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Tranny Stories

Dick And Ass
I don't have this kind of sex often, I feel like it's wrong to want this, wrong to crave this so badly. I am by no means a sissy or a gay man. I have a wife a family.... I just need it the domination the surrender of all my will and being, the first thrust that hurts so fucking bad when it goes in... I was on Craig's List and saw the ad "Ass and Dick!! I wanna lick your ass and suck your dick maybe let you fuck me if you want." I clicked and there she was 6ft BBW make up very show girl like. I like how she looked and her ad was super hot so I wrote her and she was quic... Read full Story
Shemale Porn Photo On The Wall Of Her Room
She was a truly hot shemale that I’ve been seeing for a couple of months now, from time to time. She had some really big tits and a dick that didn’t really get in our way much. It really wasn’t all about the sex. I loved talking and even cuddling with that girl. We talked about everything and anything, but she would never tell me what is the thing with a big shemale porn photo on her wall. I asked her a million times, but she never told me. In time I gave up. After all she told me that if it ever became important for me to know, she’d tell me. That day I came to h... Read full Story
He Was Way Too Much Into Shemale Stories
At first I didn’t find it to strange. As far as our sex life was OK, I was totally fine with the fact that my husband reads ten shemale stories a week. Until one night. I came back from a business trip a night to early. I managed to grab the late plane and arrived home sometimes after midnight. I supposed that he was already asleep, so I tried to be very quiet entering our house and going to bed. As I entered our bedroom, I was in for a shock. I saw two silhouettes in the dark, apparently fucking in doggy style. I screamed and turned on the lights only to be shocked even more. Ther... Read full Story
Who Could Choose Between Shemales And Females?
I knew that this guy was one of those eccentric rich people who don’t really know what to do with themselves, and I was not really expecting an invitation to the party at his villa on the beach. But why not. I don’t refuse free drinks and other stuff that can make you happier about your life. I could see that it was a regular fuck fest even before I got out of my car but then I saw a banner at the entrance saying Shemales and Females. “There’s first time for everything” I thought and entered the villa’s garden. Gorgeous girls were barely dressed, drunk... Read full Story
My First Sissy Meet Up
I had posted an add on craigslist asking people to let me suck them off at my place. After sorting out all the answers that I got I found a guy, John, that was incredibly eager, we agreed a time and date. The day came and I woke up so nervously. But I was determined to not let it show so I got up bright and early and jumped in the shower, I made sure I was nice and clean everywhere. I exfoliated everywhere and rubbed myself down with moisturizer and lavender oil. Making myself feel as feminine as possible, I had put my clothes out the night before, some nice red and black crotchless lacy... Read full Story
The Hottest Of The Teen Transgender Stories
She was a cheerleader in college and I was…well. Me. I lived one of those transgender stories where I was still stuck in the middle of my transition and I wasn’t a girl anymore, but I wasn’t the guy she needed. She had every single guy in the campus she wanted and I had..well. Me. I met her couple of times on the tennis courts. I loved to play it and so did she, but I thought that I was invisible to her. One day she played in the court next to mine and I enjoyed the sight of her ties flashing under that tiny skirt and her breasts bouncing with her every hit. I stopped ... Read full Story
Is it just me?
Well, I don't even know where to begin with this one? But, anyway? I went out with a friend of mine who had a couple of girlfriends that we were to meet at a club that I had never been before? And neither did my friend tell me that he had been there to the club before either. So, when we got into the club? For some odd reason, I became the center of attraction, I don't know if it was the shorts that I was wearing, the cologne or what? But when I sat at the bar, there were these pretty ladies all over the place, but by me being shy? I kept to myself, but I was approached at least 20 times that ... Read full Story
Nobody Forgets Their First Time With Shemale
Her name was Veronica. She was about 6" tall and her heels were so high it made me dizzy. Actually, together with the fishnet stockings she was wearing, it made me dizzy and horny. It was my first time with she-male and my first time with that kind of service. Veronica knew that was my first time. She asked “I know you’re nervous. Just let me show you all the things that we can do.” As I was sitting on my bed, she got down on her knees and started caressing my dick over my pants looking me in the eyes without blinking. I was seduced by her looks, her self confidenc... Read full Story
Making of a Sissy pt2
After Tom had dressed me & now had the photo evidence I knew I was at his mercy. I also knew that the blowjob I had given him wouldn't be all he was looking to get from me to keep my secret. He was soon messaging me, telling me when to be at his, along with a picture of me dressed, with a cock in my mouth and a face full of his cum. Knowing I had no choice if I didn't want that picture plus the many others to be public knowledge I agreed to be there Friday night. I arrived around 8pm and was immediately sent upstairs and told to get ready as he wanted me. I went up & w... Read full Story
She Male Photo Gallery Brought My High School Fantasy To Life
A friend of mine from high school came to visit me after many years when I moved into my new apartment in Los Angeles. We were good friends back then and kept in touch, but we went apart due to our careers. He was even one off the first and few people I came out to in high school, so our relationship was tight. I even had a big crush on him at the time, but he is unfortunately straight. I invited one evening some of my friends to have some drinks and see what we would do that night. We had decided to play it by ear. The crowd seemed to like my friend and everyone was getting quite comfortab... Read full Story