Chastity Clitty Stories

10,475 results
Orientation
Length
Source
Infinite Scroll

Willing Submission to a Dickgirl Ch. 02

by ArthurSummer2 on Apr 4, 2018
Fetish

Note to the reader: This story takes place in a futuristic world where body modifications and high technology are common place. Because of this, there are a subset of women who choose to have male genitalia attached to their bodies. These cocks and balls can be, and often are, much larger than natural male genitalia. So if you are not interested in futanari/...

Delving into Femdom Ch. 03

by readytokneel2907 on Aug 31, 2020
BDSM

** Chapter 7. Beginning my Training After closing the door behind me after my first session with Domina Electra, my heart was racing. I couldn't believe what had just happened, and instead of taking an Uber, I elected to take public transportation, which wasn't far away. While it was snowing, it wasn't overly cold, and I was excited about the possibility of...

Letter from Smucker Landing

by justincbenedict on Apr 27, 2020
BDSM

LETTER FROM SMUCKER LANDING Dear Shoeblossom, I was featured in my brother's letter about being raised in a femdom family in "Letter from Lantham Chase" and I'm also in "Letter from Purcellville" having to do with a neighbor's early experiences when he met me in grad school. I have been in the scene on and off for a while...and now I'm writing my own lett...

The Wedding Ch. 01

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

(Intro) This is the continuation in the life of Dale Horn and the never ending saga of both his pleasure-- and his plight while living in this new world of sexuality and discovery brought about through the hands of his caring, supportive Mother and as well, his long lost love Patti... Where we left off -and with every ones encouragement our Dale saw himself...

Butch's Bar Slut

by sissymissyct on Jan 7, 2020
BDSM

(A bit darker than most of my tales. It would fit in gay or nonconsent as well. Gay sex, sissy sex, chastity and punishment.) *** I love this bar, Butch thought to himself as he finished another beer. And why shouldn't he. It had everything a Leather Bear could want. Plenty of hot men in leather, and some women as well. A bunch of trans girls and some siss...

Help Wanted

by maidgirl on Dec 16, 2017
Transsexuals & Crossdressers

Brian found a table at the coffee shop, and sat down. This shop was his haven during the day. He had been applying for jobs since being laid off three months ago, and would use the shop's free internet. His savings were running out, and Brian was starting to feel desperate. "Order ready for Brian" the barista called out. Brian quickly grabbed his coffee. As...

The Spirit of Lady Macbeth Pt. 08

by alyssawinters on Oct 19, 2020
Transgender & Crossdressers

Feeling helpless yet pretty the shorter Olivia sat between Wanda and Lori still holding the two smallish pompoms. Glad to be back at their house Olivia had an apprehensive smile on his face as he tugged trying to pull the hem of the cheerleading skirt down a little more. It had taken time yet he adjusted to being a cheerleader with the four genetic females a...

Lace and Love Ch. 01

by vaultdweller111 on Sep 19, 2017
Transsexuals & Crossdressers

Daniel Sohn let out a sigh of relief as he finally finished met his deadline for a computer company who had hired him to write a program for them. The twenty five year old Asian man was an expert at programming and software design and was hired regularly by various corporations to write code for them. He was so good he could do it all from his home which he...

Ultimate Sissy Weekend Ch. 04

by SissyTwinkleToes on Jan 13, 2020
Transgender & Crossdressers

Susie is lying in the store supply closet next to Tinkerbell. It's six in the morning, and they've only just finished cleaning the entire supermarket. After changing each other into fresh diapers, and using the few left over to make pillows for them both, the two exhausted sissies lie side by side in the cramped supply closet. Tinkerbell's right hand, handcu...

The Secret of the Island Pt. 01

by neoview on Sep 25, 2017
Transsexuals & Crossdressers

Hello, this is my first story I upload (not the first story I made). I am sure I didn't do a good job expressing my thoughts so please excuse me. You will notice the walls of dialogue and not so much "explaining". That's just my style but I hope to improve for the future. Anyway I expect some constructive criticism but please use simple words, I'm not stupid...