Crossdressing Stories

8

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

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stockingluvr

It Wasn't Love But It Sure Felt Good!

Some nights just don't turn out like you thought they would.

Al called me first thing Saturday morning to express how much he enjoyed our time together last night. He also asked if we could do it again soon. I told him that we could this coming Friday if he was available. I could show him some of my other outfits and the pictures that he took of me as well. He gleefully responded that it was a date. As the week progressed ever so slowly, we spoke...Read On

Added: 10 Jan 2017 | Category: Crossdressing | Words: 1,082 | Tags: anal gay male just fucking | 5 Comments

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

15

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ThePhantom

Taking That First Step. Part 2

Lance returns to the specialty shop

Lance's family was surprised to hear him up and moving at 6:00 AM. Saturday was his day to sleep in now that school was out for the summer and he didn't work on the weekends. They didn't question it and soon fell back to sleep as Lance headed to the master bathroom. He showered and then toweled off before heading back to his room. Once in his room with the door locked behind...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

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

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

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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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:

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

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

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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

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

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

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

13

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trinitytowers

A Nanny Femtastic! - Chapter 11

A NANNY FEMTASTIC! Chapter 11 We walked to the harbour and found the boat. There were too bulky security guards checking people as they entered. The boat was in fact a massive cruiser! We joined the queue, it was obviously not a little gathering. The other women were dressed in classy whites and float summer dresses, we looked like too cheap hookers! “Trinity this was a...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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allfours

Carl, Carla and Hannah - Part 11

Carla becomes more feminine, and then Carl has to make a decision...

"So," Hannah said as we reached the outskirts of the city, "How did you enjoy your first time dogging?" "Is that what it was?" I asked incredulously. "Well, sort of, yes. What did you think it was?" she laughed. "And the bloke who was watching thought you were a girl as well!" "I know," I said, proudly. "Hey, does that mean that the bet's already won, a week early?" I asked...Read On

Added: 07 Feb 2014 | Category: Crossdressing | Avg Score: 4.75 | Words: 3,361 | Tags: crossdressing feminization toys strap-on cum-swapping

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

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

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

7

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allfours

Carl, Carla and Hannah - Part 25

The Honeymoon Party - the final chapter.

A knock at the door broke our reverie. Hannah turned to me quite pointedly and said that I should answer it. I looked at her questioningly, but she just gave me her mischievious grin. "Call it my wedding present to you, Carla," she said, enigmatically. "Now, go see who's there." Bewildered, I walked to the door of the suite, loving the sound of my wedding train rustling behind me. As far as...Read On

2

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ThePhantom

A friend with something extra - The Conclusion

Lorna gets Grant ready for his lover.

It was on the following day that Lorna woke her step-brother up very early. "Come on and get up and get breakfast," she told him shaking him by the shoulder. "Huh? What?" he mumbled, still half asleep. "Come on. I need you to become sexy again," she insisted. He then stripped down to a pair of silk, hip hugger panties and donned a silk dressing robe that he found hanging on his doorknob....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

9

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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

2

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dawnforever

Growth and Admissions

In a place where everyone cares, is the perfect place for a new beginning.

My initial impression that this town resembled Mayberry turned out to be reality, and that the people here where genuinely nice. Everywhere I went people introduced themselves and seemed to want to be my friend. At first, I really wasn’t sure what to think, but after the initial shock wore off, I began to relax and accept that this might have been the best decision of my life. After a few...Read On

12

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JessieCD

Jessie's Fantasy Chapter 7: The Tables Got Turned

Now that Jessie decided to turn the tables, how will she handle all of her friends?

Here I was, getting my boy pussy plowed by my good friend Scott, when Mark decides that he needs to call Jesse, the male me. As he was starting to dial my phone number I realized that I never turned the ringer to vibrate after we left the night club. I was panic stricken as they all knew the distinct ringtone that I used. I couldn’t let my phone blow my cover. I had to think fast, but what to...Read On

8

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vanessagrrl

Just the Two of Us, or Four

Vanessa and Greg fail at trying to spend a night alone

As time went on, the line was beginning to blur between me being Greg's girlfriend and Amber's pet. Greg decided that we needed a night alone. That didn't work out exactly as planned. He booked us into a lovely, fancy hotel in the heart of the city. Next up was going to be a nice dinner at a gourmet restaurant, and then we'd see where the night went from there. I wanted to impress, so I took...Read On

9

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allfours

Carl, Carla and Hannah - Part 17

Luke takes Carla to the cinema

As the week progressed, I looked forward to my date with Luke. I even found myself thinking about him when I was at work, and more than once found that I started to speak in my female voice before I'd realised it in the office. As Claire was 'unavailable' for a few days, Hannah went out of her way to make her life difficult at work. One lunch-time she went into her office, locked her door...Read On

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stockingluvr

An Introduction to Crossdressing, Pt. 6

As our evening progresses the fun continues.

After Steven leaves me at the table with Jackie and his new friend Chandra, I start to fill them in on the details. I tell them, “It’s really Jackie’s fault that I got fucked so good; since he was being so aggressive with his dance partner, I got jealous and grabbed Steven’s ass.” Then I continued with, “This led to Steven grabbing mine beneath my skirt, and then stroking my cock and balls...Read On

Added: 03 Jun 2015 | Category: Crossdressing | Words: 1,510 | Tags: anal exhibitionism masturbation | 3 Comments

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Crossdressing

Carl, Carla and Hannah - Part 10

It Wasn't Love But It Sure Felt Good!

A Night of Firsts pt 3

Taking That First Step. Part 2

Call Me Julie part 3

Evie Gets Her Reward

That First Halloween. Part 2

Confessions of a Sex Crazy Cross Dresser Part 6

A Nanny Femtastic - 10

Crossroads Ch.4

Taking That First Step. Part 3

An Introduction to Crossdressing, Pt. 5

CD Mistress Cheyenne can't fight the craving for Candy

Jessie's Path

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

A Nanny Femtastic! - Chapter 11

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

Carl, Carla and Hannah - Part 11

A New Beginning (Part 3)

Becoming Chloe - Part 11

One On the Way. Part 1

Carl, Carla and Hannah - Part 25

A friend with something extra - The Conclusion

The Best of Both Worlds 2

Ladies Night at the Leather Bar Part 1

Growth and Admissions

Jessie's Fantasy Chapter 7: The Tables Got Turned

Just the Two of Us, or Four

Carl, Carla and Hannah - Part 17

An Introduction to Crossdressing, Pt. 6