I had been hooking up with this woman for about 9 months, on and off. We weren’t a match for a relationship, but really connected on the sexual side. We met at a party (a story for another time) and were going home together within 45 minutes of me introducing myself to her. It was just… in the air that night and we kept it up for quite a while by having movie nights where we’d watch something sexy together and then fuck on her couch a few times.

Anyway, I was out at a bar with a few friends one night in NE Portland. Usual Saturday night thing, beers and a shot or two, some laughs. I got a text from her asking me what I was up to. I replied that I was out with some friends and not far from her house, actually. I didnt think anything would happen- I was having fun already- and thought I’d tease her a little bit with my proximity.

Then, she texted me a photo.. of these strappy black heels that she said she’d always wanted to buy. My breath caught in my throat.You see, in one of our many sexy conversations over text or in person, she mentioned that while a novice at heels, she really wanted to get a pair that she could feel slutty in- and get fucked in an alleyway. Part of the fantasy was someone she trusted, just taking her in the dark up against a brick wall, with barely any words exchanged.I simply texted back, “Oh, you got them! Can’t wait to see them in person ;).”

She replied with just another photo. Her in the heels, sitting on the floor with my favorite extremely short black skirt on, thigh highs and not panties. Well, it seemed like now was the right time. I texted back- “24th and Alberta. 10 minutes.” I received a reply that simply said, “K”.I finished my beer and told my four friends that I wanted to run across the street real quick- “an out of town friend just happens to be across the street at the other bar, and I wanted to say hi.”

I flew out the door, hands in pockets, assuring myself that the photo and the anticipation had already made me hard, by wrapping my hand around my cock in my jeans. I walked quickly but not too quick, savoring the anticipation, excited not only for myself, but of that sense of fulfilling a fantasy for someone. I crossed the street, walked the two blocks and peaked around the corner to the alleyway and saw her silhouette. A little taller now with the heels, thin, I could make out that skirt in the dim street light and her very short hair.

I quickened my pace, walked right up to her and kissed her hard on the mouth and she returned it, her tongue deep in my own mouth in this anticipation. I immediately pulled up her skirt, felt that she was already wet and played with her pussy with my fingertips for a minute or so as we kept making out. My other hand undid my belt and dropped my jeans just enough for my hard cock to pop out into the cool breeze. I wasted no time thrusting it inside her (part of the fantasy) and started fucking her against the wall right there, the brick grinding into her back. We made out more as I fucked her as I whispered “don’t get too loud, or I’ll have to stop… someone may catch us.”

That made her moan louder so she got a firm hand across her mouth. I stopped a moment, spun her around and firmly but gently pushed her against the wall again. She wobbled on her heels (also a part she was looking forward to) and I fucked her from behind. One hand had to steady her on her hip and ass, the other alternated between pulling on her short hair (which got a squeal each time) to reaching around and rubbing her clit.

It didnt take long for me to build and build and to finally whisper/ grunt to her that I was about to come. She did exactly what I knew was going to happen next- she crouched a little unsteady on those high heels) in front of my cock and sucked me to completion as I came hard down her throat.As we settled just a bit and she smiled up at me, I held a hand out to her so she could stand up properly. I started to say something cute and joking but she merely smiled, put her finger to her mouth in a “shh” manner, turned, straightened her skirt and walked away.

I stood in the alley for a moment or two and then fixed myself up and walked back to the bar. I went to the bathroom to wash up a bit, grabbed a fresh beer at the bar and joined my four friends who were deep in some old story. They barely looked at me until one said, “see your friend?” “Yep”, I replied, as my phone buzzed.It was her.

“Have a good rest of your night and see you next week for movie night.”

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