Sissified By My Cousin Strapon Sex Stories

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The Perfect Choice

by libertinaXx on Sep 25, 2017
Transsexuals & Crossdressers

Andrew had moved in with Hannah a few short months ago and so far everything was going just the way she wanted. She was an endless tease; wearing short skirts and dresses when they were out during the day or tiny shorts and vest tops when they were at home together. She did everything she could to turn Andrew on, and it was working perfectly. She hadn't slep...

Sissified by My Sister

by GreenGale on Sep 11, 2017
Transsexuals & Crossdressers

I will never forget that night. The night I discovered how I truly am. My true self. Its an unforgivable night. And I never thought my little sister would be the one to help uncover this part of me. I was a young, average 19 year old, my sister and I were home from college for winter break. I had short, blond hair and my sister had brown hair cut about at h...

Be My Bitch

by purekink on Aug 20, 2019
Transgender & Crossdressers

I'm so glad you agreed to be my slut – I've been searching for a crossdressing hussy I can train to be my personal tart for some time now, and I'm certain I can teach you to fit the bill. I understand your fantasy is to be dressed as a sexy sissy and have your manhood and your cherry fucked right out of you. This pleases me, as I enjoy nothing better than u...

Vegas Sissy Wedding

by Sissytilly on Jul 6, 2020
Transgender & Crossdressers

Story: Abbie looked up at the clock as she continued thrusting her hips back and forth. Half past 3. 'That messes Wolfie's plan touched down half an hour ago' she thought excitedly, 'he'll be her soon.' As she continued her thrusting she thought back to the start of her holiday... —6 hours earlier— Abbie had arrived at the hotel in Las Vegas with her fian...

A Natural Sissy Ch. 02

by harv069 on Sep 15, 2017
Transsexuals & Crossdressers

Author's note: This is a story about a woman who turns an older man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you like the idea, read on, and don't forget to vote and leave a comment. You will need to read the previous chapter to see how we got where we are in this one. More will be added if comments...

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...

First Time, From A Window

by purekink on Sep 16, 2017
Transsexuals & Crossdressers

You know, I remember the first time I saw you. You lived in my street - you'd only moved in a few months before. I sort of knew you were around, but I don't ever really recall seeing you or meeting you. For a quiet cul-de-sac, we had more than our fair share of single women living around, and we'd formed into a firm group of friends. The first time I saw yo...

My Freaky Life 01

by DickThePimp on Oct 8, 2018
Celebrities & Fan Fiction

This is a super awesome sleazy fuckfest freaky ass sex parody... It ain't real though... Damn This is my new series about me, living My Freaky Life... It's full of sleaze, freaky fucking and fun... It's a huge series combining real life celebrities with TV show and movie characters... There are a lot of people in it, but they will be added gradually... This...

Pegging Parker

by Purple_Parli on Sep 12, 2017
Transsexuals & Crossdressers

Parker answered his phone with his usual, "Yo." "Do you even look to see who's calling when you answer?" Jamie's voice said. "Not usually." Parker admitted. "Why?" "I'd think that when I called, at least, I'd get something a little more romantic than, 'Yo'." He could tell she was just fucking with him, trying to poke him a little to see if he'd respond,...

My White Trash Life Motherfucker Ch. 01

by DickThePimp on Jan 15, 2019
Celebrities & Fan Fiction

Fucked up fuck parody series alert WARNING : The most offensive and depraved fuck parody series ever written... Read at your own risk... If you're not offended then you're one of my fans motherfucker... I approved this fucking message... Read on motherfuckers... This series replaces the White Trash For Life series... Pussy + Moonshine = Life... FUCK YEA...