Crossdressing Sissy Stories

7,212 results
Orientation
Length
Source
Infinite Scroll

Caught in Her Panties Ch. 01

by Knightofround on Sep 12, 2017
Transsexuals & Crossdressers

In the past few months I have been curious about myself. I am a straight guy, always have been, but that's not to say I haven't had fantasies about trying something new. A girl I dated when I was 19 years old, I am now 28 years old, was a big freak. She was very dominate and loved forcing herself on me, both in private and public. She would tie me down and p...

First Time Blowjob

by MyWhoreWife on Dec 10, 2019
First Time

I'm a man and I love crossdressing. I love the feeling of nylons on my legs and wearing strappy high heel shoes. While wearing them I would wonder what it would be like to suck a COCK in them. Kneeling between a man's legs and sucking his hard and meaty COCK. I started to go to adult cinema's in the downtown area after accidentally discovering their existen...

Real Life: The RPG

by Katnaace on Nov 25, 2019
Fetish

Having logged in, you get to the biggest question of all - who are you going to play? It's not like this is a big deal. You can just create your character and be on your way.What's next? Danny Hopkins - Dude with a sister Lydia Onava - Widow waking up in an unknown place Claude Rogers - On his way to visit his Aunt Henry Wells - Protesting H20 What's next...

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Intruded and Blackmailed

by hosiery_cumslut on Sep 16, 2017
Transsexuals & Crossdressers

It all began this one summer, a few months after I turned 19. I had just finished my first year of university in a small "university town", as they call it. I signed a house lease with 3 other friends for the next school year, and we had to pay rent for the four months of summer even if we weren't going to live there. My three friends had all left for home...

Dutiful Assistant

by Jagvillhem on Sep 28, 2019
Transsexual

((There might be some changes throughout the chapters. This is because I am finding out the way I like to write. I'm learning different styles and quirks. Because of this, chapters might differ in style from time to time. This is definitely a trail and error kind of thing, chapters might have changed once you re-read them, this is because I might have gone b...

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A Day at the Beach

by Danielle987 on Sep 16, 2017
Transsexuals & Crossdressers

Bit of background to understand the context. I am Danielle, I am 18, very petite 5" 8 65kg and have long blonde hair. I have been a crossdresser since I was 12. Australia, it was the middle of summer as I was driving to my friend Kate's house. We had planned to go to the beach as I became more brave in my crossdressing adventures. Kate was the same age as...

Becoming a Sissy Maid & Slut Vol. 10

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Seventeen: It's time that Chantel Earned Her Keep. Well it's the morning of a Saturday, to where by night time I will soon be doing some true sissy slut street walking and now truly begin to earn my keep and begin to earn some serious money for my Master. I awake like all other mornings at 7:30am and follow my morning routine, enema, shower, shave...

Master's Degree in Crossdressing Ch. 02

by wifetoy on Sep 16, 2017
Transsexuals & Crossdressers

This confession is the second chapter of a follow up series to my earlier series "College Crossdressing Confessions." My wife forced me to make those confessions detailing my shameful addiction to wearing panties, pantyhose, and other girly intimates, and my panty pilfering ways in college. While I was making those confessions to the public for the first tim...

Adult Bookstore Whoring

by nancyvasquez on Oct 15, 2017
Transsexuals & Crossdressers

Crossdressing sissy Terilyn Bardot arrived at the adult arcade around 6:10 p.m. The city was having some kind of carnival on the waterfront, and so most of the parking spaces were gone. Teri went in and stripped to just a 2 piece bikini and her high heels. She freshened up her hot red Revlon lipstick and greased up her anus with Vaseline. Then she waited. An...

Sissy Constructs for the Manly Man

by _Rinaldo on Nov 16, 2019
Fetish

Alpha males all have an image to uphold. They spend decades, perhaps even their entire lives honing their bodies and personalities to achieve a higher standing in society: to be viewed as the perfect example of what the ideal male should be. Handsome, strong, muscular, confident, etc. The perfect breeding candidate, in essence: desired by all women, and envi...

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