Crossdressing Stories

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Krystal's Crossdressing Story

How I first found out I was Born in the wrong body. It all started on a summer day I was 5 years old, I was just a child .It was 9 am my mom dropped me off at her mother’s house. I was there for the day. At around noon we sat down for lunch and I told my grandmother that I felt strange and that I did not understand my feelings at this point. read more >
 

Crossdressing True Confessions, Part Two

I had some difficulty getting in on the driver-side; it was very unlady-like. I moved the seat back and adjusted everything to accommodate my size. Then I practiced both getting in and exiting the small car. It took me about a half hour to get it down right, although, I could still be doing something wrong. I had to get my brain around moving and reacting as a woman would do. I just kept imagining I was a beautiful girl all my life. There is no need to act musculine. Getting my heels to work with the pedals was also a challenge. Realizing that I was going to be as comfortable as I was going to get, I turned the ignition and slowly pulled out of the garage and pulled onto our street. I wanted to get out of my neighborhood as fast as I could so as not to arouse suspicion with neighbors seeing a strange lady driving my wife's car. I felt more and more comfortable driving in heels as I hit the interstate and headed for downtown. But where should I go? I was almost just content on driving around for my first night out as a woman. Stopped at a light a car pulled up beside me and I turned to look. The blood drained from my face as I realized it was one of Myrtle's girlfriends. She rolled down the window to talk and I nervously looked around for the window button, what would I tell her? Her name was Katie, a cute petite red head that was always the wild one of Myrtle's friends... read more >
 

Crossdressing True Confessions, Part One

I really loved my wife; she was the most beautiful creature I have ever known. Tall, brunette and the longest legs you have ever seen. Myrtle's beautiful face is framed by her gorgeous brown hair. She was about 5'8" and had a great ass. Her curves were soft and very feminine, not a big chest but nice and perky tits I loved to play with. read more >
 

How I Became A Sissy Crossdresser

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. read more >
 

Why I Wear Pantyhose

I am a man who absolutely adores wearing sexy pantyhose on a regular basis. I wear pantyhose in the privacy of my own home but also under clothes when I am out and about, this makes me feel especially naughty. Pantyhose for men make me get that feminine vibe and I love the feel of them against my freshly shaved legs. I like to parade around in the mirror in my pantyhose, they make my legs look so sexy that I can't help but to stroke them and things sometimes go even further than that. read more >