Interesting question.....hmmmmmm

If I knew that she and I would be the only ones who knew about it, yeah, I probably would.  After all, it's just in fun, right?  Of course, it would depend on her having the items that would fit me.  lol  I guess if I could not wear hers, she'd have to go buy them in a size I could wear.

Swim

role play

i would love that..then i could be your bitch..

Hum

I would do just about anything that my partner wanted behind closed doors

Not if . . .

she pulled out a strap-on!! Otherwise, of course! Fun is fun.

I had a friend come over.  He dressed up as Snow White including: the dress, pettycoat, lace panties,  black wig, fake boobs, heels and lipstick.  He made such a pretty date.

Of couse the guy needs to feel safe to do this.  My friend did and he left with a smile on his face and pics to check out when he is alone.

Like macdaddy1944 said... If I know it's only between my woman and it, that's one thing, but if she's coming at me with a Dildo strapped on, that's quite another thing altogether!

DG
 

Ha Ha Ha....I've had that said to me.

If I believed that it was turning her on and not serving as a form of amusement at my expense, I think I would.

Interesting question!

would be a butt ugly woman..so getting into drag is just counterproductive ...Flat Out  :

No....