Sissy Boss Stories

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Orientation
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Infinite Scroll

Sissy Lauren Pt. 02

by CdJade on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Two: A New Girl It was the first day of February and almost six months into Freddie's jail sentence. Or at least it would be if Freddie still existed. On his second week inside, Freddie had been transformed into sissy Lauren, the girlfriend of E wing boss, Ronnie. Lauren had now learnt how to apply her make up to the style of most of the instructio...

Opening Him Up Ch. 03

by humbleboy on Sep 12, 2017
BDSM

Amy laid down next to Tim exhausted. “Tim, now I want you to suck on ALL that cum you just shot in my pussy.” Tim without a word placed his mouth on her trimmed pussy and began to suck and lick her hot organ. “That's good. You love this pussy, don't you?” Amy had always liked the way her husband eat her out, but now it was the power trip getting her off. “D...

Moving To Louisiana Ch. 3

by eeric on Sep 14, 2017
Interracial Love

If you have the time you can e-mail me at the email address in my profile and tell me what you thought. * * * * * Over the past weeks Helen has become more open about her love for black men. She has been out to clubs and danced with both Ty and James, although never with both of them together. Then she has had me lick and suck her pussy when she gets home...

Sissy Boy Secretary Ch. 04

by Hotenuf4u on Sep 19, 2017
Fetish

Arriving at the office 15 minutes early, walking past three of the other secretaries, noticing them smiling and giggling when they glanced my way. Elaine must have told them of my secret desire to wear panties. Today's choice was the white lace thong pair, which felt good as they rubbed against me as I walked. Feeling my face turning red, I walked faster to...

Afro Stress Relief Ch. 09

by llts1970 on Feb 3, 2020
Transgender & Crossdressers

After a hectic and traumatic weekend, it was Monday again, I was still in a state of shock after what had happened. I spent most of the day at my desk doing very little, and wondering if any of the loading bay crew had seen the photos of me kissing Drake's ass, but I thought they wouldn't recognize me, as I was fully made-up as a sissy in the picture, but I...

Lexi's Interview

by Jemina004 on Mar 17, 2020
Transgender & Crossdressers

October 5th, 2063 Lexi reached for his purse and took out his compact mirror. Mostly out of nervousness, he had to check his appearance again. Alexandra St. Claire was sitting in the waiting room for Carter Logistics on the 56th floor of the MacArthur Building in Chicago, trying to get one of the most coveted jobs available for white bois these days. Being...

Wife in Control Ch. 06

by wifetoy on Sep 25, 2017
Fetish

I will bring you your Magic Wand and Trigasm. And suck on your toes, while you enjoy every spasm. Your humiliated sissy in panties, tights, and stilettos. This is the sixth chapter of my wife's execution of the punishment poem I submitted to her suggesting ways to atone for my inability to control my orgasm. Please read the earlier chapters for the full...

My New Daddy Ch. 08

by sissytoy20 on Apr 17, 2018
Transsexuals & Crossdressers

I slept in the next day and no one bothered me. The sunlight streamed in through the windows as I got up, bathed and got dressed in a skin-tight black minidress, bra, thong panties, and a pair of slut heels. I did my best with my makeup but I was still critical of my look. I knew enough about makeup to know that I could look so much sexier if I knew what I w...

Black Femdom For Black Sissy

by Samuelx on Sep 11, 2017
Fetish

Sitting comfortably in her basement/dungeon, Ottawa's premier dominatrix Madame Whitley looked at her submissive, Shane Johnson, as the big and tall, formerly masculine Black dude stepped out. Clad in a pink Tutu, blonde wig, crimson pantyhose and high heels, the brother was finally letting out his inner slut. For years, Madame Whitley struggled to help Shan...

Kimmy's Discovery Ch. 03

by Deviana on Sep 16, 2017
Transsexuals & Crossdressers

i heard the click of my .. of Dougie's high heels and it was like everything fell silent. i walked around the kitchen, around and around, wanting to hear that click, to have the sound so deep in my mind. i took one of the VS 120s and then a pretty pink lighter that was on a side table- i have to find one of these for me- and lit the tip, feeling the filter e...