Happy memorial day weekend. Long time lurker, first time anon poster. Didn’t realize I had to wait 24 hours before posting so enjoy this series!
Category: gonewildstories
Fucking my friends girlfriend (cheating) [MF]
I had known Sammie for a few years when this story occurred, her boyfriend and I were good friends and we hung out a lot shooting pool and throwing darts at our local watering hole. I don’t really remember how it all got started, but I do remember that Sammie and I chatted on the good book on a daily basis about everything, from the mundane to the sexual. One day while chatting on the good book, she mentioned how that she needed money to pay a couple of bills and was wondering if I could help her out. I got brave and said, sure but I would like naked pictures of her in return instead of her paying me back with money. After some negotiation she agreed on sending a couple of pics of her boobs a butt picture and picture of her pussy, but of course her boyfriend couldn’t know.
[MF] Starting on the ride home
We drove home with the Jeep top down. My hand way up her skirt on her thigh. My pinkie finger resting against the material of her red underwear. Rubbing a bit at first. By the time we were almost home she was reaching from her seat to play with my cock through my shorts and I was pushing on her clit.
Back home we sat together and watched TV. Her back to me. My hand over her shoulder playing with her breast. Feeling her nipple. Pulling on it. She would kiss my arm and pull my hand up to suck my thumb. My hand went under her skirt and inside her red underwear again. Her hand joined. I told her I wanted to 69 later. She said she wanted that and we should go now.
We stripped naked and in bed she started to suck my dick. I laid back and she straddled my face. She came. And we kept going but now side by side. Finally we rolled completely over and I was on top.
After her third orgasm we stopped and she began to jerk me off. I sucked her breasts and came all over her stomach.
[FM] How I met and fucked my sister’s friend
Long time lurker, first time poster. This story happened 2 years back when I was interning in Boston during college. I have two younger step sisters who were in high school at that time. I am three years elder to my elder step sister. So, when she was starting senior year I was starting my junior year in college. This happened during the summer before the junior year.
Although my dad’s family lived in Boston, I hardly visited them during my internship. I was staying with a bunch of college friends who were also interning. As a result I only went to visit him mostly during weekends or at random times. I still had the keys to the house and my own room though. I didn’t have much association with my step sisters as we didn’t grow up together. I am not a jerk and thankfully they aren’t either. So, even though we weren’t close like siblings, we weren’t in any bad terms.
[MF] My sister’s conservative friend
Long time lurker, first time poster. This story happened 2 years back when I was interning in Boston during college. I have two younger step sisters who were in high school at that time. I am three years elder to my elder step sister. So, when she was starting senior year I was starting my junior year in college. This happened during the summer before the junior year.
Although my dad’s family lived in Boston, I hardly visited them during my internship. I was staying with a bunch of college friends who were also interning. As a result I only went to visit him mostly during weekends or at random times. I still had the keys to the house and my own room though. I didn’t have much association with my step sisters as we didn’t grow up together. I am not a jerk and thankfully they aren’t either. So, even though we weren’t close like siblings, we weren’t in any bad terms.
Wuss and Pansy [MF]
First time poster, long time lurker.
Wuss and I (Pansy) met via Tinder. If you want to get to the sex part, skip this introduction part.
I was bored and away from family, friends cause of work. He was from the states and apparently also bored. I found him to be clever and funny, goofy and dorky even sometimes which then I found to be quite amusing. After exchanging messages for days, I asked him if he wanna tag along my trekking trip that weekend. I was surprised he said yes, knowing that he’s used to cold weather and it can be extremely hot out.
He was a few inches taller than me (I’m 5’1), darker and with wide shoulders, a dad bod and amused eyes. When I saw him, I immediately thought he looked dorky but also hoped he wouldn’t slow me down. This was my first time meeting a guy from Tinder so I was absolutely nervous.
We finished the trek after a considerable slow pace, only because we got lost a bit and he did slow me down too. I forgave him after he shared his food with me though. Haha!
My own Mario Kart success[FM]
The other Mario Kart story reminded me of this. So I wanted to give it its own post.\
A couple of years ago I was using tinder to meet this girl, one of my pictures has a background of the place I work, and she recognized it and liked me, she was a 9/10 for me. Five feet tall, D Cup, perky butt from being an athlete most of her life, and couldn’t have been more than 120 pounds. After a little conversation about my job, some flirting and talking about where she goes to college we arranged a date! Went for dinner and some ice cream after. Our conversations led to hobbies, and I told her I was into video games, mostly computer games but I was generally better than the average person. She countered with how good she was at Mario Kart and how I had no chance at beating her because she practiced in the dorms. Dinner is ending and I was about to drive her home when I remembered we had just gotten a Wii at my work with the newest Mario Kart game and I told her about it, said we could go play a few rounds and I’d drop her off after. She seemed eager to prove her claim so we went!
[MF] Wife’s sister accidental flashing?
So, as the title suggests, I’m suddenly thinking about this as a serious question…
I’ve written in the past about my wife’s sister. TL;DR she called me up to her room to bring something to her, and she was at her dresser getting PJs on or something, tits out. No way she didn’t hear me coming.
Since then, over the past two years or so, little things have happened that I honestly didn’t second guess. This past Christmas, for example, we took a family photo. This was Christmas morning, and we still do Christmas morning in PJs. She is short, and got in front of us for the phptos. We all joked about doing a funny “sorority squat” photo, and she pushed her ass right into my crotch. Nobody notices based on the angle, and that I was in the back on the end. She never said a word and didn’t even look at me.
My first R4R experience resulted in the hottest [MFF] threesome…I am very excited for my next tryst!
I am a 32 year old woman. And I have a very good looking FWB. Him [37 male] and I have been fucking for the last 3 years. He had been mentioning a threesome for a while and it just never worked out for us. I had been trying to find a girl on Tinder but that is pretty much impossible, as the minute any girl reads “threesome”, she unmatches. So I tried my luck with R4R and I hit the jack-pot. We got a beautiful 24 year old petite Asian girl with natural D’s, sexy face, long hair…seriously so hot. She came over to my apartment the next night where she and I chatted. There was some drinking and weed smoking to loosen us both up. He was running late (what guy runs late to his own threesome?!?!?) because he wanted to have a few drinks with his friends at the bar to “loosen up”. He finally arrived and the two of us were good and tipsy. There was a lot of touching and blowing smoke into each other’s mouth, when finally our guest suggested we go to the bedroom. We all couldn’t get our clothes off quickly enough. Her and I started kissing and fondling each other’s breasts. Then we all started kissing each other. Next thing you know, her and I are going to town on his dick, switching off between one sucking his balls and the other sucking his shaft. I remember looking up at him and his eyes were rolled so far back in his head. She said she wanted to watch him fuck me, so he did start pounding me doggystyle as she watched. After a few minutes of that, I felt like she was being ignored, so I shifted my body over so my face was in her pussy and I lapped up her cunt as he pounded me from behind. She eventually came all over my face and then proceeded to lick it off. This made him very abruptly switch from fucking me to fucking her. He wanted her on top so he could watch her amazing tits bounce up and down. I moved behind them and would occasionally pull his dick out of her pussy, suck it and put it back in. We changed positions a few more times and finished with him spraying his load over both of our faces.
[MFF] My first girlfriend constantly tested me.
I’m going to preface this by saying that this was one of the more strange sexual encounters I’ve had in my life.
I lost my virginity to a girl that I have known practically my entire life. We went to the same school from first to eighth grade, and then went to the same high school together. Despite the fact, I was never really close with her until my senior year. In all honesty, I had always thought she was kind of annoying. She was the artsy type, not that there’s necessarily a problem with that, but she was always very pompous about it. She acted very snobbish and cultured, and constantly critiqued and attacked people for their taste in music, movies, and books.
I first got to know her on a personal level when there were only two or three months left in my senior year of high school. I was paired with her and some other people to work on a project. I really wasn’t looking forward to it, namely because I was paired with her, and the other people I was paired with were burnouts who didn’t do shit. We quickly came to this realization, and agreed to work on it together.