Virginity is a bit of a weird concept. I'd never had actual sex before a couple of weeks ago — I grew up shy and had bad body acne for the longest time (the two not unrelated) — but I've been known to hang out at BDSM clubs, and I've had lots of e-mail sex with a long-distance ex — we got off to each other's stories many times. (Unfortunately we broke up before trying anything in person). She had a lot more experience than me, and gave me a lot of feedback on what would or would not actually work. I guess this made me a bit of an odd virgin.
I've never had serious moral objections to sex work, in principle, done with full consent, but I'd never really considered it, because I figured it would be difficult to tell if a sex worker was exploited or coerced, and I want no part in that.
But one night I found myself browsing the online directory of a local independent escorts collective, and looking at those women's web sites, I couldn't see any reason to think this was exploitative. One woman in particular really caught my attention – a pretty redhead with references from Hitchhiker's Guide to the Galaxy and the Little Prince on her web site. She came across as smart and charming. I have a really hard time imagining that someone being forced into sex work would make a web site with Little Prince references in it. Her rates were high, which I figure is a good sign, since it means she doesn't have to have that many clients — so she is free to turn any particular client down. After much hesitation I emailed her (shooting off a few geeky references of my own), and we set up a date for the following week.
I got there, and was nervous as hell, but she was kinda used to that. We chatted over coffee and wine for almost an hour. We talked about video games and work, I checked out her collection of vintage japanese RPGs.
Eventually we moved to the bedroom. She undressed herself, I pulled my shirt off, self-consciously. She was pretty, but not model pretty; that made me feel a bit better. She had a few scars of her own, but that didn't detract from how hot she was. She left the room for a bit and came back with her magic wand in hand (I'd previously asked if she had one over e-mail, I'm a bit obsessed with the thing), and put it down on the bed. Then we kissed for a while, and I explored her body, until she kissed down mine, and pulled my pants and underwear off.
She kissed and licked and sucked my balls, then my shaft, and took me in her mouth. She started deepthroating me. I could tell she was really good at this but my nerves prevented me from really enjoying the experience.
After a while I was feeling a bit bad because I wasn't enjoying it that much and was nowhere near finishing, and she was really giving it her all. I flipped her over and grabbed the magic wand. She took it from me, turned it on on the high setting, handed it back, and spread her legs. The nice thing about a magic wand is that you don't exactly need a lot of skills to operate it. It's not exactly a precision instrument. I pressed it against her vulva and clit and she started moaning loudly. Before long she was having a shaking orgasm.
I rolled over — she grabbed a condom, put it on me, and guided me inside her. She rode me until I flipped her over, and then I fucked her for a while. She was moaning and grabbing my hair and pulling me into her. I was getting tired and still not really close to finishing (nerves again) and I guess she could tell because she pushed me over, and started sucking me. She did that for a while but it still wasn't doing much for me so I pulled her up and kissed her instead.
I positioned her over me and she started grinding herself on the base of my cock, while I caressed her belly and thighs. She was grinding hard, going faster and faster, until she came. Physically I didn't get much out of it but it was really hot to watch. She made a bit of a mess; she apologized for coming all over me and wiped her wetness off me with a towel.
I guided her to lay on her belly and laid down on top of her, pressing my cock against her ass, and reached around to finger her. I rubbed her pussy for a bit – hopefully her clit – and she moaned and pretended to enjoy it (let's face it, I had no idea what I was doing).
I put on a new condom and started fucking her from behind. I shifted around to find a comfortable position, and settled on half-laying on top of her, so that I could kiss her neck while thrusting into her. I was going at a medium pace, experimentally. I shifted around and tried a few different angles and rhythms. Then I tried slowly thrusting all the way inside her, I mean really all the way, with enough force to push her hips down into the mattress and squish her ass against my hips, and oh fuck. I just pressed down into her and stayed there for a bit – the way she was moaning and gasping at this point – she seemed to enjoy it too. Then I started fucking her with long slow strokes, pushing her hips down into the mattress at the end of each thrust. The last inch or so felt really good. At this point I couldn't resist fucking her faster, still going all the way inside her with each thrust, until my whole body tensed up in pleasure, as I thrust myself deep in her one last time and came. I stayed inside her and we cuddled for a bit.
After cleaning up we talked about whatever, ordered food and watched a few youtube videos, and I left.
Mostly I wrote this down for myself, but I figured I'd publish it, since there's a lot of shame and shadyness around sex work, both on the clients and workers side, and I wanted to show it's not always terrible.
tl;dr I don't always hire prostitutes, but when I do they own Chrono Trigger on SNES and enjoy kissing and cuddling.
Source: reddit.com/r/gonewildstories/comments/3xrc94/that_time_i_lost_my_virginity_to_a_sex_worker_i
http://img.pandawhale.com/39594-Leo-DiCaprio-Great-Gatsby-upvo-hVno.gif I suggest you x-post this to /r/hookers
But there’s so many of those disgusting sites.. Like which one was it?
The site, with the info I’ve given, would basically uniquely identify her, which she may not want. It’s not even in the US though.
Dude, she’s a pro. She’d probably appreciate the free publicity and great review. Also, I’ve heard of gfe but this is the jackpot. I’m surprised she didn’t introduce you to her parents.
Tell me something, at any time did you feel she was like "faking" it or acting? As a woman, the idea of paying some guy to have sex with me looks totally out of whack, but I realize we girls have an easier time finding a hook up if we want than you guys.
It’s kind of out of whack… I mean if you can get laid any other way by all means do that rather than pay for it. But it’s better than nothing. I’m sure she was faking some parts. It was actually a bit distracting because I kept wondering which parts. I can believe she actually came from grinding on me, since she was in control, but I inserted a finger in her and she was moaning "uncontrollably" and I was like… Yeah no. What bothers me more is how friendly she was outside sex, and I can’t tell if she’s faking. Like… she sort of gave me her phone number, after telling me she never gives it to clients. (Sort of because she was telling me how geeky her phone number is, which to be fair it is, so it made sense to tell me, not necessarily in a "call me" sort of way. I didn’t write it down). And told me I should keep her updated even if I don’t hire her again. But like… I’m autistic enough that I basically cannot read people. So I sort of always feel this way about people. Like, I had this girl friend come over and cuddle with me and play with my belly while reading and laughing at Cosmo sex tips. Another time we were sleeping at a friends place and she (jokingly? flirtily?) insisted we sleep in the same bed and it only occured to me like 2 years later that maybe she wanted to sleep with me