“So what do you think?”
We tossed our bags on the floor and fell onto the hotel bed. We had decided on a whim to call in sick to both of our families for Thanksgiving and make a road trip to Chicago instead. We had been together for less than a year, and we had spent countless hours telling each other about the things we liked, the places we loved, and where we would like to go together. Not wanting to wait any longer, a surprise road trip to Chicago seemed like the best idea.
“I think this is amazing,” I replied as I rolled over to look out our hotel window. Chicago was one of his favorite cities, and it was my first time visiting. The holiday buzz on the street gave the damp, grey evening an impossibly romantic look. He slipped his arm around my waist and kissed my neck. I rolled over to face him and threw a leg over him to pull him closer.
“Look at how beautiful it is outside!”
He laughed and said, “It’s raining.”
“It’s Chicago, we brought an umbrella.” I kissed him and rolled on top of him. I could feel him getting hard through his jeans, and he ran his hands down my ass and thighs as I straddled him playfully. “Let’s get some dinner first,” I said, teasing him with a view of my nipples.
As he reached to grab them, I pulled away and rolled off the bed. He readjusted in his pants, still hard, and said, “You know I’m going to be turned on the whole time.”
I raised an eyebrow at him and said, “Good. That’s exactly how I want you.”
He said he knew a place he wanted to take me, so after a ride on the L, we walked down South Wabash to Buddy Guy’s Legends. We had listened to Buddy Guy’s music together, along with all sorts of other blues artists as we had gotten to know each other over the last few months. The space was bigger than I thought it would be, and probably emptier than normal, given it was the day after Thanksgiving.
We grabbed seats at the bar and ordered drinks. I wish I could say that I remember the artist who was performing that night, but I don’t. What I do remember is how we couldn’t keep our hands off each other, and the bar was dark enough that he could sit his stool close behind mine and slip his hand under my sweater to tease my breasts while the music played.
I couldn’t help myself from rubbing my ass against his crotch, and I felt the warm throb of his dick getting hard against me. After a couple of beers, we looked over the menu and put in an order. The bartender let us know it would be a half hour or so, so we said we were going to step outside for a smoke.
It was still raining, a cold dribbly mist, so we walked around behind the building. The L tracks ran overhead, and we found a spot near a wall to stay dry. Before I could light a cigarette, he pulled me close and kissed me hard. I pressed into him and kissed him back, and I could feel him get fully erect in his pants.
A car drove down the alley, and we stepped apart a bit and laughed. I went to light that cigarette, and he unzipped his pants and pulled out his cock with a moan.
He leaned his back against the side of the building and said, “That feels better.” He was rock hard and glistening with precum.
I don’t usually like to tell this story, and here’s why. What happens next is I just bend over and start sucking his cock. We didn’t talk about it beforehand, I didn’t ask if that would be ok. We’ve both gotten better at communicating and even now, a decade later, we still like to give the other *enthusiastic* consent. But that night, his cock just looked so delicious, and I figured, if he *didn’t* want his cock sucked, he would have kept it in his pants.
And also, there’s certain things we like to believe about ourselves. Before that night, I probably would have assured you that no, I’m not the type of girl who would suck her boyfriend’s cock behind a bar. That’s just not me.
But the proof is in the pudding, and I went directly for his cock. It was still raining, we were still behind a dumpster (a theme in my stories, I’m noticing), and I’m pretty sure a delivery person saw us as they ran to their car.
I wrapped my lips around his cock and took him in my throat until I could feel his balls on my chin. He grabbed my hair and moaned, “Fuck yes,” and he thrust himself into my mouth. I held onto his thighs while he fucked my face.
I was so turned on, my pussy was aching to have his cock inside me. I stood up, unzipped my jeans, and turned around. I slid his cock inside me, and I pressed my ass against him, taking him all the way in.
He grabbed my hips and fucked me, and with only a few thrusts, I came hard enough to release a wave of wetness onto his cock. With my pussy throbbing against his dick, he kept fucking me while the train overhead obscured my screams.
“I want to cum in your mouth,” he said. I turned around, knelt down, and opened my mouth just in time to catch his cum. I swallowed, licked up the drips, and stood up.
We looked at each other, a little dazed. This was our first time fucking each other anywhere other than our apartment. He asked, “Did that really just happen?”
I laughed, “Yeah, I think so. And it was really hot.”
We went back inside the bar, and if this story didn’t already seem too good to be true, here’s another tidbit for you: As the bartender brought out our food, the musician on stage announced that Buddy Guy himself was in the house that night and wanted to play a few songs. So in our post coital glow, with fresh chicken wings and fries, we got to listen to an actual legend play that polka dot guitar in his own bar.
I promise, this is all the truth. For a story of firsts: our first holiday, first road trip, first outdoor sex, it seems a little over the top. How did we not get caught? How were we both so cool with everything, even without any prior discussion? Somehow, the stars aligned, and that night saw the moment two exhibitionists found each other. It was a great trip, and he was right all along: Chicago is a magical city.
Source: reddit.com/r/gonewildstories/comments/l1xj9b/when_you_know_youve_found_that_special_someone_mf