Workplace Romance - Chicago Ch. 01

When I stepped onto the plane, I thought about the flight ahead and the trip my company had asked me to take at the last minute. They'd called just yesterday and asked me to present at a leadership training conference in Chicago. The exec in charge of training couldn't make it and they asked me to fill in. I didn't mind being a presence for the firm, but presenting someone else's topic, was a bit unnerving. But we also had a corporate partner located in Chicago and I thought I could be productive for my role, and at least have dinner with my contact there and strengthen that relationship while in town. A week in another city wasn't in my plans, but I figured I'd try and make the best of it.

I found my seat, being upgraded to first class was a nice touch. As I settled into the window in the second row, a flight attendant was there immediately asking if I wanted a beverage before we took off. "Ice water and an orange juice" was my quick response, she smiled and spun around to retrieve my request.

It had only been a couple months since my last trip for the firm. What a trip that had been. I was asked to meet some of our firms newest members and steer them through a week of training as a member of the leadership team. But it was the corporate trainer that had made the week memorable. The week Michele and I shared had been incredible to say the least. Working by day, and having the most incredible, passionate, and inhibition free sex of our lives together at night. But it was more than just sex, we developed a special relationship during our short week, and I had found that I was a better husband and father at home, having gone through the week-long romance with Michele. An unplanned and unexpected, yet incredible development.

Since then, Michele and I had shared a few text messages back and forth for a couple weeks afterward, but conversation had dropped off a bit in the past month. We'd both actually felt better about going home to our families as if we were able to finally experience what our bodies had been longing for, we no longer held resentment towards our spouses for not being as intimate as we both needed. I had secretly wondered how long this feeling would last, how long would it be before we both felt the need to reunite again for more passion and play.

We talked about how her pregnancy was going, and how since our week she felt so confident in her looks and sexuality, even has her belly had continued to grow. She was looking forward to being a Mom, but worried that it would change her. Would she still be able to find that woman inside her again that she discovered when we were together? She was concerned she might lose the part of her that she'd discovered with me.

My daydreaming was cut short by the flight attendant returning with two glasses for me. The water and orange juice I had requested. She winked as she handed it to me quickly, "if there's anything else I can get you, please don't hesitate to ask, my name is Ava," and wow, she was striking looking. Possibly Swedish heritage as she seemed to be nearly 6ft tall, blonde, blue eyes, and full pouty lips, her uniform shirt concealed small breasts, but her uniform pants had a hard time concealing what was a perfectly heart shaped ass. It was large for her frame, and her pants strained to contain it. A perfect crease where her cheeks met the back of her thighs, made my cock throb for a moment as I got lost in what she'd look like when I peeled those pants off her. But, I just smiled as I watched it jiggle a little as she returned to the first class kitchen. She was very attractive, but trying to hit on her wasn't the plan, I had no intention of making it a habit to sleep with other women when I had to travel for business. It seemed as if my trip with Michele was becoming a once in a lifetime opportunity, never to be repeated again.

Looking out the window now, I eagerly sipped the orange juice as passengers continued to file onto the plane and fill seats. The sweetness of the sugar woke me up briefly as the last of the passengers boarded the plane. We backed away from the gate soon after, and were off to Chicago. I was just thankful it was June and not January. The weather would be enjoyable.

I opened my laptop and tried to work on the presentation I was expected to give. The first leg of the journey went by quickly, and before I knew it we touched down at DFW, a plane change was in order as I had about an hour layover before the connecting flight to Chicago.

As I stepped off the plane, Ava smiled "please enjoy the rest of your trip."

"Thank you for making this flight memorable, have a great day!" I responded. Re-thinking my previous thoughts, she was sexy as hell, and if given the opportunity, I might just be convinced to sleep with her.

Walking quickly through the terminal, I grabbed a sandwich, and headed for my gate. Eager to eat and finish off some notes on my presentation. I sat down and opened my laptop, grabbing the sandwich and starting to eat my lunch. I focused on my work, and tuned out the rest of the gate traffic.

I was successful at that until a figure slumped into the seat next to me and blurted out, "well hello there stranger!"

I recognized the voice first, but was still confused as I turned my head. How could this be possible? My mind immediately racing as our eyes met, a look of surprise on both of our faces.....it was Michele!

She looked as gorgeous as ever. Her blonde hair framed her face and hung down just past her shoulders. A white pin striped blouse fit tightly, over her perky breasts but loose over her pregnant belly, and a long flowing white skirt slipped all the way down her her ankles, she wore white strapped sandals on her feet.

"What are you doing here?" I practically exclaimed through the airport.

"Traveling for work, and I'm headed to Chicago for the week for a training conference!" She happily responded, "and I think we're on the same plane."

"Holy shit, stop. I'm going for the same conference! I'll be there all week!" I practically yelled again, hardly able to contain my excitement.

I stood up and turned toward her, bending over to give her a hug. She smelled fantastic, some type of fruity lotion as I remembered from before. And she was visibly much more pregnant than when we last saw each other. I must have been staring at her belly as I bent over for our embrace.

"This is my last trip before the baby is due, doctor's orders." She smiled wide, hardly containing her excitement to see me.

"We'll, this is about the nicest of nice surprises" I responded, "are you in Chicago the whole week too?"

"Yes, staying at the JW Marriott downtown." She said.

"Oh my God, so am I."

We both smirked at first, both turned into wide smiles as our eyes never broke contact with each other. I hoped she was thinking the same thing I was. Could this be an opportunity to reconnect again like we had before?

The thoughts racing through my mind almost made me stutter. I couldn't ask the question yet. It would be too fast, too presumptive, and given she was now eight months pregnant maybe not even possible. But I realized I didn't want to split up once we got on the plane.

"Where are you sitting?" I asked.

She fumbled for her boarding pass, showed me a coach seat near the back of the plane, Row 28. I snatched it from her and quickly made my way to the gate attendant. Thankfully there was an open seat in first class, and my plea to have the very pregnant colleague upgraded was successful. I returned with a first class boarding pass, for the seat right next to mine.

"This will be better, you know, given your current condition" I smirked.

She saw the 'Row 3, Seat D' on the pass and looked at me shocked, "you didn't...."

"I did", I beamed back at her.

"Now our conversation can continue all the way to Chicago" she responded with a wide smile of her own. "I've never flown first class before."

"Another first I'll introduce you to," I said coyly, referencing out last time together. A week of 'firsts' had been experienced, she smiled wide in agreement, and shifted in her seat. I felt my cock thicken in my pants, it was already responding even to the idea of being together with her.

We continued our conversation and seemingly moments later we were boarding the plane and settling into our first class cabin for the two and a half hour flight to Chicago. Row three was the last row of first class, right in front of the bulkhead, and Michele's seat was the window, and mine, the aisle seat next to her.

Michele was giddy with excitement when she was handed her drink before any other passengers even boarded. Her petite frame looked even smaller in the wide seats, and I could tell she appreciated the comfort of a chair that could recline more completely as she tested that feature almost immediately.

We continued talking, more quietly now, about how lives were better since the last time we saw each other in the sense that we both feel the incredible release of sexual tension had helped us focus on other aspects of our lives where that wasn't available.

"Is the sex any better at home?" I asked cautiously?

"He still doesn't touch me or even look at me since the pregnancy started." She responded, "he didn't even kiss when when I came from the last trip. Two days ago I caught him sneering and wrinkling his face up as I got out of the shower. He didn't think I saw him, but I did. It's heartbreaking, but I'm used to it."

"That's awful Michele," I started, "you're such a beautiful and sensual woman, with so much to offer, I still feel fortunate that we spent such a fantastic week together."

"See, this is why I missed you so much!" She exclaimed, and leaned over. Wrapping her arm around mine and leaning in to kiss my cheek. She lingered a little longer, I could hear and feel her inhaling deeply. And she whispered in my ear "I have masturbated every single day thinking about you for the past two months, I hope you won't disappoint me this week....." and settled back in her chair.

I turned to look at her straight on as the last few passengers slowly boarded oblivious to our conversation.

I whispered to her, "I'm glad you said something, I've been half hard since hugging you in the terminal. My cock has been throbbing in my suit pants for you...."

She smiled, and leaned back in, gazed down into my lap to see the faint outline of my throbbing member. The last passenger walked by, and her hand immediately dropped into my lap, she slid it over quickly to my shaft, and grasped it in her small hand.

She gave it a squeeze and moaned in my ear. "My pussy has been dripping for you since you hugged me as well, maybe these two need to be reintroduced to each other," she whispered back.

I pulled my head back and turned to look her in the eyes, "you're wet.....prove it" I stately flatly. Remembering our lunch together a few months ago when she'd removed her wet panties during lunch and handed them to me, which I kept the rest of the day.

She looked at me, and pulled her hand off my throbbing cock, a devilish grin crossed her lips. She looked around, I could tell she was nervous but excited, but after making sure the passengers in front of us, and across the aisle, weren't paying attention, she made a show of sliding her long skirt up around her hips exposing her beautiful, long legs. She reached around her large, round, pregnant belly and slipped her hand deep into her little white panties.

When she pulled her hand back out, two fingers were coated in her clear, slick, juices. She raised her hand quickly to my mouth and I eagerly sucked them deep. My tongue lapping at them and rolling over and between her fingers. She tasted just as sweet as I remember, fruity and fresh. I sucked on them until I knew every drop was gone.

She removed her fingers and quickly tossed her skirt back down as the flight attendant made her way back up the aisle and closed the curtains between our part of the cabin and coach. She was none the wiser. However, the passenger across the aisle did see something, a professional looking woman, probably mid forties with long dark hair and black squared off glasses saw her remove her fingers from my mouth and drop her skirt back down.

Michele noticed her and looked horrified for a moment. We'd been discovered! I looked over at the woman more directly after I saw Michele's face, just as Michele sat back in her window seat, trying to hide behind me.

The woman leaned across the aisle at me, and spoke in a hushed tone. "Good for you, my husband wouldn't touch me when I was pregnant, you keep that beautiful girl satisfied."

I smiled, a little shocked at her reaction, but happy she wasn't going to lose her mind and report what she'd seen, that could have been a problem.

I leaned back to Michele and whispered, "good news, you have a fan."

She peeked over, the woman smiled at her and gave her a 'thumbs up' sign with her hand.

Michele shrunk back into her seat again, clutched my arm tightly, and breathed a sigh of relief. Then giggled, I could feel her body against my arm as she hugged it. She laid her head against my shoulder and she squeezed me, I could feel the softness of her breast against my arm. Even through my suit jacket I noticed how much fuller it felt since I saw her last. I looked down at her, and her blouse had relaxed and was falling open, as I could see the beautiful soft mounds of the tops of her breasts, she was definitely larger than a few months ago. Her body, preparing to nurse after giving birth. They looked full, and swollen, heavier than they were before. Hints of veins just slightly visible emphasizing how swollen she was.

I slipped my left hand over our arms and with a couple fingers, gently stroked the side of her breast through her shirt and bra. She moaned softly at my touch.

"You're so beautiful Michele, and looks like you've changed a bit since I last saw you." I whispered.

She nearly purred back at me, "they're so much bigger and sore, but so sensitive too."

Then she lifted her lips to my ear, "last week I made myself cum just from caressing them." She paused, "I was imagining your strong hands and warm mouth playing with them, and I came so hard baby."

My cock thickened in my pants again, I could feel it stretching the fabric of my boxer briefs as is pulsated in its confines. Hearing her voice whisper those words to me was an incredible turn on.

Her lips were still against my ear, and I felt them open as if to say something again, she just moaned quietly and kissed the edge of my ear. Her tongue slipped out and caressed the ridge, up and down. As she did this, my hand opened and slid over her covered breast, rubbing and kneading it a little in my hand. I felt how full it was, and almost instantly, through her shirt and her bra, I felt her nipple engorge and harden in my palm.

She slipped a hand up to her blouse and unbuttoned two buttons as we began to taxi back from the gate. My hand pressed further over to her right breast underneath her blouse, I reached up and slipped her bra strap off her shoulder and tugged gently down on her bra, exposing her full breast to my touch. I could feel that nipple stiffen in my hand instantly. I could feel how much more swollen her breast was. As I touched her tender skin, I felt every ridge of her areola harden, and her eraser like nipples stiffened in my palm.

She moaned again and kissed my ear, my cock throbbed and lengthened in my pants, almost begging to be released immediately. My fingers caressed her nipples, bringing to pinch them gently between my knuckles, pulling gently on them as my strong hands caressed her swollen breasts. She squirmed in her seat.

The plane was taxing toward the runway, picking up taxi speed. I turned my head to look across the aisle. Our fan from a moment ago was watching casually, she didn't look away when we made eye contact. The passenger next to her looked asleep with his Bose noise canceling headphones on. She looked on, impossible to see specifics as I had been turned toward Michele, but she knew what was going on. She just smiled and nodded in silent encouragement.

Knowing the flight attendants would not be walking by until we'll after take off, I shifted my attention entirely to Michele again. I leaned in and kissed her lips, my hand still caressing her breast and now impossibly hard nipple. Our tongues danced in each other's mouths, we moaned in unison at the feeling of such passion again. She was such a good kisser. My lips left hers and moved to her neck, and lower to the tops of her exposed breasts. I slid her blouse further open and descended to her hard nipple. Still hard, and pink, slightly larger than they were just a few months ago. Her areola a little bigger, stretched to accommodate her larger breasts, her hard nipple a little longer and thicker than an eraser now, felt so stiff against my warm tongue as I sucked and licked her.

She squirmed and moaned softly, just loud enough so I could hear. She slid her right hand down to her skirt and began lifting it until her hand began caressing her pussy through her panties. Her left reached over the armrest and instantly found my throbbing flesh through my pants. I was now fully rock hard, and painfully angled in the confines of my underwear and pants. She squeezed and stroked slowly and I could feel precum pouring from the tip.

My mouth continued licking and sucking her right nipple, apparently she felt the other was jealous, and just as we reached the runway and began accelerating, she pulled her bra down on her left breast and held it up a bit encouraging me to move to the closer breast and I took it into my mouth willingly. Her soft skin tasted sweet as my mouth pulled on her erect flesh, stiffening further against my tongue like her other one had a moment ago.

She squeezed and stroked some more, and it was painfully hard at this point. In her little left hand my cock felt like granite and trapped in my tight underwear, desperately wanted to be released, much like she'd freed her breasts for me. Her right hand returned to rubbing her pussy through her panties as I licked and sucked her hard nipple in my warm mouth.

She moaned as I sucked harder, my left hand reached down, and pushed her fingers out of the way, and slipping inside her soaked little white panties. I paused for a moment, briefly rubbing her hard little clit before slipping through her slippery folds and plunging two fingers deep inside her wet pussy. She arched her back instantly, I sucked ever harder as she did, and a moan escaped her lips. I found her spongy little g spot instantly and applied a little pressure. She tensed her legs, shuddered, and I thought I felt a little squirt wash against my hand. As she shook, I tasted something sweet in my mouth suddenly, if only for a second. Her body began to relax and I slipped my fingers out of her and released her perfect nipple from my mouth. Her facial expression was priceless, pure bliss, mixed with lustful abandon, I knew that look, she wasn't finished.

The plane was now speeding down the runway, and my cock couldn't take the confined space it occupied anymore. Michele sensed this and quickly moved her hand to my fly, unzipping me, and pushing me back in my seat, with her other hand, pulled down my boxer briefs. She fished down my pant leg and grasped my pulsating flesh, with a little effort she pulled my impressive length out of the open fly. My rock hardness stood like a proud flagpole, thick and throbbing, at its full nine inches, every vein and ridge engorged. I watched a smile cross her face as Michele positioned herself in her seat to lean over me and take me into her mouth.

Fuck, the feeling was incredible. Her mouth was so wet, hot, and soft, and she slipped her lips over the enormous head. Bobbed back up for a moment, and then took me as far down as she could go, I felt the head press against her throat, and she pushed further rocking back and forth forcing my length down as far as she could, gagging just a little as she did.