Top 10 Crossdressing Sissies Stories

My Journey into Crossdressing

My interest in female clothing began at an early age, I don’t know where it came from or why it is so powerful. I started with a pair of my mother’s pantyhose, from the moment I put them on for the first time, the bug had a hold on me.

From then on I would put them on every chance I got, that got to the point where, that was not enough, I started taking huge risks on getting caught but I didn’t care. The next thing I knew, I was putting on my older sister’s panties & bra along with the hose, it seemed that every couple of months I had to add more clothing.

By the age of 13, I was dressing completely & starting to experiment with makeup & hair, by the age of 14, I was sneaking out of the house at night completely dressed as a girl. That lasted until I was 17 years old, that’s when I learned about shaving my body & wearing nail polish on my fingers & toes, I let my hair grow out & I was taking some of my mother’s supplements to help grow my nails.

At 19 years old I met my ex wife, I thought that would be the answer to my dressing up boy, was I ever wrong, having all of my wife’s clothes,  shoes, makeup & nail polishes at my disposal, I just withdrew from everyone & stayed home & dressed up.

My wife hated my dressing up & because of that, that is how I found out about plucking ones eyebrows & having your ears pierced, my wife would threaten to tell all of our family & friends about my dressing up if I didn’t stop doing it well, one time I told her to make me up as a woman then go ahead & tell everyone that I want to be a woman, so she did.

She double pierced my ears & plucked my eyebrows into really thin, highly arched lines, when she was all done with my makeover, I looked in a mirror then told her I loved how she made me look & I asked her if she would take me to a beauty salon to get my hair cut, colored & styled, she gave me a resounding no.

She did, however bring a number of her co workers by the house to meet her sissy husband who wanted to be a woman, soon after that she left me.

With her gone I began dating men & I found that I loved being with men, I never had a shortage of s*x. I know that I will never stop dressing as a woman, I couldn’t even if I wanted to so I just embrace it & be who I was meant to be.

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