First Time Out In Public All Dressed Up

[Connie D50]

wow have fun and post some pictures

[ronny0]

I truly ENVY you and your opportunity to express yourself, wish I or WE could join your event.
Although too many guys dressed up might draw the wrong attention, and give the wrong message.

[Krisi]

I have done the Halloween dress up. My lovely wife and I came up with the story that she did my make up, clothes were rented and she made me practice in the heels for the last couple of weeks. You could also say the clothes and heels came from goodwill, even the wig. Your SO or a female friend did your make up. Be sure to complain about the heels and exclaim that you don't know why women wear them.

You can't say anything to anyone who doesn't ask. Most people will just make a mental observation of how well you pull off the "woman" thing and decide that this is not your first time dressing as a woman.

I have been on the other side of this as the observer.

[Taylor186]

You can't say anything to anyone who doesn't ask. Most people will just make a mental observation of how well you pull off the "woman" thing and decide that this is not your first time dressing as a woman.

Agreed. This has been my experience.

And if asked, excuses like, "my wife suggested/asked/forced me to" or "I lost a bet" or "someone else did my makeup" or "heels are hard to walk in" (after you've effortlessly worn them for hours) will be dismissed as an insincere dodge.

Shakespeare exposed this subterfuge with a simple statement in Hamlet 500 years ago: "The lady doth protest too much, methinks"

[Alexis00]

At a party once a woman soon-to-be-friend asked if I had on a bra. When I said yes, she asked, “Did you buy one?”

Any further protests that it was “just a costume” we’re met with her [probably correct] observation that no one buys a bra to wear once…..Blushing the color of an apple didn’t help!

[ronny0]

At a party once a woman soon-to-be-friend asked if I had on a bra. When I said yes, she asked, ?Did you buy one??

Friends like that are hard to come by, and need to be cherished. I had a neighbor woman that encouraged & supported my desire to dress, but she passed way too soon.
She did share her "hand-me-downs" and often would gift me her clearance rack finds that put a smile on my face. I really miss our friendship & connection.