Chapter 29

Uncle Hitesh, or Uncle H as I call him, is a bit of an anomaly, a contradiction in our family. He is both the golden boy and the black sheep.

He is very rich, certainly a millionaire, and probably several times over. He made his immense fortune, buying, renovating and selling property. He is one of my dad’s younger brothers. Uncle H looks a little like me, or rather I look a bit like him. He is tall, slim and handsome. An outsider might mistake him for my father rather than my real dad. But that’s very unlikely. Which leads me to the black sheep part.

Uncle Hitesh is gay. It’s never actually been said in those words, but the whole family have given me that impression by hints and innuendo. Like I said, homosexuality is not such the terrible sin as it is in other religions, but it’s not openly discussed either.

If there is such a thing as a gay gene, it seems to have dodged my dad and ended up in me. Of course, I don’t actually believe in that theory.

Uncle H as well as being rich, is also very generous with his wealth. He has helped my dad out, and his other siblings, many times financially.

As I approach my seventeenth birthday, driving lessons and a small car for me, have been mentioned.

My birthday is a month away and Uncle H has said that he’ll buy me a car if I pass my test. A new car, not a second-hand one! All very generous and typical of him.

My dad wasn’t keen at first, but relented eventually. Uncle H is very persuasive, which is why he is so successful.

Uncle H wanted me to pop round to see him. My dad wasn’t keen on that either.

So dad had one of his little chats that he’s had with me over the years. Basically, it was that I should remember how friendly Uncle Hitesh is, so don’t let him get too friendly.

I felt so sorry for my dad, he looked so awkward, talking about his beloved little brother as if he had a disease.

But I reassured my dad that I knew all about the rumours and that I was quite capable of looking after myself. My dad actually ruffled my hair.

I texted Uncle H that I would pop round Saturday evening after my shift at the supermarket. I didn’t really need the Saturday job anymore, now that I was raking it in with my sideline business. But it was an effective cover for my income.

The downside of the job, was of course, Vernon. I would have to curtail our little liaisons. I’d spin him a yarn that I was trying to go straight and that I didn’t do that sort of thing anymore, that should keep him at arms length.

But first on my happily busy agenda, was Jennifer. The assignation was set for tomorrow evening, so there’d have to be another fictional visit to Jamie for a game-playing session, just for mum’s peace of mind of course.

The more I thought about the appointment with Jennifer, the more I became intrigued and curious.

Having sex with men was my forte, my raison d’être. But sex with a man who thought of himself as a woman; that was entirely new territory. A situation that I was now feeling rather keen to explore.

The next day at college went without any drama, and disappointingly, no sexual encounters of any kind. Although, my almost constant level of arousal, surrounded as I was by fit young men, required a visit to the toilets for a quick wank to take the edge off.

But even so, by the time evening arrived, I was as horny as hell, and keen to get it on with Jennifer.

I made my excuses with my parents, another evening playing those awfully violent computer games with my nerdy friend Jamie.

I had my Uber arrive down the street at the usual spot and I was soon on my way to Jennifer’s address.

Once in the cab, I found myself wrestling with a conundrum that had first puzzled me when I encountered the very butch lesbians at the gay club. How similar to a man would a woman have to be before I could perform? Conversely, how similar to a woman would a man need to be before I couldn’t? I guessed I would be getting some idea very soon, once I met with Jennifer.

The cab eventually pulled up outside the address I had been given. I dropped the driver a few quid tip, I was flush now, after all. I could afford to be generous.

I knocked on the door of Jennifer’s ground floor flat. After several moments the door opened and there stood a woman. Or rather, a man dressed as a woman. Very few cross-dressers, in my experience, which I admit was limited, were totally convincing. Jennifer was no exception. The height was the immediate give away. Jennifer was as tall as me. The long dark hair, looked natural, but still, somehow not quite right. Next was her facial features. No way was that a woman’s face, in spite of the make-up. And the hands, always a sign. Jennifer’s hands were way too big to be feminine. Countering the masculinity was the bust. Jeremy, it seems, when he was a Jeremy, had gone all out in the boobs department. A tight-fitting long sleeve top displayed an impressive bosom.