Sissy Game Stories

87,858 results
Orientation
Length
Source
Infinite Scroll

A Tale of Two Bitches

by Lordheed on Sep 12, 2017
BDSM

"Game Over", a deep voice pronounced from the television. Johnny threw down the controller in frustration. 'Can't even win at video games, let alone anything else', he thought to himself in disgust, 'What a way to start winter break'. He'd been home now for 3 days; already missed campus, his dorm room, and the constant business of schoolwork that could keep...

Mistress Shay Noir

by Samuelx on Sep 11, 2017
Group Sex

"Essential services, that's what I provide, like any good businesswoman, I know my clientele and their special needs," I smiled to myself as I read these words on the Temple of Noir website, which advertises my services to the entire world. There are a lot of Black dominatrix types out there but I, Mistress Shay Noir, am the only one catering to the hidden n...

Neighbourhood Terror to Sissy Pt. 02

by Fibaro on Mar 11, 2019
Transgender & Crossdressers

When Mark woke up the next day his parents were already gone, as usual. He was no early riser after all. He made some breakfast, gamed a bit made lunch and went to the skate park. There didn't seem to be any signs that flyers or anything like that had been spread much to his relief. Yesterday had certainly been a scare, maybe it had just been a cruel prank....

Escapism: Nightingale

by chasingrisque on Sep 13, 2017
Transsexuals & Crossdressers

I slobber on the thick, veiny cock in front of me. I slurp away like it's an ice-pop on the hottest day of summer. I'm dressed in a red plaid skirt, a white shirt with a matching plaid badge that reads 'head girl', the neckline just low enough to reveal my leopard print bra. The skirt is riding high enough to reveal the matching thong and floral patterned...

Becoming Mindy Ch. 02

by mindyrose on Sep 18, 2017
Transsexuals & Crossdressers

Thank you for the positive feedback from my first story. As I recall things I wrote about in my diary, I am not going to be writing on all of them. Just the ones that are important to my story and/or just some memorable events (i.e. the first time I..). I hope I am able to write them in a way that you find as enjoyable reading as I had living them. I have se...

A New Life Ch. 02

by sissycinnamonswirl on Sep 18, 2017
Transsexuals & Crossdressers

I closed my eyes and took a breath, which was far from easy. The steel boned corset, which I was made to purchase and learn to lace myself, was quite tight and pulled my body into the curvy shape that both Mistress Sally, and the men who have been encouraged to watch me on Skype, all enjoyed. The cursor moved across the screen as Mistress Sally's Skype call...

Sissy Boy Chuck Becomes Just Sissy

by Krazy35 on Sep 14, 2017
Transsexuals & Crossdressers

A long time ago, I realized that I had a thing for women's clothing. I used to sneak into my sister, Jessica's room and get all dolled up in her clothes. She was a year older than me, but we were practically the same size. I got an incredible hard-on looking at myself in her full length mirror. I quickly undressed, put everything back the way I found it, the...

A Week End with Mistress Pt. 01

by gasissynora on Oct 16, 2018
Transgender & Crossdressers

Dear readers this is my first story and I hope you enjoy it. Your comments and suggests will be most helpful. I am planning on continuing the story if the feedback is positive. This story is based in part on facts and part on fiction. I will leave it to the reader to decide which is which. ***** We had just finished dinner and I was in the den getting rea...

The Prostate Exam Pt. 07

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

Please do not read on unless extreme sissification and forced gay and bi scenes, watersports and cum eating, really flick your switches. I don't want to offend anyone so thought this comment might help. ***** It'd all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by pushing bac...

Spanking Night Ch. 04

by Angelscuck on Sep 14, 2017
BDSM

I slowly rolled over to allow my wife access to my bare bottom. I was still in shock, my mind reeling from what she had just confessed to me. This was no mind game. I had the proof-positive taste still lingering in my mouth. Smack. Suddenly the sound and sting of the cane against my skin brought me back to reality. It hurt like hell! I didn't cry out but I...