Black Owned Sissy Stories

198,936 results
Orientation
Length
Source
Infinite Scroll

Cell Block Sissy

by nancyvasquez on Sep 14, 2017
Transsexuals & Crossdressers

I was in the cell with Jose. I was getting ready for lights out and I had just showered and was only wearing a white, wrap around shorty towel. He was sitting on the toilet bowl naked, he was masturbating. "Kevin, give me a blow job", he said. I kept saying "no" and telling him to quit, but he was so persistent. He kept begging me so finally I agreed, on hi...

Mistress Kate Pt. 02

by corduroysissy on Mar 7, 2018
Transsexuals & Crossdressers

When he arrived home from Regan O'Reilly's office Jordan was still in a daze. He needed a drink, no scratch that, he needed a bottle. In a matter of a couple hours he'd gone from having his life threatened, to getting a blowjob from the Leprechaun, to being ordered into sissy sexual servitude by Mistress Kate. She was actually expecting him to be her fucking...

Being a Sissy for Viv Ch. 06

by Caron on Oct 31, 2017
Transsexuals & Crossdressers

Lunch was a pleasant time. I'd prepared and served the food, but we had sat together in the lounge. The blinds down against the weather and prying eyes. The time had felt much closer to friends chatting over lunch than the Mistress-sissy relationship of our previous time together. Viv probed gently about my desires. Intently interested in where and how I had...

Appointment by Card Only Ch. 02

by Sputnik57 on Sep 17, 2017
BDSM

Madam Ruth was more than pleased with her days work as she descended to the bed and stroked the soft white body of the helpless sissy, Poppy mustering a whimper as the dominant Madam. Cupped the soft pink scrotum and gently worked the dainty cock to an erection; she was scared but the surreal situation along with the gentle warmth of the two females, combine...

Cream Puff Ch. 03

by RubixStu on Mar 25, 2019
BDSM

I was naked except for my wig, my makeup, my stockings and my heels. I sat on Roger's lap, his erect cock deep inside my ass. He was watching a nature program. My legs were spread and his arm was wrapped around me while his hand lazily toyed with my little boy parts. He wasn't fucking me, he was simply impaling me, filling me with his masculinity while I rev...

Fantasy to Reality

by CuckoldDesires on Sep 15, 2017
Transsexuals & Crossdressers

I faded in and out of consciousness. My body was numb and I waded through a sea of words and images that filled my mind, struggling to focus on anything specific. Slowly I began to wake but my eyes did not open and my body remained numb. I searched for my memory, I knew it was there but I couldn't reach it, I was entranced. My name and past eluded me as I s...

The Society Ch. 04

by Barno on Sep 13, 2017
Transsexuals & Crossdressers

I have a little explaining and an apology to make. The last installment of The Society, called The Society part 4 was uploaded by mistake. If you are following this story you will find that the first part of this installment is very similar to part 4. Please take this story for what it is, parts 1 through 3 and then followed by this installment, part 5. Sorr...

Second Meeting with Master Gene

by sissysubTiffany on Jun 19, 2018
Transsexuals & Crossdressers

Friday evening comes finally as this was the slowest week of my life waiting for this day to get here as so looking forward to tonight even though I am still a little leery about becoming a sissy submissive of Master Gene's. I have shaved my entire body and sent pictures for proof as he demanded and now sitting in a pair of my pink with lavender lace bikini...

Taken Too Far Pt. 02

by SwitchSissy on Mar 10, 2020
Transgender & Crossdressers

"Good girl" He smiled in approval. "Now, I noticed something earlier, when I was clicking that new, secure padlock onto your clitty" he reminded me, pulling me up so I was now sat on the bed, my arms bound behind my back with duct tape. "You've written something there, and on your thighs. And I think I can also see something on your belly button too, you lit...

Demanding Satisfaction Ch. 1

by kyriele on Sep 15, 2017
Fetish

Austin came home on Friday... like every other Friday. My kids were ready to go to their father's house and I told him to take them. The house would be empty and I could no longer wait to extract... revenge? No... too strong a word. Satisfaction. Now there was a word to describe the myriad of thoughts running through my brain. I had gone on the computer an...