Sissy Model Stories

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Sissy Starlet

by Queen_Diana on Nov 18, 2020
Fetish

First Sissy tell me. Who are you? Jenn- A tall long and blonde sissy. Platinum blonde locks that go all the way down to her back, glossy pink lipstick, long manicured nails, a model face, and killer ass and legs. One of the favorites for this year. Racheal - A brunette Sissy, with wonderful perky titties and plush ass, dark skin and luscious lips. Kim - An A...

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Fetish & Fantasy Pt. 01

by GavinIsaNuisance on Jul 13, 2020
Transgender & Crossdressers

This work is completely fictitious, any similarities to any persons living or dead is purely coincidental and entirely unintentional. All persons depicted in naked/sexual acts are 18 and up. Down and out aspiring model Taran Kilkenny becomes the hottest commodity in an escort service for trannies! But first he's gotta get trained by his new and domineering b...

LeAnn Turns Dan into Desiree

by desireethtttv on Sep 12, 2017
Transsexuals & Crossdressers

I'd never shown my friends my true personality. Always in the forefront was a normal guy who loved girls and all things boy, when in fact, with each passing year, the things that excited me were all things feminine, including actual men and their boy parts. This remained status quo, until I met LeAnn. Introduced to the long haired blonde chick by a mutual f...

Neighbourhood Terror to Sissy Pt. 14

by Fibaro on Dec 2, 2019
Transgender & Crossdressers

Chapter 16 The two women enjoyed looking at Mark as he had to swallow all the white goo he had just squirted. Just as if the way he had achieved his orgasm wasn't bad enough yet? This only added insult to injury. It was Linda who suddenly broke the silence. "It is good you have come here to learn how to handle a sissy and it is my pleasure guiding you int...

The Intern Ch. 04

by FrostShard on Mar 6, 2018
BDSM

The day after Mengxia had me listen in to her having sex with her boyfriend, I went back into work with some trepidation. Aroused from my three weeks denied orgasm, humiliated by the events of the previous evening and nervous about my meeting with Mengxia that evening, I could barely focus on work, and it seemed to take ages for 5 pm to roll around. At last...

The Pantysissy Diaries Ch. 03

by JPantyboyVSL on Apr 23, 2019
Transgender & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapters 1 and 2 before reading chapter 3. ***** It was nighttime in NYC, and Jaymie and her 6 Mistresses had just left their apartment to head to Vic...

My Sissification Ch. 02

by sissy171 on Aug 31, 2020
BDSM

I had always planned to go to college, but I was already fairly secure in my business, so I entered college with no scholastic trepidation. My way bigger fear was that I was still sporting a bikini tan, which kept me conflicted; fearful of being discovered, constantly on a sexual edge, and woefully missing Beth. The bikini bra outline was her "brand" upon...

Legally Binding

by MistressMtoyou on Aug 31, 2017
Fetish

As I explained in my first story (My first submissive), I'm fortunate to have a high paying job at a large well known firm. While my employer is equal opportunity and all of that, even the most open minded employer wouldn't react well if they learned they had an amateur dominatrix on their senior staff. Accordingly, before going much farther with my little h...

Unknown Waifish Model Ch. 01

by Couture on Sep 12, 2017
Transsexuals & Crossdressers

We lay curled up to one another in the hotel bed, Sandra and I. I looked forward to the day we'd no longer have to make do with hotel beds and the occasional foray to my apartment. Yes, one day soon, she would leave her bastard of a husband and move in with me. God, she was beautiful. Her blonde hair was mussed up, as she lay on the pillow. Her face had th...

Sissy Maid to Be... Ch. 02

by missjennymaid on Sep 10, 2018
Transsexuals & Crossdressers

I would recommend reading Chapter 1 to get to up to speed on the story, but if you want to start in the middle... Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife. Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves. Jeremy is get...