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What should I expect on a first date?

Tagged as: Dating, Friends, Gay relationships, Troubled relationships<< Previous question   Next question >>
Question - (26 December 2013) 5 Answers - (Newest, 27 December 2013)
A male United States age 30-35, anonymous writes:

I have been a closet crossdresser for a few years. Recently I had a pro do a makeover on me and was finally able to see myself able to pass with no problem. Now that I decided to go out into the world a friend of mine set me up on a blind date with some guy that she works with. As I have never dated any guy yet I was wondering if I could get some tips on what to do, what not to do and what to expect on my first date.

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A female reader, Honeypie United States + , writes (27 December 2013):

Honeypie agony auntThis is the "nerdy guys" first date, and she suggested you get "frisky"? I think that would be a really dumb idea. He agreed because you can pass for a woman, and my guess is he would LIKE to date women, so you are kind up a creek.

But I guess it's one of those things that only time will tell.

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A male reader, anonymous, writes (27 December 2013):

I am the OP. I should have mentioned in my original post that my blind date already knows that I am a male. My friend works with him and according to her he is a bit nerdy(in a good way)and has never been on a date before. She kind of put it to him that neither of us have been on a date before and it would be a good experience for both of us. She told him it was not like we were getting married or something like that. After she showed him a picture of me and he was assured that I do look female he said ok. However my friend disagrees with most of you on one subject. She said to play it by ear but if we hit it off in anyway and the mood seems to be right that I should get frisky with him in an oral sort of way.

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A female reader, Honeypie United States + , writes (27 December 2013):

Honeypie agony auntErr blasted no edit..

I meant the type I wouldn't expect more, nor would I let "more" happen.

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A male reader, M Proops United Kingdom +, writes (27 December 2013):

This guy should know before you meet that you're a cross dresser.Being a blind date first impression will be everything,you'll like what you see or not.I f you like what you see then it'll be getting to know his personality via conversation over a drink,meal etc assuming he likes what he sees.

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A female reader, Honeypie United States + , writes (27 December 2013):

Honeypie agony auntDoes the guy know you are a x-dresser?

If not, I think he should know, because no matter how much you LOOK like a girl or feel like one, physically you are NOT a girl.

It's be rather underhanded to go on a date without him knowing.

What should you expect? Good company, good food, good conversation. Since it's the first date, I would expect more, nor would I let "more" happen.

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