So many fun experiences I can recall throughout my Life of conversations I was able to steer in the direction of me being dolled up by the female I was talking to. In so very few cases did I actually end up in dresses but just the joy and evil smiles the girls/Women had in their faces was unforgettable ! Women are so fun and imagininitive about everything but when the idea comes up of getting to see a guy have to wear their dresses it just would reach another level of giggles and happiness.

At work the women would always tease about inviting us to women only events and how cute they thought we would look in their Dresses ! It helps that I was a runner in great shape so when I would say I doubt they would fit they would go on about having many I could try on ! After that for several days they would show of their dresses at work and talk about picturing me in it ! LOL

The times I usually took the girls up was usally part of dare and involved another boy. In junior High another boy and I were dared to wear dresses at a girls house as part of a truth or dare game. In the end we were talked into adding bras and pantyhose and modeling several dresses. The game was finally stopped when her mother arrived home with their Aunt and boy did they give us a hard time.

The other was when my male best friend at 10 dared us each to put on some of my sisters many Ballet tutus. We were dancing around being silly wearing the tutus and ballet slippers when we heard our cleaning lady howling in laughter. I was scared for a week she would tell my mother.


Anyway do you have fun memories of discussing with women/girls about wearing dresses even if you never actually did it ?
When I would dress then I would sometimes pretend it was their dress I was wearing with them their ! LOL