*****
This whole job started in the October of my freshman year at college. I didn't live on campus, but I had a friend who let me stay at his apartment if I paid rent and did some chores. I'm grateful for that; it's expensive as all hell to live in New York City otherwise.
His apartment had a shitty old couch that he wanted to get rid of. He gave me that task, and said that we could probably get some money for it if I sold it on Craigslist. I had made it a point to never use that site, I'd heard too many horror stories about it, but I used it anyway since he asked.
I used his account to set up an ad for the old couch and set the price at $100, with some wiggle room. Since I was already browsing, I just looked through the local ads and I found several more reasons why it was a good call to never use Craigslist. The crazier ads aren't extremely common, but they're pretty out there. One asked for a person to anonymously send a 2 Liter bottle full of urine for $500. There were several ads for guys asking other guys to jerk off with them for whatever reason, and every single one took care to mention that the poster wasn't gay. I found an ad from a dental assistant who wanted to use alginate, that weird gummy stuff dentists use to make molds of teeth, to make a mold of somebody's bare ass. New York City is a big place, and there's room for every kind of weirdo imaginable.
It was during this fall down the rabbit hole that I found an ad that got my attention. It was asking for a "cuddle buddy" (their term) to spend a weekend at their apartment. There would be constant hugging, cuddling, and spooning, but nothing sexual. I had my doubts about that last part.
What really surprised me was that the person was offering $300 for a 3-day, 2-night stay. That's a lot of money to pay somebody to let you hug them. I remember being incredulous that nobody had taken this offer yet. It was creepy, but if you had a means to protect yourself and didn't do anything stupid you'd be fine. That was when I realized that I was acting like I really wanted to do it.
I'm asexual, at least at this point in my life. I like masturbation and orgasms as much as the next guy, but I never really had any interest in putting another person into the equation. I was a virgin and didn't give a shit. I still am now and still don't care. The problem was, I really liked cuddling. It made me really happy. Back at home I could cuddle with the family dog all the time, and I really liked cuddling with girlfriends and boyfriends I'd had in high school.
(Yes, I tried dating boys. I assumed that since I had no sexual interest in girls I had to be gay. The guys didn't make me want to have sex, either.)
The problem is that it's hard to get cuddling when you're away from home and don't want to have sex. I missed it. Against my better judgment, I made my own account on Craigslist and accepted the ad's offer. Right after I was done I bought some Mace.
As it turns out, I didn't need it. The lady who sent out the ad was just middle aged, lonely, and wanted to be held by somebody. It felt odd, since I was 18 at the time, but we made it work. It was the easiest $300 I ever made, hands down.
It got me thinking, if there were other people in this city like me, and with 8 million people there had to be, I could set up an ad like it and maybe get a hit, except I'd be offering to sell my cuddling. I set up an ad for a weekend of cuddling for $100 and I got an offer within a week. I was extremely cautious, but it worked out. I ended up doing two more of these weekend rentals during my first semester.
My roommate thought it was weird, but he couldn't argue with results. Still, my parents wanted him to keep an eye on me, so he wanted me to not use Craigslist and instead make my own website. He was in school to be a lawyer, so he helped out with making up contracts and properly setting things up.
I thought that without Craigslist, nobody would know about me, but the Internet always has answers. People who are serious enough about cuddling to hire somebody for it tended to form online communities, so when I made my business known to those groups, people showed interest. It was infrequent for the first year, but as I did it more, more people heard about me and wanted to rent me. By the end of my sophomore year, I was getting about 2 offers a month, in New York City and the surrounding area. A majority of my clients were men, and you can interpret that information any way you want.
I only offered weekend stays, and always at a flat rate of $300, half to be paid in advance. That seems really high, and it is, but there are actual professional cuddlers out there (just that term sounds ridiculous, doesn't it?) that are much more expensive, like $100 an hour. I'd essentially offer to be a pet for a weekend for a much lower hourly rate.
I didn't care for the term "professional cuddler", but that's what I had to use officially. Still, I had a much better term for it I'd use in private. Ever since my roommate pointed out that this is like being a hooker, but seen through the eyes of a child, I called it PG Prostitution. It fit.
You might be thinking that this is a dangerous job, that it would be easy for predators to take advantage. You'd be right, but I was careful. I didn't have a PG Pimp, so I had to take steps to protect myself on my own. I always had the Mace with me and always told my roommate the addresses of the places I went to.
This job meant that I met all sorts of people. I held and was held by folks from all stripes. One thing I learned early on is that it was easy for me to get them to tell me stories. I'm not sure why, maybe I just came off as really trustworthy. I realized that if I asked a client about their craziest or most embarrassing story, they'd usually tell it. I also learned that most people's craziest or most embarrassing stories had sex involved in them. This post is going to be a collection of stories, about my own experiences, and those of my clients (with names changed to maintain anonymity) in my days as a PG Prostitute.
*****
Brad bought me the weekend right after my services were purchased by Ian. He was aggressive, holding my face, hugging me tight, and kissing me often. He obeyed all the rules, but was all over me at pretty much any time he wasn't doing something else. He was much bigger than me and had quite a bit of muscle, so he would lift me up and carry me around several times. He told me that I was cute often, gave me the nickname "puppy," and on more than one occasion asked me if I was absolutely, 100%
sure
I was asexual. He definitely flirted with me, but he never made a move. I had experienced clients like him before, but I was already on friendly terms with the guy, so it wasn't
too
weird.
Hanging out with him for a weekend meant that we had plenty of time to talk. My suspicion that he really got around was confirmed and then trampled to death. At one point I asked him if he knew how many men he had had sex with and he said it had to have been more than three hundred. At 25, that's fucking insane. He was strictly in the one-night-stand, hump 'em and dump 'em camp; he didn't like commitment and didn't see himself settling down any time soon. He was a strict top, never forgot condoms, and almost never banged the same guy more than once. It's a good thing he lived in a huge city.
I heard some pretty crazy stories from him. My favorite was the one he told me when we were cuddling on his bed Saturday morning.
"Have you ever stuck your dick in crazy?" I asked. This was a prompt I often used to get good stories.
"Of course, puppy. I could have been arrested because of this one guy."
"How'd that happen?"
"It was spring break of my senior year, and I had gone to the Florida Keys for it. Great sights, great towns, great sex. One day I was at the beach and I struck up a conversation with this dude who couldn't have been more obvious about his intentions if he tried. He wanted to do it immediately, but I was in the mood to take a swim, tan a bit, play volleyball, y'know,
beach stuff
."
"You said no to a sex proposition?"
"No, I said 'give me an hour at least' to one. This guy was either on drugs or just bat-shit crazy, though, because he refused to wait. I was snorkeling when he swam up to me and I saw through my mask that he was stark naked. I didn't even see his trunks in his hand. He ripped them off and just threw them away at a fucking public beach!"
My eyes widened.
He chuckled. "Hold on, puppy, it gets worse. Before I could say anything, he goes under and takes off my swimsuit, too! I tried to kick his ass, but he must have done this before or something because he was able to evade me and get away, no problem. Maybe I just overestimated how well I could move while in the water."
"Did nobody else see you?"
"They saw us, but weren't close enough to see we were free balling. I finally catch up to him and he's just grinning like an idiot with my swimsuit balled up in his fist. He's acting like this is all fun and games. I tell him to give it back and he says he would after I fuck him."
My jaw dropped. "In public?"
He nodded. "Naturally, I told him to eat shit and give me back my pants, but then he
puts it in his fucking mouth
. It was a Speedo, a small one to show off my assets, so it fit. He tells me that if I don't fuck him, he'd swallow it."
"Could he have actually done that? It sounds like it would be too big to swallow."
"Don't know, but considering all the shit he pulled, he would have at least tried. I figured I had two options, either do what he says, or get away and call for help. The first option had the possibility of my cock
not
being exposed to a bunch of strangers and children, so I went with that one. Still, if anyone saw us, we were in serious trouble. Public nudity is one thing, but fucking in public is way worse. This meant it needed to be quick."
