Confessions of a Teen Gay Escort Ch. 06

Up to now, I've mostly been telling you about the encounters I, personally, found the hottest or the most memorable. However, because I'm a submissive bottom with a thing for older guys, I realize that the memories I find hot may be a little samey for readers, so for that, I apologize. So, I thought I'd start off this time telling you about a few different sorts of encounters.

For example, I once got invited by a straight couple to join them for a night. They were a lovely pair in their early thirties, both attractive and in good shape. The guy apparently wanted to know what it was like to suck dick, so I was more than willing to oblige him. He wasn't bad for a first timer, though both me and his girlfriend had to give him some tips. He wanted to put my full (flaccid) member in his mouth immediately, but I instructed him to live around the cock head to warm it up first. Men are always so anxious to 'get down to it', we often forget how nice it is to play and tease and build up tension. Women are much better at that.

Anyway, the guy got me hard and then got to blowing with some excellent rookie enthusiasm. He accidentally scraped me with his teeth, which hurt like hell and he wouldn't stop apologising for, but for the rest it was pretty good. I asked if he wanted me to cum on his face, but he said he didn't want that so I told him he better stop.

This couple got off on cuckolding, too, so they asked if I wanted to fuck the girl. I had literally never been with a girl before, so I thought what the hell? We made out a little, the girl showed me how she liked to be fingered and then I penetrated my first pussy. It was actually really enjoyable, surprisingly. She was a lot softer and shapelier than the men I sleep with (who are attractive in other ways, of course). In fact, I enjoyed it so much that I've tried it a few more times since. I guess I'm now officially bisexual, which is a pretty weird thing to wrap your head around. You don't often hear about people discovering they're bi if they're already firmly in the gay camp. But, I like to try it every once in a while. Also, picking up girls is too easy if you're not (hugely) attracted to them.

But back to the gay stuff. There are a few reasons why a man might hire a rent boy. For most of them, it's to find an attractive mate without having to scour countless bars with the chance of ending up with nothing. Others-and this is also a big group-are married but bicurious. They want to experiment with their sexuality, and hiring a professional allows them to do that while minimizing certain risks (catching diseases, having lovestruck boyfriends calling your wife, getting arrested in public bathrooms scouting for sex etc.).

There is, however, a third group, and it contains both my best and worst clients. This is the group that likes to hire an escort to indulge in the weird and wonderful sexual fetishes that they can't find a 'normal' partner for. You'd be surprised how many different sorts of things get people's freak on, and if I didn't cater to that market I'd be losing a lot of business. So, although I do keep some things off limits (nothing involving poop, ever), I do try to accommodate these men wherever possible.

There are quite a few foot fetishists out there, who mostly just want to caress and lick my feet. I don't really see the point, but I keep my feet clean and my nails well trimmed for them anyway. Then, there's a lot more piss fetishists out there than you would think. Piss sex is one thing I'll only do 'actively'-I won't get pissed on but I will piss on clients if they ask (and pay extra). BDSM and bondage are fetishes I can enjoy in both roles, although I don't do extreme stuff. Fisting is something I tried once but won't be doing again in a hurry.

However, I have to say my favorite fetish is crossdressing. Not only is the money fantastic, it lets you explore a whole different side to your own sexuality. I got into doing drag for the first time about a year ago. Louis rang me up, saying he had a wealthy Arab business man, who had called on him before asking for a crossdressing escort. However, the boy Louis had sent last time - who I believe was a professional drag artist - no longer worked for him, and he had to search for a replacement. He told me I was the most feminine of the boys he managed, and that the money would be amazing but that I'd have to really commit to it. I agreed almost straight away, it sounded like fun.

Well, it turned out to be fun but it wasn't easy. We had a week before our Middle Eastern John came to visit, so Louis and I had to get to work quickly. He came over to my place carrying a weekend bag crammed full of crossdressing gear. First up was shaving. We went into the bathroom, where we took a Ladyshave to the little amount of body hair I do have. I did my armpits and then legs myself, proudly finishing the job with only a few cuts. I also did most of my pubic area, but we agreed that we couldn't get 'everything' down there and Louis finally convinced me to book a salon appointment for a male bikini wax.

Next up was make-up. We spent hours in front of the mirror, trying out foundations, mascara, eye shadow and lipstick until we got the sultry, smokey effect we were after. I have to say, I girl up pretty well if I say so myself. Now came the wig. Fortunately, Louis hadn't skimped on this area and had bought a really nice, jet-black piece which fit snugly and looked great.

Then came lingerie. Louis had picked out a really nice red and black basque and panties combo, which just about fit. He had also picked up some 'fake tits' from a sex store, which clinged to my chest with a mild adhesive. A thigh-length black dress and red and black stiletto heels completed the outfit. Walking on heels was a pain at first (they put a huge amount of pressure on your little toes), but the end result was way better than expected. I could pass for an attractive woman from about twenty meters away, and a hot tranny for any (gay) man closer than that. My bubble butt, accented by the heels, and slim figure made me a decent 'canvas' and Louis' handiwork with make-up and women's clothes did the rest.

My new look immediately made me horny. So horny, in fact, that I tried to seduce my boss. I had thought, after being asked to suck him at my 'interview' that sex with Louis would be a regular thing, to keep him happy or whatever. However, nothing had happened since, which I'd found slightly disappointing as he's a very suave, attractive guy. This was my chance, I thought.

It was no sale, unfortunately. Louis said he was tempted but that he didn't sleep with his 'boys' as a rule. So, I waited for him to leave, grabbed my vibrator and got down to it myself. I tried to practice making girly-sounding moans, and I took lots of pictures for feature use.

The next day, I got my Brazillian wax. Well, the less said about that, the better but I did end up nice and up nice and bald down there. I also picked out a nice colour nail polish to match my lipstick.

Now, it was just a matter of time before the big date...

Sorry, I'm going to have to leave you hanging there. Full story of my drag date soon!