After seeing a couple of dom's and getting the strap, I figured it was time for the real thing (even though I didn't get fucked for YEARS after seeing my first TS).  

Found a semi local girl here in Pedro (I'm from PV), I don't think the ad even had a picture.  I remember walking up to the house, turning around and walking back to my car.  Twice.  Then I said fuck it and just went for it.  She said she saw me walk back to my car, but of course this is back before cell phones and texting were the norm.  In fact, I had to make that infamous 2nd call from a local payphone that she told me to call from.

She was cute, had a fake rack and a smallish cock.  We did everything covered 100%, even mutual bj's.  I remember the first time I felt her cock, it was a very surreal feeling, as I've felt my own, but never anyone elses.  She taught me how to suck her, as I was using quite a bit of teeth and not actually sucking at all.  I think I was so excited, I came with her barely sucking me off, with a condom on.

Since I had a good time, I would go back now and then.  I was so scared of picking up anything that I remember laying next to her one evening and she reached to put my cock in her mouth uncovered and I freaked out a bit and made her cover me up.  I remember her getting an offended look and attitude, but I think she understood.  I remember that was the night I first had some TS asshole and boy did I fuck the hell out of her.  Was making her gape and fart, the whole nine, she was moaning and loving it.  Wound up coming a few times I guess, as she had a puddle under her when we were done.  And I'm sure I didn't last more then 10 minutes tops.  

Wasn't going to go back, but...left my work jacket there and had to come back for it.  So I wound up seeing her about 4 or 5 times total.  

I often wonder what happened to her and have drove by her old place once, but didn't see what I believed to be her car so I just kept going.  Wouldn't mind seeing her again, just to get that image back.  Can't really remember her face very well.  

 

And yours?

Back in early 1989 left work one night with a few friends and we drove past the meat packing district around 14th street on the west side of manhattan. Saw these physically bigger girls who I knew had to be hookers but they looked great and dressed even better, a friend clued me in that they weren't women but
were actually TS. I was back the next night to check out the scene better and was intrigued, but was terrified of LE, so I drove to another area in NY called Hunts Point, and there were a few TS there, not as glamourous as those in manhattan but still decent looking. Finally got up the courage to approach one of them and went for it, she directed me to a secluded area not far away and for $100 got me off in about 15 minutes. She offered to take me back to her place where we could be more comfortable and to ease my mind about LE for an extra $20. Over the next year or so I saw her about 5 times at her place and things were great, she knew exactly what I liked and was willing to accommodate my special fetish. One night at her place I noticed a picture on her wall and my heart skipped a few beats, there was a picture of a guy I knew that was the brother of a female co worker of mine! That was my last time seeing her but it was good while it lasted.

I was extremely nervous.  I had been with a guy in a MMF threesome, but not tried the "two-in-one" package of a TS.  This was back in the days before reviews, so I had to rely on the website and go with my gut feel.  I ended up being very lucky.  She was a hot blonde (hot in a very dirty, nasty kind of way) and she incorporated BDSM into her sessions.  She also offered boytoys to join the party, but I was not ready for that, but definitely would be today.

I got to her incall apartment, and she let me in and we got acquainted on the sofa.  She had colored contacts, which made her eyes look amazing, sucking me in for a unique experience.  After the LE check and taking care of the donation, she told me to go into the bedroom and undress and she would join me when she was ready.  I did as she instructed and when she entered the room, she had on leather boots with fishnet stockings, a black leather thong, and black leather bra.  She was holding handcuffs and a leather crop.  She ordered me on all fours, climbed onto the bed behind me, pulled my hands behind my back and handcuffed me.  I can't really describe the feeling of fear and excitement that went through me.  She worked a dildo into my ass, which I was not expecting, but worked past the pain until I was enjoying her sliding it in and out of my ass.  She was using the crop on my ass, stinging me, but luckily not leaving any marks.

She released me from the handcuffs, rolled me over on my back, then handcuffed me to the metal headboard.  She stroked my hard cock, took off her bra, and crushed her breasts against my face.  I sucked on her nipples, biting as she instructed, and she gave my hot deep french kisses in a very aggressive way.  She was taking what she wanted and was clearly in charge.  She took off her thong and shoved her cock in my mouth.  She was 6-7 inches and still getting hard as I sucked her the best I could.  She slapped my face with her cock and pressed her balls and asshole against my lips.  I had no choice but to suck on her balls and run my tongue over her asshole.  She moaned her approval as she ground her ass against my face.

She released me from my handcuffs and rolled me on top of her.  The scene changed from aggressive to sensual as I deeply kissed her, then worked my tongue down her body.  I ran my tongue down her neck to her nipples, teasing them with my tongue and some light biting.  I then went down to her cock and started sucking, engulfing her into my mouth.  I was not letting her out of my mouth until I made her come.  It took me about five minutes, but she lifted off the bed, thrusting her hips into me as she came down my throat.  She cried out and shuddered as she emptied into my mouth.  I swallowed and cleaned up her cock with my tongue.  She brought me up to her and kissed my deeply, thanking me for making her cum.

She ordered me to my knees in front of a chair and sat down.  She ordered my to stroke my cock until I came.  As I got close to coming, she ordered me to cum on her boots, then lick it off.  This pushed me over the edge and I exploded onto her leather boots.  She took hold of my head, forcing it down to clean up the mess I had made. I licked my cum off her boots, mixing it with hers in my mouth.

I was very lucky to find the right TS to introduce me to the experience, as well as give me an introduction to BDSM.  I never got together with her again as she travelled and ended up moving.  I will never forget those couple of hours with her, enjoying being her cum slave, getting my first incredible taste of a woman with a cock.  Truly, the best of both worlds!

My first time was a genuine surprise. I lived in NYC for many years and used to go to the windowless peeps a lot in Times Square. (Yes, pre-Giuliani) I went to a new place that had a different system, you would go into a small room with the girls instead of the booths. The girls were all black and Puerto Rican. I chose the cutest one, a 5'2" little PR "girl" that was super hot and very young. We got into the room and I negotiated to finger her pussy while she jacked me off. I took down her panties and out sprang a fully erect uncut penis. At the time, I truly didn't know she was a tranny when I went in and certainly wasn't expecting it. I was really surprised! She sucked me off while I jacked her off. It was the first hard on other than my own that I ever felt. I went back looking for her a few times but she was never there again and the place closed down shortly thereafter. I didn't feel another cock for about 7 years and wasn't with another tranny for about 11. I have the image of her hard cock burned into my mind and hopefully will forever! It was totally HOT!

Mine was really similar.

2000 or so, I went to a "mixed" strip club (gay/straight) with a few friends and hooked up with a pretty amazing asian lady.  She insisted on keeping her skirt on while she danced for me downstairs, but it came off in the private VIP booth.  

She was rubbing/riding me RCG so at first I didn't know because she steered me away from the Y, but we eventually  negotiated for some...extra attention, which she provided veeeeeery nicely.  She swallowed and came up for air and I was seeing stars when she turned around and I saw her...extra gift.  

I jumped up, but before I could get out, she talked me down and we ended up making out on the couch.  Crazy hot kisser and I really enjoyed her, particularly when she mounted me CG and rode me while we made out.

I didn't start seeing TG's regularly until 2003 when she quit the club and moved out of town.  Sometimes I wish I'd let her top me, but she was awesome.

Haven't done it yet. Fantasize about it all the time. Even have the girl picked out I think. Just have to make the plunge and go for it. Thanks for the hot accounts, guys. Any tips for me?