Tag: Anal

[MF] Meeting after cheating

The [first part of the story](https://www.reddit.com/r/gonewildstories/comments/73t5w6/mf_sex_in_the_lobby_cheating/)

After some IM chatting, it turns out that Kristin had been written up for misconduct when someone saw us going at it in the lobby. She attended an all-female school with some old-school rules, and this was deemed “unladylike”. But, she really didn’t remember too much about the incident, and wanted to talk.

I agreed to come to her place, and started reviewing the night with her over a few drinks. I was really scared that she didn’t remember a thing, and that this would be a bad situation for me. She remembered me helping her at the bar, and drinking together, the walk home is where it got fuzzy.

“So, did we have sex?”

I explained that we tried, but I was too drunk to get hard enough.

“Was I too tight? It happens a lot. But, you went down on me, right? I say I remember cumming from that.”

I gave her every detail, and how she also went down on me. We then talked about how she knew my girlfriend, and might have classes with her when school was back in session. The drinks got me talking about how, maybe I knew it the relationship wouldn’t work, and it just seemed so right at the moment. Read more »

Looking for a Cabin in the Woods [MMF] [anal] [mast][oral][facials][piss]

I wanted a cabin in the woods. A little getaway from all of life’s difficulties. A place where I could sit back on my deck, look at the mountains and smoke a cigar in peace. I told a buddy of my plans and he said he’d go with me and we could scope out some properties. He was handy, so we’d be able to spruce up the place with ease over a few weekends.

We drove out to the mountains, walked into a real estate office and asked for help. A beautiful woman in high heels came over to us. She had curly blonde hair, muscular, long legs, and a beautiful smile. Freckles, too, on her cleavage.

“Hi boys,” she said with a smirk.

We told her what we wanted and she pulled up a few properties and pretty soon, we were off to see what the small mountain town had to offer. The first property was fine, but nothing special. The views were weak, but it had tons of property. As she walked from room to room, her heels clicking on the floor, she’d always toss us a sexy grin or wink. Read more »

[MF] Grown step sister and I decide to make our fantasies come true.

I’m 50 and my step sister is 46. My step-sister and I have always been close. We played around a little when we were younger but never had sex. She wanted to but I didn’t want to be her first. I wanted her first being the guy she would marry.

As we got older we both married and divorced several times and last year she divorced her last husband. We only live a few miles apart and since she got divorced she has been stopping by at least one a week to hang out and talk.

So a few weeks ago she stops by and somehow we end up on the topic of sex and what we like and tell her that I’m kinda glad I’m not married because I was starting to have problems staying hard and hated the side effects of the pills. She said she was sorry.

We talked about things we never got to try that we wished we had. She said she always wanted to try anal but both her ex-husbands thought it was gross. I told her I always wanted to be dominated but neither of my ex’s where into it. Read more »

Locked in and to Femininity [X-Post r/genderotica][OC][Bondage][NonCon][Gender Play][Anal]

A young man wakes up after a night of drinking, but his one night stand is not as temporary as (s)he thinks it is.

**Warning**, contains non-consensual scenes.

 

 

#Coupled

 

I awoke to a ringing inside my head, and blurred senses. Like any other friday night I had gone out on the town with my friends, and like any other saturday I was now feeling the repercussions. I groaned and blinked awake, expecting to see the clock at my bedside but instead was greeted by a blast of perfume and wavy blond locks. “Whatever happened last night, it was worth it” I thought. Hoping breakfast would keep her around long enough to get her number, I decided to fight the hangover, rise from bed, and start cooking.

 

Sitting up, my torso stiff and my chest heaving for air, my peripheral caught an odd glimpse as the covers slipped away. Swathed in maroon knit were two globes where my pecs should’ve been. Looking down at this foreign voluptuous chest, feeling the soft maroon turtleneck against my chin, a cascade of straight brunette fell past my cheeks and groped the sides of my chest. Panicking, I kicked my legs out from the covers, my black sheer stockings slid easily across the bed, my pleated skirt swished across my lap, and I heard my patent heels clack on the floor. Read more »

[MF] When I was 23, met a 46f nurse with a mom/son fetish in a motel…

After encountering an older woman online at a swingers site, I convinced myself to take a chance and meet her in one of my early swinger/open marriage type encounters. I flew back into town after a business trip and went straight to a motel in a small town. I waited for her and I was extremely nervous… our conversations had hinted that she had some particular kinks which I wasn’t sure how I felt about… basically she wanted to fantasize that I was her son and she really wanted to eat my ass. Ok!

I was about 200lbs, 6 feet tall, and thickly hung. She was a redhead nurse with large tits and a little too much makeup. She looked better in person as I watched her walk towards to motel from my second story window. I was very young and inexperienced so I was very nervous.

She knocked on the door and I let her in. We exchanged pleasantries and I had a hard time keeping my eyes off her chest… they were quite large. She wasn’t a super model but she definitely exuded the “milf/cougar” stereotype and spoke to me in a very caring manner. Even her purse looked like a mom’s purse to me. We really didn’t talk long before things got heated… Read more »

Forbidden Love, Watersports [M] [F] [anal] [fist]

FORBIDDEN LOVE, GOLDEN SHOWERS, AND FACE FUCKING

I want a woman I do not know. Well, we’re Facebook friends in that roundabout way. A mutual friend posted something that we both commented on. We got into a lengthy chat. I friended her. She accepted. From then on, we had this one little inside joke about always wanting a Big Mac cheat meal for dinner. One day she posted an article she’d written. I’m a journalist and I often need contributors, so I messaged her. We got to talking and she ended up contributing a few articles.

Her articles were great. She was beautiful. She was also married and had children. And I had a partner. I’d say girlfriend, but she always got upset with that word and since I wasn’t the marrying type, we compromised on “partner.”

One day, this “friend” posted something on Facebook about depression and anxiety. I could relate. We got to talking. She said her marriage was in big time trouble. They’d just grown apart. Things weren’t going the way she had wanted and so, in order to be clear headed, she decided to visit a therapist to decide if a divorce was best. Read more »

My Craziest Weekend: Part 3 – Sunday [MF] [with extra helpers] [long]

[Part 1](https://www.reddit.com/r/gonewildstories/comments/73y0wp/my_craziest_weekend_part_1_friday_mf_long)

[Part 2](https://www.reddit.com/r/gonewildstories/comments/744fig/my_craziest_weekend_part_2_saturday_mff_long/)

**Sunday**

When I woke up the next morning, Anna and Megan offered me some coffee, which I accepted with thanks. The last two days had been crazy and I felt off to say the least. In a way it was all like it happened to another me in my head, or so it felt. I wasn’t talking much as I drank my coffee and left the girls to their chatter. By this point I felt more than a little awkward, still being in essentially a strange household and sleeping my way through the residents systematically. I showered again, with the blessing of the girls.

My plan to leave after that, died with the arrival of Emma, who had spent the night at George’s place. We were standing in their kitchen. She was of course wondering, what I was still or again there. I could just utter a very lame “ehm”, not knowing what to say or do by this point. Anna and Megan though told their housemate about the day before. They were very detailed about it. Telling Emma I had fucked them all afternoon. Which was of course blatantly overstated. I had slept with them, though there were longer pauses for food we ordered and when the girls were just playing with each other, so I could calm down and join the fun again. Read more »

[MF] Taking my ex-nieces anal virginity

As some of you may remember I wrote a few weeks back about fucking my [ex-niece for the first time](https://www.reddit.com/r/gonewildstories/comments/6r6u32/mf_unexpected_sex_with_an_exrelative/?st=J8AU489B&sh=563c3e37https://www.reddit.com/r/gonewildstories/comments/6r6u32/mf_unexpected_sex_with_an_exrelative/?st=J8AU489B&sh=563c3e37), here is our most recently time fucking.

Brooke recent broke up with her boyfriend and had to find a new place to live. After she had been crashing a her friends places for a few days I offered up my spare bedroom, which she accepted.

She gets her stuff moved in, and her and I do not really see each other, other then in passing, for a couple of weeks. One Friday night she has the night off and I am home from work, her and I are sitting on the couch watching tv and drinking some wine. The show wasn’t too interesting so we get to talking about her ex and why they broke up. She tells me about all the stupid stuff he was doing and how he was annoying her. Then she brings up that the sex sucked. That she rarely got to cum from sex, but rather had to finger herself afterwards.

After that statement she gets up to go to the bathroom and I go get another bottle of wine. Read more »

Ex-wife stories 1: Can’t believe this worked. [MF]

My ex-wife and I had a lot of problems, but none of them were in the bedroom. As best as I can remember, I’ll start with the story of how I got her to lose some inhibitions…

First, the usual descriptions. My ex is a natural redhead, who, throughout our time together, weighed about 100-110 lbs, and has B to small C cup tits and a decent ass. I’m a little heavier than average, with an average sized cock. We usually had pretty intense sex, often lasting 1-1 1/2 hours with multiple orgasms for her. Since I am both a gentleman and a pervert, my bedroom rule is if it feels good, do it. She often got nervous trying new things, but once she got over her initial nervousness, there was very little she didn’t like. One night we decided to try something different, to attempt to remove some of her inhibitions (again, apologies if I forget something or it seems out of sync, this was 3-5 years ago). Read more »

[MM] I had anal sex with my wife’s brother

My brother in-law was in town for the weekend and was staying with my wife and i. There has always been a connection between us but I thought it was just because we were close growing up.
After dinner we had a long conversation at the dining table and while my wife was talking about her work and I felt a leg brushing up and down my foot. I assumed it was my wife and smiled at her but then my brother in-law coughed and I looked over at him and he nodded to under the table and continued to rub. I instantly got an erection and could not hide it, my face went red. Through the conversation he slipped his hand on my thigh without my wife noticing and I almost reached orgasm after 5 minutes.
After our conversation we decided to clean up and head to bed. He pulled me aside and told me has been fantasizing about having anal sex with me all night. I knew this was going to come up near the end of the night but was still shocked!
We agreed on a time to make sure the wife was asleep. When the time came I looked over and she was sound asleep. I met up with him and we stripped our clothes off right away, we breathing heavily, and sweat sweat sweat!!!
He bottomed and it lasted about 8 minutes, I have never orgasmed that strong in my life. I came inside of his asshole and pulled out and then dribbled on his back. He told me to wipe it off and feed it to him and so I did. It was the best feeling in my life. I sucked him off after this and he finished on my face, I licked it up because he did that with me but it didn’t taste good. We spooned for about an hour then I went back into my bed.
I’m writing this the next morning so it happened last night. My wife and brother in-law haven’t woken up. Don’t know what will happen. Wish me luck!