Sissy Panties Stories

160,213 results
Orientation
Length
Source
Infinite Scroll

Sissy's First Gangbang

by TaykenByDaddy on Sep 12, 2017
Transsexuals & Crossdressers

I had been seeing Daddy Larry for over a year at this point. He was the third cock I ever sucked and the one to claim my sissy virginity by being the first to fuck my ass. He was exactly my type; early 50s, stocky hairy build with a small gut and over seven thick inches of manmeat that wanted nothing more than a younger guy to drain his load. The more femini...

Sissy Girl Forever Pt. 01

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

The call from Mistress Andrea made my day. I hadn't seen her for over a week and was looking forward to playing with her & having my chastity finally removed. You should know that Mistress and I have known each other for many years and have I always enjoyed being her sissy sub. Lately she has been training me to be more feminine in appearance. I have been r...

Sissy Chantel, New Reality Ch. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eleven: Sunday Fun Well now that our Masters and Mistresses have left us here in the locker room, with all twelve of us sissies now freed from our chastity, our sissy dicks are getting quite hard. We have been allowed a period of sissy sexual freedom. For the next 45 or so minutes we are to engage in a sissy orgy to relieve our pent up sexual desire...

My Submission to a Real Man

by gbr2004 on Dec 28, 2017
BDSM

This is total fantasy and would never do many of the things I discuss. If not into really kinky play, humiliation, verbal abuse, and forced fem and strong discipline, please pass on this story. For all you other submissive boy and dominant men hope you like my fantasies. ***** MY SUBMISSION TO A REAL MAN It was our first actual meeting. We had emailed bac...

Planet Pretty Sissy

by Hayleykim on Aug 18, 2017
Fetish

Louise ordered her kinky slave to stand naked in front of her. He was in his late forties, about eight years older than the pretty blonde, who had him like putty in her hands. "Welcome to your ultimate fantasy. We don't take passengers on this parallel planet. Is that perfectly understood?" said Louise. "Yes of course, Louise," he replied in a stuttering w...

My Wife and I Became Sluts Pt. 01

by mandiejune on May 22, 2018
Transsexuals & Crossdressers

My wife Carol was away for a week due to business conference. She was blonde 25 years old 5' 5" with very sexy body and 36C breasts and very sexy bum. We had been married for 3 years and had no children. I was called Tom and 28 years old and 5' 6" and thin. I was IT systems designer and worked from home. I was also a crossdresser that my wife and Mistress al...

Sorry Sissy You Lose Pt. 01

by LittleDickSissy on Jan 15, 2019
Fetish

Mistress called her sissy to her chamber, "Slave - you are to come here and upon entering crawl on all fours." Slave did as instructed without hesitation. He was athletic and manly, but his little dick was weak and it drove him to submit to her. Her power was her pussy, her body, her attitude. He knew his needle dick didn't fill her pussy let alone stretch...

Sissy Amy Loves Mummy Belinda Ch. 01

by Sissy Adele Howells on Sep 17, 2017
Fetish

My world had turned upside down, when realising that my favourite fantasy was about to come true. The story that I am about to narrate, is about my obsession of being a kinky, sissy, little girl. Everything seems so real and I could not stop myself from falling deeper into this kinky world of fantasy. For the benefit of the reader I am forty eight years of a...

Ms. Tanaka Fixes Me Ch. 02

by chenwanli on May 4, 2020
BDSM

Chapter 2- Ms. Tanaka Takes Charge Ms. Tanaka stood up, straightened her sheath dress and bowed to her daughter Hiroki to say goodbye. They exchanged a few final words in Japanese that I didn't understand, gesturing at me and smiling then Ms. Tanaka laughed throatily and demanded the rest of my clothes. I took my pants off from around my ankles and gave her...

Panty Jerkoff Encouragement

by dirtywordygirl on Sep 13, 2017
Exhibitionist & Voyeur

Right now, I just want you to lay back on the bed and show me what you have down there... No! I DIDN'T SAY YOU COULD TOUCH IT! That's very naughty of you to do that. First you have to ask me, so let go of your cock and show it to me like a bad little girl...you're a very bad little girl, aren't you? Let's get you a little wet and slippery, ok? Ask me if y...