Many years ago, I was slim, am not tall and developed a fetish for dressing as a woman. This is in the late 70s, early 80s. I was a scout leader back then and one of the ways we raised money was with classic jumble sales. On one occasion I saw one woman had donated a little black dress, very much in the Coco Chanel style. It looked hardly worn and I suspected she donated it as it may have become too small for her. It was size 10. At that time my waist size was about 28 inches so it would be a perfect, if a little tight, fit. It was also short and I reckoned it would finish a good few inches above my knees.
No one was looking so I grabbed it and stuffed it in my bag. I also managed to purloin a black wig, a thin, black suspender belt and a pair of white, cotton knickers. When the sale was finished I went home, took them upstairs and held the dress up against my front. It looked perfect. That night I went up to bed on my own, quickly slipped the dress over my head and assured myself it was a good fit, took it off and hid it from sight.
They sat without being touched again for some while. In the intervening period I also collected some inexpensive makeup. lipstick, mascara, eye shadow and a pair of black stockings.
Some time later, my wife took the kids out for the day and gave me the opportunity to dress up.
I hung the dress on the wardrobe door and arranged the wig and makeup on the dressing table, then took a long and careful shave to make sure my skin was smooth and no trace of stubble. In those days I was fortunate enough to to have much of a beard, only needing to shave ever few days.
When the prep was done I stripped naked, donned the suspender belt, pulled on the knickers and slipped the dress over my head, loving the feel of the thin, cotton material as it slid down my body.
I borrowed the wife's foundation and set to work applying the makeup on my face, starting with the foundation then the eye shadow, mascara and finally, lipstick. I set the wig on my head, making sure it framed my face then sat back to admire my handiwork. To my surprise, an attractive woman stared back at me from the mirror. She looked not unlike my very pretty, younger sister.
To finish the effect, I unsealed the stockings and rolled them up my legs, securing them with the suspender belt. Fortunately, my wife had the same size feet as me and I slipped my feet into the highest pair of heels she possessed. Lastly I painted my nails with some of her bright red nail varnish then walked around the house waiting for the varnish to dry, admiring myself in every mirror I passed.
Or wardrobe fitting had two full length mirrors on the front. Standing in front of it, I pulled up the hem of my dress, loving the look of my stocking clad legs made shapely by the high heels. As I pulled higher first the tops of the stockings came into view then the little panties with my, by now, erect cock outlined in white.
There was one last thing I desired to do. I wanted to feel the swish of the dress around my legs and feel of air around my legs and knickers.
I decided to take a short walk. Simple. I’d exit via the front door, go through the gate and re-enter the house by the back door. This I did. It was exhilarating, knowing that I could be seen and, I suspected not recognised. I closed the door behind me and tottered on my heels around the house and up to the rear door. Then it went badly wrong.
The back door was locked and I could not go back in at the front, it had closed on the night latch. I panicked.
Then looked up. My wife had opened all the top bedroom windows to “air” the house. We had no ladder but my son’s bedroom window was adjacent to the soil pipe. Kicking off the heels I began to climb. To this day I have no idea if a neighbour saw a woman climbing up the side of the house. Anyone below would have had a great view up my dress, but that was the least of my worries.
At the top I got my arm through the vent, unfastened the window, climbed over the sill and landed on the bed. I dashed downstairs, unlocked the back door, recovered the shoes and ran back up to begin the process of undressing, removing makeup and nail varnish then getting back into normal clothes.
I hid all traces of my dressing spree and went downstairs for a cup of tea. My heartbeat had returned to normal by the time the family returned and I was engrossed in my latest read.
I did do it again some weeks later when I had recovered my composure and the urge to dress rose in my again.
This time I ensured I could get back in. But went a whole step further and walked round the block, a distance of about half a mile. It went perfectly and I was most pleased
I have dressed since then on one occasion. I’ll tell that one some day.
Danny
