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.

This was when she gave me a slight warning.

“Just tell me if I need to stop, okay?”

“Okay,” I gasped.

What was next?

She parted my ass cheeks, and I suddenly felt something cold and hard on my virgin asshole. At first, it was a light touch, then she started pushing with growing pressure, but my rosebud was unyielding. I couldn’t relax, and I hadn’t really been prepared for this. I wasn’t there just yet. As the pressure built and gradually grew to pain, I needed it to end.

“Stop. Stop, please,” I said, almost out of breath without having exerted anything.

“Okay, baby. Don’t worry. We can take it slow,” she reassured me.

“Do you have anything smaller? I’ve never had anything in there, not even a finger,” I said to her, admitting how little experience I had in this particular arena.

“Unfortunately, I don’t baby. And I’m not going to use my fingers tonight, my nails are too long, okay?”

“Okay,” I conceded. I wasn’t disappointed. I hadn’t really planned or bargained on having my ass explored, it could wait.

She then continued to massage me some more, occasionally reaching under me to make sure my cock was still hard.

“Baby, I’m going to turn you over now, okay?”

“Okay,” I said, as she guided me around onto my back.

As she did this, I felt her get off the bed and get back on at my feet.

“What’s next is a surprise, but I need you to tell me if you’re close to coming at any point, okay? Promise me,” she insisted.

“I promise. I’ll tell you straight away,” I said.

“Good.”

Another thrill ran down my spine. What could be in store for me? She reached up from between my legs and started stroking my cock, making sure it was nice and hard. She did this for a while, pausing every now and then to make sure I wasn’t too close to cumming.

Eventually, her hands left me, and I felt her shift her weight up the bed. I felt her hand grasp my cock again, holding it straight up. Then a new sensation: sensual heat. I had no idea what was happening, but it was divine. The warmth slowly enveloped my cockhead and then my shaft. It travelled down until I felt myself balls deep in this new furnace of heavenly sensations.

She leaned forward and said, “Remember to tell me when you’re close, okay?”

I realised what was going on. Of course, I was in her ass. I was balls deep in a transsexual ass, and I was as hard as adamantium. The sensation was mind-numbing, and I just rode the wave of pleasure as she started to ride me slowly. First, she went up and down a couple of times, but then she started grinding back and forth on me, keeping my dick deep in her awesome anus.

I was slightly surprised that I didn’t feel her cock on my belly at all, or maybe I just missed it with my attention focused elsewhere.

She put her hands on my shoulders, rhythmically gyrating back and forth with her hips, maintaining depth. My cock was in heaven, and my hands found their way to her tits. They were enhanced by silicon, and not just hormones. I realised that this was obviously necessary, but quickly decided it wasn’t exactly my favourite thing.

That didn’t stop me from exploring her fun bags though. Her nipples were small and hard, a bit like mine, and her tit was a mixture of hard and soft. I could feel where her implants were.

As I explored with my fingers and hands, I felt the stirring of the eruption draw near. I didn’t want this to end. It had barely started. Yet again I was being betrayed by my own inexperience and over-excitement. I tried to hold back some more but realised that I couldn’t betray her trust.

“I– I’m close. I’m nearly there,” I said with a titanic effort of will.

She quickly stopped her grinding and got up off me. She then took my cock in her hand and started jacking me with a vengeance. With her determination to make me come and my proximity to the edge already, I was soon sending strings of cum up my own belly and almost into my own face. She kept wanking me expertly through the orgasm, eking every drop out of me.

My mind was blank, and I was semi-comatose. What the fuck had just happened. That was AMAZING.

I was quickly returning to earth, however. It wasn’t long before I had a cold drop of regret in my stomach, what I call post-orgasmic regret. What had I done? Who had I done it with? It hit me that she had just ridden me bareback. I didn’t know what to do or say. It had been amazing in the moment, but what the actual fuck?

As my mind swirled with these thoughts, I sat up and took the blindfold off. She had backed off a bit, but she was still naked, and she was rock hard. I hadn’t seen her cock until now, and it was smaller and thinner than mine. This probably shouldn’t have surprised me as much as it did.

“Do– Do you want me to help you out?” I said, ever the gentleman.

“Yes, please baby.”

“Okay,” I said. I was slightly grossed out, now that I wasn’t horny enough to do just about anything. I decided that I’d give her a handjob and avoid a blowjob that night.

She lay back as I reached for her cock. It was an amazing feeling, having another cock in my hand. It really was like touching a steel bar wrapped in velvet. She was very hard, and she had the lip-biting horny look everyone gets when another person is finally touching their genitals, promising relief.

I started exploring her little cock, grasping it lightly, and steadily jacking it. With my other hand, I cupped her balls very gently, rubbing them with my thumb with the utmost care. This wasn’t too bad, and it felt incredibly educational.

I started to employ the tricks I knew from having my own cock. This was far easier than trying to please the alien female anatomy of a genetic female. This was a tool I knew how to manipulate, and had been practising to perfection on my own for years.

I used my thumb to massage her frenulum as I pulled her foreskin back. I alternated this with a jacking motion every now and then, and very soon she started to pant and stiffen. I realised she was close and focused more intensely on her dickhead and frenulum.

Suddenly she spasmed and shot cum all over my hand. It wasn’t a powerful blast, and it must have been her second or third cum for the day. There wasn’t a lot, just enough to cover my hand and her mons a bit.

The smell struck me. There was something familiar in it, in the base scent. However, she clearly had her own brand of musk over the basic cum smell, and it started to get to me. So, I quickly reached for the wet wipes, and cleaned it off my hand. Leaving the tasting for another day, another experience.

We got dressed, and she showed me to my car. Just before I drove off, she leaned into my window and said, “Thanks for tonight. You were the perfect gentleman.” She blew a kiss and waved as I said goodbye and left.

I may not have been ready for everything that night, but it had been an amazing first step into a wider world. I wouldn’t revisit this particular type of adventure for several years, but I still cherish that night and the care shown to me by Ginger.