POST 1 OF 2
Posting this from my porn account since I have no one to share it with in real life. It’s really like three stories over the course of a week but I’ll try to sum them up. By far the most surprising thing that’s happened to me in my ten-ish years of sex. I’m also gonna post it in two parts because it’s fairly long.
Fair warning, this is maybe 40% sex and 60% general anecdote. The details for me are all tied together. Also, CONTENT WARNING: Sex work, group sex, drugs, alcohol, show business, other fun things like that.
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I’ve got a really close friend from college named Melissa. I’m 25 now, and she’s a year older than me, so 26. When I met her we were both in film school, and she was a rich girl from LA with big dreams. She’s Coptic Christian, Iraqi. Her parents are brokers for corporate art installations. They’re pretty conservative, but right at the time we met she was first starting to discover her lesbian sexuality. I remember her gushing about cute classmates, or saving pictures of big titted celebrities on her phone.
Fast forward to 2021. She and I are both working in the art scene in various capacities. I’ve had a few relationships, the most recent one lasting two years until it ended in November. She’s also dated women, but never for that long. She only just recently came out to her mom.
Somehow, she has this incredible ability to bag girls way hotter than herself. She’s got a cute face, don’t get me wrong, and a nice body with a skinny waist and a thick, solid ass. Mostly, though, I think it’s her confidence, and her pretty chic androgynous style. She’s told me a lot about her sex life over the years, confiding in me as a level head and a trustworthy straight guy friend. She’s got a knack for being the ‘first lesbian experience’ for a lot of girls.
I remember her scoring this 10/10 singer, and bragging about how they fucked in her room for the entire Marian Hill discography. I’m pretty sure that’s like seven hours. I imagined her and that busty blonde singer in there, sweaty and hot after hours fucking and licking each other’s pussies. I jerked off to it, but no more than I jerk off thinking about all my female friends. Other than that, there’d never been a sexual moment between us. We both stripped naked for a drunken sauna once, but never laid an eye or finger on each other… until last month.
Just after Valentine’s, we both flew up to San Francisco to location scout for an art film that’s going up in a big contemporary art museum in the US this summer. I would probably get doxed if I name the place, but maybe someone here will figure it out. If you come to the reception in August you’ll probably meet us. Wouldn’t that be weird?
Anyway, I directed and she was the producer, so the two of us flew up together for six days to scout. Normally we’d stay with my aunt in Berkeley, but because of all this COVID bullshit we decided to just crash on the floor of the first location, like the pretentious art kids we are. It’s this big industrial tenement penthouse in the Tenderloin, which is the ultimate shittiest part of San Francisco. Needles, psychos, schizo homeless dudes. The apartment itself is kinda like the apartment from After Hours, if you’ve ever seen it. No furniture, just a big mattress we laid out on the living room floor.
The first two days we spend actually scouting. We do our best to make it fun, but there’s basically nothing to do in the touristy areas during the virus. Then, on the second evening, I crack a joke about a big massage parlor across the road. It’s a crummy 70s building, dingy Chinese text down the side. You know, a brothel. The kind the liberal city of SF doesn’t like to shut down. That’s when Melissa jokes that she wants to check it out.
I called her bluff right away, basically saying, fuck it, why not? But we gotta get kinda drunk before we go. We buy a bottle of soju and split it, getting a little more trashed than I expected. This whole time I’m nervous ’cause I really have no idea how this is going to go. I’ve been to places like this a few times, getting a handjob from a sweet Chinese MILF after a massage, but never with a friend or a woman.
Then we head down to the place. The inside is honestly hilarious. It’s maybe eight or nine Asian girls sitting around, eating chow mein and playing video games or reading the paper. Like something you’d see in an old french movie. The ‘madam’ is up front, and she looks at us like she’s thinking, god damn, is this another dumbass couple looking for a regular massage? I ask her for two half-hours, dropping cash on the counter like I know what I’m doing. She asks ‘separate or together,’ and I’m about to say ‘separate’ (of course) when Melissa straight up just says, ‘together.’
Now I’m even more curious to see how the fuck this goes. Probably an awkward, overpriced couple’s massage. We go up to a dark, perfumed room with two tables, and the madam leaves us alone. I explain that they want us to strip naked, and Melissa starts giving me lighthearted shit like I’m some kind of regular to these spots. I’m too drunk to feign total innocence at this point. Stripping here is way more intimate than that sauna, and I feel myself acutely aware of her small tits and bush as she takes her suit off. It’s all I can do to lie face-down on my table, towel over my ass, before she sees I’m hard.
Then the girls come in. Mine was a Thai chick, maybe 27, with a cute face and smart eyes. Like someone you’d see in a library. I can’t remember Melissa’s masseuse too well, but I think it was a darker and older Asian woman with a bob. They oil us up, and as the massage starts I’m fucking diamonds. Just thinking about the other masseuse touching Melissa’s skin has me rock hard, even more than the woman’s hands on mine.
Twenty minutes in, I can’t fucking help it. My masseuse turns me over, exposing my cock for a second, and in that moment I run my hand up the inside of my girl’s yoga pant leg. I pause a moment, feeling her warm lips through the synthetic material. She giggles, and she whispers to me, ‘girlfriend?’
I’m confused, but she points to Melissa. ‘No,’ I say back, kinda loud and awkward. ‘No just my friend.’ In that moment, I swear I hear Melissa moan a little, maybe not. Then I feel my masseuse’s soft little hands cup my balls. ‘You want?’ she whispers, miming jerking off. I can’t fucking say no, but I also don’t want to be way outta line in front of a good friend. So I summon some drunken idiot candor and mumble, ‘Hey Melissa? This, uh, this girl wants to, uhh, finish me off. Is that okay?’
Her answer, with this kind of shameless deadpan, ‘You do you bro.’ I take that for a yes, and the Thai girl starts to stroke me off just a few feet from my best friend of like six years. I have a huge oh shit moment, but that’s even hotter. I focus on the Thai girl, feeling up her tits and round ass. Then I hear a new sound from the other table. The milfy masseuse is leaned over Melissa, rubbing her off with super fast fingering from behind. I never knew if or how these places serve women, but I guess that’s how. In the dark, I can’t tell if Melissa’s watching me, but I can’t help it. I watch her fat ass jiggle against the masseuse’s arm as she moans and grips the table. Then I bust. Pretty soon she busts too. Then I’m lying there naked, next to my friend, cum all over my chest. Fuck.
The post nut embarrassment hits me kinda strong. Then I remember she just got fucking jerked off too. The Thai girl brings us hot towels and we clean up in this kind of dazed, drunken haze, totally spaced out from cumming and not sure what to say. I tip like a hundred dollars for the two of us, and we go back over to the place where we’re staying.
It’s maybe an hour before Melissa lights a blunt on the balcony, and we start to talk about it. She says something about supporting sex workers at some point, and I laugh. I guess everything is political in a way. I don’t dare admit that I was fantasizing about her. She’s pretty chaste too, for someone I just watched have a writhing orgasm. But she says it was a ‘fascinating experience’ and she doesn’t regret it.
That’s the first of three things that happened on this trip. The second started three days later, after we’d been at least a little productive and finished the work my 1st AD said was completely essential. Then we tripped mushrooms and walked around the city for about seven hours.
That night, we were eating takeout from this French spot. Our feet were killing us, so we were sitting on the floor of the apartment with our shoes off, polishing off a bottle of white wine. The mushrooms were pretty much worn off. The conversation came back around to our trip so far, and I mentioned that the massage place was a ‘fun and unexpected highlight for sure.’ She tried to brush it off, but I held her to it, saying it was her idea and that it was cool to see that side of her. I didn’t mention how many loads I had busted in the sink since then thinking of her naked ass with a hand up under it.
‘It was interesting,’ she said in a pause, like she was describing a cool lecture or a screening. ‘What I really wanted was to lay her down on the table and ride her face’
I think I almost came right there. A crazy feeling swept over me, and I said, ‘you could do that. Probably. But not at a massage place.’ I’d never called up an escort or anything like that before, but I went on a certain Australian website and browsed SF escort profiles in the local area.
We found a Chinese-American girl named Charlotte, who to both of our interest was a statuesque 5’10”. She did men, women, and couples, she said. Down for anything, clean and tested, $600 a night. I will defend my reputation by saying that we did not play into the Hollywood stereotype and pay for hookers with the movie budget. We put the phone on speaker and call her ‘just to say hi.’ After a short call, during which we assured her our sketchy address was not a murder plan (despite my username), she convinced Melissa to bring her by to hang out ‘no pressure.’ If nothing happened, she’d just eat some of our French food (I forget the gd name of the place but it impressed Charlotte) and then move on with her night.
[CONTINUED IN PART TWO HERE.](https://reddit.com/r/gonewildstories/comments/mh3nos/san_fransisco_hookers_and_my_lesbian_friend_mff/)
Source: reddit.com/r/gonewildstories/comments/mh3m05/san_fransisco_hookers_and_my_lesbian_friend_mff
Oh nice!