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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.

2

Freedom. What The Hell Do I Do With It?

A letter win leads to unhappiness and then freedom. How do you live a new life off the leash?

Freedom? What to do with a large lottery win.   So, I returned to the world of being a single man. A liberation of sorts, a return to uncertainty at a certain age. It is a scary place to be, ejected from the family home and to set up again.      Sure I have the comforts. Sure, I have all my books, the CD’s, plenty of DVDs. Ok, the furniture in the new place isn’t that good yet and I could...Read On

4

Getting More Daring At The Bookstore

Pushing the envelope dressing, pays off...

It was late spring, almost summer. It was too hot to wear my usual jeans and tight shirt, covered with a coat, to the adult book store. I was also getting bored with the same outfit every time. Since I was usually accepted, once inside, as a woman of sorts, I thought I’d push the envelope further.   Someone had given me a t-shirt years ago that was far too big for me. I kept it in my shed...Read On

8

The Brother Bride

Julie's brother does her the favor of a lifetime, which lets his own wish come true.

My twin sister Julie and I had always been close. Growing up, we shared each other’s deepest secrets. I had always told her I would do anything for her. Julie was a girly-girl, and loved being female. She had said she would be happy if she could wear dresses and heels all the time. Her wardrobe reflected that. She had also known about my urge to wear female clothes since we were young,...Read On

19

Back At The Adult Bookstore For More

Taking the next step in the bookstore while dressed...

After several positive experiences with sucking dick, including swallowing, I started going to the adult bookstore once or twice a month. As always, I would stop at some obscure spot and change into my female clothes. Then, I would put on a coat to walk from my car in the parking lot into the bookstore where I would pay the clerk for entry into the darkened “theater”.   It was really...Read On

12

House Sitting For The Holidays (part three)

Transforming into a sissy...

We had been texting for a few days following our date, even spending a few late nights sending erotic messages to each other. Jackson seemed desperate for another date and I couldn't stop thinking about his cock. I lay sprawled across the suede sofa in the front room playing with my hair, wearing a bra and thong, some shape pantyhose and a pair of six-inch black high heels. I'd...Read On

2

Evie Becomes Tilley

Tilley gets pimped out

A couple of weeks ago I’d sent a message to Mistress Jane saying that I’d managed to arrange a free weekend at the end of the month. Mistress Jane had promptly replied that she’d check her diary to make sure she was available. The next day I received a text from Jack saying that Mistress Jane had asked if he was free the same weekend and if so, would he like to pick me up from the train...Read On

19

Beginnings at the Adult Book Store

A man takes cross-dressing to the next level...

There are two types of cross-dressers. The first are those who dress all the time. They are usually quite passable since they spend a great deal of time and effort. The second are wannabe women who live in a world where there are circumstances that prevent them from being full-time out of the closet cross-dressers. They are usually not passable since they cannot shave their entire bodies,...Read On

15

House Sitting for the Holidays (Part two)

The sissy adventure continues...

By the end of the first week, I had completely transformed into a girl. I no longer wore men's clothing and my daily routine now consisted of showering, shaving and practising my makeup techniques before deciding on what outfit I was going to wear next. I had completely succumbed to feminization and needed to dress slutty in order to feel fulfilled. On this morning I rifled through the...Read On

8

First time going out for a while.

I did have to walk back to my car with cum stains on me

I haven't been dressing much lately. I haven't been doing anything fun really. I've had a lot going on, and just haven't had the time. Friday night when I got home from work, I just plopped down on my couch as usual. I don't know what made me horny, I hadn't been out in weeks, hadn't fucked in months, hell I hadn't even jacked off for a week, but for whatever reason I was rock hard and...Read On

12

Attractive to a Fault - Part Two

A crossdresser learns about feline sensuality

Jack seemed more than surprised when he set eyes on me. I was soon aware that he also seemed quite pleased. As I stood in front of him dressed in sheer red silk, looking like a true bedroom seductress, I realized the true error of my ways! What in the world was I doing? Why on earth was I suddenly standing in front of him practically naked, like some kind of sensual, naughty sexy slut? ...Read On

5

Being Joann

Moving from becoming a cross-dresser to being a cross-dresser.

I sat in front of my computer and started surfing transgendered sites when I came across an article on psychiatrists specializing in cross-dressers, transvestites, and transsexuals. Some of their treatments included a psychological evaluation, hormone therapy, group sessions, and preoperative assistance. The mail order hormones I was taking were having some positive effects, but I read...Read On

16

Attractive To A Fault

A pretty teen crossdresser's search for her identity

Events in our lives can often change us in ways we never expect. In my case I certainly felt different as a young boy. I possessed very real, mysterious, unexplainable, emotions that I can describe only as feminine needs , in spite of being athletic and quite normal in appearance. These internal feline longings and desires were intense and drew me to all kinds of feminine things. I knew that...Read On

3

My First Meeting With Mistress Zara

Maid ruby makes her debut.

First time with Mistress Zara – Chapter One. I am naturally nervous as I arrive at Her door. I ring the bell, and almost immediately the door opens and there stands Her full-time permanent maid, vikki. She is wearing sparkly pink platforms, white seamed stockings, a blonde curly wig, full makeup including the shiniest pink lipstick you can imagine and the most gorgeous dress I’ve ever seen. ...Read On

36

Colour By Design

What can be more exciting than an immaculate manicure?

I wouldn’t say I had a fetish. Isn’t wanting to look fabulous perfectly normal? I hate to say, but when you are the wrong side of middle age you readily grab any potential advantage with both hands. Particularly when you were born a male and your feminine side finally, finally, wins the identity battle. And that’s despite the cruelty of the rolling years removing the last illusions of...Read On

27

Double Header Quickie

First time with two guys

As noted in my previous stories, I am a divorced, bi cross dresser and live in a rural setting. Although there is a paved two lane road that runs in front of my house, I am up on a hill and a good 100 yards from the roadway where the traffic usually goes by at 50 MPH or better. So, I am comfortable working out in the garden wearing very little, sun bathing on the deck in a little string...Read On

34

House Sitting for the Holidays (part one)

A favor for a friend turns into a sissy adventure.

My friend Teresa was planning her summer holidays but was beginning to stress about leaving her home unattended for such a long time. She lived with her husband in a large house in the middle of nowhere and the two of them were planning a cruise, which meant the house would be left empty for the next eight weeks. She invited me over for lunch and after the meal, we sat down in the front...Read On

5

Stage Ten Of My Journey To Becoming Joann

Nearing the end of the journey to becoming a full time cross-dresser...

I was excited about the next soccer practice. There were no guys at the last practice due to Gurls Night. I was hoping Donny would be there this week. I stopped working at 4:00 so I would have enough to time to get ready.   I went into the bathroom and filled my douche bag with a little over two quarts of warm water and special soap. I took off my shorts and panties before pushing the...Read On

8

My Neighbor's Wife Pt. 2

I've never been so humiliated, but was loving every minute.

Suddenly, I was awake. Or was I just dreaming? It was hard to tell. Then I tried to move but couldn't. I could feel that what I was wearing when I last conscious, had been removed. I was naked, except...  The last thing I remember was being face down and Carol on top of me steadily fucking my ass, somewhere in all that pleasure and pain, I must have either past out or have withdrawn inward....Read On

6

Stage nine of my journey to becoming Joann

Moving into the last stages of becoming a complete cross-dresser

It was almost midnight when I got home from my foursome. When I walked into the house Mandy was sitting on the couch watching the television wearing a shear teddy with nothing underneath. She looked at me and said, “Where have you been all night young lady?”   I answered, “Out with the boys, Sis.”   “I hope you don’t mean what that sounds like.”   I responded, “If it sounds like I had...Read On

23

Practice Pays Off

First time out in public dressed as a woman.

It was a beautiful Saturday late afternoon. I was done with all the things I had to do around the house. My wife was gone for the weekend and I was feeling a bit bored. I thought I would take a shower, shave and pull out the makeup and see if I could do myself any justice in looking passable. Many attempts before had failed, but I was getting a little better each time. I got out of the...Read On

10

My First Time Out On The Town All Dolled Up

I learn about a sex club in Los Angeles and attend, with delightful results.

It was Christmas time but still warm in Los Angeles.  I was living in West LA and heard about a club called Club Sex Addict in the valley, a haven for crossdressers.  I had a fairly extensive warddrobe that I bought in a Culver City lingerie shop.  I just bit the bullet and went there and told the girl who worked there that I was a CD and she would help my pick out sexy slutty stuff to wear....Read On

10

Jack Has A Secret.

Jill's fuck friend has a little secret.

“When is he due back?” “Who?” Audrey gave Jill a look. “Oh, you mean Jack? Not sure actually.” “I call that bullshit. You know exactly when he will be back.” Jill smiled dreamily . “Yeah, tomorrow at 8.15pm.” “And by 9.30pm you will have his cock deep inside you?” “Hopefully.” “How long has he been gone?” “Three months almost, hiking in South America with his other macho friends.”...Read On

8

Getting More Than I Went For

I went to the mall to get one thing and came away with a lot more than I could have ever imagined.

Recently I have started looking online for woman’s clothes that I could wear incognito. I am on the larger size so I was searching plus size stores when I found something on one of the websites. It was a black lace bandeau which seems to be a bra-like garment that you can wear without straps. It seemed very sexy and I thought, perfect, no straps and it should be tight enough that no one...Read On

10

Stage eight of my journey to becoming Joann

Big steps as a cross dresser

After returning home from dropping Mom and Dave off at the airport, I immediately jumped in the bathtub and took a long bubble bath. While I was in the bathtub, I shaved the stubble that was starting to form from days of neglect. When I finished my bath, I rubbed most of my body with a good lotion to restore its smoothness, followed by a badly needed pair of sexy red lace bikini panties with...Read On

12

Turning into a Middle Age Slut - Part 1

Once I go fem, there is no turning back.

I have had the crossdressing bug for many years and have collected some items to fully dress with, such as a wig, makeup, fake boobs and all that makes me look as fem looking as possible. Being in my mid fifties however, there was really no way that I was going to be truly passable or that hot, so I thought  Over the years, I collected my lingerie, heels, wigs and experimented with makeup. ...Read On

18

Getting A Grip On The Situation. The Conclusion.

"You OK, son?" Dad asked Van as he saw him shift constantly in his kitchen chair. "Yeah, Pops, I'm fine, just a little sore. Went to the BMX park and for a couple of hours and then a group of us raced through the woods," Van responded. "You need to slow down. That's too much abuse on your body for one day, " his parent responded knowingly. 'If you only knew,' Van said to himself before...Read On

12

Getting A Grip On The Situation. Part 3.

Ken was sent home in plenty of time so Vanessa could become Van again. Van thought about the morning events as he stepped in the shower to remove his makeup and continued thinking when he returned to his room and carefully hid Vanessa's clothing and makeup. This long and laborious process was necessary as discovery by his parents would be disastrous for him. Still wrapped in a towel he...Read On

14

Getting A Grip On The Situation. Part 2

Ken felt himself being shaken and heard a voice urging him to wake up. When he opened his eyes he didn't know where he was for a second until he turned his head and saw Vanessa next to him. "Hey babe, you've got to get up and moving. It's getting late and my parents will be home," she said softly. Ken was out of bed like a shot and quickly redressed. He must have been so deeply asleep that...Read On

18

Getting A Grip On The Situation.

As our story opens we find sixteen-year-old Ken almost naked and laying at Vanessa's side enjoying the slow descent from his orgasmic high. The wonderful feeling is made even better by the fact that Vanessa's body is pressed against him and one of her satiny smooth legs is on top of his leg. He smiles to himself as he glances over at her and recalls her asking him not to tell anyone. It...Read On

6

Hard #2

An unsual situation.

Well, that didn't work out well.  I mean, we're fine at work, but once again, you're all proven right.  I accept what's been said and that I deserve anything else you have to say about me.  Well, maybe not anything, Azalea.  Remember to keep some thoughts to yourself, my love. In unrelated news, I've been wearing pants the last few days.  It's weird, but ultimately okay.  I get that...Read On


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