Category: gonewildstories

Boxing [MF] Long

I recently picked up boxing lessons as a Christmas gift from my a friend. They knew I had wanted to try it out for quite some time. I was already to go for my first lesson. I had made a session online with Vic who is the head trainer of them gym.

I arrive for my first session and I said to the receptionist that I had a session with Vic. She then gets up from behind her desk and brings me to Vic’s office. I was then taken a step back because it was a beautiful woman. Vic apparently stood for Victoria. She was about 5’7”, slender and athletic. She had breasts that were on the smaller side but her ass was amazing.

We introduced ourselves. She asked me to take off my shirt and shorts and step on the scale. Now I’m a bit of a shower and I had compression shorts on (soft about 4.5 inches and hard I’m just under 8) When I took my shorts off a noticeable cock outline was on my underwear. Read more »

The time when I [M]et someone [F] by answering a craigslist ad.

I used to browse through craigslist personals section, mostly for entertainment. Most of the ads seem fake, but every once in a while you find a real person with real needs and somehow, you end up at their place in the middle of the night. This is one of those stories.

It was nearly 11pm when I saw her ad. I don’t have the original one anymore, but I do have our emails before we switched to text. From what I remembered, she was wrote an articulate ad stating that she was a normal and regular person who were sexually openminded and enjoyed sex with strangers. This was definitely not her first time, and probably won’t be her last, meeting strangers for sex.

I wrote to her, fully expecting to be ignored. My subject line even referenced her inbox blowing up. But to my surprise, within 10 minutes, she replied. I told her that I was, like her, a functioning member of society with a wild side, and attached a semi-naked photo of my back (I think I have a nice muscular back and butt). She replied saying *”Hey. Nice to meet you! Yes, I am a regular person with a job but also a pervert”* and attached a couple of face pics. Read more »

[MF] The Seedy World of Peep Shows, and Me

Months after my [first strip club experience](https://www.reddit.com/r/gonewildstories/comments/9zd55d/mfstripclubvirgin_an_ode_to_the_first_lapdance/), I was happy, horny, and full of no saving grace. The experience was visceral and the feeling of contact between another human being was something I longed to experience. Those were the first boobs in my post-pubescence to frame my vision, but they would not be the last, and I needed to see something beyond.

The thrill and excitement to explore the seedy side of history and human sexuality took hold of me. Curiosity grabbed my hand, and led me to a past of flappers, floozies, and the tease of breaking prude laws of an Al Capone era style, prohibition tale. I came across in my studies of something naughty, the era of the peepshow. It was a remnant of a darker time in history, where streetwalkers roamed the streets, hustlers and pimps paraded up and down a neon 42nd Street getting their scores. In billboards gone, the words “live nude girls” and “xxx” and “adult theatre” in pulsing neon tubes would flash back and forth, with a the shape of a tantalizing woman, who would kick her legs up and bring them down again. Read more »

I [M] caught my G[F] getting fucked on the couch

Bit of background, been with my GF since we were both 17 so hadn’t been with anyone else apart from each other before. But 5 years into the relationship and I started getting attention from another girl and eventually got a few hand jobs and blowjobs before fucking her fully.

Cheating on my girl then happened on the regular for about 9 months before I started to float the idea that we bring a third person into the bedroom with my girl and me. Even suggesting we get her another cock to play with or I watch her getting fucked. She even agreed to a threesome with another girl but it didn’t come to anything.

So fast forward a year or so later, I’ve stopped fucking this other girl. My gf is on a night out on the town with a few of her extended family, while I’m at home. Her cousin brings his wife along to it who also gets her brother to come drink with them to. This guy is a good bit older than us, like early 40s, keeps in pretty good shape, very confident, can tell he just fucks women regularly and just leaves them when he’s had enough. Seemingly they hit it off really well and she starts to get more secretive and distant, not answering calls or texts as quickly when we’re not together, not being as available as much as she once was. Read more »

The trashiest sex I’ve ever had… pun intended lol [m] [f]

So back in high school I use to work at the local McDonald’s… my family was a little poor so I had to work all the hours I could to pay for my car and cellphone so I closed down the restaurant most nights… there’s always three closers a front cashier and two grill workers and at the time I was one of the grill workers… the other was brian, a new guy who came from a rich family who was cocky and full of himself and basically everything I wasn’t… don’t get me wrong I had friends and wasn’t shy and lost my v card already but that was the only time I had had the sex and that had been months before… the closer up front was Jen and my god she had the biggest set of tits on her!! A little chubby but held it well… she was in her 30’s at the time and had two kids and husband at home… Read more »

I helped take her cherry, and I’ve never [M]et her.

This is an absolutely true story.

Wayyyyy back in my AOL days (1990s), I met an 18-year-old virgin online. She was a college freshman who was curious about sex but had virtually no experience. I kept trying to push the conversation in a more sexual direction, but she had (frustrating) limits.

She asked a lot of questions about sex and was quite curious. I kept hoping to ramp it up, but it wasn’t happening.

We’d drift in and out of email contact. Neither of us was into cybersex, and she wouldn’t do phone. She wouldn’t give me her mailing address. I sometimes wondered whether she was real (spoiler: she is).

Eventually it emerged that she wanted a vibrator, but she was afraid to buy one. She wouldn’t go to a store, and she didn’t want a mysterious package showing up at the small college she attended.

The U.S. Post Office has an obscure and ancient service called General Delivery. This is an old-fashioned service where you go to the PO counter and ask whether they have mail for you. It’s addressed like this:

>John Doe
>
>General Delivery
>
>City, State Zip Read more »

Girlfriend got a little too drunk for her own good [MF]

I feel a bit guilty about this. For reasons not entirely clear to me, I really enjoy sex with my girlfriend when she’s very intoxicated. Watching her lose her sobriety and turn into a stuttering, slurring, sloppy mess really turns me on.

The other night, she went out for a girls night out, and I needed to stay home to take care of some work. After she pregamed a with little wine, I gave her some cash for drinks in the hope that she would have one too many, and she didn’t disappoint. As she hopped from bar-to-bar, her texts became more and more illegible and her face more flushed in her pics that she kept texting.

Before bar close, she snapped me a pic of her and her friends taking shots with the caption “lp lov you babe.” So I knew she was lit up like a Christmas tree.

About an hour later, she staggered through the door, hiccuping and laughing, and begging for sex. Swaying from side to side, she tried her best to hide her extremely obvious inebriation, which was cute, but her kisses cast a strong aroma of tequila and her glassy eyes could barely stay focused as she fumbled messily for my swelling shaft. Read more »

[MF] My first time being cucked (Part 1 of 5)

Also posted at [r/cuckoldstories](https://www.reddit.com/r/cuckoldstories/), but I figured it might be enjoyed here too.

This story is mostly true. It is a composite of a three separate of events, but makes for a better story when told together. There are also some embellishments and names are changed, but is honest otherwise. This first post is mostly setup, but it’s non-stop after that. Enjoy!

​

Steph and I had been dating for just over two years. Steph is a stunning, 22-year-old 5’4″ brunette with a great body. She’s curvy and looks stunning with E cup tits that are great for her body.

We met in college and hit it off straight away, and the two years of our relationship up to now have been good, despite the odd argument. Everything was going fine up until a few months ago. Recently we’d both been stressed with work and grad school, and our sex life had been struggling as we were less focused on each other. Having opposite work schedules where I work nights and she works days, with only one night a week together, made it worse. This, teamed with the excitement that comes with a new relationship wearing off, resulted in us only having sex about once a week instead of once a day like we used to. I think that part of the problem we were having was that Steph wanted me to take charge and take the initiative, which I struggled with. Read more »

Hooking up with [F] coworkers at [M]y last job

Shortly after moving to Miami, my wife and I separated for a short time. I was suddenly single in a very horny town and went nuts… banging every chick I could. There was a Russian chef with big perfect tits, a Jamaican mom from Tinder who was incredible in bed, a horny married Latina in her 40s (I still jack off to the video of her sucking my cock in her SUV after we smoked a bowl) and a few strippers.

A few months into this wild period, a coworker randomly told me to stay away from the hot, half-Korean half-white girl who was our GM’s assistant. She worked one floor up from me and would ALWAYS wear really tall high heels and tight outfits. She seemed really well put together as she’d strut around the building. So of course this opening was all I needed. I happened to be looking for a new weed guy at the time… and a new connection happened to be around the corner from her place. She didn’t smoke, but I mentioned the weed guy to her and she suggested I stop by the next time I was in the neighborhood. The next Saturday, I came over and we opened some wine. Her neighbors came over and I was cool with it. I worked with him too and he brought his awesome weed. We sat in her backyard and I happily smoked and drank and could not keep my eyes off her sexy ass lips… and her killer legs. They were long, tan and toned from years of wearing high heels. After hours of hanging out, the neighbors left and I asked if I could crash there because I was trashed. She smiled and said yes. When we went inside and closed the door, I said, “Would you like to makeout before we go to bed?” Read more »

[F]un with [F]riends on weekend visits ho[M]e. (Full story)

I (then 18/M) started dating K (18/F)
towards the end of my senior year of high school. We knew the “long distance” of me going away to college (about 1.5 hours drive) in the fall & her staying back home was going to be hard, but we knew we could make it work.

One weekend around midterms that spring, I was unable to make my weekend trip home because of being swamped with assignments and needing to study. K asked me if we were okay and if the reason for me not coming home was truly being overloaded with work. Once I assured her we were great and that it was just the work holding be back that weekend, she let the flood gates open on a little secret of hers.

Her big secret was that she had been developing a sort of crush on two of her two female friends and that she thinks she is Bi. K had been hanging out with A (18/F) & P (18/f) more while I was away at school. The crush got a little stronger after the three started trading bedroom stories. K asked me what I thought about her secret and if she could approach A or P with her secret. Depending on how they reacted, her plan was ask them to play with us. Read more »