Chicago Love Story Ch. 02

Story Info
Josh gives his point of view as his feelings grow for Izzy.
5.4k words
4.17
8.1k
2

Part 2 of the 4 part series

Updated 09/22/2022
Created 07/12/2008
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Josh and Isabelle's story continues from Josh's point of view. Please leave me feedback!

"Daniels, I got that press release on that new band that'll be at Goose Island next week," my editor Matt barked over the cubicle. "It doesn't sound too promising, but at least go enjoy a brew, and then you could head over to the Cubby Bear or something."

"Hey, thanks, man," I said softly as he stood and handed it over the fake wall. "I'll check it out."

I felt lethargic again today. That had been my status quo for a time now. I suppose other people in the office noticed as well, but I didn't seem to care. I was up the shit creek without my paddle.

"Try not to be so enthusiastic about it, Josh, ok?" Matt laughed and leaned his chin against his fist. There were days I wanted to lean over, roll my sleeves up, and really give him a good punch. But I was a nice guy. At least, I used to be. "You've been moping around here for weeks now. What gives?"

I eyed him speculatively and returned my gaze to the computer screen. I didn't exactly feel like spouting my story to this particular jagoff.

"I'm still pissed I lost the office pool," I replied robotically. "Can't believe Tom Brady and the Pats let me down."

He laughed uproariously and sat down, still mumbling some incoherent nonsense about the Giants winning and the Superbowl being weeks ago, get over it already, and... ah, who gave a fuck anyway about Matt, the middle aged bastard with a comb over?

At last I had tapped a creative spark within and was feeling like Shakespeare himself until I heard footsteps coming towards my cube. I looked up and it was her. My heart quickened a little and I tried to not stare into her brown eyes, but I couldn't help it. It was Isabelle. And the truth is this: I miss her like crazy.

I felt her look right through me- her intense eyes reminding me of Lake Michigan in the midst of a wintry midnight. I felt as though she had taken my balls and slammed them between two giant slabs of ice, only the pain didn't resonate between my legs. Not even close. It was in my heart. The Isabelle who walked past me was a far cry from the one who had laughed and flirted at a Bears game, and not even close to the one whose kisses and caresses had made me feel as though I had died and was fucking an angel on a soft billowy cloud while harpists and choirs serenaded us. Yeah, the sex had been THAT phenomenal. My sweet, teasing friend Izzy wasn't even there anymore. This Isabelle was wicked. I can't really say I blame her.

I shuddered as tiny hairs on my neck stood up when she walked back again to her cube, making sure that I realized my presence was as pleasing as a sharp tack lodged inside of her boot. I tried to play it off. I knew my eyes would get the best, or rather, the worst of me, because although she seemed to loathe me, the mere sight of her in black slacks and a form fitting purple sweater made me pant inwardly. That's why I kept them downcast a lot when she was around. I didn't want her to witness my agony over her loss. And I thought Matt was a jagoff?

I recall the night not long ago when I had been in Peoria for that concert review. I just couldn't stop thinking about her- couldn't get her beautiful smile outta my head... her ten-thousand watt grin that made my heart flutter... Jesus, even seeing her approach me back then in the office made me stand up straight and act all gooey and shit. That was not me to be like that. I tried to chalk it up to lust. I had fucked her, and it was good. Maybe it had hurt a little when she seemed so damn tentative when I had asked her where we were going, like, five seconds, after we'd both cum. That was bad. I know. Bad and dumb. Isabelle had been my friend for years and we had found great joy in sex. Together. I couldn't help but be in complete awe of her afterward. I mean, I figured she didn't know where her head was. For years now, we'd been friends, and then I surprised her with flowers, and then a few days later, we had sex. I kinda did the chick thing by pressing her for an answer as to where we were headed. I had to save face somehow, right? Brush it off like no big deal- that it was sex and we could fuck around until something better came along. But what was inside my heart was something completely opposite. It was scary. It loomed over me like an enormous tidal wave. It was a warm and comforting feeling behind the devious waves from hell, but falling for someone meant a whole lot of other stuff that made me recoil in fear. It was safer to play it off and be noncommittal. I couldn't help myself, though. I called her, texted her, thought of her. It was hard to ignore the urge to be around her.

In any case, I had been in my hotel room downstate, thinking about her, wondering what she was doing back home, and when she didn't text me back, which had been our norm now, something told me all was not well.

"Look, I'll lay it out to you. I've been dreading this moment, Josh, but I know about you and Molly," Isabelle had said, her voice not echoing any sort of emotion over the phone. I called her first thing Saturday after I'd rolled in. She reminded me of someone on WGN news- emotionless and to the point. That wasn't Isabelle.

I felt myself deflate like a tire that had hit a giant nail. Leave it to Molly to let her jealousy get the better of her. But she was far, very far, from my thoughts at that point.

"Are you pissed at me now?" I asked, masking the worry and doubt that was stirring in my heart.

I heard her laugh nonchalantly. "Are you going to be pissed for someone I slept with six months ago? C'mon, Josh. That's dumb. If you had slept with her the night after we'd been together, then yes. But no, I'm not pissed."

"Well, I know how some women would be."

"I'm not some women."

As she said that, I got that feeling that goes through me when I'm playing darts and then I hit the target. Isabelle definitely wasn't just some woman.

"So, I'm gonna just throw this out to you, ok? If you're still trying to get in her pants, then lose my number. I don't need to be played by you, Josh. Especially by someone who was my friend, and more importantly, someone I work with. I've had enough heartache from guys to last two lifetimes. Give me a rest from that, please. Don't take this any further if this is just a big game to you."

She was taking that commanding tone with me- the one I heard when she was giving orders in a meeting. I couldn't help but feel slightly intimidated by her. She was one of the sweetest women I know, but also one who didn't take shit from anyone. I could only imagine what kind of opinion she had about Molly now.

"Ok," I said, trying to sound confident. OK? That's all I could muster to reply to her? Again, that deflated feeling returned.

We had agreed to keep seeing each other, though I was confident when I hung up the phone that she'd wanted nothing to do with me. That next day at work had been damn right scary for me, but as I had leaned back up after grabbing my diet coke from the pop machine in the lunch area, she was standing there with her dollar and a shy grin on her face. I remember exactly what she had been wearing: a soft white flowy top, gray slacks, and a black cardigan sweater. Her dark brown hair fell in her eyes, and as she brushed it away, I saw that shimmer that I couldn't quite describe. It made my heart bounce.

"Hey you," she said as she smiled sweetly at me.

I gave her one of my cocky grins. No need to play too easy into her hand. It was still okay to have a little chase.

"What's goin' on?" I asked nonchalantly as I walked by, lightly caressing her back with my knuckles. I inwardly breathed a sigh of relief. She didn't hate me after all! All was not lost!

Molly had been a different scenario altogether. She had played it very cool with me at the office, but as I stepped onto the El that night for my journey home, my phone rang.

"You're pissed I told Izzy, aren't you," she said rather than asked. "That's why you wouldn't even look at me today. I know it Josh."

My heart twinged a little, and I'm not sure why. Hell, I can't even begin to explain what I felt for Molly. She had intrigued me back then. I suppose initially I saw in her what no one else in the world could, or even would, see in her. Everyone else saw an emotional wreck and damaged goods, but I had seen a potentially beautiful woman who needed saved. What an idiot I'd been.

She had been so kind to me in the beginning. No one else really seemed to give a shit about the new music writer, but she'd shown me around and had made me feel good about myself in a world that was totally new to me. I guess it was one of those attractions like a patient forms for his or her doctor. I felt that way for Molly. It didn't help matters that I was attracted to older women. She'd been the star of many a late night fantasy that helped me reach my solo explosion. On top of it all, she ate up my attention like it was her job. I guess in a way, she made me feel needed- that someone actually gave a shit and wanted my support and opinion. But my affections? Not even close. My attempts to sleep with her had failed. Except for that one night. I know her self-esteem was non-existent. Her asshole boyfriend had called her late to bitch her out for not being home, even though he knew full well she was still in the city at our Christmas party. She had cried and collapsed into my arms. It hadn't taken much to get her to open up to me. In more ways than one. Did I regret sleeping with her? No. But it was sort of the means to the end for me. I was tired of playing her game, tired of her getting her dose of warm fuzzies from me only to go home to Joe. It wasn't fair to do that to me, and finally I was seeing what Izzy had described to me this past fall. Ironic, huh?

Another sick part in this sordid love tale is the fact that I had taken my early frustrations to Isabelle, who would always listen kindly and sympathetically. I knew she had gone through some big things with guys and had gotten hurt by this ass she'd been engaged to. Izzy being Izzy, the kindhearted, gentle natured one that she is, had been nice to Molly, and had even encouraged Molly to date me and dump the schmuck. That had been early on, and then Izzy began to see through her. It was then that Izzy had begun to tell her to back off and not hurt me. It had all fallen on Molly's deafened ears. Oh, she told me everything. She even suggested I date Izzy because I'm certain she interpreted Isabelle's concern for me as Izzy wanting me for herself, but knowing Molly, I knew she only half-heartedly suggested it. It would eat her alive if I had done it. And I know now that she was playing off the innocent one with this whole situation. She stirred up a lot of trouble for me. Lucky for me, Isabelle is rational.

"I see no reason why we can't all be friends," she said animatedly. "You're my friend, Josh. I'm not going to give that up. She doesn't have to act this way. She stormed out of my cube like I was the devil and I don't think that's necessary."

I half-heartedly listened as the issue of Izzy became a non-entity to her, and that was sad. I had seen Izzy be a kind friend to her when no one else had. I don't think Molly was being a good friend back to her. In any case, she pled stories about how she suspected her boyfriend Joe was cheating on her with some woman he'd met in a chat room because she had looked in his email blah blah blah and her mother was driving her insane yada yada yada. She was waiting for me to make her feel good about herself again, maybe even suggest we hook up only for her to turn me down. I just wasn't feeling it. Just then, my phone beeped.

"Hey, hold that thought, I got another call," I'd said. A smile spread across my face when I saw Isabelle's name come up on caller ID.

I excitedly said hi and managed to get Molly off the phone with the empty promise I'd call her back later.

"Saturday night you're coming with me to watch my friend's band perform," she said confidently. I could melt at the sound of her voice.

"Oh yeah?" I replied. I couldn't hide the smile in my tone. "Sounds like that's an order."

"Neither one of us has enough fun in our lives," she stated.

"You wanna have some fun, huh?"

And fun we did have that night. If I close my eyes, I can still see her in her sexy black wrap-around skirt that came slightly above her knees. With it she had paired a soft, light blue tight fitting sweater that accentuated her amazing breasts. At her feet she wore high-heeled black boots that came up her calf. She had twisted her dark brown hair into a clip with tiny tendrils falling around her face. I'm sure I'd never seen her look so sexy, except for maybe when she'd been buck naked riding my cock like a crazy woman.

I don't think either of us was having much luck paying attention to her friend's band. We sat at a table with a group of her friends. I couldn't help but massage her thighs. Her panty hose felt so soft. My hand managed its way between her legs and I felt it hot and damp.

"Well, guys, seeing that I have to get up early tomorrow and go into work, I think Josh and I are gonna call it a night," she said hurriedly.

I grinned devilishly at her, and after what seemed like an excruciatingly long cab ride back to her place, I had her in my arms.

I held her tight, kissing her lightly on her lips as she slowly began to unbutton my black dress shirt.

"You were in quite a hurry to leave," I said to her between kisses. "Any particular reason why?"

"Mmmm," she moaned, her voice getting all soft and smooth, like she had just taken a long sip of silk. "I just wanted to come back here and get busy with this."

"Perfect plan," I murmured as I kissed her neck. I was amazed by how much that turned her on. The goose bumps appeared instantly.

"Yeah," she sighed as she put her arms around my shoulders and held me close.

I wrapped my arms around her waist and gently laid my head on her shoulder. She smelled of sweet vanilla. It soothed me while it turned me on. We stayed like this for a fleeting moment. She felt relaxed. I couldn't wait to have her.

I took her by the hand and led her back to the bedroom. Pixie the cat opened her eyes as we passed by her. She rolled over and went back to her snooze as though she fully knew what was next.

I undid the hair clip and watched her dark locks fall around her face- the sweet smell of her hair emanating through my nostrils. She finished unbuttoning my shirt and cast it aside. She reverently kissed my chest, my neck. I sighed her name, letting her push me back onto the bed as she sank to her knees.

I was the clay and she was the artist. With her hands and lips and tongue, she gave me the most amazing oral treat any guy could ask for. I felt her suck on my bulging cock head while a hand stroked my shaft. She licked my tool like I was her favorite flavor of Popsicle. I heard her moan a little. So sexy.

She stopped momentarily, but I knew she'd be back. I kept my eyes closed, imagining how soft and wet her pussy would feel when I could finally put my cock inside of her. I felt the soft caress of her tongue once again, and I managed to open my eyes to see her beautiful naked breasts. She rubbed the tip of my cock against her nipples. It was enough to nearly make me blow my load. I had to taste her.

I quickly got her out of her skirt and panty hose. To my delight, she had gone without underwear and I spread her legs to feast. The first night I had tasted her she was sweet and tangy, but tonight she was salty. I inhaled her musk and slid my tongue into her sweet box. My thumbs grazed her clit while I worked my tongue in and out. I heard her moan.

"Ohhh, Josh, yes," she whimpered, causing me to work her harder. At long last I put my tongue to her clit and licked it furiously. Two fingers found their way inside her pussy, and I fingered her while I suckled her engorged clit. My cock was hard and rigid.

She cried out, moaning and whimpering, her noises like seductive music driving me fucking insane. I had to have her.

I kissed my way up her chest, pausing to reign kisses and nips at her belly button. Her tits were perky and alive and I couldn't help but nibble on them. But what was best was her waiting mouth, and I kissed her fully and with need.

"I...Oh, Izzy," I stammered between kisses. My lips seared across her face to her cheeks, her nose, her neck.

"What, sweetie?" she uttered, her hands engulfed in my hair. I felt her nails rake down my back and shoulders. I sensed her need as I slowly moved my hips. The tip of my cock touched her wetness, and it was no less of an excitement than being shocked by a live wire.

"I just want you so bad," I stammered. She made me feel so weak, so helpless. I wouldn't feel any better until I was inside of her.

"Then do us both a favor and fuck me," she whispered furiously, and then, seconds later, the gentle Isabelle returned. "Josh, please. Now."

I slowly slid in and I heard a distant cry of relief from not just my voice, but hers.

"You feel amazing, baby," she whispered in my ear as I worked in and out of her. I dimly heard her voice. I could only feel, touch, and taste her. In the dim light glowing from the tiny living room of her apartment, I saw her expression of true delight, and it made my heart swell. These foreign feelings would've scared me shitless if I hadn't been so deep into her.

I felt her wrap her legs around me tightly, and I complied to her need to feel close. I needed to feel close, as well. I sank down to her and put my arms around her as I buried my head between her gorgeous breasts. I kissed them languidly, still moving in and out of her, savoring the slippery warm feel around my cock.

"I can't seem to get enough of you, Izzy," I whispered. "You feel so fucking good, baby."

"Mmmm, yes," she moaned. "You do, too."

I felt her squeeze me furiously with her pussy muscles, and I couldn't help but let my eyes roll back into my head. I felt that celestial feeling again, as though it were an angel who was sending tight shockwaves from my cock to my heart. She continued her torture and before long, I could feel myself gearing up for the moment of eruption.

I gazed down at her, our eyes meeting when suddenly both of our voices cried out. She clung tightly to me, her pussy like a vise grip on my cock, while I flung my head back and then down again, her brown eyes shining into mine like the sun.

"Oh God, Josh, yes!"

"Izzy! Ugh, you're amazing! Yes baby!"

I heard her moan and cry out again as I brought her not just one, but two giant orgasms. I felt my cock explode into a zillion tiny shards inside of her. She gripped me once again and I reared my head back in glory.

It was done.

Our breathing ragged, I kissed her furiously, like I didn't know what else to do with myself except stay connected with her.

She looked up into my eyes and her own joyful contentedness was evident. She smiled at me, her face glowing in the dimness. She trembled in my arms as I pulled out of her and held her close. I was speechless. Never before had I experienced sex in the past like I'd just had with Isabelle.

"Is... Is that the first... time you've ever come like that?"

I only shook my head, not able to find my voice. My head swam and my heart fluttered at a strange cadence.

"Pretty amazing, isn't it?" she whispered as she kissed my lips gently.

I could only hold her and caress her hair as she fell asleep in my arms. I couldn't relax, couldn't calm down. The connection I had felt with her- it was as though I could read her mind and I could feel what she felt. I felt as though something in my heart had given way to something huge- like a dam had broken or something like that. I tensed as she curled herself into me. I began to feel panicky, sweat prickling at my forehead. It felt almost too comfortable and I felt the urge to push her off of me. No, I couldn't. But I did.

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