My First Time Cheating [MF]

I don’t really remember exactly when this happened or how old either of us were at the time. I do remember the night, but not all of the details leading up to it.

I know I had posted an ad on Craigslist, probably just looking for local women to chat with. Heck, I may have even responded to an ad. During that time, I found a fair amount of success using the “Strictly Platonic” section just looking for chat friends. It seemed a lot of women would post and respond there because it wasn’t explicitly looking for sexual connections.

Anyhow…I had started chatting with a woman and Celia. She lived maybe 30 minutes from me and we hit it off pretty quick. It all started out fairly normal, but after a while the topic of sex came up and we began discussing likes and dislikes and starting to talk explicitly about what we could do together. Read more »

Airport Pickup (MF, cheating, oral, public)

I was only supposed to pick her up from the airport and bring her home. My wife had asked me to do it since she had gotten sick the night before. Her friend, Olivia, or Oli for short, was returning from a business trip. I waited at the airport waiting lot for about 30 minutes before I got the call that she was outside the terminal for pickup.

As I pulled up to the curb I saw Oli. She is about 5 ft 8 inches tall, slender body with huge tits that were very well pronounced in the green floral sundress she was wearing matched well with her vibrant red hair and clear green eyes. Obviously having never told my wife this, I had jacked off to her more than once. Oli threw her bags into the backseat and sat in the passenger seat. We greeted each other and I drove off, we lived in the same neighborhood and it was about an hour from the airport.

We made small talk, asking her about her trip and how the flight was. She asked me how my wife was feeling and how my work was doing. It didn’t take long until we had run out of things to talk about. We just sat in the car listening to the radio. Read more »

Bring Me Back a Hawaiian Girl [MF, humor, cheating, interracial, preg]

Her husband dropped her off at the airport and helped her get inside with her bags. She asked him if he wanted any souvenirs from Hawaii.

He laughed and said, “Bring me back a Hawaiian girl!” before giving her a final hug and kiss goodbye, and returning to the car. He made such jokes often, whenever her work sent her to far off destinations. An Italian girl, he’d asked for. A French girl. A Japanese girl. How serious was he, when he made those jokes? Were they really a joke, or merely a way to gauge her interest with some plausible deniability? If she came back with a Hawaiian girl to add to their household, would he be delighted? Would he dote on her every day? Share their meals with her? Pamper her? She suspected he would. He was popular with girls. They liked him, and he liked them back. Read more »

[M]y post-break-up revenge

(Meta: I’ve been hesitant about posting these things for a while because, well, anonymity and whatnot. However, I’ve occasionally used this, and many others, as inspiration for various prompts on /r/dirtypenpals or the like, or let others use it as inspiration for their stories. A friend of mine from /r/dirtypenpals encouraged me to try it out nonetheless, since old enough events are likely enough not to be problematic anymore. Writing all this has been super fun and I am now officially in love with this subreddit! Here it goes!)

You know how dealing with a break-up from a long-term relationship sucks? Especially when you put a lot of soul into it? *Especially* when you’re young, and it’s your first long-term relationship? And *especially* when it ends up because your long-term partner is cheating on you?

Well, I dealt with a lot of “especiallies” and I tolerated it all because that’s the nice thing to do. I’m not a spiteful person. I do believe that one of the reasons why modern society is so fucked up is that nobody drinks from their skulls of their dead enemies anymore, but I also think that anyone can make a mistake, and that not every petty act deserves revenge. And many just aren’t worth the effort of revenge. Read more »

[M]y [F]irst threesome with my wi[F]e and her best friend..

So I figure rather than share our photos and videos, I’d take you down memory lane. My wife and I have been together for a decade. At the time – her best friend of 20 years had broken up with her boyfriend. Mind you – these girls are stunners, both long haired brunettes, model looking, fit with abs and FAT asses. The three of us were always inseparable. One night we decided to do some MD and GHB together.. my wife began to tell her friend how hot she was and how everything was his loss etc. – She wasn’t wrong.. Couple of hours in and the girls began commenting on each others appearances, out of nowhere my wife pulls my shirt off knowing it was my first steroid cycle telling her friend how a man should look like me, next thing you know & the clothes started coming off.

Her friend had been sexually deprived for a a couple of months now (Both of them are freaks in bed btw), she started kissing my wife until they took it to the bedroom, I’m pacing in the room smoking cigarette with a brick in my pants watching and yes of course I couldn’t stop touching my\self. Read more »

My [f]riend wanted me to finger her [f]or a little fun after making out, but I ended up giving her more

Sher [f] was a good friend of mine. We ran in the same party circles for many years, and her boyfriend was friends with my[f] friends. When they broke up she was feeling bad because she ended up moving in with some roommates and lost touch with a lot of our friends.

I’d go visit her at her place from time to time. Her and her roommates all worked together at a restaurant and were not always on the same shift, but they were usually drinking and smoking when I’d go over in the evenings. I’d drink and sometimes if I had too many I’d sleep over on their couch.

One night Sher was feeling particularly sad and missing her man. I had comforted her and told her she would be just fine. I told her she was a fun and pretty girl and I loved her body. She’d find someone and forget all about him. She looked at me with a funny look in her eyes. “You like my body? Really?” She asked. I stopped short for a second and realized what that look was. She scooted a little closer and I could feel tension building. I did find her attractive and we were good friends.. Read more »

[M] A weekend with [M]ark

Previous story [here.](https://www.reddit.com/r/gonewildstories/comments/ifo69b/m26_my_first_time_with_another_m/)

I’ve been chatting and meeting up with Mark for the past few weeks, and having a great time exploring my sexuality with him. Earlier this week, he invited me to stay over the weekend at his place, which I gladly accepted.

I showed up Friday night, and Mark was having a few friends over. I was nervous, because I’m not open about this side of myself yet, but his friends were really nice and welcoming. Mark had floated the idea of a threesome by me before, so I thought that maybe this was a set-up of sorts. I was honestly excited about it, but after an hour or two his friends left. I had the feeling that this was sort of a pre-meet orchestrated by Mark to see how we’d all get along. They were both nice, handsome guys, and very funny. We were laughing the whole time. After they’d left I asked Mark what that was about, and he played innocent saying they were just his friends and they do this every weekend. I could see the way they were all looking at me though, so I decided to get a little slutty and I told Mark that I was game if they were up for it. That brought out a little smile, but we haven’t discussed it much further. I’ll be sure to share if that ever happens! Read more »

A guy filmed me [M] twice fucking his lady [F], then he ate my creampie

Some years back I replied to an ad on Craigslist from a couple looking for a guy for a threesome. They invited me over, asking only that I bring some lotions along and give the lady a massage before banging her. I have limited experience with massage but of course I agreed and stopped at a store to pick up some lotions on my way out. They lived way out by the lake, in a house on stilts right by the water. The guy had the word ‘pirate’ in his email handle, and a thick beard with little braids in it. The woman was short and busty.

So I rubbed some lotion on her back and shoulders for a while, doing the best I could, and then she was ready to fuck. I told the guy I was fine with being filmed as long as he did not film my face. He was cool with that. It seems he films all their many encounters with other men, and enjoys viewing them again and again. She is not into that. She lay on her back while I fucked her for maybe 8 minutes before I launched a thick stream of cum inside her. Then he fell to his knees in front of her and ate my creampie, right there in front of me. He and I hung out for a few minutes drinking beer before I headed home. Read more »

The karate girl

I often go to the gym when where I see different girls working out. I’m a decent looking guy maybe a 7 or an 8 out of ten. I’m a little bit muscular since I go like 2 or 3 times a week to the gym.

One day I went to the gym and I saw a kind karate girl who can do high kicks like a ufc fighter. And she is a nice looking girl with a perfect body. She was currently working the heavy bag with high kicks bam… bam… bam… kick after kick. I went to her asking if I could use the heavy bag after her with a nice smile on her face asked me well… if you can work the heavy bag why don’t you train with me? Me looking at her body up and down she had a sports bra and a very tight sports workout skirt. And she was sweating on her whole body in. Read more »

Fucking my long distance gf

This is a fantasy of fucking my long distance gf, it’s my first try to write something like that, hope you like it!

You’re on your back, legs open wide, knees brought to your chest with your feet in the air. My face inbetween your thighs, so close you can feel my warm breath against your wet pussy. Then I do it. I look up at you, lean in and suck that little clit into my mouth, flicking and sliding my tongue over it as it’s inside. Gently rolling it inbetween my lips. You hear your clit pop out of my mouth as it gets sucked. Eating that little pussy, preparing you for what’s about to come. Making you drip down your groin and towards your asshole. At this point I grab the back of your knees and push them back further, revealing that tight little asshole covered in your pussy juice… and I’ll bury my tongue in and swirl it around, cleaning you up. Watching your hole repeatedly tense up and relax with excitement. Read more »