u/new_erotic_writer

I never thought I’d be writing this, but here we are.

I’m Thomas, 20 years old, taking about a year break from college for accounting and taking a temp job doing data-entry at a big corporate office. I’m not much of a social person so sitting at a desk and entering receipts and expenses suits me. No one bothers the new temp guy and my job is boring. I’m good with it.

I’m an introvert by nature and never had a girlfriend or been on many dates. I never had anyone really to show me how to talk to women and frankly the women my age bore me. My dad died before I was born, my mother didn’t really raise me and I had to kind of figure things out on my own. I’ll get into that later, but suffice to say, I’m pretty independent, keep to myself and take care of myself. I had to learn that lesson really young because I’ve never really had anyone to care for me. I’m a pretty unassuming dude. I’m not tall, around 5 foot 10 and skinny fit. I have muscle tone from being a swimmer in high school and keep up a little in college. My dorm roommate calls me a twink. I’m not a fan of the term because I can still handle myself from doing mixed martial arts the last 6 years.

With college boring me, I decided to take a year off and immediately got a temp job. I interviewed with and started working directly under Ms. Veronica Hale, the executive assistant to the CFO of the company. From what I see, Ms. Hale basically runs the place, even as an admin. And yeah, things have gotten interesting with her. This is Part 1 of many. I have a lot to talk about of what has transpired, and is still transpiring. I’ll post the rest as we go, because trust me, there is a lot and I have a didactic memory, it’s slow at first but like this story, she took her time grooming me and it gets hotter as we go. I have been and still am experiencing every young man’s wet dream. Long story short, in the last year since I got hired, Ms. Hale has been grooming me to take my virginity and be my first, amongst other plans she has for me.

Ms. Hale is… God, where do I even start? Don’t judge me, She’s 49, divorced, but she’s the kind of woman who walks into a room and every single executive straightens up like she’s the one signing their checks. All the other admins, even the CEO’s respect her she commands the respect and dignity of everyone in the officer. It probably doesn’t hurt that she’s tall. She’s 6 foot 1 in bare feet, and with the heels she wears every day she’s towering over most of the guys in the company, including our CEO. She is graceful and elegant, sensual and graceful. She has dark auburn hair with large steaks of silver mixed in that she wears like a badge of honor. Milky-white skin, these piercing green eyes behind thin frame glasses that somehow make her look even more commanding. And her face? Soft and pleasant but beautiful and still young looking. Perfectly aged, She reminds me of a younger Lynda Carter — strong jaw, warm smile, but with this confident edge that says she fought for every inch of respect in a man’s world and won. She’s of Greek descent, and like the house, cars and her ex husband’s pension, she kept her ex husband’s last name as well just to remind him that she can take and keep everything from him for what he did to her. The business skirts she wears hug her mature but elegant hips just enough to remind you she’s all woman. Button-up blouses that strain ever so slightly over what I swear are full C’s tipping into D’s. She smells like light floral perfume and coconut shampoo, subtle, but you only notice it when she’s close. And she gets close.

I was nervous my first week. Fresh on my break from college, no real office experience, just trying not to screw up spreadsheets and let people down. I figured the less I screw up the less unwanted attention I would draw to myself. But Ms. Hale took me under her wing immediately. Protective. Warm. Nurturing. Maternal in nature almost but with sensual undertones. Her attention I didn’t mind, at times, craved. She would always ask me how I was doing, how my weekend was, how my dorm was and if I was eating and getting along in the office ok. Even though I rarely ever screwed up, she loved to come to my desk to check my work. She likes accuracy and she says that leads to efficiency. She’d always come to my cubicle from behind me and lean forward and over my shoulder and desk to check my work like she was trying to see the screen better, one hand always resting on my shoulder, her left breast brushing right against the side of my neck while she pointed at the screen. I don’t know if she noticed it. It always looked accidental, like she was just focused on the numbers. But if I turned my head even an inch, my nose would’ve been buried in soft, warm, side boob. I could see her bra strap and cleavage in the reflection of my computer screen when she did this. Her breath always smelled nice and would tickle my ear when she whispered instructions: “Good progress on that dataset, Thomas. You are really getting this down, I’m proud of you, Keep it up, honey.” The way her voice dropped low, warm and understanding, her voice kind of like Mary Steenburgen narrating your best dream, it sent shivers down my spine every single time. I looked forward to it everyday. At first I thought calling me honey might have been unprofessional but where she comes from, that’s just part of her lexicon I thought. I mean, she says that to everyone so I never really paid it any thought.

Six months of that from day one and as time passed conversations got longer, deeper. Everyday While I was entering data, she would stand behind me and give me helpful instructions on excel, She’d run her fingers through the hair at the back of my neck while talking. She said she used to be a hairstylist before climbing the corporate ladder. “You know, Thomas, I’d give you a nice trim right here,” she’d murmur, nails grazing my scalp. I’d let it grow out just because I liked hearing her say it, or maybe I just liked her touching my scalp. She was always bubbly and kind. I didn’t ever take it as flirting, but I wasn’t upset about it either. I never really got affection or attention from anyone, so even being touched and having my hair played with was nice. The girls in the office would flirt at my desk, casual stuff, nothing crazy, but Ms. Hale would loudly but gently say from her office, “Thomas, Need those Q3 numbers ASAP, please.” I’d look up and catch her watching from her glass office, that little smile playing on her lips. The office gals would leave in a hurry, they were scared of her. I wonder if maybe she was jealous? Nah, of what? A 20 year old more than half her age? But protective? Definitely. I’ve never had anyone be protective of me, care about who I was talking to. I’d always smile, “yes ma’am getting those to you right now”

One afternoon she asked, casual as anything, “You have a girlfriend, Thomas?” I was at my desk. She was perched on the edge, legs crossed, heel dangling, sitting over the top of me. I looked up and laughed nervously. “No, why?” She tilted her head, green eyes sparkling behind those glasses, slight grin. “I just assumed. You know, you’re a catch for girls your age and for some here in the office.” Then she leaned in closer, voice dropping to that professional whisper that always made the hairs on my neck stand up. “Actually…and I’m sure you have noticed, I’ve been chasing a few of them away from your cubicle on purpose. Thought I was protecting your relationship. I just assumed you had a girlfriend, that and keeping HR off your back. Some of these girls flirt hard, then cry to HR if they don’t get what they want.” I blinked, heart thumping. “Thank you… seriously.” She smiled, warm and knowing. “So if you don’t mind me asking Thomas, why don’t you have one? Handsome sweet, quiet boy like you, full head of hair, focused, in shape…” I shrugged, cheeks burning. “School, I guess. Maybe I’m too quiet. Never really dated. Wouldn’t even know how to flirt.” Her expression shifted, amused, almost predatory in the softest way. “That explains things,” she said, and sauntered back to her desk like she hadn’t just lit a fuse. I whispered “what the fuck was that” to myself and shook my head. I needed to shake it off. She’s just a caring boss looking out for me. I can’t be thinking she wouldn’t even be remotely interested in me, she’s to respectable in the office, she’s more than twice my age, and they would cook her alive is she fucked around with me. I’m a fucking temp.

But, after that, I felt like things were different now that she knew I was single, I mean she probably even figures I’m still a virgin. I started to notice that she stood even closer to me. A lot closer. Hands on my shoulder lingered. Breast against my shoulders when standing behind me giving me instructions. Brushes with her side boob looking at my screen felt deliberate. I told myself older women just don’t care about personal space. But, I wasn’t complaining. I felt good around her, confident, seen, care for, looked after, protected and weirdly loved. She’d say things like, “You’re doing so well, Thomas. I appreciate you, you are my favorite temp, don’t tell the others,” in this genuine, nurturing tone that made me want to earn every word. “I’m your only temp ma’am” “mhm I know honey, I like it that way, I can focus all my attention where it deserves to be.” She patted me on the shoulder, squeezed and walked back to her office. Her words right then gave me a wave of warmth and excitement over my body. I’d go back to my dorm rock-hard most nights, replaying the way her nails felt on my neck, her words of encouragement and kindness. I almost felt like a puppy on a leash that lived for her affection, scratches, and head pats, I was weirdly aroused in a way I couldn’t explain.

Then came the day everything tilted.

She was checking my work again, leaning in extra close, that coconut scent wrapping around me. In the computer reflection I could see down her shirt again, it was a low cut black dress top with spaghetti straps and is to be worn under an office jacket, she was wearing a dark blue strapless lace bra that just poked out. I wonder if she could ever see the angle of my eyes on the computer screen looking down her shirt. I didn’t try to but it was so tempting. Her fingers trailed through my hair again, light this time. I shuddered hard, eyes fluttering. “Oh, honey, sorry, did I tickle you?” she asked, her voice soft with concern. “It’s okay,” I managed. She smiled, then dragged her nails firmly down the back of my head and neck. My whole body went limp. Eyes rolled back. A low, involuntary sound slipped out of me. I’d never felt anything like it, pure, melting pleasure.

“Oh I’m sorry, did I hurt you honey?” she whispered, pulling back just enough for me to see her green eyes searching mine. But there was something else there, curious, in control. “No, ma’am,” I breathed. “I’ve never had anyone touch me like that.” She arched a perfect brow, playful but warning. “Touch you like what? Careful with your words around the office, sweetie.” I backpedaled fast, face hot. “I mean… scratching my head. It felt… nice.” She let out a soft laugh. “Huh! Well, I’m glad I didn’t hurt you. Finish that dataset, it’s your six-month review time. We’re doing lunch. My treat.” She paused at my cubicle wall on the way back to her office, towering over me even more in those heels. “Thomas, meet me at my car in the parking garage at 1:00. I’ll be in a meeting, so grab my keys from my desk, go start it up, get the AC going. It’s hot out side today, I don’t want to sweat in my car after having to walk a quarter mile to the parking garage.” I nodded. “Will do… ma’am.” Her lips curved. “That’s a few times now that you have said ma’am, interesting. Hmm. I think I could get used to that. See you at one.”

By 12:45 I was at her desk. Keys right there. I could see her through the glass conference room with her boss the CFO and the CEO, notepad in hand, commanding the CEO’s attention like she owned the damn company. She glanced my way, checked her watch, gave me a nod. I rushed to the garage and found her black Jaguar F-Pace with blacked out tinted windows. I opened the door and it smelled like her perfume inside. The car was beer, tidy and clean like it had been derailed. I started it, cranked the AC, went around to the passenger side, opened the door… and froze.

Panties. Blue lace, matching the bra I’d glimpsed earlier today, right on the floor mat. I noticed a gym bag cracked open in the back. My brain short-circuited. Pick them up and throw them in there quick? Leave them? Images of her, tall, confident, slipping them off after a workout, flooded me uninvited. I didn’t know what to do. Last thing I wanted was for her to walk up with her panties in my hand and look like a pervert.

High heels clicked closer and closer. Driver door opened. She slid in, all 6 foot 1 of her in that skirt and blouse, and saw my red face. Then her eyes dropped to the panties. A husky laugh rolled out, the first time I’d ever heard her swear. “Oh, fuck! hahahaha — bet you’re scared shitless right now, aren’t you, baby?” She never called me baby at work. Never swore. My pulse hammered. “It’s okay. I’m sure you’ll see plenty more in your life Thomas. Just toss them in the gym bag for me if you don’t mind.”

I couldn’t move. She smiled and leaned across the console, low cut shirt gaping just enough that I got a full view, deep cleavage, the edge of that matching bra, the soft swell of her breast. Did she forget to put them back on after the gym? Was I supposed to see those? The whole care is clean but panties were left out? The thought made my mouth dry and heart pound. “It’s ok baby, here” She grabbed them herself, tossed them back, then patted the leather seat beside her. “Sit, honey. We don’t have long for lunch around here.” As she pulled out, she explained the spot she picked, quiet, away from the office snakes and their rumors. “People in the office talk, especially if it’s a senior employee out to lunch with a temp and two of the biggest gossiping girls have crushes on you, by the way. That’s why I keep you at your desk. Don’t need them stirring shit.”

“Wait… two?” I asked, voice cracking.

She glanced over, green eyes warm but sharp. “Maybe more…honey, you’re young, innocent, cute, skinny and good hair. You are a breath of fresh air to the office girls. Compared to the balding slobs around here? The ladies room has been buzzing about you. Women aren’t that different from men when it comes to office talk… and some are absolute whores about it.” She reached over gently and squeezed my knee, quick and reassuring. “That’s also why I can be so overbearing. I need your work done, and I need you safe. You do really good work and I want to keep you around as long as I can Thomas, you are special to me and I don’t want to lose you over some bullshit”

I swallowed. “Thank you.” I felt wanted, and I felt weird for a second. “You’re always looking out for me. No one’s ever done that.” The words just spilled out with vulnerability I didn’t mean to show. It kind of felt nice to be able to trust someone. “Oh really? What about your mom?” I looked at her and paused for a second. She looked back with genuine curiosity and concern. Fuck it, I’ve already opened my mouth. “Well, my mom wasn’t around much. Dad died before I was born. I basically raised myself, babysitters, then home alone. She’d come back late, go on dates, leave me with pizza. I got good at being independent, I never socialized or even had friends, and girls? Forget about it.” “Awe baby I’m so sorry to hear that. Thank you for being vulnerable with me, that tells me a lot about you.”

We pulled into the quiet little bistro parking lot. Lunch crowd thinning out. Ms. Hale parked, turned to me with a maternal -soft, boss-lady smile. Her hand found my thigh again, higher this time, rubbing up and down and giving a gentle, possessive squeeze. “So there’s been no one to hug you, be proud of you, praise you, show you real affection? No wonder you melted under my fingers earlier. You poor thing.” Her voice dropped, nurturing and low, breath warm against my ear as she leaned in slightly. “But maybe it’s a good thing. You’re mature. Strong. Emotionally steady. And now, the good news is you have someone like me who does see you. Someone who knows exactly how girls think… and how to guide a sweet boy like you.” “Haha you have been really nice and caring to me and I appreciate you ma’am.”

She killed the engine, eyes locking on mine behind those glasses. “Come on. Let’s get inside. I want to hear more about what you need, Thomas. And maybe… mentor you on a few things. Work, office politics, relationships, women, maybe teach you a few things personally…”

What? My chest tightened with that mix of anxiety and excitement I was starting to crave. Lunch was just beginning… and I had no idea how far this “mentorship” was about to go.

*part two is written, let me know if you want more. If not I’ll keep this adventure to myself.*