Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Made to Obey Ch. 13

by madetoobey on Sep 9, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). I'd been forced into a chastity cage and made to start wearing panties all the time. Furthermore, a curious email I'd sent to "Bowser" before I was married led to my past fraudulent activity being unco...

Watching the Detectives

by nikkiesilk on Sep 16, 2017
Transsexuals & Crossdressers

I live for feedback. ***** 1 Philippa For the umpteenth time I needed to move to get my circulation going again. I tried to stretch my legs but it's not easy in the front seat of my small car. Fuck, I thought as I snagged my tights against something beneath the steering wheel. If that was another pair ruined I would scream. I was parked facing a nondescri...

One Fateful Evening Ch. 01-10

by Pippa on Sep 16, 2017
Transsexuals & Crossdressers

Pippa's Story. (Part One.) One Fateful Evening… It all began as a bit of a joke really. We'd all been out clubbing in some really raunchy night-spots and were still high on both the atmosphere and the two Love-doves that we'd swallowed a few hours before. As the night wore on and, as morning was quickly rearing its bright and beautiful he...

Quiet Servitude Pt. 01

by AmandaMI on Sep 15, 2017
Transsexuals & Crossdressers

Author's Notes Before reading this story please be aware that that some people would label this work as obscene and pornographic in nature. It contains several themes including transgendered, homosexual and lesbian issues in addition to graphic sexual descriptions. To make the action flow more freely and the stories light-hearted, I have taken a socially n...

Jamie's Story Ch. 02

by Michael142 on Sep 16, 2017
Fetish

Author's note: This next chapter is the story of Jamie's attempts to explore his sexuality on his own, after Anna. He will also explore Jill's new persona dating Tom and maybe others. There is a lot of sexual activity in this chapter, which may seem excessive or gratuitous to some. It's my belief that there is just as much sex as is necessary to tell the sto...

Mommy Goes Shopping with Me

by JhMcKn on Aug 18, 2017
Fetish

This takes place in late 1949 after WWII had ended. Sheer nylon stockings were worn by women everyday and some held them up with a girdle, some a garter belt, and some with 'roll garters'. No one in the story is under the age of eighteen. It was earlier in the afternoon than I usually got home. I saw Frank's car in the back of the house so I knew he was...

Red Swallow Ch. 05

by BJGoodhead on Apr 20, 2020
Transgender & Crossdressers

After completing "The Diary of Jewel Delacroix" I was approached via E-mail by Rachael Ricci Swede and asked if I would consider writing a story idea she had. After a few emails I was intrigued by her idea and agreed to write it. This is an original story by Barbara Jean Goodhead. Written in collaboration with Ideas and Plot Points by Rachael Ricci Swede....

Afro Stress Relief Ch. 11

by llts1970 on Oct 5, 2020
Transgender & Crossdressers

At work on Monday, things were once again running as usual, no one mentioned the Beer Bust, well almost no one, Mary cornered me when I was getting a coffee. "Would you like to know what I did this weekend?" Mary asked coyly. "Er...yes sure," I answered, trying to sound completely uninterested. "Well, I was recruited by a black pimp! I'm a real prostitute...

Isabella's Reversion Pt. 01

by silverbackteddy on Sep 14, 2017
BDSM

Note from the Author: This is a story about ABDL. The first word being Adult. All sexual encounters center around Adults, above the age of 18. This story also contains BDSM, plushophilia, watersports, and various other fetishes. For those that are grammar freaks, please don't comment on my improper grammar use. I could care less. I do my best with spell an...

Caught in Her Panties Ch. 02

by Knightofround on Sep 16, 2017
Transsexuals & Crossdressers

This is a fictional story as was part one. The content of this story may not appeal to everyone. It includes female domination, crossdressing, strapon, lesbian, gay, and such. Just keep in mind that it is fictional and should not be taken seriously. Otherwise just enjoy the read. ***** It has been almost a month since my wife Mary discovered my secret. She...