Category: gonewildstories

An un[f]orgetable [m]orning with Annabelle

This story is quite long but one of my favorite experiences ever. This will be my first post here. Part of it has been posted on another site but I have made some edits and added some sections that weren’t previously included. Here is a little about me physically: I’m 6’6”, 240lbs, hairy, with a short beard, brown eyes, short brown hair, glasses, and a 6.5” inch cut cock. Hope you enjoy!

Annabelle and I started chatting online on a Tuesday evening in the middle of March. She responded to my online posting looking for a woman who was interested in, to put it bluntly as I did in the ad, having me finger her to orgasm.

Annabelle quickly introduced herself as a graduate student studying in the city. She sent me a photo of just her long, slender legs peaking out from under a nearly knee-length black dress, ending in a pair of perfectly manicured feet in orange-strapped sandals. As soon as the attachment opened I felt the raw lust building and growing inside me. I collected myself and quickly responded, asking when we could meet in person. She agreed that we should get together, but despite my pleading she wasn’t free that night, or Wednesday, or even Thursday. Friday though, Friday morning she wanted to meet. Read more »

Desires Cancun Mexico

True Story. Not group sex per se but certainly nudity and sex in a general group.

I had been trying to get my wife to agree to going to a resort where nudity was allowed. I kept telling her that if she did not feel comfortable she did not have to be naked at these places. My hope was that I could at least convince her to go topless after a day in the sun and drinking. She eventually said she would think about it so I sent her links to various clothing optional resorts, mostly outside the U.S. to limit the chance of running into someone we know. To my surprise she agreed to go and picked Desire’s near Cancun, Mexico.

When we got there everyone was completely naked. Not a single dressed or topless person. Everyone was completely naked but acted as if everything was normal, hanging out at the pool, grabbing lunch, and playing volleyball. There were no sexual overtones to it. My wife got naked immediately. She actually seemed more comfortable with it than I did. Then came dinner where people got dressed up but in very sexual clothing. Take the same woman completely naked swimming in the pool with no sexual overtones and then put her in a sexy see-thru dress and suddenly it feels scandalous. Read more »

(M)y de(f)erred fantasy; hooking up four years later

I’m a senior in college and it’s 2009. Sadly, at this point in my life, still a virgin. This is something I held close to my chest for obvious reasons. You’re probably envisioning a pimply geek at this point, but this is also why I kept this so secret – it was a complete contrast to the way I looked and acted.

I was a wrestler throughout college, so I was extremely fit. I’m 6’1, was about 200 pounds at this point and pretty much solid muscle. I was “hot,” but painfully shy and introverted. I didn’t know I was “hot” yet. Even talking to women in class would make me nervous beyond belief. Most people I knew just assumed I crushed pussy, but I was completely futile in pursuing women. Beyond some kissing, my sole sexual experience was eating a girl out earlier that year – that was it. Read more »

Visiting Another College [21M/22F 21F]

I just discovered this sub and it has quickly grown to my favorite. I will share one of my stories now.

After graduating from my community college, I decided to go to a university out of state. I chose an engineering school that basically had a 90% guy to 10% girl ratio and I knew absolutely no one so I kept in close contact with a lot of people from my hometown. One of the people that I kept in contact with was my ex Katie. We were high school sweethearts and after we broke up my senior year, we would get together every once in a while and still hook up. I was the first person to sleep with her and she was very shy so she didn’t want to sleep around. It is also important to note that she did not drink or anything and was a very religious girl while we were dating. (Besides the fact the we were having sex) Read more »

Dirty Internet Adventures Part 2: Searching for a roommate goes wrong, then right at night!

EDIT: I may have posted this before, but I am making it part of this series.

I have been a closet pervert in my whole life. While, most people think of me as a normal and functioning member of society, they could not be anymore wrong, I have slept with a lot of women and most of them I met online. Of course, sleeping with women that you know you will sleep with is exciting, but nothing compares with sex adventures that was totally unexpected and here is a story of an unexpected sex!

I may be a perv but I am a hard working perv. I work early in the morning til almost midnight, and sometimes I have to work over the weekends. So, you can say I make a lot of money. As a young single guy, who has a lot of money, only thing I can spend it on is having a big house. After awhile, though, living alone in a big house gets a little lonely, and I thought it would be cool if I could have a pretty attractive female living with me and I was willing to give a good price. Read more »

[M]y first time at a gang bang

TL:DR Rambling story of a gang bang. Probably too much time spent explaining the scene and not enough action. Like an EDM song that never drops the beat.

This is my first story on here. It was a cool experience in my life and I recommend that you go out and try something similar one day. This is a true story. The core of it, I remember well. The details of what happened around me are probably a mix of what happened that night and what happened on other occasions at this same place.

I’m a normal looking guy. I could describe myself, but lets be honest. If you are a dude, you are going to put yourself as the star of the story anyway. And you should be the star of every story. Go enjoy life. I have been to swinger clubs in Europe several times. Normally, I bring a woman with me. We usually don’t swap. It might sound weird, but you can have a crazy sex life at swinger clubs and not fuck a lot of people. This time, however, I went alone. I was in a casual FWB relationship. No cheating for me. I even asked her if she wanted to come. The answer was the normal one that women give to that question. She smiled, looked me in the eyes, and said, “I … um … maybe? … no? … next time … maybe?” I always say, “if you change your mind, let me know.” I have asked a few different women and it usually goes like that. This is not something that I would pressure a woman into, even if she seems to want to go. Read more »

First Time Post– (M)y (F)irst time with a Bi-Sexual Female Professional Soccer Player ( 21m/ 26f)

Background: This story took place 5 years ago. I’m a long-time lurker to this thread and decided to give this a whirl myself. This is one of my favorite sexual encounters and was sparked by seeing an old Facebook photo from that night.

In 2010 I was a senior in college where I spent 25 hours a week as a “practice” player for a major Division 1 women’s soccer program. (I would participate in training sessions with the girls when they were short-handed due to injuries, illness, etc…) I used to be decent at soccer and this was a great way to stay in shape and hang out with extremely fit college girls every day. :)

This is my story of how I met Sarah who was a former player at this university. She was training with the team for 4 months during her off-season with a women’s professional team in the United States, while her girlfriend was training with a national team in Europe for the Women’s World Cup.

Sarah: 5,7′ inches, 125 lbs, green eyes, shoulder-length brown hair, 6 pack-abs, and extremely toned arms. She had perky B-cup tits with muscular legs and a firm ass. She is extremely outgoing, confident, and when she drinks all of those qualities are amplified. Read more »

[M]arried business man, [F]un, but without tinder this time. Part 5 – the dancer (long)

I’m typing this from my mobile so I apologize for typos and formatting errors ahead of time.

This particular night started out perfect. My wife told me she wanted to go out for drinks and have a little fun. Our work weeks are always stressful so I was looking forward to enjoying my wife’s company. My wife is 5’6 110 lbs, very petite, has long wavy dark hair and a beautiful smile. Her body is gorgeous (she is a lifestyle coach/personal trainer and owns her own gym). S, needless to say I had a pep in my step on the way home knowing I was going to get to see my wife in something sexy tonight. Read more »

Long night, longer morning – Fun times in Las Terrenas [M30/F27]

First time post. Been a lurker here for a while. My gf, Monica, wanted me to post one of our stories after she found me reading this subreddit in bed from my phone with a huge boner (I thought she was sleeping…) So here it goes:

Its around midnight in the beach town of Las Terrenas, in the north coast of a caribean island. Monica and me go pick up Sean and a famous house DJ from the US that we will call Diva. We have to go to the venue where Diva will play. We´re all looking forward to have a good time.

Monica, is half european half latin, and she is smoking hot. She has a very tanned skin tone, blonde hair, long and fit legs, big and firm breasts (34dd maybe). And that night she had black shorts and a black top.

We have blast. Our DJ friend, Diva, killed it. Everybody was having a good time dancing and partying. There was a lot of molly going around, and you could get this big sexual vibe from the crowd (around 30 people). Read more »

First night at college ended with two cocks[M] in my[T(MtF)] mouth [Group]

Back in early college I was quite a party girl. Even though I started feeling and behaving like a girl early on in life, I was for the most part a closet gay crossdresser until high school. Being a short and super thin Asian boy with soft skin helped me pass off without the aid of hormones so I was relatively confident in my looks unlike most trans-girls that age. When I turned 15 I began transitioning but even before then I was always mistaken for a girl.

College was a fresh start and I totally embraced it! I could be me, the real me for the first time in my life and as such I was so ready to let myself experience men and the attraction I had for them that was always suppressed due to the fact that everyone in my small town knew I was not a cis girl. While I had dated guys in high school, we always had to keep it relatively secretive because well, it was high school in the late 2000’s and kids were jerks! Read more »