FICTION: Hipster Girl

Update your links to here, as this is now where the story lives.  Eros Monthly went down, and I’m republishing the story on my site as of now.

PDF

I kept just missing her in the coffee shop. She was a short, anger-edged Wicker Park hipster with apple-red dyed hair cut in a bob, a little silver stud on her left nostril, and freckles. She always looked up and smiled, already throwing things into her backpack and on the way out the door. The other day I managed to brush her shoulder in the doorway as she was heading out and I was heading in. She almost stopped. But she just said “Sorry,” surreptitiously and bolted for the train station. Yesterday though, I caught her.

I’d only seen her three times in two weeks, but it was enough for me to make Filter my regular coffee shop. Filter’s one of the last holdouts for Chicago smokers. They roast their own coffee in the back and grill panini at twice the recommended temperature as a half-hearted attempt to conceal the smell in a tobacco-free town.

I suppose if I said something to the management they’d stop everyone from smoking for as long as I was there, but I wasn’t going to rain on anyone’s parade. Even I had to concede that it’s part of the atmosphere of the place. Literally.

Yesterday was one of those perfect, sunny, late spring days, the kind that lends itself to daydreaming. I started thinking about the girl in the coffee shop and decided I’d actually try to meet her. The worst that could happen would be I miss her, in which case I’d spend the afternoon out in the sun. I left the office a couple of hours early and caught the train to Damen.

As luck would have it, when I walked in she was there, crouched over a green covered edge-worn paperback, her painted fingernails poised just so on a the handle of a coffee mug. I stopped momentarily, trying to read the title of the book, and she looked up and smiled. That was why I could pick her out of a crowd – that smile. I didn’t even order coffee before putting my bag down at her table.

“Hi, I’m Josh. Sorry to split your table, but it’s really full in here. Can I refill your coffee while I’m up?”

“Sure,” she said, her smile more of a quizzical smirk. It didn’t break into wide grin until her face was already buried back in the book. The book was open to the same page when I came back with the coffee.

“Thanks. I’m Lori, by the way. Just taking a quick break, actually, so I can talk for a bit. Been meaning to say hi to you next time I saw you.”

“You work here?”

“Mmm-hmm. People-watching. I’m a fashion designer. I’m actually based over in Lincoln Park, but don’t tell anyone here that. They’d never buy anything from me again.” She sipped her coffee. I don’t remember exactly what we talked about. I’m never good at remembering conversations, but we sat and talked for hours. Her book sat on the table, unread, and my coffee got cold twice. Finally the conversation hit a lull, and I seized the opportunity.

“I don’t know off the top of my head what’s going on tonight, but I’d love to keep hanging out with you.”

“I’ve got to work later tonight. We’re rolling out a new campaign tomorrow.”

“So what about tomorrow night? The State Street theatres have a couple of good shows on right now. Wicked and that Monty Python thing.” I was desperately rattling off a dozen half-cocked plans for dinner and a movie or a show, anything. Chicago’s good that way — plenty to do at a moment’s notice.

Lori bit her lower lip before she spoke. The barest flash of white, and I imagined two things: what I hoped she was about to say and the feel of those teeth baring down on my shoulder, leaving marks I might feel for days. Those marks I’d be embarrassed and half-proud to expose in the locker room in front of all the straight-laced family men who’d forgotten what it was like to have a woman that passionate about you.

“You know, Josh, I’d love to say I want to get to know you better, go out to dinner, have a cup of coffee, whatever. And I do want to – I want all that. You’re really cool. But you’ve been sitting here across from me for two hours driving me absolutely insane with lust, and I just want to take you home right now and fuck you until you can’t think anymore.”

Nothing could have prepared me for that, but I managed to hang on to the mood. I threw the book back into the bag, and made a show of zipping it up. She insisted on walking out behind me. I let her. We caught the bus east, and she slid down next to me and put a hand on my thigh. Every bump the bus hit and her fingers got a little closer to my cock. So subtle and so obvious at the same time. Just the perfect tease.

I stared at her fingers and traced them with my eyes, imagining it was my tongue. My jeans strained when she crept an inch up my thigh, sending electricity up my spine and in the verge of moaning with delight right there on a bus crammed with people.

When the bus stopped at Halsted, she grabbed me, right there in public. I felt like the entire bus was watching me, but no one was. It’s a big city, and you’re one of millions. But that didn’t stop me from feeling embarrassed, imagining myself the center of attention. I turned all shades of red and kissed her to stifle a groan before we stood up. When I got up, I adjusted my backpack to conceal my hard-on. Lori, on the other hand, was practically giggling over how worked up I was.

She led me up to her apartment, and I nearly stumbled half a dozen times trying to catch a glimpse up her skirt as walked the two flights of stairs to her apartment.

“Come on in. Don’t bother with the couch or the barstools. I want you in the bedroom. Now. I’ll be right behind you,” Later I would be impressed by how spacious the apartment was; in that moment I was arrested by the force voiced in every syllable in that order.

I sat down on her pillow-top king and tried to gather my wits in the scarce seconds before she came in. Turns out that wasn’t enough time.

“I know I’ve sounded single-minded up to this point, but I’m actually nervous as hell… I’m giving you two options. I’m perfectly willing to do what you were probably been thinking about all the way along North Avenue: doggie style, missionary, on the couch, on the floor, on my kitchen table, whatever. But what I really want,” she said, as she opened her bedside drawer, “is to fuck you in the ass with this until your brain stops working. Like I said, your choice, but just so you know what I want.”

She held up a g-string harness with a little metal O-ring and a cock that looked, for lack of a better description (my brain was totally numb), just like mine. My heart jumped. I felt a felt warm, tingly sensation in my ass as I contemplated a fantasy I never knew I had. And now it was about to be fulfilled by a woman who’d been moored in my fantasies since I first saw her sitting in the window at Filter. I had to concentrate, and thought I might come at the mere thought of it. She looked momentarily at the door, clearly worried that she’d gone too far.

“Put it on first and I’ll let you know. . .I want to see it on you.” She smiled then, and proceeded to remove her panties from under her skirt without revealing a thing to me. She tossed them on the bed, and the string, still warm from her hips, fell on my hand. Every hair on my arm stood on end. She put the harness on the same way and then fingered the – no, her — cock. “Is this the one you want? I have more. . .”

She held it up to her lips like she was about to kiss it,while her eyes traced every ridge and vein of the skin. She turned around before taking off her skirt. The black lines of the harness went straight up her ass and to either side, tracing the lines of her cheeks. I tried my best to hold the image in my mind, so I would remember it in my dreams.

And then she turned around. She almost looked self-conscious, but then she saw my smile. I glided off the bed and down onto my knees and took her cock into my mouth.

I’ve never gone down on a guy before, and I may never, but she had charisma. I put my hands around the back of her thighs and I could feel her shaking ever so slightly. I stroked her thighs. I sucked her cock. I know there weren’t any nerves in that piece of silicone, but I could still feel her react to me. She moaned blissfully. Later she said that the sight of me going down on her and my fingers gently raking her thighs sent her completely over the top.

We ended up tangled on the bed, kissing, grabbing each other’s cock, peeling off our clothes. I felt her bite down on my shoulder, not so hard as to break the skin, but oh could I feel it, and was it exactly like I’d imagined. I leaned into it, moaning, digging my fingers into her back, kissing her throat because it was what I could reach with my mouth. Her skin felt wonderful under my tongue…

And then, just like that, she was on top of me, and I was face down on the bed. I thought of Lori’s slender breasts sitting high and proud like the cock she wore, closed my eyes, and waited. I don’t know what I expected, exactly, but the first thing I got was a single well-lubed finger, and that alone nearly sent me through the roof. I’d never had anyone else touch me there before, not once, no matter how much I’d wanted it. Somehow it never seemed okay to ask, but now here she was touching me because she wanted to.

One finger, in once and then out. I leaned back, trying to hold her in me for a second longer. Even now I can’t describe the feeling, except to say that everything tightened. Two fingers. My balls pulled up into my body like I was going to come, and she slid around inside me.

She moved on to a small vibrating dildo. I felt a chill run up and down my back and a burning, urgent kind of pleasure that had me reaching for my cock and stroking. I could feel the effect of the vibratior all the way up in my nipples. I think she sensed that I was too close to the edge, because she only left it on for a few seconds before turning the vibrator off. But she continued to fuck me with it, gently, getting me ready for her cock.

She was slow about it at first, I know, but it sure didn’t feel that way. Still, I could feel myself spreading for her, under her, and my whole body tingled. Just when I thought she had to be almost all the way in, there was a gentle, pleasurable “pop,” I suddenly realized that it was the head of her cock, she was barely inside me, just to the end of the shaft.

She took her time, and over what felt like minutes, she buried her shaft in me. The feeling was something like pain, though never quite agonizing, and yet something so far beyond pleasure that I can’t even describe it. Ecstasy, maybe. I know it’s overused, but it works: religious, speaking in tongues style ecstasy, complete with a chorus of Lori-shaped angels singing at the top of their lungs. Finally I felt her thighs against my ass. It felt so good, I found myself actually pushing against her, trying to get more of her. She ground her thighs against me in response.

But sex needs motion, and Lori’s grinding eventually gave way to thrusts. At first she was slow and gentle, and I reveled in feeling my entire body full of Lori. Then she thrust harder, and I could hear her thighs slapping against my ass. I felt closer and closer to coming. The cool air caressed my cock with each thrust, and I settled into the rhythm. I imagined I could feel her thighs in my ears, and it felt like her cock was splitting my ass in two. Yet there was nothing in the world that would have made me stop her.

I pounded back, hurling myself against her, and she started screaming with her thrusts. God knows, at that point we didn’t care if anyone heard us. She dug into me with her fingernails, and finally I came. I came, but her cock was so far inside me, putting so much pressure on me that I couldn’t ejaculate, and I just heaved back and forth against her, coming and coming. I screamed at her, “I’m coming, oh my god I’m… still … coming!”

The spasms began to subside, but still she didn’t stop. She kept driving into me. I felt myself get back into the rhythm, just thrusting against her, remembering my orgasm and wanting so badly to come again with her cock in me. I could feel her sweat dripping onto my back, and it cooled me briefly.

Then it was building again. “Lori, I’m going to come again … Please! Don’t stop,” I silently begged. She kept going. I started to come, and as I was screaming into the pillow she pulled out and grabbed hold of my cock. I came everywhere, and when I’d expended every onto the sheets, she flopped on the bed, pulled off the harness, grabbed me and started kissing me madly.

She pushed on my shoulders until my kisses were trailing down her torso. I circled her right breast with featherlike kisses and she pushed me further down. Her thighs tasted of sex. She was slick an inch down with her own juices, and I took pleasure in tasting every drop around where her tendons stood out against her slender, firm thighs. She pulled her legs up, and held me against her groin.

She was already so close, and I knew it. I darted back and forth between her labia, massaging them with long, deep strokes of my tongue. I darted inside her pussy and around her clit, above, below, left, right. Everywhere but on the clit itself. When my tongue grazed her clitoris just once, ever so lightly, she heaved against me.

I kept going other places, back and forth, and she kept holding my head tighter and tighter until finally she cried out, “Now, please NOW! Don’t stop,” she said, just as I thought had thought earlier. She came, and as my tongue probed every inch of her vulva, she bucked against me until I thought she was going to take my head off. Her excitement was so intense, I was close to coming again myself.

When her orgasm subsided, I crawled up the bed, shaking, and put my arms around her. Eventually her breathing slowed. The smile on her face was something to behold. At last she lifted her head and said, “Hey Josh, I do still have to work this evening. About tomorrow night. You mentioned some kind of theatre, movie, opera, dinner thing?”

“Yeah,” I said, feeling myself grinning right along with her. “I’d love to. Anything. You name it, I’ll be there.”

---

Possibly related posts: (automatically generated)

• Leno interviews for a summer job