Sissy Cumslut Stories

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Turned So Totally

by gbr2004 on Oct 8, 2019
BDSM

It was our first actual meeting. We had emailed back and forth about what we were both looking for and found we had similar interests. He wanted to take a straight acting guy, take his masculinity away and turn him into his submissive sissy bitch. That is what I had been thinking and fantasizing about continually but could I actually do it? From our email ex...

You vs. Bully: Your Crush's Heart

by Joggles44 on Mar 27, 2021
Erotic Couplings

[Author's Note: In case anyone is confused, I moved a storyline. I got confused and accidentally wrote several chapters in the wrong path so I have had to adjust it. This may be very confusing and I will hopefully make it as seamless as possible.] [Author's Note: This story is still being written and the game function is still being adjusted. As a result, yo...

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Sissy Whore Pays the Rent

by FrillyMaid on Sep 15, 2017
Transsexuals & Crossdressers

I walked in from the rain, and was confused by the silence. Normally my Mistress would be sitting in the living room with a glass of red wine and her favourite show on, but instead the room was empty and silent. I walked to the kitchen and saw a note on the worktop. It said simply "wear the clothes in the bathroom and come upstairs". Walking to the bathroom...

Introspection

by edibles123 on Sep 16, 2017
Transsexuals & Crossdressers

I pulled the black Chevy Suburban over to United arrivals lane at Bozeman Airport. I was late and she was already outside waiting with her two large brown suitcases and a smaller black one. Jesus, she brought a lot of gear for a short ski weekend. She was also shivering. Maddy was always cold. Her tall, skinny body and low body fat made her an easy target fo...

Black New World Order

by Wildone101 on Oct 14, 2018
Interracial

(Quick Disclaimer: This story will contain a lot of triggering fetishes. Things such as cuckoldry, raceplay, light BDSM, bisexuality, sexual domination, bimbos, racial superiority, and other things of the like. If any of those offend you, this may not be the story for you. Also, I'm not that good of a writer. I just want to get the outline out there for the...

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Covid 19 - Pete Turned into Charleigh Pt. 04

by His_fag_wife on Jul 27, 2020
Transgender & Crossdressers

Red unlocked the locks, unclasped the clasps on the box and then popped the lids back on the two bottles of poppers, but popped them in place for later. After this first session being so much of a hit, she thought Charleigh might be in the box for some time, every day for the coming weeks, if the lockdown remained in place for that long. At least then the du...

A Sissy's Forced Gangbang Pt. 01

by sissy77 on Dec 3, 2017
Transsexuals & Crossdressers

I have always seen myself more feminine than most guys I grew up with. Slim and hairless throughout my body, more curvy than muscular. Until my early teens (I am 25 now BTW), being a sissy for me meant not being masculine as other guys both physically and mentally. When i reached my early twenties it turned to me brainwashing myself through sissy hypo vide...

Another Submissive Slut Ch. 04

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

She was leading me unerringly to my place. How did She know where I lived, I wondered briefly before the effort of walking with such a large plug in sissy hole forced my attention else where. Panting more from nerves than the walk I quickly opened the door to the building to get us in and off the street. Almost immediately my landlady was upon us. I nearly s...

Morning Glory

by dreadknots on Apr 25, 2018
Transsexuals & Crossdressers

Reviews for my last crossdress-y story were pretty good! Hurray! This one is a little more teasing in nature, but is ultimately pretty fuzzy. I am a sap. *** Hardcore Fitness was the classiest gloryhole in town. All the right people knew what went on behind the illusory front of a 24/7 gym, and the syndicate behind its operation paid off the right guys in...

Covid 19 - Pete Turned into Charleigh Pt. 02

by His_fag_wife on Jul 13, 2020
Transgender & Crossdressers

Again it was as though she'd slapped him back into reality, just as she intended, she'd noted his angry response earlier that day and wanted to trigger him again, but trigger him much more this time. She simply would not accept rudeness or attitude from him. Pete had to realize that as Charleigh took over his psyche, that she would need to be more and more s...