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Crossdressing

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.

29
BadDog9
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Discovery

The neighbor makes a discovery

How did I end up in this position?  This was the thought running through my head as I lay face down across the bed. My mind flashed back to the moment it all began. It was a beautiful Sunday morning with a cool springtime breeze blowing through the open window. I was cleaning the house. I hated cleaning, mostly because it is never fully done. No matter how much cleaning you do, there will...Read On

5

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

Made Maryanne - Part 2

John is made aware of his new role

When I woke up the following morning, I immediately became aware of the situation. It was difficult not to notice the pretty white cotton and lace nor the fact that I was wearing it. I quickly recalled the events of the previous night, feeling ashamed at having been caught masturbating. I knew that Beatrice somehow wanted to make a point by telling me to wear her nightdress, but I had no...Read On

8

Ready & Waiting (In my wife's lingerie)

My wife has me dress up in her lingerie while she goes off to get a massage.

“Billy, can I see you in the bedroom?” I walked down the hall and into the bedroom, surprised to see lingerie laid out on the bed. I asked, “What’s this?” “We’re going to play a little game today. I need to de-stress, and you’re going to help me.” “Help you how?” “Take off your clothes and go shower.” After my shower, I returned to the bedroom completely naked. And erect. I kissed Betty....Read On

14

Made Maryanne

John is unaware of the female power to crush his manhood

It was 3 am. I was busy whacking myself off in the bathroom when Beatrice caught me. She and I had only been together for a few weeks when I started taking a special interest in her underwear. I loved the smell of her wet pussy, combined with the cozy softness of the cotton panty gusset pressed against my nose. Wearing one pair, feeling the delicate material clinging tightly to my ass, I held...Read On

8

A Friend With Something Extra Part 5

Ian's meeting with Lorna.

The weekend had come to a close and Grant and Ian returned to school. There were only a few more weeks before Summer vacation started and that's when Ian noticed changes in his behavior. He found himself staring at Grant whenever he could do so and not get caught. Dressed in his everyday clothes Grant bore no resemblance to the sexy girl he becomes. Secondly, he stopped playing the online...Read On

3

Irene's photoshoot

Cute Tgirl gets into trouble...

It all started with a mail: “Hi Irene, I’ve seen your pictures on Flickr and I love them. I know you have been out only once but I also know that you are craving to do it again. So here’s the deal: I offer you a private photo shoot, I’ll dictate the poses and the outfit and I’ll pay you 1000 Euro’s for it.” Oh my god, she had been waiting for an excuse to go outside in Irene-mode again and...Read On

7

Jessie's Fantasy Chapter 5: Afterthoughts

Now that Jessie fooled a male friend, what is in store for our heroine?

After Tracy mouthed, “I love you” to me, I knew right then and there that Tracy not only loved me as a male but also me as Jessie. I could feel my cheeks get warm and flushed from her comment and my thoughts. This was turning out to be the best day of my life. My thoughts were interrupted when Mark’s cock softened to the point that he slid out of my backside. Now my thoughts were replaced...Read On

15

Now Or Never

Now or never, he thought as he dressed in the sexy, girly lingerie.

He was nervous as he drove to the mall. He had to remind himself that nobody knew what was really going on, and that men purchased lingerie all the time for the wives and girlfriends. Except his purchases wouldn’t be for his wife, who had unceremoniously left him two years earlier with little explanation. He had revealed a few of his fetishes and kinks to her, which she had given off...Read On

8

Jessie's Fantasy: Chapter 4 The House That Adam Built

Now that Jessie was picked up by her friend, what will happen in private?

What a crazy twenty-four hours it had been. It all started last night with me losing a bet to my friend John, one which I should have never lost, but did. My payment was to dress up as a female while going out with my friends until I was able to successfully have a guy try to pick me up. Earlier today, I went to my friend Tracy’s house and told her about my dilemma. After a few laughs, Tracy...Read On

13

The Long Walk

The longest walk to my mailbox, ever.

Friday . I get home from work around 9:30, and I head straight for the shower. Now most stories like this involve shaving smooth and things like that, but I'm not able to shave because my wife doesn't care for it. After my shower I go into my closet and get my clothing. I get my black bra and thong and slip into those, followed by tan hose and regular clothes. I have the rental company pick...Read On

13

Jessie's Fantasy: Chapter 3 The Night Club

Jessie's all set for her first night out. Will she catch a guy or be caught?

After an amazing afternoon with Tracy, Suzy, and Brooke regarding my transformation and amazing feminization via sexual acts that wore me out, it was time to meet my friends. Before we left, I called my friend John and told him that female Jesse would have to wait. I told him a little white lie that I had developed stomach flu and had been throwing up all afternoon. John told me that he...Read On

20

Jessie's Fantasy: Chapter 2 The Transformation

Now that Jesse and Tracy had fun, what else is in store for Jesse?

Here I am in the bathroom buck-naked and hairless. An amazing thing happened in the tub of my best friend's bathroom. My secret love and best friend Tracy, just had an amazing love making session. We were starting to get hot for each other after I dried off when the door bell rang, and her beautiful naked self ran out of the bathroom to answer the door. I started reflecting on what just...Read On

18

Jessie's Fantasy: Chapter 1 Losing a Bet

Jesse makes a bet that he couldn't lose. Or could he?

Nearly everyone has a sexual fantasy that they would love to act on sometime in their life. Unfortunately for some, it never becomes reality. There are many different reasons, ranging from having fear or hesitation, to fantasizing about someone they can’t have, or the situation just never presents itself. This is a story of one such fantasy. Hope you enjoy! It was a Friday evening and I was...Read On

10

576 Shadow Oak Drive - Part 2

Sarah and Molly arrive at the party and Sarah has another first experience.

As Molly drove down the highway, I sat in the passenger seat. Although I had always had a feminine side, I was experiencing all kinds of new emotions and feelings that I hadn't felt before when dressed. I don't know exactly what brought it out. Maybe it was the love and support of Molly. Maybe it was seeing myself truly dolled-up for the first time, seeing my own cleavage, having my manhood...Read On

7

Finally Pregnant

My wife finally inpregnates me

It was a lazy Sunday morning. My wife and I were sleeping in a little. As I went to bed last night, like I do most nights, I put on my sexiest female lingerie. I chose a tight little corset number that has garters attached. It was bright red so I also chose red panties and black stockings. I tightened up the waist to give me a more curvy figure. To fill out the bra cups, I chose some 3XL...Read On

20

576 Shadow Oak Drive - Part 1

Sam meets Molly

I met Molly on a seemingly random day. How could I ever have known she would change me forever? It was late April and I was working behind the cash register of a local department store. I was eighteen, just out of high school, and didn't have any sort of plan for my future. I figured that I would take a least a year off before applying to any universities. I liked working at the...Read On

18

Being Christy - Part 2

Caught by the neighbour!

To be honest, I was panicking. From the outside I looked like an average teenager. Skinny black jeans. Indie band tee, maybe a size too small on my Bowie-thin frame. Cherry red Converse high tops. Straight dark hair cut into a fashionable (if you were an NME reading indie-kid) boy bob. But underneath I was sporting skimpy black panties and stockings and suspenders, all ‘borrowed’ from...Read On

22

First Time Bareback

The first time I let my boyfriend fuck me bareback

I have written an earlier story about the first time my boyfriend Mike and I fucked. After our first encounter, I couldn't get enough of Mike and his cock. We went from meeting every other week to him spending some weekends at my house with me dressed the entire time. As we got to know each other better, we started to discuss our sexual histories and some of our fantasies. I could tell Mike...Read On

8

A friend with something extra. Part 4

Grant dresses Ian for the first time.

Ian woke up around 9:00 AM and headed to the bathroom where he found his clothes hanging on the doorknob. After dressing he headed to the kitchen where he found Grant drinking coffee. He looked like he normally did, there was no trace of the sexy stunning female that Ian had sex with last night. Where's the girl?" Ian asked pouring a cup. "She's gone for now, but she'll be back,"...Read On

16

A Friend With Something Extra.Part 3

Grant collapsed on carpeted floor of the living room. The ropes of semen his friend shot on his chest were beginning to crawl down to his bra. The ones on his bra were slowly moving down toward his belly. His tiny silky bikini panties were filled with his own cum as the sight of his friend's cock shooting on him had gotten him off. He looked up at Ian who was still sitting on the couch with...Read On

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A friend with something extra.Part 2

Ian and Grant test the waters.

Ian headed to the bathroom to clean up. As he did he allowed his mind to recall the most recent events of the evening. He arrived at his best friends house for one of their pizza and movie nights and discovers a sexy girl in his buddy's bedroom. He soon discovered that the sexy girl was, in reality, his friend Grant. He didn't look or talk like the Grant he knew, he talked and looked like...Read On

11

Becoming Chloe - Part 39

The Final Chapter.

The following week, I found myself leaving home for the last time as the person I was. When I returned, in a few days time, I would be a total woman. All semblance of my being a man would be gone, and I would finally be my true self. To help prepare my body for what was to come, Colin and I had abstained from sex since the evening when I got home from Tina and Vickie's house. That night,...Read On

23

A friend with something extra.

Ian makes a discovery about his boyhood friend.

So here Ian was standing in the doorway to his buddy's room and staring at this drop dead hottie clad in silk, lace and heels that he found inside. It was just a typical Friday and he'd dropped over his friend's house for a pizza and movie night. It was a rotating event for them on Fridays. They didn't have their own cars as of yet and had no desire to walk to the mall and hang out....Read On

7

Becoming Chloe - Part 38

Tina & Vickie get married

Well, the day finally arrived. After an incredible amount of last minute telephoning and running around, my ex-wife Vickie was getting married to her female partner and lover, Tina. They both looked absolutely stunning as they walked down the aisle, in almost matching white wedding dresses that I was quite envious of. At least as Matron of Honour, I did manage to get to wear a lovely...Read On

8

The Wedding Proposal, chapter VIII

An apology is needed, but how will we end up? Lonely? Pals? Friends? Friends with benefits? Lovers?

I was beginning to get used to this now. My heart had stopped racing when I ventured out the door. I did not examine every approaching face for signs of suspicion, or spend all my concentration on every little detail a women would do unconsciously. I walked onto the bus as a free and independent woman. Never questioning my right to be there. A text message arrived as I watched rows and...Read On

16

First Love

Crossdressers first love

This is the story of the first time my first boyfriend and I fucked. Before I get started I should give you some background information about myself. I had always considered myself straight and had been happily married for fifteen years before my wife and I drifted apart and divorced. While we were married I had wondered what wearing some of her heels would be like. Unfortunately my feet were...Read On

8

Being Christy - Part 1

Part truth, part fantasy. My story begins

The summer before I went to university was hot. Really hot. It barely rained for weeks and when it did, it came down in torrential downpours. The air would get heavy during the course of the hot humid mornings and by lunchtime the clouds would darken and you could feel that it was going to be getting very wet, very soon. The day I first met Jenny and James I’d been into town in the morning,...Read On

10

The Joy Of Becoming A Girl Without Kknowing It

Can it be that i have an effect on ... it

Thankfully a decent spring day arrived. With its coming brought out my need to be dressed, become and behave girlie and fem. I studied the weather patterns and made my plans to dress En-Femme with it. So that day finally was here. A joyfulness overcame me as I looked out my bedroom window and saw the sun glowing brightly. The sounds of chirping, singing birds was loud, crisp and happy. The...Read On

8

Becoming Chloe - Part 37

A little get-together...

A fortnight later, Colin and I were sitting with Tina and Vickie in a really good restaurant in town. I'd just received my pay-check for my last two films and Colin had landed a contract from a medium size company, so we were out to celebrate. Before we'd left for the restaurant, I had a good chat with Colin about something that I'd been organising for some time. Having spoken to Vickie and...Read On