Share Some Sissy Stories

321,541 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Caught in Panties & Dominated Ch. 05

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

Cast Trace - me Tracy - me, dressed en Femme Rick - head of security at work, had just caught me masturbating at work, dressed as a woman Ken - my roommate Ok, ok, I hadn't mentioned this before, but my roommate Ken is gay. He would flirt with me from time to time, even hit on me, and I pretended to discourage him, but sometimes, late at night in my roo...

Tranny G, Gang Bang Queen, 5

by Creamyirish on Sep 13, 2017
Transsexuals & Crossdressers

I apologize - I had no idea I would continue to write about Chris and Tranny G or I would have numbered the stories. These two beloved people are so rooted in my life and there is so much to share. I never imagined I would share these stories with anyone. Since my husband and I became swingers, I had no idea what my interests would be, I just simply plunged...

Becoming a Sissy Maid & Slut Vol. 04

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Preview: Here is another chapter of my multi-part "Becoming a Sissy Maid & Slut Story." I so hope you all are enjoying this story. I'm no professional writer so excuse me for any writing errors. But I have a flood of sissy maid, slut, crossdressing ideas, thoughts and fantasies to share. I will add more chapters to this unfolding multi-part story now ONE cha...

No More Secrets

by Gemsissy on Sep 12, 2017
Transsexuals & Crossdressers

I couldn't wait to get home from work. My wife said she had something special ready for me. A month ago, she'd found out about all my sissy fantasies when I forgot to clear my search histories. Instead of divorcing me, she did more research and decided to embrace me as a sissy. Now every time I get home, I strip off my suit down to my panties, thigh highs, a...

The Blackmailed Sissy

by jmanrules on Sep 13, 2017
Transsexuals & Crossdressers

Jon walked into his roommates bedroom looking for the phone charger he loaned Eric the night before. As Jon was looking around he saw several pairs of panties, bras, and pantyhose. Not thinking anything of it Jon just grabbed his charger and left with it in hand. After he sat down it dawned on him that Eric has never brought a girl over and even if he did th...

Subliminal Obsessions Ch. 02

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

*Before... She settles into a rhythm hard, steady, deep, hitting my spot inside as I moan and watch the flasher as it shows high speed pictures and all those words and phrases. Sissy. slut, bimbo, be a girl, be calm, be happy, suck cock, be happy, get fucked ne happy, sissy, slut, bimbo, live for men, live for cock, be happy, be a girl, be calm, be happy,...

How I Became a Sissy for BBC

by Caged4goddessd on Mar 12, 2019
Transgender & Crossdressers

It really all started in college. I was a fairly typical and somewhat popular guy. I was involved in a few different clubs and a member of a popular fraternity on campus. Of course, this led to me knowing quite a few of my classmates and at the time I had my share of success with the females in my classes. It was my junior year and at the time I was dating...

Recruiting of a Sissy Maid Ch. 09

by Sissy_Chantel on Oct 31, 2017
Transsexuals & Crossdressers

Chapter Nine: Things Begin to Change for Chantel. Morning time, Chantel awakens and takes a moment to realize where she is and all that has happened. She sits up in the bed and looks over and sees Carl Luftgrin, her mind balances between the thoughts of a wonderful date last night with Carl and knowing this man as her Master owns her. Her mind battles these...

Recruiting of a Sissy Maid Ch. 11

by Sissy_Chantel on Nov 23, 2017
Transsexuals & Crossdressers

Chapter Eleven: People Moving into New Roles and More. Chantel has made her way back to her club dorm room, enjoying the corrective measures of being a Domme over Biff and Marty. She is certain they will be much more mature and even though they still hold powers over the sissy girls like all other male minder/staff, they will better respect what these sissy...

Pink Panties

by DrLuverotica on Mar 27, 2019
Transgender & Crossdressers

It all started with a pair of pink panties. It was sometime after midnight when Jo arrived home from being on-call at the local hospital. She'd received a phone call several hours earlier about a bleeder and had to rush in. Recently her workload had become almost unbearable, but we needed the money so she was working her sexy curvaceous ass off. By the ti...