Showin' Off in Chi-Town

I’ve always been a voyeur. I peek and I pry and I glimpse and I glance every chance I get, and I’ve been rewarded quite a few times. Naked breasts here, a panty-clad ass there. This story, though, is actually about the only time (to my knowledge) that I provided voyeur fodder for others.

I was driving around Lake Michigan thanks to a work trip. On my way through the Windy City I stopped to spend the night with a friend – a former flame, really. We were an item fresh out of college, had a falling out and had only recently repaired our relationship. She was in grad school, and student housing was in a high rise.

Now, first of all, I could never live in the heart of a big city because I’d spend all my time living vicariously through those in buildings across from me. One of Alice’s friends even had a telescope. I know, I know. Telescopes are cool and all and it doesn’t necessarily mean anything dirty. This one, though, was pointed at a lower floor. And you should’ve seen the dude blush when I asked him about it.

But I digress…My friend, let’s call her Alice, was lonely. That was unusual. She was also horny. That was typical. We went to a local bar, caught up on current events, got lit and then stumbled back to her shoebox of a home, which was on around the 20th floor. While she did have her own bathroom, the rest was one small space. Bed in one corner, desk across from that, you know the look.

Sunset when we went out, the blinds had been left open. We returned late, and Alice simply switched on the harsh overhead light and attacked me. Drunk, she wrapped her arms around my neck and her tongue filled my mouth in record time. Alice was never subtle when sex was the subject. Not that I ever complained. With her back to the window she paid no mind to the free looks those across the street might steal.

Now, Alice is prim and proper in public and a bit stuck-up, so I wasn’t sure she’d want to give her neighbors a show. But I was tanked and caught up in the moment, and I rationalized that maybe this had been a fantasy for her – a way to release the closet exhibitionist. So I simply rolled with the flow and said nothing. I stripped her sweater and bra off, revealing her small breasts, puffy nipples and flat tummy. She tore her own pants and undies off, mooning some of downtown Chicago with her pale ass in the process.

“God I’m so hot for you,” she exclaimed, her eyes sparkling and those cute freckles contrasting with her cheeks’ flush. “I want you to fuck me right now. Right now!” I was taken aback by her aggression and stood there while she pulled my khakis and boxers down. Alice’s personality did bend toward bossy, but normally she’d bluntly ask me to eat her – which I loved – before I could dick her. This time, she had no need or desire for me to get her hot and wet; she was already there in spades.

Leaning over, she put my erection deep in her mouth, sucking violently. I stared over her flawless back and out the window. With the overhead on I couldn’t see much, but I noticed lots of lights across the way, both through open windows and drawn shades. And I knew there were scores of darkened frames, too, though I couldn’t make them out much. I smiled, wondering how many people would be just like me – hiding in the blackness, cock in hand, praying that we didn’t suddenly pull the blinds. It turned me on to know that this pretty girl and my dick were the center of attention.

Alice gave great head and she was using her porn-star method on me; the one where she jerked my shaft from head to base with her tiny fist while her wet lips rode right behind her thumb and forefinger. Her hot mouth engulfed me, tongue whipping the tip of my prick, and I forgot all about who might be watching. She suddenly pulled away, but she kept my cock clenched – in a good way. “Come on! I want this in me now!”

Her bed was covered in coats and clothes and my duffel bag and assorted books and such. She dismissed it with a flick of her hand and desperately looked around, her eyes fixing on the desk chair. “Here!” She commanded, pulling the chair out and sitting me on it, her hands insistently pushing me onto the seat. With her back still to the window (and nearly against it), she stood astride me, grasped my hardness in her little hand and guided me through her hairy bush and to her wetness. Her dancing eyes locked on mine and I entered her soft home. She moaned happily, lips curling into a big smile. God she was soaking. The window ledge was right about at ass level, so everyone on our plane and a few stories above had a killer view as I stretched her pussy.

“Ooh, you were always so thick,” she groaned, using her legs to propel her up and down. “God I’ve missed this.”

And I had, too. We hadn’t screwed in months but we certainly rekindled our fire in a fucking heartbeat. I wrapped my arms around her slender shoulders.

“It sucks we have to be quiet, but you shush now, OK?” the schoolmarm in the bookish Alice reminded me, briefly putting a finger to my lips.

I took that as a challenge to make her cry out, and I pulled on her shoulders, driving my dick deep inside her and holding her squirming frame. She squealed in high-pitched surprise, then groaned with pleasure.

“Shush now,” I said with a grin. “We have to be quiet.” She shook her finger at me in reproach before kissing me hard, her hand in my thick dark hair. She began fucking me fast, biting her lip so hard it nearly bled. “Alice, let it out,” I said, my hands moving to her humping ass. “It’s OK, let me hear you.”

“I can’t,” she whined in a tortured whisper, still pumping her hips hard. “I don’t want my classmates to know what we’re doing in here.” This was six years ago, but I swear to god I remember that specifically. I nearly laughed out loud. She didn’t want her fellow students to hear us, but she didn’t notice (or didn’t care) that her fellow Chicagoans could easily see us. Prim and proper or a slut in disguise? Probably both. She was wonderful.

With breath catching in her throat, Alice squinched her eyes shut, threw her head back and neared climax. She came hard, grinding her groin on mine and burying me inside her pussy. Sated for a sole second, she hopped off and turned around so she was facing the window. Now the fun would be over, I figured. Once she faced downtown Chi-Town she’d freak. Wrong. She bent low at the waist, put her palms on the pane and bowed her head.

“Come on!” she hissed. “Do it hard!” That I did, grabbing her hips, spreading her soft-but-shapely ass cheeks apart and ramming back into her heat. With the booze desensitizing my dick, I lasted a long time, until she came again and her juices began to abate. “Hurry, hurry, hurry,” she chanted. The increased friction tightened her up and I shot my stuff while she reached over her shoulder and pulled my head into her upper back, muffling my moans.

I collapsed on the chair and she followed, putting her ass on my lap while still stroking my hair. She stared into space – literally, she was looking out the window – and cooed while my cock slowly softened between her glistening thighs.

“Wow,” I finally mustered as she giggled. “That was so awesome. I never knew you were such an exhibitionist.”

She froze, the implications dawning on her. “Oh my god!” She bolted upright, my come dripping with her juices down her legs, and reached for the blinds handle – which promptly came off in her hand. Instead of fixing it, she raced for the light and flicked it off, both of us giggling in the dark. “I didn’t even think about that,” she exclaimed.

Our eyes adjusting to the blackness, we could clearly see the buildings across from us. One darkened frame suddenly illuminated, and a middle-aged man stood in underwear and t-shirt, grinning wildly and giving us the thumbs up. Her good-girl image returning, Alice was horrified. At least she pretended to be. I was never quite sure if it wasn’t what she wanted all along.

“I absolutely cannot believe I just did that,” she claimed, one arm akimbo and the other covering her mouth. Her mouth, but not her perky upturned tits or damp pussy. She was simply stunning with the glow of Chicago back-lighting her fine features. Radiant.

“Oh you loved it,” I stated, poking her shoulder. “It turned you on. Admit it.”

“You were great,” she answered, giving me a peck on the lips before slinking past to the bathroom. “But I swear I didn’t know. Basically.” Basically? But then the restroom door was shut and I was cleaning clothes and whatnot off the bed-spread. The next morning we both woke late and in a hurry – and with wicked hangovers – and we didn’t say a thing about the previous night. And for some reason, we never discussed it again. But I think she knew exactly what she was doing. Basically.