Sissy Petticoat Training Stories

43,339 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Behavior Modification Institute Ch. 10

by NancyPan on Sep 12, 2017
Fetish

Although I continue to receive some demeaning and aggressive comments, most feedback has been positive. I appreciate all who enjoy this story, as we share similar fetishes. If you are not interested in FemDom, male feminization, and sexual humiliation, do not bother to read this series. ***** I was standing with my petticoat and the skirt of the maid's uni...

Sissy Sisters

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

This was the letter I wrote to an older Sissy in an attempt to convince Her to accept me as Her littler sister and use me. * Stop, You make me blush. I too luv wearing feminine luxurious things. I believe now I need to wear sensuous feminine things under the direction of some one else. Could that possibly be You. Please. You would treat me like a little...

The Computerized Bed

by submissive~pet~ on Sep 14, 2017
Fetish

The year is 2020 all sorts of new inventions have been created. The time machine in which John Paul traveled was from the year 2002. He had no idea what was in store upon his arrival to the future. His machine carried him into a large bedroom. It was a very lovely room done in pinks and light blues. The bed was enormous in size, 4 times the size of any he...

Behavior Modification Institute Ch. 09

by NancyPan on Sep 12, 2017
Fetish

I want to finish the story since I have some avid readers and I don't want to leave you "hanging," so to speak. However, I've noted a significant drop in the number of votes and the rating of the last couple chapters - so if you want to encourage me or have constructive suggestions, please vote and/or leave a comment. ***** Confined to the cage and in tot...

Behavior Modification Institute Ch. 06

by NancyPan on Sep 12, 2017
Fetish

Ms. Panington screamed and pushed me from her lap. The arousal monitor alarm was blaring. Ms. Jensen leaped to her feet and ran to Ms. Panington's side. Upon seeing the mess, she shouted, "Naughty sissy! Didn't you hear the alarm?" I lay on the floor ashamed and humiliated. I had heard the alarm begin to sound, but I so much wanted to cum I had thrust my co...

Sissy Chantel, New Reality Ch. 09

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Nine: It's Friday, I Have a Full Shift to Pull Today and Tonight. At 7:00am sharp we are all waken up. This is our daily wake up call and soon sissy Traci as our dorm room's head sissy maid has us all up and ready to go to our morning routine which will be a group enema, group shower, shave face and when need be the rest of our body hair then to do...

Sissy Chantel, New Reality Ch. 07

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Seven: At 'The Agency' and I'm Off to a New Start In My Sissy Life. "Girls this is your new dorm mate, Sissy Chantel." one of the security staff says. The other staff member adds, "You shall take her into your group, help her set up her things and then take her around on a tour of the facilities and such. Report to the office after doing so, OK?"...

Halloween Pool Party Pt. 06

by sissymissyct on Sep 14, 2017
Fetish

I was exhausted and slept until 5pm when I was awakened by a gentle kiss from Miss Annie. She took off my headphones and rocked my shoulder a bit. "Come on my sweet sleepy sissy, it's time to get you up and about. We have a fun evening planned for you baby girl". I rubbed the sleep from my eyes and saw Miss Annie's beautiful face looking down at me. "lets ge...

A Game within a Game Ch. 02D

by doberinca on Sep 16, 2017
Transsexuals & Crossdressers

Author's Note: This is the second story. I still have sometimes trouble to find the right syntax. I hope you still have fun in reading this second story. A third will be following. The characters involved will appear more 'human', not real good and not real bad, and make sometimes bad decisions. Chapter 2D. Another session - or not. The next morning...

Sissy Chantel, New Reality Ch. 03

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Three: More Fun and a Deeper Push into a Reality. [10:15pm] My phone rings, I look to see who is calling me and I see it is Master Camron. I dutifully answer the call, "Hello, Master, sissy Chantel at your service." "Hey sissy, I need you tomorrow morning, that will not be a problem I suppose?" He asks. I reply, "Oh no sir working afternoons or...