My personal sexual revolution had started a few months earlier when I decided to pop my cherry by visiting an escort. I’m not traditionally social, so it made sense at the time. I had had sex with three escorts so far, with the last one being a bit of a disaster.
Due to my humiliating experience with the caramel Nicky, I had sort of gone into sexual hiding. Of course, I still had my daily wank or two. Sometimes these included fantasies of getting to redo the Nicky experience. Most of the time it featured me venturing into new territory.
I recalled a time in my life when I had been discovering my sexuality. A friend and I had discovered masturbation together, through a series of events that are best told at another time, in another place. This led to a residual fascination with other people's penises.
What was interesting, to me at least, is that I wasn’t gay. I knew I wasn’t. I had briefly considered the possibility at one point, but I just knew that’s not who I was. And that was okay.
So why the fascination with other dicks? Maybe because homosexuality and heterosexuality are two terms we’ve learned to live with in society. Bisexual, transsexual. All these boxes. What if there was just “sexual”?
Maybe it was the taboo of it all that turned me on. Who isn’t turned on by taboo to some extent, after all?
So, I started some thorough “research” on the internet. I was interested in seeking cocks, but I had no interest in seeing them attached to men. This wasn’t exactly the time I discovered transsexuals or “shemales”, as porn and escort pages tend to call them. I knew they existed; when I had discovered porn, I came across the concept rather quickly.
My porn habits at this time started to include an exploratory venture into the “shemale” territory. At the time I was still involved in organised religion. I know; what a filthy hypocrite. Whatever. The point is, it was difficult to reconcile these turn-ons with what I was forcing myself to believe, what my church was shoving (unironically) down my throat.
The thing is, I never reached orgasm to the shemale porn. I would wank my heart out to it, turned on beyond reason, then I would pull up a good old-fashioned pussy pick, and I’d cum to that.
I went for two months without visiting another escort, all the while exploring this new aspect of my sexual interest. I used this time to build up the nerve to act on my curiosities. I started searching for transsexual escort listings. In those days, it was slightly harder to find these than it is nowadays. I had to look on a site that wasn’t my regular one, and the search was gruelling.
Many of the profiles were dodgy, unconvincing, or too masculine for my taste.
Soon, I found what I was looking for.
A profile under the alias of “Ginger” had the right level of femininity that I was looking for, with the promise of a hidden surprise. Now all that remained was timing and nerve. After I had found her profile, it took me about a week to build up the nerve to call Ginger. Probably because of my recent embarrassing experience.
I got the nerve one Sunday evening, pushed over the edge by a particularly horny mood.
“Hi, is this Ginger?” I asked when she eventually picked up the phone.
“Yes honey, that’s me,” came the sultry and husky response.
I quickly found out what I needed to know (address, price, services) and set off on a new adventure.
She was quite far from my usual stomping ground, so I trekked my way there in a mist of horniness and disbelief. I couldn’t believe what I was about to do.
When I finally arrived and knocked on the door, the sight that greeted me at the door made my stomach do a flip of anticipation. She was wearing heels and almost towered over me. Her build was slightly more masculine than I had anticipated, but she had the curves where they needed to count. She was wearing a black negligee with a red trim, and my imagination ran wild.
She was a brunette with strong, yet rounded features. Her face had a faint hint of her masculine origin, but she had dark eyes that were sultry and could draw you in without much effort. I speculated that she had some kind of Portuguese heritage.
She led me to her room, where we quickly made the customary exchange of pleasantries and fees. It was at this stage that my nerves took a hold of me and I felt compelled to remind her of something I had said on the phone.
“This is my first time doing something like this, I don’t really…” I trailed off into nothing, not knowing what I would have said.
“That’s okay, honey. I remember what you said. I’ll go easy on you. I’ll take care of you. Take off your clothes and lie on the bed, okay baby?”
Her reassurance helped a bit, and I got naked. I didn’t know what was in store for me, but I could feel the thrill building. My cock was semi-hard with anticipation. I lay down, on my stomach as she had instructed, and she got on the bed behind me.
“I’m going to start by giving you a massage to relax you, okay baby?” She said, doing something behind me I couldn’t see. She also touched my shoulder, holding something.
“Here, take this. It’s going to make the whole thing sexier,” she said, offering the object in her hand to my view.
It was a blindfold. What had I gotten myself into?
I took the blindfold and put it on. My semi twitched as she said, “Go on, lie flat. Let me take care of you.”
I felt her hands push me down so that I was lying flat on my stomach. She started massaging me and, I must admit, it was a decent massage. The whole time she made it was sensual as possible. Every escort massage until that point had had some sort of clinical attitude, but Ginger had her mouth right near my ear, reassuring me occasionally, whispering banal yet incredibly arousing things in my ear.
I felt something on my upper back and realised she had taken her negligee and bra off at some point. She was straddling my ass, so I could feel she still had her panties on. Her tits lightly brushed my back at times, and I knew I was in for a treat. The thrill was still there, and I was still nervous, but her hands and the occasional brush of a nipple did wonders to relax me.
It had the opposite result on my cock though. I started getting hard. It wasn’t instant like it usually was when I was in this kind of situation. It was more tentative. The recent trauma along with the nerves of the new situation meant that I was slowly building to a strong erection, rather than sprinting to a brittle one.
With my eyesight confiscated, I was forced to focus on the sensations going on elsewhere. The sounds, the smells, the warmth of Ginger giving me the massage, all turned me on immensely. She was exploring down my back, and eventually, she was rubbing my buttocks in circles. It felt great. As she was massaging, she was parting my ass cheeks further and further. I had never had that part of myself exposed before, and it was thrilling.
The effect was odd. I was incredibly aroused, but I was still only at half-mast. I felt her hands leave me, and she shifted her weight a bit and fiddled with something. Then she resumed her massage.
She spread her hands out to my hips and brought them to my inner thighs. She parted my legs and started massaging up toward my groin. Eventually, she touched my balls and lightly brushed and then squeezed them ever so slightly. She reached further up, forcing me to lift my ass, and grasped my shaft, getting me all the way hard. She started slowly jacking me this way, after having skilfully gotten me face-down, ass-up. I was presenting my rosebud to her, and it felt wonderful. She then reached over, took a pillow, and propped it under my hips.