I am 29 years old and have been crossdressing since about the age of 10 or so. I started out by trying on bras and panties I stole from my mom's drawer. I don't know why but I even stole a few panty liners that I wore just because it felt feminine I'm not even sure. Eventually, I tried on other pieces of clothing including dresses, tight pants, stockings and high heels. I also did try out makeup, lipstick and the like.
I eventually came to realize that my obsession with crossdressing came down to a few items I REALLY needed. Bras, lace panties and stockings. Over the years, I would continue wearing them under my clothes at school or later at work. It wasn,t so much the thrill (because it was there) but the feeling that it felt just right. Fast forward a few years and I am coming out of a bad relationship that lasted five years.
During this relationship, I would still crossdress in secret when my girlfriend was not around but I would never be able to wear them when I felt like it. After we broke up, the first thing I did was go on the shopping spree of my life. I had never shopped for women's underwear by myself since I always stole or borrowed them. I walked into victoria's secret with a huge "I don't give a damn" in my head. I bought so much stuff it was insane.
I was there looking at the bra's padding, holding panties in the air to see how they looked gauging the size I would need and that would be appropriate for me. When I left the place, I felt too good, like a kid that just walked out of the toy store with an unlimited credit card. I just felt so good that day and couldn't believe I had actually done it. I had no regrets after and wore the stuff I felt like around the house alone and had fun matching clothing and just going on with my day.
About a year later I met another girl and we started dating so I obviously stopped crossdressing because I really liked her and thought it would put her off. Eventually, I came out to her and told her everything. I won't post the details right now to not derail my post but I will explain after my story.
I was VERY surprised by her reaction. She understood and was fully supportive. She asked me if I wanted to try on one of her bras and wear it during the day and I nervously said yes, I could hardly even believe what was happening. Things went on and I would basically wear panties and bras whenever I felt and we even went shopping together to buy some things for me that would actually fit.
A problem rose a while later. I asked her during forecourse if I could slip on some lingerie. She accepted (probably in the heat of the moment and not because she genuinely wanted me to). We had sex but something struck me after the act: I enjoyed sex so much more if I was dressed.
(post will continue, sorry for doing this but I am on my phone and I'm afraid of losing the post if I do it all in one shot)