Sissy Fag Stories

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AliExpress and Sissy Downfall Pt. 02

by His_fag_wife on Oct 15, 2017
Transsexuals & Crossdressers

Charlie had really done it this time, deciding on his first big self bondage session in his hotel room after picking up all his kinky goodies he bought on AliExpress. Then his wife had surprised him by joining him for the weekend and found him, fully dressed as a Sissy slut, make up, wigs, high heels the lot. Locked in bondage at his own hands. Now she was a...

Carol, Candy & the Ex Pt. 01

by corduroysissy on Mar 26, 2019
Transgender & Crossdressers

It was Monday night and Davie was bored. He'd grown tired of all the online political bullshit, there were no movies worth watching on Amazon, he didn't feel like playing a mindless video game and he was a little too drunk for reading. He decided he'd jerk off with one of his corduroy skirts and call it an early night, but before getting to the bedroom his p...

I"M Not, Really, I'm Not Pt. 02

by gbr2004 on Sep 14, 2020
Fetish

It's Saturday and I can't stop thinking about having to go out this evening and having dinner with Mr. Grant but I know there is no way out of it. I'm watching a game on tv when the doorbell rings. When I answer it, there are two men standing there. One is holding a couple clothes bags and the other several boxes. 'Are you Steve?' and when I answer in the a...

Trip to LA

by gbr2004 on Sep 15, 2017
Fetish

The bar at the Hyatt in LA was about half full, mostly businessmen with a few couples scattered around. I found myself a seat at the bar and started looking over the crowd. Look like it was going to be a tough place to meet a babe in, probably would have to go out somewhere else later. I'm married but that hasn't been going to smooth lately so thought the tr...

The Ex's New Toy Pt. 02

by Urtoy2be on Sep 15, 2017
Fetish

Dearest Dana, I am writing to talk to you about things that I am unable to say to you face to face. I want to go back to when we were still married and come all the way up to current date. Maybe you will, hopefully, like what I have to say. Maybe we can come to an agreement/arrangement that could be mutually beneficial and satisfying to everyone involved....

What Every Sissy Knows

by BelissimaSissy on Jul 31, 2018
Transsexuals & Crossdressers

Note: the following story is about 99% true with only minor embellishments. For example, there are no condoms in the story. In real life, protection is a must, but stories give us room to fantasize. Enjoy! ***** I was scared but it didn't matter. I pushed through it until my plump little dick poured out its hot seed onto my tummy. After that all I could he...

Madam Molly Pt. 02

by corduroysissy on Feb 11, 2019
Transgender & Crossdressers

Molly & Jessie's conversation lasted about twenty minutes, and by the time it was over she'd made it quite clear that when it came to obedience her expectation were very high. She then informed him he was going to be her little slave-boy and amuse her for a while. When she was ready to get laid she'd summon her cuck Tracy back and Jesse would resume his boyf...

Kimmy the T-girl

by sissy_in_denial on Sep 16, 2017
Transsexuals & Crossdressers

Introduction: Hello. My girly name is Kim, but in my every day life, I am known as Ken. I am 5"5, 135 lbs. I'm eighteen years old, and this story begins on the last day of school before spring break. I have been a closet cross dresser for the past two years. I started off from stealing my sister's panties and bras and wearing them when I was home, alone, an...

BBC Worship Ch. 03

by CumSlurpingCuckold on Sep 18, 2017
Interracial Love

The time had cum to discuss the full implications of her pregnancy and ongoing relationship with Jerome, whom we both loved and worshiped dearly. Wasn't it time to admit to her family and a few other friends and coworkers who still didn't know? Didn't they deserve to know that the marriage that they had seen us commit to a few years ago was now a sham, that...

Carol, Candy & the Ex Pt. 02

by corduroysissy on Mar 26, 2019
Transgender & Crossdressers

(Will Candy make a good cuck?) Davie was standing at Carol's front door dressed in a pair of copper brown wide-wale corduroy dress trousers, and a beige polo shirt. Oddly enough, he felt more nervous than he did the night before when he was in full drag, and he attributed it to the ex-factor. Last night Davie as "Debbie" was there to meet Robbie as "Candy"...