Sissy Stars Swallow Stories

86,474 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Claire's New Start

by Sissyhalo on Mar 21, 2018
Transsexuals & Crossdressers

There's the thick taste of cum in my mouth and my bum has that feeling of being fucked...filled...made love to and last night replays in my sleep along with everything that has found a home in my head. ...Stop lying, start loving that cock inside you. ...You've never been man enough but you can be sissy enough. ...Worship cock like a good sissy girl. ......

Seductress & Daemon: Sissy Pt. 02

by SeducedKnight on Sep 15, 2017
BDSM

********** A continuation of my initial story, the next morning... ~~~~~~~~~~ Zombe: a black rubber o-ring type bracelet worn locally, either on wrists or ankles (or both in my case, I have an oversized one that I wear as a necklace too). ********** I wake early the next morning, Seductress and the sissy are still asleep, the sissy and I are snuggled in...

Tara's Training Ch. 02

by cumlover10 on Nov 18, 2019
Fetish

"Don't you dare wipe that cum off your face, but I want you to clean up your asshole and make your slutty panties look good again." Tara started to walk out of the room before she turned back and paused before asking one question, "are you sure you want to be my little cumslut tonight?" My heart was pounding, fresh cum still overwhelming my nostrils and tast...

Another Submissive Slut Ch. 11

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

My land lady's knowing look held me transfixed. Quietly Mrs. Lehrer purred, "What are you?" A spasm of trembling shook my body before I could mew out, "I am a sub sissy slut, Mrs. Lehrer." "Hemmmmm," She hummed, "And what else are you slut?" Her voice was quiet, soothing, inquiring. "I am a wanton cum whore, Mrs. Lehrer," I admitted, blushing at such an a...

Katelyn's New Sissy Pt. 01

by bluesbirds on Dec 25, 2018
Transgender & Crossdressers

I remember she made me try the Sissy Peni-Pacifier in the store. It was a humiliating day outing, meant as "my" Christmas gift. Dressed up in a tiny bright red sexy elf costume with marabou trim around the edges that ended at my sissy clit, black fishnet stockings and 4" black heels, with a ridiculously large shiny red bow in my hair, surrounded by mirrors a...

Playing The Naughty Schoolgirl

by davidhtm on Aug 18, 2017
Fetish

Full permission is granted to reproduce this work, provided credit is given to the author. The following is an adult story. If you are not 18, you cannot read it. If you are offended by sexually oriented material, stop now. This is my second attempt at writing a story any comments would be appreciated. * * * * * I had been serving Bill and Jane for sever...

My Bestfriend's Girlfriend

by Shauna_Wood on Jul 9, 2019
Transgender & Crossdressers

When I was in my early 20's I used to play a lot of online video games. First person shooters, mostly. The Battlefield series, especially. I had started playing games online with a guy named Chris who had gone to high school with my ex-fiancé. He and I had met through her and had really hit it off. We had remained close even after she and I split. He lived u...

Discounted Carpet

by Leigh_216 on Jul 31, 2019
Transgender & Crossdressers

My name is Leigh. Well my girl name, I am a cross-dresser. I just feel right to me and I guess that is how I am. All my stories are based on truth; but the places and names have been changed. Friday night and I was ready to hits this clubs but I needed to stop at my Aunt's old house on the east side of town first. Long story short: The family was selling it...

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...

The Virgin Tranny & the Bride Ch. 07

by yano on Sep 25, 2017
Transsexuals & Crossdressers

Firstly, on behalf of Roberta and myself may I thank you all very much for your very generous votes. We now continue Roberta's story and it is the morning after and tranny Roberta views the video of her big wedding day before a shopping trip and an exciting public photo call. * * * * * Next morning, I was awoken by a very excited John. "Come and see this...