Yes I would, it would be fun sharing each others clothes for sure.
Do you in the future want to marry this fellow and have children by him. ? How will the children feel when *Daddy* comes to school in high heels and a tight skirt,to pick them up. How embarrassing for the little tykes.
No. He weighs well above what I do and he is at least 6 inches taller. My clothes wouldn't fit him. Plus, I'd lose respect for him at using the word sissy instead of just cross dresser. It is demeaning both to him and me as a woman.
Lol if we are similar size and I get to use him lol
Lmao. My clothes are way too big for my boyfriend.