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sit down with him and really talk about it. Don't freak out. Just. Talk about it. Why did he feel like he wanted to try to be a transvestite? Does he actually want to be one, or just play around? Ask him if he feels different from other guys, like he's not really a guy at all.Or he could just be screwin' around.
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Overwhelmingly, most transvestites are straight. He just likes to get his kicks this way. You're not going to be able to stop him doing this, if it is something he is into, so just ask yourself if this is something you can deal with and add to the 'kinks' in your bedroom repertoire. Just as you deserve a man whose sexuality you can be comfortable with, he deserves a women who embraces and is excited by his sexuality. Firstly, find out if this is you. If not, move on. If so, have fun! Many men enjoy this, but are just afraid to say so. Don't insult and belittle him about it - that will hurt him a lot. This could actually open your relationship up to the next level of communication and intimacy if you handle it well.
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Chances are, he has always been curious about crossdressing. This is not a bad thing! Explore it with him, sit down and have a loving, non-judgemental talk, and comfort him knowing that it is okay for him to express such a harmless quirk to you.Of course, if you do not agree, you will likely not be able to change it, so you will have to do some soul-searching and find out if a cross-dressing boyfriend is a deal-breaker.There is a huge difference between transgender and transvestite (or cross-dresser) - the latter is not the desire to permanently be the other gender, but to just do it sometimes for fun. Be open-minded and good luck!
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