Mature Sissy Faggot Literotica Stories

351,516 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Fifi La Femme: A Pansy at Last

by pris69696 on Sep 16, 2017
Transsexuals & Crossdressers

I have written this story "Fifi La Femme-A Pansy at Last" mainly from personal experience as a mature homosexual transvestite who was a gay virgin until my early 40s. I hope that it will appeal both to extreme effeminates and the ultra-masculine men they ache to serve. Now divorced I've been living with my boyfriend Ron for three years as his gay wife and ye...

Sissy's Decline into a Slut Pt. 05

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Seven: I've been taken, Made into a Maid, Turned out as a Slut. Two days have passed by, it's Thursday morning. Today Master Gage and Master Martin are to arrive by 10:00am. I awake by 8:00am and my stomach is turning. I get up sit on the edge of my bed wearing my sleeping lingerie today it's a white satin full slip, white lace bra and satiny panty....

Further Training as Sissy Lesbian

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my story 'Miss Johnstone's Lesbian Sissy Slut' and I sincerely recommend reading that story first as it provides background for this one. Enjoy and please take time to give me some feedback! Theo 3. Intermission: Further training Following the loss of my sissy virginity just after I had turned eighteen years old,...

New Rules Pt. 02

by skinnysailor on Sep 23, 2019
BDSM

"Shall we start with this?" The tip of her switch lifts my chin. She's an angel fallen to earth. I look into her beautiful blue eyes. Her long curly black hair tumbles to her shoulders. When she hugged me the satin and chiffon of her robe felt so good. She's blessed with a full figure, mature, but not fat. Her voice, like a soft caress tickled my ear. "You'...

The Photographers Assistant Pt. 02

by panty_wearing_sissy on Nov 13, 2017
Transsexuals & Crossdressers

If you are under 18, please stop reading and delete this document immediately. This story is pure fantasy. It does not relate to any real events, either past, present or future, and is only suitable for persons over the age of 18 mature enough to understand, and distinguish the difference between fantasy fiction and real-life. ***** Jake didn't remember e...

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...

Goddess Rules Ch. 02

by sub_boi on Sep 17, 2017
BDSM

I take him into my mouth and suck him with My soft, wet lips. When he is near coming, I grab his balls and pull down hard, letting his little cock slip out of My mouth. He moans in pain as My hand squeezes harder on his balls. "Now, My little slut, I have a surprise for you." I go to the closet and pull out a sexy little pink camisole. "Put this on, slu...

Sissy Chantel, New Reality Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy. ***** Chapter One: The Journey Starts. Well another night and here I sit dressed in m...

Steve to Stevie to ?? Ch. 07

by gbr2004 on Sep 13, 2017
Fetish

I had returned to work after my first nite with Ms Storm. The night she turned me from a young man to her slave. Ms Storm had came to my work place and had talked to my boss for a long time but I don't know what she told her but my boss, Ms Hunter, had talked to me like never before. Then I had been ordered to return to Ms Storm's house that night. Upon arri...

Suddenly Sarah, A Different Tale

by grizzley123 on Sep 14, 2020
Fetish

Suddenly Sarah, A Different Tale ************************** This is an alternative Chapter 2 to the Suddenly Sarah story I wrote recently. It takes day number two with Sarah in a whole different direction. It likely helps to read the first story. The themes of this story are not for everyone, but for those that like submission I hope you enjoy. As always,...