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How it started.
To me, Crossdressing, it’s not just for fun’. Well it’s not. It’s an obsession. It’s the be-all and end-all of my life. I can’t remember a time when I haven’t dressed up, I was 6 when I first discovered the huge and heavy Sears Catalogue. I was intrigued by several pages of ladies in various posses of undress. The sight of girdles and bras and panties and garter belts and then over a couple of pages, silky slips and camisoles and finally nighties……Lace, lace, lace, and silk. On the first occasion I had I went through my mother’s drawer and lifted and felt these mysterious garments. One day I was sitting in a chair with the catalogue open on my lap. I held it there with my legs crossed and discovered that if I moved my foot back and forth I could feel a wonderful sensation in my crotch. I did not know what it was but every chance I had I would sit with my legs positioned to hold the catalogue and move my leg to excite my crotch. That was the beginning of my journey into Crossdressing.
I think I was about 8 and the school I went to was having a Halloween fair the evening of Halloween and I wanted to go. I went home and told my mom and she asked what I was going to go as and I said I am going as a cowboy.
She smiled and then she took my face her hands and looked at me and said I think you would be a much prettier girl than a cowboy. I was thrilled but scared and said I would not do it but in my heart and wanted to do that in the worst way. My mother got busy turning me into a girl We practiced the whole 2 days before the fair and I can remember putting on my first ever pair of panties (pink with lace around the edges) and a soft silky nylon. I had a white bra which felt wonderful and a white lacy nylon slip then, a beautiful full skirted green taffeta dress with white cuffs and collar. I twirled around the room. I all felt so natural. When I was dressed my mind instantly became very feminine.
The night of the fair my Mother dressed me in the clothes that I practiced in, only this time my Mother said a lady always wears stockings and heels. So she fastened a lack garter belt around my waist and showed me how to roll and pull up the stockings to hook them on the garters. Then she gave me a pair of black ankle strap low heels she got at the thrift store. Then she applied full make-up and a wig, I loved the feeling and taste of the red lipstick. She then drove me to the school where the Halloween fair was. As I got out of the car, my Mother called me a sissy and told me I looked pretty. The sissy term started that day and has been with me ever since. T the fair there were about fifty k**s and a lot of cowboys I was teased (like a girl) I was harassed ( like a girl) and I was also attracting a small group of boys that kept trying to feel me up. I was excited and aroused at the attention I was getting I was erect and only the wideness of the skirt kept it hidden. I won first prize for the most ‘interesting’ costume and when I got up to get my ribbon I spun around and pranced over to the table…to the laughter of everybody there.
When my mom came to pick up, I told her I had a wonderful time and showed her the ribbon I won, we sat quietly all the way home and never discussed it again.
Through the years, military service and getting married the feelings about dressing never left. I eventually told my Wife, she didn’t like it, but accepted it. And did support it a few times.
And now, more than half a century later, it still gives me a sexual thrill when I slip into something silky and put on some make-up. It’s not JUST the clothes, I become a new person when I dress, there’s more girl than boy in me, and it all comes out when I dress. I prefer my femme side, She’s much nicer than the boy-me, apart from looking a lot sexier than boy-me.
I always thought of myself as straight and never dressed in public, except under my clothes at work. I always wore silky panties, stockings or pantyhose, slips, and camies. Still do to this day. I did meet another crossdresser, she never knew I dressed as well and we had sex. And it was so erotic and fantastic. We met when we could, and I did meet 4 others over the years, all wonderful ladies that I still have feelings for. I was always the male, and always the top. I wanted so much to be with them dressed and be the bottom. But it never happened. I did experience the pleasure of sucking a real cock and tasting warm cum. And that’s another story to tell sometime.
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