I went to the beach with my fiancee and some friends this past weekend. It was the first time I've worn a bikini to the beach and I had a great time. I actually felt more comfortable in the bikini than I ever have in a pair of men's swim trunks.
There was an added bonus on this trip though.
One of the friends we were with saw me for the first time dressed like a girl. We aren't particularly close and don't normally talk outside of the group, but my other friends warned him ahead of time.
He came up to me while we were all hanging out and mentioned that he'd been warned and really thought nothing of it because crossdressing doesn't bother him in the least, but that once he actually saw me dressed as a girl it made him a bit uncomfortable because he never expected to find me attractive as a girl knowing I'm a guy.
He assured me he didn't mean for it to be awkward and just wanted to compliment me on how cute I looked.
The compliment was quite nice and made me blush a bit.