I didn’t think I’d ever summon up the courage to step into the lion’s den of body-beautiful Pines boys and strip down to (nearly) nothing—but that’s just what I did this past Friday night at the Fire Island Pines Underwear Party.

I didn’t even know that underwear parties existed until last year when, on a warm Friday night in Cherry Grove, as I waited for a friend to arrive on the next ferry, I took a walk from my share house to the Cozy Bar at The Tides, right near the Ice Palace. I was walking in the door and was stopped and told I’d have to check my clothes. I turned around and walked out. There was NO WAY I was going to sit at a bar in my skivvies. After a bottle of wine with my friend, however, we found ourselves curious about what was going on over at the Cozy Bar, so, off came the tightie whities and on went the 2xist—and a crew neck T-shirt for good measure. (I barely take my shirt off at the beach! Even though I’m only a 33 waist and know that I’m not fat, I am a former 41 waist, and that, my friends, is the secret to keeping a therapist in business.). My friend and I wound up having a great time (he came home with more money than he left with—and doesn’t remember how or why…), but when someone told us about an equally fun party in the Pines also going on last season, we adamantly shook our heads and vowed not to go. Wearing your underwear in public in Cherry Grove is one thing; in the Pines, it’s quite another.

Maybe it was the seductive marketing on the 2009 Pines website, maybe it was the fact that we had heard great things about the DJ spinning that night, or maybe it was just the challenge of trying to pass off my newest bargain, a $6 pair of Old Navy Boxer Briefs, as “cute,” but I don’t know what possessed a friend and I to journey through the meat rack, sans flashlight, at 11:30pm last week.

Draining the last of the courage that was left in our big red “road-soda” cups, we hiked up our shorts (realizing all-too-well that in a matter of moments they’d be un-hiked) and headed upstairs to the Pavilion.

When we got there, we wondered if we were in the right place. Everyone was standing around fully-clothed. “Phew,” I thought, “I guess they cancelled the underwear party.” And then I saw the clothes check at the other side of the bar, where a golden-browned, expertly groomed bartender with a waist the same size as someone who might enjoy visiting American Girl Place, will make you feel perfectly inadequate by taking your pants and stuffing them in a bag. All that for a mere $2! What a bargain!

But we’d braved the meat rack and weren’t about to quit now. So we checked our clothes, and our inhibitions (ok, fine, I kept my crew neck T-shirt on…) and started dancing.

The place filled up fairly quickly – by 1am, the music was really going with a string of popular mixes characteristic of dancing gay boys (“Let Me Think About It” by Ida Corr, for example, and a Whitney Houston tune for good measure), and everyone was having a really great time, myself included.

A couple of guys came up to me and pulled my shirt off and I actually surprised myself by not putting it back on! The atmosphere felt comfortable enough for me to leave it off. The guys even bought me a drink or six to congratulate me!

Now, one characteristic of the Pines Underwear Party (a.k.a. “Flash Me Fridays”) is that if you flash the bartender or a cocktail waiter, you get one free shot or a pair of new underwear. When I saw the boy next to me do it, and what he had to offer the bartender (that thing was so shriveled that I mistook it for Estelle Getty), I asked myself what I had to lose, and by 3am, I had procured for myself two tequila shots and a pair of glittery Ginch Gonch boxer briefs (take that Old Navy! And Estelle Getty-boy!).

Overall, I must say that I was pleasantly surprised by the Pines Underwear Party: lots of cute guys, a very chill vibe, and surprisingly little attitude. The party itself (aside from the flashing, of course) was tame compared to the somewhat “raunchier” one in the Grove (I have yet to visit that one this season, but rest assured I’ll do a piece on it when I do). If you’re looking for a “back room” kind of environment, this isn’t the party for you. If you’re looking for a fun-filled evening on the relatively cheap (no cover, $2 clothes check, but expensive drinks…) with great music, then I would definitely recommend checking it out!