Owned Sissy Stories

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Sissy Girl Forever Pt. 01

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

The call from Mistress Andrea made my day. I hadn't seen her for over a week and was looking forward to playing with her & having my chastity finally removed. You should know that Mistress and I have known each other for many years and have I always enjoyed being her sissy sub. Lately she has been training me to be more feminine in appearance. I have been r...

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...

Owned by a Ghetto Bitch Pt. 03

by FantasizeAndRealize on Sep 12, 2017
Fetish

For the next few weeks things stayed pretty much the same with Sholanda. She would meet up with me about thrice a week at my house and demand at least four or five orgasms every time. She slowly grew more dominating and I was happy to let her have her way with me. Eating her creampie had become a regular activity that I had to do every time that I came in...

Sissy Whore Ch. 02

by DebbieDublin on Mar 7, 2018
Transsexuals & Crossdressers

I wrestled with my emotions for the rest of the afternoon, sitting on the sofa trying to distract myself from the mysterious web chat. I'd been at this a long time now and I was used to conversations that went nowhere. Most of the guys that contacted me followed up with a dick pic and were not really capable of continuing the fantasy beyond the scant descrip...

My Sissification Ch. 02

by sissy171 on Aug 31, 2020
BDSM

I had always planned to go to college, but I was already fairly secure in my business, so I entered college with no scholastic trepidation. My way bigger fear was that I was still sporting a bikini tan, which kept me conflicted; fearful of being discovered, constantly on a sexual edge, and woefully missing Beth. The bikini bra outline was her "brand" upon...

Alex, The Closet Sissy

by Areallysissyboy on Feb 11, 2019
Transgender & Crossdressers

My name is Alex, a closet crossdresser. 18 years old, never had a date. Too skinny, too weird, too feminine. I wore my hair long but not a hair on my body tho, not very athletic. Just a 5'3" skinny 125lb pale white boy with long black hair. Who loves dressing like a girl every since my older sister, Sam, moved out 1 years ago which left her old room unsuperv...

Training Aide Ch. 02

by Angelscuck on Sep 16, 2017
BDSM

Mistress Elaine stoop up, causing me to roll off her lap onto the floor. I just lay there naked, sniffling like some little sissy, waiting for my next ordeal. My Mistress then said, "It's a good idea, at this time, to let your slave have a few minutes to recover. It also gives him time to let the realization set in, that he has been totally broken and is...

Neighbourhood Terror to Sissy Pt. 05

by Fibaro on Apr 3, 2019
Transgender & Crossdressers

At least he didn't have to wait long for his bus to pull up. Not that it helped with any of his suffering. He vowed right there that he would never visit that store again. There were few people on the bus and yet he felt like all eyes were on him. Passing two girls his age at front he heard some whispers. "What the fuck, I never thought that store would ever...

Cuckolding Sindy

by SindySuxALot on Sep 13, 2017
Transsexuals & Crossdressers

Domina Lucy Sissy Sindy sat in her room staring at her computer monitor. Her mistress Lucy had ordered her to stay in here and watch gay fisting videos. Her eyes watched the screen as closely as she could since she knew she might be tested on the content later. She was mildly distracted from the video by the huge vibrating plug inside of her sissy pussy. I...

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...