Diaper Sissy Chastity Stories

13,981 results
Orientation
Length
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Infinite Scroll

Naughty or Nice

by BigTittyHexManiac on Dec 23, 2019
Group Sex

Editor's note: this story contains scenes of incest or incest content. ***** Inspired by an online writing prompt. ====================================== The clock stroke midnight. Christmas morning officially began, and a young man by the name of Jason and his twin Mason officially reached eighteen years of life. But there was still time before the sun...

Bi Cuckold Humiliated and Fucked Ch. 03

by DaveLoveAss on Dec 16, 2019
Fetish

Part 3. If you haven't read the first one you should do that and learn how the cuckolding began. People keep asking for more so here it is, the second night... * Work that day was long and painful. Every step was a gentle reminder of the pounding Abe had given me the previous night. Every time I sat down was excruciating as my ass never seemed to fully clo...

Wanderlust - Sabrina Pt. 05

by GeneraZ on May 11, 2020
Sci-Fi & Fantasy

5 - The Power Shift Paul's feet flexed painfully within the pink high heels. They weren't his, and they were much too small. With their lift he was exceeding six feet in height, causing him to loom over his beautiful blonde haired counterpart, but that did nothing to change the air of power she held over him. She giggled sinisterly as he, otherwise complete...

COVID-19 - Campus Closed

by puzziboi on May 12, 2020
Transgender & Crossdressers

"Momma, they're shutting down the campus on Friday," lamented the college junior. "I figured they would. I've been on the phone with Aunt Nettie. You can stay with her for the time being since she's close." "Doesn't she already have a ton of people living with her." "Patrick..I mean, Prisha," she swallowed hard. "There's just not a lot of options right no...

Be Careful What You Wish For

by ChainedToAKeyboard on May 12, 2020
Fetish

Author's note: This short story was inspired by Vitalis' amazing hentai artwork: "Bimbo Catalog: Bianca." * It was date night in the Whitley household and things were just starting to get exciting. Alice and Richard had enjoyed a lovely meal at a five star restaurant, a wonderful performance at the theater and a couple glasses of fine wine upon returning h...

Picked Up On the Prom

by DeborahC on Jul 15, 2020
Transgender & Crossdressers

I was nearing 20 years old and had no real life plan. At my Aunts suggestion, I accepted her invitation to use her coastal cabin. I was her favourite nephew and she thought I could make use of the solitude, the wide open space and the fresh sea air to gather my thoughts. The village near her cabin was a lovely old place. Set in a valley between rolling hil...

Bitch Trains A New Cum Slut

by dicktinie67 on Aug 17, 2020
BDSM

Bitch Trains A New Cum Slut -- Ch. 01 It was not as fun as I thought it was going to be. It started out great, but it did not end so well. My buddy, Mike and I were on a fishing trip in Maine and we met a couple of girls doing the same that were staying in the cabin next to us. I probably should give you some background on the friendship between Mike and...

I'm a Mess

by ClarasBestFriend on Oct 6, 2020
Loving Wives

Mike, my loving husband, had finally convinced me. Ever since we had gotten married, and even before then, he had been trying to convince me to fuck other men. "I want you to feel real pleasure!" "My little cock doesn't fill you nearly as much as you should be filled!" "I want to see you really get your brains fucked out!" I had heard things like this f...

Sissy Powers Ch. 01

by ClarasBestFriend on Sep 29, 2020
Sci-Fi & Fantasy

I smiled, looking at Clara resting her head on my chest, the way she usually does in the morning. But something felt different... Wait! Everything from earlier in the day came rushing back all at once, and I realized why these wake-up snuggles felt different: Clara's beautiful face was resting on my impressive bust! Clara laughed at feeling me jerk in sur...

Sexy Mandy Gets Her Just Desserts

by BAD BOY BILL on Sep 28, 2020
First Time

The day was fucking hot, Typical Southern California weather. I had been here a week and still wasn't used to the heat. San Francisco could get warm but not like this. Our saucy Mandy Collins had been the perfect host. Dinners, workouts, massages, and of course, fucking. Platinum haired Mandy had drained my ballsack several times a day for the last week. S...