All stories we shared here is has been told exactly as it occurred, and all names have been changed for privacy reason.
1. Degree with no money, left to own device
I was 22, just graduated with a BA in a major that would make me no money. Moved in with my parents and was on a downward spiral.
I posted on Craigslist (£400 an hour, I had no clue about rates and still don’t but from this thread it seems high) 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 ran a small business, divorced, overweight, 40s. Really ordinary and quite nice, actually.
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. (Stupid, probably.) 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.
It wasn’t as bad as I had expected, and I wasn’t traumatized, but I never did it again. I’m not sure why. He texted me several times after and eventually I told him I’d moved.
2 Lucked out!
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. I have dozens of other stories if anyone is interested in hearing!
3. Happy ending?
2013, I am an exceptionally naive 22 year old with six figure debt from a failed marriage and a baby to support on my own. A year before I had been approached by a friend of my sister who offered me a job as an escort. A had no idea what an escort did but the offer of £150 an hour remained in my mind and I called the guy when I reached as low as I was willing to go. I thought escorts danced or masturbated, I wasn’t even a good dancer. I have no idea what I was thinking.
Looking back, my first appointment was a disaster. John was exceptionally patient but I was so anxious. We had a drink, smoked a bowl, and he offered me some coke. Never have done coke before, I hoped it would help my nerves and obliged myself to his offer. That obviously didn’t work. Another hour of chatter and he asked me what I could do, sensing I wasn’t exactly on firm footing with the current endeavor. I had brought a bag of lingerie and offered to model it for him. Somehow this was sufficient for him and the drive home later was to this day one of the most fun drives I have ever had.
Of all the things in life I am thankful for, few rate higher than my dislike of coke. Instead of getting sucked into all that, I got myself out of debt, bought a house and went back to school. Graduated two weeks ago debt free with one of the most sought after degrees from a prestigious school. I have been working independently since 2005 and currently work one £1500 session a week (all my clients I have had more than five years). It has been a lifestyle that has served me well, I have met amazing people and had unforgettable experiences that would otherwise been impossible. Retiring is one of the harder things I have to do but in three months I hang up my heels and am walking away.
I still see John, of course I fuck him now. It only took about four appointments and a huge blow up with a client with more realistic expectations for his £250 an hour to figure out what I was supposed to be doing, then I learned how to do it really well. I have spent a third of my life as a prostitute but I have a beautiful home with big diploma on the wall, happy kid, multiple vehicles in my garage, and the world an open possibility. I am a very lucky lady.
4. The business was booming in 2013
I drank a heap of wine before I went to the agency. This was about 2.5 years ago when the industry was booming. I did booking after booking and went home with a massive wad of cash. I didn’t think about it too much. I just loved the rush of being booked and making so much money. The industry is dead over here now and I have no idea why.
5. Not what she had envisioned
Just after high school, my girlfriend got a job as an escort. It was back when pagers were cool, for reference. I dropped her off at work on her first night. The place was in a strip mall, just a little spot that looked like a half-empty travel agency or insurance shop. It was out-calls only, so you basically wouldn’t know it was an escort service. I hung out in town, because she said she’d page me if she needed me to come get her.
She paged me pretty quick. I picked her up and we drove to a McDonalds and got coffee. She was a wreck. She said that she told them she was going on a break, but that she wanted me to take her home. She wasn’t even going back to get paid.
She went on an out-call, to a guy’s house. They had bouncer-like guys to drive the girls places, and so a guy drove her to some guy’s house and waited outside in the car. The customer obviously wanted to have sex, and she was totally blindsided by this. I honestly don’t think she knew that she was a sex worker. She thought she was going to be a “go out on the town for a date” kind of escort. She even wore one of her nicest dresses.
Long story short, she ended up just watching the guy masturbate before fleeing the place and getting driven back to the office. Then I picked her up and she never went back. The thing I remember most clearly was when she was describing it to me. She was disillusioned, incredulous. “There were pictures of his wife on the walls! Pictures of his family!”
6. He had a curved penis
My first time professionally was with an awkward Indian engineering student who paid me £500 to drive out to his apartment and do a two hour session with him.
Oh my gosh, I was so incredibly nervous the whole way, didn’t really know what I was doing, but once I got there, I pretty much went with the flow, chatted him up, started playing with him, and we had really epic conversation and he’s still responsible for one of my top ten orgasms (perfect little 4″ curved penis, hit my g spot with every thrust). Fucked twice, I gave him a blowjob while he was on the phone talking with people he was working with. I’m fairly certain he thoroughly enjoyed himself.
Immediately afterwards, on the drive back, I was just so utterly dumbfounded that I got paid that much to fuck a guy that was theoretically dating material if he had the time to date. It was tremendously encouraging, and I have those sorts of experiences with wonderful men (usually around thirty years my senior) sufficiently often that I’m not going to quit escorting until I age out.
7. Short on money
I started working because I’d gotten a few propositions through a dating website. I was studying med at the time and I was short on money. So one time, this guy made me what seemed like a lucrative offer and I agreed.
I didn’t know how any of it worked, so I told a friend I was going out and to call or text me in an hour’s time. We initially met in a park at night, sat in his very, very nice car, had a bit of a flirty chat, then made an appointment. He said he was 58 years old, but I think he was about 15-20 years older than that.
A week or two later, I drove over to his apartment. I was petrified, but I needed the money so I rang the doorbell. It was a lovely apartment, and he paid upfront. He was nice enough. He asked me to do some things that I didn’t want to do, so I said, “Maybe not this time.” Kept an eye on the time (via the helpful clock radio next to the bed) and thankfully he finished on time. Had a shower, bit of a chat afterwards, and then he kissed me goodbye on the cheek.
I think the fact that I said no to rimming annoyed him a little, but he texted later and asked if I would like to do a threesome with another working girl. Things proceeded from there.
8. Two clients on her first day
Yes I was nervous, but it wasn’t really awkward. I had two clients that day.
I can’t even explain the feeling of my heart in my throat on the way to my first job. I thought my heart was going to burst out of my chest. But it ended up very well.
The first guy was really nice. Mid 30’s, extremely average looking. It was somewhat… boring. 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. Along with the occasional gift of art or books.
And 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.
I still escort from time to time. It’s great money and a lot of the time, it’s just lonely older men. My agency is very safe, my clients don’t have my personal number (unless I give it to them) and they make me check in with them before I go in and again when I’m done.) Don’t get me wrong, I get some strange requests, but for the most part it’s just sex. I love sex, it hasn’t discouraged me in any way shape or form.
9. Was offered £900 for a night
This was only a few months ago. I haven’t made the best decisions in life. I was still 18 at the time and I moved out on my own. I started having a hard time making rent so I started posting ads and going on “dating” sites.
I got a lot of attention and started to talk to a lot of men but never actually went through any of it. That was until a month later or so and I got desperate and finally accepted an offer from one guy I had been talking to for a while. 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 over night which was probably another dumb thing to do but oh well.
I guess it ended up being better than I expected but maybe I was just luckier than some girls here that he wasn’t too creepy or gross. Since then I’ve only done this twice more but not with him.
10. Deepest and darkest fantasies
I was 35. I’m fit, tall, long brown hair and eyes that shift from blue to green, in good shape from bicycling. I have a Ph.D. in linguistics and a master’s in literature, and I’m male.
I was “in-between employment” and talking in a philosophy-oriented discussion forum on the Internet with some friends I had made there. I had discussed, at length, the importance of Jung’s notion of the Shadow in proto-Indo-European myth cycles, and was privately messaged by a woman who had not taken part in the discussion, but had followed it with interest.
She is a practicing Freudian psychoanalyst, in a large American city, and we discussed the tensions between Freud’s and Jung’s approaches, and the nature of the Shadow and integration. We began discussing sexual proclivities, then of course it turned to our own, we shared several compatibilities, 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 over the course of a month, had chatsex, swapped pictures, and so forth. 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” (in not such exact terms) and because of the rather intense nature of her fantasies – “buying a sex slave” was part of them. I finally agreed.
Two weeks of the utter legal limits of debauchery (aside from the fact of the exchange of money for companionship and services) 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 – until I was slavering and manic to ravish her, and only then she tugged open the knot securing me from acting on my impulses. Far darker things we did.
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. I had used the money to start a business, and gave her back every penny she had given me, and we agreed that we’d finally consider it an interest-free loan. Some of what I wrote for her and that we wrote together has since been published under a pen name, with a little commercial success.
She considers me her last hurrah – she went through menopause shortly after our last sexual visit together, and now doesn’t have the same sexual drive.
I have never involved money in a sexual relationship before or since, and honestly, none of the other relationships I’ve had compare in intensity or raw honesty with the experience we spent together. We stripped each other’s souls bare and bleeding, and know one another more intimately than anyone else knows us.