This sounds awful, but I was so desperate for money that I posted on Craigslist. Obviously that was stupid and dangerous, but I was 17 and I didn’t think about it.
I basically asked people to bid to see who I would go with. Keep in mind this was a suburb in the Midwestern US, so the money wasn’t crazy. I ended up driving 45 minutes to meet a guy who then drove me to his house. Again, so stupid. I can’t believe I didn’t die that night. This dude was like 50, heavy cigarette smoker, smelled like booze. I told him I was 19.
The guy paid me $60/hr for three hours. He smoked a few bowls, talked about jazz, and then very creepily went on and on about my boobs. I jerked him for like 30 minutes with this horrible rose-scented lotion, blew him, and eventually we had sex. I was impressed he could get it up with how high he was and figured he must be on something else. That’s mostly what I was thinking about the whole time.
At 20, I was on Adult Friend Finder when I was offered $2,000 for two hours of my time and a few snaps with his cock inside me. He was a 65-year-old man. The sex was pretty good, and I got off on the notion that he was paying to fuck me. Honestly, holding the money in my hand afterwards turned me on much that I masturbated the second I got home with the envelope in my hand.
3. The Male Escort
I’m a straight male escort and my first day of work was definitely not what I expected. In a typical booking, you meet, chat for a bit, sort out business, ask the client to shower then get down to business. For me, that generally includes a massage, foreplay, sex and a fair bit of conversation.
For my first booking, I received an email from a girl that basically went as follows: “Hi, I’d like to book you as a birthday present for my friend’s 24th surprise party.”
I turned up early to help these girls prepare the surprise and they’re all insanely attractive. Out-of-my-league attractive. The girl who booked me then drops this bombshell on me: “Oh, by the way, all of us girls are either escorts or strippers.” Uh oh, I’m in way over my head… I do my best to remain calm and collected and we all enjoy ourselves before the birthday girl shows up. They all turn out to be lovely girls and we all had a fun night. No actual sex, but there were a few shenanigans that went on.
4. Double Assignments
I had two clients my first day.
The first guy was really nice. Mid 30’s, extremely average looking. We started out with small talk. He offered me a bowl, which I refused. He smoked a little and then eventually kissed me. He had a bit of an ass fetish, I let him eat my asshole and lightly spank me, and then I let him put it in my ass– I figured that it was my first client, I should do a good job. I still see him from time to time, and he always tips very well.
The second guy didn’t even try to have sex with me, he wanted me to smoke a cigarette while watching him masturbate. That’s about it. He paid me for an hour without question and I never saw him again.
5. Cash Toss
When I was 18 I was looking for a sugar daddy when the CMO of a very well known company offered me $1000 for the hour if I came to his hotel room. I hadn’t considered transactional sex for money before but I was interested with the price so I showed up, got my money in about three minutes and went home with an uncontrollably large smile on my face.
The only awkward part of the night was when he finished rather quickly and then, I’m assuming from embarrassment, threw the cash at the door and asked me to leave.
6. The Real Name
I was an independent escort for 4 years. My first night, I was ridiculously nervous.
I went to an upscale hotel, nervously walked thru the lobby, hoping I looked like I belonged there, and not like what I was really there for. I was nervous the whole elevator ride up to his room. I walk to his room, lightly knock on the door. He opens the door, says (for the story’s sake, we will use the name Sarah) “Hi, Sarah?” and like an idiot I reply with my real name. We laughed it off. It was quick, 10 minutes. He was polite and clean. In the area for business. I ended up seeing him a few more times over the years, always very nice. Tipped on top of the hourly rate, which was always appreciated and made me choose to see him over other clients in the future.
7. The Opera Guy
My first guy said he was just looking for a blowjob, so I saw it as a very easy job, but then he wanted to talk for a while first. He was talking about Opera and I mentioned having sang a certain piece in choir, so he ended up asking me to sing, which was really strange. The first blowjob was pretty normal. He had asked if he could cum on my face and/or tits and I’d said OK, so I was expecting that. After he came, he put his dick back in my face and he told me to suck him hard again. Then he told me we had 20 minutes left and told me to lay on my back on the bed, with my head off the edge. I figured he was going for sex and reached for a condom, and instead he told me know and that he wanted to “face fuck” me. He came a lot faster that time, pulled out and came on my face. He yelled at me not to wipe it off and to leave it there until he left, then asked me to stand up and sing for him again while he was getting dressed. It was kind of surreal.
8. Accidental Escort
When I was 20 I used to troll around on Grindr for guys, and one day this guy messages me to hook up. He seemed to be the older type and I was interested so we met at a Starbucks to see if we liked each other. He turned out to be a fairly fit man in his late 40’s that was still quite handsome.
We chatted each other up and he was really nervous, and admitted it was his first time. We eventually went out to dinner and went back to my place where we had sex. I was letting him sleep over but he suddenly had urgent business at 3am in the morning so he left. When I woke up I found that he had left 300 dollars on my desk. Honestly at first I wasn’t happy because I’m not a whore and I didn’t need the money but I figured what the hell and got over it.
9. First and Last Time
He was in his 40s, from another town, and offered me $900 for the night. When the night came along, he booked a hotel, and I went over there some time that evening. I was so nervous I could barely speak a word when I got there. He was an average looking guy. I wasn’t attracted to him but it didn’t cross my mind that it mattered. I was still about to have sex with someone I technically just met, and for money. He ended up offering drinks (yes, I know how stupid this was now that I think about it) and I got drunk enough eventually to relax a lot more.
Once I was relaxed, he started kissing me, we eventually got naked, performed oral. We had sex twice and he got off in less than two minutes each time. Which was a really good thing because he was bigger than I expected too. After that, we just went to sleep and I left in the morning. Yes, I stayed overnight, which was probably another dumb thing to do but oh well.
10. Involuntary Crying
My first job was a private client, and I was totally calm on my way there and during, it wasn’t until I got into a cab to go home that I started crying. I wasn’t even upset; it was just involuntary. A month later I joined an agency my first night they gave me this guy who became my first regular, always booked half an hour and I never stayed longer than 10. The other job of the night was in an office in an old industrial estate, two very married men and another escort. She was really nice and reassuring and helped me get over the initial embarrassment. The rest of the night was just sitting in the car with my driver talking about WW2 and listening to Frank Sinatra. Most of the time I even had fun! But I still always got butterflies on the drive there.
11. The Dark Fantasies
I was “in-between employment” and talking in a philosophy-oriented discussion forum and started talking to a woman there. She was a practicing Freudian psychoanalyst. We began discussing sexual proclivities, and she confessed that she wanted to explore some kinky fantasies she had, and wondered if I would write her some erotic fiction on a number of themes. I agreed, and she enjoyed them immensely.
We talked more in-depth and a month after we first talked, she offered to fly me to her, put me up in a hotel for two weeks, and pay me a sum of money to act out her fantasies with her. I considered it. She insisted on it being a business arrangement, so that she wouldn’t “catch feelings” and because of the rather intense nature of her fantasies – “buying a sex slave” was part of them. I finally agreed.
Two weeks of debauchery ensued. Sex while reciting poetry, sex while drunk, sex in public, sex at a private party with an audience, domination, submission, role-play, on the roof of a high-rise in a thunderstorm half-expecting to die of a lightning strike. Waking up tired, sore, bruised, and mildly dehydrated was the norm. I tied her up, suspended her in a web of ropes, and thrummed them with a cello bow until she orgasmed from the sensation and the verbal accompaniment. She placed a rather vicious dog’s choke collar on me, chained me, and proceeded to entice and humiliate and tease me for hours.
Over time, we met for sex a few more instances – but we inevitably had developed feelings for each other, and so discontinued the business end of the arrangement.
12. Sugar Baby
I had heard of a website for a sugar baby/daddy’s and decided to try it out. After weeding through all of the messages I got, I found a guy that was actually attractive and had chemistry with, so we decide to meet up at his place.
The drive over I almost turned around 5 times, I was so nervous. I knock on his door and he looks mostly like his pics, just a little older and shorter. It was both of our first times so we have no idea what to do. We sat on the couch, talked and put on a movie. Afterwards we go to the bedroom and fool around and do everything but sex (I was too nervous). It was great and I spent the night. He ended up paying for my rent ($670) and a new phone ($500).
13. The Blindfold
I found this married guy. He ordered things off of Amazon for me to bring (we’re talking bondage/anal stuff). Anal was on the list of “necessities” to him. I was an anal virgin and reaaallly hesitant about it. I told him I wanted to be blindfolded for the thrill of it, but really, I just didn’t want to see his face. I drove to his hotel and he instructed me to put the blindfold on and I did.
I hated it. I hated every minute of it. I could feel his fat slapping against my stomach. I wanted to vomit. He gave me the $400 and I left. I cried all the way home.
This dude was convinced that I wasn’t in it for the money. I had a sick mind, I had a dirty side, and only he could fulfill it. I didn’t bother correcting him because I didn’t want to kill the self-esteem he was building for himself.
I told him I couldn’t do it anymore. He messaged me a few times over the next year but I kept telling him no, no matter what price he gave me.
I regret it to this day and nobody knows about it.
14. The Fetish Guy
I was extremely nervous but I had an experienced girl showing me the ropes.
My first call was asking for a duo, which made me feel a lot more comfortable with the whole situation. He was a pretty good-looking 40-ish year old businessman. Then he explained his fetish. He wanted us to feed him his cum. So we both fool around with him and he ends up banging me while my friend watches.
He finished on his stomach and I scooped it up with a spoon. Had to force him because that’s what he was into. I felt pretty gross, he got dressed and left and I made a quick 120 bucks.
15. Spaghetti Dinner
I was 22, just graduated with a BA in a major that would make me no money.
I posted on Craigslist and met a man the next night at his house for an agreed-upon 30 minutes. We sat on the couch and talked a little bit.
He took me into the bedroom and there were lit candles and a bottle of lube on the nightstand. I wouldn’t kiss him for awhile, but he seemed lonely I guess? I eventually did. He put a condom on and I blew him for awhile, but he didn’t stay hard consistently. I climbed on and rode him and he didn’t come by the time the 30 minutes were up. I liked him, so I kept going until he finished — maybe another 20 minutes? I didn’t charge him for the extra. I didn’t enjoy it as much as I would with a regular partner, but it wasn’t bad. After we finished he thanked me and we hugged. He suggested that next time he make a spaghetti dinner and we could eat and get to know each other.