Sissy Castrated Stories

7,169 results
Orientation
Length
Source
Infinite Scroll

Sissy and Wimp

by 1Gratiano on Jul 14, 2020
Transgender & Crossdressers

1 Now the common belief is that any man who wants to wear women's clothes is gay, and that the heterosexual crossdressers who claim to be straight but "just like the feel" of silk panties and so forth, are being, well, less than candid. Be that as it may, heterosexual and homosexual crossdressers are in fact distinct psychological types. To be sure, ther...

Maria's Sissy Boy

by blaud on Sep 11, 2017
BDSM

A princess housewife finds it useful in many ways to have a sissy house boy in her home. But the husband insists on a precautionary measure. Before Maria came into my life, I was just drifting. I was a West Texas slut boy, whose sole purpose in life was to find the next cock to suck. I'd seen her around the apartment complex, but had no interaction till tha...

Miss Annabelle Ch. 02

by Timewarp10 on Oct 16, 2018
BDSM

As Annabelle's first term at University drew to a close, I had become her slave: cleaning floors, laundry, ironing, cleaning her shoes, making her bed, sorting her clothes and other household chores. Each day was filled nonstop with toil, from early morning to late night, stopping only when she had gone to bed to sleep, and even then I would have to be alert...

Feminizing First Step Ch. 07

by antares34 on Aug 24, 2020
Transgender & Crossdressers

I was meeting my internet "daddy" for the first time today. His last text message to me had been very clear: tie myself to the motel bed and wait for him to arrive. I stared at the antique bed with its black metal frame and headboard, wondering to myself if this was such a good idea. This rundown motel had been hard enough to find. I had never been to this...

Humiliation Journey Never Ends

by Subkoksukr4u on Jun 25, 2019
Transgender & Crossdressers

Here I am once again looking up into the eyes of my tormentor, my superior in every way, especially his cock, 10 1/2 inches to be exact. I know because when I first met him he made me measure it with a ruler. He made me measure mine too. I was embarrassed, humiliated and shamed for being so small. It hasn't been called a penis or anything remotely masculin...

Family Chastity Story Ch. 03

by antares34 on Jul 30, 2019
BDSM

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. ***** My gimp son and I have settled into a routine. Permanent chastity with monthly releases. These releases occur on the first day of every month. I...

For Marion's Pleasure Ch. 03

by MarionsPuppy on Dec 3, 2017
Fetish

"Crawl over to us puppy. As you can see, your Master is having a post-coitus snooze. He has fucked me wonderfully as usual, as you never could, and his ejaculation is starting to ooze from Mummy's cunt lips. I need you to be a good clean up boy and swallow all his jism before it drips onto the sofa. That's it pet, long slow licks from my ass all the way up t...

Becoming a Sissy Maid & Slut Vol. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Title: How I became a Sissy Maid and Slut for a Dominant Master. Preface: I would like to begin by thanking all who will read my story here. This is a sissy story based on many thoughts I have imagined, many times throughout my life. These erotic thoughts have been enjoyed for a long while in my life. Like many sissy girls, stories like the one I will wri...

Cuckolding Sindy Ch. 02

by SindySuxALot on Sep 13, 2017
BDSM

Sindy listened intently over the intercom as Lucy was in the other room with her dates. The moans and groans were constant as her Mistress orgasmed repeatedly. It always turned Sindy on immensely to hear her Mistress with other lovers. She sat in front of the computer with her largest vibrating plug inserted in her ass and watched the sissy on the computer m...

Miss A's New Play Thing Pt. 04

by Pornenthusiest on Mar 2, 2020
BDSM

Recap: Miss A had just finished a luxurious bubble bath and was returning to her slave who was chastised and gagged with her pantie hose and a ball gag, with Miss A's wetted panties draped over his nose. Locked away in her dungeon, after an arduous breath control play session, her slave was spread wide at the ankles with a spreader bar, bent at the waist wi...