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. The answer was glaringly simple: power. It was quite something else to tell a child molester that he hurt the little angels he so loved more than anything and make him believe it. The process of making ...

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 hang in my bedroom closet.

At age 30 I've been cross-dressing since my college days, though not on a regular basis. My friend Karen had talked me into doing so. I'm Bi so convincing me to don a d...

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 ten, someone would take the bait.

From what I gather, I don't think men expect to see someone like me at the gym, and when they do, they form a kind of fixation that is difficult to placate. The...

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 to open the door to face Harry. Harry’s jaw dropped when he saw me. In person, he instantly realized that it was me wearing a dress. He said, “What on earth are you doing? Are you on drugs?” I s...

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 each round, I felt myself getting more and more drunk. I had forgotten to eat dinner and wasn't the best beer pong player, so I figured I would have plenty of time off between losses. Ashley was a pro...

[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 fingers and squeezed it. She then put her hand into the air and spanked me a few times. She then moved the dress higher and pulled down my panties. She reached around and grabbed my cock with her hand....

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 on the board for. She thought she would slip in quietly so as not to disturb her husband of seven years. She knew he would be on his computer doing his job as a software engineer.

She quietly sli...

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 that she had seen him many times at football games, but never had the courage to go up and talk to him. Jason responded by saying that he had seen her many times too, but he also was too scared to tal...

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 going to experience the best parts of being a woman. Janice handcuffed me and then blindfolded me. She bent me over against the bed and slapped my ass. Janice pulled down my panties and stuck her fing...

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.” Nadia took the pair of handcuffs and handcuffed me. She then took a zip tie and zip tied my legs together. I was at her mercy now. I was laying face down at this point. Nadia took a step back and ad...

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 have been married 10 years. I went through 8 years of secretive panty wearing and dressing up and all that changed when she came home a day early. I am 5’ 6” and when fully painted and dressed can p...

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.

The cool night air bit into him. He didn't even have a jacket. His damnable landlord hadn't even seen fit to let him get anything before locking him out. Sure, his rent was two months late, but there us...

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. Chairs were shoved into corners in favor of the exam table, but even it was off center to provide the doctor room to move around. The room operated on the axis of a moving individual with tools and ...

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 homework to deal with."

"Oh okay..." I watch as she turns around but pauses "wait, for which class?"

"English..." I say.

"Is that English with Professor Hadley?"

"Yeah, you've got him...

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 some wine; actually it looked to be a lot of wine. She didn't look happy and I knew why.

"Hey baby, I'm sorry I'm late," I said, "work just got the better of me. I first looked at the clock and...

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 against my opening and as you do so your precum makes my entrance wet and ready.

Then, as you slowly kiss my neck, you slowly press forward and your head enters me and I softly moan and my eyes c...

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 behind my back. She handcuffed me and then tied each of my legs to the bottom corners of the bed. She put a pillow under me so that my back was arched. She said, “Ready to feel like a woman?” She slap...

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 I was in someone else's house. I was in someone else's bed. I looked to right and I could see quite a lot of brown hair draped over the bunched up covers. It seemed that I had taken home a lady frien...

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 Uncle George in northern Scotland, my sister was at college and I had full access to the clothes she had left at home.

I looked at myself in the mirror, standing there wearing her school uniform. ...

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 expected of me has been described, in general terms at least, and I am mentally prepared.

I know the rationale behind the assessment I am about to be put through, and I will willingly endure it to ...

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 moved her hands down to my waist and under my skirt. She grabbed my underwear with her hands. She leaned in and whispered in my ear, “I always though you were so hot. I was confused why you never made ...

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 time and it felt good what Shawn was doing. From the corner of my eye I could see Ash and her boyfriend making their way to the door. Both of them left and left Shawn and me alone. I finally had some 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 protecting his modesty were his underwear.

Tony had been shopping at the mall earlier, not really looking for anything, just browsing a few stores, killing time. He had been browsing in the lingerie...

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 slut right now?” I nodded my head. She said, “Well it is about to get a lot better. Alexis went over to her bags and pulled out a smaller black bag. Alexis told me to lay my stomach down on the bed....

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 $700. At first the girls who came over would do light cleaning before we moved on to the bedroom. Some were better than others both at cleaning and at sex, but after talking with neighbors I felt a full ...

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 reached for them and took them in my hand. I brought them to my lips and felt their breath. The smell of mom's cunt is driving me crazy.

I continued to shower my mother's panties, and at one point...

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 me, just as he served everyone else without a word. Ben and Beth got coffee. Ben's black and Beth's with sugar and cream. Alan and I juice, freshly squeezed, I was certain.

"Well, birthday boy,...

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 ride and I had two more to go. I still had to figure out how to tell Carol about everything that had been going on and still didn't know what to do about Steve. He was still texting me a few times a wee...

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?"

"Exhilarating is what it is. The boys can't keep their eyes off me, and I love it. I've even caught some of the faculty checking me out, and Dean Wagner," I paused, "holy shit, Carol." I could feel...