Crossdressers Chastity Stories

18,166 results
Orientation
Length
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Infinite Scroll

End Scene

by felicia_rene on Sep 28, 2020
Transgender & Crossdressers

This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy Description: When a rich wife discovers that her husband married her for her money and to add insult he turned out to be gay. ROLL CAMERA My rich wife had me over a barrel after finding out about my affair with my handsome boy toy assistant. She took a...

Helen Ch. 09

by Philippasubmaid on May 2, 2018
Transsexuals & Crossdressers

This story is a graphic tale of a Dom and his very submissive transgendered male. If you are offended by tales of BDSM and sex between consenting adults then read no further ......... other wise enjoy It is best if read with previous chapters. Feel free to leave honest comments or suggestions, it really does encourage those of us who write to continue......

Sissy Maid to Be... Ch. 03

by missjennymaid on Apr 8, 2019
Transgender & Crossdressers

I would recommend reading the first chapters to get to up to speed on the story, but if you want to start in the middle... Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife. Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves. Jere...

Panty Boy Diaries: Entry 03

by _pdy_ on Apr 3, 2019
Transgender & Crossdressers

Does she know? Can she tell that I just got fucked? She must be able to smell the sex on me, right? My mind is racing as I sit here in this Uber on my way back home so that I can make it to my dinner with friends on time. The driver is a nice, middle-aged woman who's doing her best to be nice and polite. She asked me to sit in the front seat as she feels mor...

A Week End with Mistress Pt. 03

by gasissynora on Nov 6, 2018
Transgender & Crossdressers

Dear readers this is part 3 of my first story and I hope you enjoy it. Your comments and suggests will be most helpful. I am planning on continuing the story if the feedback is positive. ***** Once we are on the way I feel a wonderful vibration in my ass. I then realize that the device Mistress inserted in my ass is remotely controlled. I sit back and enjo...

An Expensive Addiction Ch. 03

by NeverGuessWhatsNext on Sep 16, 2017
Transsexuals & Crossdressers

The Friday after my second encounter with English was just as eventful as I had thought it would be. My girlfriend got to town, and since we hadn't seen each other in weeks, she was hornier than hell. I picked her up from her parents house around 5 and we went straight back to my place to have sex before going to the party. A couple of months after we starte...

My First Time Sucking Cock Pt. 04

by katiecdsub on Sep 16, 2017
Transsexuals & Crossdressers

Teen (18) has sex with older man. He was still sleeping on his back and I was enjoying the silky feel of his wife's negligee that I slept in and was still wearing. It did make me feel submissive and girly. As I laid there admiring his hard body, I noticed the outline of his almost hard cock under the sheets!! Passion swept over my body as I quietly put my...

The Roommate Pt. 13 - Miranda

by ValoryG on Sep 19, 2017
Transsexuals & Crossdressers

Lori left the bed before Leigh Ann woke up from her nap, and Lori again wished she wasn't wearing chastity. If only she could defeat it like before! But having to laboriously dial through 999 combinations on the tiny lock didn't appeal to her (although a hacksaw would probably do the job in a crude way). And so, still horny after the session with her new r...

Uncovering the Sissy Beneath Pt. 04

by jefferyscott745 on Jul 10, 2019
Transgender & Crossdressers

Disclaimer: This story contains extreme fetishes including BDSM and forced seduction. It is also purely fictional. This is part four of my previous work. Be sure to read parts 1-3 if you wish to understand the background of this section. After we reach the bottom of the stairs, Madam Victoria leads us back into the cell. She locks the sliding bars, and b...

The Cage Pt. 02

by FiveDots on Sep 15, 2017
Transsexuals & Crossdressers

Kassi never did tell me how she shrank me. I knew why, I had let it leak that I would betray her. I didn't deserve her, that's clear, but I didn't deserve this, trapped like this, broken like this. I used to think that at least. But if you keep saying it out loud... how much you love her... and you keep pretending... obeying her every command... it just get...