Sissy Trap Stories

19,529 results
Orientation
Length
Source
Infinite Scroll

Big Booty Goth BF

by Furry-god69 on Dec 7, 2020
Transsexual

You are Damien Smith a 18 year old high school senior who's really into goth culture, your parents say it's just a phase, but you don't think so. you look like a regular teen save for you're dark hair, and very feminine figure. For as long as you could remember you always a very girly frame, which many people made fun of, except for, Avery, the love of your...

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Slow Descent into Sissy-Hood... Ch. 01

by Slipperylock on Oct 31, 2018
Transgender & Crossdressers

Beta boy beginnings. It started when I was online, lonely and drunk. I'd been at University for maybe three months at that point, struggling along with a Masters degree in Economics. Unlike my undergraduate years, I had decided to live alone in a one bedroom flat - I thought that with more privacy would come more focus. What I hadn't counted on was that wi...

Sissy's sister

by acepmn on Nov 21, 2015
Bisexual

Anna had always seemed like a good girl. Our parents weren't suspecting anything bad about her, just like they didn't suspect I was spending a lot of nights dressed as a girl in my room. I had skirts, cute tops, slutty dresses, panties and sexy thongs, butt plugs, dildos, cockrings, vibrators... A whole panel of varied toys to play with while dressing up. I...

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Bitch

by Dennis_St_John on Sep 19, 2017
Transsexuals & Crossdressers

'I am ready, Sir.' I texted on my cell phone. 'Room 28.' A few moments later, the cell phone pinged and a return message appeared. 'You know what to do -- I'll be there very soon.' I took a shuddering breath and looked at myself in the bathroom mirror. An angry frown marred the soft made up sissy face looking back at me, framed as it was by dark straight h...

My Bestfriend's Girlfriend

by Shauna_Wood on Jul 9, 2019
Transgender & Crossdressers

When I was in my early 20's I used to play a lot of online video games. First person shooters, mostly. The Battlefield series, especially. I had started playing games online with a guy named Chris who had gone to high school with my ex-fiancé. He and I had met through her and had really hit it off. We had remained close even after she and I split. He lived u...

Mum & Sister Dress Him Up

by Quietoldie on Sep 14, 2017
Transsexuals & Crossdressers

"This is my rented flat you know Michelle. It's not fair you being like this with me. I've always been good to you haven't I?" Peter says. He often seems to get into situations like this. He was never very good about sticking up for himself. Now his girlfriend is chucking him out just because she found him dressing up in her things. "I just don't want to l...

Voyages of the S.S. Futchia

by Dragant on May 11, 2018
Science Fiction

(The intro and backstories are the only parts not in the first person) [Captains log (haha log) Stardate... whenever] These are the tales of the Starship Futchia and her crew. They have been together on more unfortunate adventures than most in the star sector. They have traveled across more space than many meteors and they have fucked/been fucked by more ali...

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Moving to the Sexworld

by Shendude on Dec 19, 2010
Science Fiction

Imagine an alternate universe where casual & free sex, sexuality, & nudity are everywhere, where all people are at least bi, where there are almost no sexual taboos, where everyone's a nympho or satyriac, and where almost all interpersonal interactions have some form of sexual content, and it has ALWAYS been this way. Now, imagine that this world com...

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Getting What You Want

by lowtouch on Apr 5, 2021
Transsexual

You don't know why they always pick on you, the guys who live in your building. You never give them any trouble when you pass by on your way out the front, where they like to stand in their sweats, either working out or hanging out, but they never let you go without something. Usually it's a just a comment, or blocking your path and making you shuffle around...

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The Trap Ch. 04: Paula's Debasement

by Paulateevee on Apr 13, 2020
Transgender & Crossdressers

Due to the current situation with COVID-19, I've been able to get this part out a lot quicker than I would have normally. In this part Paula's life changes forever. The usual disclaimer applied. Everyone is (well!) above the age of consent. This story is about crossdressing. If that's not what you like how did you get to this page. I hope you enjoy. Paul...