Category: gonewildstories

It’s always the crazy ones. [M/F]

They say you should never stick your dick in crazy. And, really, it’s true. It’s just an insanely bad idea. Play stupid games, win stupid prizes and all that.

What they neglect to tell you is how fucking awesome sticking your dick in crazy feels.

A few years ago, I started dating Crazy. She contacted me through OkCupid and I could tell from a mile away that she came from a rough childhood. It’s pretty easy to spot trauma survivors if you know what to look for. Thing is, I actually liked her. She liked me. We fucked on the first date, but that’s not where this story takes place. In fact, this story takes place after we broke up.

One thing you should know is that Crazy was spectacular in bed. Like… holy shit. I still have a (VERY poor quality video) that, even years later I enjoy watching her fuck herself. Not only is the video itself enjoyable, but it reminds me of how amazing it was to fuck her. Read more »

Getting [F]ucked with his cum still in my [M]outh

After positive reactions from my first post: https://www.reddit.com/r/gonewildstories/comments/4cczzn/22f_hot_reunion_sex_22m I have decided to share another experience – in fact the one from the following morning! For description of myself and my boyfriend, please see my first post.

It was the morning after our HOT reunion sex and I awoke with one thing on my mind: I wanted MORE. As we were still spooning I gently started rotating my hips, pushing my ass back into him with each circle. I heard him start to stir and felt a hand on my hip, unfortunately it was accompanied by a firm ‘no’. I rolled around to face him, in doing so his hand fell and lightly skimmed across the front of my thong. He felt how wet I was through the small laced fabric, there is no way he could not have felt it. He quickly readjusted and laid on his back – a typical tell-tale sign of an erection, or of an impending one. He was awake now, and asked for a hug (he likes it when I straddle him and we hug in that position) I was happy to oblige and I soon felt his erection pressing into me through our underwear. It did not take much from his ‘no’ to change to an eager ‘yes’… Read more »

[m/f] Playgirl Magazine Photoshoot PART 2

Hey everyone, thanks for the PM’s. You can see the first part here:

https://www.reddit.com/r/gonewildstories/comments/4chtz4/mf_playgirl_magazine_photoshoot/

I’ll pick up right where I left off;

Dayna and I were in my kitchen and I had just shown her the email. We talked about it for a few minutes, she was smiling…I couldn’t tell if she was just as nervous and shy as I was at that moment in time.

“You should do it!” she said encouragingly, half laughing as she punched me softly in the shoulder. “Then I can blackmail you when you’re famous.”

“Who says you’re gonna get a copy of the magazine?” I shot back with a grin. It was really hard for me to maintain my composure. My knees were shaking. I was so turned on and excited that we were even talking about it, let alone the possibility that my fantasy was about to become a reality.

“Well I have a camera…” Dayna said, her eyes casting toward the ground. She looked back up at me, almost hesitant. “I mean, I could do it…if you want?” Read more »

He [F]ound [M]y Newest Weakness [[Long]]

*Hopefully this isn’t too long to be interesting! I finally figured out my boyfriend and learned even more about myself in the process. I think this night and the one from my previous story helped me to be better at writing these types of stories. Enjoy!*
—————-

I still remember my first time. I remember losing my virginity in a cheap hotel room out of state and away from home. I remember not really wanting to lose my virginity that night, but not having the courage to say no. Since then, it’s been hard for me to know who I am sexually. It wasn’t a violent night or anything. Nothing to really dwell on, but it wasn’t that enjoyable either. I’ve since moved on and found that I quite thoroughly enjoy being with someone in such an intimate way. Read more »

It’s not cheating if you get caught… [F/M]

*Guilt and Pleasure: Volume 3*

**[It’s Not Cheating If You Get Caught](http://imgur.com/5ADcpp0)**

by Matthew Myen

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If this is the first of mine you have read, please read the [first part](https://www.reddit.com/r/gonewildstories/comments/3shg5r/its_not_cheating_if_you_dont_touch_fm/) and [second part](https://www.reddit.com/r/gonewildstories/comments/3y0gng/its_not_cheating_if_you_only_look_fm/) before continuing.

This final volume seems like a good place to put the full stop and I hope you agree with that decision. It’s about the same length as the second volume, if you’re wanting to know that before you get started.

All the best,

Matthew

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**Chapter 1**

The silhouette on the landing above shifted and coalesced into a shadowy Dan, a faint filter of light from downstairs throwing him only vaguely into relief as he came towards the top of the staircase. A small, bright bar of illumination marked his jeans from the crack under the bathroom door where Lily was still trying to catch her breath after having it violently fucked out of her. Dan’s eyes regarded me above a mouth that was set in a serious line.

“Dan¬—” I began, but cut myself off, not wanting to give away anything that he hadn’t already heard or guessed. How loud had we been? How long had he been up here looking for me? Read more »

[m/f] Playgirl Magazine photoshoot

So here’s some backstory: (sorry if this reads funny, I’m typing inside the text window here):
I knew Dayna from my freshmen year of college. We got along well because we were both kinda nerdy and liked skateboarding, anime and old sci-fi movies. She was a little more open about her love of Star Wars and everything geeky, whereas I was a little more withdrawn because I was into sports, and with that came the ridiculous stigma, “football players don’t watch Japanese cartoons”. In high school I was an athlete, and while I ran with a kind of ‘in-between’ crowd, youthful naivity kept my nerdiness closeted. I had an irriational fear of being socially ‘outed’ because nobody else was into that in my high school. College was great because I finally felt free to express myself and I met a ton of like-minded people. Dayna caught my eye immediately because she was tan, fit, had short black hair (pulled back into a ponytail…I don’t know what it is about girls with short hair that drive me wild, it just does) with a juicy ass and pair of breasts to match. Despite her physique, she hadn’t been wildly likeable in school. She had run with the ‘nerd’ crowd and as a result, didn’t know how hot she was. Come high school graduation, she had become full-figure gorgeous. Despite my sports career, I was equally shy and the two of us meshed well. We dated for a few months before we broke up and went out separate ways. It was mutual. Read more »

Celebrated the win in a big way (m/f, maybe tifu?)

Sunday was an absolutely wild day. I had packed over to the best Syracuse bar in town to watch my Orangemen play Virginia in the Elite 8. Most of us at the bar weren’t expecting much (Virginia had kicked our asses the last few times we played, and duh, 10 seed vs a 1 seed). I was rocking my lucky ‘Melo jersey (with a white T-shirt underneath, I’m not a monster). I had bought it right before the tournament mine (and Carmelo Anthony’s) freshman year, and wore it for every game through the stunning Championship game. Since my divorce, I had lost 30 lbs and fit into the jersey again for the first time in almost ten years, so why the hell not? Read more »

My affair with a sexy, exhibitionistic carpenter (MM) [MM] (M/M) [M/M] …mmmmmmmmmmm

I love to recall an encounter I had with a horny carpenter who was working odd jobs on weekends. I had recently moved into a new townhome, and I discovered the skylights over my living room leaked during a rainstorm. I was furious because all of my furniture was new as well, and water dripping on my couch would never do. I called the people who sold the property to me, and I complained bitterly about their shoddy construction. They assured me a reliable repairman was scheduled to fix my leak that following Saturday. In the meantime I had to place containers under the dripping water when it rained.

Saturday was my day off, and I wanted to stay in bed until late in the morning, but I couldn’t because the repairman was already thumping on my roof as soon as the sun came up. He didn’t bother to knock on the door prior to working because he was hired by the builder. I decided to get up early, and I busied myself with some housecleaning because I wanted to stay around until the repair work was done. I remember being impressed when I realized the carpenter was removing the shingles all around the skylight to make sure he found the exact leak. This guy appeared to know what he was doing. Read more »

The period girl

4 days on from shockingly yet unsurprisingly coming home empty handed from a date that explicitly said she was dtf it’s time for my next tinder adventure. Last time I had a bad feeling even though it seemed so certain. This time I had a really good feeling- it seemed so certain but this girl had been more subtle about it saying she likes to be cheeky etc. I was fully expecting this date to be about getting with a girl that’s much older than me, something I’ve always wanted to do (what guy hasn’t had that fantasy). I’ve been with girls a few years older than me, but at 38 she has a full decade on me. Now a few years ago I had the chance to get with a 40 year old but truth is whilst I want to get with an older woman to tick it off as another thing off the list, I still want to keep standards so they still have to be attractive and not wrinkled up and on the shelf. Read more »

Plan B – Married Guy [F]ro[m] Craigslist

I’m traveling to a new city, and my “ride from the airport” bails on me. I’d been looking forward to, shall we say, letting off some steam with [the gentleman who was going to pick me up](https://www.reddit.com/r/gonewildstories/comments/4bdnhw/2_months_of_online_foreplay_culminate_gonewild), so I’m left to kill some time. I make my way to my Airbnb but grab lunch first. Horny and disappointed, I peruse the Craigslist Casual Encounters on the restaurant’s wi-fi. I’ve had exceptionally good luck with that back home, so why not see what a new city has to offer?

I find a couple of ads that appeal to me (tips for getting responses: post at least one picture – not of your dick, ideally it proves that you’re at least halfway in shape, don’t post “requirements” or “seeking” characteristics – c’mon dude you’re looking for some strange on CL: filter the responses yourself). One is a guy who’s in his late 30’s, and he’s apparently addressing the women who are dissatisfied at home, revealing that he is also dissatisfied with his married sex life. I can definitely empathize… which is the main reason I’m cruising random cock in this city, anyways. He also says he’s staying in a nicer hotel and would be able to host. Plus, his picture is pretty sploosh-worthy. Wearing only boxer briefs, it’s clear he has spent some time in a gym. I’m not into the Incredible Hulk-aspring “ermgerd gainz!” gym bro-type, to be clear. But I can appreciate the aesthetics and secondary benefits of a gentleman with a well-built physique. As far as I go, I’ve been told I’m “fun to throw around” or would be, due to my own petite build (5’1 / 100lbs, brunette for the record). Read more »