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Tranny Stories

68%
My first encounter
This story details my first encounter with a stranger I met over the internet. I was 25 and reall getting into being a girl, I dressed all the time, and dreamed of sucking a cock dressed as who I really wanted to be. So I took a plunge in meeting someone for a quick bj in the area. I sent him some photos of me and without even receiving any pics back I decided to meet him. He was young so I thought how bad could it be? I was so nervous getting ready. I was going out dressed as a woman to get some strange dick, it was exiting. I had my hair down and a black skirk on with leopard heels and a whi... Read full Story
29%
I have been out dune by my little brother by a big difference hi
I am 32 years old and my lady who was 46 and my little brother who was just 14 years old then wanted to have some fun and get my woman who was just the right for him he was just out of his mind about her and I was like I'm all about it and I was thinking that I was going to be the big cock an he was going to have the letter one and I was going to out do him but he was a lot longer and bigger around then I was I was like damn bro were in the fuck did you get all of that big cock and what went wrong with my little dick even when he wasn't hard his was still longer and more around and m... Read full Story
82%
Ann and I
Last night I had an awesome experience. I was down in Fort Worth to meet a tranny I had been talking to on squirt. I got off work early, took a shower and shaved my cock and balls and dressed in jeans and a t-shirt and headed down to Club Changes to meet her at four. The bar was pretty empty, Thursday afternoon and early. She showed up right on time wearing tight jeans and a crop top. Her long, natural brown hair was in waves framing her face, her full lips bright red to match her nails and toes in flat sandals. She was about 5’4” with a big ole curvy ass and she came right to me at the bar... Read full Story
47%
Amara Vadillo ( Sylvia Boots )
Vadillo was born and raised in Cuba. After emigration to Los Angeles she became Amara. After injections of hormones and silicone, she was a 34 DDD. She found work acting in shemale videos and performing at the West Hollywood Club 7969 under the name of Sylvia Boots. She became known for her love of the work, and that it showed on camera. She acted in over 50 videos (see ES.Wikipedia for a list), and as she had facial cosmetic surgery several times, she looks different over the course of her films. She generally got on well with her fellow actors, with one exception, fellow performer Tanya Am... Read full Story
71%
Becoming a Sissy - My aunt my Mistress
For more than 6 months i’ve got this fetish, whenever my mom is out i crossdress with her clothes. It all started with porn, and slowly i got courage and from a pair of panties i ended up full crossdressed, with the make up made. Everything changed on this day, when i decided to crossdress even if my mom was home, i closed the door of my room and started to get dressed,took my time tho. First took the panties, they were black made from silk, matching with the bra, after that I took the stockings also black, and finally the heels and the dress, which was slim soft but not fitting me perfe... Read full Story
54%
cindy and r.sissy
I meet cindy online we organized to meet at a motel l got there first l got ready l put on my black latex half cat suit my black with red trim latex blouse l put on my red platform thigh boots l was starting to get a hard cock but lhad makeup to put on did that and a great long shoulder length blonde wig l looked like a slut . Ten minutes later a knock on the door its cindy we meet for the first time we look at each other as l close the door well we both took hold of each other and we started kissing deep kissing l took hold of her cock while l was kissing her l unzipped my latex and out came ... Read full Story
68%
Sucking off a stranger
When I was about 18 I started checking out craigslist in the morning before school while watching porn to help me get off. I would fantasize about meeting the people who posted but I knew I couldn't as most of them wanted to meet while I was in school or lived to far away for someone with out a car. So one day I decided ditch school and post my own ad to give a blowjob. I nervously typed out what I wanted to do and that I wanted to meet someone near me and clicked publish. It took about 15 minutes for my first real reply. He said he could come and get me then go to his house and get down ... Read full Story
56%
story of Jojo
Some find it confusing of who i am or what i am, including me. i found some kind of definition: femboy A young boy who presents extensive feminine mannerisms and actions often blurring the line between a boy and a girl. Can be confused with a cross dresser, but it usually refers to boys at very young age or in their teens. Commonly used to define gay boys who dress like girls, but some can be straight too. There are many variety of trans. We know transsexuals who like boys and girls and are desperate to keep the cock. i like them a lot. We have transgenders girls born in boys b... Read full Story
80%
My first cock
I have been crossdressing for many years. When I was younger I would wear my moms pantyhose and stockings .After I was married I would wear my wifes nylons and started to buy my own. Everytime we have sex my wife wears crotchless pantyhose or thigh hi stockings. Yes I have a nylon fetish. One day after putting on pantyhose I decided to try on a skirt, then a silky blouse. I thought I was looking pretty good and I was really turned on when the skirt would rub along the pantyhose. I eventually bought my own womans wardrobe, lots of nylons,bra,clothes,wigs,heels and makeup. Now instead of just pu... Read full Story
62%
Alleyway Adventure
One day after school I am walking to a coffee shop and I notice this hot chick waving at me to come over to her. She is wearing a tight pair of Lululemon yoga pants and only a bra on top. As if in a trance I walk over to her and she smiles. She leans over and whispers in my ear "Do you want to come someplace more private with me and i'll show you what i've got for you?" I say yes and she takes me by the hand and leads me towards a alleyway behind the coffee shop. Before we go in the alleyway she moves her other hand and puts it on my growing cock. Smiling she leads me to th... Read full Story
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