Sissy Chastity Story Caption Stories

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Candi's Conversion Ch. 02

by CandiCumminz on Sep 12, 2018
Transsexuals & Crossdressers

Please read chapter 1 first. - We join Candi, dressed to the nines as a sissy princess, sucking on her lipgloss tube and dancing like a slut. Her wife and her friend have just walked in on her, rubbing herself to orgasm. She's in for it now... - "What the fuck is happening here?" My wife stammered in disbelief. Her company, a friend named Lucy who I'd m...

A Sissy's Halloween

by Evangeline_E on Oct 29, 2018
Transgender & Crossdressers

Disclaimer/authors not: All characters in this story are over the age of eighteen. This is my first story so criticism is wanted as long as its constructive. I make these stories based on what I want and my own sexual fantasies. Thank you 😊 . * To tell this story right I need to start at the very beginning, the time where I first started to question my se...

My Friday Night: Disconnected

by honey28 on Sep 16, 2017
Transsexuals & Crossdressers

Although it has been two years since I posted a short story, I never stopped writing. In 2012, our relationship was at its start, and I began feeling things that I was not ready to share with him yet. Those feelings were coming through in my writing, so I kept my stories to myself for a long time. I actually wrote a book, and was also busy with editing Nicho...

Humiliated Stable Sissy Pt. 02

by SissyTwinkleToes on Oct 5, 2020
Transgender & Crossdressers

I woke up exhausted at the crack of dawn to Fairy Godmother obnoxiously clicking her fingers next to my ear. I minced downstairs, still locked into my ultra prissy outfit (where was the key?) and my totally exposed diaper, already damp from last night. I shuddered as Fairy Godmother ordered me out into the back garden, where I stood and curtsied to the risin...

The Intern Ch. 02

by FrostShard on Sep 14, 2017
BDSM

I didn't see Mengxia again for the rest of the day. That didn't mean she wasn't on my mind though. In fact, I thought of little else all day, and found it really hard to work. Towards the evening, I received a Snapchat from her captioned "Missing me?" showing a low selfie of her face, her full lips and the top of her cleavage. It got worse a few seconds lat...

Miss A's New Play Thing

by Pornenthusiest on Oct 8, 2019
BDSM

Chapter 1: Sexual Awakening Alex's morning ritual had changed lately. Typically he would start his day by slamming his alarm clock, getting out of bed, brewing coffee and taking a shower. But now, Alex was generally restless, always waking before his alarm could rouse him. He would rush to his computer immediately checking his messages, today was no differe...

My Friday Night: Switch

by honey28 on Sep 5, 2017
Fetish

Driving home on Sunday night, my phone rang when I was stopped at the light waiting to turn onto my street. Seeing Nick's name, I put him on speaker phone. Before I could say anything, he very loudly declared, "I want to lick your pussy." Hearing that deep, sexy voice usually makes me melt, but I had to giggle. Note to self: never answer his call on speakerp...

The Pantysissy Diaries Ch. 03

by JPantyboyVSL on Apr 23, 2019
Transgender & 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 Chapters 1 and 2 before reading chapter 3. ***** It was nighttime in NYC, and Jaymie and her 6 Mistresses had just left their apartment to head to Vic...

Covid 19 - Pete Turned into Charleigh Pt. 02

by His_fag_wife on Jul 13, 2020
Transgender & Crossdressers

Again it was as though she'd slapped him back into reality, just as she intended, she'd noted his angry response earlier that day and wanted to trigger him again, but trigger him much more this time. She simply would not accept rudeness or attitude from him. Pete had to realize that as Charleigh took over his psyche, that she would need to be more and more s...

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...