Sissy Clitty Stories

9,676 results
Orientation
Length
Source
Infinite Scroll

A Night with Clarissa

by Spango on Sep 28, 2020
Transgender & Crossdressers

A Night with Clarissa Dear Readers, I know some of you came here hoping for more about my budding relationship with Kevin but, if you recall, I had promised Clarissa that I would tell her all about my night with Kevin while she pounded my sissy ass with her massive strap-on Big Bertha. Of course that night turned into most of the weekend but that just m...

Ultimate Sissy Weekend Ch. 07

by SissyTwinkleToes on Mar 10, 2020
Transgender & Crossdressers

Ruby is sat flicking through a magazine. Mid-twenties, she's been working in the tattoo parlor since college and is soooo bored. So her face lights up when two sissy dumplings mince into the tattoo parlor. She gasps at their ridiculously effeminate outfits that no woman would be caught dead in. She can't believe they've handcuffed themselves together and loc...

Halloween Pool Party Pt. 08

by sissymissyct on Sep 14, 2017
Fetish

Friday morning cam and I was awakened with an electric shock that ran from my tits to my clit. My eyes flew open to see Miss Maddy and her girlfriend each with one of my nipples in their mouth. Pulling at the rings with their tongue, my high pitched squeal announced I was awake. My clitty tried to get hard but had no place to go. I reached to touch it and co...

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...

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...

The Awakening of a Sissy Pt. 10

by sissyjolie4u on May 11, 2020
Transgender & Crossdressers

Best I could tell, neither one of us had moved an inch from the position that we fell asleep in. The urge to pee woke me quite early, like 4 AM early. A smile came to my face as I realized I was still holding Tim's cock. While barely awake, I made my way to the bathroom and took a seat to pee. While sitting there peeing, it hit me that I should probably do a...

Rene and Gene

by Bakeboss on Sep 16, 2017
Novels and Novellas

Part l My first Friday as Jean: Although I work at home, I still took the day off to make sure all the housework was done. Rene called on her lunch hour and said she bought a surprise for me, that she felt naughty and wanted us to spend the weekend doing naughty things. I was hard at the word naughty; my beautiful wife is such a tease and enjoys role-playi...

Sissy Veronica's First Time

by 938ab on Sep 16, 2017
Transsexuals & Crossdressers

This story contains a cross-dressing guy sucking the cock of another guy -- if that's not what you're looking for, please move along. ------------------------- I had met 'Sissy Veronica' online, in a roundabout way. Turns out we were both married men with bisexual urges that we hadn't yet acted on. We were both on a swingers' site as couples, and while tr...

Yesterday Afternoon

by allourdesires on Jun 10, 2019
Transgender & Crossdressers

A lunchtime call; I was to leave work immediately. Once home I would find everything laid out on the bed: nightie, bralette, cotton panties, hold-ups, lipstick, silver choker and...a blindfold? When I was ready I rang her as ordered, covered my eyes and began to toy with my nipples in anticipation of what was to come. My little clitty jumped inside my panti...

Lexi's Date

by Sissy_Sammi_ on Dec 24, 2017
Transsexuals & Crossdressers

As Lexi scrolled through the photos of lewd sissies, she felt her sissy cock press against its pink cage. She wiggled her butt against the chair to feel the plug that was in her. She felt the soft panties against her smoothly shaven bum, and smiled her pink lipstick covered smile. She checked the time, 1:23 AM, and decided that she needed to finish up and ge...