Sissy Nails Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

Sissy Instructions

by FrostShard on Sep 13, 2017
BDSM

Dear sissy, I trust you are preparing yourself well for our session next week. This session will be your final plunge into the realm of sissyhood. Thus far, you have simply dabbled in it, all the while essentially staying a man. All that will change starting from this session. Starting now, from the moment you finish reading this letter, one thing will cha...

Transforming Brent

by sissymissyct on Jul 9, 2019
Loving Wives

Katherine decides she wants to live with her lover Wendy. They come up with a plan to slowly change Wendy's husband, Brent, into their girly sissy maid full time. Will his resistance be broken? I put it in loving wives but it fits multiple categories. Will he will learn to love his new role in life? Yes, The narration switches between characters. If this bo...

His First Taste of the Real Thing

by 2easy2 on Sep 19, 2017
Fetish

My girlfriend, Angie, has been dressing me in women's lingerie and pegging me with her strap on dildo for a couple years now. It started with an occasional pair of satin panties and quickly moved to sexy little nighties, stockings and painted toenails. As bad as I hate to admit it, I absolutely love it. It's all I think about anymore. I love the submissive...

Savannah's Hypnotic Socks Pt. 20

by Fibaro on Dec 2, 2019
BDSM

Chapter 24 Savannah eventually pushed her roommate away and looked down under the table. She just stared at her roommate for a bit before asking. "What moisturiser do you use Roxy cause your skin simply shines." She loved how her roommate face turned red at her joke. She didn't really expect an answer either. She just did it because she loved messing with...

The Training of Sissy Paula Ch. 6

by submissive~pet~ on Sep 14, 2017
Fetish

My Mistress goes to a lot of trouble to fix my nails, hair, and makeup. Once she is done she tells me to follow her. I follow her to the car as instructed. Paula take off the panties. Yes Mistress Candy. Now for a very special long trip Paula. Where are we going Mistress Candy? You will see in about 3 hours sissy. O.K. Mistress Candy. Now I want that assh...

Sissy Cuckold & The Old Bull Ch. 01

by DirtyDaddyHunter on Sep 19, 2017
Loving Wives

He waited on the bed as instructed. He had dressed exactly as he was asked: A pair of lavender lace trimmed panties stretched tightly over the young man's small cock; a matching bra covered his hard brown nipples too. He also had on a garter belt and some high heels. Too top in off he had on some coral lipstick and he had painted his nails perfectly. There...

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...

Dominating Sugar Daddy

by LittleDickSissy on Jul 3, 2018
Erotic Couplings

The sissy cuckold was at the ATM withdrawing cash for his Mistress. He needed cash for her nails, her new dinner attire, and makeup. As he made his withdrawal his little dick dripped precum in his purple lace panties. He always got turned on every time his Mistress provided strict instructions to him, and of course whenever she played without him. "Now tell...

A Sissy's Life

by Queen_Diana on Jan 27, 2020
Fetish

A Sissy’s Life by Queen Diana Slutty pink lip gloss? Check. Ass cheeks practically hanging out of a scandalously short pink skirt? Check. Pink tube top, butt plug, and thigh high stockings? Check. “Check, check, and check! That’s everything!” I giggle. Looking over at the body length mirror. Writhing with satisfaction, as I realize, what a pretty little sis...

Sissy Shopping

by Candour on Sep 25, 2017
BDSM

My first story, finally edited and tidied up. I hope you enjoy it, I enjoyed writing it. --------- You were standing in your local department store in the make up section, looking for foundation. Not too sure what you are doing, and must have looked a little lost as one of the sales girls came up quietly behind you. She was a delightfully pretty 18 year ol...