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Cross Dressing Stories

Our crossdressing (cross-dressing) stories feature tales of either gender (usually male) dressing up in the clothes of the opposite sex, for reasons of sexual gratification.

Crossdressers are akin to the transvestic fetishism, which is a sexual fetish for the clothing of the opposite gender.

The crossdresser can be of any sexual orientation.

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My Sister’s Bully Ex 2

Submitting to my sister’s bully ex as things escalate to new desires.

It was four days since I deepthroated Rich to a huge orgasm in the living room of my sister’s house. I wasn’t sure if he would keep to his word and keep my true identity intact but I thought that if he was intending to expose me it would have happened by now. I also had the photo of me holding Rich’s cock in my hand as insurance should he ever threaten to expose me in the future. I told myself I’ll never be in that positi...

My Air BNB Experience Part 3

The last morning of pleasure

It was hard to believe what happened. I awoke to the sounds of birds and the sun rising over the mountains. I was still in such a good mood from last night. I got up, put on my bikini, and went for another quick dip before returning for a Coffee out on the deck. Around 8 am, I heard their car crossing the paddock and pulling up beside me. Debbi hopped out and walked up, greeting me again with the bag. “Well, I see our lit...

Karen’s first night out

In the soft glow of neon lights, a cozy bar tucked away in a quiet part of town was buzzing with low conversation and the clink of glasses. The warm ambiance and chill music made it a perfect place for anyone seeking a little escape. Sitting at the far end of the bar, Karen adjusted her black lace gloves, smoothing the fabric over her wrist. She’d been coming here for a few nights in a row, always drawn to how accepting i...

An Affair With A Twist

Part One - My Latest Affair Takes An Unexpected Turn

I connected with Jim online. Although married, I enjoyed having occasional one-night flings. I’d usually connect with a married guy who came to town on business. I wasn’t interested in anyone local. It was important to get to know the guy before I met him though. The process took a while but always resulted in meeting a nice guy. Over the last couple of years, I’d fucked fifteen very nice and appreciative married men. All...

SissyMandy - Legally Mandy Parker

The day I change my name ends with a sex party I didn't quite expect.

An aura of confidence surrounds me this morning as I head to the master bathroom to shower with the girls. I'm super excited about my court date this afternoon to change my legal name and gender, plus when I woke up, I was still wound up about finding out last night my sissy sister Marci is coming to our party next weekend! I was just standing naked in front of my full-length mirror, admiring myself like I do most morning...

My Sister’s Bully Ex 1

My sister’s bully ex-boyfriend notices me dressed and I can't resist

My name is Sophia and I’m a twenty-one-year-old sissy girl who loves to dress femme all the time. Over the past few years, I have got more and more daring with my feminine side, going out in public dressed. It was on one of those adventures I discovered a nightclub in town that was a hotspot for the LGBTQ community. I would often go there fully dressed and make new friends, drink, dance and have some fun. It was on one of...

Ryan's New Job

Ryan learns to love his new job...

Ryan was just starting out on his own, in his early twenties, with his own apartment and living alone. He had a few jobs, enough to pay rent and bills but was barely making it by. He saw an ad for a male or female secretary for a women’s magazine, so he thought he’d give it a try. He went for the interview and saw mostly girls about his age there also applying for the job but there were a few other guys. He was finally ca...

Changing Room Encounters (Part 2)

Cascading Consequences

I followed the security guard, trying not to look around, embarrassed that someone might see me. I couldn’t help but notice how well-built he was: broad shoulders tapering to a small waist, and what I imagined were chiseled abs. He had a military-like crew cut and a ruggedly handsome face. He was probably 6' tall. I wondered if I was fully dressed and made up; could I seduce him? So far, I was avoiding eye contact out of...

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SissyMandy - Relationship Realities

Our first week in our new house, and things are already starting to get complicated.

"Ooo… yeah, baby…" Sherry breathlessly moans, raking her nails raking across my back. "Don't stop, Mandy, don't stop!" Oh, God. I don't know how much longer I can hold back the flood of cum that's been building in my balls since we got home from shopping for clothes at the mall. I mean, I'm borderline anorexic after my three-month starvation diet, and I'm literally in love with my new body, so finally getting new clothes...

Changing Room Encounter

Crossdressing coincidence

I’ve been getting bolder in “under wearing” especially in the early fall when the weather is cooler. I love to go shopping at Nordstrom Rack, everyone is so focused on looking at the clothes I feel like I can show a little and not get caught – but that’s the thrill of it right. The only downside is not being able to shop in the women’s section without standing out. One day, it was early so not many people were there yet,...

Too Far Dommed

Online closet sissy goes too deep.

Luke's fingers danced over his laptop keyboard, the dim glow of the screen casting eerie shadows across his room. He was deep in the throes of sissy porn, his cock hard against the constraining fabric of his briefs, captivated by the sultry submissives surrendering to dominating alpha males. His breath hitched with every moan and slurp resonating from the speakers, the scenes feeding his growing desire to explore this for...

Trying To Meet A Guy

Public sexual encounter

July 8, 2024 I am a thirty-seven-year-old crossdresser living overseas in southern Japan and I have recently started going out dressed up. It started funnily one day when I just decided I would put on a skirt while in a park and crossed the road to go into a shopping complex. I wasn't even disguised, and two young women noticed me walking towards them, and shared a laugh as we passed. What a cool feeling, exposing my legs...

Stolen Treasure Part 2

Ian gets assistance.

The remaining school days seemed to fly by for Ian, and before he knew it, summer vacation was full upon him. He managed to secure a part-time job as a dishwasher to provide himself with spending cash and enjoyed his days playing baseball with his friends, riding his dirt bike, and doing all the things that young men do, but it was the nights that were his favorite part of the day. After an evening of television watching,...

The Lake House - Part Two

It Gets Complicated

I awoke Sunday morning in my pink nightie. I thought about how much had happened in the previous two days. I was now Jim’s girlfriend. I had sucked off four men and swallowed a quart of semen. I became aroused. I only had to play with my clit for a minute before I started cumming. I caught most of it and fed it to myself. I looked forward to sucking Jim’s huge dick. “You better get dressed, girl,” I said out loud. I did m...

SissyMandy - Married Wives

A sissy with two hot wives? What are the odds?

I'm awakened early the next morning by Mistress tapping on my bedroom door. At first, I think she wants to play around in bed like Sherry did yesterday morning, but instead, she tells me to do my bathroom business, then come to the master bathroom… naked. Every bedroom in our new house has its own bathroom, and mine has this giant oval-shaped tub with those cool whirlpool jets on the sides. All I thought about when I firs...