Sissy Lingerie Stories

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Orientation
Length
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Infinite Scroll

Mistress Chronicles Ch. 06

by MistressMtoyou on Sep 25, 2017
Fetish

Background This story involves my on-line subject Nancy, who I introduced in Mistress Chronicles #4. This subject passed all of the tests I described in "A few good subs", but before we were able to arrange an in-person session, he was offered a job in a town a great distance away, precluding in-person meets. Nancy is a computer nerd. Brilliant at working...

Miss Guided Pt. 04

by MissMarianne on Apr 9, 2019
Transgender & Crossdressers

The next morning I went to Dr. Emily's office for my appointment and reuniting with Charles. When I arrived There were two people talking to the receptionist and I couldn't see her face. Then, I realized that the receptionist was Charles! I heard one of the patients address him as "Charlene." He looked just like a woman. Dressed in a conservative skirt s...

Daddy's Sissy Staircase Ch. 01

by SissyLoniOR on Sep 28, 2020
Transgender & Crossdressers

I've cleared my calendar for the afternoon and going to be spending this time with my fwb Daddy. On the drive over to his place, it got me thinking, he and I have been FWBs for a long time, and this story is an attempt to chronicle how I went from being a newbie sissy wannabe to his addicted, shameless cock slut. This is my first submission ever here; I hope...

Chronicles of Heather Maureen Ch. 10

by HeatherMaureen on Sep 16, 2017
Transsexuals & Crossdressers

Showered and with my hair still wet I slipped on a pair of panties and thought over the last while as I fixed and ate breakfast. I needed to control my actions more somehow. I couldn't go on being the wanton sissy slut every night the way I had been and I certainly couldn't go on having unprotected sex all the time! I just didn't know how. I'd start out wit...

The Pantysissy Diaries Ch. 03

by JPantyboyVSL on Apr 23, 2019
Transgender & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapters 1 and 2 before reading chapter 3. ***** It was nighttime in NYC, and Jaymie and her 6 Mistresses had just left their apartment to head to Vic...

Playing Pregnant

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

I'm a sissy. I used to be a femboi, then I was a crossdresser, and now I'm a sissy. The main difference between the crossdresser and sissy phases was the attitude; before I was a guy doing this for fun and to be admired, sexually – to confuse straight and gay boys alike. But now, as a sissy, I was devoted firstly to my master and love, Noah, and secondly to...

The 19th Hole

by skywayscribe on Sep 12, 2017
Group Sex

Sissy and Michelle were having lunch downtown Minneapolis when Michelle starting asking Sissy how Chuck was at fucking .... Sissy got wet then and there and told Michelle, "If you only knew...." Who knew that would be the beginning of a fabulous experience for Chuck ... and Michelle ... and Sissy. Michelle and Sissy continued their afternoon downtown girls...

The Pantysissy Diaries Ch. 02

by JPantyboyVSL on Jun 5, 2018
Transsexuals & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapter 1 before reading chapter 2. *** The Amtrak train Jaymie was onboard with his new Mistress, Sydney had just pulled into NYC. Jaymie had to get...

A Wife Comes Around Ch. 03

by pinkpanteez247 on Sep 11, 2017
Transsexuals & Crossdressers

Part 3. Sorry it took so long but life gets in the way sometimes. Also had to get the creative juices, along with some other juices, flowing again. I'll try to get into more detail (foreplay), instead of just right into the action. It makes for better reading. * As I sat there and watched, my panties were getting wetter and wetter and I decided to do some...

Subliminal Obsessions Ch. 04

by Sissyhalo on Sep 14, 2017
Transsexuals & Crossdressers

*Before... I open my mouth and pump the last bits out of him and show him and Sarah's sort of become invisible as she recorded all of this. Alberta's standing and staring from the doorway and I show her too and her wide eyes widen more and then I swallow it. I rise up to standing and deeply kiss Leon. "That was perfect, worth all those years working for...