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External Link/Members OnlyExternal Link/Members OnlyThis was a two-hour booking for £200 (half the price of a hot young TS in London) but, more importantly, it was a walk down memory lane. Tiffany was the second TS escort I ever saw, which was in East London some time in the mid-1990s. She was the first I tried (and failed) to be topped by. Her cock was just too fat for my virgin asshole. Her cock is still fat but my hole has now had years of practice.
Having spotted that she was back in action a year or so back, I took advantage of a rare trip to the south coast to renew our acquaintance after a quarter of a century. The arrangements were made efficiently and easily with one phone call and a couple of texts. I'd been a little suspicious that she looked no different in her profile pics from the way she looked back then and wondered how old they were, but she looks like that in person too. She sure as hell must be older than 45, but apart from a slightly plumper middle, which wasn't evident until she undressed, she's barely aged.
Of course she didn't know me from Adam until I said we'd met before. Back then I had brown hair on my head. Now I have grey-white hair on my chin and my own plumpness issue.
I'm not going to be very specific about where she lives because it's in a small community and one crucial detail will pinpoint it for sure. But she needed to come to the roadside in the pouring rain in coat and umbrella to flag me down at the tricky-to-find location.
Once inside her small but tidy premises, she hung up her coat (along with mine) to reveal the old-fashioned floral flock she's wearing in one of her AW pictures. Very fetching. Her voice is posh and, although camp, it's feminine too. You'd never know she was trans on the phone.
We had a longer than usual chat due to the catch-up factor. I'd seen Tiffany twice, possibly three times, way back when. On one memorable visit it was a threesome with her best friend Jane, also a trans escort, who has since died. That session was my first experience of being spit-roasted (Jane's cock was easier to take up the tailpipe).
Tiffany does that cheeky thing of randomly touching your cock and balls even before you get undressed (always a sign of a good time to come) and before long we were semi-naked and wrapped around each other while still standing up.
There was a lot of action but with so much time booked the pace was quite leisurely. It included deep, deep French kissing, constant cock fondling and sucking (unprotected both ways) and a long, long bout of 69. Her circumcised cock is not massively long – maybe seven inches – but hugely girthy with a much wider head that gives it the look of magic pink toadstool. I manage the deep-throat the whole toadstool several times, but not for very long.
I fucked her first, but only briefly. My full-mast, blue-pill-assisted hard-on started to soften a couple of minutes after I got inside her in cowgirl. This often happens to me with anal penetration. Something to do with the grip all being at the entrance, perhaps, though I believe this has the opposite effect on some guys. Tiffany had been surprised that I didn't want to do it doggy-style, but I don't like that position as a top.
Being doggied is a different matter, and that's what we did next with her standing on the floor and me on all fours on the bed. Then missionary with my legs over her shoulders. And I've lost track of what happened in what order after that. In the end she didn't cum and I came in her mouth during another long spell of 69. It's rare for me to cum from oral so I was pleased with that.
We were slightly less than 90 minutes in at that point but I was fully spent, so after another 10 minutes of wind-down and chat I went on my way. It was good to see Tiffany again – and to finally get the magic toadstool inside me.
