Tag: Group

My [F] first time fucking for money.

For my second story, I want to talk about my first fuck as an escort. We’ll call my first customer M.

I met M while I was working at a strip club that he and his friends came to almost every weekend. Initially, another guy in the group bought up nearly all of my time, but M would buy a dance here and there when he saw an opening, and we got along really well. I’d been toying with the idea of becoming an escort, and for reasons I still don’t entirely understand, I told him about it. We circled around the issue very carefully, but to make (this part of) a long story short, he made it clear that he would be interested in being my first customer.

We decided I’d meet him at his place on a weekday in the middle of the day. I was 50% excited, and 50% nervous. It was a little awkward at first, but then it occurred to me to turn on the stripper charm around the same time it occurred to him to suggest we smoke some weed, so it didn’t stay awkward for long. Read more »

How I seduced my friend [MF]

Story from a few years ago… “K” and I had been friends for several years, along with a larger group of guys and girls. She had kind of a motherly role among the guy friends, always looking out for us and organizing activities and things like that. I always knew she had a special liking for me but never wanted to act on it.

Don’t get me wrong, I would gladly have fucked her. She was half white, half Asian, about 5’5, average face, average tits, but ass hips and thighs to die for. Former volleyball player. But I didn’t want to deal with her getting attached as I didn’t like her like that and was always getting it from plenty of other girls anyway.

One day though, horniness took over and I finally gave her what she’d been wanting.

My roommate and I had had people over a few weeks ago and K had left a jacket at our place. In the meantime I had sprained my ankle pretty bad playing basketball so was working from home for a few weeks. One day K texted us and said she’d be in the neighborhood tomorrow and could she grab her jacket. I said yeah I was working from home and she could come by any time. When she heard about my injury she said she’d bring some leftover soup too. Nice girl. Read more »

[MF] My [F20] boyfriend [M20] and I secretly fucked while our friends were sleeping

this was a few years ago but I still think about it every now and again. I put a little bit (a lot) of what I think is important as background knowledge but I’ll put a —————— when the interesting stuff starts.

my boyfriend and I had the same friend group in college and we had been together since our first year. Throughout our relationship, we had A LOT of sex, I think we averaged out maybe 3-4 times a day. We both had high sex drives and explored our kinks with each other as we got comfortable in the relationship. One of our favorites was definitely public play / exhibitionism. He’s always been the one to initiate anything we did publicly or just in front of our friends like slipping his hands between my legs during a movie or having me suck him off at a park in broad daylight.

We all wanted to do something fun for spring break and planned a road weekend trip to Joshua tree national park. We got a big group together and booked a cute little Airbnb house. Read more »

Scandalous in Belgravia – How a short trip for a stag party ended up with me spending a night with the bride-to-be and taking a walk of shame through a very nice part of London [MF]

*This story features my friend Liz,* [*check here for the history*](https://www.reddit.com/r/gonewildstories/comments/l5r8g3/the_very_best_of_british_hospitality_mf/)*. Sexy stuff below the line.*

After my first hookup with Liz, we continued to see each other every once in the while, either she would come to Zurich, or I would go to London, we would do some sightseeing, and mostly fuck a lot. A few months after our first hookup, she had started seeing another one of her local hookups more regularly, and it evolved into a serious relationship. I got to meet her boyfriend Chris when he came with her to meet me at the airport before one of our weekend romps I had tied to a business trip. Although Chris and I didn’t have the sort of chemistry that would lend itself to a threesome, we also got on great, and soon the visits changed from me seeing Liz for sex, to her and Chris hanging out with me and Anne. We worked great as couple friends, but there wasn’t the chemistry for any sort of group sex or swapping, so Liz and I had an unspoken agreement to set our sexual relationship aside and just enjoy a good friendship. It was a little bit of a strange way to make friends, I suppose, but we did enjoy hanging out together, and, once Liz and Chris got engaged, we were delighted to come to their wedding. Read more »

I [M] was the first dick she [F] needed after getting vaccinated.

With all the pent up sexual energy out there because of people quarantining and distancing, I’m sure I’m not the only one that has had old hookups or FWB from the past pop back up. Over the last year I’ve had maybe 5 or 6 people reach out randomly from the past to say hi. I have enjoyed getting to catch up with everyone, but they have also all inevitably turned to flirting, and nudes, which I have also enjoyed.

One girl (let’s call her Stella) was a FWB I had maybe 5 years ago now. We had been friends and hung out for a year or so, and in that time hooked up maybe a dozen times. Usually more low key, after getting drunk with friends, that kind of thing. She had always been really fun to have sex with – very passionate and engaged, loved to have longer sessions, which is my preference too, and easily came multiple times, which I absolutely love. I had always felt a bit weird pushing for more with her though, cause I knew she was in an on-again, off-again relationship with this other guy, and didn’t want to be in the middle of something. Read more »

Squadron Moral (hot wife/swinger/gangbang/work/military)

The prepared sandwich platter from the NEX made sandwich selections easy, the round pink nipples, pert breasts with the slightest sag of motherhood, made focusing a little more difficult. The men are at the communal table and she ate in the kitchenette picking at her food eating chips and watching them eat the tv playing music. Diaz, Neary, Hunt, Darocha, and Davis talked animatedly with each other, Harris looked slightly uncomfortable, almost angry.

“Alright men I need to take a shower, and if your expecting me to suck, fuck or otherwise entertain you and your meat you need to shower as well.” She tossed a few boxes condoms on the table. “Harris why do you look angry.” He looked at the guys expecting them to bitch at him for his answer. He took a deep breath.

“I don’t think Chief should make you do this, he is practically pimping you out.” Anne smiled inwardly, but kept a stern face. Trying to be commanding while topless took some effort. “Harris, I know this may come as a shock to you, but Chief didn’t order me to do this, he asked if I wanted to.” Neary put up a hand, “yes?” Anne said with a quizzical look. “ AD1 you not like getting back at a cheating husband or something? Or I dunno midlife crisis or some shit?” Read more »

[MFF] Girlfriend shows her naughty side

“Yes dear, I’d love that” – the words echoed in Joel’s mind all day.

Alice, his loving partner, whom he’d always shown the fullest respect and love, was showing her secret naughty side.

“I’ve always wanted to see how you’d treat another woman, now I can see it while joining in too,” she reasoned with him, perhaps reasoning more with herself, “and make sure I’m not missing out on something.”

He had no problem finding a third person, their long list of friends including several people extremely open when it came to sex and experimentation. Emily was her name, a thin, tall brunette, roughly similar to Alice’s body type but with a much different face and demeanor. She’d been a friend of the couple since their college days, where she was well known among the group for her openness and wildness, the former staying the same as the years went by, and the latter becoming less prevalent.

“What do you want me to do? Is there anything I should expect? You’ve done this before, right?” Joel asked Emily nervously, even though the questions (and his own ideas of the answers) had been running through his mind since Alice agreed to do it. Read more »

Alone with my best friends mom

My best friend Samuel and I have been friends sense 4th grade and even are in the same college together, we also share a dorm room. For some people this might sound like a bad idea but for me, it was perfect. We always got along and knew each others boundaries. Samuels mom has always been there for me but I never thought of her as more than just my friends mom. Once I got to my senior year of high school I did start to notice her more for her body though. For a woman in her mid 40’s she looked good. She had Samuel a bit young so she was one of the younger parents in our friend group. She was short, about 5’5 with beautiful full lips, long Lucious brown hair and a chest that would satisfy any man. She had a slim waist and an ass that I dreamed about bouncing on my cock, but after we went off to college I never saw her until she came to visit Read more »

[M]y wi[f]e’s [f]irst threesome

“I don’t think I’m going to eat her pussy,” Anna said.

I chuckled.

“Sure thing, babe,” I said. “Whatever you feel comfortable with, it’s totally fine.”

And I meant it. It was, after all, going to be her first threesome, and I knew she was taking a big step by even trying. We’d had quite a few talks over the previous weeks, after she felt that she was ready for me to start looking for a woman to join us.

I’d had a decent amount of experience with non-monogamy and group activities in my 20s: a couple dozen threesomes between my ex-girlfriend (the subject of one of my earlier stories) and some fun friends with benefits. But Anna had been unlucky to have a series of vanilla boyfriends in her 20s; we met early in our 30s, and she was ready to try new things. I’d told her about wanting to have some level of non-monogamy during our first couple dates, and she’d said she’d always wanted to have a threesome, just never had a willing partner or a way to even find a ‘unicorn.’ Anna doesn’t identify as bi, but she’s always admired the female form and had always wanted to see what it would be like being with another woman. Read more »

Beginning of College Experimenting [Group]

This is my first time sharing a story. Thought I’d give back after all the great ones I read here. This comes from my freshman year at college. This was the beginning of a few more similar incidents.

I had been dating a girl named Haley for a few weeks. She was blonde, half Hispanic, short at about 5,2, fit, but not skinny, with normal small boobs with huge nipples and a huge bubble ass. I was already fucking her at this point so I knew she had a fully shaved pussy. She had big DSLs. Haley’s best friend was Katie, a tall, skinny brunette with no tits and no ass and I learned later little sexual experience. Haley came from a blue collar family, like me. Katie was a prim boarding school product. My friend Matt, also a boarding school graduate, had a nonsexual (as far as I knew) flirty relationship with Katie, where each liked to provoke and needle the other with nothing actually happening. Matt was dark haired and athletic—he was a swimmer or played water polo or something. The four of us plus one or two other friends did everything— ate all meals and hung out at night—together. Read more »