Category: gonewildstories

I finally [f]ooled around with my handso[m]e older friend/former boss.

I first met Chet 5 years ago at a work related event at a bar. I was a cute little 24 year old in ripped tights and a short dress, and he was a very handsome 40 year old man, well dressed in a casual suit. We chatted for a bit while I smoked a cigarette, thinking I was being so charming and adult, and we’ve been friends ever since.

Im tall, long legs, a bit of a belly but nothing crazy, perky smallish boobs, long dark hair and a pretty face. With these features I’m certainly not everyone’s type, but the guys who are into it think I’m hot haha. I’m in a creative field and am used to hooking up with guys who are like me, grungy and disheveled, which I love! But Chet is different, an executive at a financial company, he wears suits and nice clothes, combs his full head of thick gray hair back and parted, and he looks a lot like a less-heavy Alec Baldwin in 30 rock. It drives me crazy. The first few years I knew him it was as a casual friend. He’s interested in my creative field and would show up to lots of my work related events to drink with me and my friends in the same field. Read more »

Sex on the beach [MF] with a bit of a twist.

I have never been a fan of condoms and we had been having unprotected sex for quite a while. She was on birth control so it wasn’t really an issue and we were both disease free. The sensations I get bare just do not compare to being wrapped up. Don’t get me wrong sex with a condom is better than no sex but I have broken more than a few condoms so I really do not trust them anyhow. When she went off the pill and told me to cum inside her though…

Sure I had imagined sex with her pregnant, but actually seeking it out, intentionally trying to breed her. That just turned me on so much. I really started pounding her and pushed myself to orgasm as deep inside her as I could. It was great, most orgasms are, but that was special. Like the first time you have a simultaneous orgasm with a partner and it just blows your mind.

It actually took quite some time before my seed took hold in her belly. Which was a bit of a surprise as we had sex at least a few times a week, if not more, and I always came inside her. But when she finally showed me the positive test kit we were both super excited. Read more »

I (23/F) Cheated with my Snowboard Instructor [MF]

This was just last week. I’ve been thinking about it every since, and obviously can’t talk to anyone about it so I figured this would be a good way to share since it was one of the most amazing experiences of my life!

We were on a ski/snowboarding trip in the mountains in BC (that’s about as specific as I will get to protect his identity). It was my fiance and I, as well as a few of his friends and one of their girlfriends. We rented a condo right on the hill, so it was 5 days of skiing, hot tubbing and drinks. My fiance both skis and snowboards, where as I am an experienced skier that just this year is attempting to learn to snowboard. I skied for the first 2 days, then on the 3rd day, my fiance agreed to hang back from the rest of the group and try teach me to board. That’s where thing started to go wrong! It’d be an understatement to say it didn’t come natural to me, and I could tell he was getting frustrated, then I was getting frustrated at his frustration and my inability to catch on. By the end of the day, I had enough and I’m pretty sure he was regretting getting me the snowboard for Christmas. We were barely talking to each other. Read more »

[Group]Thanks for the Treat

I was forever a shy teenager who’d gotten more than expected attention from boys for my gorgeous body under those sweats. Fairly tall at 5’11”, strawberry blonde waves and a 34C over a 24inch waist with an applebottom (my nickname with friends) didn’t distract me enough to pursue my education very very seriously and I’d had no time left for a boyfriend. After graduation, I landed my first real job as a teacher and went out boozing mid week to celebrate with my best friend Annie. Before leaving home, she’d emotionally blackmailed me to promise I’d let go of my inhibitions for the night if I cared for her, though the night had been pretty tame. It was late, I wasn’t very drunk yet and Annie being the wild child she is was having her go at some stranger on the dance floor. As I sat fiddling with my drink at the bar, a tall sharply dressed man plopped on the seat beside me. “So, you ready for it?” he looked at me with a twinkle in his eyes. I gave him a sharp stare and said nothing,that sounded shady as hell. But then the man nodded his head towards the dancing Annie and repeated “You must’ve heard of it?” which is when it hit me Annie might’ve set me up for some wild dares. Feeling quite reckless before my mundane job routine began, I replied “Yeah, I’m up for it”. I must’ve been hit up more than I thought, for I signed a document he conjured up the next instant. It looked legal enough and I was waiving off rights to press charges for what I was partaking would result to but I figured it was just some part of a kinky game. Read more »

[FM] The Taste Of Cock For A Virgin

Before I begin to narrate my sex story, I’d like to tell my readers that of all things that they surround themselves with, the most basic instinct is the primal instinct of sexual pleasure and I’ve known it through my multiple adventures as I ventured into a world where pleasure isn’t restrained or controlled in any form and in that world, I found myself in the true form, the animal form. Naturally, the reader wants to have an image in mind to be able to envision all my narrations.

I’m a 24-year-old girl of Indian origin and I work in a blog as a content writer, our blog became recently very famous because of the ground-breaking and exposing work we did to reveal the drug mafia operating in the underworld of New Delhi, which is where I stay.

I’m taller than the Indian standards for a woman; I’m around 5 feet 9 inches and at first look, a person might not even notice me. I’m fair in complexion, have curly dark hair and a petite figure. Read more »

Fucked My Freshman Year R.A. [MF]

On the first day of my freshman year of college, I met Kate. Kate was my R.A. I moved in to my dorm a week early, so there was almost nobody else on my floor, aside from Kate. She and I hung out in my dorm each night that week, just chatting and getting to know each other. It was really cool. Kate was a great R.A. She was pretty chill about a lot of stuff, but not to the point where she was just not doing her job. If we pulled some stupid shit, we would get called out on it. But I never did anything to get in any trouble. I don’t drink or smoke or anything like that, so Kate and I remained on good terms. At the end of the year, she thanked me for being the only resident that she never even had to have a talk with. Anytime we interacted, it was always for good reasons. Kate and I were both involved in theatre, and during a particular show we were doing, her character had to give mine a lap dance. We always joked how if her higher-ups found out about it, she would get fired. Read more »

Our First Date [MF]

C and I met 2 months ago. She’s 19 and I just turned 21. Since we started dating, we’ve been fucking nonstop. Before we met, she was a very VERY horny virgin who wanted to be treated like a slut but also wanted something serious. I was all too happy to oblige. And as I’m writing this, she’s beneath the sheets sucking my dick.

So onto our first date.

She and I met outside a restaurant at a local outdoor mall. Dinner was going well and I felt things were going great. All of a sudden, she starts talking about how she gets turned on by outdoor sex and would love to fuck outdoors one day. Immediately the whole atmosphere of the date changed and I knew we were gonna mess around.

We quickly get our check, and walk out to my car. We get in the back seat and start making out while I grab her pierced nipples and suck on her neck.

I’ll let her take a break from sucking me to tell you how the rest went down:
He asked me “have you ever sucked dick before?” I answered no having had no prior sexual encounters before this. He said “do you want to try” and I was all too happy to oblige. Read more »

[MF] Department Store Dressing Room Fucking

One more story (for now) involving my cougar girlfriend “Jessica”. For those of you who don’t know, she’s 47 and I’m 21. She is a total hottie who has a 27 year old body complete with 10/10 ass and legs. Her tits are normal sized but nice. She’s Latina with perfect skin and a beautiful face especially when she smiles. About a month after we started dating, she wanted me to go shopping with her. I said to myself, “Shit. This is going to be a waste of a perfectly good Saturday.” But I was still trying to impress her so off to the fucking mall we went.

So we got there and went into one of the higher end stores. The sales lady was this old no nonsense bitch who reminded me of my third grade teacher. Jessica picked out some outfits, mini skirts, jeans, stuff like that and took them into the dressing room with her. I sat in one of those chairs they have for the guys to sit in while their SO tries on clothes for hours on end. Read more »

First night with the kinky classmate [MF]

As the end of high school approached, everyone at school had been seemingly trying to complete their high school bucket lists. I [18M] was hanging out at home when Nicky [18F] sent me a message on AIM. We hadn’t ever talked before but she was gorgeous so I was more than thrilled to have her show some interest in me. She was a tiny and tight in all the right places. He stomach was flat and toned with perky little B cups. She was Asian and had the sexiest eyes and lips.

After a quick chat she got right to the point. She wanted to hang out and was going to pick me up the next day. She showed up at my house wearing a skin tight top, skinny jeans and some cute sandals. Nothing crazy sexy, but her body looks amazing in the tight clothing. We went to see a movie. I was young and unaware of her intentions so I wasn’t expecting much. As soon as the movie started, she lifted the arm rest up. As the movie went on I felt her body slowly working its way towards me. Eventually I had my arm around her with her hand resting on my leg. The couple in the movie started kissing and without hesitating we broke the ice with a long kiss. Read more »

[MF] Getting the nerdy dancer

In my 20s, I worked full-time, went to grad school at night, and had picked up a part-time job with a local minor league team in my city.

One perk of working with the team was interacting with the dancers. They were a mix of “older” women in their mid-20s to mid-30s that had reached the term limit of the local NFL team, and then the aspiring 18-20 year olds, just out of high school.

During an official post-game after party, I flirted a bit with one of the dancers, Ali, after the other girls teased her for liking Lord of the Rings. Apparently her father had read it to her as a kid, and they saw all the movies together, and it was a big thing. I jumped into the conversation, telling her I loved LotR. The other dancers laughed at us and left.

I geeked out a bit with her, discussion the books and films, and we made plans for her to come over for dinner and start watching the trilogy.

She was supposed to show up at 8, but knocked on my door around 7. She was coming from dance team practice, and figured it would be easier to just shower and change at my place. Read more »