Almost all Speedo/brief swimsuit fans go through that process, starting with wearing them under shorts, dropping the shorts and realizing its OK, then enjoying the freedom of wearing what you like.
Another common thread is when one guy shows up in brief swimwear at a pool, causing 2 or 3 others who've been hanging around in shorts to suddenly work up the courage to join in, and it's now a Speedo fiesta.
Sometimes shy guys log in here and ask where "Speedo Friendly" beaches or pools can be found. The answer is that all it takes is one guy to break the ice.
I predict your problem will be when GF decides to flirt with you while you're hanging around the pool in your bikini bottom, just to see if she can get a rise out of you. And you'll find a need to roll over and sun your back, or else have to grab a towel quickly.
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