• Sex

The Undie Conundrum: Ditch The Boyfriend, Keep The Lingerie?

I only think about my underwear in the millisecond when I yank them out of my dresser drawer in the morning. (Thong or no? Is this going to ride up at the gym?) My bra never matches my out-of-season holiday panties or my cotton boy shorts with a French poodle printed on the butt saying, “Ooh la la!” But whenever I’m in a serious relationship, I give painstaking consideration to my unmentionables. I’ve gotten on a plane wearing an elaborate black-and-pink lace getup under a T-shirt and jeans to meet my boyfriend, and shown up at his doorstep wearing nothing underneath a dress.Recently, as I frantically dug through my underwear drawer before heading out for a date, I realized that most of the men I’ve slept with have seen me in the same chocolate-brown lace boy shorts. They were a gift from my first boyfriend, Rob, and I’ve had a penchant for the cheeky cut ever since. Even as I’ve swapped boyfriends, I’ve never gotten rid of the lingerie I’ve put on for them. Most items still look brand spanking new — it’s not like I’ve worn them longer than five minutes, anyway. But I wonder how guys would feel if they knew they weren’t the first to see me in a certain piece of lingerie? It certainly makes me squirm.

Rob wanted me to wear trashy, over-the-top items with strategic cutouts. I laughed and told him that if he wanted to buy me a bra that didn’t cover, well, anything, I’d wear it. My personal choice stays within the realm of girly, lacy underthings. I bought a tasteful black teddy to celebrate Valentine’s Day with him and then a few years later, I surprised my new boyfriend, Sam, with the same teddy in a hotel room in London. Sam is the jealous type, so I let him assume that I bought the lingerie especially for our trip.

As the years have gone by, I’ve ditched the sillier pieces — anything with too much pink, countless ribbons, or an abundance of ruffles gets thrown into the trash. But I still have the brown boy shorts, the black teddy and a few other standbys. That morning before my date, the old stuff stayed in the back of my drawer. I have newer things that are sleeker and less frothy, but still sexy. Not like it mattered to the new guy — he didn’t really care for gift-wrap. After he took one look at me in my skivvies, they were off in a flash.

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