10/01/2018 Cheryle Whitcomb   0Comment

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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. When I first went along it was because my cousin got sick and she asked me to go with her friend. She explained I would have to just go, flirt, sit on a few laps. I could dress as sexy as I wanted. So I did that.

I wore shorts and a tank top. I turned out to have fun. I ended up topless and basically got paid to sit around, joke and flirt with a bunch of men. I really love attention so worked out well. After that they used me as a substitute more often or if the group was larger.

I got a bit more crazy with my outfits. People were laughing, drinking. Passed around joints etc. I sat on a ton of laps and basically would feel boners. I would laugh and joke. Men treat you differently. The same man who would be embarrassed if you caught him looking at your tits at the super market had no problems looking when you are there to party.

After a few months of doing this I felt like the next step was no biggie. I would get like for just hanging out but the girl who went with the bachelor for more. When I would go to parties the other girl would just tell the guys right away that she would be the girl for the bachelor. After I felt ready, we gave the option. My cousin was curvier with booty and boobs. Her friend is curvy too but Asian. The first time I got picked I pretty much just gave him a naked lap dance and stuff progressed.

Afterwards I felt super sexy and empowered. I would do like 1 or 2 parties a month. Who ever got picked would go in the bedroom. The other girl would just hang out and flirt. We would also give out info for 1 on 1 meetings.

I never had to use websites or walk the street. That lead to more traditional meetings. I never had any creeps. Every guy I met was a guy I had laughed and joked with before so made it easier. We all normally played safe but I let a few regulars do different stuff. I am a sexual person so I tended to have fun. Many of the men I met with 1-on-1 were married over The only down side for me was making an appointment a few days in advance and just not being into it the night of the meeting.

Since many were married they would plan a night when their wife was busy or whatever. I did like 1 or 2 parties a month and met guys for 1 on 1 meetings a month. I made around an extra a month. We dated a while and I got serious. After I quit I still met a few of my regulars for a bit. I love my bf and my current life but occasionally I still miss the old life. My bf treats me well. But not the same as the other men looked at me. I was extremely nervous but I had an experienced girl showing me the ropes.

We had posted single ads and duo ads and my first call was asking for a duo, which made me feel a lot more comfortable with he whole situation.

So I get all dressed and am about to pee myself waiting for this guy to knock on the door. He was a pretty good-looking 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. I felt pretty gross, he got dressed and left and I made a quick bucks. That call definitely broke me in for the rest of the calls that day as they were all normal. I have seen the guy a few times since then. This is from the other end of things. I do it for one very specific reason: Petty, I know, but sweetly satisfying nevertheless.

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