Sissy Pussy Stories

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Orientation
Length
Source
Infinite Scroll

A Little Twist Over the Road

by mdw_dark_angel on Sep 17, 2017
BDSM

Master is an OTR driver for a national corporation. That could make things very difficult for O/our relationship as W/we would not be able to see Him very often, for very long at a time, except that - sissy, affectionately known as pet, and angel, referring to this girl - are His relief drivers. W/we travel with Him everywhere so it makes life a bit more exc...

Ms. Alexandria - Interview No. 02 Pt. 03

by gasissynora on Nov 26, 2019
Transgender & Crossdressers

This is the fourth part of the Ms. Alexandria series, and the third and final part of The Second Interview. I believe it will stand alone, but will make more sense if you read the earlier parts of the story, particularly Part 2b. This part starts with the last paragraph of the previous part. ***** Ms. Alexandria: The Second Interview - A day out. Part 2c...

Sissy Boy Secretary Ch. 04

by Hotenuf4u on Sep 19, 2017
Fetish

Arriving at the office 15 minutes early, walking past three of the other secretaries, noticing them smiling and giggling when they glanced my way. Elaine must have told them of my secret desire to wear panties. Today's choice was the white lace thong pair, which felt good as they rubbed against me as I walked. Feeling my face turning red, I walked faster to...

From Her Ex-Boss to her Bitch Pt. 05

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

This story includes extreme themes of sissification, interracial domination, watersports, cock sucking, if any of these themes are not your thing, please don't read it. ***** "I think you should have tattoo on your back above your pussy cheeks and another above your little Sissy clit." "But I couldn't do that Master, my wife would see." Amber was almost b...

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...

Center of Attention Ch. 02

by Seethru57 on Sep 16, 2017
Group Sex

Disclaimer: All characters in this fictional story are 18 years or older, and all names are ficticious. This is a continuation series. Debbie Ross was sitting on her bed, writing in her diary about the events of the previous night. She wanted to keep those memories, and hoped to add new ones to the lusty events at Mr. Collin's home. Her thoughts were interr...

Sissy Boy Secretary Ch. 05

by Hotenuf4u on Sep 19, 2017
Fetish

The whole week was spent on completing the paperwork needed for our customers. There was a lot of work and I had worked through quite a few lunch breaks, but completed the work on time. Business was getting better each week and Elaine had said that I was one of the reasons that it was going so well. Although I still stripped to my panties while in Elaine's o...

Sindys Undoing

by SindySuxALot on Sep 26, 2017
Transsexuals & Crossdressers

Lucy had been following Dr. Cornelius for months now. He had been one of the 20 endocrinologists in Orlando on her list when she started this quest, and he seemed to her to be the most likely candidate to help her with her goal. She had ruled out almost all of the others after delving into their backgrounds. From what she could tell in her research, Dr. Corn...

Sissy Lesbian Rita Meets Lisa

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my two already published stories: 'Miss Johnstone's Lesbian Sissy Slut' and 'Further Training as Sissy Lesbian'. I sincerely recommend reading these stories first as it provides background for this one. My stories have been well received and I would like to thank you all for the positive response! Enjoy and please ta...

No More Secrets

by Gemsissy on Sep 12, 2017
Transsexuals & Crossdressers

I couldn't wait to get home from work. My wife said she had something special ready for me. A month ago, she'd found out about all my sissy fantasies when I forgot to clear my search histories. Instead of divorcing me, she did more research and decided to embrace me as a sissy. Now every time I get home, I strip off my suit down to my panties, thigh highs, a...