Crossdressing Stories

8

jessicaCD08

Memories of Anne

Jessica's new secretary learns the consequences of mistakes

The time on the mantle clock showed 9.20pm. I sat on the sofa and slipped my heels off and tucked my stocking clad legs under me. I picked up my glass of Chardonnay and took a sip. My thoughts went to the events of today. It had actually all started a month prior. I was recruiting for a new secretary when Anne’s curriculum vitae had come across my desk and it struck a cord with me. So I...Read On

10

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borrowothers

A Night of Firsts pt 3

Pam has a first

We all took a sip of our drink. Catherine, Anna and myself, presided over by Lauren. I felt like a new gurl at this party. I bit my lower lip, I wriggled in my seat for my dress giving an accidental glimpse of way too much upper pantyhosed thigh. I blushed so deeply. Lauren must have sensed it as she leaned in closer and told me that I was a flirty gurl and those legs of mine might get me...Read On

10

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ThePhantom

Taking That First Step. Part 3

Lance's transformation continues

Lance had arrived at the specialty shop as himself, a young man wearing women's lingerie under his jeans. He was met by the stunning Cassandra, the shop owner and his confidant. She treated him to a wig, lipstick, eye shadow and then directed to one of the changing rooms. Waiting inside was one of the sexiest lingerie combinations that he had ever seen. Upon exiting Cassandra reappeared...Read On

30

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Milik_the_Red

Night Trawling: The Crossdresser

Sometimes the streets offer the most delicious surprises.

The streets of Pomona live two lives. Like maternal twins, they coexist in parallel, appearing as virtually identical to those merely passing through its old and storied neighborhoods. During the day, with the sun high overhead, myriads of people — whether they’re commuters traveling like drones or soccer moms distracted by their busy lives — they choke the streets in a constant pulse of...Read On

11

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trinitytowers

A Nanny Femtastic - 6

A Nanny Femtastic Chapter 6 ......... felt incredibly empowered, with women and Men coming onto me! I was loving being between the two sexes but presenting as a glamorous female. Alex was very dominant and bought me drinks and acted in the male role very much that night. Lou and her slept together generally, but there was no issue with Alex coming onto me. Later in the evening...Read On

7

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CourtneyFux

Girlyboy Gone Wild - Part Three

Playing dress up for men at my panty party is lots of fun.

With my little sexy blue plaid school girl skirt pulled up, I leaned over the desk for teacher Dan to spank me. Dan reached down and pulled down the back of my little white cotton panties revealing my very sexy ass. I saw how big his eyes got when he saw two of the sweetest cheeks he ever saw. He looked up at me. "You have a nice butt on you, Courtney." I smiled. "I hope I get to sit on...Read On

9

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hoterotica

Fucked in the Fitting Room Part Two: The Explosive Conclusion

When my lover finds a dress on the sales rack, I get more than I bargain for.

I took Allen's hard cock in my mouth and began to suck it slowly. "Oh, God," said Allen. I rolled my tongue around the tip of his cock and then ran it up and down the sides. "Suck it faster, babe," said Allen. I happily complied, bobbing my head up and down on his cock as fast as I could. I grabbed his balls in my hand and stroked them gently with my fingers. "Oh, baby, that feels...Read On

9

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cassandrababy

Confessions of a Sex Crazy Cross Dresser Part 10

Chapters 19 and 20 of Book #1

Only 1 chapter left after this installment....I hope you are still enjoying Sandy's adventures Chapter 19: Last Day in Vegas The next morning Tanya left for her house after exchanging numbers with us and promising to visit Peggy in Phoenix next month. The hotel had arranged a car to take Peggy to the airport for her 9:00 flight. I was sad to see them go, but at the same time, I knew I...Read On

29

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DeedraCd

The Change Up - Part 4 - Tower Chair

Deedra shows how big a slut she is and becomes a member of Elsie’s VIP club!

Looking through the sheer curtains of the cabana, I see about a dozen people looking at both of us. Some I just met tonight and others that I don't recognize. Then Emily says to me, "Since you been a naughty cum slut again, I will have you service some of the VIP members tonight! Remember don't talk to anyone and only whisper into my ear." Cuddling next to Emily, I think back to the...Read On

6

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ThePhantom

That First Halloween. Part 2

Princess Jasmine and Zorro spend the night together.

They parted company long enough for Guy to reach his own car and pull up behind the SUV that was already on the street. As he followed it to the Carriage Hills condos, he was unsure how the evening would end. Carriage Hills was a gated community and the SUV stopped long enough for Zorro to address the guard on duty in the shack.They proceeded to an underground parking garage and parked...Read On

5

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JessieCD

Jessie's Path

A true story of the Path that Jessie took.

One’s path in life has three primary sections. The first one is what made a person who they are. Everything from their parent’s genetics, to how they were raised, the environment they grew up in, and any uncontrollable outside influences causing a life changing event. The second section of the path is what we see, feel, hear, taste, and touch at this very moment in time. It is a collection...Read On

7

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starbelliedboy

Webmeets Diary Ch. 04

Celebrating the end of university as a slutty schoolgirl.

Note to the reader: In this diary I will tell the true stories of my sexual encounters that have come about thanks to the internet. Some more precise details such as names and places will be left out to protect mine and others privacy, and also because they don't matter, but otherwise I will try to be as accurate and truthful as possible. As I neared the end of my university course I had...Read On

10

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Heytherebaby

Becoming John Collins' Mistress - Part One

I get to know Mr. Collins and get invited to meet his friends

Hi. My name is Chris, though some know me as Christine. I am John Collins’ mistress. We care deeply for each other. John “keeps” me. He supports me financially and in return it is my pleasure to keep his sex life exciting, as well as entertaining any of his gentleman friends who drop over. It all began innocently enough, I suppose. I had just turned eighteen and had moved out from my...Read On

4

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LucyLou62

A Weekend away

A weekend in a hotel turned out to be more that was expected.

Stevie had always wanted to have a weekend away with a load of like minded people, i.e. trannies and admirers. He decided to find a place where he could do this and be the real Stevie, or his girly name, Lucy Lou. He searched the net and found a place about two hours drive away. He booked it and counted down the days to be there. He had bought some new stuff and had practised his makeup....Read On

8

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allfours

Carl, Carla and Hannah - Part 10

Hannah tells Carla about her night with Claire, and then takes her to a dogging spot...

Hannah took a different route than usual into town, and she surprised me by parking in an area we don't often go to. Once we'd left the car, we nipped into the Bullring and picked up the few things I needed. I was so nervous that I could hardly speak, but Hannah insisted that I did so. I imagined that everyone was staring at me, but after a while, I came to realise that most people didn't...Read On

6

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Maid2frill

Evie Gets Her Reward

The final part in the story of Mistress Sarah and Evie

I went downstairs to the kitchen, carrying the cold tea. As I walked into the kitchen, I could see up the drive through the window. There was a car parked at the top of the drive, a taxi. I ran back upstairs to Mistress Sarah. “Mistress, are you going out again?” I asked. “No dear,” she replied. “why do you ask?” “There is a taxi parked at the end of your drive. It looks like the same...Read On

4

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Tier_innerhalb

The Best of Both Worlds 2

"Oh, God, Daniel!" Arya cried out in ecstasy, as her body came to orgasm. Sitting on top of Daniel, she let her body bounce on him, as he shot a load of cum into her with every upward thrust. She screamed excitedly with each push that Daniel gave until he was finally finished, and Arya rolled off and lay beside him. The sex had been both exhilarating and disappointing. As always, it...Read On

5

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havingsomefun

A New Beginning (Part 3)

My first experience in public

It’s been a while since I’ve written. For background, I’ve got a wonderful relationship with my wife Joan and an ongoing affair with my step-daughter Ellen. It’s possible since Joan’s job keeps her out of town for extended periods of time. Both of the women in my life have the same sexual tastes and to say things get kinky is an understatement. Ellen was very much in dressing me up from...Read On

5

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CallmeJulie

Call Me Julie part 3

The night gets more interesting

I stretched and reached out like a cat waking from a nap. Scott was resting on his side with his elbow down and his head resting on his hand looking down at me. "Enjoy your nap?" he asked as he stroked my shoulder. "How long was I out, how long have you been watching me?" I replied. "Not too long on either of your questions," he replied. I glanced at the clock and it read 8:00,...Read On

13

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allfours

Becoming Chloe - Part 11

Vickie meets Tina, and and Chloe has a surprise for dinner...

Vickie was naked, apart from her white jacket, stockings and suspender belt. Unlike the woman who left several hours ago, her hair was now loose and dishevelled, falling softly to her shoulders. Her make up was no longer pristine: her mascara had run a little and her lipstick was definitely in need of refreshing. Her lips seemed a little swollen, and her jacket was parted just enough for me...Read On

13

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Pudmeister

Crossroads Ch.4

Another chapter in this fantasy tale of a young man's journey into becoming who he is.

I am on an airplane flying to Vancouver. I have an appointment with a doctor to have sexual reassignment surgery. I am so excited I can't stand it. I know this is what I want. My recent encounter with a woman convinced me. I have no doubt about it now and won't look back. We land and as we deplane I notice, as always, the admiring looks I am getting from men, including the pilots. I...Read On

4

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ThePhantom

One On the Way. Part 1

A new plan was required if he wanted to see Vicki.

Darren had met Vicki through Charlene, one of the girls from his school. He had just attended a Saturday movie matinée and was waiting for the bus to take him home when they walked up. Apparently, they were there too. From the moment they were introduced and locked eyes on each other, there was an instant attraction. He mentioned that he was surprised that he had never seen her in the...Read On

11

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cassandrababy

Confessions of a Sex Crazy Cross Dresser Part 6

Chapters 11 and 12 of Book #1

Here are the next two chapters of Sandy's adventures Chapter 11: Photo Shoot and the Elevator Ride I slept great on Monday night after my craziest night of cross dressing. My body felt great as I slept in late. However, I had to admit, I felt like my ass had been torn up from Stan’s incredible cock. I realized now that almost all men wanted to get their rocks off with strangers. Stan...Read On

6

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ThePhantom

The Magician's Assistant Or How It began. The Conclusion.

The Halloween show they performed seemed to open the floodgates of bookings.The demand for his shows grew and soon they were working almost every weekend instead of every other one. Carl was forced to find a new headquarters for his magic workshop as his equipment began to overcrowd his garage. With Ken's business contacts he located a vacant factory that was only a few years old for a...Read On

8

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latecomer91364

Ladies Night at the Leather Bar Part 1

Lingerie Love in the Land of Leather

Chloe McGill never led me astray. I was a fulltime, tax paying citizen of Astrayville long before I met her - I just wasn't that good at it. Then Chloe came along, and that girl has ended up getting me into some of the most outrageous adventures. I adore her. It must be made clear how much more she is than just a cohort in gangbangs and sexual trysts of all sorts and sizes. She is the...Read On

8

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nymanirene

Three nights in London / Night 1: Irene's transformation

Cute Tgirl goes on the adventure of her lifetime

I met Gabrielle at a music festival where I played with my band. After our gig, she complimented me on our show and we started to chat. She was over from the UK and was staying with friends in Amsterdam. I was impressed by this pretty redhead, dressed in a bit of a Lolita style with ultra black makeup, a cute red tartan skirt and huge boots over fishnet boots. We directly clicked and she...Read On

8

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MistressCheyenne

CD Mistress Cheyenne can't fight the craving for Candy

CD Mistress Cheyenne's kinky side comes out in the second meeting with new slave Candy.

Almost two long weeks had passed since my first meeting with my new slave Candy. Our first encounter was special and my sexy new sub had not left my mind since he walked out of my door. His juicy ass and hard thick cock have filled my thoughts each day since. I had found myself wildly attracted to Candy and lusting for him constantly. After deciding that ten days was long enough to make him...Read On

6

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trinitytowers

A Nanny Femtastic - 10

A NANNY FEMTASTIC! Chapter 10 I rose early the next day and put on my white lace bikini, and took a dip in the pool. I was sitting on a lounger drying myself when Felicity came out. “Good morning gorgeous!” she said kissing me on the cheek. Our breasts rubbed together. “You know we have that party with those guys today sweetie?” “Are you sure we should go Felicity?” I said...Read On

Added: 16 Feb 2010 | Category: Crossdressing | Avg Score: 4.83 | Words: 1,397 | Tags:

11

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BadDog9

Exploring Even Further

Shauna meets Jerry's wife and things get heated.

For the rest of the week I was a total wreck, dreading, craving, anticipating, and fearing, the arrival of Jerry’s wife and Rocketman69, whose real name I'd discovered was Jim. Just thinking about all of the possibilities had me literally trembling with lust and, at times, fear. Jerry, too, was in a constant state of arousal. Neither of us could believe what a slut I was becoming. After work...Read On

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stockingluvr

An Introduction to Crossdressing, Pt. 5

My first time at a not-so-straight club is friendlier than I imagined.

As Jackie and I pulled up to the club my mind was racing. My main concern is whether we look passable, and that if we don’t, that we might be laughed at and teased. As I expressed my concerns to Jackie, he said, "Remember that we are at a place for people like us who are a little different." As his statement sinks into my thick skull, all my anxiety starts to slip away. For the first time in...Read On

Added: 29 May 2015 | Category: Crossdressing | Words: 2,670 | Tags: anal bisexual exhibitionism oral sex | 6 Comments

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Crossdressing

Memories of Anne

A Night of Firsts pt 3

Taking That First Step. Part 3

Night Trawling: The Crossdresser

A Nanny Femtastic - 6

Girlyboy Gone Wild - Part Three

Fucked in the Fitting Room Part Two: The Explosive Conclusion

Confessions of a Sex Crazy Cross Dresser Part 10

The Change Up - Part 4 - Tower Chair

That First Halloween. Part 2

Jessie's Path

Webmeets Diary Ch. 04

Becoming John Collins' Mistress - Part One

A Weekend away

Carl, Carla and Hannah - Part 10

Evie Gets Her Reward

The Best of Both Worlds 2

A New Beginning (Part 3)

Call Me Julie part 3

Becoming Chloe - Part 11

Crossroads Ch.4

One On the Way. Part 1

Confessions of a Sex Crazy Cross Dresser Part 6

The Magician's Assistant Or How It began. The Conclusion.

Ladies Night at the Leather Bar Part 1

Three nights in London / Night 1: Irene's transformation

CD Mistress Cheyenne can't fight the craving for Candy

A Nanny Femtastic - 10

Exploring Even Further

An Introduction to Crossdressing, Pt. 5