Chastity Crossdressers Stories

18,166 results
Orientation
Length
Source
Infinite Scroll

Sissy Chantel, New Reality Ch. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eleven: Sunday Fun Well now that our Masters and Mistresses have left us here in the locker room, with all twelve of us sissies now freed from our chastity, our sissy dicks are getting quite hard. We have been allowed a period of sissy sexual freedom. For the next 45 or so minutes we are to engage in a sissy orgy to relieve our pent up sexual desire...

One of the Girls

by Erotictales4u on Sep 26, 2017
Transsexuals & Crossdressers

All characters in this story are over 21 years old. This is a fictional fantasy that contains elements of both femdom and the transsexual/cross-dressers niche. This is my first attempt at a story so go easy. ***** I couldn't believe my situation. I had signed up for porn, but I had not signed up for this. I was standing naked in the dressing room and the c...

Dominance Reversal

by Galgo on Sep 13, 2017
Transsexuals & Crossdressers

This is my first story and would like feedback. I have plans to add a lot more to this as a series. Let me know what you think! :) 5:00 AM Cindy was lying in bed next to me. Man does she have an amazing body. It's a shame that she's totally shy and doesn't really appreciate what she has. Once we got married, I talked her into getting breast implants. She h...

Nerves Ch. 02

by Connguy on Sep 14, 2017
Transsexuals & Crossdressers

This is part 2 of my story. Thank You to all who have commented and sent emails, they are much appreciated. Hope you enjoy this next chapter. * I am bound and in a chastity device as I sit here wide eyed at the last statement Tiffany has made. I am caught between fear and excitement watching her ponder what she will do with me over the next four days. A s...

Jolene's Momma Pt. 03

by ValoryG on Sep 14, 2020
Transgender & Crossdressers

(All characters and most locations in this story are completely fictional, with no connection to any persons living or dead.) My wife and I settled down into our new life together. I was now so respectful of her, and appreciated the new Jolene, able to take charge, express her anger when it arose, and generally run things. Like her mother, she really did...

Erika's Story Ch. 05

by Quantarx on Feb 3, 2020
Transgender & Crossdressers

This is the fifth segment of the Erika story, if you would like to know how we got to this point please go back and read the other chapters. Also I appreciate feedback, comments, and a 5 star rating is appreciated if you think the story warrants it. *************************** I awoke late in the morning, nearer to noon to find myself curled up next to Mar...

Jerry becomes Jill Pt. 05: July 4th

by gasissynora on Apr 27, 2020
Transgender & Crossdressers

Jerry becomes Jill: Part 5: July 4th Week End This is the fifth part of my story about how I became Jill. After having started female hormones, Jill is introduced to group play by Mistress Rikki. The Fourth of July is on Monday and that Thursday evening at dinner Mistress gives me some information about the holiday weekend. She says, "Tomorrow you are done...

Erika's Story Ch. 06

by Quantarx on Mar 2, 2020
Transgender & Crossdressers

This is the sixth segment of the Erika story, if you would like to know how we got to this point please go back and read the other chapters. Also I appreciate feedback, comments, and a 5 star rating is appreciated if you think the story warrants it. *** I slept like a baby that night, I think I was worn out from all the excitement of the day before. Mary h...

Sissy Life Pt. 04

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

I stood to attention on my 'sissy spot', the small 'x' drawn on the floor of my Mistress' study. My spot faces the desk behind which is a large leather chair. It is here that I was told I would be placed in chastity. It was here on my spot that events unfolded leading me to serve my Mistress' lover Tony. I was understandably nervous about being stood here ag...

Letter from Lythgoe Heights

by justincbenedict on Mar 7, 2018
Transsexuals & Crossdressers

Dear Shoeblossom: I want to tell you about my male master, Emil. He is Austrian, and although I am, I think a heterosexual male, not really bisexual, or maybe a bit now... But Emil is a find! Just this morning I was being tutored in how to edge without cumming. When I got close, kneeling in front of Emil, he reached down and tweaked the mousetrap on my ri...