Sissy Whore Stories

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How To Be A Boi Bitch Lesson 03

by gothicboibitch on Sep 13, 2017
Fetish

Did you enjoy our first fuck together, my darling bois? I know I did. I'm still thinking about it. Are you? Of course you are. And with that excitement, still, such shame. Making your cheeks burn. Making it difficult to look into your wife's eyes. To meet your girlfriend's gaze. You are no longer afraid. You are ashamed. Of what you are becoming. Of her fi...

Yeliza Awakens Pt. 02

by Yelizaveta on May 11, 2020
Transgender & Crossdressers

Part 2 of 2, hope you enjoy. Feel free to leave comments or thoughts. Or not, all good. Part four: The reveal Seeing him fully dressed, submissive, and made to look like a girl, her power was readily apparent. She reveled in it. He was patiently sitting on the bed, waiting for her direction. This power was becoming addictive. She enjoyed it more every ti...

A Sissy's New Daddy Ch. 05

by sissyneko on Sep 25, 2017
Transsexuals & Crossdressers

When the loud speaker blared that Billie had a visitor he was tied to a stool. Billie had become a plaything for a few of the more business savvy residents of Blofield State Penitentiary. When prisons became smoke free buildings cigarettes were no longer the illicit currency of choice. Stamps had come into fashion because they couldn't keep you from mailing...

Taken Too Far Pt. 02

by SwitchSissy on Mar 10, 2020
Transgender & Crossdressers

"Good girl" He smiled in approval. "Now, I noticed something earlier, when I was clicking that new, secure padlock onto your clitty" he reminded me, pulling me up so I was now sat on the bed, my arms bound behind my back with duct tape. "You've written something there, and on your thighs. And I think I can also see something on your belly button too, you lit...

Casey's Submissive Journey Pt. 13

by corduroysissy on Aug 1, 2018
Transsexuals & Crossdressers

Since Susan had been treating him so nicely, Debbie suddenly felt a little strange when she abruptly walked out. Seeing the confusion on his face, Maxi said. "Don't worry Debbie she has things to do, she'll be back when she's ready to cum again." She slowly smiled. "Oh my, how amusing. Did you think you two were girlfriends now?" She chuckled. "Sorry siss...

Halloween Pool Party Pt. 05

by sissymissyct on Sep 14, 2017
Fetish

We arrived home and Annie greeted us warmly, then stepped back to get a good look at me from head to toe, having me turn to see the full look. Satisfied with what she saw, I was told to bring in my clothes, put them away and then pick something pretty to wear as dinner would be ready shortly. Miss Maddy and Annie headed into the main house and I went about m...

Black Cock Smoking Sissy Slut

by Lisa_Fuckslut on Sep 14, 2017
Transsexuals & Crossdressers

I left the club early. No luck tonight in getting my ass laid. Where were all those hot young studs with their big swinging penises and cum-filled balls when you need them? I had dressed in my sluttiest gear. 6 inch 'fuck me' heels, fishnet stockings and a tight little leather dress. Heavy makeup. Long, thick false lashes to flutter at the boys. Long, sexy,...

Caught in Panties & Dominated Ch. 05

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

Cast Trace - me Tracy - me, dressed en Femme Rick - head of security at work, had just caught me masturbating at work, dressed as a woman Ken - my roommate Ok, ok, I hadn't mentioned this before, but my roommate Ken is gay. He would flirt with me from time to time, even hit on me, and I pretended to discourage him, but sometimes, late at night in my roo...

Turning into His Toy Ch.01

by vaultdweller111 on Sep 12, 2017
Transsexuals & Crossdressers

So this is the story of how I became daddy's plaything. It all started when I was nineteen and my name was David Romero. I was going through a bit of a depressive stage in my life. My girlfriend left me, I was doing terrible at college, and I hated my retail job. The only safe haven I had was the internet and porn, and let me tell you something there was s...

Mommy and Goddess

by force_transitioned on Sep 12, 2017
Transsexuals & Crossdressers

Andrew never saw the noose. He was uncomfortable around his new mother in law - his wife's new step mom. And rightly so - he was, after all, going through the woman's intimates since the day she entered their lives, some two years ago, shortly after the marriage. Had he overcome his guilty reaction, he may have noticed a recurring theme in their conversa...