Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Slave Ch. 11

by slaveheathen on Sep 25, 2017
Fetish

SLAVE Note: I have no idea if a resort like the one in this chapter actually exists, but damn I'd love to go if it did! If you haven't read the previous chapters, I'd suggest you do, as it would help to understand the characters better. This story is about a bisexual man who has completely submitted to his Mistress. It contains scenes where he has sex with...

Cunt! Ch. 04

by chandler831 on Sep 19, 2017
Transsexuals & Crossdressers

After our fun in the kitchen, Derek stayed and made himself breakfast and I headed upstairs to get ready for the day. I pulled out all of my clothes from duffel bag and laid them out on top of my comforter. I had so much new clothing! I decided on wearing a thong this time as I had yet to wear one out besides the brief moment trying it on when it arrived in...

Friday Night Snow Storm

by WhiskeyIsGood on Sep 26, 2017
Transsexuals & Crossdressers

It was late, nearly midnight on a freezing Friday night, in the middle of February when I found myself driving into an absolutely blinding snowstorm. After listening to the weather reports on the radio all day, I was certain I could beat the storm home. They had said it wasn't supposed to get this bad for hours yet, long after I would have been safely at hom...

How Nathan became Natalie Ch. 01

by saintlycd on Nov 22, 2017
Transsexuals & Crossdressers

My name is Natalie but that was not the name I was born with; rather it's the name my wife gave me when she made me her "sister" and her cuckold sissy not long after we were married. My real name is Nathan but that's a name I would prefer never to use again because I enjoy being Natalie much more than I ever enjoyed being Nathan. This is a story of how my wi...

A Dirty Little Theory

by bigrusker on Jul 30, 2019
Transgender & Crossdressers

I have a theory. Or maybe I'm just trying to justify how it came about, but for now let's call it a theory and stick with that. Capiche? Excellent. Glad you're on board. Now, as I said, I have a theory, and it goes something like this: if you marry someone that's of a similar size, eventually you end up wearing their clothes. I think most of the time it ha...

What's Your Price?

by Checkmate215 on Sep 26, 2017
Transsexuals & Crossdressers

Growing up poor meant I always had to do without. I was orphaned as a baby and became a ward of the state. I could never seem to catch a break, my life was one loss after another. After becoming 18 I was discharged from foster care with nothing. Now three years later I still had nothing. My prospects weren't good and I couldn't get by on my looks. I was 5'7"...

From a Husband to a Dutiful Sissy Ch. 11

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

The way this chapter turns out to be, I suggest one may need some tissues... Don't say I didn't warn you. ***** Chapter Eleven: Jack and Chantel, Life's Ups and Downs. I wake up to another new and exciting morning, It's cold out but sunny, Fall is soon moving to Winter. Out of my nightie and into the shower I am invigorated by the warm water. Getting out...

Becoming a Sissy Maid & Slut Vol. 02

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Four: My Arrival and a New Start to Full Time Sissy Life. I awake about 7:30am, groggy as I only had a floor to sleep on with a thin blanket, I rub my morning eyes as I sit up and see the black, satin, maids dress on a hanger, as if it was calling me to put it on. I soon realize my new predicament and smile. I had to take off the pair of pantyhose,...

Walk of Shame

by lululuvsblack on Sep 16, 2017
Transsexuals & Crossdressers

She should have been mad. She should have thrown me out there and then. Instead my wife was disturbingly calm and reasoned. She was going to be worse than angry, she was going to get even. She was going to make sure I got what was coming to me for sleeping with that cute piece of ebony ass and that I would truly regret it. Although we were white, we lived r...

High School Reunion

by phoenixcinders on Sep 18, 2018
Transsexuals & Crossdressers

All characters are over the age of 18. *** Finally walking off the plane from my first class seat on a Thursday evening. It feels good to be home. I'm back in town for my 10-year high school reunion. This time I'm going to be the one everyone's jealous of. I've got the perfect job, making more money than I know what to do with. Well... being an accountant...