u/KJ_013

Well, one thing is for certain. At this point I could no longer say "I don't cheat." Any semblance of that was washed away with the moans as Alice came down from her second orgasm. If you're wondering how I got here then it's your own fault for not reading part one and two.

Me, 6'2" cauasian, with short dirty blond hair combed over in that generic white guy hair style, 175 pounds that I work hard to keep in shape, I've been told I look like Mathew Gray Gubler's younger, less attractive, about-as-awkward-as-criminal-minds-ass brother. With a slightly above average dick, that's decently above average thick.

Her, Alice, 5'8" hispanic, and while she was active and healthy she had more of a 'normal' body type. Long dark brown curly hair, and beautiful brown eyes that always made me think of Cleopatra. She was as elegant as a queen to me, and my childhood crush who grew into a D set of titties and an ass-tronaught. (It was and is out of this world.)

Somewhere else, my girlfriend was probably in bed, watching a movie, blissfully unaware of the my blissful pretending she didn't exist.

As Alice came down from her second orgasm that night I flipped her over, lifting her ass up, kneading it with my hands enjoying being able to touch what I had dreamed about for years. Some of you might be wondering, Jay, you haven't mentioned a condom, weren't you worried about pregnancy? Remember how I said she was my best friend and we talked about everything? That included her telling me about her shitty experience getting an IUD, which was accompanied with a rant about how the healthcare system hates women. (Honestly, why the fuck is anesthesia not an option for that? Someone make it make sense.) I grinned as I brought my hips into hers eliciting another moan as my raw cock filled her wet willing pussy and continued pounding away. Doggy isn't my favorite position, but there's something so satisfying and powerful feeling about it, and it treats my dick right. She moaned again bringing me back to the moment as I continued to fuck her, the tempo of our skin creating a "clap clap clap" that I'm sure the neighbors could hear. I didn't care. Let them hear. Tonight I was cheating on my girlfriend, I was fucking my best friend and childhood crush, tomorrow would come with tomorrows problems, but for tonight I was going to fuck like a man with no regrets.

After a couple more minutes of that she asked if we could switch position, and doggy is tiring, so I sat back down on the couch and she climbed on top of me. Looking me in the eye, as I felt her sink down, down, til she was in my lap, and I was in her. She wrapped her arms around my neck and I saw a spark in her eye that I hadn't seen that week. Maybe it was happiness? Maybe hope? I couldn't examine it for long as she leaned in and our tongues entwined. I reached a hand up to grab a boob while my other hand stroked her ass as she began riding me. Slow and steady, enjoying the closeness. After a couple minutes I felt her breathing begin to rise again. It matched her increased tempo as she started riding faster, and faster. There was a neediness as I felt her sliding up and down my cock. I felt myself building too. I had been performing well, and the alcohol did a great job of letting me last as long as I did but no man lasts forever. She changed the angle of her hips slightly so when she came down she could grind her clit against my pubic bone, and something about that angle did it. "Alice" I gasped out. "I'm going to cum."

She immediately hopped off my dick and got back on her knees in front of me, hand and mouth working in tandem to bring me over the edge as rope after rope covered the back of her throat, and then when the orgasm subsided she let my cock fall out of her mouth with a soft pop.

But I wasn't done. My dick was still semi hard, and I grabbed her hair and pulled her back to her duty, my cock re-entered her mouth as a laugh was cut off by cock and she continued to worship my erection, bringing life back to the fading member. I don't know how, but I never got past half chub before I was hard again. Hard and maybe a little bit angry. Angry at myself, angry at Alice for making me do this, but mostly angry at my girlfriend, for having the audacity to exist prevent me from enjoying this with reckless abandon. I grabbed handfuls of Alice's hair and began to pull her deeper, as she wrapped her arms around my waist to pull on herself deeper and started to slowly fuck her mouth. Gradually increasing the pressure, until I heard that tell-tale gag and I pulled her off. "Are you okay?" I asked. "Yes." She barely got out before she dove for my cock again. She couldn't fit me all the way, few can, but she made a valiant effort to take as much of me as far as she could.

Eventually I pulled her back up, licking the drool and spit off her chin before our mouths met again and I tasted the faint traces of herself and myself. I swear that's a natural aphrodisiac because if I wasn't ready before, I definitely was then. I laid her down on the couch, lined myself up between her legs, and began to penetrate her again. Her arms and legs wrapped around me, pulling me closer, pulling me further, egging me on as we started to build tempo again. When I felt ready, I backed up, before lifting her legs, bending them so that her ankles were on my shoulders as I pushed even deeper, and continued to fuck her. Every thrust bringing us closer and closer in every sense of the word. Her breathing began to rise again as her moans decorated the night like stars in the sky. I felt myself building as well, the alcohol finally deciding to hit me in a way I didn't want to, so I reached down with my thumb and began playing with her clit. Her noises encouraged me as I quickly centered on a light but firm circle, matching my tempo with my thrusts.

In, out, in, out, in, out, my thumb circling, I brought it up to my mouth to taste her juices, tangy a little sweet, fucking delicious, before sending it back down to finish the job. Her moans continued to build as I continued to build. "I'm not sure how much longer I can last." I let her know. "I'm almost there." she said grabbing her tits, pulling on her nipples, as I kept doing exactly what I was doing until her back arched, and I felt the tell tale spasms. "Fuuuuuuuuuck" she breathed as I held back for dear life. "Oh god, Alice I'm going to cum. Where do you want it?" I asked. "Inside me, please cum inside me." And that was enough. I groaned as I felt myself falling, catching myself before I accidentally crushed her (or gave a solid headbutt.) and I unleashed an even bigger orgasm than the first one. We held each other close for a while, her occasionally making little contented happy noises before I asked if she wanted to shower. She said yes, but she preferred to shower alone.

It was probably for the best, as a gentleman I of course replied 'ladies first' and hung out in the bathroom while she cleaned the sweat and sex off, and then traded places rinsing myself off, there was change in the air. Something had shifted and I don't know what. What mattered to me most though was that she was okay, and she was okay.

The next day the emotions and guilt hit me (which didn't prevent us from fucking again), as I tried to determine how to best end things with my partner. I believe that somethings can't be undone, and just like how you can't unfuck a pregnant woman (without a medical license) you can't un-cheat. I shoved those problems to the 'next week' bin and enjoyed all of the guilt-ridden sex with Alice that week. Before going home and breaking up with Morgan the week after. It still caused a massive emotional tear in my heart that sent me on a depression spiral for a few months. Alice did ask me to be her boyfriend and I said no, partly because who would want to date a cheater, partly because she didn't want me so much as she wanted her boyfriend, (dead) and to not be alone. I occasionally wonder if that was the right choice.

Alice and I remained friends (occasionally with benefits, occasionally without), and Morgan fell off into the recesses of history, I do hope she's doing well, that she got the therapy she needed, and that she finally found someone who didn't cheat on her. I am sorry that I couldn't break that streak. Alice has mentioned that week marked a turning point in her grief journey where she started finding ways to live again, and apologized for influencing me to make poor life choices. I don't regret that week with Alice, my only regret is not breaking up with Morgan sooner.

If you haven't read part one, I promise not to take it personal but you can find the details right here.

Me, 6'2", 24 years old, athletic, white, with a lesbian haircut (you know the one) and 5 o'clock shadow. My body the product of my vanity in the gym and an unhealthy sweet tooth.

Her, Alice, 5'8", also 24 years old, hispanic with a gorgeous derriere, a somewhat large (but very fitting) pair of tits, and long curly, dark brown hair. She always looked like Cleopatra to me. I had a crush on her since I was 11, and now I was on her couch, naked, feeling her skin against mine, while my girlfriend is sleeping blissfully unaware miles away.

So there I am, laying on the couch, my skin wrapped in hers as Alice looks up at me with those big beautiful brown eyes and says “Can I ask something?” Automatically, I replied “Of course.” (at this point, committing to responding with as many ‘of course’s as possible.  The bit demanded it.) “Can I kiss you?” she said, raising her brown eyes to stare into mine, her eyes shifting from my lips to my eyes, looking for acceptance.  I smiled. “Of course” I whispered to her.  She leaned in and we kissed.  A peck at first, then a tentative piercing of the lips with the tongue before backing off for a second, her breathing deepening, before she came back and kissed me again.  Harder this time.  Our tongues danced as she brought a hand up to the side of my face and her other hand went lower, trailing down my ribs before sliding back and grabbing my ass.  (I did ballet for seven years, I’ve got a bubble butt and I’m proud of it.  It gets me as much attention from the ladies as it does the gentlemen.) 

I felt that stirring that any man can tell you about, that desire and need that feels both empowering and mind controlling, as our lips locked and my hands stroked her back before I reached down and grabbed one of her cheeks.  I think she took that as approval because she lifted her butt before bringing herself back down.

And I felt it.

I felt the dripping of the past five days of tension.

I felt the need of loss
I felt the craving for comfort, as I felt bad that I hadn’t thought about Morgan once except to send my boyfriend obligated texts, rubbing up and down my rock hard erection.

And she began to grind.  Slowly at first.  Before building up.  She needed this.  She was going to have it.  “Can I ask something?” she said finally breaking away. “Of course.” I responded.  “Will you please fuck me?” She said breathily.  “No.” I responded breaking my streak.  “Then I’ll fuck you.” She said reaching down for my dick, angling it up.  If I waited just a second longer, she’d be on top of me.  There would be no going back.  And that felt just a step too far for me.  I sat up and pushed her onto her back, reversing the roles, she made an excited noise before our lips met and the moaning continued, my hard cock rubbing against her wet welcoming slit, so close yet so far.

“Please” she begged.  “No.” I responded, continuing to grind against her, her moans beginning to punctuate her breathing. I knew I should stop, I knew I should have grabbed my phone right then and there and broken up with Morgan, 'but it doesn't feel right to do it over the phone' just like it didn't feel wrong to have Alice's smoothly shaven cunt coating my cock in it's aroused juices. She looked up at me "Can I suck your dick please? Please? Just for a minute." I should say no. "Of course." came out of my mouth like a bad habit, as I sat back.

She dropped to her knees in front of the couch, and I wasn't sure what to expect. Would she dive in with the craving of a woman who had been starved for touch? Would she change her mind? Would I change my mind? Instead she brought it up to her face, examining it, as if trying to make sure the moment was real. Her mouth opened and her tongue lapped out, gently swirling around the head of my cock, and pulling an inconvenient moan from my being. Fuck me. She started slowly, focusing just on the head, rolling it around in her mouth like she was trying to savory every second, like if she let it come out of her mouth it might not be there when it returned. I wondered if she let go if I would've stopped her and said 'this is too far', instead she looked up at me, as her lips disengaged and her tongue came out giving a long slow lick from the base all the way to the tip, before taking me in her mouth, further this time, getting about half of me in. She began moving her head back and forth, slowly milking the precum out of my pipe like it was her heroine, as one hand went to grab the base of my cock, and the other grabbed my hand and put it on her head.

I took her long dark out of her face and wrapped that twice into a little bun before grabbing her head again, as she began to speed up. She wasn't the most experienced, I'd be lying if I said it was the best head I'd ever had at that point...
... I'd also be lying if I said it wasn't the hottest head I'd ever had at that point. The conflicting emotions of guilt, and lust wrapped in pleasure of her tongue tickling me just right, all while in my head fighting between "I've dreamed of this for all my life" and "What would Morgan think?"

Her mouth didn't care for my emotions though, as it brought waves of pleasure through my body I hadn't felt in days. I think if I had let her she would've kept going until the sun came up. But I pulled her off of my cock with a quiet "nooo..." before pulling her up into a kiss. She climbed back onto my lap and began furiously making out with me while grinding, our most intimate parts dangerously close to no return, "Will you please fuck me?" she asked.

"No" I responded. "Will you touch me at least?" She begged "Of course." I replied wrapping my arm around her waist and gently shoving her off of me, laying her down on the couch.

I kissed her as my hand slid lower, down her stomach, making small circles past the hips, until my fingers began trailing over that pubic mound. I noticed the smoothness, she must have shaved either that day, or waxed that week, there was no other excuse for how divine her skin felt against my own as my first finger reached her wet waiting labia. I rubbed a finger up and down the slit, getting a feel for her, and of course doing a nice gentle teasing circle around the clit. She looked up at me "Please" she whimpered. I kissed her again. "Of course." I whispered. My middle finger slid inside and she moaned. Her eyes rolling back in ecstatical agony, as I let her squeeze my finger with her pelvic muscles. I gently did that 'come hither' motion and she moaned harder. I reached up and cupped her face with my other hand as I kissed her.

I kissed her with all the love and tenderness and compassion I had. I kissed her for my childhood self who had always wanted to, but never had the courage. I kissed her for the comfort of her dead lover who was taken from us far too soon. I kissed her to soothe myself from the agony of breaking my girlfriends heart. I always told myself I would never do that. But there I was, giving up a token resistance, so I could say "I did not have sexual relations with that woman." a technicality at best, and deliberate deception at worst.

She moaned harder as I kept the rhythm going, fellas when a lady says "don't stop" that means "keep doing exactly that, at that angle, at that tempo", she didn't say "don't stop"... with her words at least. I felt her breathing rise as a long low moan came out of her soul and she grabbed my wrist and held it to her crotch. Slowly she release and I snuggled back on top, and kissed her again.

Purely by coincidence, I definitely didn't plan for it, but my cock was rubbing against her pussy again. Her wet, glistening, just-came-on-my-hand pussy, was rubbing against my throbbing "i-don't-cheat"ing dick. She kissed me again, putting her hands behind my head, "Please fuck me." She whispered. "No." I responded stoic as a statue. "Pleeease" she whimpered. "No." I replied. "Why not?" she whined. "I don't cheat." I replied automatically. She laughed. "You call this not cheating? You've done everything but."

This is why she's my friend. She ain't afraid to call me out on my bullshit. "Fuck me Jay." she repeated more demanding now, my cock aching for that place that called to it. "I'm not going to" I said pulling back slightly, her legs wrapped around me, preventing me from leaving.
"Fuck you" she said.

Or she tried to say. It came out "Fuck yoooooooooooooooooouuuuuuuuuuuuhhhhhhh" as I finally broke, and I finally slid inside. That first stroke while she adjusted to my size made me believe in God, karma, that I was a bad person, and that right now, in this moment, I didn't want to be good.

So I decided to be bad.

I pulled out to another whimpering "nooooo..." as I took my cock in my hand, slapped her clit a couple times, before lining up and shoving myself all the way in. Her hips met my hips, as I began a slow yet powerful rhythm, all the way out, all the way in, taking time to enjoy every single inch she took of me. Her begging replaced by a low "Fuck yessssss, yesssss Jay yesssss" as I took out my week worth of sexual tension, months worth of relational frustration, and decades worth of pining on that tight hole enveloping my cock. Steady, constant, I heard her breathing building again. "Are you going to cum again?" I asked her. "noooo..." she whined. Lying bitch. "Oh, so I should stop?" I asked as I cut my momentum and pulled out. "No no no no no please please please." She begged as I lined up, and began again faster this time. "Are you going to cum for me Alice?" I asked. "Yes. Yes. Yes please. Yes I'm going to cum for you." She managed to get out before another scream came out as she shook.

I've said it before, I'll say it again. Momma didn't raise no bitch. It's not over when you cum, it's over when I say it's over, and I wasn't nearly done yet...

Part 3 and finale tomorrow.

I asked and you answered.  Welcome to the smutty story of one of the worst decisions of my life.  Don’t get me wrong, I don’t regret my actions here.  I regret my inactions in this story.  I’m going on the record right now to say “Cheating is wrong” but I was hot, horny, and unhappy and made my choices.

You know me, J.  6’2” with a statistically above average penis.  I have dirty blonde hair that ranges from your standard short lesbian cut to my midback depending on how bored I get with it.  In this story it was short.  I work out, it shows.  To quote a TikTok, men workout to look cool during sex.  Sure you can do it to live longer, but you only gotta live longer so you can keep looking cool while having more sex.  I hope to continue fucking until my 90s.  But that’s more than a few decades away.

In 2019 I lost my virginity to my sugar momma, which is a story for another time, but while that year was a wonderful exploratory year, 2020 happened and I caught the feels for a girl and decided to settle down for a bit.  We’ll call her Morgan.

Now Morgan was 5’2”, 21 years old, and a little chubby, but it honestly just highlighted what she had (tits and ass).  She had a cute face, cute features, and was a woman recently single who was living life and loving it.  I met her as a coworker, we hit it off, one date turned into two, turned into a thing, turned into a relationship.

Then came the insecurity.  I was the only kind man she’d ever been with.  It started subtly with her not feeling like enough and me comforting her.  Then it started ramping up to her accusing me of cheating on her because I didn’t respond to her text while I was working.

During the pandemic…

In a coffeeshop…

Right, because between the 120 customers I’m serving per half hour (there’s nothing to do but the drive through I guess, and we were right next to a home depot.) I’m secretly blowing backs out in the break room.  The camera recorded break room.  Clearly.  

Now as a 24 year old who had one prior relationship to this (and remained a virgin throughout that relationship) I wanted to be the white knight.  The shining gentleman who came through and was perfect the entire time.  Because if I left then clearly I was validating her bad opinions of me right?  Well 6 years later I call that boundaries, but at the time I was young and made poor life choices, and that’s what you’re here for.  So let’s get to it.

Let’s introduce our antagonist for this story.  Alice.

Alice was one of my best friends growing up.  Alice was 5’8” hispanic with a butt that is a crime against humanity to hide in pants.  While Morgan was a kind spunky spitfire, Alice was a calm and dependable companion you could talk to about anything.  Growing up I always had a crush on her, and knew it was never reciprocated, and I was okay with that.  Sometimes pining is half the fun.  While our relationship was and is one of the longest lasting connections in my life, I know that as people grow and move sometimes connections fade.  That’s not a problem.  Alice got a wonderful boyfriend, and I started hearing from her less and less.  She was happy, we chatted maybe once every three months or so.  Life was good.

Until a car-accident went and killed Alice’s man.  Life sucks sometimes.  She got dealt the shit hand.  She spiraled hard.  Yeah, remember the whole “stay home, don’t go out” thing?  Well guess who died RIGHT before that happened?  Alice was a wreck, and surprisingly Morgan suggested I go and visit and take care of her.  She was like a sister right?  Of course I would take care of her.  It’s healthy for men and women to have solid platonic friendships of both genders.

So I did.  I took a week off of work, and showed up at Alice’s apartment.  She had a two bedroom, so I slept in the spare room.  Sometimes she was more or less catatonic, sometimes she was mildly functional.  I was there to support my friend.  So I cooked some healthy meals, we played some games, and I in general, did my best to give her a little bit of something worth living through the day with.  Grief is a bitch, and anyone who tells you otherwise is wrong.

It started innocently, we were playing sequence, and I told her I was going to wreck her ass.  She said “You wanna bet?” to which I replied “What’s in it for me?”  She looked at me with a longing that I’m not sure I could describe in words, maybe it was a primal need, maybe it was an attempt at finding her boyfriend one last time.  “What do you want?” She asked.  “If I win” I began, “You’re making dinner tonight.” I finished.  She laughed, the first time I think I’d heard her laugh that week.  “If I win, I get a kiss.”

Dear readers, I am faithful, I would never cheat.  So I pulled out all the stops and won the shit out of that game.  She never saw it coming.  But that’s how it started.  A bet that she lost.  It became a running bit for us “Wanna bet?”, but she got more desparate.  “If I win, let me suck your dick for five minutes.”  Now I know, as a self-described slut, it’s hard to believe that I would turn that down, but I am a faithful man right?  I’d never cheat, but I couldn’t leave Alice hanging.  “How about if you win you finally get that kiss?” I replied. “Deal” she said maybe a little too quickly.

She did finally win one, and I am a man of my word.  It’s just my friend after all right?  She’s basically a sister, (and I whole heartedly believe men should kiss each other platonically like they do in Spain, or Argentina, or Uruguay or I could keep going but you get the point.) and she’s hispanic so it’s one hundred percent innocent right?  Well, I am a man of my word.  So I kissed her on the forehead, and she gasped and then crossed her arms and frowned “That’s not fair.” She pouted.  “You didn’t specify where I’d kiss.” I returned.  “No, but-”

I’m sure she was about to try and make some sort of logical argument why I should kiss her on the lips.  If there’s one thing I am besides a slut, it’s a clown, and I’m committed to the bit.  Interrupting her logic train with a quick peck on the lips sending her brain into overdrive was even funnier than a forehead kiss instead of the lip kiss.

“Wait! That’s not fair! I wasn’t ready!” she pouted some more as I laughed.  “I don’t know, you won, ‘a kiss’ and you got two.  Why are you so greedy?” I teased, before adding in “I guess you’ll just have to win another one.”

And so it began.  One kiss turned into a kiss with tongue, turned into her wanting to show herself off for me.  “It’s not cheating” I told myself, “if she were a guy, and we were at the gym we’d shower next to each other, it’s not that different.” I reasoned, and of course once she’d been naked, she could win me being naked right?  It was only fair.

I remember the second to last night I was there we made a bet, I wagered her nudity for the night, against her “you have to drink double what I do tonight”, game on.  No way I’m losing this right?  Well as any avid sequence player will tell you, skill is great, but there’s no cure for the luck of the draw, and I was cooked.  I had committed to drinking twice what she drank that night, and mama didn’t raise no bitch.

So naturally we played a drinking game while watching a movie that night, and I’d like to think I held my liquor pretty well, but she tapped out after six shots of tequila, and in spite of chasing my twelve with water I was feeling pretty loose myself.  Somehow I wasn’t slurring my speech and could walk in a straight line, but the room was wobbly regardless, the movie ended and she asked if we could snuggle.  “Of course.”  I said, as we went from parallel on the couch to her laying on my chest.  I was aware of her d cups pushing into me chest, as she looked up at me.  I could feel her breath on my face as I asked “How are you doing today?”, “I’m okay,” she responded, and then hesitated a bit “Can I ask for something?” My heart melted, if I could have won the lottery and given it all to her in that moment I would’ve.  “Of course.” I said.  “Can we snuggle without our clothes?” she said, her voice fading to a little whimper, afraid I would reject her. “Of course” I said, surprising her, and myself with how quickly it had come out.  She sat up “Really?”  “Yeah.” I said “I mean, we’ve already seen it all anyway right?” She laughed at that and took her shirt off.  She didn’t wear a bra at home, (I mean, why would she?) and she started to unbutton her black skinny jeans when she saw my lack of movement. “What are you doing?” she asked “Waiting for you” I replied “I thought you were getting naked too.” She said slightly disappointed.  “I am” I responded “I’m just waiting for you to undress me.”

Well her pants stayed on as she came over to take my shirt off, revealing my abs she enjoyed laying her hand on, and my pants came off, and underwear with them, and then she returned to her own coverings, taking it all off before returning to my chest, where she laid her head down again.  One of my arms reached to pull her closer while the other began gently stroking her hair.  She laid there for about five minutes before feeling emboldened by her first success. “Can I ask something?”  She requested, looking up at me with those big beautiful brown eyes and I knew right then and there, I was in trouble...

Part two coming tomorrow. -here