Crossdressed Stories

155 results
Orientation
Length
Source
Infinite Scroll

White Gurl and Her Black Man

by Folkestone on Mar 26, 2019
Transgender & Crossdressers

Well this is something I never expected. Here I am in a gay resort in the Canary Islands, can't remember what it's called, with a man, a black man. I am effectively his woman and my raison d'etre is to pleasure him. Well, he has paid to bring me here and bought me clothes to wear, not that he asked or that they were anything I would have chosen for myself b...

Monica's Mixed Bag

by MonicaMax on Aug 30, 2017
Transsexuals & Crossdressers

I have crossdressed in private since I was a young child. It all started with my mom's nylons and went downhill from there. Now, as a married guy who leads an otherwise straight, boring life, it's super exciting to dress up and occasionally hook up on the DL, taking on a submissive role and letting a guy have his way with my body. Because I lead a straight,...

Sissyhood of Travelling Panties Ch. 03

by daddyslittlebitch on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 3: Carl Blake's mind could not shake the image of the pair of sexy red panties hidden in his room. As he ran down the stairs to answer his mom's call that Carl, his best friend, was here, all he could think about was the sensual scarlet satin of the boyshort panties with their red lace details. His mind could not help dwelling on how he had rubbed h...

Chance Meeting on eBay of All Place

by Leighharding on Sep 16, 2017
Transsexuals & Crossdressers

This is a true story of a chance meeting which has turned out to be really rather amazing and surprising. ***** I was trolling eBay for some underwear to buy when I happened on a rather large lady selling some used kit. I messaged her to ask specific sizes and she responded straight away asking if it was for me. Normally I would deny that I was buying...

Interactive Crossdresser...Dare Me Ch. 03

by PorscheKaru on Sep 16, 2017
Transsexuals & Crossdressers

Hi again, I'm back to share a couple quick dares, I still wish you all would send me more dares. This first one is from Jason. This is from an email he sent me. "You're first dare will be a simple easy one that im sure you can handle ;) I simply want you to wear the shortest skirt you own, next you will go out to a public place and just sit across from ei...

The Hermaphrodite's Curse Ch. 10

by Cleophila on Sep 12, 2017
Novels and Novellas

PART TWO - CAMBRIDGE - 3 - "What do you know about Hermaphroditus in graeco-roman mythology?" Professor Cavendish asked. "I know the poem," Saphy replied, quoting, "'Lift up thy lips, turn round, look back for love, blind love that comes by night and casts out rest.' 'To what strange end hath some strange god made fair the double blossom of two fruitless...

Birthday Mummification

by Ropesonme on Sep 12, 2017
BDSM

She smoothed the cellophane tightly and smoothly over the hand lightly gripping the rubber ball and up to the elbow. She had covered it with several layers already, and it was already difficult to make out the fingers through the plastic. With a grin of satisfaction, she put the cellophane down and reached for the pink duct tape. In short order, the hand was...

Smoking With Friends Ch. 01

by jjww100 on Sep 16, 2017
Transsexuals & Crossdressers

The phone on my nightstand rang and I groaned as I grabbed it and looked at who was calling. It was Benny and I answered it. "Hello". "Yo Justin, I got $250 worth a weed! You need to come pick us up so we can smoke it!" "Just Wait. Who are you with?" "I'm chilling at McDonald's with Matt and Vic." "Okay, I'll be there in twenty minutes." I hung up, qui...

CrossDressed and Creampied

by Tara40 on Sep 12, 2017
Transsexuals & Crossdressers

My wife and I have had a strong and open relationship from the start. We have accepted each other and all our wild passions, and we have always been open about our sexual desires. Having said this I will try to express what happened the other night with the same intensity I experienced. I came home from work and saw Tara's car in the drive. Strange; she g...

Lady In The House Ch. 01

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

How had it come to this? I was dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail. How had a mild mannered, and diminutive but highly successful accountant in his 30s ended up in one the States high security prison? Well it had a lo...