Sissy Black Master Stories

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AliExpress and Sissy Downfall Pt. 05

by His_fag_wife on Feb 6, 2018
Transsexuals & Crossdressers

Charlie was deep in it now, being assessed by Miss Bell the beautician before she started work on removing all of Charlies hair below her soon to be plucked eye line. Candice the young pretty petite receptionist was also looking on to deepen Charlies humiliation. "Miss Bell, I'm really tight, but even my little pussy couldn't be satisfied by that little cli...

AliExpress and Sissy Downfall Pt. 03

by His_fag_wife on Nov 2, 2017
Transsexuals & Crossdressers

Tim cupped Emma's arse cheek as they went into the hotel room, stroking her, sliding into the cleft of her cheeks, warming her up a little more, not that she needed it. Charlie didn't notice them come in at all. Not that she could really turn her head with the thick COCKWHORE collar padlocked tightly around her neck. The cords attached to the dildo were als...

Playing Pregnant

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

I'm a sissy. I used to be a femboi, then I was a crossdresser, and now I'm a sissy. The main difference between the crossdresser and sissy phases was the attitude; before I was a guy doing this for fun and to be admired, sexually – to confuse straight and gay boys alike. But now, as a sissy, I was devoted firstly to my master and love, Noah, and secondly to...

My New Life

by gbr2004 on Jun 1, 2020
Fetish

This story is totally fictional and involves forced fem, discipline, interracial sex, among other kinks. Kind of a long story with probably too much dialogue and not enough sex but I hope you enjoy it. *** I'm not going to take any more shit from this asshole. I'm talking about my stepfather. Sure, he's nice when Mom is around but when she isn't here, he t...

Young Sissy Ch. 02

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

I was walking in a field, the cool grass crushed softly between my toes, the sun warm on my skin, the smells of spring were in the air and every deep breath I took filled my lungs with the promise of a fresh start and new hope. The sky was a flawless blue and looked clear enough to take a swim in. Everywhere I turned, all I could see was endless rows of roll...

Jesse's Journey Down a Rabbit Hole Ch. 04

by sadkins116 on Sep 19, 2017
Illustrated

As I mentioned in the previous chapters, this story is a collaborative effort between me and Rebeccsm. She has provided the art, and a lot of the plot, god I love how her mind works, and me for the text. Please let us know how you feel about our efforts. Comments and votes are welcome. It is the only way we will know if you like our work. I would like to th...

March Madness Ch. 09b

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

My Mistress Ch. 03

by Kandy5647 on Sep 12, 2017
BDSM

Hello Peoples of Literotica! It's Drew Nelson again! And I'm back in full force! This time I'm here to not only tell you about my stunningly gorgeous Mistress Tameka. But! I'm here to tell you about my new Master Quentin Devonté Sterling as well. My God what a man he is! Wait! What am I saying?! He's a pure bred God! He's this 6'6, 210lbs, dark brown eyed,...

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

Sissy's Special Night

by mdw_dark_angel on Sep 17, 2017
BDSM

This girl was so excited as Master had agreed to a special surprise for sissy from angel. Master took sissy to work and came right away to fetch angel to return Home and ready things for angel's surprise..."Sissy's Special Night". Y/you see, this slave has belonged to Master... though one has not always retained one's physical collar... since Master first c...