it.

Amy's breathing started to get sharper and she started to move her body a little more as I kept fingering her. She moved her hand down to her groin, placing it on top of mine and holding my hand there. She moved it up and down a bit, getting my palm to rub her slit as she whispered that she was getting close.

Amy brought her other hand up above her head, reaching for my head. It rested on my cheek as I felt her entire body stiffen, then relax as she let out a deep breath and climaxed.

As she orgasmed, Amy closed her legs around my hand, pinning me to her, with my finger buried deep inside her. I had stopped kissing her neck, but went back to kissing it as she arched her body. I was a little surprised by how quiet her moans were but also knew that she wasn't trying to show off and just wanted to enjoy the experience.

When her orgasm started to subside, she twisted her head around and pulled my lips over to hers, giving me a passionate kiss.

As she pulled her lips away from me, she let out another deep breath and said, "That felt good."

"I'm glad," I told her, keeping my hand on her breast, but just holding it, and removing my hand from her panties as I continued to plant little kisses along her neck.

Amy moaned slightly as I started to move my hips, sliding my cock around her ass. "I want you again...but we do need to start moving. Come take a shower with me. We're not done yet."

A few minutes later, we were standing in the bathroom, the shower going, and stripping off our pajamas. In the shower, Amy briefly used her lips on me again before standing up, and finishing me off with her hand, letting my cum wash away in the water as it poured down around us.

After the shower, we dressed, both of us casting glances towards the other as we covered up, gathered up our belongings, and met an Uber at the door to the hotel. The car ride to the airport was quiet as I lost myself in my thoughts, and Amy answered emails on her phone. During the short flight home, Amy did remark that she would have to see what other mills we could visit, and soon, and I caught a look in her eyes, telling me more than she said out loud.

It took me ten years to work up to a position at my job that I finally felt like I was making enough money to survive. After a decade working in operations, I moved over to the sales team, specifically outside sales. I missed staying in one spot and working with the guys I worked so long with, but it was kind of fun traveling around to different customers and helping them out.

I can't say too much about what I do, except that my company isn't that big. Big enough that we make millions of dollars a year and able to provide our employees with benefits. But small enough that, even as a worker in operations, I knew the entire upper management team and could go have a conversation with any of them and not feel like I was a bother.

The outside sales team had eight people on it, but only two of them worked in the same area I was brought on to help with. They were both only a few years away from retirement, and needed somebody to potentially take over for them. I had known both of them since I started at the company, so going out on the road with them was easy, with no awkwardness at all.

My main boss was named Amy, who was a vice president in the company. She was on the road daily, keeping up relations with customers and always on the lookout for new ones. And, since we were a middleman who sold specific products from one company to the next, we were always talking to companies that we might want to buy from, to offer their product for sale, something I quickly found out that Amy excelled at. Watching her sell our company to another, trying to convince them to use us to sell their product was magic and I knew that I had a lot to learn from her.

While I spent the first few months working for outside sales out on the road, traveling some days with Amy and other days with the other team member, a guy named Robert, I was still home every night, something that made my wife and four kids happy. When I accepted the job with them, I was warned that a few times a year, I would have to travel outside the state, visiting different plants that made the products we sold, and promoting relations with them.

The first time I had to travel somewhere, I woke up around three in the morning, planning on being at the airport around 4:30. After silencing my alarm, I went to the bathroom, took an incredibly quick shower, and then brushed my teeth. As I brushed, I looked at myself in the mirror. I had recently trimmed my brown hair down a bit, but it was still a little shaggy. My beard was cut close to my face, framing my jaw. After cleaning out my toothbrush, I put in my contacts, blinking my blue eyes a few times to get them into focus. When my deodorant was on, I tossed it, my toothbrush and paste, and contact case and solution into a bag, and put that into a suitcase packed for a couple days of travel.

I was still getting used to a newer dress code, having to change nearly my entire wardrobe with the new position. Gone were the days of wearing basketball shorts or dirty jeans and a ripped shirt or old hoodie. Now it was clean jeans or slacks and polo shirts. I grabbed a quick breakfast to eat on the go before kissing my wife goodbye and getting in my car to drive to the airport.

At the airport, I met Amy after I got through security. She gave me a quick hug, already full of energy, and almost instantly started going over the itinerary for our quick trip.

As she talked, I couldn't help but stare at her. She was in her late fifties or early sixties, and just beautiful. Long black hair, an amazing smile, and a killer petite body that I knew she used to her advantage when she felt the need to. An extra button undone on an already low cut blouse. Slacks or jeans that were too tight. It was fun to watch guys casting glances her way, especially as we got up from our seats in the terminal to grab a snack and drink for the trip.

When we sat back down at the gate, Amy answered her phone and I overheard her say, "Yeah, Ryan's here with me at the gate. Should be boarding soon. Yes, he's pretty prepared for it. I'm excited as well. I'll check in later."

As she hung up, she was shaking her head and I jokingly said, "Vice President of the company and still having to check in with others?"

Amy laughed and said, "It was Robert. He hates me traveling alone, so he's glad you're coming along. We're always checking in with each other."

The plane ride from Utah to Washington only took a couple of hours and we spent the time getting to know each other a little better. It was fun to hear about her experience as a working mom, raising three children, while working sixty hours a week and her husband was always gone, working as a contractor. I made an offhand joke about a lot of lonely nights and she threw me off guard when she said, "I didn't have a whole ton of those, even with him gone."

"The kids do seem to fill those nights, don't they?" I commented back.

"I wasn't talking about kids," Amy responded in a deadpan tone and I honestly couldn't tell if she was joking or not.

When we landed in Washington, the company we were touring that day had a car waiting for us. It drove us over to our hotel, letting us check in and drop off our bags before driving us to the plant, where we were greeted by a few of the main executives of the company.

During our tour, I mainly took a step back, watching as Amy took charge, asking all the right questions, not revealing too much, and really making a good impression on everybody she met. And, just like at the airport, I caught more than one guy doing a double check when she walked past.

After the tour of the plant, we all went to a nearby restaurant for lunch. Amy and I sat next to each other. On more than one occasion, she touched my arm, as she explained more about what I did for the company, my background, and what I would be doing in the future.

Every time she touched my arm, I felt a shiver go up it and the few times we made eye contact with each other, I felt like she held the gaze a little longer than usual. But, I could have been imagining things.

It was just us in the company car on the drive back to the plant after lunch, plus the driver behind a closed window. We were talking about our impressions of the company and people we were meeting with when Amy said, "So, what do you think about Sam, their VP of Sales? Did you see the eyes he was making at me? How bad do you think he wants to fuck me?"

She said it so nonchalantly that it caught me totally off guard and I wasn't sure how to respond, stammering out something about me not noticing.

"Relax," she said with a laugh. "I know how most of these guys see me. I know what they want. I've even given in a few times. Like I said on the plane, I don't have a lot of lonely nights and if it helps the company, even better."

When I didn't respond right away, Amy smiled and said, "But don't worry. He won't be coming back to my room tonight. Hopefully somebody else will be."

I could have sworn she was batting her eyes at me as she talked. Was she always like this? Was I reading too much into it? I had no idea but I did know that I was going to have trouble getting out of the car without somebody seeing something.

For the rest of the afternoon, we were stuck in a conference room, listening to PowerPoint presentations from three different people, explaining more about the company, the product, and what they thought they could offer us.

At one point, Amy stepped out of the conference room to take a phone call and Sam, the executive she thought was checking her out, turned to me and said, "Man, it must be great traveling with her."

"Yes, it is. I'm learning a lot from her," I responded, keeping it professional although the look on his face told me he wasn't.

He laughed a little before asking, "I bet she gets noticed a lot."

I simply shrugged my shoulders, acting like I hadn't thought about it.

As the day wrapped up, Amy and I said our goodbyes to everybody we had been meeting with, promised to stay in touch, and were driven back to our hotel. When we arrived, Amy said, "I'm going up to my room to freshen up before dinner. I'll call an Uber and meet you down here in, let's say, twenty minutes?"

I told her that sounded good to me as we entered the elevator, rode it up to our floor, and walked over to our rooms that were right next to each other. I called my wife and talked to her and the kids for a few more minutes, as I wondered just what Amy was doing to freshen up. When I heard her door open, I told them I loved them, and went to join her, riding in the elevator with her down to the lobby.

I didn't notice any changes right away but did think that maybe her blouse had an extra button undone. She still had her black hair down and was wearing the same blouse and tight slacks. She looked a little shorter, so I wondered if she switched out the heels she had been wearing for a smaller pair.

The first part of dinner was mainly Amy picking my brain about what I thought about our tour and how I thought both companies could benefit and help each other. She listened to everything I had to say, gave me her thoughts without making me feel like an idiot, and seemed to be pretty happy with what I had to say.

Just before our food came, Amy changed the subject, claiming she was tired of work talk. As we talked more about our families and our hobbies, I noticed a definite change, as she leaned forward more, her hand reaching out to touch mine, and her knees bumping and resting against mine under the table.

Halfway through dinner, as I said something about my wife, Amy asked, "So, any worries from your wife about your traveling alone? I'm guessing that after almost fifteen years of marriage, she probably trusts you completely?"

I laughed a little and said, "Yes, she does. She knows I'd much rather be in my hotel room, probably playing a game or watching a movie, than I would be out chasing somebody."

"What if you didn't have to go out chasing?" Amy asked, catching me off guard. I took a big gulp of air, as I saw the serious look on her face and was unsure how to respond. Amy smiled as she caught a passing waiter's eye and said, "Can I get the check, please?"

Our drive back to the hotel was quiet, but I noticed Amy sitting a little closer, her legs a little more open than before. We thanked the driver as we were dropped off and I saw him looking at Amy's ass as she started to walk away and part of me wondered if I was about to see more of it. And I wouldn't complain or be upset if the answer was yes.

Inside the lobby, before pressing the button for the elevator, Amy turned to face me and said, "Ryan...whatever happens tonight stays here."

When I didn't respond, instead just staring into her eyes, as she took a step towards me and placed her hand on my arm, she said, "If you're thinking of coming into my room, don't overthink it. Just enjoy it."

The elevator ride was quiet, although my mind was racing. What would happen if I followed her? What if I didn't? Was this a one-time only thing? Or would she expect it whenever we traveled together? What if it was a test? Would word spread? And then, as I was still trying to make up my mind, I glanced down at her and saw a brief glimpse of what looked like a lacy black bra. And I knew I wanted to see more.

In her room, I was still a little nervous. Unsure what to do. Amy had a smile on her face as she set her phone down and walked up to me. "Relax," she whispered as she slowly wrapped her arms around me, stepped up onto her tiptoes, and kissed me.

Her lips were softer than I expected, but there was nothing uncertain about her intentions or what she wanted. She didn't rush it, didn't need to. Every movement was deliberate and controlled, just gentle and patient, like we'd kissed a hundred times and we knew just what we were doing and what the other wanted.

I placed my hands on her hips and was surprised at how small and delicate she felt. Not fragile in any way, but like a treasure I wanted to take care of. As we continued to kiss, Amy unwrapped her arms from my neck and moved them down to my waist. She pulled me closer to her and I could feel the warmth coming from her body, plus a faint hint of perfume I hadn't smelled before.

I felt Amy move, her foot taking a step towards the bed. I hesitated and Amy slowly ended the kiss, and looked into my eyes. I saw a different look in them than I had seen before. I immediately leaned back into her and kissed her lips. As the kiss deepened, neither one of us wanting to end it, Amy's hands moved around to my groin, and started to undo the belt holding up my slacks.

We started to move together, heading towards the bed. Her hands continued to work towards getting my pants off, pushing them down towards my knees where I helped to kick them off. I knew that my cock was hard and pushing against my boxers, and moaned into her mouth when her hand briefly brushed against it.

I moved my hands up and started to undo the belt around her slacks. As I pulled it out of the belt loops, Amy finally rested her hand on my cock, through my boxers, but didn't move it. I hooked my fingers into her slacks, feeling how tight they were, and started to move them down her body. I pulled my lips away from hers, my forehead resting against her forehead, as I looked down, watching as she let go of my cock and helped pull her slacks off.

We finally reached the bed, still kissing, nearly bumping into a few objects along the way, and I felt Amy gently pushing me to sit down. She immediately climbed onto my lap, straddling my legs with hers, and giving me a brief view of her black panties before we resumed kissing.

My breath caught as we kissed and I tried to convince myself that this was really happening. I had Amy, one of the vice presidents of the company I worked for, half naked on my lap, and rubbing her groin against my hard cock. I moved my hands around to her butt and grabbed her cheeks, squeezing them as she rolled her hips and pressed down on my groin, causing Amy to lightly moan into my mouth.

Amy briefly ended the kiss as she pulled my shirt off and ran her hands down my chest, her fingers going through the hair on it. When she reached our groins, she grabbed onto my arms and brought them around to her front. "I want these somewhere else," she said before resuming the kiss.

She lifted my hands up to her chest and placed them on her breasts. The fabric of her blouse was soft under my hands and I could just feel the outline of her bra, as well as the warmth coming from her body. The shape of her breasts pressed into my hands as I lightly squeezed them.

She was softer than I expected, full but with a natural weight to her that shifted slightly as my hands settled. Not firm in the way that I'd be used to, but something else...warmer, more real.

I moved my hands over as I squeezed a few more times, letting my fingertips rub through her blouse, going right above where her bra rested. When I reached the center of her breasts, where she already had the top few buttons undone, she ended the kiss, but continued to move her groin. I looked down and watched as I used my fingers to undo the rest of the buttons.

As her fabric shifted, revealing more of her chest and black lace bra, my movements slowed, without me really thinking about it. The black lace framed her perfectly, pulling my attention in to a sight I'd wanted to see for years.

She wasn't posed or trying to be as she sat on my lap, watching me like she knew exactly what I was seeing and what I felt as I saw it. When my fingers reached the buttons closer to her stomach, I leaned my head down and started to kiss her chest and her cleavage. Amy helped me to pull her blouse off, leaving her in just her bra and panties on my lap.

"Oh, Ryan," she moaned softly, still rolling her hips.

I looked up into her eyes before kissing her lips again. She had her arms hanging loosely at her sides as I reached around and went to unclasp her bra. Amy slid it down her arms, letting it fall between us, and I immediately put my hands on her bare breasts, cupping and squeezing them as we made out.

I was a little surprised at how firm they felt, how quickly her nipples hardened against my palm, and I loved how Amy responded as I touched them. She moaned into my mouth, scooting closer to me, and pressing down more with her groin.

Ending the kiss, I moved my mouth down, going over her neck, to her chest, and ending on her breasts, kissing all over the tops of them. I used my fingers to rub her nipples, making her moan my name again.

Amy brought her hands up and placed her hands on the back of my head, gently pulling me into her breast, as I stuck out my tongue and licked around it. With her encouragement, I wrapped my lips around her nipple and sucked it into my mouth, while I continued to rub her other nipple with my fingers.

I moved back and forth between her breasts, sucking and licking on each nipple as I listened to her moan. Her hip movements never slowed and I could feel my cock aching for it.

Amy must have felt it too as she softly said, "You know, we can always come back to those later."

I understood what she meant as I moved my hand between us and slipped it into her panties, feeling the wetness through her neatly trimmed hair before finding her vagina. I rubbed her slit and lips for a few moments before she said, "Ryan..."

She placed her hands on my shoulders and leaned her body into me as our lips met again. I started to lean backwards as I wrapped my arms around her waist and we were laying on the bed within seconds, still kissing, as we awkwardly moved up to the top of the bed.

When we were there, Amy ended the kiss as she sat up on me and scooted back a bit, just enough that she could hook her fingers into the hem of my boxers and started to pull them down.

I felt like I couldn't breathe as I waited for her reaction. She didn't rush her reaction, if she had one at all. She looked at my face first, smiled slightly as she saw me watching her, then dropped her gaze down to my groin. I had been undressed plenty of times before and wasn't scared or nervous of what I had. But, to be truthful, I'd never been with a woman of Amy's maturity, and didn't want to let her down.

She smiled a little wider as she finished taking my boxers off, and wrapped her hand around my shaft. Her fingers were tiny, matching her petite body, but she knew just what she was doing as she slowly stroked my cock. I moaned a little causing Amy to look up at me and smile.

As I watched her, she used her free hand to move her hair behind her ear and out of her face, before she leaned down, going right over my cock. She lightly blew on it before opening her mouth, sticking out her tongue, and swirling it around my tip.

Amy slowly wrapped her lips around my cock and started to move her mouth up and down my shaft, timing it with her hand. Amy was in no hurry, being in total control, knowing just what to do to maximize the pleasure.

Just like I felt when we kissed, her lips were incredibly soft. She was making every second count as she went up and down. This wasn't a blowjob intended to get me off. It was just a precursor to something more.

"Amy," I softly moaned, matching the same tone she had a few minutes ago.

Amy seemed to know what I meant as she took me out of her mouth and sat back up. I watched as she took off her panties, sliding them down her legs, and then moving back up to line up my cock with her pussy.

I placed my hands on her hips as Amy easily and expertly guided the tip of my cock into her entrance, let go of my shaft, and moved her body down. She moaned softly, closing her eyes, as my cock filled her.

After taking a moment to let us get used to each other, Amy opened her eyes as she started to roll her hips, sliding my cock in and out of her. My mind went blank, enjoying the feeling, the pleasure, of her riding me.

"Oh my God," Amy moaned as she placed her hands close to my stomach, using me to help support her as she went up and down my cock.

I moved my hands off her hips, going around to her butt, where I cupped and squeezed her cheeks, holding on as she rode my cock. Her hands started to slip and she leaned down onto my body, pressing her breasts against me as she kissed my lips.

As we made out, Amy continued to move her hips, sliding her pussy up and down my cock. I kept my hands on her ass, squeezing her cheeks as I pushed up with my hips. Ending the kiss, Amy rested her head next to mine, and moaned into my ear as she slowed her body down.

I took over, using my hands on her ass to move her body, in addition to pushing up with my hips, and burying my cock into her pussy. "Oh my God. Ryan. Don't hold back," she moaned softly.

I moved my hands up and wrapped my arms around her waist as I bent my knees and planted my feet on the bed. Knowing what I was doing, Amy wrapped her arms around my neck and moaned as I flipped us around, keeping my cock inside her, and laying her flat on her back.

We kissed a little more as she spread her legs and arms out. As the kiss ended, I pushed myself above her, placing my hands on the bed, and started to move back and forth. I matched her pace from when she was riding me, going slow and steady. I made sure she got my full length every time, enjoying the feeling of her pussy.

"Hmm...yes. That's just what I needed," Amy moaned, closing her eyes and also enjoying the feeling. She lifted her legs a little and placed her hands down by my butt, as I went in and out of her.

As I looked down at her, seeing the pleasure on her face, her body reacting to mine, her breasts moving with my thrusts, I could feel my orgasm building up.

"Amy...," I moaned out, unable to stop moving.

"Yes, Ryan, yes," she moaned, her fingers digging into my back and holding me in place.

I started to orgasm, my moans joining hers as I continued to move as my cock pumped cum inside the sixty-year-old beauty. I briefly closed my eyes, losing myself in the moment, loving the moment as I climaxed.

I kept moving for as long as I could, wanting to enjoy the feeling of finishing inside her as long as possible. As I finished and could feel my cock starting to go limp, I rolled off Amy and finally thought about what had just happened. Who it was. Why and how it happened. What the consequences might be.

Amy reached over to the bedside table and grabbed a tissue, using it to wipe her groin before throwing the tissue away and rolling onto her side, placing her arm across my chest, and snuggling up against me.

As she rested against me, I wrapped my arm around her, holding her close. She let out a soft moan before saying, "We have an early morning tomorrow. Should probably get to sleep."

"Yeah, we should," I answered but neither of us moved.

She hesitated for a second before saying, "If you wanted to get your belongings from your room, you could stay the night here and who knows what could happen when we wake up."

That got me moving as I finally got up from the bed. I put on just enough clothes to exit her room and step next door to mine. As I left, Amy was still naked on her bed, telling me to hurry back.

I quickly changed into my pajamas in my room before making sure I had everything I had before going back to Amy's room. When I walked back in, I saw that Amy had pulled her black hair back into a ponytail and had put back on her black panties, along with a tight black, spaghetti-string tank top, with a lace trim along the top and bottom.

She laughed as I looked her body up and down, my eyes briefly lingering on her breasts and groin. "Come on, Ryan, let's get to sleep. This old lady needs some rest after that."

We crawled into the bed, covering ourselves with the blanket, before giving each other a small kiss and falling asleep.

When we started to wake up the next morning, Amy had her back to me, and my morning wood was pressing against her ass. I had one arm around her body. "Hmmm...," Amy moaned as she slowly woke up, and wiggled her ass against my cock. "I love waking up to that feeling."

I laughed a little as I moved my hand from her stomach. I went up to her chest and cupped her breast, squeezing it slowly, as I leaned down and started to kiss the back of her neck. She continued to moan, slowly moving her ass, as I slipped my hand inside her tank top, and used my fingers to pinch and rub her nipples.

With my free hand, I slipped it inside her panties, and made a comment about her already being wet.

"I had so many dreams about what you did to me last night. And waking up with you this hard? I'm soaked," she said, opening her legs a little for me to more easily rub her pussy.

"There was one problem with last night," I said as I slowly inserted my finger into her pussy and moved it in and out. When she asked what it was, I told her, "Getting you off."

"Keep doing what you're doing and it'll happen fast," she moaned, closing her eyes and pressing back against me as I kept rubbing her nipples and fingering her pussy.

In and out I went, listening to her wetness squish around my finger, and feeling the inside of her pussy as it clenched around my finger. I moved my other hand between her breasts, taking her nipples between my fingers and rubbing them.

Just as when I touched her nipples the night before, I was surprised with how they felt between my fingers. Softer around the edges but with a firm center that responded immediately to my touch. I alternated between her breasts and couldn't help but wonder how many deals she had sealed by someone seeing her nipples or touching them like I was.

"Oh yes. Right there, Ryan," Amy moaned as I pushed my finger deeper into her, continuing to slide it in and out. She pressed back against me harder, nearly burying my cock into her ass. I felt the tip of my cock slip out of the flap in my boxers, the hardness of it too much to contain and moaned a little as the fabric of her panties rubbed against it.

Amy's breathing started to get sharper and she started to move her body a little more as I kept fingering her. She moved her hand down to her groin, placing it on top of mine and holding my hand there. She moved it up and down a bit, getting my palm to rub her slit as she whispered that she was getting close.

Amy brought her other hand up above her head, reaching for my head. It rested on my cheek as I felt her entire body stiffen, then relax as she let out a deep breath and climaxed.

As she orgasmed, Amy closed her legs around my hand, pinning me to her, with my finger buried deep inside her. I had stopped kissing her neck, but went back to kissing it as she arched her body. I was a little surprised by how quiet her moans were but also knew that she wasn't trying to show off and just wanted to enjoy the experience.

When her orgasm started to subside, she twisted her head around and pulled my lips over to hers, giving me a passionate kiss.

As she pulled her lips away from me, she let out another deep breath and said, "That felt good."

"I'm glad," I told her, keeping my hand on her breast, but just holding it, and removing my hand from her panties as I continued to plant little kisses along her neck.

Amy moaned slightly as I started to move my hips, sliding my cock around her ass. "I want you again...but we do need to start moving. Come take a shower with me. We're not done yet."

A few minutes later, we were standing in the bathroom, the shower going, and stripping off our pajamas. In the shower, Amy briefly used her lips on me again before standing up, and finishing me off with her hand, letting my cum wash away in the water as it poured down around us.

After the shower, we dressed, both of us casting glances towards the other as we covered up, gathered up our belongings, and met an Uber at the door to the hotel. The car ride to the airport was quiet as I lost myself in my thoughts, and Amy answered emails on her phone. During the short flight home, Amy did remark that she would have to see what other mills we could visit, and soon, and I caught a look in her eyes, telling me more than she said out loud.

"Oh my gosh! Oh my gosh! Do it! Finish in me!"

I was lying naked in my bed, with my summer boyfriend, Connor, sliding his cock in and out of me. This was probably the last time we would sleep together, as tomorrow I was driving back home to Springfield, Massachusetts, while he was staying in Cape Cod. It was only a two-hour drive, but being twenty years old, it felt like forever.

Connor leaned down, pressing his chest against mine as I wrapped my limbs around his body. I could feel him getting closer and closer, his breathing getting more and more shallow, his thrusts shorter and harder.

Two months ago, when I came out to stay with my grandma for the summer, just like I had every year of my life, I never would have thought this possible. I hated Connor. He was always the bully growing up and I couldn't stand the thought or sight of him.

He moaned into my ear that he was starting to cum and I felt his cock pushing deep into me. I pushed my hips up, letting out my own moan, feeling his cock fill me up.

Connor gave me a kiss that I eagerly returned as he rolled off me. I quickly grabbed a few tissues from next to my bed, handing him one and I used the other to clean myself up.

I rolled over after throwing the tissues away, landing in Connor's outstretched arm. As he wrapped it around me, he gave the top of my head a kiss and said, "I'm going to miss you, City Girl."

........

"Hey, City Girl. Been a while," I heard Connor say. It was the end of May and I had just arrived in Cape Cod, driving right from the campus of UMass Amherst, where I had just finished my sophomore year.

I had been coming to Cape Cod every summer to live with my grandmother for as long as I could remember. And for as long as I could remember, Connor was there to tease and bully me. And I hated it.

Connor was a year older, but I seemed to run into him everywhere I went. A country club, the beach, out to lunch or dinner, even on the few dates I went on as I got older. And he never failed to say something mean or rude. His dad was a high-level executive for one of the companies that operated off the docks in Cape Cod, and his large house was just a few houses down from my grandmother's.

The first few weeks, everything went pretty smoothly. I reconnected with the friends I had there, put in a few job applications, and spent some quality time with my grandmother. She had been wanting to teach me to cook for a while, and I was finally willing to accept her help. It was great. I even had a boy ask me out on a date.

Unfortunately, the date didn't go anywhere. Really unfortunately for me, because I was starting to feel pretty horny. I had a friend I had slept with right before leaving for Cape Cod, but I wasn't used to go longer than two weeks without any sex. And I didn't like it.

I was offered, and accepted a job working for a local hotel, working at their front desk. I was excited, not only because it was my first Big Girl job, but because they offered free pool and gym access to all of their employees, seasonal or full-time.

The one drawback to the job was that Connor worked there as well, doing maintenance. I just had to hope that the hotel would be big enough to avoid him and to keep reminding myself that he couldn't bully me while we worked.

I did have to work a few late night shifts, but I honestly didn't mind them. The other girls that worked it were all the same age as me and we were soon best friends, going out before or after work.

One of the nights that I wasn't going out with them, I stuck around the hotel, getting in a quick workout at the hotel's gym before putting on my swimsuit and cooling down in the pool.

After I finished in the pool, I went into the locker room, pulled off my swimsuit, and took a quick shower. When my shower was done, I toweled myself off and looked at myself in the full-length mirror.

I was twenty years old, but could easily pass for younger. My hair was a little messy, like it always was when I came to the coast, and falling past my shoulders in loose waves. It always got lighter in the summer, a blonde, almost golden in the sun, and never really sat how I wanted it to. Maybe one day I'd learn to do it.

I was starting to tan a little, a product of spending a little bit of time on the beach. Come August, it would really set in, and I was already thinking of ways and places I could tan nude. I was of middling height, neither tall nor short. With a mostly flat stomach and skinny legs and arms, the reasons why I was going to the gym as much as possible.

My chest was on the smaller side, but that didn't stop me from running my hands over my breasts and giving them a quick squeeze. Always had been. They fit me, but there was a time I wished I had my mom's chest.

I turned slightly in the mirror and glanced over my shoulder. I loved it when a guy grabbed my ass, even if there wasn't much there. Another reason to go to the gym.

As I turned back to fully face the mirror, I heard a sound behind me and looked up just as Connor turned the corner into the shower area.

"Connor! What the fuck!" I screamed as I dove for a towel and tried to hide my body. Connor jumped, scared by my yelling and ducked back behind the wall. I quickly moved back into a shower stall.

"Shit, sorry, Jackie, I didn't know you were in here," he stammered out.

"Oh really? But you didn't think to check? You make it a habit to just walk into a women's locker room?" I was seething, wishing he would just leave, unable to believe he caught me like this. He was never going to let me forget it. Hopefully he didn’t actually see anything that he would remember.

"I'm sorry, Jackie, I really am," he said and I actually think I believed him. "I was just told there was a broken shower head here and I figured that it was late enough, nobody would be in here."

I peeked my head out just as Connor did the same. I could instantly see the regret on his face and kinda felt sorry for yelling at him. "Hey, look, I'm...." as I started to apologize, I noticed his eyes going to the mirror and thought that he could see my reflection in it. "Are you trying to look at me naked?"

Connor shook his head and tried to stammer out something else but I shushed him and said, "Do you like what you see?"

I briefly thought about stepping out, letting him see me naked, and could even feel myself already getting turned on. When he shyly answered yes, I said, "Good. Now get out so I can get dressed."

Later that night, I was still turned on. As I lay in my bed, I brought my hand down to my groin, pulled my pajama shorts down, and started to touch myself. I closed my eyes, images flashing through my mind, mostly of Connor, both surprising me, and leaving me turned on. It wasn't the same as what a guy could do to me, but I still got myself off, feeling some relief.

But from Connor?

The next few shifts that I worked, Connor actually sought me out, making sure to apologize every time he did so. He was actually being nice to me and I wasn't sure if it was because he didn't want me to get him in trouble, or his mindset had changed after seeing me naked.

A week and a half after my shower run in with Connor, I was again working the front desk, but this time by myself. Connor came up to check on me a few hours before the shift ended, just as a panicked call from a guest came in.

"Ok. OK. I understand. My maintenance is right here and I have another room available. I'll bring him right over and I'll take you to your new room," I said, hoping I was doing the right thing.

I looked up at Connor as I hung up the phone and said, "Room 203 says their bathroom is flooding. Something about the shower being stuck. I have a vacant room I can put them in while you fix it."

"Let's go," Connor said as I put a sign up letting anybody know that I would be back and grabbing the vacate room's key.

We quickly made our way to the room that was flooding and knocked on the door. Connor went right in and immediately to the bathroom, while I escorted the guest out of the room, helping to grab their belongings.

After making sure that the guest was taken care of, I went back to room 203, seeing if Connor needed any help.

"Hey, Connor? You doing OK? Anything I could do to help?" I called out, no longer hearing any water flowing.

"Ummm...towels? If housekeeping is here, can you get them to bring up a lot of towels?" I heard him answer me from the bathroom.

I knew that housekeeping had already left, so after quickly checking the front desk, I quickly walked to where the towels were kept, grabbed as many as I could fit on a cart, and went back up to Connor. He wasn't in the room when I came back, but there was still water on the floor, so I started to lay down the towels to soak it up.

"Oh, thanks, Jackie. You didn't have to do that," Connor said a few minutes later, coming back into the room with a toolbox in his hand.

"No worries. Wanted to help," I told him.

He helped me to soak up the water, both of us getting wet in the process. There were a few times where our hands accidentally touched and we would make eye contact, both of us quickly looking away.

When we were done, we sat back on the floor, our backs against the wall, breathing deeply.

"You look confused," Connor said a minute later, looking over at me.

I was. I was turned on. So turned on. And it was just from being around him and our brief touches. But why?

I took a big breath and shook my head, trying to clear my thoughts.

"Not used to hard work?" Connor said and I couldn't tell if he was joking or not.

Being alone in a room with him, I finally decided to give him a taste of his own medicine.

"Why are you always so mean to me? Are we still in elementary school? You being mean to a girl cause you like her?"

Now it was Connor's turn to look confused. "Shouldn't you go back to the front desk? Don't want a guest walking in with nobody there."

"Don't deflect. I know you were checking me out in the locker room. You probably went home and jacked off to what you saw, didn't you?" I continued to tease him, still feeling the warmth in my groin.

"I...umm...I...what the fuck are you talking about?"

I stood up off the floor, smiling down at him. "Don't worry. You can admit it. I will. I went home that night and enjoyed myself."

Before he could process what I said, I turned and walked out of the room, making sure to put one foot in front of the other, making my ass sway as I walked away.

I wasn't sure what my game plan was as I walked away. Did I want Connor? Part of me said yes and another part remembered how much I hated him. But, seeing him confused and speechless made him kind of cute.

A few seconds later, I heard him call my name, and turned to see him jogging to catch up to me.

"What was that about?" he asked as he stopped a few feet from me.

I shrugged and then turned away again, quickly walking to a door leading to a stairwell. Connor was right on my heels and when I felt him reaching for me, I turned again to face him, smacking his hand away. "Look, Connor, I don't know! You've always been so mean to me! I hate you. I don't know why, but every year that I'm here, for just a few months of the year, you seem to make it your life's mission to make my life hell. And now, now you want me to explain myself to you? No! You explain yourself. Now."

"I..." Connor started, taking a step back and leaning up against the door.

"You what?" I said, folding my arms against my chest. When he didn't immediately respond, I said, "I need to get back to the desk. I don't have time for this."

As I tried to walk away, Connor reached out and grabbed my arm, stopping me in my tracks. "Look, Jackie, this isn't easy for me. At first, yeah, I was just being mean to you because I was young, dumb, and that's how we treated new people. Summer people. City girls. And then as we got older, it was just a habit. I never gave you a chance. And I'm sorry for it."

"So, what changed? Me working here? Seeing me naked? Maybe hoping it would lead to something else?" As I talked, I watched Connor looking my body up and down and I knew what he wanted. Before he could respond, I laughed, and said, "That's what I thought."

I immediately turned and walked down to the first floor. Thinking the entire time, that I wanted the same thing.

An hour before my shift ended, I used the desk phone to call maintenance. When Connor answered, I said, "After we're off, meet me at the beach. You know the spot. Bye." I hung up the phone before he could respond and could feel the familiar warmth in my groin as I smiled to myself.

I pulled into the beach parking lot a short time later and reached into the backseat of my car to grab a bag I kept there. My hotel uniform was simple and modest, and I quickly pulled my blouse out of my slacks and started to unbutton it. I had a white tank top under it and briefly debated on pulling on a sweatshirt. It was sixty degrees but felt a lot cooler next to the ocean.

I pulled a towel and my beach sandals out of the bag, stuffed my work blouse into it, and opened the car door. I changed my shoes before shutting the door and walking to where I hoped Connor would meet me.

I didn't have to wait very long as I heard his car pull up and him walking up to the little private area that everybody knew about but nobody would admit to it. "Hi," we both said simply.

We both stood there awkwardly, staring at each other. I don't think I had ever actually been alone with Connor, besides tonight at work. But, out on the beach, hearing the waves crashing onto the rocks that were nearby, all the memories of how he treated me came flooding back.

Connor broke our gaze first, looking off to the side, and I wondered if he was having the same feelings. He looked different, somehow, almost seeming like he wanted to act one way, but knew he shouldn't. Or couldn't.

I wasn't sure what to feel. I still didn't like Connor. Too many years of him being a bully. But the way he looked at me...our brief, accidental touches...my own horniness...maybe, just maybe this was right.

When he looked back at me, I made a decision. I was going to do this. But on my terms.

I had laid the towel down on the sand and saw him glance at it. "Look, Connor. I don't know what's going on between us. But, I feel an attraction. And I need it. I don't want anything permanent or long term or even short term. I just want to be taken care of this summer. I want somebody reliable and good. Can you do that for me?"

Connor nodded his head and I saw him looking at my body again, pausing at my chest. In the cool night, with a soft breeze blowing from the ocean, my nipples had hardened almost instantly, poking out through my bra and tank top.

I took a few steps towards him and looked up. Connor was a few inches taller than me, with sandy blonde hair that he kept cut pretty short. I wrapped my arms around his neck and pulled him down to kiss me.

Connor kept his eyes open, staring at me, and for a moment, I was wondering if I was his first kiss. But then, he grabbed onto my hips and returned the kiss with a fiery passion, one that told me that all of my assumptions lately were correct.

As we made out, our heads twisting and turning, our lips never leaving each other, I moved my hands down to his groin and started to undo the buttons holding up his jeans. As I pulled apart his jeans, I slipped my hand inside them, moaning into his mouth as I started to rub his cock.

I was pleasantly surprised to find that his cock fit into my hand perfectly. It wasn't too big or too small...it was comfortable. As I ended the kiss and started to drop into a squat position, I pulled his pants and boxers down, letting his cock bounce free, and smiling as I saw it.

"You like that, don't you baby? Nice and thick, ain't it?" Connor said as I stroked his cock with my hand.

I laughed a little at his dumb comment and wondering if he was being serious. I stuck out my tongue and licked around his tip for a minute as Connor put one of his hands on the back of my head, trying to guide me more to his cock.

As I wrapped my lips around his shaft and started to bob my head up and down, while still using my hand on him, Connor reached down, roughly grabbing at my breast through my tank top and squeezing it.

"Your tits aren't very big, but fuck are they nice to grab," he said, slipping his hand inside my tank top and bra.

I took him out of my mouth, keeping my hand going on his shaft, and said, "If you want to fuck me, you better stop talking."

I started to lay down on the towel, pulling my slacks and underwear down and off my feet. Connor was right there, kissing all over my neck and chest, and using his hand to pull my tank top and bra up. I reached down between us and guided his cock into my pussy as he licked my nipples, moving back and forth between the two.

I had to put my hands on his butt and wrap my legs around his in order to encourage him to push inside me, letting out a moan as his cock filled my pussy. Connor had his hands on the towel to support himself as he continued to kiss and lick my nipples.

"For them being small, you sure do seem to enjoy them," I teased him as he slowly started to move back and forth, sliding his cock in and out of me.

"Should I stop?" he asked, looking up at me.

"No," I said. "But you can go a little harder."

Connor did stop kissing my breasts, instead focusing on slamming his cock into me, hard and fast. I closed my eyes, enjoying the feeling of once again having a man inside me. It had been far too long.

I kept my legs wrapped around his waist, feeling them moving as he moved. I moved my hands off his butt, going up and over his back, rubbing with my fingers as I went.

"Am I allowed to say how hot you are?" he asked as he went into me over and over.

"Yes," I breathed out, in between moans.

"You're so fucking hot," he said. "I'm going to cum. Do I need to pull out?"

"No," I said, wrapping my legs tighter around him.

Connor continued to slam into me, his waist pinning me to the towel as he went as hard as he could. His grunts and groans started to get louder until he finally pushed as deep into me as he could, and started to orgasm. I kept my legs wrapped around him as his cock shot his cum into me.

"Oh yes. God yes," I moaned before Connor leaned down and kissed me.

When he was done with his orgasm, he slowly pulled out and I felt empty again as his cock left me.

"I can't believe that just happened," he said as he rolled over, laying down next to me.

I couldn't either, I thought to myself as I lay on the towel, nearly completely naked, having just been fucked by a guy I hated. Or thought I did.

The next couple of weeks, Connor and I didn't talk too much. But, we spent a lot of time together. If we worked a day shift together, we often snuck off somewhere, usually during our lunch times, often making out in his car, and always ending with a blowjob. When we worked nights, the beach became our favorite spot. And, the few days that we both had off, it was either his dad's house or my grandma's house, but always in a bed, and always ending with us both satisfied.

We did have a few instances where I thought that Connor was the same old mean Connor. Certain words or phrases would slip out. Especially when I was giving him oral. He told me one day while we were at work that he was glad that I wasn't as annoying as I used to be. I wasn't too happy he said that, and refused to give him any that night. He wasn't too happy, but I kept reminding him that he needed to change if he wanted my body.

When my grandmother found out that I was sort of seeing him, she sat me down and had a long talk about being careful, especially if I was having sex with him. My grandmother was one of the first...hopefully the only besides the friends I had told...to know I was sexually active. She didn't care, saying that she would rather be do it in her house than some back alley.

Her and I had had many talks about Connor and his behavior over the years. She'd even called his dad a few times when things got really bad. She was concerned that he was taking advantage of me. I tried to convince her that I knew what I was doing, but I still had doubts in the back of my mind.

Connor surprised me right after the Fourth of July, when he asked if he could take me out on an actual date. My feelings towards him hadn't changed that much, and the memories of how he used to treat me were always in the back of my mind. With how good he was in bed, and lack of any other options, I told him yes, figuring if the date went bad, I could at least still get him to eat me out afterwards.

He picked me up from my grandmother's house in one of his dad's fancy sports cars and took me to Twenty Eight Atlantic, the only five-star restaurant in Cape Cod. I asked if he was trying to impress me with getting a reservation there and he just asked if it worked, making me laugh.

After we ordered our food, Connor again surprised me by asking if he could say something to me without me getting upset or potentially ruining the night. With a nervous knot in my stomach at what he might say, I told him yes.

He took a deep breath and a drink of his water before talking and something inside me said that this wasn't the same Connor I had known as a bully. "Look, first off, I want to apologize for how I've treated you since the day we first met. I was an idiot about it. You didn't deserve to be bullied and teased. As a guest and a neighbor, I should have been nicer and made sure you were having a good time and taken care of."

"Thank you, Connor. I did still have a good time here, but it would have been nice to have another friend," I told him, still kind of wondering where this was coming from.

"Saying that, I really have enjoyed getting to know you better this summer. I know that most of it has been..," he paused for a second, lowered his voice, and briefly looked around the restaurant before continuing. "Physical. But, watching you at work, and the little talks we've had, and just being around you more, I've come to realize that you're a beautiful, talented, and amazing young lady. One that I have come to consider being very lucky to be around."

He paused again, taking another drink, then said, "I know when this all started, you said that you were just looking for somebody to take care of you, a summer fling, if you will, and I'm just curious, what do I need to do to change your mind? Because I like you, Jackie, and I would like a chance to be more than just a summer fling."

Just as he finished talking, the waiter brought out our food and I was grateful for a chance to think about what he had said. After gathering my thoughts and taking a few bites of food, I said, "Connor, I do appreciate you apologizing and realizing what you had done wrong. But I can't lie and say that it fixes everything right away. Those memories, the things you did and said, are always in the back of my mind. I have enjoyed getting to know you a little better and I think I see a change in you."

Connor was nodding along, eating and listening intently as I talked, taking small breaks to chew my food. "So, I don't want you to take this the wrong way, because it doesn't matter to me at this point in my life who I hook up with. I mean, it does to a certain extent. I still want to have a little connection, at least a friendship with them, I guess. But, I'm not interested in a long term relationship."

Connor kept nodding, although I could see a little sadness in his eyes. I reached out for his hand with mine and I wrapped my fingers around his. "Look, Connor, I'm not going to sleep with anybody else while I'm here. Or go out on a date. If it makes you feel better, instead of calling it a summer fling, we can say summer boyfriend and girlfriend."

He laughed a little and said, "Even though you hate my guts?"

I laughed too and said, "After how many times and how enjoyable it is to have you rearrange my guts, I don't think I can hate yours anymore. And taking me here? This food is so good! You're quickly making up for all those years of mistreating me."

We finished our dinner while talking about our future goals and desires. As we walked out of the restaurant, we held hands, and Connor again surprised me when he took me home, and declined my invitation to come inside.

"Jackie, I know this may sound weird, but I don't want every date we go on or every time we hang out to come with an expectation of something sexual happening, as much as we both enjoy it. And I know that our time is limited before you go back to college, but I want to make our times count and mean something from now on. Are you OK with that?"

I told him that I was, despite the ache for his touch forming inside me. After giving him a kiss goodbye and thanking him for the date, I walked into my grandmother's house, shut the door, and leaned back against it, my insides buzzing.

This definitely wasn't the same Connor I'd known for years. Hell, he'd even changed from the first time we slept together and he was talking dirty.

Over the next month, things stayed about the same. Sleeping together when we could, going on dates, working together, and plenty of beach and ocean time as the water got warmer. The one thing that was changing, and I wasn't going to admit it, was how I felt about Connor. Whether it was helping a guest at the hotel, or helping my grandmother or his dad, or just being a stand-up gentleman while we were together, I was more and more impressed with him and wanted to be with him.

The first week of August, after making love on the beach in our little hidden spot, I finally confessed to Connor that my feelings were starting to change. I still didn't want a long term relationship, especially if it was going to be long distance, but I also didn't want him completely out of my life. He promised to make our last few weeks together before I went back to college, as amazing as he could.

And he did. I quit the job at the hotel so I could just relax the last few weeks, and Connor made sure that every second he was available, I was taken care of. Both in bed and out of it.

As our last day came, with me set to leave the next morning, Connor woke me up to take me out to breakfast, then spend the rest of the day either at the beach or shopping. That night, we went back to my grandmother's house, where we cooked dinner together. My grandmother had left a few days prior, going on her own little vacation, and Connor and I had greatly enjoyed having an empty house.

After dinner was cleaned up, I found Connor sitting on the couch in the living room. I straddled his lap, wrapping my arms around his neck, and leaning down to kiss him. He instantly put his hands on my hips as I started to roll them, grinding our groins together.

Connor slowly moved his arms around, moving down to my ass and grabbing my cheeks, holding tightly as I moved back and forth. I could feel his cock growing under the swimtrunks he still had on. He stopped kissing my lips and moved down to my neck as I tilted my head back, giving him full access to it.

As he kissed my neck, I shook my head, my blonde hair waving in the back. I pressed harder down on his groin, moaning as I felt his hard cock pressing against me. As Connor kissed lower down from my neck, going down to my chest, he moved his hands up, rubbing my back, going until he reached the bikini top I had been wearing all day.

The top was plain red and tied behind my back and around my neck. It pushed my breasts up a bit, and I had caught more guys than just Connor staring at my chest during the day. A few times, when we were alone, he had teased me a little, softly cupping my breasts and gently massaging them, always making me moan.

When his fingers reached the bikini, he pulled it apart, and I felt a release as they loosened around my breasts. With one hand, as he continued to kiss around my chest, he reached up and untied the bikini from my neck and let it fall between us while he brought his other hand around to my front and cupped my left breast, squeezing it as he kissed down to the right breast and began to lick around the nipple.

"Oh baby. Yes," I moaned as he nibbled on my nipple.

He kissed over to my left breast and sucked that nipple into his mouth as I scooted back a little on him, hooked my fingers into the hem of his swim trunks, and pulled them up and down, exposing his hard cock. I wrapped my hand around it and started to stroke his shaft as he continued to suck and lick my nipples.

"Maybe we should move to the bedroom," Connor suggested and I agreed with him.

We slowly stood up from the couch, my hand never leaving his cock, and walked over to the bedroom just down the hallway. Once there, before I could sit down on my bed, Connor hooked his fingers into the hem of the cut-off denim shorts I was wearing and started to pull them down.

As he did so, he knelt down on the floor and kissed my stomach. My bikini bottoms were quickly discarded, leaving me completely naked, and Connor kissing and licking around my clean-shaven pussy.

"Hmm...I need you baby," I moaned, grabbing onto Connor's head and lifting him up.

As he stood up, he again wrapped his arms around my waist, and kissed me as he lifted me up. I returned the kiss, pushing my tongue against his lips, and moaned as he sat me down on the bed. I quickly scooted back so my head could rest on the pillows, and watched as Connor stripped off his shirt.

As Connor climbed onto the bed, kissed me, and slid his hard cock into my pussy, I didn't want this night to end. Or the summer. Connor started to move back and forth, sliding his cock in and out, and I knew that I was going to miss it. I was going to miss him.

Maybe this was more than a summer fling?

"Oh my gosh! Oh my gosh! Do it! Finish in me!"

I was lying naked in my bed, with my summer boyfriend, Connor, sliding his cock in and out of me. This was probably the last time we would sleep together, as tomorrow I was driving back home to Springfield, Massachusetts, while he was staying in Cape Cod. It was only a two-hour drive, but being twenty years old, it felt like forever.

Connor leaned down, pressing his chest against mine as I wrapped my limbs around his body. I could feel him getting closer and closer, his breathing getting more and more shallow, his thrusts shorter and harder.

Two months ago, when I came out to stay with my grandma for the summer, just like I had every year of my life, I never would have thought this possible. I hated Connor. He was always the bully growing up and I couldn't stand the thought or sight of him.

He moaned into my ear that he was starting to cum and I felt his cock pushing deep into me. I pushed my hips up, letting out my own moan, feeling his cock fill me up.

Connor gave me a kiss that I eagerly returned as he rolled off me. I quickly grabbed a few tissues from next to my bed, handing him one and I used the other to clean myself up.

I rolled over after throwing the tissues away, landing in Connor's outstretched arm. As he wrapped it around me, he gave the top of my head a kiss and said, "I'm going to miss you, City Girl."

........

"Hey, City Girl. Been a while," I heard Connor say. It was the end of May and I had just arrived in Cape Cod, driving right from the campus of UMass Amherst, where I had just finished my sophomore year.

I had been coming to Cape Cod every summer to live with my grandmother for as long as I could remember. And for as long as I could remember, Connor was there to tease and bully me. And I hated it.

Connor was a year older, but I seemed to run into him everywhere I went. A country club, the beach, out to lunch or dinner, even on the few dates I went on as I got older. And he never failed to say something mean or rude. His dad was a high-level executive for one of the companies that operated off the docks in Cape Cod, and his large house was just a few houses down from my grandmother's.

The first few weeks, everything went pretty smoothly. I reconnected with the friends I had there, put in a few job applications, and spent some quality time with my grandmother. She had been wanting to teach me to cook for a while, and I was finally willing to accept her help. It was great. I even had a boy ask me out on a date.

Unfortunately, the date didn't go anywhere. Really unfortunately for me, because I was starting to feel pretty horny. I had a friend I had slept with right before leaving for Cape Cod, but I wasn't used to go longer than two weeks without any sex. And I didn't like it.

I was offered, and accepted a job working for a local hotel, working at their front desk. I was excited, not only because it was my first Big Girl job, but because they offered free pool and gym access to all of their employees, seasonal or full-time.

The one drawback to the job was that Connor worked there as well, doing maintenance. I just had to hope that the hotel would be big enough to avoid him and to keep reminding myself that he couldn't bully me while we worked.

I did have to work a few late night shifts, but I honestly didn't mind them. The other girls that worked it were all the same age as me and we were soon best friends, going out before or after work.

One of the nights that I wasn't going out with them, I stuck around the hotel, getting in a quick workout at the hotel's gym before putting on my swimsuit and cooling down in the pool.

After I finished in the pool, I went into the locker room, pulled off my swimsuit, and took a quick shower. When my shower was done, I toweled myself off and looked at myself in the full-length mirror.

I was twenty years old, but could easily pass for younger. My hair was a little messy, like it always was when I came to the coast, and falling past my shoulders in loose waves. It always got lighter in the summer, a blonde, almost golden in the sun, and never really sat how I wanted it to. Maybe one day I'd learn to do it.

I was starting to tan a little, a product of spending a little bit of time on the beach. Come August, it would really set in, and I was already thinking of ways and places I could tan nude. I was of middling height, neither tall nor short. With a mostly flat stomach and skinny legs and arms, the reasons why I was going to the gym as much as possible.

My chest was on the smaller side, but that didn't stop me from running my hands over my breasts and giving them a quick squeeze. Always had been. They fit me, but there was a time I wished I had my mom's chest.

I turned slightly in the mirror and glanced over my shoulder. I loved it when a guy grabbed my ass, even if there wasn't much there. Another reason to go to the gym.

As I turned back to fully face the mirror, I heard a sound behind me and looked up just as Connor turned the corner into the shower area.

"Connor! What the fuck!" I screamed as I dove for a towel and tried to hide my body. Connor jumped, scared by my yelling and ducked back behind the wall. I quickly moved back into a shower stall.

"Shit, sorry, Jackie, I didn't know you were in here," he stammered out.

"Oh really? But you didn't think to check? You make it a habit to just walk into a women's locker room?" I was seething, wishing he would just leave, unable to believe he caught me like this. He was never going to let me forget it. Hopefully he didn’t actually see anything that he would remember.

"I'm sorry, Jackie, I really am," he said and I actually think I believed him. "I was just told there was a broken shower head here and I figured that it was late enough, nobody would be in here."

I peeked my head out just as Connor did the same. I could instantly see the regret on his face and kinda felt sorry for yelling at him. "Hey, look, I'm...." as I started to apologize, I noticed his eyes going to the mirror and thought that he could see my reflection in it. "Are you trying to look at me naked?"

Connor shook his head and tried to stammer out something else but I shushed him and said, "Do you like what you see?"

I briefly thought about stepping out, letting him see me naked, and could even feel myself already getting turned on. When he shyly answered yes, I said, "Good. Now get out so I can get dressed."

Later that night, I was still turned on. As I lay in my bed, I brought my hand down to my groin, pulled my pajama shorts down, and started to touch myself. I closed my eyes, images flashing through my mind, mostly of Connor, both surprising me, and leaving me turned on. It wasn't the same as what a guy could do to me, but I still got myself off, feeling some relief.

But from Connor?

The next few shifts that I worked, Connor actually sought me out, making sure to apologize every time he did so. He was actually being nice to me and I wasn't sure if it was because he didn't want me to get him in trouble, or his mindset had changed after seeing me naked.

A week and a half after my shower run in with Connor, I was again working the front desk, but this time by myself. Connor came up to check on me a few hours before the shift ended, just as a panicked call from a guest came in.

"Ok. OK. I understand. My maintenance is right here and I have another room available. I'll bring him right over and I'll take you to your new room," I said, hoping I was doing the right thing.

I looked up at Connor as I hung up the phone and said, "Room 203 says their bathroom is flooding. Something about the shower being stuck. I have a vacant room I can put them in while you fix it."

"Let's go," Connor said as I put a sign up letting anybody know that I would be back and grabbing the vacate room's key.

We quickly made our way to the room that was flooding and knocked on the door. Connor went right in and immediately to the bathroom, while I escorted the guest out of the room, helping to grab their belongings.

After making sure that the guest was taken care of, I went back to room 203, seeing if Connor needed any help.

"Hey, Connor? You doing OK? Anything I could do to help?" I called out, no longer hearing any water flowing.

"Ummm...towels? If housekeeping is here, can you get them to bring up a lot of towels?" I heard him answer me from the bathroom.

I knew that housekeeping had already left, so after quickly checking the front desk, I quickly walked to where the towels were kept, grabbed as many as I could fit on a cart, and went back up to Connor. He wasn't in the room when I came back, but there was still water on the floor, so I started to lay down the towels to soak it up.

"Oh, thanks, Jackie. You didn't have to do that," Connor said a few minutes later, coming back into the room with a toolbox in his hand.

"No worries. Wanted to help," I told him.

He helped me to soak up the water, both of us getting wet in the process. There were a few times where our hands accidentally touched and we would make eye contact, both of us quickly looking away.

When we were done, we sat back on the floor, our backs against the wall, breathing deeply.

"You look confused," Connor said a minute later, looking over at me.

I was. I was turned on. So turned on. And it was just from being around him and our brief touches. But why?

I took a big breath and shook my head, trying to clear my thoughts.

"Not used to hard work?" Connor said and I couldn't tell if he was joking or not.

Being alone in a room with him, I finally decided to give him a taste of his own medicine.

"Why are you always so mean to me? Are we still in elementary school? You being mean to a girl cause you like her?"

Now it was Connor's turn to look confused. "Shouldn't you go back to the front desk? Don't want a guest walking in with nobody there."

"Don't deflect. I know you were checking me out in the locker room. You probably went home and jacked off to what you saw, didn't you?" I continued to tease him, still feeling the warmth in my groin.

"I...umm...I...what the fuck are you talking about?"

I stood up off the floor, smiling down at him. "Don't worry. You can admit it. I will. I went home that night and enjoyed myself."

Before he could process what I said, I turned and walked out of the room, making sure to put one foot in front of the other, making my ass sway as I walked away.

I wasn't sure what my game plan was as I walked away. Did I want Connor? Part of me said yes and another part remembered how much I hated him. But, seeing him confused and speechless made him kind of cute.

A few seconds later, I heard him call my name, and turned to see him jogging to catch up to me.

"What was that about?" he asked as he stopped a few feet from me.

I shrugged and then turned away again, quickly walking to a door leading to a stairwell. Connor was right on my heels and when I felt him reaching for me, I turned again to face him, smacking his hand away. "Look, Connor, I don't know! You've always been so mean to me! I hate you. I don't know why, but every year that I'm here, for just a few months of the year, you seem to make it your life's mission to make my life hell. And now, now you want me to explain myself to you? No! You explain yourself. Now."

"I..." Connor started, taking a step back and leaning up against the door.

"You what?" I said, folding my arms against my chest. When he didn't immediately respond, I said, "I need to get back to the desk. I don't have time for this."

As I tried to walk away, Connor reached out and grabbed my arm, stopping me in my tracks. "Look, Jackie, this isn't easy for me. At first, yeah, I was just being mean to you because I was young, dumb, and that's how we treated new people. Summer people. City girls. And then as we got older, it was just a habit. I never gave you a chance. And I'm sorry for it."

"So, what changed? Me working here? Seeing me naked? Maybe hoping it would lead to something else?" As I talked, I watched Connor looking my body up and down and I knew what he wanted. Before he could respond, I laughed, and said, "That's what I thought."

I immediately turned and walked down to the first floor. Thinking the entire time, that I wanted the same thing.

An hour before my shift ended, I used the desk phone to call maintenance. When Connor answered, I said, "After we're off, meet me at the beach. You know the spot. Bye." I hung up the phone before he could respond and could feel the familiar warmth in my groin as I smiled to myself.

I pulled into the beach parking lot a short time later and reached into the backseat of my car to grab a bag I kept there. My hotel uniform was simple and modest, and I quickly pulled my blouse out of my slacks and started to unbutton it. I had a white tank top under it and briefly debated on pulling on a sweatshirt. It was sixty degrees but felt a lot cooler next to the ocean.

I pulled a towel and my beach sandals out of the bag, stuffed my work blouse into it, and opened the car door. I changed my shoes before shutting the door and walking to where I hoped Connor would meet me.

I didn't have to wait very long as I heard his car pull up and him walking up to the little private area that everybody knew about but nobody would admit to it. "Hi," we both said simply.

We both stood there awkwardly, staring at each other. I don't think I had ever actually been alone with Connor, besides tonight at work. But, out on the beach, hearing the waves crashing onto the rocks that were nearby, all the memories of how he treated me came flooding back.

Connor broke our gaze first, looking off to the side, and I wondered if he was having the same feelings. He looked different, somehow, almost seeming like he wanted to act one way, but knew he shouldn't. Or couldn't.

I wasn't sure what to feel. I still didn't like Connor. Too many years of him being a bully. But the way he looked at me...our brief, accidental touches...my own horniness...maybe, just maybe this was right.

When he looked back at me, I made a decision. I was going to do this. But on my terms.

I had laid the towel down on the sand and saw him glance at it. "Look, Connor. I don't know what's going on between us. But, I feel an attraction. And I need it. I don't want anything permanent or long term or even short term. I just want to be taken care of this summer. I want somebody reliable and good. Can you do that for me?"

Connor nodded his head and I saw him looking at my body again, pausing at my chest. In the cool night, with a soft breeze blowing from the ocean, my nipples had hardened almost instantly, poking out through my bra and tank top.

I took a few steps towards him and looked up. Connor was a few inches taller than me, with sandy blonde hair that he kept cut pretty short. I wrapped my arms around his neck and pulled him down to kiss me.

Connor kept his eyes open, staring at me, and for a moment, I was wondering if I was his first kiss. But then, he grabbed onto my hips and returned the kiss with a fiery passion, one that told me that all of my assumptions lately were correct.

As we made out, our heads twisting and turning, our lips never leaving each other, I moved my hands down to his groin and started to undo the buttons holding up his jeans. As I pulled apart his jeans, I slipped my hand inside them, moaning into his mouth as I started to rub his cock.

I was pleasantly surprised to find that his cock fit into my hand perfectly. It wasn't too big or too small...it was comfortable. As I ended the kiss and started to drop into a squat position, I pulled his pants and boxers down, letting his cock bounce free, and smiling as I saw it.

"You like that, don't you baby? Nice and thick, ain't it?" Connor said as I stroked his cock with my hand.

I laughed a little at his dumb comment and wondering if he was being serious. I stuck out my tongue and licked around his tip for a minute as Connor put one of his hands on the back of my head, trying to guide me more to his cock.

As I wrapped my lips around his shaft and started to bob my head up and down, while still using my hand on him, Connor reached down, roughly grabbing at my breast through my tank top and squeezing it.

"Your tits aren't very big, but fuck are they nice to grab," he said, slipping his hand inside my tank top and bra.

I took him out of my mouth, keeping my hand going on his shaft, and said, "If you want to fuck me, you better stop talking."

I started to lay down on the towel, pulling my slacks and underwear down and off my feet. Connor was right there, kissing all over my neck and chest, and using his hand to pull my tank top and bra up. I reached down between us and guided his cock into my pussy as he licked my nipples, moving back and forth between the two.

I had to put my hands on his butt and wrap my legs around his in order to encourage him to push inside me, letting out a moan as his cock filled my pussy. Connor had his hands on the towel to support himself as he continued to kiss and lick my nipples.

"For them being small, you sure do seem to enjoy them," I teased him as he slowly started to move back and forth, sliding his cock in and out of me.

"Should I stop?" he asked, looking up at me.

"No," I said. "But you can go a little harder."

Connor did stop kissing my breasts, instead focusing on slamming his cock into me, hard and fast. I closed my eyes, enjoying the feeling of once again having a man inside me. It had been far too long.

I kept my legs wrapped around his waist, feeling them moving as he moved. I moved my hands off his butt, going up and over his back, rubbing with my fingers as I went.

"Am I allowed to say how hot you are?" he asked as he went into me over and over.

"Yes," I breathed out, in between moans.

"You're so fucking hot," he said. "I'm going to cum. Do I need to pull out?"

"No," I said, wrapping my legs tighter around him.

Connor continued to slam into me, his waist pinning me to the towel as he went as hard as he could. His grunts and groans started to get louder until he finally pushed as deep into me as he could, and started to orgasm. I kept my legs wrapped around him as his cock shot his cum into me.

"Oh yes. God yes," I moaned before Connor leaned down and kissed me.

When he was done with his orgasm, he slowly pulled out and I felt empty again as his cock left me.

"I can't believe that just happened," he said as he rolled over, laying down next to me.

I couldn't either, I thought to myself as I lay on the towel, nearly completely naked, having just been fucked by a guy I hated. Or thought I did.

The next couple of weeks, Connor and I didn't talk too much. But, we spent a lot of time together. If we worked a day shift together, we often snuck off somewhere, usually during our lunch times, often making out in his car, and always ending with a blowjob. When we worked nights, the beach became our favorite spot. And, the few days that we both had off, it was either his dad's house or my grandma's house, but always in a bed, and always ending with us both satisfied.

We did have a few instances where I thought that Connor was the same old mean Connor. Certain words or phrases would slip out. Especially when I was giving him oral. He told me one day while we were at work that he was glad that I wasn't as annoying as I used to be. I wasn't too happy he said that, and refused to give him any that night. He wasn't too happy, but I kept reminding him that he needed to change if he wanted my body.

When my grandmother found out that I was sort of seeing him, she sat me down and had a long talk about being careful, especially if I was having sex with him. My grandmother was one of the first...hopefully the only besides the friends I had told...to know I was sexually active. She didn't care, saying that she would rather be do it in her house than some back alley.

Her and I had had many talks about Connor and his behavior over the years. She'd even called his dad a few times when things got really bad. She was concerned that he was taking advantage of me. I tried to convince her that I knew what I was doing, but I still had doubts in the back of my mind.

Connor surprised me right after the Fourth of July, when he asked if he could take me out on an actual date. My feelings towards him hadn't changed that much, and the memories of how he used to treat me were always in the back of my mind. With how good he was in bed, and lack of any other options, I told him yes, figuring if the date went bad, I could at least still get him to eat me out afterwards.

He picked me up from my grandmother's house in one of his dad's fancy sports cars and took me to Twenty Eight Atlantic, the only five-star restaurant in Cape Cod. I asked if he was trying to impress me with getting a reservation there and he just asked if it worked, making me laugh.

After we ordered our food, Connor again surprised me by asking if he could say something to me without me getting upset or potentially ruining the night. With a nervous knot in my stomach at what he might say, I told him yes.

He took a deep breath and a drink of his water before talking and something inside me said that this wasn't the same Connor I had known as a bully. "Look, first off, I want to apologize for how I've treated you since the day we first met. I was an idiot about it. You didn't deserve to be bullied and teased. As a guest and a neighbor, I should have been nicer and made sure you were having a good time and taken care of."

"Thank you, Connor. I did still have a good time here, but it would have been nice to have another friend," I told him, still kind of wondering where this was coming from.

"Saying that, I really have enjoyed getting to know you better this summer. I know that most of it has been..," he paused for a second, lowered his voice, and briefly looked around the restaurant before continuing. "Physical. But, watching you at work, and the little talks we've had, and just being around you more, I've come to realize that you're a beautiful, talented, and amazing young lady. One that I have come to consider being very lucky to be around."

He paused again, taking another drink, then said, "I know when this all started, you said that you were just looking for somebody to take care of you, a summer fling, if you will, and I'm just curious, what do I need to do to change your mind? Because I like you, Jackie, and I would like a chance to be more than just a summer fling."

Just as he finished talking, the waiter brought out our food and I was grateful for a chance to think about what he had said. After gathering my thoughts and taking a few bites of food, I said, "Connor, I do appreciate you apologizing and realizing what you had done wrong. But I can't lie and say that it fixes everything right away. Those memories, the things you did and said, are always in the back of my mind. I have enjoyed getting to know you a little better and I think I see a change in you."

Connor was nodding along, eating and listening intently as I talked, taking small breaks to chew my food. "So, I don't want you to take this the wrong way, because it doesn't matter to me at this point in my life who I hook up with. I mean, it does to a certain extent. I still want to have a little connection, at least a friendship with them, I guess. But, I'm not interested in a long term relationship."

Connor kept nodding, although I could see a little sadness in his eyes. I reached out for his hand with mine and I wrapped my fingers around his. "Look, Connor, I'm not going to sleep with anybody else while I'm here. Or go out on a date. If it makes you feel better, instead of calling it a summer fling, we can say summer boyfriend and girlfriend."

He laughed a little and said, "Even though you hate my guts?"

I laughed too and said, "After how many times and how enjoyable it is to have you rearrange my guts, I don't think I can hate yours anymore. And taking me here? This food is so good! You're quickly making up for all those years of mistreating me."

We finished our dinner while talking about our future goals and desires. As we walked out of the restaurant, we held hands, and Connor again surprised me when he took me home, and declined my invitation to come inside.

"Jackie, I know this may sound weird, but I don't want every date we go on or every time we hang out to come with an expectation of something sexual happening, as much as we both enjoy it. And I know that our time is limited before you go back to college, but I want to make our times count and mean something from now on. Are you OK with that?"

I told him that I was, despite the ache for his touch forming inside me. After giving him a kiss goodbye and thanking him for the date, I walked into my grandmother's house, shut the door, and leaned back against it, my insides buzzing.

This definitely wasn't the same Connor I'd known for years. Hell, he'd even changed from the first time we slept together and he was talking dirty.

Over the next month, things stayed about the same. Sleeping together when we could, going on dates, working together, and plenty of beach and ocean time as the water got warmer. The one thing that was changing, and I wasn't going to admit it, was how I felt about Connor. Whether it was helping a guest at the hotel, or helping my grandmother or his dad, or just being a stand-up gentleman while we were together, I was more and more impressed with him and wanted to be with him.

The first week of August, after making love on the beach in our little hidden spot, I finally confessed to Connor that my feelings were starting to change. I still didn't want a long term relationship, especially if it was going to be long distance, but I also didn't want him completely out of my life. He promised to make our last few weeks together before I went back to college, as amazing as he could.

And he did. I quit the job at the hotel so I could just relax the last few weeks, and Connor made sure that every second he was available, I was taken care of. Both in bed and out of it.

As our last day came, with me set to leave the next morning, Connor woke me up to take me out to breakfast, then spend the rest of the day either at the beach or shopping. That night, we went back to my grandmother's house, where we cooked dinner together. My grandmother had left a few days prior, going on her own little vacation, and Connor and I had greatly enjoyed having an empty house.

After dinner was cleaned up, I found Connor sitting on the couch in the living room. I straddled his lap, wrapping my arms around his neck, and leaning down to kiss him. He instantly put his hands on my hips as I started to roll them, grinding our groins together.

Connor slowly moved his arms around, moving down to my ass and grabbing my cheeks, holding tightly as I moved back and forth. I could feel his cock growing under the swimtrunks he still had on. He stopped kissing my lips and moved down to my neck as I tilted my head back, giving him full access to it.

As he kissed my neck, I shook my head, my blonde hair waving in the back. I pressed harder down on his groin, moaning as I felt his hard cock pressing against me. As Connor kissed lower down from my neck, going down to my chest, he moved his hands up, rubbing my back, going until he reached the bikini top I had been wearing all day.

The top was plain red and tied behind my back and around my neck. It pushed my breasts up a bit, and I had caught more guys than just Connor staring at my chest during the day. A few times, when we were alone, he had teased me a little, softly cupping my breasts and gently massaging them, always making me moan.

When his fingers reached the bikini, he pulled it apart, and I felt a release as they loosened around my breasts. With one hand, as he continued to kiss around my chest, he reached up and untied the bikini from my neck and let it fall between us while he brought his other hand around to my front and cupped my left breast, squeezing it as he kissed down to the right breast and began to lick around the nipple.

"Oh baby. Yes," I moaned as he nibbled on my nipple.

He kissed over to my left breast and sucked that nipple into his mouth as I scooted back a little on him, hooked my fingers into the hem of his swim trunks, and pulled them up and down, exposing his hard cock. I wrapped my hand around it and started to stroke his shaft as he continued to suck and lick my nipples.

"Maybe we should move to the bedroom," Connor suggested and I agreed with him.

We slowly stood up from the couch, my hand never leaving his cock, and walked over to the bedroom just down the hallway. Once there, before I could sit down on my bed, Connor hooked his fingers into the hem of the cut-off denim shorts I was wearing and started to pull them down.

As he did so, he knelt down on the floor and kissed my stomach. My bikini bottoms were quickly discarded, leaving me completely naked, and Connor kissing and licking around my clean-shaven pussy.

"Hmm...I need you baby," I moaned, grabbing onto Connor's head and lifting him up.

As he stood up, he again wrapped his arms around my waist, and kissed me as he lifted me up. I returned the kiss, pushing my tongue against his lips, and moaned as he sat me down on the bed. I quickly scooted back so my head could rest on the pillows, and watched as Connor stripped off his shirt.

As Connor climbed onto the bed, kissed me, and slid his hard cock into my pussy, I didn't want this night to end. Or the summer. Connor started to move back and forth, sliding his cock in and out, and I knew that I was going to miss it. I was going to miss him.

Maybe this was more than a summer fling?