Sissyboy Stories

140 results
Orientation
Length
Source
Infinite Scroll

Casey's Submissive Journey Pt. 05

by corduroysissy on Feb 7, 2018
Transsexuals & Crossdressers

Homo Hubby Night – Part One Note: In this continuing saga, Casey (Debbie) & Jamie (Angie) are closet crossdressers who are submissive to their wives Karen & Audrey (respectively), however in this section of the story there is no cross-dressing. Their wives are humiliating them by making the boys put on a homosexual sex show for their amusement. *...

Steve to Stevie to ?? Ch. 09

by gbr2004 on Sep 19, 2017
Fetish

Steve had a very bad trip back to her apartment. First it was the black cop who stopped him and used him like his bitch. And, then before he understands all the implication, he has promised to be a sissy whore for him. Then the vice detective who has decided that he will make Steve suffer if he can't control himself and not be a whore. Then, so much worse at...

Birthday Breaking

by purekink on Sep 19, 2017
Transsexuals & Crossdressers

I had no idea what my girlfriend had planned for me that day - and if I did, I'd probably still have gone along with it. My birthday wasn't that special an occasion for me. I had no family and having recently moved, I'd no real friends in the city. But Gen was determined to give me a time to remember, and said she'd arranged a small gathering with her frien...

Sandra and Stevie Ch. 66

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the sixty-sixth installment in a series entitled "Sandra and Stevie". If you have not read the previous sixty-five episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I stro...

Porn Shop with Gloryholes Ch. 01

by Sinful_whispers on Sep 14, 2017
Fetish

Chapter 1: Her 1st experience w/ Gloryholes The darkness of the night was settling in as she parked her car, exited it, and began walking across the parking lot. The black macadam was empty, all but two cars and one was her second shift employee Dave. The night lamp lights began to flicker on and off then popped on fully as she reached out and curled her fi...

Steve to Stevie to ?? Ch. 06b

by gbr2004 on Sep 15, 2017
Fetish

April grabs my arm helping me down the stairs, the heels hard to handle going down the steps. Then she leads me into the library, the lights are dimmed but see Mistress sitting in her chair. Then as I look around, I see four other days in the room. All are dressed very erotically, and are all very stunning. I stop, stunned that strangers are seeing me dresse...

Carol, Candy & the Ex Pt. 02

by corduroysissy on Mar 26, 2019
Transgender & Crossdressers

(Will Candy make a good cuck?) Davie was standing at Carol's front door dressed in a pair of copper brown wide-wale corduroy dress trousers, and a beige polo shirt. Oddly enough, he felt more nervous than he did the night before when he was in full drag, and he attributed it to the ex-factor. Last night Davie as "Debbie" was there to meet Robbie as "Candy"...

Sandra and Stevie Ch. 32

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the thirty-second installment in a series entitled "Sandra and Stevie". If you have not read the previous thirty-one episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I st...

Sucker Boys

by TopsyBFox on Sep 13, 2017
BDSM

We meet in a bar, me, my best sissyboy painslut & you. We are all dressed in everyday office attire; you boys look so professional in your suits. I have on a tight white blouse which strains a little at the buttons, the sheer lace of my bra clearly showing through; a straight black skirt, net stockings & heeled patent black pumps. There are other such groups...

Steve to Stevie to ?? Ch. 07

by gbr2004 on Sep 13, 2017
Fetish

I had returned to work after my first nite with Ms Storm. The night she turned me from a young man to her slave. Ms Storm had came to my work place and had talked to my boss for a long time but I don't know what she told her but my boss, Ms Hunter, had talked to me like never before. Then I had been ordered to return to Ms Storm's house that night. Upon arri...