If a boner could answer the phone, that's the voice it would use. Not bad at all. I said hello and for no good reason immediately followed this by saying I did not want to have sex.
Literally, she said hello and I said,"Hi. I don't want to have sex. I've probably made thousands of phone calls in my life, and I once told a pizza guy I loved him before I hung up, but this was pretty much the dumbest call in the fastest time in my lengthy phone career.
I heard something like a grunt on the other end and she said "OK. I explained to her that I wanted to spend time with her, but just like a date. I wanted to pay her to go out with me, have dinner, and chat. I should have started with that. She was very open to the idea and asked me where and when. Not once on the phone did she herself mention anything about sex or money, which I figured was a pretty professional way to handle things. You never know if I'm a completely moronic police officer, after all.
I tried my best to clarify what it would cost me, but she insisted that everything I needed to know was online, and if I was serious, I'd know what to do. Basically this meant me doing math. This was the first moment that doubt and trepidation set in. She put a value on sex, but now I had to put a value on funny. We settled on a time and a place and ended our conversation. I had just solicited a prostitute. My family would be proud, if they weren't worse people than me already.
Although Pretty Woman , a movie I didn't enjoy starring an actress I don't like that I haven't seen in a solid decade, was seriously my only reference point for how to behave and what to do, I didn't think a formal, tuxedo affair was the way to go with this, and not just because I don't own a tuxedo. I would have to wing things from here. Jasmine was going to meet me at a restaurant downtown at 7: I felt that was a good time for a late dinner that made me seem like an adult, plus, for the next few hours we spent together, it would stretch into what I figure is a sexy time of night.
As you may have noticed, I'm a complete idiot. I don't date a lot. The restaurant was fancy in that way that there are no crayons on the table and no one wears pieces of flair.
I showered twice before leaving my house, proving to myself that I have a weird kind of OCD about strangers and sex, and headed out. Arriving 35 minutes early, I proceeded to drink at the bar until Jasmine finally arrived.
As a man with some ability to make people laugh, in my day-to-day machinations I've dabbled in flirting with attractive women before; I've even had success. I don't want to brag, but I have touched a boob before, and it was just swell.
So I'm no rookie at this sort of thing. That said, Jasmine was like sex that something had arranged in the shape of a person and held together with a shimmery black dress and lipstick. If sensuality smelled like bacon, this girl would have been Jewish kryptonite. I was a little stunned. Also a little drunk. She said hello and gave me a kiss on the cheek as she took a seat next to me at the bar. Because I'm sly and shit, I literally leaned back a few inches to look at her ass.
It really was sweet. We made chitchat briefly as I tried to think of a cool way to bring up giving her a wad of cash I had in an envelope because she was a prostitute and I was a john. Luckily she was on top of that like stink on a monkey and had her tiny purse on the bar before I figured out what I wanted to say and suggested I just slide my donation inside.
I guess we work on the honor system. Jasmine had a very shrewd way of deflecting pretty much any question I asked her and turning it into a question about me instead. Over the course of dinner I learned that she loves what she does, she has been doing it a couple of years, and she would not show me her booty clapping skills in a restaurant, but something else could be arranged. Other than that, I didn't get very deep into her, so to speak.
Although she did admit to liking the movie Dude, Where's My Car? I once called Steve Jobs the da Vinci of our generation. Please don't support anything I do. I finished my steak and garlic mashed potatoes while she ate a vegetarian stir fry and we discussed our plans for the rest of the evening.
The only idea I had readily available that might kill two birds with one stone was dancing. Because I dance like a palsied child in the final throes of succumbing to a new disease on the frontier, I hadn't really wanted to do this, but of course I had few other ideas that didn't involve mini golf or going to a clinic the next morning, so dancing it was. Besides, I was about six drinks into the evening at this point and at the cusp of dancing by myself anyway.
So I went clubbing with a prostitute. If you've never spent an inebriated evening cutting a rug with a lady of the night, all I can say is that it does amazing things for your self-confidence. Jasmine had me convinced I was like the bastard child of Michael Jackson and Justin Timberlake, only possibly with a mightier dong and highly appealing earlobes, which she had a habit of biting while we danced. I knew this was all for show, but it was a show I had paid for, and a show I was putting on for a crowded room of sweaty strangers as well.
And you know what? I felt good about myself. It was all fake, and I didn't care. I had no sex with Jasmine that evening. When we parted ways, she kissed me on the lips and may have left her tongue somewhere in my chest cavity, after which I coolly said "awesome. That's not really my business anyway. I learned that she was paying for a Ph.
She'd actually been spying on me at the restaurant for a while before we met. She told me she sees no more than two guys a day, four days a week, and I was more fun than most of them. Also she took me into the women's washroom at the club and made her ass clap for me.
It was fucking amazing. I will probably never pay an escort to go dancing with me again, but only because it's kind of a costly way to spend an evening. It was fun, and Jasmine was a lot more fun to hang out with than I had assumed ahead of time.
And why did I assume it would be different? Hard to say -- it probably had something to do with whatever assumptions most people make about women who charge money for sex.
What did I learn? The only difference between an escort and, say, your sister is probably that an escort charges money. They're both regular people, though. 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.
Even though, at that point, I had had several hookups and play sessions with men I had met off craigslist or Fetlife, it was still weird transitioning to paid work and being afraid I was walking into a police sting. It was awkward at first, just because the guy seemed nervous too, but it went pretty smooth once we both relaxed a little.
My client was very happy, and ended up giving me an additional tip and leaving me a positive review on the site he had found me through, which helped to start my career out and get me more dates. I was a little surprised at that because I thought it went OK but was awkward. He was a bit older, and someone who was pretty recognizable in the community, which might have explained his nervousness. 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, then told me to get on my knees and get down to business. The first blowjob was pretty normal. After he came, he put his dick back in my face, so I assumed he wanted me to lick it back clean, so I did, 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.
He came a lot faster that time, pulled out and came on my face and I could feel it running down the side of my nose toward me eye. 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. Now, part of me wonders why I kept it up, because it really was odd now that I look back on it.
OTOH, it was easy money for doing something I was doing anyway. At 20, I was on AFF when I was offered 2, dollars 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 for being twenty, 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. I did escorting for three years before an ex ruined my reputation.
Sure, some guys were dicks, but I was making anywhere from for like twenty minutes of work. Now, I can talk to just about anyone without reservation.
My first day was easy because I started off as a dancer. I used to work bachelor type parties. The guys would ask for more. Eventually I just agreed to more. Almost always in a private residence. I would say like 90 percent of the parties the men were over So we would go and dance and hang out.