Sissy Whore Stories

50,992 results
Orientation
Length
Source
Infinite Scroll

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...

Discovering Mistress Sarah's World Pt. 04

by oneguy4fun on Sep 12, 2017
Transsexuals & Crossdressers

Special thanks to Mistress Sarah and Miss May and Miss Mill who are my motivation for this story. Thank you for your guidance and wisdom and for the privilege of serving you and writing about you. Chapter 11 Discovering the Girl in Him For the first time since he arrived at Mistress Sarah's house, Josie was left alone in silence. His cock was still thro...

The Neighbor Daddy Next Door

by ddogg44 on Jun 4, 2019
Transgender & Crossdressers

PART 2 (continuation of "college is a time to explore) Daniel awoke with the feeling of a lacy black thong riding up his ass. A raging hard on pulsed in rhythm to the sound of Text messages being received. It was the next day, and Daniel was due for a spanking by his next door neighbor "daddy" for getting some cum on the carpet. "Be here at noon, keep th...

A Dream Come True Ch. 01

by searic on Sep 17, 2017
BDSM

Arriving at the hotel you had selected after a not-unpleasant drive up, I had plenty of time to obey my instructions. Carefully unpacking, I hung up and put in drawers my few vanilla clothes and all the sissy things you had selected for me to bring. How relieved I was to find myself able to be prepared and in position in advance of the time you had set for...

Cucky Trained by CD DOM Pt. 04

by sndycd on Sep 15, 2017
Transsexuals & Crossdressers

At 7:00pm you arrived in my room. You were fully dressed and looking very good. I sat you down and did your make-up and hair. Since your original wig was still splattered with cum I picked you out a different one. Similar in style but brunette. You looked like a totally different whore. "We are going to have company tonight, slut. You will greet our guests...

I Admit I Was Speeding

by Cute Little Thing on Sep 16, 2017
Transsexuals & Crossdressers

I admit that I was speeding, when the cop pulled me over. What can I say, I was rushing to get home. I get that way when I have panties and a bra on. But let me start at the beginning, because this is a long story. It was a Friday night and I had been saving up all my courage for a month, since my girlfriend had told me she would be going out of town for the...

The Fantasy Trip

by mdw_dark_angel on Sep 17, 2017
BDSM

This slave's excitement was rising as the time for Master to arrive and fetch one drew near. The list of things one had checked so many times, containing the items one wished to bring in case they were required, was in tattered shreds in one's hands as one twisted and smoothed it over and over... one's nervousness quite evident in the gesture. Each item was...

Being a Sissy for Viv Ch. 06

by Caron on Oct 31, 2017
Transsexuals & Crossdressers

Lunch was a pleasant time. I'd prepared and served the food, but we had sat together in the lounge. The blinds down against the weather and prying eyes. The time had felt much closer to friends chatting over lunch than the Mistress-sissy relationship of our previous time together. Viv probed gently about my desires. Intently interested in where and how I had...

Uncovering the Sissy Beneath Pt. 07

by jefferyscott745 on Aug 6, 2019
Transgender & Crossdressers

Disclaimer: This story contains extreme fetishes including BDSM and forced seduction. It is also purely fictional. This is part seven of my previous work. Be sure to read parts 1-6 if you wish to understand the background of this section. Three days had gone by, since Sherry and I had our intimate session together. We had practiced multiple times after t...

Desiree's Cock Quest

by desireethtttv on Sep 16, 2017
Transsexuals & Crossdressers

It had only been a month or so since Suzie discovered my secret stash of letters between my alter ego Desiree and another transvestite. In them she read how we both love to suck big black cocks and our bragging on the longest cock we'd ever sucked. Needless to say, it put quite the strain on our marriage. With the fact my love for long hard cocks was all o...