Satisfying my friend’s exe’s wild side [MF]

These events took place about 5 years ago and the names of the people involved changed for anonymity. I’ll refer to myself as Jeff- 25, 6′ 1″, 165 lb slender muscular build, medium length dark brown hair, and blue eyes. My friend and roommate Kevin- 24, 5″ 10, 160 lb average muscular build, short lighter brown hair, and blue eyes. Kevin’s girlfriend Kasey- 23, 5′ 4″, 115-120 lb athletic build, B cups, fantastic thick booty, toned tummy, long dark brown hair, green eyes. Best comparison I could quickly find is Gia Page.

So my story naturally starts with the first time I met Kasey. Kevin and I had been friends for three or so years, roommates for two, when in my early morning slumber I wandered into the kitchen and locked eyes with a stranger and possibly the most gorgeous woman I had ever met. It was Kevin’s new fling and soon to be girlfriend, Kasey. I saw her green eyes light up with a fire behind them, pupils dilated, and a sly smirk concealing what I would eventually find out was a strong mutual attraction from first sight. I knew I was in trouble….

Letting him control me [F]

If you read my last story you know I’m currently very interested in a guy I️ met off Reddit. Sadly he’s across the country but that doesn’t not make me want to get on the next red eye over just to get on my knees just to taste him. Of course I️ had to tell hubby I’m trying to get like America’s favorite cookie, double stuffed. He then proceeded to fuck me hard from behind and remind me that playing slutty games gets me slutty prizes.

Fast forward a few days later while hubs was working, I️ was thinking about Reddit boy and remembered that I️ have a Lovesense Lush — for those that aren’t familiar, it’s an app controlled vibrator and it lets you go long distance…like across the country distance ( thanks Hedy Lamarr!). I️ was between work calls and I️ asked my new crush if he wanted to play. Lucky me he was free.

[M]e and C #2: The time I enlisted her best friend to help me punish her

This is a followup to the last story I posted, which you can find in my post history if you want to catch up first. The tldr of that story: I had a dysfunctional relationship with my first serious girlfriend in college, C, which lasted about 3 years in which we repeatedly cheated on each other.

This is jumping ahead a bit, to our last year of college when we’d both basically gotten used to the way things were. She’d already cheated on me three times prior to this (including the first one, described in my previous story) but I had only done it in retaliation once, and I actually don’t know if she ever found out about that one. But basically, the ongoing dynamic had been established: when she got frustrated enough, she’d fuck someone else without making any effort to hide it, wait for me to find out, and I’d find something to do to her as her dom that one-upped the last time as her punishment. So we were getting to the point where I really would have to be creative when it happened again.

[MF] How he found out I’m a cumslut

I think he knew the night he fucked me outside, where anyone could have found us. Up until then, we’d spent the summer in my cramped bedroom going at it until we couldn’t stand up. One night we were starting to get hot and heavy, but my family was home. He started whispering to me about taking me out and fucking me somewhere. I was honestly weak when I heard him talk like that. He was holding me, kissing my neck and playing with my tits, saying things I’d never heard him say right in my ear. I’m still not sure if he knows how submissive it made me. As soon as he told me to get clothes, I pulled on a little sundress, leaving my panties and bra behind because he told me to.

He took me to the bike path near my house. I flashed him my tits on the way, but I didn’t know how far he’d take it once we were in the shadows. We started kissing and he pushed me against the sturdy, wooden fence. I leaned back onto it and spread my legs while he dropped his shorts. He slid his cock in so easily and started fucking me fast and hard. It was hard to hold the position, so I bent over the fence for him instead.

Back in the good ol’ days when I used to fuck my best friend’s cousin. [FM]

I was in sixth form (college) at the time so I was 18/19. I really fancied my friend’s cousin who was about 8 years older than us. He would speak to me via Facebook and I would flirt with him loads but he didn’t give me much back – though he would still regularly talk to me and often message me first.

He knew I was interested in him, I’m very forward so I made that clear early on. Nadine knew I was into him because in our friendship group me and the others would joke to her that he was hot – she’d laugh and say he never would sleep with any of us because of a potential family fallout.

He said anyway that I was too young and he couldn’t because I was his little cousin’s best friend. I was quite close to Nadine’s family, as we grew up together, and he had seen me growing up too so he thought it would be weird and he knew that none of their family would approve because of the age difference etc.

I would still talk to him regularly even though I knew nothing was ever going to happen between us.

3 Holes in 2 [M]inutes. Used like the perfect little [F]ucktoy

As soon as I stepped inside the doorway I was his. He knew this. I knew this. I had driven to his house with a butt plug in my ass after all, though nothing could have quite prepared me for what was about to happen.

After pinning me against the wall and pushing his fingers into my cunt he lead me to the next room, got me down on my knees, and promptly started fucking my face to get his dick wet. First hole.

I was then bent over his dining table, with my dress pulled up to expose my bare ass. He pushed his big dick all the way into my tight, wet, and waiting cunt. A few thrusts was sufficient. He had other plans. Second hole.

I begged him to fuck and cum in my ass, just like we’d fantasised about. He didn’t take any persuading. I was there as his fucktoy, after all., and he treated me as such. Within a minute and a half of arrival he was roughly fucking and violating my most precious of holes, my ass, and by the third minute he had filled it with his cum. Third hole.

My [F] first gang bang

I’m (29F) not sure how my boyfriend worked all this out, but I’ve been wanting to be gang banged for awhile. I sent him a video of a gangbang with a 😏 and he said “Noted”. I’m not sure how you’d approach your friends about this, it seems weird to just say “Hey Johnny, my girlfriend is a real freak and wants to be gang banged. Are you interested?”, but he managed to get together 7 friends in a group chat with me and we talked for a bit last night. I was off today and was ready. I’d gotten a Brazilian and was completely smooth shaven.

We went into our master bedroom and I began slowly taking my clothes off as seductively as I could (as cringey as it was). I was really nervous seeing their eyes watch me like predators, but I was also super excited and ready for the hard fucking I’d get. I was completely naked and got onto my knees and motioned them to come towards me. I bent forward and put one of their cocks into my mouth and began sucking while one of the other ones spanked my ass super hard (kinda hurt) and he grabbed my hips and mounted me and slid his cock into my pussy and began to stretch me out. I felt other guys rest their cocks on my forehead, smacking me in the face with their hard cocks as they slowly stroked them. I used one hand to jerk off which ever cock found its way into my hand while the other guys squeezed my boobs, spanked my ass, etc.

[MF] Taking her from behind while she talked to her Pastor..

So, I’m a 48 year old Caucasian male awaiting back surgery. To pass the time and deal with the boredom and depression my wife suggested posting stories of my sex life. We both read this site and love it. She won’t let me tell any of our stories so instead she suggested I tell about my experiences before we got together.
Iris and I dated for about 3 years when I was finishing up my short stint at community college. She was Jamaican and a year older than me (I was 20 and she 21). She had a daughter who spent the mornings and afternoons in school and fortunately was a deep sleeper, because Iris and I definitely had a lot of fun in the bedroom at night.
But it wasn’t just the bedroom or just at night. We kind of had a agreement – anytime, anyplace, anywhere. This led to such situations as me fingering her on her mother’s couch while her mom was making dinner, or her making me cum in my pants by giving me a standing lap dance in the elevator at the mall.
At one point we were living in an apartment complex and one particular day we were supposed to be going out to run some errands. We had showered and she had kind of stopped me from fooling around in the shower because she said we had to hurry and get going. So we got back in the bedroom and we’re getting dressed when suddenly there was a call to her from the open bedroom window. At the time she was wearing a nice T-shirt and a pair of purple panties. Now Iris wasn’t that tall, standing about 5’4″, so I had a foot on her. She had a nice body, a pretty face, not much up top (she was a 32b cup) but man did she have a great ass (measuring 40″ around). It was a sight to behold and to be honest just watching her walk around was better than watching a porno.
She leaned out the window and draped the heavy curtains over where her waist was. This gave the advantage that she could talk outside to whoever was calling her without them being able to see past the shirt she was wearing. Unfortunately for her it also gave me an incredible view of of her wonderful posterior. It turned out the person that had called to her was the local pastor who she knew because she was a big church goer (I was not). He had apparently been visiting one of our neighbors and must have heard Iris talking through the window when he called to her. So there I am sitting on the bed looking at her ass while she is leaning out the window and talking to her pastor and just to be cheeky I reached out and pinched a cheek. Well she kind of gave me a quick glance over the shoulder, and she wiggled her ass a bit. She meant just to be picking on me because she knew I’d been in the mood earlier but oh she underestimated just how in the mood I had been. So while she was standing there talking to her pastor and wiggling her butt at me I reached out and began to massage her pussy through her underwear.
She immediately stopped wiggling and I heard her give out the slightest of gasps, yet she continued on with the conversation with the pastor. It only took a few moments of me rubbing before her juices had completely soaked her underwear and I slipped them off of her. I could hear her trying to wrap the conversation up with the pastor but he had a tendency to be long winded and didn’t seem ready to quite let her escape his sermon just yet. Removing my pants and underwear I stood behind her, glad that the curtains blocked me from the window, and very slowly and gently I slid into her. She let out another little gasp and as I continued to slowly rock in-and-out of her I noticed that her side of the conversation changed from normal talking to short response such as “yes” “yea” “uh-huh” “mmhmm” “OK” and not much else. I was having to bend a bit at the knees due to our height difference, but I always loved watching her ass jiggle when I would take her from behind (a position we did not do very often because she liked to be able to look me in the eyes during sex). So I began to speed it up a little faster and a little faster. Not so much as to make a lot of noise, but enough so that I could see her ass jiggling as I slipped in-and-out of her. She was desperately trying to get out of the conversation now and the pastor just didn’t seem to be getting the hint. Her breathing was much deeper and she was doing her best to keep from moaning. I just kept up my rhythm enjoying both the feel and the view.
Finally I could also tell that the pastor was starting to wrap up what he had to say and I knew once he was done she was going to stand up and I would lose my positioning. So I decided it was time to go for broke. Now I was going hard enough and fast enough for there to be some sounds, thankfully the pastor didn’t seem to notice. But I could hear the sound of myself slapping against her ass with every inthrust, and the view of her ass jiggling madly was more than I could take. Now normally she liked me to unload inside her, she knew how much I had a tendency to cum and I had definitely sprayed more than my share of semen on her since we started dating, but she liked feeling it explode in her. This time though I pulled out when I just couldn’t take it anymore and I fired shot after shot all over that big beautiful rear end of hers. I loved the sight of my thick white cum splattering against her dark skin and despite the fact that I have a tendency to ejaculate copious amounts I still couldn’t even come close to completely coating her butt. Yet as I collapsed on the bed as I heard the pastor say goodbye and looking over I could see her juices was running down her legs, letting me know that fortunately I was not the only one who achieved orgasm.
She finally said good bye to the pastor, stood up closing the window and the curtains, turned around on shaky legs and told me she was so going to get me back at some point. She did in fact, but that’s another story for another day.

[MF] I [F] Had the The First Amazing Sex of My Life With an Older Stranger [M] in His Hotel Room Assuming I’d Never See Him Again… He’s now my Fiance’s Boss

# Intro

I’m going to start with some context. This all took place a little more than three years ago after flying back home for the holidays to spend time with family. It was also about a year before I started dating my now fiance. I don’t remember all of it perfectly, but some of it is pretty vividly imprinted. I apologize if some parts are vaguer than others though. I also apologize for how long this is… I really got going and to be honest I mostly wrote it for myself, so hopefully people are just okay with that, and any spelling errors…

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**Disclaimer:** I can see, after writing this, how the title might lead people on to thinking that I’ve done something with the man in question since. I haven’t. There’s no cheating here, and no follow up to speak of. Sorry to disappoint if you were hoping for that.

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# Context and Setup

The flight back out to where I attended school had a short layover and plane transfer, with a different airline for the second leg. I met the man in question as he was seated next to me. I’m a really introverted person, and I usually hate talking to people on planes, but Andrew (which is what I’ll call him for now) had a real talent for sort of just coaxing me into conversation.

I 25 [F] fucked an ex 22 [M] in a hotel straight after a breakup with my 34 [M] Boyfriend

Heya!

I’ve been telling the story of my sex life over the past few years and this is a second installment. You can find the first part [here.](https://www.reddit.com/r/gonewildstories/comments/p1wy5i/a_breakup_between_me_f_and_an_ex_m_partner_leads/) This also falls under the monthly contest! Wish me luck!

My current boyfriend and I went through an extremely rough patch a couple of years ago. It’s not important why we broke up, but what I did and couldn’t wait to do soon afterwards. I went through a phase a few months before after a previous breakup where I fucked a bunch of exes and had a few one night stands with random guys, so I thought I’d do the same with this one.

The day after the break up I was feeling extremely upset and needed comfort in the form of a dick, so I contacted my favorite ex, Marcus. Terrible boyfriend, but and amazing fuck. We knew what we were when we’d meet up and that was sex. Pure pleasure. He lived 2 hours away in a different city, so I booked a hotel for the night in his city and headed his way.