Cross-dressing - the beginning

I would assume that for most men, interest in women’s clothing started at a young age. For me, this occurred when I was 11 looking through the Littlewoods, Gratton and Freeman catalogues that my mother used to have.

At the time, I lived with my mother Jane, who was divorced, my b*****r Anthony and s****r Sharon, who were five and three years older than me. It was quite easy to sneak one of the catalogues up to my room and thumb through them. If one of them had bothered to look at the catalogue, all the lingerie pages will have been well marked with my mucky fingers.

Staring at me from these pages was a series of women I thought “Oh I wish you were here in my bed so that I squeeze and suck those firm tits”. Turn onto the knickers section, and I would think “Wish I could take those pants off and finger your juicy pussy”. Slips, half-slips, nighties, tights, stockings, girdles, panty girdles and corsets were all the same. My cock would be stroked and pounced until I shot my load – but not into the catalogue to make sure that my “habit” wasn’t found out.

After a few months of looking at lingerie, I eventually got into fashion pages. An array of dresses and skirts, blouses and tops, and knitwear that all seemed to shout at me. Gradually I took and interest started to admire what looked nice on these models. I don’t know how long after I started looking at these pages that I began to wonder what they would look like on me. With this realisation, the urge to dress-up was now essential but how I was going to do this I did not know. Two days later, on a Saturday, my opportunity came.

For some reason, mum had to work whilst Anthony went to soccer; Sharon was doing her Saturday job to buy clothes. I sneaked into mum’s bedroom and went looking in her wardrobe and drawers. Very quickly, I found a pair of blue nylon Platex panties, tan tights, full-length white slip, a 36B white bra, and from her wardrobe, her long red dress, all of which I placed carefully on the bed.

Having stood there staring at them for what appeared to have been an eternity but was only a couple of seconds, I stripped and left my own clothes in a heap at the foot of the bed. I pulled the panties on and then stroked my cock through the material and could feel it begin to throb. Next came the tights, followed by the bra and slip, again stroking my body through the material. Finally I stepped into the dress and buttoned it up before standing in front of the mirror.

There I was, stood in women’s clothes for the first time. I began to stroke my chest where the tits should have been, and rubbed my cock through the dress. After a few minutes, I needed to be satisfied and so up came the dress to my waist, down came panties and tights and pounded away until cum spewed out. To say it was the best wank I had experienced could not describe the feeling at that time.

However as I came of the high and looked at myself in the mirror, I thought “no, this is all wrong”. I stripped and carefully put everything back in its original place, vowing never to do it again. But by the following week, the urge to dress-up again was strong and I was all along in the house on Saturday afternoon.

Rather than mum’s room, I went into Sharon’s room knowing that if she every caught me or fond out the bitch would kill me and make my life a living hell. Out of her drawers I took a pair of her white cotton knickers along with the white thigh length stockings she wore to school. From her wardrobe, I took her school blouse and knee-length nay skirt to try on. Finally I took out a pair of strappy mid-heeled shoes just to complete the outfit.

Again I dressed up, squeezed and rubbed parts of my body. As I was wearing the shoes, I totted around the bedroom and admired myself in her bedside mirror before the need to wank was a necessity. After the high, I again felt it was wrong, stripped and put everything away, vowing never to do it anymore. But as every cross-dresser knows, the urge to dress up will always raise its head and I was no different.

After a few weeks of denial, the urge became unbearable and I had to dress up. So everyone appeared to be out for at least four to five hours every Saturday afternoon that was the time to dress-up. Over time, the urge to wank having just dress-up subsided although I needed to have this release before I changed. Five minutes became fifteen, which became thirty and eventually an hour, and then two. Two became three and eventually four hours which I would limit myself to.

I became bolder by strutting around the house, upstairs and downstairs, doing my chores dressed up before mum came home. To help form tits which I could stroke, I stuffed a couple of half-slips into the bra cups. However at the end of my private session, I would carefully put everything back in their original position thinking I would never get caught.

How wrong I could be with that thought.
51% (10/10)
 
Posted by Derk67
4 years ago    Views: 252
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2 years ago
I was the same I use to dress have a really good wank then feel disgusted, I haven't been able to give it up...
3 years ago
sounds like you had fun, i used to do the same it was soooooooooooo good
4 years ago
Nice I like the sound of the red dress mm:)

sexy regards Meranda xx