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Tranny Stories

November 17, 2014 4:47 pm
Finally, I had everything I needed to dress up for a little fantasy today. Ever since I was a little boy, I had always thought my neighbor Steven was extremely handsome and sexy. At 6 feet 3 inches, Steven is exactly what is described as tall, dark, hard tone and muscular. Tonight, I would finally have my chance to fulfill a fantasy to show him just how much I wanted him. When I was growing up, I always heard he was a ladies man with many women lusting and chasing after him. So I always lusted every time I saw him with a woman or in passing, but not as boy, but a passionate woman thinking Stev... [read more]
Added by: shemale lover | Views: 1692 | Read full Story
November 16, 2014 10:27 pm
I led Chasity into the apartment. She was looking for a one bedroom, furnished place and had called about my ad in the newspaper. I hoped to rent this place quickly, then I would be full and could devote my time to some maintenance and repairs rather than showing places. I looked at the rental application she had filled out just a minute earlier. From the date listed as her birth date, she was 27 years old, three years younger than I. I watched her, explaining about the living room area and kitchen, as she moved about the place. Chasity's skin was about the darkest I ha... [read more]
Added by: Timsky | Views: 4186 | Read full Story
November 15, 2014 4:47 pm
After my first encounter with John’s dick, I couldn’t get it out of my mind. Two weeks later we met at a friend’s party and we talked about it. He was worried his girl friend might find out. I told him he had noting to worry about as I had as much to lose as he had. But I also said it was the best sex I ever had & wanted a repeat performance. He agreed it was fun but felt to do it again would be risky. I said all we needed was an excuse to go away for the weekend. I told him to leave it to me. I happen to mention to his girlfriend later that John & I were thinking ... [read more]
Added by: shemale lover | Views: 2684 | Read full Story
November 13, 2014 4:47 pm
“Blue-eyed boys always get me in trouble,” she said in a sultry tone with an equally sultry smile. I smiled as I looked into those warm brown Latina eyes, so soft yet full of mischief. “I’ll be back in a sec guys,” said Tracy as she got up from the table and headed towards the lady’s room. “Jack,” said Mike, the cook I was relieving, “you need to be careful with Tracy, “her name used to be Tommy.” “I know Mike,” I replied, “we met last night.” Yes, that was when I met Tracy. I had worked the ... [read more]
Added by: shemale lover | Views: 1903 | Read full Story
November 11, 2014 4:47 pm
Every one is programed by society to play a certian role in life,that they are taught is reality,how ever, the truth is reality is what ever you want to make it! this is what magic is all about,making your own reality. I played the manly role in life for fourty-four years until I realized this,and became free of society's brain washing!. Sometimes I would take a porno magazine and look at the pictures of the women in it and fantasize I was the one fucking the beautiful women in it and masterbate,and one day I noticed a small ad of a man dressed in drag and realized, yes a person could reverse ... [read more]
Added by: shemale lover | Views: 1470 | Read full Story
November 9, 2014 4:47 pm
This a true story about me and two very hot TS friends. I was down in Ft. Lauderdale and had hooked up with Lori and Heather. Two friends from my NYC days. They had relocated to Florida and told me to stop and see them when I came through. I met up with them at their apartment and we opened a bottle of wine and started catching up with each other. Heather was doing regular photo shoots for websites and had just done a movie. Lori had just finished her first photo shoot and brought out the proofs for me to look at. That was all it took, seeing her in different poses with her 35c breasts and har... [read more]
Added by: shemale lover | Views: 3420 | Read full Story
November 7, 2014 9:13 pm
I always has a fascination for transsexuals. I remember my freshman year of college, I don't remember how I stumbled upon it, but I was the most aroused I have ever been as I watched the beautiful Mia Isabella stroke her hard cock. Something about a feminine being, with large breast, voluptuous ass, and a beautiful cock. From this day on, I was infatuated with shemales, to the point that I wanted to have my first experience. I always dabbled on Craigslist, backpage, even on this chat for my first encounter. I had talked to several cross dressers and shemales, but was always nervous... [read more]
Added by: Drewbee | Views: 4713 | Read full Story
November 7, 2014 4:47 pm
I always love to crossdress when Im horny I love the feeling of being a woman and seducing a man. Older men have always attracted me here is my fantasy. I dress up one day with a red thong red bra black nylons short skirt and blouse and get online. I find a man who likes me and is ready to play. I come over to his house we start kissing touching and getting hot and heavy suddenly the wife pulls in I hide downstairs in a room only he can get into but little do I know his older guy friend is there watching the game.He asks me who I am I introduce myself and sit down. Hes a bit drunk he first put... [read more]
Added by: shemale lover | Views: 1782 | Read full Story
November 5, 2014 4:47 pm
I'd been Will's little CD slut every time that I'd overnighted in his city for about a year. That was one night every other week. He was always very good to me, bringing wine to my room and spoiling me with his gentleness as he had his way with me. He loved to have me lie still while he teased me all over with his tongue and feathers, sometimes fur gloves. He made me crazy with desire for a good hour before finally fucking me or having me suck his beautiful cock. One night he told me that he was being transferred and our time together was about to come to an end. He asked if I'd indulge him in... [read more]
Added by: shemale lover | Views: 2035 | Read full Story
November 3, 2014 4:47 pm
On the way back from Sidcup one evening last Summer I was busting for a piss. Getting near Croydon, I was looking for either a toilet or a wooded area. They seem to be closing all the toilets down nowadays. Just as I was near the stage of wetting myself, I noticed a sort of drive-in between bushes so made for that. That drive-in opened up to a small car park. I hurriedly parked my car in the corner, got out, noticed another three cars parked there, rushed over the bank, got my cock out and, whew, what a relief. As I was getting to the final jet stream I heard moans and squeals. I hastily tu... [read more]
Added by: shemale lover | Views: 2969 | Read full Story
November 1, 2014 4:47 pm
Due to my job, I had the opportunity to travel a lot. Once I had to travel to Barcelona and the complexity of the meetings required that I had to stay there for about 2 weeks for consultations with customers. After long working hours, normally we went for a nice dinner (nothing better than begin the evening with tapas and wine or sidra, concluding with a excellent dinner and a nice Rioja wine (or a white Albarino, one of the best kept secrets from Spain) After I was left in the hotel I searched the newspapers or the web to find some action, and boy, you could find a lot! One day I found ... [read more]
Added by: shemale lover | Views: 5671 | Read full Story
October 31, 2014 4:47 pm
The next work day, that evening as I walk up to my townhouse, Ann is sitting on the porch and tells me, “Since you didn’t call I thought I’d come by, I was in the area anyway.” Even though I’d been with her the night before, I have to laugh and Ann asks, “So what’s so funny?” “I’m not going to get close to this one.” I kiss her lovingly then say, “Please come in, a glass of scotch and cigarette, that’s what I usually have to relax me after work.” By then she’s loosening my pants and with a wicked... [read more]
Added by: shemale lover | Views: 1648 | Read full Story
October 29, 2014 4:47 pm
The weekend came fast and Miss Tranny Feet wanted to meet the man that had been sending her stories for weeks now. Each story had gotten more and more intense and now when she saw his name on the post, visions of long hours of touching her long slender legs worked her up into a rubbing frenzy. She set a long shower and soaped up her thin lithe body letting the soft silky sudds full in all her crevices.Closing her eyes and slowly stroking herself while leaning against the shower wall, thinking of how his weight against her back and the wet sliding feeling from behind will feel deep in her be... [read more]
Added by: shemale lover | Views: 1694 | Read full Story
October 27, 2014 11:29 pm
My name is Mike, as a "Gurl" I go by Fiona. I am a gay man, mid thrities, white, 5' 9' 165, reasonably handsome, both in and out of women's clothes. One of the ways I express my sexuality is to dress as a woman and get fucked by other men. Preferably in a humiliating situation, with several guys fucking me. Just one of my kinks. ~ This night was the second time I had gone with Anthony. The first time was the Friday Night before. I dressed in 3 inch heels, fishnets, black garter with thong panties over them, a black latex mini, a black leathe... [read more]
Added by: FionaFucked | Views: 2564 | Read full Story
October 27, 2014 4:47 pm
Ann was the woman who gave away free samples in the supermarket where I was manager, and as often as we could, the employees could find us sitting in my office, smoking, laughing and talking. Ann had a way of smoking a cigarette that drove me insane with sexual desire. Inhaling, her lips were puckered, full and looking like she was sucking a prick. Upon exhaling her cigarette smoke, she let the smoke only drift from her lips, as she simply exhaled it as she would her breath…I could not take my eyes from her each time she took a drag from her cigarette. Ann was sharp, witty, great sen... [read more]
Added by: shemale lover | Views: 3165 | Read full Story
October 25, 2014 5:47 pm
When I was 15 my friend Pete and I used to race around on our bikes nicking porn mags from corner shops. We used to take them to the local park and read through them with our cocks straining at our school shorts. As time went on we started to take turns going behind a bush or into the toilet and wanking off over the porn mags. I really wanted to suck Petes hot cock but I was too shy to ask so it remained a fantasy. One day I snuck up to the toilet window outside the tennis club to see if I could see Pete wanking over the latest edition of Club magazine. I nearly shot my load when I saw hi... [read more]
Added by: ryan31 | Views: 3794 | Read full Story
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