The first time I fucked her ass [MF]

This is a third story from my past. It involves my wife and I when we were dating and is completely true. Again, this store can stand on its own, but there is background in [part 1](https://www.reddit.com/r/gonewildstories/comments/4d088e/an_introduction_and_our_first_time_mf/) and [part 2](https://www.reddit.com/r/gonewildstories/comments/4d6ktn/getting_her_into_anal_mf/).

We’re both ealry 20s in this story, I (Brendan) am 5’10, 175lbs. Brown hair, blue eyes. Jenn is 5’6″, 125lbs, brown hair, blue eyes.

One night a couple of days into the fall semester, Jenn came over to my dorm. We had some drinks while waiting to meet up with friends at a party later that night. Being in our early 20s, newly dating, and helped by a little bit of alcohol, we got horny and started making out.

I had a single bedroom to myself in a two bedroom apartment, so we didn’t have to worry about roommates of being walked in on. We quickly shed our clothes and within minutes were naked in bed while we kissed. I’m crazy about Jenn’s tits. They’re B-cup, super perky, and have these super sensitive nipples. Any time I have her shirt off, I immediately suck on them, and this time was no different. As I sucked on her tits, I used one free hand to rub her clit, and she reached down and played with my cock. Read more »

[F]inding my inner cougar

I heard his footsteps sprint up the stairwell and braced myself to pounce. I was the kind of distracted horny that only women in their late 30s understand. I’d spent all day fantasising about cum all over me and inside me. I’d been used in alleyways, thrown around at stag parties and spread my arse cheeks to feel hot jets of cum shoot all over my aching holes. Both of my hands were getting sore from playing with myself and porn just made it worse. I needed a real cock to play with.

A 22 year old PE teacher pursued me online last year. I’ve never had cougar urges, despite friends enthusiastically telling me to try it, so he persisted, and I resisted. Curiosity almost got the better of me a few times…

Then he messaged me a few months ago saying, “I’m 23 now…” and something inside me was coming around to the idea… It turns out he lives on the same street as me and the convenience of this, plus his enthusiastic pursuit, eventually met with the tsumani of horniness I was surfing. Read more »

My first R4R success from Reddit [M28/F38]

My experience actually happened about a year ago.

I had responded to a post on my local R4R here on Reddit from a woman who mentioned she was going to be in town for a few weeks, and wanted to possibly meet a local and have some no strings attached fun.

Now I know it seems like a majority of the time, whenever a F4M post pops up, it immediately gets a lot of attention since it’s one of the few among all the M4F posts. Even more when they’re upfront about sex in general, so I figured “the worst” thing that could happen is that I simply don’t get a response, right? Besides, you won’t know what could happen if you don’t even try.

So I send her a reply and don’t get one back. I think “oh well”, and just continue moving forward. About 3 days after I sent it, I see the orange envelope pop up when I log in. I was almost certain it had to be her, as I had not responded to anyone else within that time frame. Read more »

My first attempt at writing anything ever: An untitled project [Fantasy] [Sadistic] [Futa] [Rape] [ff] [murder]

*NOTE BEFORE READING. This is the first time I’ve ever taken the time to write anything and I would love to see any constructive criticism. If this is well recieved I might make this a series. ALSO A SERIOUS WARNING. The following story contains hardcore rape, sadism, futanari, and murder. If this is not for you then I urge you not read it. Don’t judge me :(

Somebody has to cater to the crazies.*

THE STORY

“Please. Please. I need to eat something.” the woman wheezes to me naked and face stained with dried tears. She pulls lightly on the chains binding her hands trying to break free with the little strength she has left. Her lungs fill with the heavy, dusty air that she’s been familiarising herself with for the past few days. “I don’t even know what you want or even what you are?”
“You know, I’m not quite sure myself,” I say from the shadows watching as her head can barely keep itself up, “I’ve never really seen anyone of the same race. Nobody has. I’ve heard someone call me a lizard-girl once so I think I’ll stick with that.”
“Look, I’ve learnt my lesson. I’ve learnt it four days ago. I swear I will never get in your way again. I will even help you if you want.” She pleas. Read more »

Cuckold with Girlfriend and Mistress (part 1)

Sam came into the gas station holding Lauren’s hand affectionately, already walking towards the register. Both were wearing skimpy shorts from my apartment, Sam wearing one of my undershirts and Lauren a tank top. Their hair was disheveled and it was quite clear that neither were wearing a bra or panties; Lauren’s perky erect nipples pointed out of the thin cloth with her C cups spilling out the sides of the top. From a profile view her tits bounced and swayed, easily visible. Sam’s choice of undershirt proved to be tiny on her larger body, barely covering her smaller but equally surreal tits. Both of their asses spilled out of the shorts, and the outline of their pussy lips were defined, sticking as if already moist.

“You didn’t think I would do it, and that’s exactly why I fucked your girlfriend gay, Chris. I drove all the way from Georgia just to humiliate you. Ever since that conversation, I have been talking to your girlfriend behind your back. First, we became friends and then I slowly started bringing up my bisexuality. It was actually pretty easy to convince her to try it,” Sam said matter-of-factly, taunting me: “you must have been pretty fucking pathetic in bed.” Read more »

Fucking my fuck buddy’s buddy [MFM]

I [first posted](https://www.reddit.com/r/gonewildstories/comments/3z1hox/designated_drivers_unite_mf/) here back on New Year’s about hooking up with a younger guy, Ryan (I’m 36, he was 24). What I thought was going to be a one night stand has turned into a fuck buddy situation over the last few months. Although Ryan is far too young for me to date regularly, we have amazing sex, and usually end up fucking at least once a week. We took a few weeks off in March because I started dating a guy who turned out to be an ass. Once that ended (like literally the night it ended), Ryan and I started fucking again, and maybe it was just because I missed him or the other guy I’d been dating was so lame, but our sex right after my breakup was better than ever. He noticed it, too, because he said something about it, about how I seemed even more passionate than I had been before. That eventually led to him asking if I’d ever consider having another guy join in. Read more »

Surprise Encounter Part 5 [Mf]

I emerge from the bathroom to find her in my bed. I smile, taking in the sight. She is face down in the pillows breathing softly. I run my hand over her knee highs as I approach. Softly I caress her ass and she shudders slightly as I trace the handprint that remains. As I make my way up her back she moans quietly into my pillow and wiggles her ass. And like that, I want her again. I lay down next to her and she turns to reveal a sly smile.

“You look like the cat who got the canary,” I muse.

“I feel like that cat,” she laughs and buries her head in the pillow.

I am weak, but blissfully content. I would fuck her again in a second, but I need to hold back at least for now. I place my hand on her back and feel the rhythmic rise and fall of her breathing. I forgot how much I miss little moments like this. Her smell, her warmth, her breath can all be very intoxicating.

“These pillows smell like you,” she mummers through the fabric. Read more »

Dennis Goes Camping Part 1: The Swamp M/F

Camping. Jim wanted to go camping.

Dennis hadn’t been camping since he was thirteen. So almost a decade ago. He associated it with screaming former drill sergeants and forced push-up regimes. He didn’t associate it with nature. Fuck no. Read more »

From omegle stranger to in person hookup [20F/35M] (Part 1 of 2)

After I broke up with my first boyfriend, I was pretty sad but at the same time very horny. Quite honestly, he didn’t fulfill my sexual needs- he refused to go down on me, barely sucked on my nipples, constantly needed help staying hard (probably due to all his porn). However, he was the one I lost all my ‘firsts’ to- first kiss, blowjob, sex, etc. After we broke up, I couldn’t help but crave real sex, which he gave me a taste of. Now, I am a shy Asian girl with very little experience, so something like tinder or a bar hook up was too much for me. So, I turned to omegle. Read more »