Truth or Dare is great for all sorts of sissies, since it gives every level of girl a choice. Locked up sissies can explore their feminine drive and ambition, while outgoing sissies can try to be a bit more daring. Which one you are is up to you!
Swimming suits are often one of the first true girl clothes that sissies with like-aged siblings wear. Clothes are very interchangeable until puberty - except swimming suits. Girls often have onepiece swimming suits, which are a far cry from the loose boxer shorts boys get. And young sissies often end up wearing them at least once - either because they're curious, or their sisters force them.
But have you really worn one, sissy? How did you feel? Swaddled in femininity. Pretending to be a pretty beach bimbo? Or just a cute girl lounging on the beach?
Feel the wet, tightened fabric cling to your curves. Enjoy the feeling of your stiff nipples in the cups of the suit. Embrace the femininity of gracefully swimming in something that no man would ever wear. And of course, when you get out you can watch the water stream down the crotch of the suit - something that never happens in baggy, gross man shorts.
It doesn't have to be a long swim. It doesn't even have to be at a populated area (in fact, sissies out to swim on deserted beaches would probably benefit now as well). I also heartily insist that you lounge in your beautiful swimming suit, drying off in the sun. But that's not explicitly part of the dare - just something you should try, sissy.
For most sissies now would be an apt time to buy a suit, and then June will be an excellent time to test out the suit (possibly working your way into fitting into it, if you're a bit too afraid to try and buy one in person).