Tag: High School

Sharing a Monster Cock with my Friend [FFM]

Early into my junior year of college, I was watching Dirty Dancing and drinking box wine with my friend, “Nicole”. Nicole had just broken up with the guy she had “dated” since high school and needed some consoling. I say “dating” in quotes because she had basically been serially cheating on him for at least two years. Her ex was really straight edge: no drinking, no drugs, judge others about it, and not even religious. Nicole was not, so she would just get drunk on weekends and hook up with various guys.

 

Her “boyfriend” finally got wise and broke up with her, and Nicole took it hard, ergo the night of Swayze and Fran. Despite cheating on her ex **A LOT**, she wanted to get back at him. Now Nicole was short, maybe 5’2” but hourglass curvy, pale with big green eyes, and a huge mane of fiery red hair. Think Lindsay Lohan before cocaine, but with bigger hair and bigger boobs. She didn’t need to try to be able to hook up with whomever she wanted. *I just want to send him a pic of me fucking a giant dick* she says to me at some point. Read more »

Fucking my girlfriend on top of a mountain [M21/F21]

I’m going to give a bit of context, so if you want to skip that and get down to the juicy stuff, look for the row of asterisks (********).

I’ve been together with my girlfriend Rebecca for about five and a half years now, we got together about halfway through our final year at high school and immediately formed a connection so strong that we decided it was worth the risk to go to the same university and move in together once we graduated. Neither of us had been in a particularly serious relationship before; I had had three previous girlfriends, none of whom lasted more than a couple of months, whereas she had one that went nearly a year, but at any rate, we were both virgins when we got together (second base was as far as I had ever gotten, third for her). That didn’t last long. Read more »

[Group] What a birthday surprise to remember!!

So let me just say this from the start. Im a 24 years old trans girl. This story takes place when I was just a crossdresser. It was my 21 birthday and my best friend and I, Her name is Demi, same age as me and best friends since high school. She is a normal girl, born a girl at birth. We drove 4-6 hours to LA. I dont want to give specific locations because I dont want to plug anything. So the thing you have to know about Demi is that shes quite the out there person. Shes very vocal and loud but very fun and just an amazing person but very out there. So we got a hotel room and we did fun things all day and night. So after we finished all of that we were back at the hotel room around 9pm. She said the days not yet over and said follow her. So i did and we drove for 20 minutes to this house. I asked what was going on, and she said remember a few weeks ago when you went to the doctors? I said yes and part of the doctors checkup looks for STD and i was clean. Turns out she when the same day and she was clean and sent the results off to the owners of this home so we can get in. we get to the front and people awneser the door, and what i seen I will never forget. It was an orgy of people, like 20 or so, doing sexual things! Ive never been a huge sexual person but it was really hot!!! So we went in and the orgy was full of real girls and either trans or crossdresser, I couldn’t tell. I sat down on the couch and demi just said relax and have fun, as she started to suck my cock. I knew her for many years at this point and she never once did anything sexual to me. As shes doing this somebody comes over and i suck their cock while im getting mine sucked. This went on for like 2 hours. Sucking cocks, Licking pussy and tits, getting my cock sucked by two people at once. I never had sex with anybody that night but a few people licked my butthole, but no fingers. I was to shy for that to happen!! Demi only sucked my cock, i never did anything to her, but i seen other people having sex with her. Also got alot of cum on myself that night!! Me and Demi are still friends today and we talk and see eachother very often, 3 years after that experience. We never did anything sexual to each other after that day and weve never been back again, well atleast i haven’t!! I wont do it ever agian but im glad it happened!! What a surprise to remember!!

Four couple swap continued: My(M39) wild night with Gina(F38)

As a summary for those who may just be catching up, back in March, my wife and I started swapping with three other couples that were really good friends of ours. Each week over a period of just under a month, we each spent an evening one-on-one with another husband/wife than our own. The first four chapters in this ongoing narrative, covering our first and second night, are here:

[First chapter – describing how we started, and my night with our friend Karen] (https://www.reddit.com/r/gonewildstories/comments/509ln3/the_first_night_of_six_months_of_swapping_with_my/)

[Second chapter – continuation of the first night, discussing my wife Kristin’s night with Karen’s husband Scott](https://www.reddit.com/r/gonewildstories/comments/50hahx/mf_our_first_night_of_swapping_with_3_other/0)

[Third chapter – the next time we were together, describing my evening with the petite blonde Amy](https://www.reddit.com/r/gonewildstories/comments/510e4u/four_couple_swap_part_3_the_night_i_m39_and_a_my/)

[Fourth chapter – part two of the second night, my wife and Mike’s night together, and what happened in the evening and couple days after](https://www.reddit.com/r/gonewildstories/comments/51600v/four_couple_swap_continued_my_wife_f40_takes_our/) Read more »

I fucked [m]y friend’s [f]iance.

Throwaway because people know I Reddit.

A little background about myself. So this story began at the start of 2013. I just received a promotion that required me to relocate several states away. I was 33 at the time, single, never married, and no kids. I decided after a couple long term relationships that monogamy is not for me. I love dating new and different women. And I’m always up front with them and tell them I’m just looking for NSA dating. The women are more often than not OK with that, to start. I think they like the challenge of “oh, I can change him.”

I was pretty nerdy and fairly quiet in high school and college. After I started my career and got older, I started getting more confident and my success with the ladies just skyrocketed. It didn’t hurt that I had a nice job, made nice money, and dressed very well (shout out to /r/malefashionadvice). I’m not tall and don’t have a huge cock, I’m lucky to hit 6 inches on a good day, but the ladies don’t mind. I know for a fact because they always come back for more. Read more »

How I [M] got over a breakup by getting under the hot teenage bartender [F]

I had a really awkward and disappointing tinder date tonight. She was as pretty as her pictures but in person there was absolutely no chemistry what so ever. Its been a couple of weeks since I last got laid but there was no way tonight was going anywhere good. After bailing I ended up at home and started thinking about how well things could have gone – so here’s the first tinder date I ever had and definitely one of the best.

 

I was backpacking at the time, which is awesome and if you get the chance you should do it. I needed a couple of years to get my career and finances sorted so didn’t end up on a proper long trip till my late 20s but I had a blast and met plenty of older and younger people doing the same thing. Lots of people can articulate the massive character benefits of travel far more eloquently than I can so I’ll stick to the bit you’re probably interested in – its really easy to get laid. On top of there being cheap alcohol everywhere, people’s inhibitions are lower when there’s no chance their friends, family or colleagues will hear about what and who they’ve done. No responsibility, no reputation to worry about or appearance to keep up and an atmosphere that encourages constant hedonism tends to result in a lot more fun than normal. Read more »

[F/M/M] Summer Vacation: A Tale of Watersports, BJs, and threesomes.

One summer when I went home during college, I met up with a couple of guy friends from high school. I had already fucked one before back in high school (let’s call him Brad), but had never done anything with the other guy (and let’s call him Kyle).

Kyle worked part time at the Best Buy in our home town and Brad and I went to go pick him up. He was closing up that night so we waited in the back parking lot/loading dock. Kyle said closing up was taking longer than usual, and the case of beer we had in the trunk was getting warm. Probably shouldn’t have started drinking, since brad needed to drive, but we were being dumb. Brad and I had 2 beers before Kyle came out. He saw we were already drinking and he said he wanted to catch up. He shotgunned one beer and then chugged a second before opening a third to drink with us. Admittedly I’m a light weight and drinking makes me horny. I wasn’t really expecting to do anything that night though (but plans change ;) ) Read more »

A Different Flavour [MF/MFM] (First time post)

It was turning out to be a pretty normal week. I would wake up in the morning, have some breakfast, make lunch, walk the dog and, kiss my fiancee goodbye and head to work. I represent a large automotive parts manufacturer, working with the major manufacturers to make the parts they needed for when they needed them, a fairly repetitive job with few surprises. The week was progressing without any problems, and I was looking forward to the weekend.

Little did I know that soon I would be swept up in some serious relationship drama. My fiancee Lisa, had two best friends, Alex and Courtney, who both had serious party streaks. They had seemed to be settling down, both had lately given up the partying lifestyle to commit to long-term relationships. Alex had been with Adrian, a pretty cool guy who I got along with terrifically, for over a year now. Courtney had been dating a guy named Zack, who we secretly referred to as Harley for his insistence on riding his Harley-Davidson (sans muffler, might I add) to every event he attended, including a funeral for a high school friend of the girls. Read more »

The Timestop [Str8] [Fm] [school] [anal] [huml] [cuck] [nc] [Fdom] [Mdom]

(This is my first attempt at writing erotic fiction, or any other kind of fiction, so any and all feedback/criticism is welcome. As long as this does not get completely demolished there will be atlas a second chapter.)

Before I discovered my “talent”, I had lived an unextraordinary life. I had spent my first 5 years of high school with only a small handful of friends and was by no means one of the star pupils or “populars” that you would find in any school. Outside of school my life was equally plain. I played football but was not good enough for any team, mainly because I was extremely unfit, but not fat.

My family were moderately rich, my father a business owner, but not decadent by any means. So, whilst I got most of the things I wanted in life, I was not swimming in cash. The same could not be said about those at my school. The majority of them were extremely well off. The type that spent their summers in the bahamas and their winters in the alps. Many of them fit the normal stereotypes for rich ids too. Most of the boys excelled at rugby and cricket, and most of the girls were hot (as rich girls seem to be for some reason) and usually stuck up. Read more »

[M/F] Catching up with Smiles

Hey there, I wrote a couple days ago about [having first a threesome, then a foursome](https://reddit.com/r/gonewildstories/comments/4zzy1u/mmf_first_time_in_a_threesome_and_then_a_foursome/), make sure you read the comments on that post as well, there’s another two posts down there, maybe I should submit them separately. Last night I caught up with Smiles, and apologies again for the awful fake names. Read more »