Crossdressing School Stories

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The Marriage of Martin Hastings Ch. 17

by rik581 on Sep 14, 2017
Transsexuals & Crossdressers

Martin sat alone in a small interrogation room. The large wood table with the two empty chairs on the opposite side of the table were all the furnishings in the room. The humiliation Martin had suffered as he was brought through the police station, the giggles, sneers and staring were still fresh in his mind. Though he was told he was not under arrest, he fe...

Aileen Ch. 01

by TiffyKitty93 on Sep 19, 2017
Transsexuals & Crossdressers

~The following is just a fantasy. Any actual names or likenesses to real persons or events in entirely unintentional and coincidental.~ Rain. Oh how I hate the rain. Only bad things have ever happened to me in the rain. Two years ago, when I was sixteen, My parents argued and decided to get divorced in the middle of a rain storm. However what happened in...

Erika's Story

by Quantarx on Jan 20, 2020
Transgender & Crossdressers

My name is Eric and I have been into crossdressing as long as I can remember. The feel of sexy silky woman's clothing has always been a real turn on for me. I honestly couldn't tell you when it started, but I can tell you it has progressed over the years. I have gone through my "pink Fog" phases where I would buy sexy clothing, only to be filled with shame a...

My Senior Year of College Ch. 01

by sexycdman on Sep 16, 2017
Transsexuals & Crossdressers

I was sitting on the edge of my bed, wearing just my blue panties, a matching bra, and a pair of black platform pumps. My dress was in a puddle on the floor where it had fallen as we kissed. Bobby's shirt was off, exposing his hard stomach, and his jeans were around his ankles. His cock was just inches from my face, throbbing with the beat of his heart. This...

Asian Bimbo Sissy Slut Ch. 01

by melltsslut on Sep 14, 2017
Transsexuals & Crossdressers

Soo...where should I start? I'm sitting here now in liquid black leggings, a hot pink crop top, and a carefully teased wig, with D-cup breast forms glued onto my chest. Oh, as well as the special panties my girlfriend designed - for both of us! From the outside, they look like French briefs. On the inside, they're a little more special, if you get my drift....

The Night of My Life

by TheGenderBender on Sep 16, 2017
Transsexuals & Crossdressers

I live in England, and am leaving school this year, and am 18 years old. We've adopted the American tradition of prom, where guys get tuxedos and girls get dresses, and they all go to a party and dance with each other. The prom was in July, and when my story began it was May. People were beginning to ask people to go with them to prom. A few people had girl...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

Story Tags

by Literotica on Sep 18, 2017
How To

You've written your story, edited it within an inch of its life, and are all ready to show it to the world. You open a submission page and – what's this? Story Tags? What the bleep is a Story Tag? The larger any archive grows, the more important organization becomes. Separating stories into our current categories helps connect readers with stories they'll e...

From a Husband to a Dutiful Sissy Ch. 07

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel. Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...

Futanari World

by styxmaster on Apr 16, 2016
Fetish

You wake up this morning to the sight of your younger sister Sarah pulling your covers off of you. "Get up Doug, you don't want to be late for school." You get dressed for school after Sarah leaves your room. you never mind school that much, you mostly get B's and A's in your classes but given the opportunity you would like to just stay home and wa...

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