nAUGHTy Girl Chronicles. Vol 7.
Diary entries of a Black girl navigating love, lust, and the aughts in D.C.
October 2008
[Song playing from cars on the streets of Chicago]
Dear Diary,
I can hardly believe it. I left DC to volunteer at Obama HQ in Chicago for 10 weeks to elect the first Black president of the United States! Eek! I’m so blessed to be here and, let me just say: Chicago has really blessed me with all these fine ass men walking around!
I’ve got a funny little tale to tell about one such fine ass Chitown boo named Shawn. Tall, mocha brown, funny man I met through my friend who lives on the Southside. She invited me to her work happy hour, and when I ended up talking to her boss, he made me laugh so hard that at the same time I took a sip of my drink, I snorted it through my nose. Not a sexy move, but an authentic one. He asked me out on a date, and I obliged. He introduced me to old-fashioneds, explained why sophisticated people order steak medium-rare, and told me he was going through a divorce, even though he was still wearing his wedding ring. Suspect, for sure. But whatever, I’m in Chicago for a good time, not a long time.
Fast forward a few weeks, and the man has been coming on strong. Calls every day, texts every night, and makes me feel like I’m starring in my own grown and sexy rom-com. When we’re out together, he opens doors, orders for me, says all the right things at all the right moments. For once, I thought this one might actually be different. Chicago men might be built better than those dusty D.C. dudes.
Then came the night that changed all that.
Shawn said he wanted to take me somewhere special. “Somewhere just for us,” he said. His tone was smooth, low, promising.
The anticipation inspired an outfit costing more than my rent: a silky low-cut Black dress, suede high heels with an ankle bow by a designer whose name I can’t pronounce, perfume that naughtily whispers “fuck me”, and a lace underwear set for the gods.
He picked me up in his luxury vehicle, looking as fine as ever. Confident, cologne drawing me closer in, smile doing overtime. We drove away from downtown, the lights thinning out, the streets getting quieter. I asked where we were going. He just grinned and said, “You’ll see.”
And oh, I saw.
We pulled into a motel. Not a boutique hotel. Not a charming little inn. A motel. One of those places with a flickering neon sign where the “Vacancy” light hums louder than your intuition.
My heart dropped to my knees. I thought he was stopping for directions or to make a call, but then he parked. And turned off the car.
I wanted to say something. I should’ve said something. But then he reached over, took my hand, and smiled that same smooth smile from when I first met him, the one that had me thinking maybe I’d finally found a grown man who got it.
Inside, the room was a time capsule from the 1980s. Red velvet curtains. Cigarette burns on the carpet. A mirror on the ceiling that has probably seen too much. And then, the pièce de résistance, a heart-shaped bed with satin sheets and a coin slot on the nightstand.
He opened a twist-top bottle of cheap champagne and put some money in the slot to make the bed start humming like a clothes dryer.
I sat on the edge, trying to keep a straight face while thinking about what had led me to this vibrating monument of bad judgment.
Shawn, unbothered, started unbuttoning his shirt, grinning like a man in a music video no one asked for. I’ll admit, it was working. For a hot minute. Until he unzipped his pants.
Red.
Thong.
Underwear.
I blinked. Blinked again. Because surely, this was a joke. Surely, he was doing performance art. But no. He was standing there, like this was the big romantic gesture he’d been hyping up all week.
“Do you like it?” he asked, flexing his dick in the thong just a little bit.
All I could do was take another long sip of that bad champagne.
I was too stunned, too deep into curiosity, and too entertained to exit stage left.
We ended up making all sorts of kinky decisions on that ridiculous red bed.
A beautiful Chitown Black man with charm, intellect, and Obama-era swag with a proclivity for thongs and pay-by-the-hour motels. Isn’t life grand?