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.

Like what you read, Sweetie?
Share with your friends 🎀

Twitter
Facebook
Reddit
WhatsApp
Tumblr
0 0 votes
Article Rating
Subscribe
Notify of
guest
0 Comments
Inline Feedbacks
View all comments

Get a FREE Sissy eBook!

Here’s your chance to claim one of our exclusive sissy eBooks—completely free! 

No strings attached, just pure sissy fun!

Discover more from Sissy Hive

Subscribe now to keep reading and get access to the full archive.

Continue reading