Chastity Clitty Stories

10,475 results
Orientation
Length
Source
Infinite Scroll

The Pantysissy Diaries Ch. 02

by JPantyboyVSL on Jun 5, 2018
Transsexuals & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapter 1 before reading chapter 2. *** The Amtrak train Jaymie was onboard with his new Mistress, Sydney had just pulled into NYC. Jaymie had to get...

Indoctrination of Toy

by SkyeNightshade on Oct 8, 2019
Transgender & Crossdressers

toy waited patiently kneeling on the floor. She was wearing her short girly skirt, high heels, garters and stockings. Her nipples were bare, as instructed, and the cool air teased her nipples into a hardened aroused state. toy was wearing her favorite dark haired wig, light eyeliner, and bubblegum pink lipstick. As a standing order, she was also wearing her...

Shopping and Sucking

by Subkoksukr4u on Mar 2, 2020
Fetish

Matt was in the kitchen as usual preparing breakfast. He'd been instructed to prepare all the meals according to a specific menu plan each day. He finished the sauce for the eggs Benedict got on his knees and waited. He was wearing frilly pink crotchless panties and a matching bra, his bright pink CB 6000xs chastity device was barely peeking out between...

Kayla's New Life

by BelleBlack on Aug 24, 2020
Transgender & Crossdressers

Kayla sat on the patio of the coffee shop and fiddled with her latte. The nervous energy flitting around her stomach was matched by the light summer breeze that couldn't seem to make up its mind which way to blow. Although on the outside, she was a perfect picture of demure grace, inside her head her thoughts raced frantically. This is crazy. No it's not,...

Created in the Image of a Superior Being Ch. 03

by alyssawinters on Apr 21, 2020
Transgender & Crossdressers

'Created in the image of a superior Being.' Part 3 Gloria's husband Greg's sensed his world was coming apart at the seams the day he was let go at work. Words were spoken anger flared up him and the boss glaring at each other it seemed they were one chair-toss away from it becoming a 'Jerry Springer' show. Unaware of it he hadn't known Gloria negotiated a...

Jacki's Journey into Sissyhood Pt. 03

by jacki697 on Sep 18, 2017
Transsexuals & Crossdressers

This is the 3rd installment of the Jacki's Journey series. I'd like to thank those who were nice enough to add comments and feedback on the proceeding stories. I'll try and keep them cumming. ***** I had a couple days to evaluate Steve and Laura's offer and I was no closer to a decision than I had been. I went back and forth on the verdict. How was I goin...

Jerry becomes Jill Pt. 05: July 4th

by gasissynora on Apr 27, 2020
Transgender & Crossdressers

Jerry becomes Jill: Part 5: July 4th Week End This is the fifth part of my story about how I became Jill. After having started female hormones, Jill is introduced to group play by Mistress Rikki. The Fourth of July is on Monday and that Thursday evening at dinner Mistress gives me some information about the holiday weekend. She says, "Tomorrow you are done...

Pretty in White Ch. 01

by wendy_james on Sep 16, 2017
Transsexuals & Crossdressers

Pretty in white... That's what my Mistress whispered in my ear after she finished dressing me in a white bra, a white knit camisole, a white linen blouse, white sheer pantyhose, and the palest-of-pink panties over them. She stood me in front of her full-length mirror in her dressing room, and she came up behind me. I was wearing white open toe sandals with...

Bookstore Bound

by shawnavinyltv on Sep 13, 2017
Transsexuals & Crossdressers

My Master, ever the gentleman, held the car door open for me. I smiled at him as I turned to get out of the car. I made sure to spread my legs in a very unladylike manner, giving him a good peek up my short dress. He simply shook his head and took my arm. We made our way over to the entrance to the adult bookstore. A small bell jingled as we came in, making...

The Awakening of a Sissy Pt. 11

by sissyjolie4u on Jul 13, 2020
Transgender & Crossdressers

We had been driving in silence for about 10 minutes, with me reflecting on the changes to my home and the 2 men I was going to be meeting. I was both excited and nervous about meeting with Roy and Ronald. Mistress Di broke my thoughts stating "I think Nikki has done an excellent job with her house transformation work, don't you agree Jolie?" I looked over a...