Mens High Heels

For the Mens club I am in I have had to dress up as a woman a couple of times in Plays. Do I have tell my?

fiance about this? My best friends wife who helped dress me says that my fiance should know that I look great in a dress and know how to walk in high heels and have worn bras and pantyhose. She say that it will certainly come up at some point so I should tell her ahead of time ? What would I say and when?

Public Comments

1. yeah tell her
2. LMAO...There is just no easy answer for this without trying to joke on it, so I'll say yes just tell her
3. Dude, unless you are harbouring sexual feelings for other men why wouldn't you tell her? The best laughs in life are the ones we have at our own expense. I have pictures of me dressed as a woman many times in life. Many insecure men would balk at this behavior. But what they don't realize is that I did it for a purpose, to raise money for people who needed help. I am proud of what I did and I get the biggest laugh out of it. She will admire for your confidence. Remember friends, confidence is sexy, insecurity is not. Yoda out
4. Go ahead and tell her. It's not like it makes you gay. Are you embarrassed? You are doing it for a play, not because you like to wear dresses. Just tell her and have fun with it.
5. You're a man Robert, stop letting this woman dress you up like a punk. That's why our society is so screwed up now, it starts innocently and then progresses into something else. This woman can't get another woman to play the part?
6. You don't have to do anything. Is there some reason you don't want to tell her? If you can't share something like this, do you really have the type of trust needed for your marriage?
7. I find it hard to believe that anyone of the age to have a fiancée, as in "almost married", would agonize over a men's club skit. However, consider - you state you have been cross-dressing with this acting troop "a couple of times". Couldn't you say, "no"? Don't you get better roles for participating? Ask yourself - "Why am I the one playing a woman? Did I choose this role?" This would not happen without your acquiescence and permission. You allowed it, Robert. You like it. In my opinion, this role should be a source of laughter and pride, unconsciously shared with friends and family. Only a person with serious hang-ups would think otherwise. Are you afraid of adverse reactions from friends and loved ones? Are they abnormally disturbed over trivial matter such as this? I think you have serious issues with HONESTY, your SEXUALITY and your ability to RELAX and have FUN. Do the girl a favor and move on. You really need counseling to understand why you are wrapped up so tight over these issues - it's indicative that your personality is such that you are fearful of being embarrassed, or of being chastised for showing your feelings. The very last thing in the world you (or she) need is to enter into a marriage where there is not full and open sharing, support and communication. If you do not have the guts to publically come out of the closet and deal with this, at least find the cojones to tell her you are not ready, and that a permanent break-up is the best. Without attribution - this question has 'gay' written all over it. You'll be a lot happier when you can live you life in freedom, without the fear of what others think. Good luck.
8. It's just a play tell her. she might want to pitch in and help.
9. she should know
10. If it's just for a play, I don't see why you would be keeping it from her. Crossdressing for a play or any other kind of acting is no big deal. A lot of men, including Eminem, have done it. You never know, she might be a big fan of you in drag.