Sissy Pills Stories

15,811 results
Orientation
Length
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Infinite Scroll

Shopping and Sucking

by Subkoksukr4u on Mar 2, 2020
Fetish

Matt was in the kitchen as usual preparing breakfast. He'd been instructed to prepare all the meals according to a specific menu plan each day. He finished the sauce for the eggs Benedict got on his knees and waited. He was wearing frilly pink crotchless panties and a matching bra, his bright pink CB 6000xs chastity device was barely peeking out between...

A Natural Sissy Ch. 04

by harv069 on Sep 15, 2017
Transsexuals & Crossdressers

Author's note: This is a story about a woman who turns an older man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you like the idea, read on, and don't forget to vote and leave a comment. You will need to read the previous chapter to see how we got where we are in this one. More will be added if comments...

Abducted and Turned Out Ch. 03

by dawnib66 on Sep 12, 2017
Transsexuals & Crossdressers

...... So, he walked up and positioned himself at my cum soaked pussy and penetrated me, and as he did I couldn't help but moan and encourage him by saying, "Fuck my pussy". As he was pounding me relentlessly for the next few minutes, he began to tell me about himself. "I noticed you the day you moved in. I knew you were a slutty little sissy then, and I k...

Daddy's Sissy Staircase Ch. 02

by SissyLoniOR on Sep 28, 2020
Transgender & Crossdressers

Thanks for reading and your comments! As this is the continuation of a story, it will make a lot more sense if you go back and read Chapter 1. Almost from the very start of us getting together, there were sex toys and accessories added to the mix by Daddy to make the experiences more and more titillating for both of us. From the beginning, there was always...

X-Change: The Frat House Blues

by MrYowman on Sep 16, 2017
Sci-Fi & Fantasy

The world had been changing rapidly. Maybe for the better, maybe for the worse, that was yet to be determined. But the progressive political movement of the early twenty-first century had definitely made grounds, if not economically, at least socially, especially where sexual and gender norms were concerned. Science too, had made this new world more bold and...

Quenching Thirst

by PutItInMyMouth420 on Jun 19, 2018
Transsexuals & Crossdressers

Warning this story is about gay interracial sex. It borders on sexually deviant and if this offends you I'm warning you ahead of time so you are not reading anything you don't want to. *** I had just turned 19 and was completely in a slutty phase in my life. I was good at pullin bitches, but at the same time, with men, I was the bitch, and I LOVED it. At...

From a Husband to a Dutiful Sissy Ch. 07

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel. Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...

A Mistress to Obey Ch. 05

by gbr2004 on Sep 12, 2017
BDSM

Continuation of this story that involves forced fem, forced bi, discipline, humiliation and submission. Not your thing, move on to another story. * We got back to her house and she opened the car door and let me out. I followed her into the house and she went and set down in her chair and I just stood there in front of her. 'Present sissy boy.' I droppe...

The Writer's Secret Conclusion

by AnnMichelle on Sep 16, 2017
Transsexuals & Crossdressers

Synopsis: Loren had no idea what he was getting into when his agent suggested he write transvestite fiction. Nor did he realize how eagerly his wife Stephanie would embrace the idea of feminizing her husband. How far would they go? * Chapter 13: Laura Blossoms A routine developed. During the weekdays, Kathleen would come over to watch Loren work. They wou...

Mistress Viagra Pt. 01

by Njstraponlover on Sep 13, 2017
Fetish

This story is 100% pure fantasy. None of it ever happened. If you are offended by stories of a mature nature containing references to bondage and humiliation, please do not read. This is fiction!! ***** I had been chatting with a new online mistress for a number of months and during that time she had me buying all kinds of sexy woman's cloths, new sex toy...