Crossdressing Stories

10

allfours

Becoming Chloe - Part 29

Chloe gets an invite she didn't expect, and then an offer she may not be able to refuse!

One Tuesday morning, about a month later, I got a call from Colin. "Are you busy?" he asked. "No, not really. Why?" "We're doing a shoot in town. I thought you might want to come and see what I actually do for a living." "A shoot? What kind of shoot?" "Why not come over and see for yourself?" he asked. At times, he could be annoyingly evasive! Just one of his many charms, I suppose....Read On

8

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allfours

Becoming Chloe - Part 28

Chloe has her boobs done, and Tina has a son.

Three weeks later, I found myself lying on a hospital bed about to go into theatre. Colin held my hand as they came to give me a sedative before wheeling me out into the corridor, and the last thing I remember was him telling me he loved me as the world slowly went dark. I awoke feeling very groggy, and as if someone had been jumping on my chest. I heard Colin call for the nurse, and then I...Read On

19

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rushman1uk

Office - Caught 2

I couldn't focus, my head was racing with all kind of thoughts. I had no idea what this would result in. My manager and teammate noticed something was wrong. I just told them I was coming down with something and felt ill. As there was only about an hour before closing time, my boss told be to finish early and get myself home, dosed up and to recuperate over the weekend. I didn't need to...Read On

3

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Dividence

The Wedding Proposal, chapter VII

No sex. No eroticism. Just a good, old intermission.

I did not speak with Tony after that. Tina sent me a few messages, though I do not remember giving her my number. She was still in town and kept nagging me about meeting her again. I tried to refuse, although I lacked any convincing arguments. Even though I was a bit down about my row with Tony, I tried to go on as usual. The following Monday, after a night of constantly interrupted sleep,...Read On

Added: 06 Apr 2016 | Category: Crossdressing | Avg Score: 4.67 | Words: 1,056 | Tags: crossdressing friends emotion

14

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rushman1uk

Office - Caught

Guy gets caught by work colleague wearing tights

My name is Peter. I'm twenty three and I'm a member of the small internal IT team at a large corporation. It's a typical office setup and our small team of three were kept busy with the day to day tasks; failures, PCs and printers and general support. I'm generally pretty quiet and unassuming and, whilst polite and good at small talk, I'm pretty shy, so just keep my head down and do my job....Read On

7

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allfours

Becoming Chloe - Part 27

Colin asks Chloe to move in, and Vickie and Chloe have a conversation...

Shafts of golden sunlight came flooding between the small gaps in the curtains, and I watched small specks of dust roll and tumble in the beams. I lay in my lovers' arms, contented, despite the dull, persistent ache between my legs. We'd hardly slept, having made love nearly all night, and I knew I'd pay a heavy price for it later that day. Still, I felt that it was more than worth it. My...Read On

7

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allfours

Becoming Chloe - Part 26

Chloe makes progress with Vickie, and Colin invites Chloe home...

That night, we had a wonderful meal at an expensive restaurant in town. It was the first time Vickie and Tina had met Colin properly, and he charmed them beautifully. Really, this was the moment when Vickie and I became part of two different couples, which was kind of what I was hoping for. Colin was the perfect gentleman, attentive to my needs and sitting next to me, holding my hand. I...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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allfours

Becoming Chloe - Part 25

Chloe pays the price for losing her virginity.

The next morning, I awoke to the sound and smell of Colin bringing us coffee and toast. The smile on his face was lovely, and I couldn't wait for him to put the tray down and kiss me. Once he'd leaned over and gave me the most wonderful kiss, he took off his dressing gown and slipped in beside me. We sat and ate our toast and sipped on our coffee, saying little, but just happy to be in...Read On

10

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allfours

Becoming Chloe - Part 24

Chloe loses her virginity...

We sat sipping our wine, our feet rubbing each other. I felt contented and just a little woozy from the alcohol as I cuddled up to my man. We sat like this for a while, content in each other's company, like countless other couples up and down the country on a Saturday night. Occasionally Colin would kiss me, and sometimes I would steal a kiss from him. Slowly we moved so that Colin was laying...Read On

8

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ThePhantom

The Magician's Assistant or How it began. Part 2

Ken's life changed dramatically since under going the transformation at Mistress Elaine's. His time at the gym was spent doing high reps with low weights, concentrating on his legs and rear. He added a lot of cardio and crunches and this gave him lean muscle mass rather than bulk. As a result his whole body took on a toned and sculpted look. He worked on his makeup almost every night and...Read On

10

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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

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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

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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

13

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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

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Crossdressing

Becoming Chloe - Part 29

Becoming Chloe - Part 28

Office - Caught 2

The Wedding Proposal, chapter VII

Office - Caught

Becoming Chloe - Part 27

Becoming Chloe - Part 26

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

Becoming Chloe - Part 25

Becoming Chloe - Part 24

The Magician's Assistant or How it began. Part 2

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