The Voyeur (Chicago #05)

There she is again. Right on time, just like clockwork. Tonight she's already dressed for bed, wearing a black tank top and some pink shorts. Lying on her bed, talking on the phone. It has to be the same guy she's been talking to every night. Or a girl, I guess. Maybe a boyfriend or girlfriend. They always call at the same time. I wonder if it's a long distance thing, since she hasn't had them over yet, as far as I've seen, anyway.

As usual, she's smiling and laughing a lot. Soon, she'll gradually start touching herself. Her hands running over her body through her clothes, rubbing and pinching her nipples through the shirt, sliding inside her shorts. If I'm lucky, they'll tell her to take it all off and I'll get to see her big, pillowy breasts unobstructed, imagining what it would feel like to squeeze them, play with them, and bury my face between them. Then I'll watch her bare pussy as she spreads her legs, rubbing with her right hand, her fingers sliding inside to fuck herself. Looking at her face, seeing the way her eyebrows furrow and her mouth gapes open, more and more as she gets close. I wish I could read lips. Or I guess while I'm wishing for things, I wish I had one of those long range listening devices that spies use. I wonder if they sell those in stores for casual perverts like me? What I wouldn't give to hear at least her end of the phone conversation. Her moans. I'm already hard just thinking about it.

Her bedroom window is at the perfect angle: directly across the street and just slightly down from mine. And once again, her curtains are wide open. I'm not sure if she's leaving them open deliberately, or if she just hasn't bothered to close them. Does she have any idea I can see her? That anyone else in the surrounding units of my building could easily see into her room as she lies on her bed playing like that? Is she letting me watch? Teasing me? She hasn't caught me yet, as far as I've been able to tell. It's possible she's just too wrapped up in the hot phone sex to notice, but I like to imagine she's putting on a private show just for me.

It's picking up now. She's still holding the phone to her ear with her left hand while the right brushes over her stomach lightly, playing with the hem of her tank top. Now her hand is sliding under the shirt and up, and she's cupping and squeezing her breasts, playing with her nipples. I wonder how specific her phone friend's instructions are. Are they telling her how to touch, or just where? I'm stroking now, standing at my window and watching her.

There goes the tank top. Fuck. I stroke faster as my eyes are drawn to her big tits, her light pink, barely visible areolas, and her darker pink nipples, pebbled hard as she pinches her fingers lightly around them. I bet they're super sensitive; she's always pretty gentle about touching herself there. Her eyes are closed now. She must be imagining whatever image or scenario they're painting for her as she touches herself. Reacting to their words. Her thighs are rubbing together a bit, her knees bent up. I wonder if her pussy is already clenching. God, I want to feel that. I want to feel how wet and tight she'd be around my fingers, around my cock, sliding all the way deep into her.

I wonder how much of my cock she could take. I had to smile the first time I saw her use her dildo. Not just because it's so hot that she has one, which it is. But I also couldn't help noticing that it's a fair bit smaller than I am. The only thing hotter than seeing the surprised, eye-widening look on a girl's face when she sees my cock for the first time, is the sound she makes when I'm pushing inside of her as far as she'll let me go. It turns me on so much to imagine her doing that.

Her shorts are coming off now. And panties, if she was wearing any underneath. Fuck, I'm getting close already. She's spreading her legs, touching herself all over her chest, her stomach, her thighs, taking her time to reach her pussy. Her eyes are closed, clearly getting lost in the fantasy with her partner. It would be so fucking hot to be there with her right now: holding my finger to my mouth, signaling her to be quiet. Taking the phone and putting it on speaker, dropping it on the bed beside her. Listening to her friend describing their fantasy and then acting it out for her. Listening to her moans, feeling her body reacting to my touch. Looking up and meeting her eyes, her face flushed with pleasure. Helping her to each orgasm as quietly as possible so her friend wouldn't suspect a thing. Oh fuck, I'm cumming! Shooting spurt after spurt, straight into the window. Mmmmm, fuck!

She's still barely even touching; they're taking it slow tonight. I'm still hard, still stroking, still thinking about being there in her apartment and gently nudging her thighs further apart as I crawl between them. Looking up at her while my tongue explores her pussy and massages her clit. Hearing her moans as she tells her friend how good it feels, letting them think she's talking about them and their words as she plays with herself.

Her fingers are picking up speed, her hips writhing slowly. I want to feel her grinding on my face like that as I eat her pussy and suck on her clit. Imagining her wetness on my face; her taste, her smell. Watching and feeling her getting close. Hearing her breathing heavier, moaning louder. Fuck, I'm getting close again, too. I'm going to cum when she does, thinking about how good it would feel knowing she was cumming for me. She's writhing more, her whole body in motion. Her spare hand is squeezing her breasts. Her back's arching. She's just about... there. Fuck, her whole body writhing out of control now, rocking on the bed as she cums, still rubbing her clit. Mmm, fuck! Cumming again! Stroking and then squeezing just below the head of my cock, feeling the pulsations as more streams of cum shoot against my window.

I want to feel how wet she is after that. I'd want to make her so wet, with my mouth and her own juices, until my big cock could just slip into her pussy. I want to feel the tightness as her swollen lips squeeze around me, pushing in deeper, lowering myself onto and into her. Seeing if she could take all 9 inches of my hard cock. Thrusting slowly, alternating shallow and deeper thrusts as her pussy adjusts to my size, squeezing around me. Mmm. I want to feel her hands on my chest, or around my back, her nails digging into my skin, her legs wrapped around my hips and squeezing.

She's still going, still rubbing. They're having her go for another orgasm. She usually goes for two or three, whether she's on the phone or just by herself. If she gets one of her toys out, it can be more. So far, I've just seen the dildo and a smaller vibrator. I wonder if there are any others in that drawer in her nightstand, or if she'd be open to using any others. She seems like the type of girl who would be down to try some different things. Fuck, all the possibilities rushing through my mind are keeping me hard, and making me stroke again.

She's getting up, rolling over, moving onto all fours. Her right hand is still between her legs, rubbing her clit. She's pulling a pillow to rest on while she touches herself with her ass up in the air. So hot. I want to squeeze her ass cheeks in both of my hands and give them a smack before sliding into her from behind. My cock would be so deep inside of her that way. I wonder how far she'd let me go, how hard she'd let me fuck her. It would feel so good to just let go and pound her pussy while she touched herself like that. I wonder if she's ever had her ass played with. I bet she'd like it. Rubbing my thumb on her asshole while I fuck her. Feeling her cum on my cock, squeezing around me. I bet that's what she's imagining with her friend. Probably a guy. Oh fuck, she's cumming again already. Her body rocking, toes curling. That's so hot.

I bet she'll go again. I wonder how many times I could make her cum on my cock like that. Feeling me so deep in her pussy, making her stretch around me, playing with her ass while she rubs her clit or holds her vibrator against it. I'd tell her to do that, wanting to feel the vibrations on my cock.

Fuck, there she goes again. Her orgasms are getting closer together. It seems like they come easier after the first one, and get more intense as she goes. She's really writhing now, her thighs shaking. Her roommate's room is dark - I bet she's home alone. She must be getting pretty loud with it now. God, I want to hear that.

Fuck, she's still not stopping. He's really pushing her. It must be a guy, wanting more of her pussy on his cock. I wonder if he'd really be able to hold on this long if he was fucking her, or if he could stay hard and keep going like I do.

It's tempting to think about planning a time to casually bump into her around the neighborhood. I'd try to flirt with her enough to catch her interest, and hopefully to find out whether she'd be open to another hookup, or if the thing with her phone sex friend is serious. I have to just go for it soon; I bet we'd have a lot of fun together if we tried.

She's cumming again. Number four. Fuck. I bet she'd make the fucking sexiest sounds cumming over and over on my cock like that. It would be so hot to see how far I could push her. To see how many times I could make her cum, fucking her hard and fast. Fucking through her orgasms to see how long I could extend them.

I think she's stopping. I wouldn't stop. I'd keep going, keep filling her with more and more of my cum until she was forcing me to stop, or to give her a break at least. Until she'd really had enough. I bet she could go at least a few more times before getting to that point, though.

She's lying back down now, on her back. Still naked, still talking to the guy, some light touching here and there: her breasts and chest, her stomach. I'll take the opportunity to go grab some paper towels, to clean up the mess on my window. Still watching as I clean, wanting to see what she'll do after she gets off the phone. After he's gone.

She's hanging up now. Getting up from the bed, pulling her panties back on. I can see them now: light pink and lacy. Then she puts back on the tank top and shorts before leaving the room. I'm guessing to go to the bathroom. I sit down at my desk, browsing on my computer for some porn while I wait, lightly stroking my still-hard cock, and trying to decide if I want to go for a third. I look for videos that'll make me think of her, taking my cock from behind like that.

When she comes back into the room, she looks like she's getting ready for bed. She comes to the window, finally closing the curtains. Probably just to block out the sun in the morning since she has an east-facing window; she doesn't seem overly concerned with privacy. One of these times, I should try to let her see me. I'm really curious to see what she would do. For some reason, I have a feeling she would like it and keep leaving the curtains open for me. Maybe she'd even start checking for me, too. Or I could be way off and she could call the police. I would be surprised if she did that after seeing my cock, though.

***

I finally saw the mystery guy (I was right) a couple nights later, dropping her off at home, right around the time I'd usually see them chatting. I didn't get too good of a look at him since he stayed in his car, but he seemed older. I'm also pretty sure I caught a glimmer of a ring on his finger when he put his hand higher on the steering wheel, after he leaned over to kiss her goodnight. That definitely adds an interesting twist to everything.

She was on the phone when she got up to her room. Still talking to him while he drove home, I guess. He must've told her to go right upstairs and make herself cum again because she got right to it, stripping off and jumping into bed. Fuck. My cock had already been semi-hard since I saw her getting home. Seeing her get naked so urgently like that finished the job.

I couldn't help wondering about what they might've done together while they were out. Where they might've gone. Did they stay in his car to hook up? Did he have her over at his place? Maybe the wife was out. This girl was definitely intriguing. Anyone with such a naughty streak was worth getting to know a little better.

***

I finally got a chance to try Thursday night. My roommate Josh asked if I wanted to go to the bar on the corner for some drinks. I checked for my exhibitionist friend in her window, but her room was dark, so I decided I may as well go out for a beer or two.

We walked into the bar, and there she was. I smiled to myself when I saw her, sitting alone at the bar, a textbook open in front of her, and what looked like orange juice in her glass. A screwdriver, I guessed.

It was too tempting. I couldn't resist going up to her. I told Josh I'd get our first round and headed over to the bar, feeling suddenly anxious. I stood a couple stools down from her, a comfortable distance, and waited for the bartender, who I now recognized as her roommate, to acknowledge me. I knew I shouldn't let myself stare, but she must've felt my eyes on her because she looked up from the book to glance over, briefly at first. Then I guess something about me caught her eye, because she looked back again, and I even got a slight smile.

"Are you really able to read in here? Or is that just a prop to keep guys away?" I flirted.

She smirked back at me. "Maybe a little of both."

"Oh yeah? How's that working so far?" I grinned.

She laughed a little. "Not so well, apparently."

"Sorry," I said, winking at her.

The roommate bartender made her way over then. "She's doing me a favor, sitting here to keep me company since it's a slow night, so I haven't had the heart to tell her to lose the book yet. Maybe you can help."

The two girls exchanged a look then that I couldn't really decipher. But I got the impression the roommate might be encouraging me to continue flirting. Maybe she doesn't approve of the older married boyfriend.

"I'll see what I can do," I answered.

"What can I get you to drink?" she asked.

"Can I get two pints of Sam Adams?"

"Coming right up."

Once the roommate was busy preparing the drinks, I turned back to the girl at the bar. I needed to know her name, at least. "I'm Chris, by the way. My roommate Josh and I just moved in around the corner," I said, gesturing over towards Josh, sitting at a table on his phone.

Her eyes brightened a bit when she heard we lived nearby. I was eager to see what her response would be.

"I'm Sam. Molly and I live right on the corner here, too," she answered, indicating her bartender roommate.

"Small world," I smiled.

She blushed, biting her lip in a vain attempt to suppress the reaction. "Are you in school?" she asked then, an obvious attempt to keep things casual.

"Yeah, we both go to DePaul. Josh is in the MBA program. I'm in my last year of undergrad, doing finance."

"I'm in my last year, too. Psychology," Sam smiled.

"That explains the prop," I said, nodding towards her book, guessing it was a psych textbook.

"Yeah," she laughed.

Molly set the beers on the bar in front of me then, and I got out my wallet to pay.

"Did you guys want to sit at the bar?" Molly offered, setting out some cardboard coasters for the drinks.

I thought about it for a moment, glancing back at Sam. Her phone dinged with a text just then. I wondered if it was him. It was just about chat time. I couldn't help smirking to myself as I watched her smile at the screen.

"I'm actually gonna go in a minute. I really have to finish this reading for class tomorrow," Sam announced, looking first to Molly.

The girls seemed to have a silent conversation, or argument, then. I knew Sam was likely making her excuses to go up and play, so I decided to help her off the hook. I wasn't worried about it, figuring I'd have another chance soon enough. "It's okay, it looks like Josh found us a table anyway," I said, turning back to Molly. "Thanks, though."

"Sure. Let me know if I can get you guys anything else," Molly replied, giving Sam a sideways glance as she got lost in her phone.

"Will do. It was nice meeting you both. I guess we'll probably see each other around," I said, taking the beers and turning to go.

"Yeah, I'm sure we will," Molly responded. "We're here quite a bit. You guys should stop in again soon."

Sam looked up from her phone to give Molly a look, then turned back to me.

"We definitely will," I answered, looking right at Sam and smirking.

She smiled, too. Then she took a last sip of her drink before getting up and packing her stuff up. "See you around, then."

I brought the beers over to join Josh at the table and sort of listened to him telling me something about an article he was reading on his phone while I watched Sam finish gathering her things to head out; her face glued to the phone as she kept texting. Of course, after that, I was completely distracted, wondering what they were texting about. What would he tell her to do tonight? Was she going to meet up with him again, or just rushing home for some phone sex? I started getting hard, picturing her in her room getting naked again. I wanted to watch.

I started taking bigger gulps of my beer, wanting to finish quickly and hurry back to my room to see the show. Josh didn't seem like he was in any rush to leave, so I had to make something up about an assignment for one of my classes that I'd forgotten about.

"But you should stay and hang out," I told him, smiling and nodding towards the bar when I noticed him looking over there. "Her name's Molly. She lives around the corner, too."

"Oh, yeah?" Josh asked, his interest clearly piqued.

"Go sit at the bar and keep her company," I suggested. "Seems like a slow night."

"Yeah, maybe I will for a bit," he agreed.

Then I was off the hook. I told Josh I'd see him at home later and headed out. From the street outside my building, I could see the light on in Sam's room, but that's about it. I smiled and felt my cock getting harder as I made my way upstairs, eager to get the full view.

Sure enough, Sam and her married guy were already well into it by the time I got to my viewing spot at the window. She'd stripped down to her panties, and she was touching herself inside of them, her fingers thrusting into her pussy hard and fast. If I had to guess, I'd say she probably already came once, now nice and wet for her fingers to slide right in. I undid the fly of my jeans and reached inside my underwear to pull my cock out, stroking and growing pretty rapidly. There was a new level of excitement as I watched her, now that she knew who I was. If she happened to see me watching, I wouldn't just be a random pervert anymore. Now I'd be the guy who flirted with her at the bar, who made her blush. I couldn't help wondering how she'd react, and kind of hoping to find out.

Sam's underwear came off before long. Then I saw her reaching for the middle drawer of her bedside table and my dick twitched in response, knowing that meant it was going to be a dildo night. Fuck. I watched as she held it up over her, turning on the vibrations. As she started sliding it along her slit, and slipping it into her pussy for a couple of slow strokes to get it wet, I glanced back and forth between the dildo and my cock for a closer comparison. The toy was probably about as thick as me, but definitely not as long. Watching Sam press it all the way inside of her got me close, knowing that meant she could probably handle a little more, maybe all of me. That thought was enough to bring me over the edge. Grunting and cursing, squeezing my hand around my shaft, I let go and started spurting against the window, imagining that I was shooting inside of her pussy.

Sam came quickly on the dildo, too. For the first one, she rubbed the vibrating head on her clit, her whole body squirming and then writhing on the bed. Then she started fucking herself with it, her legs raising up and back. She thrust the dildo hard and fast into her pussy and then she was cumming again, her back arching, legs squeezing around the toy as she pressed it deeper inside. She went for two more orgasms like that in quick succession; one seemed to roll right into the next. It was so hot to watch. I felt another stream of pre-cum leaking from the tip of my cock as I kept stroking. It looked like she was going to keep going. It turned me on so much to think about fucking her like that, seeing how many times she'd cum on my cock. Imagining how wet and tight her pussy must feel. By the time she reached number five, I was cumming again, more hot cum spraying onto the window.