crossdressingstories

Teacher's Crossdressing Challenge PART 1

The Wellington Academy, I couldn't believe it, yes, I had my Master's in Education to go with my Bachelors in Rhetoric and Composition, but I was a first-year teacher with no classroom experience and Wellington was the most prestigious private sch...

A housewife in the making

I wrote this story a while ago..

She had met Peter on an adult meeting site. He commented on her pictures with flattering phrases like,

"You look beautiful."

"I wish I was there holding you."

"Very attractive legs."

W...

Fuck Buddies

Bobby didn't call right away, but when I checked my messages after my date, he'd finally replied casually to my earlier messages. I replied back, and the next few days passed with regular messages getting increasingly flirtier until they'd become ...

A little treat

Being a bisexual MtF crossdresser puts me in demand with some people and I wanted to tell you about a recent encounter that I had. I was contacted by Minnie, a genetic female friend who I have known for a year who models as a hobby. Minnie and I h...

She found my stash

She was still in shock. She just found her lovers hidden stash. Porn was one thing, whatever. No, this was a collection of womens clothes. Panties, some sexier than ones she owned, garter belts and nylons, silicone breast forms, bras, a wig, dress...

A Wife finds out

"Hello again, Kyleigh!" he said as he looked at himself in the mirror after carefully pulling on his very expensive human-hair wig. Ky Finley was now Kyleigh Finlay and she felt this wonderful rush of endorphins flood over her as she looked at the...

Day Dreaming

I love to fantasize; it is one of the greatest things on the face of the earth. I have many fantasies, tho I have given up on a couple since I married my wife. I am a white male of 27 years, and since I was sixteen, I have had many erotic fantasie...

To Be A Women

I really loved my wife; she was the most beautiful creature I have ever known. Tall, blonde and the longest legs you have ever seen. Debra's beautiful face is framed by her gorgeous brown hair. She was about 5'8" and had a great ass. Her curves we...

Dormitory Fire Drill

The bed in Beverly's dorm room was narrow. It forced their naked bodies close. That was fine with Les, it increased the intimacy. As they spooned together, Les's arm draped across her waist and fondled the bottom of her left breast. His face press...

Crossdressing for the first time

My life at school was fairly uneventful. I wasn't brilliant academically. I wasn't a talented sportsman, actor or musician. I wasn't one of the popular children. I wasn't in physical fear from bullying, although there was a lot of teasing, name ca...

Truth or Dare Crossdressing Story

Ringgggggg... Ringgggggg...

"Sean, can you get that?"

"Hello? Hey Gina... what's wrong? Ok, hold on, I'll get her..."

"Katie, your sister is on the phone. She seems really upset and said she needs to talk with you."

When I ...

Quick Panties Story

Her name was Julie, and she worked the security shift before me. She was tall, thin, and absolutely gorgeous. She and I had flirted many times, but nothing ever came from it. I was pretty sure she was a lesbian, so I never made a move.

My fa...

A Picture Perfect Sissy

"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie."

Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if w...

A Special Surprise

I first met Jake a year ago. He stepped into my shop to spend some money that he had for his 18th birthday. He was a nice lad. Short, effeminate looking with shoulder length hair. At first I was not sure if he was a feminine looking boy or a mascu...

HAPPY PRIDE MONTH!

Happy pride month everyone! I will be at the NYC Pride Parade today. Make sure to go out and represent!

Open Wide

"Turn your head slightly to the right," she told me.

I turned and my face bumped up against her left breast.

"Oops, don't you bite that now," she said.

"I wouldn't do that," I replied.

"You better not 'cause you'd make a ho...

Do you wear girls underwear?

"Do you wear girl's underwear?"

The question caught me off guard. Wendy and I were headed to Champaign, where she was attending an orientation at the University of Illinois. She had invited me, and since I had an enormous crush on her, I acc...

The moment that changed my life

I grew up in upstate New York in a great old city I rather not name here. When I was in my senior year of high school 1984, I started to seriously think about what I wanted to do with my life. My mom was a RN (registered nurse) in a county retirem...

First Time CDing

So, I am a closeted cross dresser. I have never had the nerves or really the chance to explore my fetish with someone. So one day I decided to just cruise the on-line ads. I saw an ad posted by a Fem Dom. As I read the ad, with all fetishes listed...

Crossdressing Fun

I was lying on our marital bed blindfolded with my hands cuffed to the bedhead, wearing a pair of sheer black knickers. I was waiting for my beautiful wife to come home from her date with Antwan, her big black lover.

I thought back to how th...

Caught Crossdressing

With Halloween falling on a Monday, my wife Suzie was busy the weekend before trying to find her costume to wear to work. As a dutiful sissy husband that loves shopping as much as any woman, I tagged along, although our choice of stores to peruse ...

The Punishment

My eyes fluttered around the room as I woke up. I tried to move, but my wrists were bound, stretched out in front of me and attached to the wall. I was on my knees, strapped into a doggy style position. It was Masters trick. Slip something into my...

Kyle The Crossdresser

I am Kyle, a 26 year old professional. I'm 5'11" and 170 pounds and reasonably fit. I don't claim to be any sort of Adonis, but have not had problems attracting women. I shared a 2 bedroom apartment with Quinn, about the same age but about 5'6" an...

Forced To Become A Girl

Oh she is just amazing, truly perfect...

Of course I'm talking about Megan, the girl from my psych class who is just perfect in every way. She's cute, sweet, funny, and all around a wonderful person. She has dark brown hair, brown eyes, and ...

Renting Out A Sissy

Brian sat on the sofa with his head in his hands. Things had gone from bad to worse to terrible in just a few short months. Only a month ago he was happy, he had a good job that he loved and enjoyed. He had a girlfriend whom he adored. The first t...

Wife finds my crossdressing

I really loved my wife; she was the most beautiful creature I have ever known. Tall, blonde and the longest legs you have ever seen. Debra's beautiful face is framed by her gorgeous brown hair. She was about 5'8" and had a great ass. Her curves we...

My Mistress

This all started about a month and a half ago when I was getting bored with all the wannabe Mistress's I'd been encountering online for the past year, finally I had found a women who sounded for real and not only that but she ensured safety and di...

Panty Robber

For more than 7 years, I had been stealing panties from my cousin's wife Tina. She had noticed that they were missing but never really suspected me since I only stole them when there was another possible suspect. She often thought that it was my m...

Losing a Bet

I've always been a bit of a gambler and it's that attribute that has led me into my most perverse and sexual adventure to date. Now granted, I am only eighteen years old and have much more of my life to live but that doesn't make my statement any ...

Sissy Transformation

My wife is 5 years older than I am and we were married when I was just 24 years old. My wife pursued me very hard as she saw something in me she thought she could control. I was really taken by her aggressive nature and found her directness in tel...