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Hello to all the pretty ladies who are members of this website. I have been crossdressing since my adolescence, but tried to stifle the ever-present urge to express the female side of myself. My crossdressing bloomed into flower after I was discharged from the US Army in 1974, and I moved to Tucson, Arizona. There I spied my former college roommate’s sister’s wig hanging on the wall in her bedroom in the ranch house in which I lived on the outskirts of Tucson. My heart raced. I immediately began to apply makeup, and put on her clothing, from her pantyhose and bra to her short skirt and cute matching top, and her sizable high heels. I affixed her wig onto my head, clipped on my earrings, put a necklace on, sprayed some perfume on my neck and walked nervously out to the car in the attached garage. I backed it out, and set out on my very first womanly outing. My wig was a long frosted light brown one with blonde highlights. I drove out to a main road and proceeded to travel along to the outskirts of the outskirts. Continually checking my pretty self in the rear view mirror, I stopped along the side of the road, got out and lit a cigarette, smoking it in a very feminine way. A driver sped past and honked at me! I knew then what my future would hold: I would continue to dress up and soothe my inner self. My crossdressing life shifted into high gear when I moved to Boston and lived in an apartment in Brookline. There I acquired three beautiful dresses and another wig along with some breast forms and a full array of jewelry and makeup. My next door neighbor (a very pretty Jewess) discovered my inclination, and both approved and encouraged me in my pursuit of the woman deep inside me. She directed me to wear a pencil skirt and carry a clutch bag as we took leisurely strolls about the neighborhood. She and I shared cigarettes as we walked down the street and I have never felt more natural or at home. Later, I moved to a suburb north of Boston and would make periodic visits to a crossdresser’s shop in nearby Wakefield. The proprietor would give me a full makeover, and snap photos of me sitting demurely out behind her shop on a set of stairs. I would continue my forays to her shop in full drag (including a long blonde wig, a black miniskirt, purple V-neck top revealing my cleavage, gold dangling earrings, false press-on fingernails, black high heels, and flawless makeup) driving the ten miles to her shop while I smoked Virginia Slims Menthol Ultra Light 100’s smiling at other drivers who had come to a stop at a red light in another lane. They seemed to understand me and would smile back at me which gave me great confidence that I was passing as a woman. When I would arrive at the shop, I would park nearby and walk gracefully to the door. When I would pass inside, the proprietor had an automatic wolf-whistle, which was wonderful. She would then take many pictures of me in various female poses, and call me a “supermodel,” and ask me if I were living as a woman. Oh! If only! Those were the most blissful times in my long life, during which I have struggled to keep Maura from taking over her male ego. Some of those pictures I will try to post on this webpage. Cheers. I hope you all feel as fabulous in women’s clothing and makeup as I do.
Hi Maura, I enjoyed your story and Welcome to the CDH ! many us have a similar story.I have
been a Cross dresser for all my life on and off and for the last 10yrs I have been dressing more and more and have been out in public several times also. Also did basic training in the Army at Fort Dix,NJ. I wish I could share my dressing with other girls. Its always good to read about the other girls experiences also . Always open for Chat with others also.
Hugs Stacey S
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