Perm Sissy Stories

6,783 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

Weekend Games Ch. 03

by SissyAndi on Sep 16, 2017
Transsexuals & Crossdressers

Disclaimer: My stories contain explicit descriptions of consensual and Non-Consensual sexual activities and are not suitable for reading by anyone under the age of 18, or anyone offended by reading such material. These acts include bisexual activity, cross-dressing and other fetishes and perversions. All characters and events are complete and total fiction a...

Ears and Brows

by FindingGail on Jul 17, 2019
Transgender & Crossdressers

Our summer long vacation trip was over and it was time to head home. We had been traveling across the country for four months – just the two of us learning and discovering. By this time I was very comfortable in my new persona as Gail. I was trying to establish my style as a woman. I had no guy clothing as my wife had trashed everything I brought with me – k...

Transforming Brent Pt. 03

by sissymissyct on Oct 8, 2019
Fetish

Over the next few days I removed most of my male clothing from the house and donated it to Goodwill. I met Wendy as she got out of work each day and we went shopping. The first time was for regular clothing. Skirts, dresses and blouses, leggings and shoes and regular lady's sportswear. Thursday it was lingerie night. I ended up with multiple bras and camiso...

Wet Dream Pt. 03

by sissymissyct on Jan 28, 2020
Fetish

Gayle finished ordering items on line and checked the cam to be sure Georgia was asleep. The wetness in her panties told her what she needed to do. The payback for all those years that bastard cheated on her and how he had no idea what was coming to him, just made her pussy so wet. She was soon in bed enjoying her favorite toy. "I can't believe I slept so l...

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. 04

by His_fag_wife on Dec 30, 2017
Transsexuals & Crossdressers

As Tim added inch after inch, slowly taking his time, stretching his new slut, driving deep into Emma's tight twitching arse, she moaned with the pain like a wounded animal. He loved the supremely tight fit as he slid forward into her, bit by bit. His sweaty ball sack finally rested on Charlies face, each of his big balls settling into Charlies eyes sockets...

You Can Always Say No Ch. 06

by AngelCherysse on Sep 25, 2017
Transsexuals & Crossdressers

We pulled up in front of the professional building opposite the sprawling medical center. The intervening multi-story parking structure was well-lit, but sporadically populated with vehicles this long after business hours. "What are we doing here?" Angie questioned as we stepped out of the cab. "Baby, Faye and I have someone we want you to meet," I explain...

A Pool Boy

by thongcladtommi on Sep 14, 2017
Loving Wives

It was the summer after my freshman year of college. Rose had arranged for me to do some pool cleaning as a means to justify the cash I was making servicing older women. There was one woman in town whom Rose hoped would fall into line and become pliable. Mrs. Johnson always thought she was so much better than everyone else. The "airs" she adopted when in R...

A Sissy Saga Ch. 20

by Snurge on Sep 15, 2017
Novels and Novellas

Mrs Boroclough lived alone, but her house was the biggest in Peasmarsh. It had tall windows with ornate guards, and a polished copper plate fixed on the wrought-iron gate engraved with her name - as if everyone for fifty miles around didn't know who she was. It was far too big for a widow-woman who's children had grown-up and departed, but she insisted that...

Mary Louise Ch. 03

by mlyn on Sep 16, 2017
Fetish

Beyond Redemption The next week at school passed slowly. She argued with her mother about the clothes and wanted the old ones back, but her parents' stuck together and refused to back down. Come Friday, her breasts seemed extra tender and she felt every dip in the road, painfully with reverberating bounces. All day long it seemed like people were looking...