Permanent Chastity Sissy Stories

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Infinite Scroll

Hero Losing Himself

by lol159 on Jan 8, 2019
BDSM

Since Mark was a kid he dreamt about being a hero. He wanted to be someone who did the job on his own. He wanted to be the macho just like his hero The Jaguar Man. He was the proudest man about himself. Having been grown up in an orphanage after his parents were both killed by a robber, he knew best that no kid deserved to lose his family. That's the reason...

The Awakening of a Sissy Pt. 11

by sissyjolie4u on Jul 13, 2020
Transgender & Crossdressers

We had been driving in silence for about 10 minutes, with me reflecting on the changes to my home and the 2 men I was going to be meeting. I was both excited and nervous about meeting with Roy and Ronald. Mistress Di broke my thoughts stating "I think Nikki has done an excellent job with her house transformation work, don't you agree Jolie?" I looked over a...

Sissy Girl Forever Pt. 03

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

Sissygirl forever continued. Sara stood there laughing at me as Mistress explained how things would be for the near future. She told Miss Andrea that if I wished she could fill them in with the red right now if I wanted. But Mistress said no. She was looking forward to my rushing off to work at times forgetting to polish them. Or eating out with friends and...

The Dominatrix Order Pt. 02 Ch. 04

by Jwwsmith on Feb 11, 2019
Transgender & Crossdressers

Protestors swarmed the streets of Femininus on what was the anniversary of the initial passing of the 23rd Law. It had recently been considered for repeal and been upheld by the Council of Goddesses. The protestors demanded that the 23rd Law be repealed and that same sex courtship be legalized. The predominantly liberal crowd congregated before the steps of...

Neighbourhood Terror to Sissy Pt. 07

by Fibaro on Apr 23, 2019
Transgender & Crossdressers

Mark regained consciousness when Stephanie pressed her lips against his and started pushing his load of cum in his mouth. He had only just sucked a load off of Linda's toes and now he was swallowing yet another one. Every time he came here he seemed to get stuck with a taste of cum in his mouth. Only made worse by the way in which he was fed the load. Well a...

An Expensive Addiction Ch. 03

by NeverGuessWhatsNext on Sep 16, 2017
Transsexuals & Crossdressers

The Friday after my second encounter with English was just as eventful as I had thought it would be. My girlfriend got to town, and since we hadn't seen each other in weeks, she was hornier than hell. I picked her up from her parents house around 5 and we went straight back to my place to have sex before going to the party. A couple of months after we starte...

First Time Sissy - The Bike Path

by Phillysissylexi on Jun 15, 2020
Transgender & Crossdressers

My roommates had gone away on a trip for a week, so I had the house to myself for a few days. I had been waiting for a moment like this. As soon as they left I went to my closet to find all my girly clothes, toys, makeup, heels, and lingerie. I couldn't contain myself. I was so excited to turn myself into a sissy. I turned on some sissy hypno to listen to wh...

Samantha Meets a Dom Master

by SamanthaSatine on Sep 16, 2017
Transsexuals & Crossdressers

A true story - I am the main character and all the various activities described were undertaken with my consent...no harm came to me in any way... ***** The date was fixed. The room was booked – neither of the willing parties could accommodate, a not unusual event in the world these two inhabited from time to time. The morning of their meet had now arriv...

i am Kevsfrannie

by Kevsfrannie on Sep 17, 2017
BDSM

i am Kev's frannie, forever bound to the Woman who has both blessed -- and cursed - me with my unique fate. Part 1 i first met my Keverly more than 25 years ago, when i became Her boss at our work. As a professional, i had strong boundaries about appropriate workplace relationships, so for a year and a half i was unwilling to recognize what was otherwise o...

The Training of Sissy Paula Ch. 6

by submissive~pet~ on Sep 14, 2017
Fetish

My Mistress goes to a lot of trouble to fix my nails, hair, and makeup. Once she is done she tells me to follow her. I follow her to the car as instructed. Paula take off the panties. Yes Mistress Candy. Now for a very special long trip Paula. Where are we going Mistress Candy? You will see in about 3 hours sissy. O.K. Mistress Candy. Now I want that assh...