Category: gonewildstories

I had a threesome with one of my best friends and a guy friend – we were all in relationships at the time [FFM]

This took place two years ago. It was (and still is) my first time having a threesome, cheating and being sexual with a woman. This is also my recollection of the events that took place, from a hazy, intoxicated memory so some details may be slightly inaccurate but all in all, this is what I remember happening. *names changed for obvious reasons.

I had been having some doubts within my relationship of 5 1/2 years and was out with my friend Sarah* having some drinks. She’s around 5”8, blonde, has green eyes and a killer body. Her boobs aren’t as big as mine but still a great size, and an amazing peachy ass. The weekend before, I had shared a kiss with a mutual friend of mine and Sarah’s (Alex*) and was telling her about it out of guilt (since I was in a relationship). Alex is a medium height, around 5”11, blonde with blue eyes and a sexy husky voice. I’m shorter, about 5”3, brunette, brown eyes, slim and busty (8DD). Read more »

I met my 18-year-old high school cheerleader fuck buddy on reddit. [MF]

Rewind to last fall. One night, bored, I responded to some post on this sub by a “girl” who said she’d only recently turned 18 and she secretly loved sexting with older men. Yeah right – right? But she eventually PMed me back, and we got to chatting. “Julie” (not real) and I got to know one another. That eventually moved to whatsapp, and sooner or later, we were exchanging pictures. Only then did I start to realize that this wasn’t a catfish – she was actually real. And very pretty. At one point, I came clean and said that I’d love to keep chatting, but just to be in the clear, I needed proof she was 18. She showed me her license. So that was that. (She turned 18 last August.)

One night, some dirty chatting turns into the two of us jerking off together on a live video call. She had to be a little quiet, but not too quiet – her bedroom is in the basement of their house. It was really fucking hot – for both of us. After that, she started sending me, and requesting, nudes. Happy to comply. I’d get a quick post-shower shot in the bathroom before she left for school, stuff like that. Read more »

I invited strangers over the house I was babysitting just to [f]uck me

Thought I could share this here!
Backstory: This happened two years ago. I babysat for this couple a few times, usually when they’re working late etc. They’re pretty rich and chill, no strict schedule, it’s “make yourself comfortable.. my stuff is yours!” The kid is pretty cool too, he’s in primary. It started when they went on a romantic holiday and asked me to babysit him for the weekend. I got bored one night, kid was asleep and I was super horny so I invited a guy from Tinder I had been speaking to earlier in the day and we had sex the whole night lol.

Then few months later, the parents called me to tell me they were going on a family summer holiday for three weeks and needed me around to babysit their cat. Their cat lol!
So of course I said yes! A house to myself, swimming pool, food allowance plus paid for babysitting the cat? I was in. I was living my life for three weeks! It was early in the summer, I lounged by the pool, wore the moms tiny bikinis.. they even allowed me to raid their alcohol cabinet so I didn’t have to pay for booze. I walked around the house naked all the time (pretty sure the neighbours saw me but I didn’t mind), binged Netflix, swam naked in the pool.. Read more »

[FF]riend-sitting

Early Winter 2019.

She’s been texting with this man who broke her heart and he just plays games with her, draws her close then breaks her heart again. It’s awful to watch. But she’s a big girl making her own decisions.

Last night she was supposed to spend the night with him, but he cancelled and then texted her repeatedly about how bored he was. What a guy, eh? She texts me and asks if I could come over and distract her so she doesn’t text him all night. Friend-sit, she called it.

So, me and my drugs and a board game walk over to her place around 7:30pm.

I let myself in.

The room is dimly lit. A bed up is made in the middle of the sitting room. My glasses are fogged. I can’t see properly but I can tell she looks hot, and tell her so. She’s wearing a black silk nightie and black high heels. Light make-up, hair done up. So alluring. She’s half into a giant bottle of wine…I’m wary of her vulnerability and a little concerned about alcohol and consent. So, I sit. We share some weed-infused maple hot chocolate and a joint. She tells me about the playlist of break-up songs that’s playing. We talk. We play Love Letter. I make her practically crawl into my lap when she gets to see my cards, and she loves it. Her hand slips into mine, or down my thigh. Her eye are smoldering. Read more »

[MF] She showed up at my summer job…

There I was, years ago, home from sophomore or junior year of college for the summer, working for a few months at my old high school job at a retail / convenience store. School was about three hours from home. The girl I was seeing, off and on, lived closer to my home than she did to our college, but still about an hour away. And we weren’t in regular daily contact over the summer.

Ok. There I am, stocking shelves in an extremely attractive retail style vest, probably counting the minutes until I could go home. Suddenly I hear footsteps coming down the aisle, I look up and… it’s her. I had no idea she was in town, but she knew where I worked and this wasn’t an accident.

How did I know it wasn’t an accident? Well, she wasn’t in the kind of makeup and clothes she liked to wear out at a bar, but it was also not what you’d put on just for a trip to pick up cotton balls and razors, if you’re following me. Makeup and a nice tan and this tight brown top with a deep v with a ruffle… Read more »

Taking Care Of [M]y New [F]riend

Owing to the current situation we’re all in, the inability to write new stories has me thinking of some of my past stories. This story, took place last year when I was meeting my friend Liz at our college’s library. Liz was in her junior year of college whereas I had already graduated a few years prior. When I came to meet her, she was with her friend Alyson whom I’ve never met before

To better paint the picture, Liz is Peruvian, olive skin, about 5’3, slim with one of the best assess I’ve seen. She knew it as well, as I swear, I’ve never seen her in anything else but black yoga pants and some tank top. On the other hand, Alyson was about the same height as Liz, thinner, petite, white skin, a really cute face with some of the most kissable lips, and was Hmong (yeah, me too, I had to google that when she told me that). Alyson also did some modeling (nothing serious) and had a great sense of style. I myself am about 5’11, 160 pounds, fairly fit, brown skin, glasses, with a light trimmed beard Read more »

Married trophy wife initiates affair [MF] for the first time with artist mentor.

I’m an artist. I mostly make oil paintings. I teach one-on-one lessons on the side both to give back to the art community and to make some extra money. About a year or so ago I met a guy named Rob at one of my openings. Rob is in the movie industry and turned out to be an enthusiastic patron of the arts. He eventually ended up owning three of my paintings and hired me to give his wife private painting lessons. Yesterday something unbelievable happened and I had to write it out.

The sessions took place at Rob’s residence in the guest house by the pool. The place was very nice. Beverly Hills, North Rexford Drive, gorgeous neighborhood, and his wife matched the setting. Jen was a surprise to me – her husband, although nice, seemed habitually disheveled and lacking in style. Where Rob was dumpy and inept, Jen seemed sophisticated, active, and hip. She was a stay-at-home wife who spent most of her time reading and working out. Recently, she had developed a keen interest in the fine arts and was excited and enthusiastic about learning how to paint. Our first few sessions were purely professional. We went over materials, basic technics, and a little art history. We definitely had chemistry and we were laughing quite a bit. There were a few moments where we locked eyes a little longer than we should have and I think we both knew it. Read more »

[M]y first time encountering large labia (long)

Dirty bits after the ~~~~

When I was 19, I worked at a diner style restaurant as a busser. The wait staff split tips with us, so the money was decent, and everyone, front and back of house, hung out in our off hours. All of the typical restaurant worker shenanigans were in place: broken Spanish? Yep. Drugs and alcohol? Uh huh. Waiters swearing at the cooks and cooks treating waiters like dickheads? Peppering most sentences with four letter words? Fuck yeah. A little grabass here and there? You know it.

Like Bourdain says, it’s like working on a pirate ship. Good fun for those with a strong stomach and an appetite for mischief.

One of the young women working there, Genevieve, was pretty–curly brown hair, big brown eyes, generous lips, big white teeth, and smart in a very odd way. Around my age. She could recite every one of the Constitutional Amendments word for word, but she usually didn’t get jokes. At parties, she went hard, but she was always pretty quiet. She just didn’t know human nature very well, I guess. Read more »

Quarantine Roommate – Part 2 [MM]

This is part 2 of the story. Part 1 is [here](https://www.reddit.com/r/gonewildstories/comments/gj1bc9/quarantine_roommate_mm/).

My first night sleeping with Manu was really good, I slept like a baby (probably because I was tired after our very intense fuck session). The next day was a Saturday so I didn’t bother setting up the alarm clock. I woke up late in the morning and Manu was still asleep. He was laying on his back but slightly turned to my side. Now with the morning light coming through the window I could properly see him. He had a hand behind his head allowing me to see his armpit, it was such a sexy pose to a sleeping man, like he was unconsciously sensual all the time. The few hairs in his chest would kinda glow in the morning light, same as the delicious trail of hair that connected his belly button to his pubes. His heavy cock was laying on his thigh, it was totally soft yet so big and thick and manly. It shouldn’t be allowed for a man to be so good looking and so well endowed, what’s left for the rest of us, average-sized average-looking people? Read more »

Quarantine Roommate [MM]

[English is not my native language so please forgive me if I make mistakes. I’m open to feedbacks on that too]

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This started a few weeks ago.

Due to the covid-19 epidemic, some companies started asking people to work from home, which was my case.

Amid the first week working from home I was texting a friend (let’s call him Manu) that, like me, was also social distancing alone, talking about how work and life were in this period. He told me that the thing he missed the most about his job was the air conditioning. I live in South America so mid March is still the end of summer and we have some very warm days. He doesn’t have air conditioning in his apartment so he was struggling with that.

“If I weren’t joining conferences every day, I would be working naked” he said.

“Well, why don’t you? People might enjoy the view. My colleagues have to settle for my bed hair and 5-day beard” I joked. Read more »