Sissy Magic Stories

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Orientation
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Infinite Scroll

Forced Strapon

by trypewyre on Sep 12, 2017
Fetish

One weekend while sitting back in my chair, I was watching a movie. My mind started to wonder when I drifted off to sleep. I awoke a couple hours later to a touch on my shoulder. Knowing it was my kinky redhead girlfriend, I thought nothing of it when I drifted back asleep. A few seconds later I felt a hand slowly move down my chest and stopped on my flaccid...

Gloryhole First Timer

by SluttyChrissy on Oct 5, 2020
Transgender & Crossdressers

This is a true story of an experience I had a few years back. I hope you enjoy! It all started on a random Thursday on my lunch hour. I was feeling especially girly that day and I decided to make a detour to my favorite little adult bookstore/lingerie store. I walked in and slowly browsed around, looking at the lingerie and dresses, just enjoying the feel...

The French Trip Pt. 02

by DrLuverotica on Sep 16, 2017
Transsexuals & Crossdressers

The gendarme's gave the impression they were used to this kind of shenanigans. One of them indicated we should all get dressed immediately. I fumbled about for my clothes, but couldn't find my boxer shorts - so I simply put my trousers over the silk stockings and Jo's panties I was wearing that were now filled with Pascal's cum. Jo rolled her skirt down, P...

Caught by the Past Ch. 03

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 3 - Friends United Previously - When you dressed as a sexy tart for James he showed two sides to his character. Bent over his knee, stuffed with a butt plug and forced to suck his cock. What more could he possibly do?... Read on After sucking his cock you sit on the sofa supported by a fluffy white cushion, shoes kicked off, legs curled under your...

AliExpress and Sissy Downfall Pt. 03

by His_fag_wife on Nov 2, 2017
Transsexuals & Crossdressers

Tim cupped Emma's arse cheek as they went into the hotel room, stroking her, sliding into the cleft of her cheeks, warming her up a little more, not that she needed it. Charlie didn't notice them come in at all. Not that she could really turn her head with the thick COCKWHORE collar padlocked tightly around her neck. The cords attached to the dildo were als...

Just Like My Friend

by purekink on Sep 12, 2017
Transsexuals & Crossdressers

I suppose it all started after my friend told me his girlfriend liked to dress him in her clothes before sex. I couldn't quite believe it - he was masculine and muscular, a real man's man. He'd confided in me and I teased him about it unmercifully. I mean, really? Being dressed in women's clothes? That was supposed to be a turn-on? He seemed to think so, bu...

Rene and Gene

by Bakeboss on Sep 16, 2017
Novels and Novellas

Part l My first Friday as Jean: Although I work at home, I still took the day off to make sure all the housework was done. Rene called on her lunch hour and said she bought a surprise for me, that she felt naughty and wanted us to spend the weekend doing naughty things. I was hard at the word naughty; my beautiful wife is such a tease and enjoys role-playi...

Transforming Brent Pt. 03

by sissymissyct on Oct 8, 2019
Fetish

Over the next few days I removed most of my male clothing from the house and donated it to Goodwill. I met Wendy as she got out of work each day and we went shopping. The first time was for regular clothing. Skirts, dresses and blouses, leggings and shoes and regular lady's sportswear. Thursday it was lingerie night. I ended up with multiple bras and camiso...

Being Holly

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

Okay like right off I want to make it clear it's Holly now and forever. Holt's fucking dead and I'm killing anything that's left. And that's a damned good thing. See Holt was an asshole, I...he...that person I was...I was raised by an asshole. My dad and he wasn't a nice guy. He was a jock, he was a mean jock raised by worse my grand dad. Holt was part...

Town of Hidden Desires

by Birbfinchy on Oct 27, 2020
Fetish

A U-Haul van pulls up outside a beautiful blue house in the suburbs of Setgow. Skylar, just turned 18, steps out of the van and relishes the cool breeze on his face as he stretches' his thin legs after being trapped in the car for the past 4 hours, the wind pushes his neck-length dirty blonde hair past his bright blue eyes which he gently brushes aside back...

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