Transgender & Crossdressers Stories

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The Story of Vicky

by drlove1968 on Sep 12, 2017
Transsexuals & Crossdressers

How I became Vicky is a lifelong story that turned out to be nothing I could have ever imagined it would. You see, I have always been the ladies' man, I thought, and loved the feeling of a girl all dressed up in satins and lace. I also have always been very cocky and somewhat full of myself. I have always been able to make a living, or at least get by, with...

Fantasies Fulfilled

by Cindytranee on Sep 13, 2017
Transsexuals & Crossdressers

This story is part true and part fiction. It basically happened as told with a few embellishments. * I enjoy crossdressing and do so when ever I can. About the only time I dress as a man is to go to work. I have been doing this since I was eleven years old. I love to have sex with a man as if I was a woman and really think I should have been born a girl. I...

The Anniversary Present

by DrLuverotica on Sep 15, 2017
Transsexuals & Crossdressers

My wife, Jo, is a very hot, very sexy 40 year old doctor. For the past few years I've found it really difficult to please her sexually. That all changed when I bought her a Rampant Rabbit vibrator from Ann Summers for our tenth wedding anniversary. When Jo unwrapped the box containing the 8 inch silicon black vibrator she was giddy with excitement. I was de...

T & T

by My5InchFMHeels on Sep 15, 2017
Transsexuals & Crossdressers

My "Sister" and I have always been close growing up, we've shared "almost" every detail with each other, or so I thought. I say "Sister and Almost" very loosely, but neither have hardly any truth to them. My name is Anthony, most call me Tony, my sister's name is Terrance, but everyone calls her Teri. Teri and I were born identical twins, but we have grown u...

An Expensive Addiction Ch. 03

by NeverGuessWhatsNext on Sep 16, 2017
Transsexuals & Crossdressers

The Friday after my second encounter with English was just as eventful as I had thought it would be. My girlfriend got to town, and since we hadn't seen each other in weeks, she was hornier than hell. I picked her up from her parents house around 5 and we went straight back to my place to have sex before going to the party. A couple of months after we starte...

An Expensive Addiction Ch. 02

by NeverGuessWhatsNext on Sep 16, 2017
Transsexuals & Crossdressers

A week went by following my first encounter with English, my tranny escort, before I found myself craving another. Every day when I jacked off I thought of her sexy slender body and that big thick, long, uncut cock. The feeling of her hands running through my hair and then pushing on the back of my head to force her cock into my mouth...then the incredible s...

Becoming Cassie Ch. 01

by TGJamie on Sep 25, 2017
Transsexuals & Crossdressers

Money was hard to come by in our household. Being the oldest of four and my mom being a single mom put a real strain on our resources. Rarely did we ever have any extra money in our family to spend on things like eating out at a restaurant or going to the movies. If we wanted to do that, we had to save our own money to do it. Things were just tight. That sai...

Womanhood for Jenny Ch. 03

by slutty_jannelle on Sep 12, 2017
Transsexuals & Crossdressers

NOTE -- This is a work of fiction, intended only for the entertainment of adult readers. * Jenny woke sore and stiff from her 'engagement party' session with Master last night. Padding silently to the bathroom, she began her daily ritual: douche, shave, and shower. Admiring her new implants in the mirror, she was proud of her feminine curves, and the bruis...

Meeting in the Toilet

by whistful on Sep 16, 2017
Transsexuals & Crossdressers

I am dressed in my sexiest lingerie, a suspender belt holds my sheer black stockings nice and high and firm around my thighs, a tiny black lace thong hugs my cock and balls. The purple trim on my thong matches the suspender belt, as does the bra I am wearing. A picture in black and purple, I think I look as sexy as I feel. I have been sitting in this cubicl...

The Lap Dancer Ch. 03

by Travel_by_day on Sep 16, 2017
Transsexuals & Crossdressers

After the break of more than a week between my first and second lap dances by my cross-dressing roommate, the frequency of our session increased dramatically. The transformation of my roommate Jim into his female alter-ego Jubilee and the transformation of our living room into the strip club "The Pussy Pole" was soon a daily occurrence. "Jim, you realize th...