Sissy Cumslut Stories

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Introspection Ch. 02

by edibles123 on Sep 16, 2017
Fetish

Chapter 02: The Party We dock at the chalet and Maddy informs me a couple of her friends have already arrived. She attaches a lease to my collar and sternly looks on my eyes. "For the next three days, you are my slave, Jackie, and you will follow my instructions to the letter. I will absolutely not stand for disobedience or poor behavior." I was truly sc...

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...

My Wife Turns Me Out At Book Club

by Godscountry on Sep 26, 2017
Transsexuals & Crossdressers

It's been 3 days since the event, and my mind is still reeling. I can't believe my wife took me as far as she did in one night. Sharon had told me a few weeks ago that the neighborhood book club she attends was having a special couples night. Apparently the wives had discovered that their husbands enjoyed the idea of group sex and partner swapping, and eve...

Sissy Crissi Ch. 02

by sissycrissi on Sep 11, 2017
Transsexuals & Crossdressers

Chapter 2 -- Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and man...

Adult Trip Pt. 02

by cuckcpl4play on Jul 3, 2018
Interracial Love

The trip back to the room was embarrassing given I was coated with the cum of my new Master. I rushed back and within seconds of arriving, my phone went off. The text read, Dearest white slut, please provide an inventory of the sex toys that were brought with you. It is now 4:00 and I expect you and your small dicked cuckold husband to join us on the beach...

Sissy Wants Her Wife's Boyfriend Ch. 02

by SissyArlene on Aug 21, 2018
Transsexuals & Crossdressers

I recently discovered that, just because I am a transitioning sissy husband, I don't have to be docile in the sex department. I am a transgender woman, and I've learned that trans-women have a lot more power over men than most people think. Most people think that trans-women are all submissive, and have no control over their sex life. I have learned diffe...

Becoming a Cock Worshipper Ch. 02

by cock_worshipperr on Sep 19, 2017
Transsexuals & Crossdressers

After sucking Ray he let me use his shower to clean up. He led me upstairs to a rather luxurious master bath, with an enormous marble tub, with expensive looking twin shower heads. Before showering I paused to admire myself in the mirror: I was stunned by my appearance, my lipstick and eyeshadow were smeared across my face, which was also covered in a gliste...

Hypnotized to Try a Gloryhole

by rand0m on Aug 22, 2018
First Time

This is a 100% true story I finally decided to write. I'm not much of a writer or story teller so this was meant to be more of a recollection of the first time I sucked a cock and the story behind it. Although I consider myself straight, I've always been into eating my own cum. Like a lot of guys into this, the idea is a huge turn on but after blowing my lo...

Going Gurly Ch. 01: Cara's Clitty

by anna_subCD on Sep 16, 2017
Transsexuals & Crossdressers

My stories are all true recollections of events from my life, as accurately as I can remember them, with two exceptions: 1. The names of my partners have been changed for their privacy; and 2. I have omitted any references to safe sex, because reading about people fiddling about with condoms is not to my mind very sexy, and in stories you don't need to be...

Sissy for Mommy's Nipple Cream Ch. 05

by ppeaks42 on Nov 2, 2020
Transgender & Crossdressers

The evening after Jaime's doomed attempt at seducing Julia found the young sissy crying into her pillow as she tried to reconcile herself to the whirlwind of changes she'd gone through. Less than two months ago "Jaime" had been nothing but a shared figment of imagination, a character he dressed as for his regular breastfeedings with his mother. When he'd tri...