Miss Vicky Sissy Storys Stories

86,810 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Ugly Duckling to Sissy Princess Ch. 05

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

Bernice held my hand and pulled me out of the bathroom to her living room where there were five very pretty girls, sissies, I will use the word "gurls" to distinguish them from girls that were born with a pussy. I recognized a few of these gurls from the party at the mansion. The gurls' names Deborah, Jill, Vanessa, Shirley and Anne. Each of them was very...

James' Story Ch. 01

by Besissyb on Sep 14, 2017
Transsexuals & Crossdressers

James was an average 23 year old loser; short, scrawny and wholly unremarkable. He often found himself scouring all the bars and clubs in the city he lived in looking for even one woman that would give him the time of day. One night, or rather early morning, James had lost all hope and decided to make his way back to his single room apartment. He checked his...

March Madness Ch. 09a

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

Ugly Duckling to Sissy Princess Ch. 04

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Chapter 3) Several nights had passed after the party at the mansion and kissing Ted. Bernice called me Saturday and Sunday, but, both nights I told her I could not come by to see her. On Saturday, my girlfriend went to a party thrown by the basketball team. I knew she would end up fucking one of them, he would use her like a piece of meat,...

On Your Knees Ch. 10

by JinkiesFarie on Sep 16, 2017
BDSM

His knees were shaking by the time her finally reached her apartment, he struggled to catch his breath. Clutched in his left hand was his high heels, he had kicked them off and started to run shortly after his encounter with the hobo. Timidly, he knocked on her door, but after a few minutes of no answer, he decided that she wasn't home. Vicky was about to co...

The New Swim Team Pt. 06-07

by Doubleganger on Sep 19, 2017
Exhibitionist & Voyeur

Disclaimer: I began writing this seven part saga in late 2015. As the old saying goes; all good things come to an end. Here are parts 6 and 7. I hope you enjoy reading them, as I did writing this chronicle. All are over 18 years of age. This story is completely fictional. None of the characters portrayed are real, also none of these sexual encounters ever...

Caitlin and Mistress Vicky Ch. 02

by Jemina004 on Sep 19, 2017
Transsexuals & Crossdressers

I hummed softly as I put the finishing touches on the salmon. Teriyaki salmon was my wife's favorite dish and it filled me with pride to know that I was making her happy. My mouth watered slightly as I arranged the tray. (I would only be having a salad myself, as I had to maintain my figure.) Taking out a pocket mirror from my apron, I checked myself to ma...

Caitlin and Mistress Vicky

by Jemina004 on Sep 19, 2017
Transsexuals & Crossdressers

*Clack* *Clack* *Clack* The sound of my heels on the kitchen tile was distracting me right when I needed to focus. My wife, or Mistress Vicky as I'm to call her from now on, had left me quite a bit of chores to do today. I had just finished dusting and was getting ready to polish the kitchen floor when the doorbell rang. *ring ring* Swallowing nervously,...

On Your Knees Ch. 05

by JinkiesFarie on Sep 16, 2017
BDSM

He grabbed his shaft as he sat in his office, shame burned in his cheeks. This was his place of work, but the thoughts of Nicole were so powerful, so overwhelming--he couldn't help himself. During his lunch period, he had locked himself in there instead of taking the usual route into the school's cafeteria. Nicole penetrated his thoughts. In his little fan...

Hotwives Ch. 02

by Donna Williams on Sep 16, 2017
Transsexuals & Crossdressers

HOTWIVES II by Donna Williams ((Read the first part of the story in "Hotwives" first)) I was now a hotwife, Vicky was a pseudo hotwife, and John was a sissy, cock sucking cuckold. Everyone got what they wanted, if not more! * * * Once John had fallen asleep, Dave and Rick left as we had planned. When John woke that morning, he found me in the shower. "You...