Sissy Cumslut Stories

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Fine Tuning

by cathynylons on Jun 19, 2018
Transsexuals & Crossdressers

As I served my wife Dominique a brandy in the living room, I noticed that she was looking me up and down with her famous wicked smile. After finishing washing the dinner dishes I returned to the living room to see if she desired another glass of brandy. Again, I noticed her looking me over. I worried that perhaps there was a run in my nylons or that my masca...

Mistress B

by dysfunctionaldreams on Sep 14, 2017
Transsexuals & Crossdressers

I had recently been surfing Myspace and came across a profile listing the owner's name as Mistress B's Sissy Cum Whore. Titles like these always catch my attention and I often go to see if Mistress B is listed early on the friends list of their slaves. In this case, she was so I hopped over to her profile and checked out the sissy application she had there....

The Ex's New Toy Pt. 03

by Urtoy2be on Sep 15, 2017
Fetish

Wednesday afternoon and work was slowing down for the week. Sitting in my office bored staring blankly at my monitor waiting for 5:30 PM so I could cut out. I need a drink went through my mind. The weekend had been a blur. The events with my ex-wife and her new man had been crazy. Fantasies and thoughts had been awakened and now I was wondering who I really...

A Mistress to Obey Ch. 02

by gbr2004 on Sep 12, 2017
BDSM

This story involves bdsm and gay play. Not your thing, move on. * I can't stop thinking about what happened last Saturday. It was so much more than I expected, and frankly, I did things I never thought I would do. I had fantasized about forced fem but still was surprised how different I felt when in panties. It's just hard to feel very masculine when in a...

Center of Attention Ch. 02

by Seethru57 on Sep 16, 2017
Group Sex

Disclaimer: All characters in this fictional story are 18 years or older, and all names are ficticious. This is a continuation series. Debbie Ross was sitting on her bed, writing in her diary about the events of the previous night. She wanted to keep those memories, and hoped to add new ones to the lusty events at Mr. Collin's home. Her thoughts were interr...

Covid 19 - Pete Turned into Charleigh Pt. 03

by His_fag_wife on Jul 13, 2020
Transgender & Crossdressers

"OK off with the wig now and we'll get rid of body hair first and then we can document the necessary changes." Mistress Red pulled off Charleigh's wig, one of the last vestiges of Charleigh's feminine sissy armor and as Pete looked in the mirror, he wondered if he was doing the right thing. With his bald head, flabby pecs and miniscule caged cock, he certa...

Sissy Powers Ch. 04

by ClarasBestFriend on Sep 29, 2020
Sci-Fi & Fantasy

I wondered why I had just agreed to do that? I mean sure, being Leah was super fun, but to eat my own cum out of Clara's pussy was a bit... I'm not sure what it was, but the Yang energy in my soul wasn't super into the idea. That said, the Yin energy I contained was singing like a chorus of angels at the thought of licking a big, hot load of sticky cum out...

Faith Debased Ch. 6

by JordonLynn on Sep 19, 2017
Interracial Love

Author's Comments I was recently called to task for a faux pas I made in chapter 4 concerning a woman's specific anatomy when I described Faith enviously watching Regina's Adam's Apple bob as she swallowed the majority of Cal's hot load. Now, being able to run my hand down my own throat, I am well aware of the fact that a woman does not possess this particul...

A Husband Named Cathy Ch. 03

by cathynylons on Mar 6, 2018
Transsexuals & Crossdressers

When Randy and Brad had finished with me, Brad said, "Well, Randy we have to get going now," and he headed for the door with Randy getting up from the sofa. Before starting to follow Brad, Randy looked at me and said in a soft voice, "Stay away from my boyfriend, bitch." As Brad opened the door he turned and said, "Toni, we have new things at the store, f...

Siss the Bride Ch. 03

by theonewhowas on Sep 19, 2017
Transsexuals & Crossdressers

Every marriage has its problems, even mine, which is a huge problem considering I'm a guy who gave up every semblance of a normal life to follow hidden fantasies on a spur of whimsy induced by my hot older brother. My life during my marriage to my brother has been built upon submission, only natural when you are a sissy crossdresser and when he has the perfe...