Pantyhose Crossdresser Stories

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Orientation
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Infinite Scroll

How I Became a Crossdresser

by Chrispe69 on Sep 16, 2017
Transsexuals & Crossdressers

I've always loved everything about women. I love their curvy feminine features, their long painted fingernails, the high heels they wear and their silky smooth clothing. When I was young, I liked the women I dated to be flashy and slutty looking. I never had much trouble getting the sex I was after from these women either. I got married in my late twenties...

Stockings & Stalkings Pt. 01

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Giselle applied the clear topcoat to her ruby-red lipstick; she pursed her lips as she looked at her reflection in the mirror. "There; finally finished," she smiled to herself. It had taken Giselle nearly one hour to transform from 'Gary', her male alter-ego, into Giselle, the hot transvestite staring back at her from the mirror. She smiled to herself as s...

Michele Nylons' True Stories Ch. 02

by MicheleNylons on Jul 14, 2020
Transgender & Crossdressers

In part one of True Stories I discussed how my transition from part time panty wearer to part time Transvestite came about. I also told the true story of my first time with a Transsexual prostitute. In this instalment I have decided to leap ahead to the present and tell you a true story that occurred only last week; that is July 2006. I am a part time Trans...

Ugly Duckling to Sissy Princess

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

All names have been changed to protect the guilty. ***** Being a very short guy (5'3") with a small frame has been a major handicap in my quest for female companionship. Having a micro penis was the nail in my coffin. Throughout my youth, I was ignored or rejected by girls. I had my first girlfriend in college, Caroline Fletcher. She was smart, beautiful,...

Recruiting of a Sissy Maid Ch. 13

by Sissy_Chantel on Nov 28, 2017
Transsexuals & Crossdressers

Chapter Thirteen: A Business Trip to an Adult Movie Convention, Carl and Chantel Consummate a True Loving Relationship. Carl says, "Chantel make sure you pack well but not slutty ok. I will have you travel with me as my girl friend and secretary. Dress nice but casual for our flight but of course still be an eye catcher ok?" Chantel replies, "Ok hun, I fig...

Kissing Crossdressers Pt. 01

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

It started when Carla, my hot sexy wife went away on a spa break a few days with some of her girlfriends. Carla is 40 (I'm 48), has blonde hair, blue eyes, 34DD tits and a curvaceous ass. She works long hours in a busy office as a manager, I work in a local library and my job is far less stressful than hers. And her job has definitely taken its toll on our s...

It Started As A First Date

by spandexman on Aug 30, 2017
Fetish

As far as first dates were concerned, Roxy Fox, the 23-year-old, 5'11", Barbie doll faced gorgeous, secretary, with a strong dimpled chin, high cheekbones, big almond shaped hazel eyes, thick wavy shoulder length fiery-red hair, and a very firm, but extremely curvaceous 38FF-26-38 hourglass figure that her skintight white spandex pants, tight red spandex top...

Tranny Chasers: Bernie and Ron

by 1946EW on Sep 12, 2017
Transsexuals & Crossdressers

Bernie looked around as he entered the Cavalier d'Eon, checking out the patrons. Spying his friend Ron, he worked his way over to him. Ron was sitting at the bar, back to it, also checking out the patrons. "How's it hanging, Ron boy," Bernie asked, easing between Ron and the guy sitting next to him. "Low as usual, Bern," Ron replied, turning to his beer on...

Dreams

by DrLuverotica on Sep 25, 2017
Transsexuals & Crossdressers

"Hey! Hey! Wake up, wake up!" "What? Jo, what is it? What's going on?" "I think you should be telling me that!" "I don't understand." I was slowly coming round now, But I was still mystified as to why my wife had woken me at 2 a.m on a Saturday morning. "Erm your cock is as hard as nails and you were waving your ass in the air," Jo said, starting to laug...

The Roommate Pt. 11 - Miranda

by ValoryG on Sep 19, 2017
Transsexuals & Crossdressers

Josh/Lori, having lost her virginity to Miranda's penetration, and feeling even more like a woman, settled into teaching again. The rewards of passing on his passion for literature to young students was considerable, and now he could increasingly see characters from male and female perspectives. He was especially interested in learning how his female student...