Crossdressing Stories

10

ThePhantom

The Magician's Assistant or How it began - Part 1

Ken had led a pretty normal life until the year his longtime friend needed an assistant for his growing magic act. Magic had always been a hobby with his buddy Carl and he spent many a day watching him perform a new trick in his garage seeing if he could detect the secret. Their being forced to take woodworking classes in high school really paid off when Carl expanded into the realm of...Read On

7

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allfours

Becoming Chloe - Part 23

Chloe makes a decision, and Colin comes over for the weekend...

Colin kept his promise, calling me at least three times a day and texting me every couple of hours. The shop wasn't too busy on Monday, so I managed to get quite a lot sorted out. Now that I was going to be the owner as well as the Manageress, I decided that I wanted to change a few things. I also looked at some alternative suppliers who seemed a little cheaper, so I spent the day sending off...Read On

5

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Dividence

The Wedding Proposal, chapter VI

Reality catches up to me.

The dinner was wonderful. Tina was the sweetest sister-in-law I could ever wish for. We found that we had lots of things in common, and quickly bonded. She told me all sorts of stories about Tony, and I shared stories from my time as his friend. I had to concentrate to adapt the stories to the new ‘reality’, but as long as Tony played along it went great. He seemed a bit uncomfortable with...Read On

14

vote

COMP

Kasey

Late Night Bus

Ben makes and receives a deposit at the depot...

It's a beautiful, foggy English night. Panting, my lungs aching from the cold, I reach the bus stop at a dead run skidding to a halt on the loose crumbling tarmac. The salty taste of Steve's cum still fresh on my tongue and my anger unabashed. Catching a breath, I realise just how much I love nights like these. The ubiquitous street lights struggle to penetrate the gloom of their...Read On

11

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allfours

Becoming Chloe - Part 22

Chloe and Colin have a date...

We must have all slept soundly because the only thing I can remember is waking to the sound of Vickie getting up to go to the bathroom, her cock still jutting out in front of her. Later still, I awoke feeling the need to pee, so I got up as carefully as I could and headed for the bathroom. When I returned, I felt a little cool so I slid under the duvet before flaking out again. The next...Read On

28

vote

COMP

adele

Dan a.k.a. Becca

Dan discovers his feminine side

Dan had been fascinated with women’s panties since he had found a pair belonging to his sister accidentally mixed in with his clothing. He had rubbed them against his face feeling the silky smoothness. He kept them for a few days until he heard his sister asking about them, then made a pretense of finding them stuck in between the washer and dryer. After that, whenever he had the chance, he...Read On

11

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allfours

Becoming Chloe - Part 21

A bargain is struck, and the girls celebrate...

"Now. One of the reasons I've asked you here, Chloe, is to pass some things by you. First, I want to thank you for your understanding about how much time Vickie has spent with me these last few weeks. She's been a treasure, and I don't think I could have got through the hospital appointments and the antenatal clinics and the morning sickness without her. I guess what I'm trying to say is that...Read On

6

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Dividence

The Wedding Proposal, chapter V

With my life back to normal, I cannot seem to relax, until a fateful call makes my life whole again.

I turned the key in my apartment door. As I heard the lock click, and the door swinging open, I suddenly felt a strong sense of abandonment. The sensation was so strong that I had to close my eyes and draw a deep, long breath. I was surprised, but instantly knew what it signified. Stepping through that door would be the final return to myself. To who I really was. The magic would be broken...Read On

10

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allfours

Becoming Chloe - Part 20

Chloe receives two invites for the weekend...

Unsurprisingly, I was very tired the next day, so I tried to keep busy to help me stay awake. Of course, the thought of a phone call from Colin certainly perked me up, and it must have showed. Around midday, Tina came in just to check on things. Nowadays I saw less and less of her at the shop because I virtually ran it on my own, plus she'd had a bad time with her morning sickness, so her...Read On

7

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SashaCD_ThongPanties

My Foggy Late Night Story

On a foggy late night, Sasha gets fit, lucky, and... loved?

It was a cold, wet December night. Here I was in my room, feeling exhausted, and laying on my bed doing the whole Netflix and chill thing. I had just pulled a long afternoon and evening event with my college study group. We spent the day as total masochists painfully cramming whatever we could into our tired brains for our finals. It had worn me out so much that I didn’t want to do...Read On

12

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sissycderica

Erica Meets Sarah: Part 1

Slutty CD Erica meets Sarah to fulfill her ultimate fantasy for the first time.

I woke up alone on Saturday morning in my nylon blue g-string and nothing more. I wanted to feel it the instant I woke up, my sexually charged femininity, I wanted to feel it all day. Today I'm not a man, today I'm the girl every man wants. Today I'm a slut, your slut. I showered and shaved myself smooth. Ridding myself of body hair was always the first step. Nothing could make me feel...Read On

12

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allfours

Becoming Chloe - Part 19

Tina and Vickie have some news, and Chloe has an interesting evening...

You know, they say that the thing about working in a sweet shop is that you soon seem to lose your appetite for sweets. Well, working in a sex store is pretty similar experience. At first, I was amazed at the variety and array of different toys, magazines, DVD's, clothes and nick-nacks that were available. After a while, however, I began to be less and less amazed (and aroused!) by the things...Read On

9

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allfours

Becoming Chloe - Part 18

Chloe goes home and gets a seeing to...

I have no idea how I managed to drive home with my skirt soaking with cum and my cunt full of the plug that Tina had slid into me. The scent of sex filled the car, and the fear of having an accident or having to stop kept me on my toes enough to drive more carefully than I ever had. The spunk on my skirt started to dry as it stuck to my legs, making me a little uncomfortable as I weaved...Read On

18

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Dinata

Park-n-Play

State parks are not just for nature lovers...

Being the social butterfly that I can be at times, I was checking a website that listed my area to see of there were any 'cruising' areas I could check out in hopes to share my fetish for crossdressing and pleasure. There were several areas, too many to choose from, so I opted for a forested state park. Since much of the funding for the parks in Ohio have been suspended or cut, the chances...Read On

13

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allfours

Becoming Chloe - Part 17

Chloe starts work, and receives an unexpected bonus...

Two weeks after the agreement between Vickie, Tina and me, I was a different woman. I'd told my parents about my planned transition. As I thought, it wasn't easy, but I felt so much better once it was out of the way. Mum took it fairly well, but I'll never forget the hurt look on my father's face as I explained how I felt, and how I wanted to be a female. Despite that, he still gave me a hug...Read On

7

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DarkSide

She Made Me Do It

My package arrived in the post – I just couldn’t wait to open it.

Something inside me just grabbed hold of my male shackles and snapped them in two; discarding them into the depths of depravity. I had been writing stories about crossdressing and transsexuals all week. I had been looking at girly pictures, not the feminine girl ones, the ones that had dicks. Some of them were absolutely gorgeous, far better looking than some women and I wanted to be one of...Read On

11

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Dividence

The Cabin, chapter III

As the storm clears, we decide to make the most of our time together.

When I awoke the next morning sun was shining in through the windows, bathing my golden hair in its rays. I got up quickly, but careful not to wake my lovers. The nice weather made me think that we would soon have to leave the cabin and my taste of life as a girl would be over. Regretting this, I was determined to make the best of my morning with them. I went to the bathroom and once...Read On

2

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jerrixdresser

My 2 AM Phone Call

Sissy cross-dresser is told to report to a motel at 2 AM

It was about 2 AM when the phone rang. The voice on the other end simply said to get dressed. He told me exactly what to wear. Exactly. He wanted me in a black micro mini skirt, little black mesh top that barely came below my nipples, five inch platform heels, lots of junk jewelry and a bushy Vegas platinum blonde wig. He said to come to the Diamond Motel on the Gulf Freeway and then he hung...Read On

10

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allfours

Becoming Chloe - Part 16

Chloe makes her feelings known to Tina

Tina stayed the night, but I couldn't sleep with three of us in the bed, so I got up around two in the morning and went to sleep in the spare room. I didn't mind leaving Vickie and Tina alone together. Besides, I knew I would have to get used to at least a couple of nights a week on my own anyway, and my mind was still in a whirl with everything that was going on. I tossed and turned as...Read On

12

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allfours

Becoming Chloe - Part 15

An agreement is reached...

Tina's car pulled into the drive around ten the next morning. Once the front door was closed behind her, she greeted Vickie with a passionate kiss, and then did the same to me. It felt good to be in her arms again, and I knew it would be hard not to give in to her, but we needed to sort things out. The fear of losing Vickie to her had not gone away, so I needed to make sure we kept our feet...Read On

20

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Dividence

The Cabin, Chapter II

I do my best to comfort the two frozen wanderers stumbling through the door.

I do not know how long I sat there gazing into the flames and sipping wine in complete peace. The wind outside was far away in my mind, but suddenly a huge bang broke the silence. The door flew open and slammed into the wall. Rain swept through the small cabin and sprayed me with icy cold droplets. I nearly fainted from shock, and the noise from my pounding heart overshadowed the howling of...Read On

15

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DarkSide

My First Time

Melissa was excited, it was her first time.

The sheer thrill of what I was about to do was bursting through my body. My nipples tingled at the thought and my heart was pounding in my chest. I pinched one of my nipples until it hurt, just to prove that I was not imagining it. I simply couldn’t wait to see Mark. Three hours to go before I would stand in front of him and let him touch me, caress me and fuck me if he wanted to. All I had...Read On

12

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allfours

Becoming Chloe - Part 14

The aftermath. Chloe and Vickie have a heart-to-heart.

"Shit!" I was immediately awoken by Tina's curse. I opened my eyes to see her gorgeous, naked ass fly through the door to the bathroom, so I turned to my naked wife next to me, still half asleep. "Good morning," I murmured. "What was that all about?" "She's late for work. She should be at the shop for nine and it's gone half eight." "Oh," I said as I moved to snuggle next to her. ...Read On

12

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allfours

Becoming Chloe - Part 13

Ménage a trois...

Vickie sat down on the sofa and, spreading her legs wide, directed me to her snatch. I willingly let myself be guided to her most intimate parts and breathed in her womanly aroma. I wanted to savour her, so I took my time. I kissed her inner thighs, so different from Vickie's, and brushed my nose against the thatch of hair between her legs. I flattened the mass of curls, revealing her...Read On

22

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tvk3983

Dana Finds A Lover

Dana meets a man and becomes his

I've been dressing since I was ten, always being careful to never be seen by anyone. The whole time I grew up I'd never had any girlie clothes of my own but I'd always worn my sister's things, even used her makeup. I always made certain that she never ran out of makeup too quickly. When I knew I had the house to myself, I would dress up and pretend I was a girl. These sessions ended in a...Read On

14

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allfours

Becoming Chloe - Part 12

A meal with a difference...

I walked through the door, and almost immediately all my resolve disappeared at the sight that met my eyes: my wife was sitting on the sofa with her legs spread wide with Tina between them, eating her out like no tomorrow! Vickie's knickers were wrapped around one ankle, and she held up her legs high to give her lover better access to her quim. It glistened in the late afternoon light with...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

17

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Dividence

The Cabin, chapter I

I accidentally stumble a "rich" crossdresser's secret cabin, thrilled by my find.

The latest months had been quite rough on me and I’d been looking forward to this trip for a long time. My girlfriend had left me, muttering something about me not being manly enough for her. In reply, I had buried myself in work and self-pity. When I finally came to my senses, I knew I had to take a break. My backpack was burdened by everything I would need, which wasn’t much. I...Read On

20

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allfours

Becoming Chloe - Part 10

Chloe gets fucked by Vickie's new cock, and then Vickie arranges a meet with Tina

As I started to strip off, Vickie insisted that I leave my bra, suspender belt, stockings and heels on. She lay on top of me on the bed, kissing me and fondling my smooth body, which was something I adored. I felt her hand snake between my legs and gently caress my balls. "Mmm, my baby feels full," she whispered in my ear before she started sucking on my lobes. Then she got up and went to...Read On

24

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tvk3983

Terry Gets It In The End

Terry's girlfriend finds him in panties and leads him down the path.

The converted attic was my room and it gave me loads of privacy. So as I grew up I could wear the clothes I liked, as long as I stayed in my room. By the time I was a senior in high school, I kept my toe nails painted all the time and I wore panties every day. At night I wore frilly little night gowns and more likely than not I would masturbate, always fantasizing that I was the girl and...Read On

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Crossdressing

The Magician's Assistant or How it began - Part 1

Becoming Chloe - Part 23

The Wedding Proposal, chapter VI

Late Night Bus

Becoming Chloe - Part 22

Dan a.k.a. Becca

Becoming Chloe - Part 21

The Wedding Proposal, chapter V

Becoming Chloe - Part 20

My Foggy Late Night Story

Erica Meets Sarah: Part 1

Becoming Chloe - Part 19

Becoming Chloe - Part 18

Park-n-Play

Becoming Chloe - Part 17

She Made Me Do It

The Cabin, chapter III

My 2 AM Phone Call

Becoming Chloe - Part 16

Becoming Chloe - Part 15

The Cabin, Chapter II

My First Time

Becoming Chloe - Part 14

Becoming Chloe - Part 13

Dana Finds A Lover

Becoming Chloe - Part 12

Becoming Chloe - Part 11

The Cabin, chapter I

Becoming Chloe - Part 10

Terry Gets It In The End