I have, once. It was a great experience.
My first choice TS escort bailed on me at the last minute, and I took a punt on one of the others who I suspected the picture might not have been real. It wasn't, but I'd resolved that unless she was really ugly, or manly, I would go through with it no matter what. (I like TS to look like girls with dicks, rather than men with tits, if that makes sense.)
It was in-call, so I waited outside, round the corner to walk her in to the hotel. She was pretty, long hair, with a small, delicate frame, but very flat. (On a girl, this would probably be a quirky kink, but slightly disappointing on my TS.)
We'd discussed what i wanted on the phone (watersports, anal and oral, give and receive).
She had a lacy leotard on under a long coat. We kissed as we slowly got undressed, and stroking her cock through the lace was the first time I'd touched someone else's.
We went to the shower, showered together, I sat in the tray as she peed on my cock as I stroked before sticking my face under the stream, then opening my mouth and then taking her cock and sucking her to hardness.
We cleaned up, dried off and went to the bed. More kissing, mutual masturbation, turns giving oral (both OWO), rimming, fingering...
She then put a condom on her cock, got some lube and fucked me on my back, then on all fours, all the while I was stroking.
She was clearly getting close so I told her to pull out, I took her condom off, laid her back and started fingering her ass, sucking and stroking her cock, intermittently kissing her, and then as she neared kept on stroking while kissing her until I felt the first spurt, at which point I took her into my mouth to suck it all down.
She then brought me up to the head of the bed, stroking me and giving me oral, before slipping her fingers inside to massage my prostate. Combination of her fingers inside me and her hand and mouth on my cock...I blew the massive load I'd been saving for her (only edging all week) all over her face and body.
I licked her clean before we both jumped in the shower together and she then left the room with a long kiss at the door.
If you're curious, I'd say just go for it!
