How I Became A Sissy Crossdresser

By Sissy

I was five 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 fosters mother's drawer and lifted and felt these mysterious garments. One late Friday 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. Once when I was engrossed in the feminine pages my mother walked by and I looked up at her with a smile on my face. She asked what I was looking at and I innocently showed her the pages of lingerie. She asked if I like it and of course I said yes. She smiled and walked away.

A couple of weeks later I was trying to find the catalogue but to no avail. I asked my mother if she had seen and she just yes, it was old and I did not need it anymore and anyway a new one will come next year. I was saddened and went to my room to get ready for bed. I opened my drawer by the bed to and saw an envelope with my name on it .. I opened it and there neatly folded were several pages of the catalogue. I said nothing to my mother nor did she comment to me. Within a few months the new catalogue arrived and my mother put it in my room. I was very pleased with what she had done and felt no guilt or that anything was wrong with what I was doing ( or she was doing) About two months after that my father was sent overseas to do an engineering project and would be gone the better part of two years. About a week after he left my mother asked me if I would like to help her around the house and keep her company..of course I said yes I helped with all sorts of household chores and loved it I learned ironing ( only nakpins and hankies) and how to make a cake and actually plan a meal On many of these activities my mother would be so proud of me she would hold me close to her bosom and rock me back and forth and then kiss me. I loved the attention and one time I tentatively reach out and put my hand on her breast She held it there of just few seconds and then abruptly got up. I was helping her with the laundry and she showed me how to separate the delicate things from other things and then how to fold them then she let me put them in her mysterious drawer. I told her I loved her drawer and at she sat me down and gave me a lesson in what women's underwear was and how it was made and sized and the difference between cotton and silk and nylon and satin.. I boldly and without thinking told her I would love to wear things like that. She smiled and said well maybe you can someday.

Not much else happened until I was eight. and I had a real girl friend who moved across the street from us. Her mother and mine became close friends and the four of us did a lot of things together from shopping ( I loved to shop) to going on road trips. That summer she and I went to a town sponsored day camp we were close as two young ones can be. We experimented with a lot of things She showed me how she could stand like a boy an pee into the toilet I showed her that I could squat like a girl and pee in the toilet, and then we decided to have a little pee party.. nothing serious because we both believed that pee was poisonous....which her uncle Henry told her it was not and I think taught her things about it..Which came out years and years later....anyway summer was coming to an end and the camp was going to have a dressup parade for the last half day of camp. 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 went shopping with Nancy's mom and the three of them got busy turning me into a girl We practiced the whole week and I can remember being naked in Nancy's bedroom and putting on my first ever pair of panties (pink with lace around the edges) and a soft cotton I had a training bra which felt wonderful and a cotton slip with a full skirt and then, love of life, a beautiful full skirted green taffeta dress with white cuffs and collar. When the three of them helped me put it on my mind instantly became very feminine. I felt like a girl and I danced around the room and twirled and ran over and hugged my mom and kissed Nancy's mom and then Nancy and the two of us grabbed hands and twirled around the room. I all felt so natural. The day of the parade was a bit different. I was afraid to get out of the car. Nancy called me a sissy and told me I looked great. The sissy term started that day and has been with me ever since. On the play ground there were about fifty kids 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 without a gaff 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. Day camp was over at noon and my mom was supposed to pick us up but she did no arrive until after five. So there we were two third graders ( going into fourth) and one other older boy who lived near the school. We played on the gym equipment and Nancy and I hung by our knees on a low bar at the insistence or our new boy friend. He came over to us as we both hung there with our skirts over our head and put his arms around us and his hand on our crotches.

Then as we sat around and played a game of dare and he dared us to pull down our panties. Nancy did it immediately and I hesitated. But finally did and then Nancy asked him which one of us he thought was the cutest. He said both but why does this sissy dress like a girl. And Nancy said it was because He is a girl. As four o’clock rolled by and our imaginations were running…When my mom came to pick us up she was all apologetic and we were both ok with that and we sat quietly all the way home and never discussed it again. When I got home I asked my mom if I could keep wearing my dress for the rest of the day and she pulled me to her and kissed me and said yes you can be my little girl for as long as you want. but I think it best to keep this between you and me and your little friend Nancy. And thus I became a sissy crossdresser. Years passed. My father came home and we moved to another state shortly after that my parents were divorced..my sissyness played a small part in their decision. I went through highschool with the usual temptations and in the process found religion which poured on me a deep sense of guilt. I dated girls but when I masturbated which I did regularly I always pretended that I was being fed hormones and turning into a woman. And then I got married and totally complicated my life as a bi sexual in denial.....but that is a story for another time.