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Tranny Stories

My First Time
This is my first ever story written about my first ever sexual encounter with a transgender woman. I really hope you enjoy and want to leave me some feedback… I have slept with many women in my life. I have been married, had more girlfriends than I can remember, several fuck buddies and far too many one nighters to tally up. Up until recently I have always been a guy exclusively into women, natural born female variety. Sure, probably like most guys, I have considered other options but always recoiled at the thought of getting it on with another guy. Oh God no, I could never do that! I kind ... Read full Story
A long fun weekend with Desi
I come over to your place after work on Friday evening. We are going over to one of your friends houses for a get together. I head home real quick and change clothed and get my bag for the weekend. I shoot you a text as I head out the door, "On my way". You are at home getting ready to go out. Thus get together isn't anything fancy so you put in a pair if tight jeans that accentuates your ass and a cute top with spaghetti straps. I arrive at your house and walk up to the door and ring the door bell. You are still fixing your hair so you just holler for me to come in. I come in ... Read full Story
Real TS Encounters
Real TS Encounters Lay Report #1 Thursday June 9th, 2016 Hey, so this is my first “Lay Report”, which is what I will call them for now. My intent with these is to share stories of my encounters, while at the same time being informative enough to the point where you can get some value from this as well. So it was Wednesday June 8th, 2016, about 11 pm. I did something I rarely do [anymore] and I went on Craigslist. I was in the mood for a new girl, and 11 pm is slightly late to be calling some of my current regulars, especially on a weeknight. If you’ve been following me/my webs... Read full Story
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
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