Sissy Spanking Stories

28,144 results
Orientation
Length
Source
Infinite Scroll

Man Disciplines Sissy Ch. 01

by LanaBehave on Sep 14, 2017
Transsexuals & Crossdressers

I enjoy nice undies, sexy undies, soft and pretty lingerie, and delicate and dainty clothes whenever possible. I put on these things, and feel feminine and aroused, eroticized....the pretty dress, the wig, the nylons, panties and bra, heels... I also feel the misbehavior aspect. A boy/male like me, even if it looks sexy or feminine on me...dressing girly is...

Feminizing First Step Ch. 05

by antares34 on Mar 30, 2020
Transgender & Crossdressers

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. Chapter 5 Today began like any other. I awoke in my bed with my wireless earbuds still in my ears. The sissy hypnosis audio track was gently playing...

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...

Spanking Night Ch. 05

by Angelscuck on Sep 14, 2017
BDSM

I took out the scissors and cut my beard and mustache as close as I could then used the electric clippers. After that I finished shaving my beard and mustache off with shaving cream and lather. I looked strange without a beard, younger; my face had a feminine look to it. I had not seem my upper lip and chin for at least twenty years. I did the same process t...

Aunty's Toys Ch. 02

by novelcriss on Mar 25, 2019
Fetish

**Thank you everyone for reading and taking time to vote on Ch. 01. Do please feedback. I hope you like the evolution in Ch. 02. It has taken a lot longer to get going than planned!** ***** Simon stared at his phone in his office, not quite comprehending. Sally or Aunty as she'd told him to call her had sent him a text. "Simmy dear, don't forget your app...

The Sissy and The Gardener

by snorn on Sep 16, 2017
Transsexuals & Crossdressers

As I sit in my office, I am wearing my pink sissy uniform, watching the hired gardener dig up the weeds out front. I'm not supposed to expose myself to others, but my sissy rules state that I must be in uniform when nobody else is inside the house. I'm doing work, but all I can really concentrate on is the idea that I should be on my knees sucking cock, or b...

Girl's Night Pt. 03

by DifferentBreed on Sep 14, 2017
Fetish

Fisher climbed the stairs slowly, wary of the quiet that hung over the upstairs. As he hit the landing a soft moan emanated from the bedroom and his heart raced as he entered the doorway. There, framed in the soft light of the bedroom lamps, was Sophie kissing another woman. Her crisp white shirt was unbuttoned, exposing the top of her supple breasts, and gi...

Mistress's Party Entertainment

by sissyapril on Sep 15, 2017
Transsexuals & Crossdressers

My Mistress was entertaining her sister Lady Brandi and her friend Lady Alexis in the living room and watching a Mistress dominate and humiliate a couple of her sissy slut males on DVD. The ladies were drinking wine as I was attending to the dishes after serving them dinner. I was wearing a French maid's uniform with black patent leather pumps and fishnet st...

High School Dilemma Ch. 06

by LaurenWestley on Sep 15, 2017
Fetish

(Authoress's note: of course all disclaimers are still in place regarding characters etc. PLEASE DON'T READ THIS IS YOU HAVE AN AVERSION TO PEE SCENES AND EXTREME HUMILIATION. This is only a fantasy story XXX+. I only wish there is enough here to make each of you happy. To those who have given me constructive criticisms as well as those with praise thanks. I...

The Training of Sissy Paula Ch. 5

by submissive~pet~ on Sep 14, 2017
Fetish

After the fuckings I had gotten from Max my asshole was so stretched, I had to wear diapers all the time. Mistress Carolyn used this to her advantage. She had a few men that liked sissy babies. The men would bring me all sorts of little sissy clothes. Dress me up and have me nurse their cocks as if they were bottles of milk. One day a new man showed up, he w...