Who, When, How........was your first time with a transsexual?

[alexanderseven]

My first time was with Yasmin Lee in Boston, about 4 or 5 years ago, I believe. She was amazing- so beautiful and sexy and sweet. I was not in a great place, however, back then. I was nearly 300 lbs and had a lot of self esteem issues. Those issues prevented me from doing a lot of the things I really wanted, with her, and with life in general. Happy to say that a handful of years later, I've lost 130 lbs, I'm fit, and I've had a number of relationships with tg girls. Life is good. In some way, that meeting with Yasmin really gave me the impetus to get my life together, physically and mentally. If she reads this, I'd like to say thanks. You were amazing.

[magus13]

About 13 years ago the most amazing ts was visisting NYC. Her name was Ruby and I told myself that would be the the ts I would get my nerve up to meet. Had an amazing session. Top bottom mutual cim. She asked what I wanted, I told her to be my girl. She said that she was my girlfriend for the next hour and it was an incredible experience.

[timid1]

Who...
When...
Why....
How...

Were you addicted the first time..weirded out..

lmao the list goes on..do tell..

The beautiful Valentine in West London.
Early Nov. this year
Why? Because I could no longer resist the urge to experience a tgirl , and she looked incredible, and her reviews were fantastic.
She was very sweet and even more beautiful than her pics. I was incredibly nervous , but she was extremely kind and reassuring. It was an amazing first hour . I was a little uncertain and she wore a condom when I started to preform oral, however after about 60 secs I begged her to rip it off! Oral was far hornier without a condom, for sure! I was soon begging for her to penetrate me, which she did expertly!
Yes, I'm now addicted! And I felt elated and euphoric after the first time (which was pleasantly surprising) . I enjoyed Valentine so much I visited her again 4 days later !
I love girls , but sex with tgirls, for me , is even better!
I'm so happy I took the plunge, and that I was lucky to have a wonderful first experience
x

[dickten]

Growing up Catholic in all boys schools is tough on the emotional adolescence needed for sexual maturity. I loved girls and they seemed to love me, but I never had the courage to talk to them. I had one girlfriend in High School who went to my prom, but it was just very casual friendship. Once I left the small town to be on my own at college in the big city of SF 1976, I seemed to develop what I would call a path of fate. You decide. One night some of my buddies decided to go into the tenderloin to a theater where they had strippers. On the way back walking out of the TL a beautiful asian lady stopped me and asked if I wanted to party? Her voice seemed different and even before I knew what clocking meant, I seemed to sense she was a man, but still a very sexy one. She grabbed my hand, gave me a kiss on the cheek and told me how cute I was. At that point, man or woman, I was very idealistic about sex and knew that I did not want a one night stand. I told her how flattered I was and how beautiful she was and told her that I wasn't into that. She took my hand and put it on her crotch to tell me what I was missing. The hardness shook me and I quickly left. One year later I am in New Orleans for the Sugar Bowl and mad drunk walk into "Papa Joes" , what I thought was a burlesque place. I then notice it is a female impersonators bar, which was not too shocking since I had heard of places like that before in Boston growing up, but still probably not my choice as I was drunk enough to say anything to any girls and wanted to try and get laid. Before I could turn around, I tall thin latin brunette in a black sparkly dressed grabbed my hand and brought me to the back of the place, sat me down, sat on my lap and ordered a round of drinks for us. Very expensive drinks btw. We started to talk and then I realized she was one of the performers. Not much I could do with a lady on my lap, so I just sat and talked as she asked me all types of things. I told her I came in by mistake, which she didn't believe and decided to inspect my package (It was dark in the back) This oddly felt good, but I knew I had to leave and my chance would come when she had to get up and do her "set". We had a couple drinks and she kissed my neck a couple times sending shivers thru me, but when she got up, I bolted and spent the entire next day questioning my sexuality. 1980 My First corporate job in NYC, Living in crappy Tribeca before it became what it is today. One night I decided to hit a Broadway show with a girl cousin of mine, after the show I walked her to Penn Sta for her train and walked back to Times Square for a quick jerk in one of the peep shows. Walked into Playland (next to Port Authority) and noticed they had a live sex act downstairs which sounded interesting. As I walk down the stairs, I notice you need to run a gauntlet hallway of two way booths full of TV's and TS's before getting to the live action. One very aggressive black TS Grabs me and yells fresh meat, pushes me into the booth and tells me that the manager is not around and that she does not need to go into the adjoining booth. I'm fumbling for something to say, while she reaches under her skirt and puts her anacoda in my hand. All the while this is happening, all the other TS's are in the other booth watching to see what will happen next. I kindlly tell her that she has quite a nice pet snake, but that I'm not into snakes. She acts like all pouty with please, please, it will be so nice, etc and I manage to side step up and over around her to get back into the hallway and then I'm met with a cute white Ts who blocks the way and asks if I'm into white girls more? No, just want to go see the "Live" sex show I tell her. After a while I make it to the area where the little booths shut behind you and the wooden slats open up after you throw the coins in them to reveal two girls licking each other. They walk around allowing you to dildo dip them for a fee. Pretty cool, hot, degenerate stuff, but I can't seem to get my mind off the "Ladies" in the hallway. I leave shortly thru the "Correct" exit by the side that I should have used in the first place a little shook up and even more confused. A year later I am coming out of a bar in the Lex and 20th street area and notice a ton of Ts's all working the streets, this amazes me and I watch from a distance for quite some time. It's the first time I notice that some of the girls are prettier than most woman. I then go search for a subway home and also look to get the morning edition of the Times. As I reach for a paper, so does this young, cute, asian girl too. I laugh and let her pick first, go buy it and take my time looking at the headlines in hopes I can say something to her. She is first and asks if I live around here? Tell her no, that I was with friends for dinner and drinks, we talk a little bit, she tells me she goes to college in the city, she lives at her brothers little apartment while he works in London. Asks what I do and then invites me up for a drink. We kiss and fool around a little and then i ask her if we can go out the next night, that I liked her and was a gentleman and wanted to get to know her better (How stupid of me) She was fine, tiny, thin, sexy features, etc. We exchange phone numbers and I'm pumped! The next day I get a call from a man telling me it's her brother and that Mimi really liked me, but wanted me to know that she was born a man. She did not want me to get mad on the date and she was embarrassed to tell me last night. WOW... NYC is crazy, he then asks if I still want to pick her up. I mention I needed to think about it and that I'd call her back that day. I never called. Pretty shitty thing to do and to this day I still feel bad. A month later I'm in the village partying with my cousin who decides he needs to come out of the closet to me. I'm the only family member who understands and he even wants to know if I might be gay? Fuck, I'm batting 1000. By this point in my life I've had a couple of girlfriends and sex 3 or 5 times and with all these TS run in's I'm not sure what I am. He decides to take me to this bar on Christopher Street called "Boots and Sadles" to see the other side of things.
I walk in and I finally figured out what it feels like to be a hot chick in a bar. I was 22 and had tons of guys trying to buy me a drink or talk to me. I told my cousin to pretend he was my boyfriend so that this would stop. It helped a little. Until his real boyfriend showed up and asked him if his cousin was gay too? I told him I didn't think so, none of the these guys did anything to get the old butterflies going, which was nice to say and to feel. They then wanted to go try another bar further down the street called, "The Anvil" and I told them, OK, Only one more bar. This place was extreme, guys in leather, guys in 40's and 50's, you name it. I told them it wasn't for me and that I was going to head home. All this after taking a piss in a bathroom where I could hear guys fucking in the next stall and getting blowjobs in the outside hall. Too much for me. On my way back to the subway, there she stood, in a gold glittering dress, a latin Diva with big hair and high heels in fishnet stockings! She asked if I could give her a light? I told her I did not smoke, she then asked if I wanted to smoke some weed with her if she could find a light? She had just come from a place called the florent restaurant with two of her other friends and I think she may have been done working for the night. The other two ladies walked away and told her to have fun and told me I should escort the lady home. This time I was not fooled and felt a little peace in understanding the situation. I told her ok, stepped into a little store to buy some smokes for her and get a Bic. We walked the thru the Meat Packing district talking and smoking watching the crazy night life unfold around us in the Pre-Gulianni era. Made it to her apartment and ended up making out like teenagers. I told her I like her alot, but that could we slow down (Again, punking out) But she actually liked the idea and we slept in the same bad all night just holding each other. In the morning I took her for Breakfast and caught a glimpse of her looking like a young man in the bathroom which kind of spooked me. At breakfast she told me that she was from Monterrey Mexico, family basically disowned her, but she had cousins in Alphabet City that knew about her and kind of accepted her. She had a Day Job a a Florist, but it was not enough to pay for her Hormones, Fashion, etc. She did work at night, but wanted to try and find a better paying job at Macy's or Barney's as a sales girl (she could pass easily) That following night I looked in the village voice for a good Mexican Restaurant to take her to. I think it was called Los Lobo or something. After Dinner we went back to her place and explored each others bodies and she let me suck her and vice versa, then I could not wait to be inside her and the combination of kissing her and looking down at her hard cock was too much and I then had the best orgasm of my young life. We then began a 2 year romance that I'll never forget her. Summers at the Beach in Montauk, partying our asses off at Peppermint Lounge, CBGB's, Mudd Club, Danceteria and Mott Street dim sum every sunday to work off hangovers. She eventually got to work at a store in Soho as a Sales Girl and I heard she even went back and got her degree and is doing something in fashion to this day. It's funny, when I visit, I try and pass by our same old haunts to hope and catch her on the street, but as you know, everything has changed since then and have had no luck. Since then there have been two other long term Girl Friends who were Ts. I often think that it was a series of these events that drew me into my predilection, possibly other things? My relationships have been rocky to say the least, it comes with the territory if your man enough to stick around, but I would not trade it for anything. I'm currently seeing a younger Ts now, she is very bright , smoking hot and tells me she loves me,
but it's still early, she has strayed a few times and I understand more than anyone that this seems to come with the package. Growing up with a father figure who never loved back or was abusive or growing up and wanting the attentions of boys who may have treated you badly or thought you were not pretty can be a factor in why people need to seek constant male attention thru sex, but that's not going to stop me from trying to find the right person or at least work thru that persons problems if I love them. It's all just part of the deal in enjoying these exquisite ladies in our hearts.