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I'm a man who wants to have a semi relationship with a man while I play the part of the woman

Tagged as: Big Questions, Dating, Troubled relationships<< Previous question   Next question >>
Question - (16 February 2015) 2 Answers - (Newest, 18 February 2015)
A male United Kingdom age 30-35, anonymous writes:

About me: young, live in a tiny village in the uk, have been crossdressing on and off for 5 years now, have met up with men but always get tested regularly.

So since starting my industrial placement from uni last summer I've expanded my wardrobe to a neat little stash having purged it months prior to that which I now regret. Living alone and not having much to do I spent more and more time dressing up, exploring makeup and dating websites... I've also spent a lot of time on tumblr looking at blogs made by people like me so there is a lot of soft porn, stereotypical feminine roles, etc that I see.

The problem is I've always wanted to have a semi-relationship with a man where I play the woman. My aim is to feel like a female as best as possible. So when I meet I have anal sex but I've never really enjoyed it, not that it's painful it just doesn't make me organism (which it should I think). Anyway I've got the opportunity now to see a man who I met in boy mode in a cafe to see if we clicked and we do. Anyway he wants a regular person to eventually go bareback with I.e. Without a condom. I would really like to try this out but I know the risks associated with it.

Once I have sex with a man I don't have the urge to do it again for a number of weeks/months. I'm not sure if I should meet this man and eventually go bareback with him. To maybe help you very kind people, I consider myself straight as a guy and straight as a girl so maybe I'm overall bi, but I don't find men attractive it's just what's under the belt that interests me. What should I do, meet up? Purge my clothes for the last time or continue to dress without sex?

Thanks for all your help, and yes I know I'm strange!

View related questions: anal sex, condom, porn

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A female reader, So_Very_Confused United States +, writes (18 February 2015):

So_Very_Confused agony auntIs it even remotely possible that you are transgendered?

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A female reader, Tisha-1 United States +, writes (18 February 2015):

Tisha-1 agony auntYou don't really enjoy anal sex as a receiver so why are you continuing to have it? Under no circumstances should you go 'bareback' until both partners involved have been monogamous and been tested and found negative for HIV.

You don't find men attractive other than the genitals?

I think you need to get out of your small town and find a larger arena where you can explore your desires and limitations.

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