I fucked my girlfriend and her fiancee. [FM] [FFM]

Note: it’s been a minute since I posted a story. Life gets in the way.

Background:

– [The first night I watched Rachel and her girlfriend have sex](https://www.reddit.com/r/gonewildstories/comments/ia7bpu/i_m_got_to_watch_a_longterm_flirt_have_passionate/)

– [Rachel’s night with four public orgasms](https://www.reddit.com/r/gonewildstories/comments/idwvnj/a_night_to_remember_count_it_up_her_four_orgasms/)

– [Late-night hotel room sex with Rachel in front of her girlfriend](https://www.reddit.com/r/gonewildstories/comments/iu384m/we_fm_had_latenight_hotel_room_sex_in_front_of/)

New Years Eve is always one of the biggest party nights of the year (you don’t need me to tell you that, I’m sure), and I was going to be DJing a huge private ticketed party. Catering, fire dancers, a band, the whole deal. All I had to do was play from 12-2, and I’d be done. Band played until midnight, they did the countdown, then I dropped Auld Lang Syne, and off we went.

My very sick buddy needed to relieve some tension. I’m just an idea man, folks. [FM]

Note: this story isn’t about me, but I’m directly involved in it, if that makes sense. It’s a sad story, but its also a happy one. You’ll see. I realize in advance that this isn’t a typical /r/gonewildstories post, but it’s one that’s pretty rad in its own way.

Also: trigger warning for cancer, death. I mean, sp*iler alert, but also…yeah.

——

In 2015 when [I was the touring DJ for a frat rapper](https://www.reddit.com/r/gonewildstories/comments/i4jdcc/i_got_a_blowjob_from_a_bottle_service_girl_in_the/), it was one of the best times of my life. I got to travel the country and get paid pretty darn well. I was away at one point for two months, and I was texting my buddies from high school and uni pics of the #tourlife.

My best friend (we called each other our hetero-lifemate), Tommy, was as happy as could be for me. I met Riff Raff at one point and I got him to send Tommy a video message (dude was a big fan, in an ironic way). It was fun. After the tour ended, I went back to Manhattan, and Tommy called me. He told me he had stage 4 lung cancer, and he probably had six months to live. This was, needless to say, shocking to hear. He smoked probably 150 butts in his life — turns out he had a bunch of super-rare genetic markers for his ancestry that put that shit in his lungs.

We [FM] had late-night hotel room sex in front of her girlfriend. [FM] [FF]

Some context:

[https://www.reddit.com/r/gonewildstories/comments/ia7bpu/i_m_got_to_watch_a_longterm_flirt_have_passionate/](https://www.reddit.com/r/gonewildstories/comments/ia7bpu/i_m_got_to_watch_a_longterm_flirt_have_passionate/)

[https://www.reddit.com/r/gonewildstories/comments/idwvnj/a_night_to_remember_count_it_up_her_four_orgasms/](https://www.reddit.com/r/gonewildstories/comments/idwvnj/a_night_to_remember_count_it_up_her_four_orgasms/)

——

Rachel and I had been “dating” for about two months. I say “dating”, because if you’ve read my [previous stories about her, you’d know she was in an open relationship with a lovely woman, Gabi](https://www.reddit.com/r/gonewildstories/comments/ia7bpu/i_m_got_to_watch_a_longterm_flirt_have_passionate/). But we *were* dating. I’d even go so far as to call her my girlfriend, and things were really good. She’d stay over at my place sometimes (she lived in Brooklyn but worked in Manhattan, so her commute time was drastically reduced on those nights). Still, most nights she’d be at home with Gabi (or Gabi would stay somewhere else, and I’d stay at their place). It wasn’t “normal” per se but it was a pretty reasonable setup, all things considered.

So, two months of hooking up and I figured “who better to bring to my high school buddy’s (Richie) wedding than Rachel?” Even though we’d only been dating for a relatively short time, I asked her if she wanted to come as my date, and she gladly accepted. I did have to call Richie up and beg him to let me bring a +1 after I told him I was riding solo originally, and he had to ask his fiancee to go with it. They thankfully accommodated us, even though it was two weeks away (in fairness, I confirmed with Richie before I asked Rachel).

She told me to fuck her in her Halloween makeup and costume — after finding out why, I couldn’t say no. [FM]

Prior adventures that are somewhat related:

I [M] got to watch a long-term flirt have passionate sex after not seeing her for a few years. [FF] [FM] from gonewildstories

I [25/M] fucked the hot bartender [27/F] after she demanded it (not that I was complaining) [FM] (long-ish) from gonewildstories

I got a blowjob from a bottle service girl in the back room of a nightclub. [FM] from gonewildstories

(skip to &&&& for the naughty stuff)

I’ll set the scene: I was DJing a bottle service nightclub on a Friday of Halloween Weekend in 2014, and it’s a wild night. Sparklers, glowing bottles, CO2 cannons, it’s great. The club was packed with bachelor and bachelorette parties, there was a dozen and a half other tables going crazy — and with it being Halloween Weekend, it was even more debaucherous than usual. Holidays always bring out the nutters (St Pats, Halloween, NYE, Thanksgiving Eve are the terrible foursome).

A night to remember, count it up: her four orgasms in four locations in one night [FM] (part 2?)

(Part one [here](https://old.reddit.com/r/gonewildstories/comments/ia7bpu/i_m_got_to_watch_a_longterm_flirt_have_passionate/)!)

Sunday morning (eh, around noon, I didn’t get home from work until 5a or so), I texted Rachel to see what she wanted to do. She responded pretty quickly, saying we should just grab some food and drinks to go and hang in Prospect Park. All fine by me. Then she sent a picture of her and Gabi in bed together in a state of undress, cuddling. I asked her if Gabi was coming as well — I was happy if she came along, she was really cool — Rachel told me no, she had plans tonight with a friend of hers, but maybe we’d meet up later at night. We spent the day texting, with her sending me pictures of her in the shower, on her bed, and me telling her what I wanted to do to her looking like that. Later on, about an hour before we were supposed to meet up, she sent me a 30 second video of her and Gabi making out, which sent me over the edge a bit. Just… damn.

I [M] got to watch a long-term flirt have passionate sex after not seeing her for a few years. [FF] [FM]

DJing in New York City is simultaneously a very humbling experience and also extremely rewarding. For years, once a month, I DJ’d at this dive bar in Brooklyn that was notorious for a few things: drug use in the photobooth (and the evidence being stuck in the wall next to it, [like this](https://imgur.com/a/ZuQlprG) — I took a photo of this after the last gig I played there before COVID), some nasty bathrooms, and a dancefloor where a DJ could play almost anything and everyone went there looking to dance and/or fuck (okay that’s all fairly normal for most bars, but whatever).

It was hipster-extreme, and it was my refuge from the cookie-cutter bottle service clubs in Manhattan where it was the same 200 songs every night, give or take 30. At this place in the same party, well after midnight, I could play Paul Simon, A$AP Rocky, Taylor Swift, M83, old Britney songs, Franz Ferdinand, Migos, Ini Kamoze, Prince, the theme from The OC, and people would belt out every word for hours straight. It’s the best crowd in the whole five boroughs in my opinion — Black, White, Latino, Asian, gay, straight, trans, hipster, bros in frayed lacrosse hats, girls from Long Island in short dresses and heels “slumming it” for a night — the crowd just rocks and it’s a gig I miss terribly since COVID.

I [25/M] fucked the hot bartender [27/F] after she demanded it (not that I was complaining) [FM] (long-ish)

skip to the filthy stuff by searching for &&&& (sorry, I really enjoy writing the background stuff, but if you’re just horny go for it)

A few weeks after I got back from [my last trip to London](https://www.reddit.com/r/gonewildstories/comments/hyltsz/i_24m_fucked_my_longtime_crush_after_she_23f/), I started bartending and DJing full time and decided that PA wasn’t enough fun for me so I decided to move to NYC into a shitty apartment I found on Craigslist. I had 2 roommates in a 5th story walkup in Manhattan, and it was the most exciting thing ever for me. Basically broke and surviving off of money I had saved up from the 6 months I lived at home, I got deep into the Manhattan bar and club scene, trying everything possible to “make it” as a DJ. It was scary and very hard at times thanks to NYC having the most competitive DJ market in the country (sorry LA). Thankfully, I wasn’t a newbie like many other DJs so after proving myself and making the right connections, I started enough working gigs that paid well enough to avoid thinking about a 9-5 and meant I just got to fuck around, gig, and have fun — I was working 4 or 5 nights a week. One of those gigs was a Friday night residency at this club where that was “hip” enough to get me some cred in the city.

I got a blowjob from a bottle service girl in the back room of a nightclub. [FM]

I started DJing in high school and did it through Uni (as a way to make extra money under the table) and after coming back to the States I mostly bartended and DJ’d to make money until I could find a more stable 9-5. That never really happened for more than a short stretch, so I’ve worked as a tour and nightclub DJ now for a while (well, not for the last five months) and I’ve been fortunate enough to travel all over for the job. For a while, I worked with a rapper for a while who was moderately popular for some time (if you were in college in 2015, you definitely got drunk to his music). About five years ago, we toured the US and at one point played two shows in three nights in Arizona, with a night off in between where I secured a gig playing a bottle service club. When I showed up on Saturday (early as always), I introduced myself to the managers, security, bartenders, barbacks, and bottle girls just to be friendly, exchanging IG and Snap info with some of them, standard stuff to do so you can tag them in your posts. They had flier’d for the night touting me as the rapper’s DJ, so they had an opening DJ as well, who was cool. I got to talking to a few of the bottle service girls before we opened and snapped some pics for social media. One of them in particular, Amanda, was interested in the rapper and wanted to know all about him. She asked if I could put her and some friends on my guest list for the show the next night, and I told her sure. She was not really my type but was definitely attractive — platinum bleach blonde, ditzy, fake tits, nails, and lips, about 5’1″, and tons of makeup. She has something like 72k followers on IG for a reason, and it’s not because she gives great life advice (admittedly, I still follow her there).

I [22/M] finally fucked my FWB [20/F] after a month of “just” fooling around. [FM]

Context and background

[I fucked my longtime crush (a friend of her friend) after she teased me from 3,500 miles away](https://reddit.com/r/gonewildstories/comments/hyltsz/i_24m_fucked_my_longtime_crush_after_she_23f/)

[The first time I made her squirt](https://reddit.com/r/gonewildstories/comments/i1arag/the_first_time_i_22m_made_my_ex_squirt_20f_and/)

[Prelude to this story about the days she was gone](https://www.reddit.com/user/notsafe4workthrow/comments/i3ddyc/more_context_as_to_what_happened_before_my_fwb/)

It was now Saturday, and I was out again with some of my friends at a pub, and I hadn’t heard from Lisa (my FWB) since earlier that day, and she was supposed to get back the next morning. Just before midnight, she texted me a picture of herself in a mirror, naked — but I recognized it as her bedroom in London, not home in Doolin. I pulled my phone close to me so it was more private and eagerly began texting her back.

> **wait are you back??? i thought you weren’t due until tomorrow?**
>
> *i wanted to surprise you with an earlier flight. are you surprised enough? :>*
>
> **i am extremely surprised and happy about this**
>
> *come here, ditch your mates right now, i need you*

I (24M) fucked my long-time crush after she (23F) teased me from 3,500 miles away. [FM]

([Originally posted](https://www.reddit.com/r/gonewildstories/comments/hyltsz/i_24m_fucked_my_longtime_crush_after_she_23f/) this on /r/gwstories last week but didn’t realize how many similar subs there were… sharing it here now!)

(Sorry the intro is long, but I’m a storyteller first and a pervert second. Also, I’m an American who lived in London for five years, so I mix my American and British slang and terminology. If you’re British don’t get mad at me for saying ‘mates’ or ‘Uni’ when I only use that to refer to my time in London but still use American slang elsewhere. I get enough grief from my family about this in the other direction “ohhhh, you went to ‘uni’ with your ‘mates’.” Good grief.)

I’m an American who went to do his Uni undergrad in London (this story is almost a decade old). It was the best decision I ever made — spent five years there, and I loved every minute of it (I took a victory lap year because…why not? I got my visa extended.). I was dating this one girl at the end of my fourth year who I thought was “the one”. Lisa was Irish, brilliant, red-headed, chaotic, beautiful, a little troubled, and extremely outgoing and adventurous (both in and outside the bedroom, though this story isn’t about her, I have fifty public sex stories about us, and holy shit was she a squirter). (Sue me, I like using parentheses.)