I think you should wear dangle earrings. That are the best earrings for sissy boys. It are the most feminine earrings of all, so I think it will express your feelings the most.
If you want to look decent or sensitive, wear studs. If you want to look dangerous or sexy, wear hoop earrings.
Personally I like hoop earrings the most. Not for looking dangerous or sexy, but just because it feels great. But I don't wear 'men hoops'. My hoops are as big as the hoops that girls only wear (they are 3 inch tall). But I don't give a damn about it. I always wanted to wear this girly hoops, even when I was a kid. And now that I finally got the guts to have them in my ears, I'll wear them forever.
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gotta ask my previous gym manager, he always shows up in it and think he is forever 16
I'd love to see what outfit you'd be wearing and how'd be wearing your hair. Then, I could make a couple of suggestions. Formal event, daytime or going clubbing?
These are the sissiest earrings in my collection. You are welcome to borrow them:
https://i62.tinypic.com/e8q0wj.jpg
something large, blingy and girly…. like what harakiri posted :)
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Dangling or hoop
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