Chicago Love Story

Story Info
She falls for her friend & winds up in a love triangle.
5.2k words
4.15
15.5k
6

Part 1 of the 4 part series

Updated 09/22/2022
Created 07/12/2008
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

This is the first istallment of Isabelle and Josh's story! Please leave me comments!

*

"We've got an extra ticket if you wanna go, Izzy," Josh told me shyly, his crystal blue eyes glimmering with something I hadn't seen before. "Just say the word."

"Are you freakin' kidding me?" I stammered excitedly. "You have tickets 4 rows from the field at a Bears game and you're asking if I want to go? Of course I want to go!"

I stood up from my desk and hugged my friend excitedly. He smiled at me with surprise and then cleared his throat. He had a deep, sometimes gruff voice that suited his teddy-bear like stature.

"Perfect," he said. "I'll give my buddy a call and let him know you're gonna take the ticket before he gives it away to douche bag Darryl."

I giggled and watched Josh walk back to his cubicle. I couldn't help but smile enthusiastically as I thought about attending a Bears game with my friend and colleague Josh Daniels.

Josh and I had been working at The Windy City magazine since he got hired three years ago. I had managed to work my way up the journalistic ladder to arts and entertainment editor when he was hired fresh out of college with a liberal arts degree. He had a passion for music and a knack for writing. No doubt he had been perfect for the job of writing reviews of local bands and musicians in and around Chicago.

I had gotten to know him better through my colleague and sometimes friend Molly, who was hated among the staff. Being the nice person that I am, I always tried to be kind to her when the rest of the world wasn't. That's me- Isabelle Wilson, the angel of The Windy City news office.

But anyway, back to Josh. He had formed a bizarre crush on Molly, and why, I had no clue. Not that I'm some sort of cover model, but really? Molly? (Not that I was particularly vying for Josh's attention, however, no one could figure out the connection.) She was shorter than me, but then, most women are being that I'm 5'8". She was a little chubby with blondish hair, blue eyes, and glasses. With some updated clothes and make-up, she could've been more attractive, but again, who was I? Definitely not the fashion style guru of Chicago. Trying to find the good in all, I thought her to be funny and we had frequented a few hot spots in the city watching some bands perform. She sounds like a pretty decent human being, right? Well, what turned the world off from her was her filter, or lack there of. She whined, told the world all the minute, redundant details of her life, and to top it off, she didn't do her job well. No one could understand why I continued to be nice to her, but I guess I'm that kind of girl.

Josh Daniels had formed a crush on her despite the fact that she was nearing forty- a whopping thirteen years his senior, had two children from her previous marriage, and was living in a small apartment in the suburbs with a jerk named Joe. What Josh saw in her, no one could really figure out. But, Molly ate up his attention like a glutton at a bonanza bar.

"If you don't like him, Molly, then let him go. Don't use him," I would say repeatedly when she would complain about his advances.

"I know, Izzy, but I really like him as a friend," she would whine. I cringed at that voice. "And not to mention, I love his attention."

"Sure, who doesn't love attention? But really, Molly, you're not being fair. You're giving him false hope when there's none to be had."

"He's just not my type, Izzy," she uttered once, completely oblivious to the fact that I was trying to meet a deadline. "I think he's more your type."

I didn't disagree, as I thought back to the conversation I'd had on more than one occasion with her. Josh IS a cute guy- he is tall and stocky with black hair and crystalline blue eyes surrounded by enviable black lashes. His smile lights up a room and his sense of humor always sends me into gales of laughter. He and I had formed a tight bond that Molly claimed didn't bother her. She even insisted that I could "have" him. I scoffed. Yeah, like she owned him.

I watched him from my desk as he sauntered back to his cubicle. He sat at his desk and caught my eye which he met with a smile and a wink. My heart skipped a little, and it completely surprised me. I shook my head and tried not to think about him in that way. C'mon Izzy! This is Josh! He's got a thing for Molly!

"Hey, Izzy, you got plans for Sunday?" It was none other than my friend and mentor Lynn, who was one of the top editors of the magazine. Yes, she was one of my bosses, but she was like a mother figure to me, as well.

"Um, actually, I'm going to a Bears game," I said. I saw her face light up and then she asked the question I was dreading. Lynn had been dying to see a match between Josh and myself for the past year or so.

"This is it!" she said excitedly, though discreetly. "He's finally giving up on Molly!"

"SHH!" I hushed. "Just stop. You have this crazy idea that Josh and I should be an item, and I just like him as a friend." A friend, I reiterated in my head. Just a friend. Friend, friend, friend....

Josh arrived at my apartment around 9:30 the Sunday of the game. We were going to tailgate with a bunch of his buddies before kick-off. He rang the bell, and I buzzed him in. He stood at my door with his cell phone in hand.

"Uh huh." (silence) "Yeah." (more silence)

I rolled my eyes as I threw my Brian Urlacher jersey on top of a white sweatshirt. It was starting to get chilly and I knew, with the breeze blowing in off of Lake Michigan, it would get cold at Soldier Field.

At last he hung up, and I didn't have to guess with whom he'd been talking.

"Still letting her call, I see," I uttered sardonically. "Joe must be outta the house, huh? It is, after all, Sunday morning. Or, wait, did he even come home?"

He tried to hide his embarrassment, though not well. He plopped down on my couch and petted my cat, Pixie.

"I can't be mean, Izzy," he said. "I don't ever call her anymore- she's the one who calls me."

"Then all you have to do is not answer," I told him. "Josh, look. I'm telling you this as a friend." I sat down next to him and heard Pixie purr. "I think you're a great guy, and you deserve better than what she can offer you. I care about you. I don't want to see you get hurt."

He looked at me, his eyes filled again with something I couldn't name. He nodded and a moment of comfortable silence passed between us. I stood and broke the spell, and together we headed for Soldier Field.

The game was amazing, but chilly. I felt Josh's arm sneak around me.

"You're cold, aren't you?"

I nodded, my teeth chattering.

"Shoulda worn something warmer," he whispered as he squeezed my shoulders and laughed.

I stood to go to the bathroom at half time, totally unbeknownst to the conversation Josh and his two buddies were having about me.

Mike raised his eyebrow ruefully and spoke.

"Jesus, Daniels, when were you going to tell us about the gorgeous brunette you were working with?"

"She's got amazing tits, man," Sam slurred after his fifth cup of beer. "I think Van Morrison wrote the song Brown Eyed Girl about her."

"You're crazy not to try and hook it up with her, dude," Mike told him. "C'mon, she's hot and she's older than you, but not as old as that other chick. Dude, I know you like the older ladies, but seriously. You don't make a move on her, you're an idiot."

Josh smiled and laughed with his buddies, thinking about Izzy and what his friends were saying about her. Deep down he felt a connection with her, but he was afraid to let her know. She was five years older and wiser than him, attractive and smart, outgoing and friendly. He definitely felt a strong physical attraction to her, without a doubt. But there was Molly... and as hard as he tried to put her from his mind...

"Hey guys, did I miss much?" She returned refreshed and smiling, and what she didn't know was that Josh couldn't help but notice how cute she looked in her prided Brian Urlacher jersey and her hair pulled back in a pony tail. He saw her, truly saw her, this time, and felt himself harden. No doubt he had imagined before what it would be like to fuck her, and he wondered if she shaved her pussy or not, but there she was and it was like he was seeing her for the first time.

"Are you going to sit there like a dufus or what?" I giggled as I sat and elbowed him. Why was he looking at me like I had a second head or something? "OK, before I freeze, put your arm back where it was. You're so freakin' hot."

The more beer I drank, the warmer I became. The Bears had victoriously won against our dreadful rivals, the Green Bay Packers, in an embarrassing 43-3 assault. I had been a die-hard Bears fan since I could remember and it's always a good day when Chicago beats the cheese heads.

"Take that, Favre! You SUCK!" I screamed as the Packers ran into their locker room.

"You do realize he can't hear you, right?" Josh laughed as we inched out of the crowded stadium. The fans were screaming and yelling in victory.

We managed to get onto the Blue line part of the El that was jam packed with fans. Being the gentleman that he was, he went with me back to my apartment in the West Loop area. He still lived in a suburb northwest of the city with his parents and would catch the Blue line again back home.

Awkwardly we stood in front of my building where I would soon warm up in my tiny one bedroom apartment.

"You're welcome to come up and hang for a bit if you'd like," I told him. "It's only 4:30."

"I need to head home, Izzy," he said, although every part of him wanted to be with her. These feelings for her were electrifying, and if Molly knew, she'd be horribly jealous, he thought.

"It's alright," I said, trying to hide my disappointment. We hugged sweetly and I watched him walk back to the El station where he'd venture back to his parents' house.

The months that followed seemed to pass by quickly. Thanksgiving came and went, and I barely remember our staff Holiday party. I admit I'd had a little too much to drink.

"C'mon, Izzy, just a little kiss," Chris Luna, another cutie we worked with uttered outside the room in the hotel we had chosen for our party. Chris was tall, with sandy brown hair, blue eyes, and a goatee and mustache. I found him to be absolutely adorable, and I complied to his request. It was innocent enough, but a few weeks later, I had no idea the exchange had been seen by none other than Josh himself.

"Getting a little friendly with Luna there, Miss Wilson?" he boomed into the phone one night when I had gotten back from work. Josh had winced at what he'd seen pass between Izzy and Chris Luna. What the hell did she see in the guy? He shook his head and tried to deny the sparks of jealousy that lingered in his heart. It wasn't that big of a deal, was it? He tried to tell himself it wasn't.

"Oh, get over it," I said. "Yeah, we kissed. No biggie. I'd fuck him."

Josh was taken aback and felt a stirring of jealousy in his heart again. Snap out of it, Daniels!

"So anyway, Josh, my birthday is Wednesday and I'm just wondering what you're going to get me?" I giggled, flirting a bit. "You know, I like roses. Pink ones, red one ones. All colors. Just a little hint."

"Well, you know, I have a great idea to celebrate your birthday," he said casually. "I could take you out to dinner, we go to bed and take care of business tonight and first thing tomorrow. That way you're exiting 31 and entering 32 the right way."

I was shocked, but played along. We had joked enough about sex over the years that I didn't necessarily take him seriously. He was, after all, allegedly after Molly, but it was fine to flirt.

"Yeah, you wish, Josh," I said playfully.

"You think I'm joking?"

I was completely taken aback and the silence over the phone was deafening for a moment.

"Um, you're crazy. So, who's going to be in the play-offs? Now that the Bears are done for, I'm going for the Giants. Fuck Green Bay."

I changed the subject, but even after we'd hung up, I was thinking about what it would be like to make love to Josh. It was then and there, at that very moment, that I found it within myself to admit I had feelings for him.

It was a cold but sunny day. I shivered and asked myself once again why I loved Chicago so much, but the sight of the buildings and just the atmosphere of my sweet home was enough to remind me.

I was greeted by my colleagues with cards and hugs celebrating my birthday. I was welcoming thirty two with gusto. Thirty one had been a challenge as I'd broken up with my long term boyfriend and gained fifteen pounds. Thirty two was my coming out, so to speak. I had shed the weight and felt better than ever. I had a great career, a wonderful circle of family and friends, and I had my health. Deep down, the one thing missing was a partner, but I shrugged it away. It would happen eventually. Or so I had hoped.

When I returned to my desk after lunch, sitting there was a vase with a dozen multi-colored roses. No card was attached and I was completely flabbergasted to think that someone had done this for me. My colleagues ooohed and ahhhed at their beauty. I was completely amazed. I stood, my brown eyes sparkling with joy as I bent to inhale their delightful scent. I closed my eyes, and as I stood back, I met gazes with Josh across the room. My eyes met his and he smiled a casual, handsome smile. It was then I knew: Josh had given me the roses. A light bulb flashed as I thought back to our previous conversation on the phone. I had teased him about getting me flowers.

The office was abuzz with the gossip: Josh Daniels had given Isabelle Wilson a dozen roses. Not once had Molly's named been mentioned, as it had been known that the two of them had a flirty rapport. I didn't even give her a second thought, as I was so taken aback by Josh's gesture. Luckily she was going to be out of the office till next Monday and for that I was grateful. The roses would be safely home and I hoped no one would tell her about it.

It was late, after most of the staff had gone home, and I was plugging away at my computer trying to meet a deadline. I stopped as I saw him inch into my cubicle. I smiled sweetly, almost shyly. This was a Josh I had never seen before. In the past, he was my buddy- the guy I'd joked with and gone to a fun Bears game with. Now, a new light was cast upon him. I bit my lower lip and said hi.

"So, like the roses, huh?" He said with a cocky, proud grin. He sat and smiled across from me, his eyes as blue as I'd ever seen them.

"They're beautiful," I sighed, admiring them happily. "I can't even tell you when it was the last time I got roses on my birthday."

"Just say the word and you can have them whenever you want," he replied, a longing appearing in his eyes. I didn't know what to say, how to look at him, so I looked away.

"So, some friends have decided to get together Saturday to hear a band and have some drinks," I said without a second thought. "You wanna join us?"

"Yeah," he grinned. "I'd like that a lot."

After a brief conversation, he stood and smiled, and I felt a warmth grow in my heart.

"Happy Birthday, Isabelle," he said, and I believe that was the first time he'd ever called me something besides Izzy.

My friends ended up having to cancel their plans, but Josh and I decided to get together anyway. It was an extended celebration of my birthday as we sipped cocktails and dined on Chinese food at a quaint little restaurant. We shivered all the way back to my apartment where we had decided to hang out and watch movies.

"I have to go to the bathroom," I said as I unzipped my boots. I walked past him as he stopped me and kissed my lips softly. I smiled, taken aback, but not at all disappointed.

I'm not exactly clear as to how it all began, but before I could even blink, he was kissing me as soon as I returned from the bathroom. I ran my hands through his hair and my brown eyes met his crystalline ones. Before I could say another word, we were lying on my couch and his warm hands felt their way up my black sweater. I smiled down at him sweetly as he cast my top aside to the floor. He kissed my chest and removed my bra.

"They're as beautiful as I imagined," he whispered in amazement as he licked and suckled upon my nipples. I giggled and he explored further, undoing my pants.

I felt my heart stir and my panties moisten. He kissed my navel and slipped his hands into my dampened feminine parts. I gasped and caressed his hand, squeezing his exploring fingers with my pussy muscles. He kissed my lips lightly and I sighed with amazement.

He led me to my bedroom where he quickly stripped me and pushed me down onto the bed. He kissed my thighs and sucked them. I flinched and he laughed ruefully. He slowly sunk to his knees and I felt him lick my slit before he gently parted my nether lips. He found my clit and began his delicious torture.

I can't begin to recall how many times he brought me to my pinnacle with his tongue and fingers. I clutched the sheets as I came again, moaning and whimpering as I saw stars burst before me. He tongued me slowly again, his assault sweet and tender. I ran my fingers across my nipples and looked down at him, our eyes meeting. The moment was beautiful. There is no purer gesture during sex when lovers' eyes meet. My breath caught in my throat momentarily. I came hard and lay panting. I pulled him up to me and he held me against his chest as I slowly fell back to Earth in his embrace. He kissed my forehead and then let me free. I slipped into a t-shirt and followed the light of my cozy living room. He sat at the corner of my couch sipping a beer. His expression was unreadable.

I snuggled into his embrace and he kissed the top of my head.

"A penny for your thoughts," I whispered. His blue eyes met mine briefly before they returned to the television. I felt him move my hair aside and his lips ever so gently touched my neck. I felt myself melt in his embrace.

Moments later he said "come on, let's go. Round two." In seconds, we were back in my bed, kissing each other passionately. I was swept away, and as we kissed, I alternated between caressing his face and running my hands through his thick dark hair. There was no question at that moment that we had true feelings for each other. I couldn't seem to get enough of him, and he of me.

I slowly undid his belt and found him long, thick and hard.

"You have too many clothes on," I whispered as I continued to caress his cock.

"Maybe I'm waiting for you to take them off," he replied softly.

In seconds, he was nude, and his body was mine to explore.

I inched my way down his body, stopping to nuzzle the patch of dark hair that grew on his strong, muscular chest. I heard his breath catch as I found him with my mouth, and I began my own glorious assault on his manhood.

I gripped the base of his cock while I slowly swirled my tongue around the head. He was so thick and warm. I licked his shaft up and down, pausing to suck the head in between licks. At long last I took him slowly into my mouth, inch by inch. Salty precum glistened at the tip and I enjoyed every last drop.

"God, Isabelle," he groaned, his hands encroaching themselves in my long dark hair. "You're amazing."

I looked up, sensing my own need and desire. My hand continued the motion that was as old as time, caressing him as we spoke.

"I need to feel you," I whispered.

Somehow, he was above me, and after sensibly placing a condom onto his more than ready member, he penetrated me deeply, and I pulled him near me, kissing his lips.

He smiled as he began to buck his hips wildly. I tried my hardest to hide my discomfort. I wasn't feeling wild and primitive. I wanted to go slow, to savor him.

"What's wrong?" He asked, worrying marring his handsome face.

12