Sissy Nails Stories

53,010 results
Orientation
Length
Source
Infinite Scroll

Neighbourhood Terror to Sissy Pt. 25

by Fibaro on Oct 5, 2020
Transgender & Crossdressers

Chapter 27 Marcy woke up with a loud groan as her alarm went off loudly and way too early. She really had to drag herself out of bed as she didn't look forward to her day ahead at all, but she couldn't afford to waste much time at all as she still had a busy morning ritual to take care of. It started off bad with the kiss to the dildo, although she had to a...

Miss Guided Pt. 05

by MissMarianne on May 6, 2019
Transgender & Crossdressers

We had a lovely dinner after which Donna walked us back to the new apartment. I decided to make us some coffee while Donna and Charlene had a conversation in the dining room. I could hear everything they were saying. "So, Charlene, Susan has told me that you have been a very bad girl. You were very naughty and need to be punished she said. I am very disa...

Don Venuto's Sissies

by marybethsanford on Aug 18, 2017
Fetish

Players: Capo De Matzo, counsel to Don Venuto. Don Venuto also known as the Godfather; Mario Venuto, son of Don Venuto; Ms. Rosa Cappella, professional dominatrix; Carol Evans, mother of Mark Evans; Mark Evans aka Martha Evans; Helen Andrews owner of the Little Miss Muffin Boutique; Ralph Summers, a friend of Mark, aka Robin; Steve Franks, friend of Mark, ak...

Caught by the Past Ch. 03

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 3 - Friends United Previously - When you dressed as a sexy tart for James he showed two sides to his character. Bent over his knee, stuffed with a butt plug and forced to suck his cock. What more could he possibly do?... Read on After sucking his cock you sit on the sofa supported by a fluffy white cushion, shoes kicked off, legs curled under your...

Mikey becomes Melodie Ch. 02

by tiffanyfoxe on Jul 14, 2020
Transgender & Crossdressers

I lay there under this incredibly beautiful fully transformed girly-boy, her lipstick covered lips still softly and tenderly kissing me, kissing my lipstick covered lips, my rouge covered cheeks, my eye shadow covered eyelids and my mascara coated lashes, showing how much she loved having me under her, her huge still hard cock buried deep inside my pussy/bot...

Special Girls

by chloevargas on Jul 15, 2020
Transgender & Crossdressers

We get together every Thursday at lunch. Our friend Emilio loves having us, tells us we add some glamour to the place. His little restaurant is popular enough that we're lucky to have a standing reservation for luncheon late in the week. Should one of us be absent, we buy her meal and wine anyway else Emilio glare at the empty seat. Ricki is our waitress, a...

Cassy's Game Ch. 4

by wormwood on Sep 19, 2017
BDSM

Another day late for work, with the new sensation of my cock cage lumbering under my panties, my hair still plastered down to my head from my session with my Mistress and the feeling of my hairless legs and ass under the silky material of my panties. The strong smell of my wife's feminine moisturizer, making a silent announcement of my new found femininity,...

Exposed Sissy Slut

by MarkRoberts64 on Sep 16, 2017
Exhibitionist & Voyeur

I've always been turned on by exhibitionism, and especially by so-called "forced" exhibitionism. The last few years, I've noticed more and more that I love the game of taking risks in public, where I could possibly get caught being submissive, or slutty, or a sissy. I'm not interested in just exposing myself, or strutting around with a slave collar on. What...

Clara Bow's Academy for Ladies Ch. 02

by Sputnik57 on Sep 15, 2017
Transsexuals & Crossdressers

The new sissy stood barefoot; naked but for the soft white gown. Though bewildered and a little scared, her little cock poked forward in the gown, partly through fear and partly through excitement as she felt the eyes of the stern woman upon her. Clara Bow rose slowly from the leather chair she sat in, cane in one hand, she wagged a finger summoning Pepper f...

Humiliated Stable Sissy

by SissyTwinkleToes on Oct 5, 2020
Transgender & Crossdressers

After a long week at work, I was looking forward to a quiet weekend of relaxing in front of the TV with a beer, but my fairy godmother had other ideas. "Good morning sissy," came her stern voice as soon as I woke up Saturday morning. I whimpered, immediately knowing I was in for a humiliating weekend. She frowned, not pleased with my whimpering. She's an ol...