I am often surprised how very well my members present their stories of their first time crossdressing. Alexis posted this as a comment in My First Time, however I felt the story was so well told it deserved a post of its own. I hope you enjoy this beautifully told story. FD
Its tough for me to really pin point a “first time”. Over this journey there are many milestones. Let’s start with the big cliche (although true). When I was young, I would steal my sisters panties. When she went away to college, she left 3 pairs of satin panties in her dresser. The first time I tried one on, I knew it was ridiculous but I almost came right off the bat. I kept those pairs for years and used them every time I jerked off….and that was a lot.
During high school and college this urge subsided. When I entered the real world, I was quite a party boy and I loved cocaine. Cocaine and porn became hand in hand and I stopped going out as much and I’d get my stash and start staying home. Just me and my shemale porn (regular porn became boring quick). Unfortunately, the downside here is that coke makes your dick shrivel and regular masturbation almost impossible. So I started looking for things that would get me more turned on and able cum during these moments. Panties reentered the equation…then anal toys….then lingerie…
I held on to these kinks and evolution took hold. For about a decade that held me over… However after I got married and had a kid, the partying had to stop (ok…slow down more like it). Eventually, my lingerie sets, panties, and stockings just weren’t doing it for me. I wanted…needed something more.
I found a store in our town (as luck would have it) and invested in some heels (which had been hard to sneak around and find a size 14) and a couple of dresses and a wig.
Eventually I told my wife (who was aware of my previous kinks) that I wanted to try to go full femme and see how it looked. It was the first time and I even got her to play the domme role. Strap on and everything (first time and I had always wanted it). She even did my makeup which really opened up my mind. I finally actually kind of looked like girls. Not just a dude with a beard in ill fitting lingerie. Shaved the beard the net day (which was tough but internally it was a sign I was ready to commit. She was cool about it but was doing it to spice the sex life up…we had a 1 year old baby and we were exhausted 24/7 and weren’t having sex, so anything was worth trying.
I LOVED it…but didn’t want to tell my wife how much…so I started experimenting on my own. A few more pairs of heel and dresses…but sneaking them around my house hiding these things I paid good money for was becoming unacceptable. I had to tell her where my mind was at. I couldn’t accept living the rest of my life hiding it so fuck it… There was a good chance she’d be cool with it but it was a risk anyway.
So on Christmas Eve eve, I couldn’t sleep it was all that I could think about. When she woke up in the morning, I turned to her and said, “I can’t sleep anymore, I have something on my mind you need to know. I can’t hide it but every night when you go to bed, I get a dressed as a woman, and I can’t live my life hiding it and I have to be open.”
Her reply? “Awesome, I kind of already knew this, but if that’s who you are, then I’m all for it”
Over the last 4 months, our relationship has never been better (except the credit card bills). Going shopping together is SOOOOO much fun. I now have my own panty drawer, bra drawer, lingerie drawer, stockings drawer and half the closet full of dresses, skirts and blouses. Even moved my dude clothes to the guest bedroom. I work from home…so dude clothes only get used a couple times a week.
Anyway, my name is Alexis now. No one knows but my wife…and daughter (but at least shes growing up in a more accepting world). Every day I go a little bit further. Yesterday I tweezed my eyebrows. That was fun…. Anyway, this became more of a life story, but if you made it this far…thanks for reading.