Erotic Story, Crossdresser Puts You In Chastity Stories

371,137 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Secret Journey Ch. 02

by DrGonzo124 on Feb 11, 2019
Transgender & Crossdressers

AN: with profound thanks to Personal Deviant. 8 9 8 Suki dreamed of another time and place. A place filled with warriors drinking... feasting...fucking. Another body? His, yet not his own, to judge by the nipple clamps pinching him with a painfully arousing agony and the odd sensation along the length of his erect shaft that had to be a lattice of pie...

From a Husband to a Dutiful Sissy Ch. 02

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Two: My reveal, a true reveal for the sissy in me. I reach to the bottom of the stairs and at the front doorway entrance, Helen and Jenny are standing and looking at me in my black maids dress, white tights, black velvet 5 inch spike heel pumps, wig and makeup. The look on their faces seeing me dressed as such is priceless. This is the first time He...

A Wife A Little To Understanding

by felicia_rene on Oct 12, 2020
Transgender & Crossdressers

Present day: We arrived at the 'Sissy Salon' which was a covert sex club for downlow gay wealthy men and lesbians. As his agent and pimp I collected all his performance fees. I walked into the 'Sissy Salon' to make sure that everything was in place so my sissy husband could perform. Then I went to his dressing room to make sure everything I requested for me...

Ms. Alexandria - Interview No. 02 Pt. 01

by gasissynora on Nov 4, 2019
Transgender & Crossdressers

This is the second part of the Ms. Alexandria series. I believe it will stand alone, but will make more sense if you read the first part of the story, "Ms. Alexandria: The Interview." * Ms. Alexandria: The Second Interview -- A day out. Part 1 I get home from the interview, feeling that it went very well. I am also extremely horny so I strip down to my li...

Her Surprise

by dickital on Sep 16, 2017
Sci-Fi & Fantasy

The bell jingles as the door opens, the toys outside were enticing, but the store inside opens your eyes. Though it is a small shop, it manages to cater for as many different fetishes as you could imagine. One wall is dedicated for the ass, dildos, inflateable, lockable, ejaculating, big ones, small ones, tentacle which move on their own. Two walls are dedic...

Uncovering the Sissy Beneath Pt. 03

by jefferyscott745 on Jun 25, 2019
Transgender & Crossdressers

Disclaimer: This story contains extreme fetishes including BDSM and forced seduction. It is also purely fictional. This is part three of my previous work. Be sure to read parts one and two if you wish to understand the background of this section. *** I hesitate to follow him out of the bedroom, as my anxiety is out of control. "Have I just been kidnapped...

Caught crossdressed

by Deedeesissyboy07 on Apr 22, 2025

Im home alone as my housemate is away with his girlfriend and not due home until tomorrow so yi am sitting at my dressing table looking at my newest purchase, a chastity cage a very small chastity cage as i wanted it tight, and a vibrating butt plug with a big purple crystal on the end. I've been a closet crossdresser for ever and have a huge collection of c...

Open in Reader

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...

Crossdresser In Picnic Area

by Lovinhose on Sep 13, 2017
Transsexuals & Crossdressers

This is my first attempt at a fictional/fantasy story. All my stories thus far have been true, honest, and accurate, as much so as I can recall. But I kind of ran out of true stories that were worth sharing (for now, but I've got some 'irons in the fire' and hopefully I'll have another true story to share fairly soon). The story I will tell here is something...

Female Erotic Police Squad Pt. 03

by mattpantyhose on Sep 14, 2017
Fetish

Most of the officers of Female Erotic Police Squad enlist in the service to catch criminals. But there are also some who do it for sex. Physical love is the modern way to fight crime, but it does not necessarily mean that sex should be considered merely a tool. As long as an officer fulfilled her duties properly there was no reason for her not to take additi...