Chastity Trans Stories

8,649 results
Orientation
Length
Source
Infinite Scroll

Becoming Daddy's Girl Ch. 03 - Final

by Sungmehetu on Jan 1, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Warning: This chapter is very focused on water sports. The main character ingests urine on a constant basis. If this makes you ill, do not read. ***** My bladder was screaming on the ride home. Every bump in the road, caused a sharp pain. I was about to piss in the front seat, w...

Almost Damsel Almost in Distress Ch. 02

by shawnavinyltv on Apr 23, 2019
Transgender & Crossdressers

I woke up sweaty and a bit confused. I was also having a bit of trouble breathing. I realized I was still wearing my heavy duty corset. I also realized there was someone snuggled up against me! Suddenly visions of last night's self-bondage session came back to me and I remembered Alex, my neighbor, had spent the night. I had a momentary surge of excitement...

Casey's Rise Ch. 01

by velcrofist on Aug 24, 2020
Exhibitionist & Voyeur

Author's note: This is a sequel to the Casey's Fall series. There are many elements in this story that will be more enjoyable and make more sense if you read that first. * Casey rolled over in bed and watched Greg sleeping. He was here so often these days that he had practically moved in, but neither of them thought much beyond how much they enjoyed being...

Trans-Formation

by dreadknots on Jan 20, 2020
Transgender & Crossdressers

This one is a lot more silly than my previous outings, but I think it's still a good read! Featuring guest appearances by chastity, dildo buttfucking, and hypnosis! Oh and turning into a girl at the end, that too. *** "Well," Tim said to the smouldering crater now taking up the majority of his backyard, "This isn't going to help the property value." An or...

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...

The Roommate Pt. 11 - Miranda

by ValoryG on Sep 19, 2017
Transsexuals & Crossdressers

Josh/Lori, having lost her virginity to Miranda's penetration, and feeling even more like a woman, settled into teaching again. The rewards of passing on his passion for literature to young students was considerable, and now he could increasingly see characters from male and female perspectives. He was especially interested in learning how his female student...

Nico's Girlfriend Pt. 05

by SissyDemi99 on Oct 12, 2020
Transgender & Crossdressers

After the game against Central had almost 100 students in attendance to once more watch Jill steal the show, the soccer team became the talk of the school. Every guy in school was jealous of me because I was dating Jill. She was one of the hottest girls in school and she showed up every team we went against. We were the star couple in school, and life couldn...

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

Smoking Blues

by sissymissyct on Mar 26, 2019
BDSM

"Hey Bren," called my assistant Sarah. The home office called while you were out smoking. You Better call Mr. C back. He didn't sound happy!" "Okay, thanks dear. I will call him back straight away," I replied as I headed to my office. As I was opening my door Sarah continued. "You know, you really have been taking a lot of smoke breaks lately. We are all co...

The Abdominal Snowman

by Cashmere_Snow on Jun 1, 2020
Sci-Fi & Fantasy

This is the second story in The Erotic Adventures of Chastity Summers. It follows Romancing the Raptor. ** Chauncey Adams started the day with a light breakfast of coffee and toast, explicitly avoiding any added sugar or cream or condiment that might irritate his bowels on such an important day, but, with each exhausted, stumbling step through the darkness...