Becoming A Sissy Stories

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How to Become a Sissy/Cuckold

by Quietoldie on Sep 14, 2017
How To

This is a How To Guide for Sissies and Cuckolds. Please do not read this guide if you have no interest in the cuckold/sissy lifestyle. Like most couples these days both partners will be doing demanding full time jobs. Traditionally husbands have done gardening, cleaning the car, putting out the trash, performing do it yourself jobs around the house, drivi...

Becoming a Sissy Maid & Slut Vol. 06

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Twelve: Chantel's day off. Ohhh, and ahhh as I awake and stretch in my bed. Mmm a blissful sleep where I see the clock and that it's actually 10:00am. At first I freak out a little bit as it normally would be very late for me. But I soon realize Master has allowed me a blissful and free Sunday off. I then get out of bed, my butthole is sore from the...

The Clothes Shop... Pt. 01

by Manndee on Apr 10, 2018
Transsexuals & Crossdressers

I looked at my watch, "Fuck it...nearly six, ...I bet they will be closed!" I parked the car and walked towards the shop. It was raining, it was cold, a typical January Saturday. "Bradley will fucking kill me if I forget my suit!" I smiled to myself. "The man's a dick for getting married anyway!" I walked towards the door, 'Fuck, is it open?' The lights we...

The Dominatrix Order Pt. 04 Ch. 04

by Jwwsmith on Apr 23, 2019
Fetish

Slave boy departed the docks and stumbled back to Femininus, dazed and in despair. He had no idea what to do. He had made the arduous journey, both physical and emotional, to becoming a slave of Femininus, suffered so much heartbreak and rejection to finally find his perfect Mistress, only to get to spend such a brief time with her before she was taken so ve...

My Husband a Pornstar Ch. 04

by gtanya on Mar 21, 2018
Transsexuals & Crossdressers

Chapter 4: Conclusion Here is a small brief of what has happened till now: My fairy husband had been seduced by a strong man at home and then had agreed to be a sissy pornstar. Fairy new master had trained him as a sissy to perform in a gay movie without his knowledge that he was making a sissy trainer porn movie the whole time. I found out and threatened...

The Journey

by born2srvtv on Sep 19, 2017
Transsexuals & Crossdressers

Tom couldn't believe he was wearing a CB-6000 chastity device while driving to Knoxville to actually meet face to face with Jason. He and Jason had been chatting on a kink oriented website for the last few months. Jason had asked him to buy the CB6000 and Tom found himself incredibly eager to comply with Jasons' desire. Jason had asked him to wear it while t...

Mistress Kate Pt. 03

by corduroysissy on Mar 14, 2018
Transsexuals & Crossdressers

Jordan was in a daze. He was dressed in full drag with his face made up pretty and the feeling of sissy submission was wonderful, he hadn't felt it in a long time. Everything he'd experienced since ringing Kate's doorbell excited him tremendously, and even though her demand that he be a cock whore for all her slaves was disconcerting, he felt thrilled to be...

The Landlady Pt. 01

by Manndee on Apr 3, 2018
Transsexuals & Crossdressers

I had been lodging at the address for 7 months now. When I first saw the advert, it made me smile because the lady advertising the room seemed to be so eager to have a lodger. You could see it in her photo. It was not my first choice when I looked through the properties that were available online, but it was the cheapest, and funnily enough, it looked the ni...

Sissy College Ch. 02

by MasterJW on Sep 11, 2017
Transsexuals & Crossdressers

All Characters 18+. Sorry for the delay. Life gets in the way sometimes. This is a sissy/interracial themed story - if these themes offend you, or you are unable to separate fantasy from reality, please read no further. Special thanks to Puzziboi for all her input. I love hearing about the mess you make in your panties, so please do leave feedback. ~~~~~ L...

Becoming Her Bitch

by HerLittlePiggy on Sep 13, 2017
BDSM

"Take it like a man you sissy bitch," Jennifer said as she thrust her big strap on into my ass. "Yes mistress," I groaned as the long life like dick pounded my prostate. "I'm not your fucking mistress you sissy pig," my wife yelled as she slapped my ass hard leaving it stinging and red. "A mistress wouldn't have her cock inside your sissy ass. From now on...