first gay date. outfit options?

T

t

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im a 19yr old male. just a bit of background to my question. about a month ago, i was playing truth or dare with friends. One girl dared me to dress in drag the rest of the night. I ended up doing it. at one point i was alone in a room with a guy i didnt know to well, and he kissed me. i was kinda stunned but he got a couple more kisses in. we herd people coming so we stoped. it was my first time with a guy kissing and all that. well a couple days i got a phone call from him. (first time talking to him since the kissing). he asked me out on a date. I said yes because im really curious. He mentioned that maybe i should wear some girls cloths again because i looked nice. i said ill think about it. he didnt mean all out drag just a couple items. One of the girls found out and wants to take me shopping she even offered to pay for things for me. im seriously considering dressing up a little. How far should i go with dressing up, and what type of cloths should i look at? and what about underwear?
 
Nice button down shirt is always awesome :). Maybe a scarf as well, structured jacket, fitted jeans, and suede pumas are amazing!
 
Comfortable jeans, Ralph Lauren plain t-shirt , Rod Lever sneaks and the leather jacket =)
 
Are you really gay? Or do u just want to go to make fun of him? Well idk hopefully ur not making fun of him and all even though wear girl clothes is a little weird.(no offense to anybody) I say wear like skinny jeans a nice fitted top with a scarf and like the other person said sued shoes. Wear like neon colors and all. Then put one of those running headbands around your head. Or if you are going for a nicer look go into Abercrombie and Fitch guy section and you should find something.
And undewear?? I don't see why that matters but i guess to look really dressed up and all wear a thong. But i suggest stick to ur normale pair of undewear or u will be evry uncomfy.
 
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