As I’ve said before, I had two “first times” escorting… the first one was the first time I was paid for companionship/sex. But it wasn’t reallllly what I was setting out to do as an escort… meaning it was an hour or so of oral sex, and not much else. I guess it didn’t quite “represent” me as an escort? I didn’t give the guy what I think of myself as offering in this business… and it wasn’t the experience that cemented my decision to make this my day job.
For you new readers who are thinking, “um wtf are you offering besides sex?” I’ll revisit my business plan. I really do think of myself as a companion… someone to talk to, chill with, and yes, sleep with, but it’s more of a complete date. I don’t want to be jumping around to multiple one hour appointments every day (or even every couple days). By spending evenings with one guy (or sleeping over) I can get more money at one time, and in theory develop a longer lasting relationship with each client. Also, I’m pretty sure it’s way less soul sucking this way, although I have no way of confirming that.
That fateful night, I put an ad up on craigslist. As my ads still do, it stated pretty specifically that I was looking for something longer or overnight. I advertised my college education and interest in meeting new people over some wine… no mention of sex (although i’m pretty sure it was understood by everyone who responded). My guy responded with this email:
him: “hey there, not sure if you are still looking or not, but 36y/o, professional (suit & tie type), masc, non-smoker, ddf, top here who lives here for now and moving to europe soon (although will be back regularly). Looking for good company, friend with benefits, etc. If more develops, would be cool with that as well. Have face pics to trade.
Let me know if interested in learning more. I do have face pics to trade.”
Interesting to me when guys offer to trade pics. I guess they are pretending that it’s just a regular hookup? Or maybe they just want to make extra sure that I know what I’m getting into and won’t reject their money because they are too ugly or something.
His pics were pretty average. Couple emails later:
him: “Was thinking of relaxed evening after run (probably not starting till around 10:30) of wine, movies, kissing, cuddling and as mentioned before sexually am top. Let me know if you are still looking for tonight. I had previous plans, but to be honest, not sure that I want to go through with them (was just heading out to drink with a friend).”
we settled on $800 to spend the night.
him: “ok, about to leave for run (little bit late). Let’s plan on meeting at my place at 10:45 (will try to be showered, etc. by time you get here but may be cutting it close as plan on doing long run). I have no food here (travel a lot) so bring any pretzels or chips, etc. you may want to munch on while having wine.”
I showered, put on my sunday best, double checked my little escort bag that I always carry (but was then carrying for the first time) and set out, very nervous.
When I reached his apartment and he answered the door in his pjs, I quickly realized he had gained some weight since the pictures he had sent me were taken. I walked into his very cute one bedroom, which overlooked the hudson river. Of course, when I called my friend to tell him that I had reached the apartment safely and hadn’t been clubbed and taken advantage of, my phone failed me (damn you at&t). There was an awkward 5 minute silence between me and this guy while I tried to reach my friend, worried my night of companionship would turn into a group thing with New York’s finest. Finally I gave up and texted him (which worked, thank god), but the night already felt like it was off to an awkward start. He let me choose between white and red (I chose red) and poured us some wine.
Rent Boy Tip: Be careful of roofies and other drugs! Always remember: “Watch your glass, save your ass. Don’t see him pour, get raped on the floor.”
I leaned over his counter while we made small talk. He started telling me about his work, which involved buying and selling companies I believe? I don’t quite remember now, but besides the fact that it was totally boring, it was so filled with jargon that I could barely understand what he was talking about. Of course I smiled and nodded and urged him to tell me more, which he happily did as we headed over to his couch where “Shrek” was playing silently on his flat screen. He continued on, and I have to say I kept up pretty well considering I knew nothing about his business. Now, there are plenty of times when I would be completely honest about what I know and don’t know. Clearly I’m not expected to know everything about a random business. However, when someone is talking to me as if he EXPECTS me to know things, there is a little more pressure. I don’t want to seem stupid, especially when I’m being paid to be good company.
Rent Boy Tip: Act like you understand everything, and then pick out the couple things you DO understand and expound. It will seeeeeem like you are keeping up… at least it did that night! Always remember: “Smile and nod, be spared the rod. Stare and blink, get raped by the sink.”
The conversation was fine. As the topics changed, it became more interesting… hearing about another person’s life always has some value. He was quite the world traveler, and was soon moving to europe (not the first time he had lived there. I forget what country… switzerland or something?). He had some beautiful paintings. Every time he visited or lived in a country, he bought a painting as a souvenir. Isn’t that a cool way to remember a trip? Instead of crappy little knick knacks.
After maybe 45 minutes of talk, we started getting a little more intimate, and I was soon in the middle of my (second) first sexual experience with a client. We made out some, I felt him up, and he boasted about his big dick. It was fairly big, although not gigantic… certainly above average. After going down on him while he sat on the couch, we moved into the bedroom where we moved on to more “intrusive” activities… soon I was being fucked. Now I consider myself versatile (does anyone reading not know what that means? it means i’m a very generous person) although I do end up bottoming more than topping. He was fairly large, though, so we had to take it slow at first. I have to say, I took it like a champ. He fucked me until he came (I’m almost positive that I didn’t cum, although maybe I’m not remembering… he really didn’t focus at all on getting me off) and then we headed to the bathroom to clean up.
Throughout all my experiences, I’ve been amazed at how turned on I can get by guys that I’m not attracted to. It wasn’t mindblowing, but really, getting fucked is hot. Sex is hot. And unless i’m DISGUSTED by a person or by something they expect me to do, so far i’ve been able to be sufficiently turned on and get off.
We showered together and chatted (he said “I should be paying him” for his big dick… ha) and then moved back out to the couch. He showed me pictures of his trips in europe (man i got so bored at this point, not gonna lie) and eventually 1 or 2 am rolled around, and he asked me if I still wanted to stay the night. This seemed like a trick question to me, and it was almost a little awkward. I didn’t want to stay the night IF he was going to pay me all that money and I could just leave… really I only wanted to stay if HE wanted me to stay. But I think he wanted me to want to stay of my own volition… so instead of risking anything I said yes, of course, and we went to sleep.
I remember waking up early and lying there… again bored. Waking before the guy (which i always do) can be complete agony… I can’t get up before them, I don’t want to be rude and wake them up, but I can’t stand just lying there with NOTHING to do.
Eventually he woke and we cuddled and chatted… and soon he was hard again and fucked me for a second time. Again, it was a liiiiiittle rough because of his size, and he didn’t get me off (not expected, of course), but it was fine. We dressed, and wandered out to his little balcony, where he pointed out various landmarks in the buildings around us. There were a couple TV studios. I made my one blunder while we chilled out there when I started talking about my distaste for Elisabeth Hasselbeck, the one super conservative (and super stupid voice) on The View. The minute I uttered the words “annoying” and “republican” in the same sentence, he said “careful… my father is [some republican chairman blah blah blah].” I had to quickly backtrack and say that I meant she was annoying because of her stupidity, not because of being republican… which is mostly true, really. He did a little obama bashing and then the subject changed. I have always kept that lesson with me, though; I’m dealing with people who run in very different circles than me. Clearly some are bound to have different political views!
I had realized by then that he was kind of egotistical… just a little wisp of “toolbag” in his aura. Clearly thought very highly of himself and his success. He mentioned at one point that he didn’t feel like he needed to hire guys. It was just easier than trying to meet one, not to mention the many expectations and complications. He had the money, so why not just hire a cool guy for a night? I liked the thought, but I was left thinking “please… you are paying because this includes sex with someone you wouldn’t be able to fuck otherwise.” Seriously, I’m not judging it, but that IS kind of the point… he was chubby and unattractive. I’m sure he did want friendship and conversation for the night, which he could have found for free… but i don’t think he could have found the sex with someone my age. Maybe that was just a little bonus in terms of what he was looking for? But again, he struck me as full of himself… and in this respect, fooling himself.
Soon I was tying my shoes, and as I finished he handed me my wad (that’s right): $800 in twenty dollar bills. I shoved them into my escort man purse, gave him a goodbye peck and headed out.
I’m sure some escorts feel dirty after all the deeds are done. Maybe they feel like their payment is tainted by their dirty sinful acts… just a big, paper wad of sin. I, however, got such a rush, especially that first time. I mean, I was paid $800 for literally maybe 30 or 40 minutes of sex. Maybe it was even just 20 or 30. The rest of the time was chatting, wine, and relaxation. At worst, a little boredom. ‘Meeting new people,’ just like my ad said. I was (and still am) thrilled to be getting paid so much money (in tax free cash) to do something so EASY. That second first time was what really sealed the deal… until I had a job that i loved, or a relationship that forbade me from it, or i was hired by a rapist who cut off my dick, i was (and am) going to be an escort.
-B
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