crossdressingstories

At Her Service [DOM STORY PART 1]

The paper was done and she marveled at it. The hard work and long time spent interviewing thirteen dangerous people for a psyche report was finally done. Her notes and audio tapes littered the desk, but she was done. It wasn't easy trying to tell a convicted serial rapist to say why he did it. Th...

Drag Queen Night Out

A few dresses, some brassieres and panties are hiding inside boxes in my storage closet around the corner from my unit. A bodysuit made of silicone and having padding at the hips, breasts and lady parts lies hidden inside a another box there. A makeup kit sits on the shelf under the shirts that h...

The Gym Bunny

I've tried finding men to fuck on forums and apps, but the method that turns me on the most, fits into my lifestyle, and yields the best results is through the gym. My dainty, feminine body had always made passing a breeze. Back in LA, I had my pick-up routine perfected.

Eight times out of ...

I became a MODEL online [PART 2]

Part 1: https://youtu.be/Kg7RBiCa-fw

Part 2:

Harry had already arrived at the door. It was already too late to take off everything now. I realized that my secret would finally be revealed. With a deep breath, I went ...

I got a boyfriend

It was Friday night and I was at my friend Ashley's house. A bunch of us had gone over for some beer pong. Ashley was a twenty-three year old blonde with long legs and perky little breasts. She was as tall as I was with a nice ass. I had gotten partnered up with her and we were winning, but with ...

[EXCLUSIVE] CROSSDRESSING at WORK Story

Part 1: https://youtu.be/smIhiO1TOuE

Part 2: https://youtu.be/sfTanwVPcfo

Crossdressed like a LADY PART 2

PART 1: https://youtu.be/Rv1Tw83rcaQ

PART 2: 

Tori has me completely at her mercy. She lifted up my dress so that my ass was exposed on the couch. She said that she really liked my ass. She took her f...

HUSBAND caught DRESSED UP [Full Story]

Lily Abrams had everything going for her. She owned a mortgage with five offices in three cities. She was active in the community and was a volunteer for different charities. It was the middle of the morning and she was headed home to grab the copy of the budget for one of the charities she was o...

Sneaking into a SORORITY party PART 2

PART 1: https://youtu.be/gX2qsjVQCww

PART 2: Sara leaned in and kissed him on the lips. Sara told Jason that she was actually bi and that she was really turned on by Jason dressing up as a woman. Sara continued ...

Wife catches Husband CROSSDRESSING PART 2

Part 1: https://youtu.be/8Q-hRydjM4Y

Part 2: Janice took my hand and led me to our bedroom. On the bed I saw there were a pair of handcuffs. I turned around just as Janice locked the door behind us. Janice said that I was ...

Girlfriend CAUGHT me Crossdressing [CROSSDRESSING STORY] PART 2

PART 1: https://youtu.be/zpp_HGUSqrk

PART 2: Nadia pushed me onto the bed. Nadia was a lot stronger than me and grabbed both of my hands and put them behind my back. Nadia said, “Are you ready to be my little princess.�...

The Raise

First let me set the stage, I am a lifelong cross dresser, since I was 13 and trying on Mom’s things when she was out. I am NOT gay, nor bi-curious, I am heterosexual and this is my story.

My wife travels a great deal in her job, I am lucky and stay home, we have no kids even though we ha...

Transforming Myself

Renton put his hand on the door handle, then pulled it away. He stepped back, shaking his head again. Did he really want to do this? He looked back up at the sign, glowing in classic neon. 'Voluntary Beauty' it blazed through the slight fog that drifted into the harbor district at night.

Th...

The Infection

Mike bounced his legs nervously. He hated waiting, especially in a doctor's office. Not only because of the threat of some grave diagnosis hastily scrawled on a chart lurking on the other side of the door, but also because of the room itself. Examination rooms were not designed for social sitting...

T-girl doing Homework

I'm sitting in my dorm room doing some homework when I hear a knock on the door. "Just a minute!" I put my things down and hop up to get the door. "Hey Kim, what's up?" I ask.

"Oh nothing, just wanted to know if you wanted to hang out?"

"Oh, I'd love too, but I've got all this homewor...

Punishment for being late

"Hi honey I'm home!" I said while shutting the door behind me. It was dark inside the house. I waited for a response but didn't hear anything. I set my briefcase down and slowly walked into the kitchen area. There was a light glow from the candles and my loving girlfriend sitting. She was sipping...

A crossdresser & her lover

I would like to see that in a mirror. Me facing and leaning against the wall with my hands above my head and my legs spread, dressed in my black bustier, stockings and heels. You behind me, running your hands over my body, over my stockings. I can feel the head of your hard cock pressing gently a...

Crossdressed at a PARTY PART 2 [STEAMY]

Part 1: https://youtu.be/AQ7dddcFwLI

Part 2:

When I entered the bedroom, I noticed that there were handcuffs and rope lying on the bed. Maggie smiled and pushed me onto the bed. She grabbed my hands and put them behi...

Waking up as a girl

I woke up feeling especially groggy. My head was throbbing ever so slightly and seemed to be lessening as I awakened. I blinked a few times and my vision became clearer. The night before I had gone out for a few drinks; at least that was my intention. As I looked around the room it was clear that...

Once a year

Imagine me. A slim eighteen year old boy, dressed. I mean Dressed. Dressed up that is, in my sister's clothes. I felt good, very good. In fact I felt incredible. I had done this several times before when my parents had been away but never to this extent. They were away for two nights, visiting Un...

The Exam

I gradually wake, the last thing I remembered was the needle at the end of the syringe sliding into the soft white hairless skin of my forearm, and then I drifted off to sleep.

I am still a little groggy, but I am not worried. I know where I am, what is going to happen to me and what is exp...

THEY DRESSED ME AS A PRINCESS [CROSSDRESSING STORIES] PART 2

Part 1: https://www.youtube.com/watch?v=MkK2Gy-BJWo

Part 2:

Maya put her hands around me and looked into my eyes. Maya said, “You look kind of hot right now.” I smiled and said, “Thank you.” Suddenly, she mov...

Halloween Crossdressing [SCHOOL GIRL EDITION]

Part 1: https://youtu.be/JllYUxBRR3o

Part 2:

Shawn grabbed my hit and leaned in to kiss me. I felt his hand wrapping around the outside of my skirt and grabbing my ass. I hadn’t kissed anyone in a long t...

Kidnapped & Fucked

"Hey! HEEEY! LET ME OUT OF HERE YOUR CRAZY BITCH!"

Tony shouted at the top of his lungs. He strained to free his arms but they were secured tight above his head, tied up in the remains of his shirt and strung up to the ceiling. He was standing almost naked, the only article of clothing prot...

PART TWO: Caught Crossdressing By Girlfriend [CROSSDRESSING STORY]

Hi sisters!

Part One: https://www.youtube.com/watch?v=L6SAMBVuxYM

Part Two:

Alexis stood up and admired me sitting in the bed in her underwear. She asked me, “Do you feel like a dirty little sl...

Becoming a maid

I had recently moved to the Philippines on a retirement visa, being 50 with an early buyout meant I had to be more frugal but I felt retirement overseas could work. Little did I know how far the dollar would go.

After arriving I rented a condo and with utilities my monthly nut was under $70...

Crossdressing Urges

From my teenage years I started experiencing strange urges. When I completed my 18 years I was alone in home. I was in the bathroom and out of nowhere I saw a laundry basket. A pair of my mother's panties was handed out from there. Their red lace caught my eye very strongly and I instinctively re...

Teacher's Crossdressing Challenge PART 4 (FINAL)

Ben kissed her on the cheek and said good morning to Alan. I smiled and nodded at them both. They smiled back with huge, knowing smiles. Ok, everybody knew Ben, and I had humped like bunnies all night. Great.

I sat down and Arthur set a perfect omelet and a nice serving of fruit in front of...

Teacher's Crossdressing Challenge PART 3

"Yeah, Beacham and Tackman are gods, and that new guy is a jerk and smokes too much." I paused. "And just so you know, I'm not sucking any more cocks for a few days." I kissed him on the cheek and headed for bed.

I lay in the darkness thinking about the past week. It had been a hell of a ri...

Teacher's Crossdressing Challenge PART 2

"Well, how did it go? Why haven't you called me yet?" It was Carol on the other end of the phone.

"Just busy with classes and grading papers and stuff, and a little distracted by all the attention I've been getting. It's almost surreal." I laughed.

"Kind of fun, though, isn't it?"