Sissy Secretary Stories

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Made to Obey Ch. 12

by madetoobey on Aug 26, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). I'd been forced into a chastity cage and made to wear panties all the time. Furthermore, a curious email I'd sent to "Bowser" before I was married led to my past fraudulent activity being uncovered. I'...

They're My Sister's Wicked Ways!

by grgy56 on Sep 18, 2017
Transsexuals & Crossdressers

Thanks for all the great comments. I know this third chapter has been a really long time in cumming but I hope you enjoy this one as much as the others. ***** So the first time I was caught by my sister, I was dressed in some of her sexy lingerie. That was bad enough but she also caught my best, bum buddy (literally) Chris fucking me and cumming in my ass...

Sexual Harassment

by FrillyMaid on Sep 16, 2017
Transsexuals & Crossdressers

I knew I had gone too far. My secretary had passed my desk, and without thinking I had reached out and brushed my hand along the curve of her bottom. I didn't plan it. I just did it without realising what I was doing. As soon as my hand touched the coarse material of her grey pencil skirt I panicked. What was I doing??? She spun around and there was a loud S...

Webcam Mistakes

by chrissycockslut on Apr 3, 2019
Transgender & Crossdressers

I guess I should've been more careful. But what can I say? I was a young man and I was stupid. I had just passed my 18th birthday a month earlier and I had treated myself to my very first, brand new dildo. Nothing crazy, only 5 or 6 inches long and just 1.5 inches girth with a suction cup base, but it was perfect for a beginner. Luckily, I had plenty of ti...

Recruiting of a Sissy Maid Ch. 07

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Seven: First Time Escorts, Chantel and Traci. Carl meeting with Barlow over morning coffee says, "So Barlow how did things go with Chantel and Traci in Montreal?" Barlow bites a muffin and swallows, saying, "Tony and Vic were very pleased with the girls. Chantel and Traci were great performers, the sex videos were very hard core and as normal with...

To the Manor Bound Ch. 04

by Nikki258 on Sep 26, 2017
Transsexuals & Crossdressers

This probably won't make too much sense unless you've read the other chapters first. Like the other chapters this includes forced feminisation, BDSM, and non-con, so it might not be your cup of tea. Regardless, do comment and email me to let me know what you think, or just to say hello! ***** Chapter 4 - Five Weeks After Transformation Peter held the d...

Women in the Workplace Pt. 02

by MissKateKees on Sep 19, 2017
Exhibitionist & Voyeur

The sound of a scuffle returned Laura to business, Miranda and a group of girls were struggling to drag Ryan onto the stage. He was wild with anger, flailing his arms and shouting in protest. A primitive barbarian. Laura walked over and simply threw her heeled foot into his groin. He went down hard and was dragged long the stage to begin proceedings. "Somet...

A Better Life through Chastity

by chlomo on Aug 31, 2020
Transgender & Crossdressers

I wrapped my arms around Sophie and squeezed her tight as I shot my load inside her. She was perfect; large breasts a peachy rear all in a pale curvy frame, her long brown hair framed her big welcoming eyes gleamed up at me. I didn't deserve her. I sighed heavily and sank into her as she smiled and gently stroked my hair. I had failed her again, I knew it,...

Marriage Scam

by imhapless on Sep 17, 2017
Loving Wives

According to immigration officials, marriages of convenience between Canadians and Cubans has become a significant problem. In a quality assurance exercise in 2011, officials contacted a sample of Canadians who had married and sponsored Cubans. About one-third of those relationships had ended soon after the new spouse's arrival in Canada. Fraud and misrepres...

My First Session with Her

by humbleslave on Sep 17, 2017
BDSM

Let me start out by describing who I was. I am 24 years old, 5'6" about 150 pounds, fair skin and short hair. I'd been cross-dressing for about seven years, and had quite a collection. I was living with a roommate, Jane, who had no idea about my hobby. In fact, I'm pretty sure she'd have been freaked out if she found out, so I'd kept it secret. I consider my...