Sissy Pills Stories

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Julie's Collaring Ceremony Pt. 01

by julieaugust72 on Dec 24, 2019
Transgender & Crossdressers

Please allow me to introduce myself. My name is Julie and I am a very submissive older sissy. I am 5-9, with a soft feminine body. I have been taking fem pills for years now. They have given me a feminine shape with a nice soft arse and 36C tits. I work out very hard in the gym to keep my body tight. But I still have a bit of a belly which people that the me...

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...

The Prostate Exam Pt. 08

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

Please do not read on unless extreme sissification and forced gay and bi scenes, watersports and cum eating, really flick your switches. I don't want to offend anyone so thought this comment might help. ***** It'd all started with a routine visit to his Doc for a simple prostate exam. His Dominant female doctor had pushed her finger just into his ring and...

Making Francesca Ch. 02

by Spango on Sep 12, 2017
Transsexuals & Crossdressers

While slowly beginning to come to, Frank heard low voices somewhere off in the distance, but was unable to make out what was being said. As the grogginess began to wear off, a flood of memories came rushing into his mind; getting drunk at the bar and being caught wearing panties, being Tazed on his front porch, waking up chained to a wall in an S&M dungeon w...

Daddy's Sissy Staircase Ch. 03

by SissyLoniOR on Sep 28, 2020
Transgender & Crossdressers

This is part 3 of a 3-part series, to understand better, go back and read parts 1 and 2. Thanks for everyone's comments, this has been my first story here at Literotica, and I have ideas for many more. Please feel free to contact me with ideas for future submissive sissy slut stories! My visits to Daddy now typically involve more time than just during the...

Cyber Sissy Ch. 05

by missvicky53 on Sep 25, 2017
Fetish

A fantasy by Miss Vicky Part 5 (The Last One) The rest of the evening passed with the two of us cuddling on the couch, each with a glass of wine. Megan had changed into a black floor length nightgown with a lace inset running diagonally across the front. This meant that with each movement of her body, I would catch a glimpse of various parts of her body. T...

A Very Public Sissy Adventure

by DivinaTellsAll on Jun 4, 2019
BDSM

At Madame Vega's instruction I had spent the last hour edging myself. This is not always an easy task for a sissy who is not allowed to stroke her clitty. The edging was primarily accomplished by the use of a vibrating wand inserted in my fuck hole, and an Hitachi wand that I could rub my clitty on, as I teased my fuck hole deep inside. I had been banned fro...

Subliminal Obsessions Ch. 05

by Sissyhalo on Sep 14, 2017
Transsexuals & Crossdressers

Sarah's right they'll watch anything. Including me sleeping. I don't feel different sleeping with the videos going and listening to everything but that's going to take awhile if at all. I do feel my jaw though and my bum. Sarah and I paid a lot of guys yesterday to let us suck all those gorgeous cocks and then fuck us blissful. I had so much cock in me...

Steve to Stevie to ?? Ch. 08

by gbr2004 on Sep 19, 2017
Fetish

Ms Storm has exposed me to my boss, showing her that I'm nothing but a sissy faggot. It was so embarrassing. Then she watched as my Mistress took my virgin asshole. Ms Storm talked to my boss, Ms Hunter, telling her that she wanted her to keep me in line at work and make sure that I remembered my place while at work. She gave Ms Hunter permission to use me i...

Sindys Undoing

by SindySuxALot on Sep 26, 2017
Transsexuals & Crossdressers

Lucy had been following Dr. Cornelius for months now. He had been one of the 20 endocrinologists in Orlando on her list when she started this quest, and he seemed to her to be the most likely candidate to help her with her goal. She had ruled out almost all of the others after delving into their backgrounds. From what she could tell in her research, Dr. Corn...