Terror To Sissy Stories

359,934 results
Orientation
Length
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Infinite Scroll

Sammi Meets Teddy

by Sissy_Sammi_ on Dec 8, 2017
Transsexuals & Crossdressers

Ever since Sammi was born Sam had been working his ass off, both in pants and panties. His grades in school improved rapidly as his outlook on life improved, and before he knew it he had sent away college applications and received acceptance letters. He knew where he was going to college, and before he knew it he was graduating. The rest of the year coasted...

Another Submissive Slut Ch. 10

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

The sleazy Indian clerk wouldn't leave. As soon as I let him into my place he made himself at home. At first I was afraid that he would force himself on me but after watching him indifferently trash my apartment I was wishing that he would do whatever it was he wanted to do and go. I stood helplessly fuming as he rummaged through my belongings. I couldn't...

My First Time as Sara... Pt. 03

by Sexy_SaraCD on Sep 18, 2017
Transsexuals & Crossdressers

I've been with Steve for a couple of months and to say I've been happier than at any time in my life would be a gross understatement. Being with Steve has been an awakening. I'm no longer afraid of life. I was shy and timid as John. I didn't make decisions. I didn't take the lead in anything and was easily bullied. My ex fiancé was the worse bully. As Sara...

Young Sissy Ch. 03

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

"Pleez...por favor...pretty pleez...fuck me..." I looked up at her with tears in my eyes, pleading to be penetrated. I didn't have to beg...nothing in the world would have stopped Lola from spraying her seed deep inside my ass...but I know it's what they wanted to hear. I regretted it immediately...well almost immediately...nothing can take away from the pur...

Neighbourhood Terror to Sissy Pt. 15

by Fibaro on Dec 23, 2019
Transgender & Crossdressers

Chapter 17 "If you don't mind watching over the sissies for a bit, I will go look around for the exact outfit I have in mind. I don't trust Stephanie to get it just right. You will be fine watching over the sissies, right? If not, you can always call out for me, but I am sure you are going to do great." Linda said to Lisa who was still getting her feet wors...

Sissy Life Pt. 03

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

Put simply, I was terrified. Things were escalating beyond what I had ever anticipated. I had been serving my wife, my Mistress as a sissy now for about 3 months. Every minute away from work was spent serving. The first month was good fun. I enjoyed being dressed and it was a bit like living out a fantasy. That changed when my Mistress decided I would be mor...

Neighbourhood Terror to Sissy Pt. 13

by Fibaro on Oct 7, 2019
Transgender & Crossdressers

Chapter 15 Only 10 minutes had passed since they left from the homeless shelter and they were already pulling up in front of CC's. Mark had had no time to process the humiliation he just experienced yet while he was already getting confronted by a whole new sense of dread creeping up to him. He knew Lisa meant well, but he was also sure she would get corrup...

Natalie on Sunday evening

by natalieukcd on Oct 19, 2020
Transgender & Crossdressers

I spent the rest of Sunday cleaning the house and myself and removing Natalie from the male me, yet again, putting her away in all the little hidey-holes i had. I couldn't hide the lack of my body hair, nor the cock cage from my wife. She had seen the cage so knew it existed but she didn't like it. It 'made my cock look like a mugger' she said. After that I...

Young Master Ch. 05

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

I was running through the mansion, being chased by something so horrifying that I didn't dare to turn around and see what it was. I tried to find my room, but the once familiar hallways were now disjointed and strange, as if the building had be rearranged and some pieces had been replaced with imitations that had a sinisterly artificial look to them. My purs...

Neighbourhood Terror to Sissy Pt. 07

by Fibaro on Apr 23, 2019
Transgender & Crossdressers

Mark regained consciousness when Stephanie pressed her lips against his and started pushing his load of cum in his mouth. He had only just sucked a load off of Linda's toes and now he was swallowing yet another one. Every time he came here he seemed to get stuck with a taste of cum in his mouth. Only made worse by the way in which he was fed the load. Well a...