Crossdressing Sissy Discover A Craving For Hot Bbc Cum Stories

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"Sissified": 12 Days of Sissy-mas

by silkstockingslover on Jan 7, 2019
Transgender & Crossdressers

Summary: Straight man is turned into a submissive sissy by.... Note 1: This is my 400th story release. To mark the occasion, I thought I would try something longer... mixing many of my themes into one long, complex story. Thus be warned that with over 40,000 words, this story is a marathon not a sprint, and it includes a variety of themes including: cross d...

Sissy Surprise

by silkstockingslover on Jul 18, 2018
Interracial Love

Editor's note: this story contains scenes of gay male sexual content. Summary: Wife discovers her husband is a slut for BBC and... Note 1: This is a NUDE DAY 2018 Contest Story. Note 2: Thanks to Tex Beethoven, and MesaMan for editing this story. - SISSY SURPRISE My husband hadn't been the same since he returned from a six-month military tour. There w...

My New Daddy Ch. 07

by sissytoy20 on Mar 21, 2018
Transsexuals & Crossdressers

After Boss zipped up his freshly cleaned cock, glistening with my spit, he took me up to the 30th floor. My brain was still buzzing with my anal orgasm when he took my arm and basically forced me to walk out of the elevator. I stumbled on my heels beside him, reaching back to finger my cum-filled asscunt. I dug out some of Boss' load and licked it off my fin...

Be My Bitch

by purekink on Aug 20, 2019
Transgender & Crossdressers

I'm so glad you agreed to be my slut – I've been searching for a crossdressing hussy I can train to be my personal tart for some time now, and I'm certain I can teach you to fit the bill. I understand your fantasy is to be dressed as a sexy sissy and have your manhood and your cherry fucked right out of you. This pleases me, as I enjoy nothing better than u...

Panty Posers

by EROTICbearscribe on Jun 1, 2020
Transgender & Crossdressers

PRIVATE PANTY SESSIONS Ch. 01 "Wait! What? Say that again." Doug, my roommate of two years, closed his eyes and took a deep breath. Tension hung heavy in the air. I allowed him to take all the time he needed to explain even though my mind was racing the way it does when your entire world has been turned upside down. I could see he was struggling. It look...

How I Became a Sissy Slave

by Sissy_Sasha on Jul 27, 2020
Transgender & Crossdressers

I had never been so embarrassed in my life. The woman in front of me looked at me with disgust that burgeoned on fear. Seconds prior, I was knocking on her door and ringing her doorbell expecting for a man to answer. This man was Anthony, or at least that's the name he'd given me when I asked. We'd met online a couple weeks ago on a gay dating site. For a...

The Looking Glass

by Son_of_Battles on Jun 15, 2020
Transgender & Crossdressers

This story contains Crossdressing, themes of Gender Fluidity, Exhibitionism, and Voyeurism. If any of this sounds unappealing to you, I welcome you to leave and find something more to your liking. This story is a submission for the 'Love The One You're With' Quarantine Story Event. Please take a second to rate after you finish reading. Thank you to Skye4Lif...

Victoria

by missvicky53 on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 1 My name is Vicki, well that is not entirely correct, my name is actually Jim, but I now answer most of the time to this new name given me by my Mistress. I am writing this account explaining how this came to be at the behest of my Mistress. As I enter this into my computer, I am wearing a lacy pink baby doll nightie with matching panties. My Mi...

HypnoSissy: Cum Cravings

by silkstockingslover on Sep 26, 2017
Fetish

Summary: Videos entrench his hunger for cock and cum. Note 1: Thanks to hfernandez1983 for the story idea and the intriguing revelation that hypno sissy videos exist. Note 2: Of course, all participants are at least 18-years-old. Note 3: Thanks to TexBeethoven, Robert, and Wayne for editing this chapter. Apology: This part was originally announced as bei...

Maiden Voyage

by jessicaj64 on Sep 16, 2017
Transsexuals & Crossdressers

Note to the reader – this is not a work of fiction. It is the story of how one woman found herself, in spite of the odds, and in spite of being born with a male body. It is entirely autobiographical, sometimes painfully so. But having read many tales of transsexuals, which end up being, in most cases, little more than tales about the cross-dressing fetish, a...