Does bus fare and dinner count? I had a guy pay to have me join him on a… heh… layover at the NJ airport in exchange for a night (and morning) of debauchery.
Best trip to NJ eva. 
Clawing one’s eyeballs out is pretty much a one-way trip, I hear.
I haven’t, since I refused it, but there was one incident (at 11) when a guy waving a lot of money asked me to accompany him saying he “was lonely” and I “seem like a nice girl;” there were others where different people tried to pimp me out (at 15, my host family in Ireland and their neighbor who was a police sergeant, to my host-father’s boss, within 24h of being in the country and by the method of bringing me to a disco where it was illegal for me to be and leaving without me; at 18, my grandfather). I never bothered count the dirty shitbags who’d offer me money and ask for “services” at times when I was walking down a street at night in Barcelona.
I was a teen, he was a virgin guy I grew up with and I took it on as a dare.
I think I got enough to buy one of those hideous stonewashed denim Guess jackets that were so hot in the eighties. Not sure, maybe fifty dollars? He’d stolen it from his mother’s purse and called me later that night begging for it back.
Yeah like THAT was going to happen! And I never felt the least bit guilty for it.
A near miss but not exactly…
I was 16 or so and was sort of summer dating a girl 15 (I think). I had (some) experience with sex and she had none, a big ol’ zero. We were at her place one day and she suddenly decided today was her day and I was the one.
Well and good! says I. Being 16 I wasn’t looking this good fortune in the mouth. Be honest, now, which of you would?
So we do it. Fine and dandy. Then we start listening to Led Zeppelin (for a teeny girl into pink and bunnies and such she loved heavy metal and classic rock). Her mom comes home, maybe 1/2 hour after we’re done. I’m feeling a little weird about it, I admit, and then her mom asks me if I’ll mow their lawn for $10. Embarrassed, I offer to do it for free. She calls me a nice Jewish boy (they were Jewish, too) but insists on giving me the $10 for the half-hour it took me to do the job.
The whole time the girl swung on her swingset (left over from when she was very young) and watched me mow her lawn with my shirt off.
Still, one of the weirder experiences of my teen years.
A few years ago, a girl down the hall (I lived in a co-ed dorm) offered to pay me $50 to have sex with her shy roommate. I told her I’d do it (i.e., her) for free, and I did. It wasn’t a bad time, all in all.
Wow, sounds like a class act.
I know you said he was a virgin, not that you were, but I wish I’d gotten something more than a sore ass and vagina when I lost mine.
I lost mine to a family member when I was six. I assure you it wasn’t pleasant.
I had some really stupid screwed up ideas about sex when I was younger. I saw it as a tool, nothing more, and didn’t much enjoy myself until a few years ago.
It’s hard to believe that guy is almost forty now and so am I. Wonder what his life turned out like with me as his first.
You had anal sex your first time?!
Yossel the Hassid is in London on business. It’s now one hour to shabbos and he’s all dressed up in his shabbos clothes ready to go to a local shul.
He takes the lift to the ground floor and walks towards the exit. As he reaches the reception area he sees a stunning British Airways hostess with blond hair and a face and figure you could die for.
She has just checked in. As soon as she sees Yossel, she stops in her tracks and walks quickly over to him.
“Hello,” she says to him.
“Hello to you, too,” he says.
“I have a confession to make,” she says.
“What is it?” he asks.
“I have a sexual fantasy,” she says.
“Nu, so go on,” he says.
“I’ve always wanted to be with a Hassidic man.”
“I want to run my hands up and down his white silk socks, run my hands over his tzitzis and my fingers through his beard, play with his peyess, eat kichel with him, poke my finger in his puppik, remove his gatkes, play with his shlong and then shtup. So I want you to join me now. I have a room upstairs just waiting for us. What do you say?”
Yossel looks at her thoughtfully and says…
“And what’s in it for me?”
OK - old joke.
In reply to the OP:
In my 20’s, and as a Gay young lad, I went with a straight German guy (also in his 20’s) to a bar in Berlin. He found two women - today we would call them “cougars” I guess - who were probably in their late 30’s or early 40’s. He was all over one of the women and I sat there with the other…she didn’t know my story, but we had a few beers and then she came on to me with this line:
“I used to be a prostitute. I think you’re cute - how much do you want to spend the night with me?”
Obviously, it didn’t happen…but it was flattering. Always wondered how much I could have asked for…
Presumably they did it somewhere uncomfortable, like on the ground, or in the back seat of a Honda (it’s the American way!)
Never. But when I was a summer camp counselor the Campfire Girls gave me the “Sexiest Legs Award,” so that should count for something, right? Right???
I can parse this two ways:
How much do you want (to pay me in order to be allowed) to spend the night with me?
OR
How much do you want (me to give you so that you will) spend the night with me?
I had both. 
I once ran into one of my high school teachers struggling with a flat tire at a shopping mall. I gave her a ride home, came back, got the tire fixed, the good one back on her car, drover her car to her house and we spent the afternoon together before she drove me back to her car.
Not payment exactly, but in my mind it was thank you for services rendered.
I’ve been propositioned twice. Once by a guy a knew, and once by a random old man at Trader Joe’s. :eek: I can’t say which was more disturbing. I suppose the old man at the grocery store. I was actually seriously considering it the first time, but I was super poor and maybe 19, and the guy didn’t have any (visible) warts or anything.
Also: How much do you want (desire) to spend the night with me?
Perhaps this deserves its own thread, but I know we’ve done it before, so I’ll just ask here: what would it take?
That is, there are plenty of “I almost…” moments described above. How much cash would it take to agree to sex with a nondescript stranger of your preferred gender? This is someone not gorgeous and not ugly either… just average-looking. What would it cost if the client asked for unprotected sex?
I am obviously male but I think I could go for $1000. Despite what people think my user name means, I am fairly pure so that would have to be taken into consideration. The unprotected sex part is a lot harder. I wouldn’t be so much worried about STD’s as fathering another child. That would end up costing me in every way for life.
Not much at all, maybe $50-$100. Nothing inherently wrong with it, IMHO.
However much it took to feed and house me while I accompanied her through the most comprehensive battery of STD testing and IUD insertions you could possibly imagine.