There are a couple that I have really enjoyed most. Shopping and trying on women's clothes in the dressing room was great. Having a profesional make-over and discovering my full femme potential was also fantastic. Good luck.
Answering the door to recieve a package from the the UPS lady wearing my thigh high boots with a 5" spike heel.
I love wearing my partners hoodies and sweatshirts and I wear his t shirts sometimes too. They smell of him and i love it :-)
I'm not a crossdresser now but when I was in my teens I was very feminine-looking and (according to my female friends), very pretty. Sometimes when I went to parties they encouraged me to dress up as a girl, and since I was gay (and just out of the closet) I thought it was a lot of fun. I was short for a boy, and delicately-built so it was easy finding girls clothes to fit. When I was dressed up and wearing make-up, and putting on my "girl voice", people thought I really was a girl. The experience I enjoyed the best was a "girl's night out" to a nightclub in Liverpool when I was 21. Not one single person guessed that I was a boy.
As an adult, it wasn't so much fun. I did dabble in the drag scene early on but I didn't enjoy the theatrical aspect of it and the makeup got harder once I was growing facial hair.
It's been twenty years since I last wore drag, and though it was a fun time in my life, I don't really miss it at all.
never having had 1,,, that's my #1
wearing a tuxedo to a party
The two times that I got to go out and pick out two formal gowns. I know that's a common thing to wear as a crossdresser but I will never forget going to JCPenny and trying on different gowns until I found the one I felt most comfortable in.
When I was 17, I found some of my mother's old clothes. I dressed up as her and was shocked that I looked just like a picture of my mother when she was 19.
I got a paddle, pulled up the skirt and pulled down the paddle and spanked myself.
I wish I had pictures of it.
Probably being accepted by my partner and actually being able to sit with her whilst cross dressed. Up until that time I had never been with another person (except paying for sex cross dressed) cross dressed only ever done it on my own. It was the greatest feeling.
You paid for sex while crossdressed? That ought to make an interesting story.
I always go out to eat in 5 inch heels and a silk dress with panties bra and my pretriest makeup and blonde wig
I got to go a a party dressed up. I loved it.
Going shopping and letting the salesgirl know it was for me. Being dressed and tsken with a ******* while s party room watched.