Drink & Draw

When I met Jen, the first thing I noticed was how beautiful she was. Straight brown hair that fell below her shoulders, a cute little nose, and sparkly hazel eyes. Tall, thin, with a nicely sized bust—though hard to tell exactly as she generally dressed modestly. As I learned, she was also fantastically sweet and kind. She attended a recurring art event that I helped to organize called Drink & Draw, and I liked that I got to see her every other month. I always made sure to spend most of my time at the events interacting with her group of friends so I could be closer to her. Early on, I had managed to work out that she was married. I was disappointed that it meant she certainly wouldn’t be interested in me. Still, I was magnetically attracted and couldn’t not spend as much time around her as possible. I just kept it friendly. Over the course of several years, I became friends with Jen and her group of friends. I would occasionally see them outside of the event, but not often. I also got into my own long-term relationship—as it happened, an open relationship. Then I learned that Jen and her husband planned to move out-of-state. That was it, then. Nothing could ever come of it. I couldn’t stop the ache to be with her, though. The last few meetings she attended, I spent more and more time just sitting with Jen. At the last meeting, I concocted a flimsy excuse to mention I was in an open relationship. At the end, she gave me a hug. I thrilled at the touch! My mind was swirling with thoughts as I exited the building. I wanted more! I waited outside the door until she came out, and hugged her again. This time, I drew her in close, so our bodies touched their full lengths. Involuntarily, I let out a small moan, which she might have heard. The hug seemed to stretch on and on . . . was this more than friendly now? And then it abruptly ended. Did it end because someone else had come out? And then she left. The last time I would see her. Except! One of our friends from Drink & Draw decided to hold a farewell party for Jen, and invited me! I took some pictures of her, trying to disguise them as general event photos, so I would have that to remember her by. We wound up on the back porch, where she was telling me something very sweet about enjoying our time at Drink & Draw while I just wanted to grab her and kiss her. Jen fiddled around with an old Polaroid camera, but couldn’t get it to work. Someone else came out to the porch and butted in to our conversation and just would not leave. I wondered by the way both Jen and I kept rolling our eyes about the intruder if maybe she wanted the same.  I gave her a ride home. Another long goodbye hug. A couple of days later, I got a message from Jen: “I’m on my own tonight and I don’t feel like packing. Meet me for happy hour?” We met up at the Chipp Inn, a quiet dive bar, after work and had a pleasant conversation as well as a PBR and a shot of Jim Beam. I had to keep it short, as I had to pick my parents up at the airport. I could linger in my bliss, however, as my phone pinged again and again with weather-delayed updates to their arrival time. As we finally left, outside there was another goodbye hug. This one definitely was going longer. I could feel Jen’s breath, fast and a little jagged, tickle my ear as she snuggled her head into my shoulder. Very slowly, she brought her head up. Our foreheads touched and slowly, slowly, she kept moving her head until we were staring into each other’s eyes. The moment hung like that as if time had stopped.   And suddenly we were deep in a kiss. Soft, hesitant to begin with, but threatening to overwhelm. A brief pause to look in each other’s eyes again, to silently ask, “Is this happening?” and, “Is this okay?” The answer to both was yes. Then the kissing escalated in intensity as the months and years of longing burst out in a flood. Unfortunately, it couldn’t last. I had to leave to pick up my parents at the airport. But I had three more chances to see Jen before she moved away from Chicago. The first time we went to a Cole’s, a popular hipster bar. The place was packed, but we managed to grab two stools at the bar. As we ordered our drinks, I put my hand on Jen’s thigh and started sliding it upwards. “Not in the bar,” she said, “I’m afraid someone will recognize me.” Oh, right. She’s married. With that in mind, I finished my drink quickly and encouraged Jen to do the same so I could drag her outside to find a shadowy nook. We eventually found a dark lot between neighborhood apartment buildings with a shipping container in it. I was able to pick Jen up and sit her on a ledge on the container, spreading her legs so I could rub deeply as we made out, and reach my hand up her top to fondle her breasts. We fumbled our way to another dive bar, where we giddily had some more drinks and talked, oblivious to the world, leaning in and staring at each other. We might have been the only people there besides the bartender, I don’t know. Predictably the lights came on to indicate closing time, and I walked Jen along a deserted Milwaukee Avenue, holding her hand. The second time was like a proper date. We went to see some bands play at my favorite dark, dank music club, the Empty Bottle. Jen and I had a real, deep conversation about our lives and learned more about each other. We talked about books, tattoos, how late in life we started drinking, future plans. We danced like crazy and got sweaty and tipsy. Outside the club, under the street lights on a busy street, I pulled her in for a kiss. The kisses became fiercer and I needed to feel her body, so I took her hand and led her around the corner where it was darker and we could make out and hump against the wall. Walking around, we stopped in at Innertown Pub. Later, walking back, under the darkness of a tree in front of cinderblock townhouses, I stopped her with a deep kiss and put my hand down the front of her jeans, briefly fingering her oh so wet pussy. The last time, we met at a quiet dive bar in Andersonville called Simon’s, near my place. The point this time, though, wasn’t about “where to go out” but “to quickly go home.” The second we were through the front door of my condo, I pushed her against the hallway wall and held her there with my body we passionately kissed and grinded. I lifted both her arms over her head and held them there with one hand grasping her two wrists, my other hand now roaming her body freely. We were alone, in private, for the first time. We could do anything.  Shortly, I led her to my couch and I sat so she could straddle my lap. As we continued to madly kiss, I slowly undid the buttons of her blouse. When I finished, she leaned back briefly so I could slip it off her shoulders and she looked into my eyes. I paused, frozen in place. Her gaze floored me. There was such a haze of lust in her eyes, a desperate need for more—more of this, closer faster harder. A need to be taken.  We moved to my bedroom. I climbed on top of her in bed, taking a second to look down at this beautiful vision under me. And also the jeans she was wearing, which I so wanted to take off of her. We resumed making out while I humped against her. She still had on her undershirt and bra, and I was burning to get my hands (and eyes) on her tits after years of imagining this. We flipped so I was lying on my back and she was straddling me. I lifted her shirt off her. I noticed in this particular moment that Jen had a dumbfounded look on her face, saying silently, “why are we stopping grinding for any reason, you don’t need to see my breasts, you need to fucking grind your hard cock against my pussy, it needs it now!” As much as I agreed, this was a mission: I had to have her tits out and free. I unclasped her bra and slid it up and for the first time got a proper look. They were perfect, soft, full, and rounded on the bottom with a ski-slope top. (36 B, I’ve learned.) I now had unfettered access to the hardened nipples I always wanted to pinch. As soon as I latched on, the most jaw-dropping part of the entire evening transpired. Jen, unable to contain herself, began rapidly bucking against me, out of control, for what must have been a full minute, until she climaxed and collapsed onto my chest.  We took a breath then, and I contemplated whether we were going to go further. There was a definite line that would be crossed in very short order. We decided, achingly, not to cross it. Jen quickly gathered her things and left. Jen moved shortly after. We’ve kept in touch over the years. She asked me to write this (she’s written her own version). I believe in a message she sent me a month or so after she left: “One day I’ll get to fuck you. I know it in my heart.”