Things proceeded from there. I drank a heap of wine before I went to the agency. This was about 2. I did booking after booking and went home with a massive wad of cash. 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. I thought my heart was going to burst out of my chest. But it ended up very well. The first guy was really nice. 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. He paid me for an hour without question and I never saw him again.
I still escort from time to time. Fucked twice, I gave him a blowjob while he was on the phone talking with people he was working with. 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.
When I was 18 I was tight on cash and decided, fuck it. I need a sugar daddy. I went on craigslist and found a guy. He wanted to meet me first and needed a new girl to replace his old one, he was willing to pay 4 figures per date. I drove to meet him and was stuck in traffic on the way for an hour or two.
I sat at a Starbucks for a while waiting, he got lost because he was only there on a business trip. I was shaking by the time he came. We got burgers and drinks and sat at a table waiting for everything, talking. He was sweet but not my type, I was so nervous and shaking. We got to his hotel and sat and talked and ate, then started getting frisky.
He would not stop talking about how amazing I looked and was and I know he was trying to flatter me but after a while it got really old. I stayed the night and left in the morning. He gave me money for gas. Then I found this married guy. We talked, I sent him pictures of myself and he was hooked. I was an anal virgin and reaaallly hesitant about it. Drove an hour to a motel in his town to see him.
The way everyone looked at me, I knew they knew what I was there for. I knocked on the door, it opened. I stepped inside where the lights were off, kept my eyes to the ground. He came up to me and started stroking my arms, my face. He instructed me to put the blindfold on and I did. I hated every minute of it. I lost my anal virginity to him and it was painful and I cried. I could feel his fat slapping against my stomach, he kissed me with his bushy beard tickling my face and I fucking hated it, I wanted to vomit.
I cried all the way home. He was nuts about me, wanted to take me on trips and buy me an apartment in his town and all that. I agreed to meet him again, but no anal and no kissing. The second time he was coked out and had a hard time keeping it up. I had to awkwardly console him while he beat himself up over it, and suck his flaccid dick several times. Once he gave up on the whole thing and admitted defeat, I packed everything up and sat at the edge of the bed. He brought my money and placed it in my hands, and told me to look at him.
I was still wearing the blindfold and I shook my head. He took it off of me and told me to look at him. He was wearing a bandana that covered most of his face except his eyes.
He had lovely eyes, and it made me want to cry when I thought of his wife. I had a sick mind, I had a dirty side, and only he could fulfill it.
He messaged me a few times over the next year but I kept telling him no, no matter what price he gave me. 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.
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. The customer obviously wanted to have sex, and she was totally blindsided by this.
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. Pictures of his family! I remember the first time I accepted money for sex. A guy messaged me on a gay dating site. I knew I was down immediately. So I went to his place. As a 28 year old adult now, I think — what the fuck… that guy could have murdered me.
He could have raped me. He could have cut my skin off to wear it like a dress. I pulled out my dick, started jacking off, and once I was hard he sucked me to completion. Thank you very much. I never had to make them cum. They just wanted to make me cum. It was all about letting these guys fantasize that they had gotten me without paying for me. He wanted someone to cuddle with, rub against. We stayed in our underwear. A year before I had been approached by a friend of my sister who offered me a job as an escort.
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. 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.
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. 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. It was in a Travelodge classy! And I was super nervous. The guy was around 50 I was twenty at the time and he mainly wanted to make out and cuddle. The thing that weirded me out a little was he kept talking about how young I was and asked me for my real name several times I had a fake name for obvious reasons.
I was reluctant to give him my real name and instead just gave him another fake name — I told him my real name was Elizabeth but my friends called me Lizzie and he called me Lizzie for the remainder of the appointment — then had the cheek to try and haggle me down for an extra hour which I declined. 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.
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 liked him, so I kept going until he finished — maybe another 20 minutes? 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 all happened over Thanksgiving break my freshman year college. 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 know on his door and he looks mostly like his pics, just a little older and shorter than I was led to believe haha.
Its both of our first times so we have no idea what to do. We sit on the couch, talk 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. All-in-all, he was a super nice guy but ended up getting too attached: I have a Ph.
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. 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.
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. 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. This was only a few months ago. I was still 18 at the time and I moved out on my own. 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. 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 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. 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. 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 dollars on my desk. We did the same thing where we went to see a movie instead and went back to my place where instead of having sex he just wanted to cuddle me and talk about his job.
So I sat through 3 hours of him bitching about his life before he had to go and again I found dollars in my desk. I think he was a closeted guy that just wanted male contact and it was quite sad but just one of those things. I was very nervous my first time.
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