I notice this is your first post azure so welcome to the board.
Where are you in the World to carry out this dare? It's winter here in the Northern Hemisphere so beach trips are out.
You've worn speedos, I hope you enjoyed the freedom of movement in and out of the water and the better tan lines.
Is the problem of wearing a really skimpy swim suit the dread of wearing something that brief or the fear of being seen in it by the public?
If it is a dread of wearing it then start wearing your speedos around the house and garden when no one's about, get your buddy to join you, get used to it together. If you've never worn a thong tuck in the rear of the speedos to resemble a thong and see how it feels. You may find you like the sensation of a swim thong. Get something half way between speedos and the "dick socks" and see how you react to that. See how you and you're buddy look in something brief but not desperate.
If it's about being seen in public then do some research, find a quiet beach away from town where you can have space between yourselves and the nearest people, you may find other guys in skimpy and minimal swimsuits there.
If you get an erection in a skimpy or minimal swim suit act like it is normal, don't put your hands over your crotch and start squealing like a girl, running down to the sea and taking a swim is ok, so is lying on your front until things calm down.
If your going to "practice" wearing something skimpy with your buddy you probably will get erections, just laugh it off, it doesn't mean anything.
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