This story dates back about a year and a half. He saw my ad on an escorting website and wrote me an email:
Him: Hi. Your profile is intriguing and I’d love to see some face pics. All Best, *****
Me: Sure, they are attached!
Him: ****** — Do you have a hairy chest and legs? Could not tell precisely from the photo on the website. Your face pics are adorable and sweet. –*****
Me: Thanks! :) i do have hairy legs, and right now some lighter hair on my chest/stomach… i sometimes shave but it’s half grown back now!
Him: Don’t shave! Let it grow naturally. = )
Me: haha i definitely am now, don’t worry :) it’s not all back, but it’s def a good amount. i shave every once and a while to change things up, but i’m getting a little tired of it… which i guess is lucky for you! ;)
Him: yes, lucky for me. =)
do you think you would be available to meet today or tomorrow?
Me: I miiiiight be able to! I have a friend who may be coming into town tonight… or might not be haha… i think he won’t at this point. But how long/what time would you be looking for?
(I don’t exactly remember, but I think my “friend” just was an excuse in case I didn’t feel like working, or if I got a bad vibe from this guy. Clearly it ended up panning out!)
Him: Just left you a voice mail on your cell. Call me — maybe it will be easier to talk on the phone.
(We talked on the phone and he seemed very nice. As usual, it seemed like he had been drawn to my ad because of the focus on conversation and chilling as opposed to just sex. We decided to meet for an hour or two, and he sent me an email after we got off the phone.)
Him: Hi ******.
Confirming 3 pm on Wed. My address is ***********.
Subway directions: *************. As you head out of the station steps, and go through the turnstiles, you’ll see two sets of exits (one to your left and one to your right). Exit through the stairs on your RIGHT. I’ll meet you on the sidewalk.
Please be clean, ready for conversation, and be as sweet as you sounded on the phone. =)
Please confirm receipt of this e-mail.
PS: If, for any reason, you are delayed or need to cancel, please call me on my cell (***-***-****).
I ended up running late because of the trains. When I finally got there, he was standing in the rain. He was a plump man that I guessed to be in his early thirties, and he was holding a giant umbrella, the kind that annoys me on crowded sidewalks (unless it’s covering a family of four) but that he probably got away with in his less crowded neighborhood. He told me that he had almost given up on me and gone home, and I’m supremely thankful he didn’t because it turned out to be a very profitable night.
We started the walk back to his apartment, and I noted how nice his neighborhood was. Very cute and brownstoney. I could tell right away that he was smart, and seemed warm. Maybe a little formal? Or maybe that was my impression by the end of the night.
We reached his apartment building (surprise, a brownstone) and climbed the stairs up to his floor. The inside of his one bedroom was cute, although a little crowded. Boxes here and there, but a nice space. Living room, bedroom, kitchen, bathroom, and probably a couple closets. My shoes were already off, as his apartment had a no shoe policy, but he asked me if I wanted to take off my pants, and soon I was sitting next to him in my shirt and underwear. He put his hand on my leg, felt my leg hair and smiled, casually mentioning again that he loved body hair. Too bad I had trimmed my chest and stomach hair a bit already. I don’t want him to seem at all lecherous, feeling my leg hair while we sat and chatted, because he really seemed sweet. He was very into theatre, so that opened our conversation, and we soon realized we probably had some mutual friends. It was even possible that we would run into each other at some point. I really wasn’t worried about it, though. He seemed very nice and discreet, and clearly wouldn’t want anyone to know about our arrangement for the same reasons I wouldn’t. Even if we ran into each other at some point, it would be totally plausible that we had met at some friend of a friend’s party.
After 30 or so minutes of conversation, we started kissing some and moved to the bedroom. As his clothes came off, I realized that he really was about as all around unattractive as I would have guessed. He was chubby (or maybe just fat), and his dick was small, his public hair wiry, unkempt, and longer than I would have guessed for someone who was generally smooth on other parts of his body. We made out, although his kisses were very soft, in a tentative way. Almost just pecks at times. Every time I went down on him, he pulled me off pretty quickly. I think he didn’t have very much endurance.
The strange thing about the whole hook up was that he kept on asking me if I was ok. We would make out, and he would pull away and ask me if I was ok. I would always smile and say yes, absolutely. But I think what was really happening was that he wasn’t sure if he was ok. Or, maybe he wasn’t sure how he was doing, and his defense mechanism kicked in every time he doubted himself. Which was every time we did anything sexual. Which happens a lot during sex. Although, he definitely was seeming to veer away from anything anal, at this point.
Side note: With some overweight clients, I can’t always tell what they want in terms of attention paid to their upper bodies. If I’m hooking up with a hot guy, I’ll touch his abs/chest, lick him, etc… general hot hook up stuff, nothing crazy. But with an overweight client who may be self conscious about his body, I at times feel like I’m drawing attention to and/or emphasizing his flaws if I do those things. But I also don’t want to IGNORE it and have them be self conscious in that respect. I also don’t want to deprive them of a hotter experience, if they’re into that. For the most part, clients are easy to read sexually. But with this man, he was so tentative that it was hard to tell what he wanted… I got the impression that he didn’t want me to pay attention to his upper body, but also that he wasn’t confident enough to let me know what he wanted. I’m still not 100% sure how he feels.
He suggested we move to the shower after 10 or 15 minutes, and we continued with the touching/kissing. He ended up blowing me until I came in his mouth, and he spit it out. “That’s the best thing about doing it in the shower,” he said. “No extra cleanup!” I realized as he said this that I think he’s a little OCD. I apologize to any true OCD sufferers out there, but he was very strange about touching/kissing/blowing during the whole hook-up. At the time I wrote this off as inexperience… but I think he actually found it all very hot, while at the same time, not wanting to get “dirty.” He seemed like a very particular person.
We finished our shower, and we headed back out into the living room, where he proceeded to show me his extensive stuffed animal collection. I shouldn’t call them stuffed animals, they were actually all very artfully crafted, expensive collectibles – literally thousands of dollars worth – but yeah, they were stuffed animals. Some were on shelves, some still in boxes stacked against the wall, all around the room. He had a story for each one, and had even gone to conventions to sell and trade. It was kind of endearing, really. It really brought him joy!
At this point, he asked me how much it would be to spend the night. I told him my rate was 1000, which made him hesitate, so I offered 800 (which is a rate I’ve accepted before. I don’t like negotiating, but it’s a little better if I aim high and still end up with a solid number. Without a steady stream of income, sometimes I have to bend my rules, as much as I would warn against it to other escorts). He felt bad, though, and didn’t want me to have to lower my prices. I insisted it was fine, but he offered 900 to ease his conscience. So my little afternoon turned into a sleepover!
This is where the night took somewhat of a turn. This requires a little back story, but I’ll be brief. Months before this meeting, I had met a guy at a bar from Mexico who was on a business trip. We hung out and slept together the couple days that he was here, and then kept in contact in the following months. He ended up flying from Mexico to visit me for a couple days over the summer, and one night while we were drunk, we had unprotected sex. Now, I’m writing this over a year after the fact… I honestly don’t remember the exact details or order that everything happened. However, the facts that I know are these: I had an std, gonorrhea. I don’t make a habit out of having unprotected sex, but I believe I got it from someone I trusted at the time. I gave it to the guy who was visiting me before I realized I had it, and soon after had some symptoms, took antibiotics, but had my initial tests come back negative, so I assumed I actually didn’t have it at any point. I was not seeing clients while I was unsure of my std status. However, my Mexican visitor’s discovery of the fact he had gotten it, and our initial discussions about it, started this night while I was with my client. Hope that makes enough sense. But again, I know that on this night I had taken antibiotics and it was gone. It’s kind of embarrassing to write about, but it happened, and it’s done. And of course, I’m so thankful it wasn’t something client related, and it wasn’t anything worse.
So, we decided to go to dinner, and as we were walking to the nearby restaurant, I got a voice mail from my Mexican man that said he really needed to talk. But I really didn’t want to be rude while I was being paid for my time, so I had to sit through dinner, knowing that I had personal matters that really had to be taken care of. Also, keep in mind, this guy that had visited me was someone I really cared about. I was planning on visiting him in Mexico in the coming months, and was even considering taking Spanish lessons for the trip. It was really eating at me that I couldn’t talk to him on the phone at that moment, and I think he was feeling the same way, as he kept calling me throughout the meal. It was a struggle, but I managed, making conversation and forcing myself to eat the excellent food that my client was buying for me. Apparently I did a good job, because he clearly enjoyed himself. As we walked back, though, I knew I had to call this guy. It was going to be less rude than how distracted I was going to be with my client if I didn’t call. When we reached the apartment, I told him my friend had been calling me all night and asked if it would be alright if I chilled outside for a second and returned his call. Thankfully, he was totally ok with it.
I found out that my Mexican man had been diagnosed, although not fully tested yet, with what looked like Chlamydia. I truly felt awful, but ironically, the first thing he said to me in his good (but occasionally broken) English was “Are you still my friend?” He was just as worried as I was about the others reaction to the news and the stigma that stds carry, even if I was a part of it. After about 10 minutes of discussion, my client called from inside his apartment to make sure I was ok, and after switching back I wrapped things up. By the end, it was clear we were more worried about being on good terms with each other than the std itself (which sucked, but could be dealt with), and I was able to refocus my night on my client.
I went back in, and apologized for taking so long. He just wanted to make sure I was ok, and asked what was wrong. Clearly I wasn’t about to tell a client about my std troubles, so I avoided the topic by saying it was discussion about money owed by a friend (that had to be discussed tonight, for whatever reason), and left it at that. He was very concerned and sweet. We moved on to listening to some various musicals from his excellent CD collection (New York Philharmonic recording of Sweeney Todd, highly recommended). Then he realized he had to leave some feedback for a hotel that he had stayed at during a recent visit to Vegas. This is when I realized the extent of his semi-OCD qualities (again I use that term loosely).
Apparently the lobby of this hotel was disorganized, and part of my client’s NYC job (to be very general) was about organizing groups of people. He proceeded to spend about an hour drafting an email to this hotel, telling them about their poor customer service, and how (very specifically) they could improve the flow of their hotel lobby. While a little bizarre (I would usually assume this kind of behavior is reserved for older, senile people with nothing to do), I have to admire how well thought out his arguments were. I’d never been to this hotel, but I’m sure he was right!
At this point it was getting late and it was time for bed. Nothing else sexual happened, which is always interesting to me, as I think of the high price of escorting as directly relating to the sex. Also interesting, he didn’t need me to sleep in the bed. He insisted I take the couch in the living room, because he snores. Double score!
The next morning, I left relatively early, as I had some place to be (or maybe just said I did, don’t really remember). He didn’t have all the money, but gave me the first half before he got more from the atm. He said he “hated this part” while he counted the money. We really had connected over the course of the night, and I think he didn’t like the feeling that it was in exchange for money. Or, maybe he just didn’t like the fact that he was hiring a prostitute. But again, it made him sweet. He implored me to be careful, and I assured him that I didn’t do this often. He still gave me his worried face though. He was very much a mama bear. A particular, worrying mama bear. After he walked me to the atm and gave me the rest of the 900, we parted ways.
The story of this client has a much more recent part 2, which will be titled “the 40-year-old virgin”. I’m torn between writing that and writing part 1 of my coke head client saga. Look for one or both in the coming weeks.
Thanks for reading!