Sissy Clit Fetish Stories

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The Prostate Exam Pt. 02

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. She then persuaded him to...

Sissy Training Vol. 01

by depositdutchess on Nov 27, 2017
Fetish

Being feminine is taught. Correcting your nasty masculine behavior with feminine manners and class is what you need. Being a sissy is your new reality. I am going to make you the pretty little girl you have always dreamt of being. You need to be taught ho live your every day life properly. You can only dream of being as sexy, girly and attractive as a real w...

Transforming Brent Pt. 05

by sissymissyct on Dec 2, 2019
Fetish

I awoke early, partially due to the pressure of morning wood in the chastity. Once I settled down, I showered and slipped on a robe and quietly made my way to the kitchen. I quickly familiarized myself with the layout and, finding what I needed, started cooking a nice breakfast for my mistresses and myself. Ham and cheese omelet, OJ, toast and sausage, along...

A Prom Queen Fantasy

by bluesbirds on Jul 15, 2020
Transgender & Crossdressers

"Aww, isn't this little blue number cute?" Tanya squealed from the other side of the rack. I flinched hearing her voice; we had been shopping for almost 3 hours without a break. This was the first time I had gone shopping with Tanya since she found out about my crossdressing fetish. "Come to this side - let me hold it up to you," she demanded. I meekly co...

My New Friend Amy Ch. 03

by DRobbie06 on Dec 23, 2019
Fetish

As I drove home that evening I had the replay of the days events running on a loop in my mind. I can't believe I paraded around in panties at lingerie store in front of strange women at the instruction of my new mistress. Hell, I signed a contract to obey her no matter what she says! Then I begged to jack off in front of her. I'm even a panty wearing sissy n...

Ami Gattson's Slave Stable

by profperverse on Jul 27, 2020
Fetish

I reported to the home of Ami Gattson as I had been ordered to do. I had a nervous feeling of anticipation as I approached my new situation. Just earlier today during lunch I learned that Susan Russo had "sold" me to Ami for the price of a lunch and a slave girl Susan was getting for me. I understood that Ami had another male slave and a female. My role in...

The Domme Club: The Fucking

by NancyPan on Sep 14, 2017
Fetish

This story will likely be most enjoyable if it is read after reading The Domme Club and one or two other stories in the series (for background of Tom and Monica's relationship and how Tom has previously been humiliated in front of the Domme Club.) Respectful comments are appreciated. ***** Mistress Monica left Tom the standard list of chores to do while s...

Sissy Boy Secretary Ch. 03

by Hotenuf4u on Sep 19, 2017
Fetish

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you! After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in...

Sara's Amazing Night

by Sexy_SaraCD on Sep 16, 2017
Transsexuals & Crossdressers

I felt his entire weight, his entire body push me against the wall and the more I struggled the harder he pushed into me. My hands are firmly planted on the wall and my eyes are closed. At this moment, I feel panic. Panic of what may come soon. His leg, strong and thick, push my legs apart but my tight skirt stops them. He doesn't let that prevent him from...

Halloween Pool Party Pt. 07

by sissymissyct on Sep 14, 2017
Fetish

I was allowed to sleep in late the next morning. Probably so there was time to get the medical room set up for the day's events. When Annie came in to get me up it was past noon. I was allowed a couple sips of water but that was all. My nipples and crotch were sore and that was to be expected. I couldn't see my sissy clit pulled back snugly and permanently b...