Workplace Romance - Chicago Ch. 07

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Author's note to readers: Please be advised this is one chapter of a much longer story. The character development takes time, so this may be confusing if read 'stand alone'. I highly recommend you start at the beginning of this series, or even better, the original series.

The original starts with the 'Workplace Romance' series and leads into the 'Workplace Romance - Chicago' series.

Hope this is helpful to you. Please enjoy reading them!

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Lunch had been pretty tasty as Michele, Valerie and I had finished eating quickly. We sat at our table, near the back of the room, talking about a lot of things. Considering how lunch had started, with depraved and urgent sex with Valerie just down the hall, I was surprised we even made it to lunch. Taking the elevators to one of our rooms upstairs seemed like a better option. But, I did enjoy talking with them, Michele and I had gone through a lot together and were learning about Valerie now.

Every time Valerie looked at me, she smiled wide, her eyes sparkling. She was no doubt remembering our sexual exploits over the last 18 hours. The pool orgy, then sex for her first time in seven years last night, this morning's wake-up call, and just now, a few moments ago, her depravity reached new heights. Sex in the old phone bank off the hotel corridor had been risky. If we were discovered, someone could have taken it poorly. But damn it was hot, Valerie could not have waited another second to have me inside her. Sex with her over the last day reminded me of my girlfriends in college, after discovering her new toy, she wanted to play with it all the time. Except with Valerie, she'd been more experienced from years ago, all these years since knowing what she was missing. Metaphorically speaking, it was like her damn burst, and there was no holding back the water anymore. She was going to keep going until we all drowned.

There was this other side to her, this professional side, almost celebrity-ish in this setting. As we talked, there were interruptions every few minutes. Many people wanted a book signed, or a selfie with her. She was gracious, and acknowledged everyone, smiling for pictures or personalizing their books.

Michele and I spoke quietly while Valerie was busy with her 'fans'.

"I'm so proud of you Michele." I stated.

"Oh yea? Why is that?" She questioned.

"Last time we were together, we really explored a lot together. We had a lot of fun pushing boundaries. But I think it was mostly me, pushing yours. You got very comfortable with your sexuality and came out of your shell."

"Ok....." she responded, knowing I had more to say.

"This trip, has been the next evolution of Michele in a way. You're pushing your own boundaries and mine. Really exploring new things, and I'm having a lot of fun with you directing things." I finished, wanting a response from her.

"Thank you Scott, you're right, last time, you helped me find something I had hidden inside me. When I went back home, I had to repress that, and seeing you again, allowed me to 'let it out of the box' again. I've missed this part of me that so free and passionate. I am sure you'd feel the same." She started to explain.

"I want this week to be just as special for you as last time felt for me. I want your boundaries pushed!" She smiled, waiting for my response.

Another one of Valerie's book signings finished. She turned to us, "what are you two so engrossed in conversation about?"

"Just reconnecting about our history," Michele answered.

"Well, I have some bad news," Valerie started. "I have a dinner I am supposed to attend tonight, and I can't bring any guests, you two will have to entertain each other without me tonight." She made a pouty face, having some idea what she'd be missing.

"Valerie, I had no idea," Michele started. "Will you be busy all night?"

"Yes, unfortunately." She said frowning now.

"Well, I'll have to make sure we make it up for it tomorrow then." Michele dictated.

Another one of Valerie's fans arrived, book and selfie ready, I turned back to Michele.

"What's that about?" I asked.

"I'll just make sure tomorrow is memorable for her, and you, since it'll be our last day here, I'm actually flying out tomorrow." Michele said with a drop in her voice. Saddened by the words coming from her mouth.

"Well then, we'll have to make tonight special for you." I said confidently. "Since it's just the two of us tonight, let me take the reigns. There's something I want you to experience."

"What?" She questioned.

"You'll see." I smirked and looked at her, knowing I had a bit of quick organizing to do, but if I was able to do it, I wanted to explore a fantasy she'd told me about.

Michele had set her phone in the table, I noted it was unlocked. "Let me borrow this for a minute," as I reached for it she looked at me quizzically.

I quickly found the text from Cassie and memorized her number. Then switched to the camera, I took a picture of Michele, "send that to me", I said in a feigned way over covering my tracks. "I just want a picture of you, just like this." Smiling, Michele took back her phone, a small squint questioning what I was up to, but she sent me the picture as she tucked her phone into her bag.

Valerie's fan left, she focused on us, "the conference is starting again in a few minutes, we should head back in."

We stood and headed towards the door. These beautiful women looked incredible. Both were dressed similarly in their skirt suits, and I knew Valerie had nothing on underneath, but still questioned Michele's choice as their asses jiggled in front of me as we walked. I tried to keep my eyes up for a moment, but it was impossible. That pert ass of Michele's, and the strength in the round globes of Valerie's both their stocking clad legs pouring into their heels made their calves look fantastic. My cock throbbed again. They were both irresistible to me.

"I have to make a quick call." I stated and walked to the wide corridor away from the direction they were heading. As I walked toward the lobby, I quickly called Cassie.

"Hello?" She answered.

"Cassie it's Scott."

"Hey baby, how are you doing?" She responded, now enthusiastic to hear my voice.

"Cassie I'm great, but I want to put together something special for Michele on short notice, you think you and Colt could join us on a dinner cruise? Tonight?"

I could tell she was smiling. "That is short notice honey," that Texas drawl rolling over her lips, "I'll have to get someone to cover my shift, but I like the sound of this."

"Thank you Cassie, I'll owe you one. I'll text you when I have specifics." I said to the point.

"Baby," that drawl thicker than ever, "you don't owe me a thing. Except maybe another look at that beautiful lover of yours."

I smiled, she was still enamored with Michele, as I was.

"Can you recommend a dinner cruise company?" I asked, hoping she'd know one with an 'understanding' staff.

"Of course sweetie, I'll text it to you." She happily complied.

"Thank you again, talk soon!" I ended the call.

My phone buzzed almost immediately with the details for the cruise company. Once in the lobby, the front desk attendants helped me locate a photographer the hotel uses. I called them immediately and they picked up. After a brief discussion about what I had planned, they declined my offer, but recommended a good person instead. My next call was to them, once I described what I had in mind, they eagerly accepted. I told them the cruise company information from Cassie's text, they'd board the boat early and prepare for our arrival, allow us to eat, and have a photo session after dinner. It needed to happen organically, and I didn't want Michele to know ahead of time. My last call was to the dinner cruise company, and after a brief explanation, I was able to charter the entire upper deck of the boat for Michele and I tonight, set expectations about the photo shoot afterwards, and a reservation for two more in their dining cabin for Cassie and Cody. My mouth was watering in anticipation already.

During the walk back down to the conference, I texted Cassie, explaining I wanted their presence to be a surprise until after dinner. She confirmed that she understood, even if she wasn't exactly sure why I was asking.

Returning to the ladies in the conference, they were both seated where we'd left before lunch, I took my seat between the two beautiful women.

Valerie leaned forward and whispered, "I hope you're planning something for Michele. She's done so much to help me, I want you to make tonight special for her."

The thoughtfulness going on in our three-some was comical.

"That's what the call was about Valerie, I'll take good care of her tonight." I whispered back and smiled, winking at her.

She smiled back, and looked over at Michele. She was eyeing both of us carefully, no doubt wondering what we were saying.

"We have a date you and I." I let her know. "Tonight, and I'll expect you to look as beautiful as you do right now."

"That's easy," she smirked, "I look this hot all the time." She finished her statement giggling.

As the first speaker after lunch stepped up to the podium my mind recalled a couple of stories Michele had told me last time we were together. We had talked in depth about many of her fantasies. If I could pull it off, I wanted a couple more to come true for her. There was a fantasy about traveling to Venice and spending time there with a passionate lover. She wanted to see the city from a boat on the water. She wanted to make love to her partner while floating through those canals and people in the buildings they passed by watched. There was also a fantasy about making a sex tape. She wanted to see herself on camera acting out being a porn star in a way. I think, as she described it, she'd always pictured that scene in a hotel, but I know Michele's proclivity towards exhibitionism, so why not combine them? I couldn't bring her Venice tonight, but maybe the lights of the Chicago skyline would be a good substitute.

I was snapped out of my thoughts by her voice, whispering my ear. "Thank you for fulfilling your promise earlier."

She referred to our conversation here this morning and me promising her that she'd taste my next orgasm, which I'd almost messed up had she not been quick to intervene and join Valerie and I in the alcove as I'd begun spurting.

"I hope our date later has you leveling today's score?" She hinted, a questioning tone in her voice.

"Michele," I looked at her sternly, reasserting my control in our relationship. "You're going to lose count of the score tonight. That I assure you." Unblinking I stared into her soul.

She shivered, "you're going to send me into early labor aren't you?" She said smirking.

I still didn't blink, "with what I have planned, probably."

If it's possible to look into a woman's eyes and see her soak through her panties, this was it. She clenched her thighs tight together, as I grinned at her. She was mine again, she'd had fun exploring a different side of herself the past couple days. All of us had thoroughly enjoyed it, and I was proud of her to see her emerge further from the shell I'd found her in a couple months back. But on our last night here, I knew what she needed now, and tonight was my turn.

She smiled, lost in lustful thoughts swirling around her head. She just mouthed, "fuck" silently at me, and turned her head, feigning interest in the speaker.

The rest of the presentation was interesting, but my mind was all over the place with how tonight might play out. I sincerely hoped to fulfill Michele's fantasies. She hadn't said anything to me yet, but I knew after this trip it would be a long time before we saw each other again. I wanted this trip to be memorable. Not just for the sex, but for being thoughtful in making the effort to do something she'd dreamed about, or get it at least close. I wanted it to be special for her, full of depraved acts of sexual gratification, but special too. I smirked at the thought.

Lips whispered in my ear from the other side, Valerie's side. "My pussy hurts, and my throat isn't much better." I could tell she was smiling as she said it, knowing the reaction it would have. She was right, I felt a pulse against my thigh, she woke him up with her words.

"Hey, after last night and this morning, I was going to give you the day off." I quipped.

"If a little pain is the price I pay for what you have done to me." She paused, "what your big cock has done to me..." she let those words sink in, "then you can punish me like that anytime."

I was thickening and throbbing again, any more comments like that, and I'd be showing off a tent to anyone looking.

"I'll take that as an invitation. Good thing you have the night off to recover, tomorrow won't be easy for you. I'm going to make sure we make up for your lost seven years." I told her.

She mouthed "fuck" back at me, like Michele had done, her thighs tensed together too. She squirmed in her seat as she sat back. She was wet again. Mission accomplished, both women getting a taste of their own medicine.

Medicine maybe, but I couldn't stop thinking of how her tight little pussy has just milked me during our alcove antics just before lunch. If she was a drug, I was an addict.

A fast addict at that. We'd only just met on the plane a couple days ago, and already, I was wanting to spend more time with her in the very near future.

We were beginning to connect as Michele and I had, and with reality of Michele's due date around the corner, she'd have bigger priorities than me for quite some time. Silently I'd wondered if she'd move on eventually, focusing on her new, more complete family. I knew being a mother would be all consuming for a while, and since we didn't live close, I imagined it would be a very long time before she was able to travel again and we could be reunited. This trip wasn't planned but it would be her last for a long time, that was for sure. I wondered that while Michele was down for the count, if she'd be supportive of my continuing a relationship with Valerie.

Funny to think of it this way. We were all each other's affairs, but now we'd added another person, it was getting complicated. Michele had been the aggressor in getting Valerie included with the two of us. I hoped that was translating into a hand-off of sorts. They were the relay racers, and I was the baton....literally and figuratively.

"I am completely soaked, my panties are annihilated." The whisper came from Michele, she'd been thinking about what I'd said.

Thump, thump came the feeling against my thigh again. Both of these women exquisitely talented at turning me on.

I played up the control, patting her leg as I whispered back. "Just wait Little One, you haven't felt anything yet."

She shivered. I wanted her primed and ready tonight. I wanted her absolutely, desperately, completely, and totally consumed with desire for me. So far, it was working, her path to later tonight had begun.

Moments later, the speaker was wrapping up. A quick break before the last session of the day, and they we'd be off to our dinner cruise. I peeked at Michele, she held her forearms to her chest. It looked innocent enough, but as my eyes lingered on her, she was rolling her forearms against the silky fabric of her blouse. She was desperately trying to relieve what must have been really hard, aching nipples. I could picture her pink, hard little nubs on the tips of her swollen breasts. Breasts that had more than tripled in size due to her pregnancy. Clearly having sensitive nipples straining into the inside of her bra wasn't comfortable as I saw a pleading in her eyes. She needed a release, or maybe it was just time to turn up the volume.

The room was clearing out fast, everyone headed for the bathrooms or beverage and snack bar outside. Even Valerie took a walk. Michele sat next to me, as I looked over her shoulder, almost every single person was gone. The room fell silent.

I looked at her, turned my chair to face her and grasped the bottom of her chair, turning her to face me directly. She looked at me quizzically.

"Unbutton your blouse." I said with a straight face.

"What? Here? Now?" She stammered, glancing around.

"Blouse, here, now," I confirmed.

She paused, but then quickly took to the top buttons, undoing them in front of me, exposing her creamy flesh as she did. Three buttons down and the swells of her chest came into view above the white lace on her bra. Just one more, and she pulled the sides of the thin material apart, pulling her bra covered breasts from under her shirt. The white lace lay flat against her pale skin, breasts heaving with her labored breathing already. She was already excited from what I'd asked her, told her, to do.

"Open the clasp," I instructed. She looked over her shoulder but did as she was told.

As she released the tiny metal clasp in her cleavage, the sides of her bra swung away as if on springs and her heavy breasts bounced forward. "Oh my," escaped my lips. Here she was, totally exposed in the front of the conference hall. She had gone from an A to a solid D cup for sure thanks to her pregnancy. Her beautiful swollen breasts looked heavy, veins were slightly visible just underneath her creamy skin. Her perfect medium sized pink nipples were rock hard, aching. Her breasts sat proudly atop her round, very pregnant belly. She was absolute perfection in front of me.

I couldn't waste time, people would be flooding in here at any moment. Quickly, I lowered my head to her right breast as my hand grasped her left. My warm mouth descended to her stiff, pink flesh. As my lips made contact I sucked hard. I felt her other nipple in my palm stiffen further, tightening your my touch.

"Mmmm" she whispered at getting the attention she desired. She squirmed in her seat, the attention making her even wetter below.

I flicked her erect little tip with my soft and warm tongue and sucked hard again, immediately rewarded with a stream of her sweet, warm milk squirting into my mouth. As it released for me, she moaned again.

My hands and mouth switched places. I brought her other fleshy hard nub to my lips and sucked. Rewarded again with Michele's very sweet treat.

"Fuck Scott," she whispered.

I sucked and flicked hard as I felt more milk dripping over my hand on her other breast. She brought her hands to both her breasts, cupping and squeezing them, causing the nipple in my mouth to erupt more forcefully.

"Fuck Scott," she repeated.

I switched again and sucked hungrily, knowing full well I'd have to stop suddenly at the slightest noise. She rewarded me again squeezing to increase her flow and release more pressure.

"Fuck Scott, I think I'm gonna come!" She whispered in desperation.

I pulled back, looking at her. Sitting in front of me, her mouth agape, eyes wild with desire, both hands cupping and squeezing her breasts, dribbling her white sweetness over her own hands and onto her belly.

"Stop," I told her. "Button up."

"No, please Scott-" she begged.

"Button up." I repeated.

"Please Scott, I need to come baby, please" she groveled at me.

"Button, up, now" I commanded, still smirking. Wiping her sweet gift from my lips.

She pouted, frowned, but complied. She wrestled her heavy breasts, still leaking, back into her pretty white bra, and quickly buttoned her shirt. As she finished, I looked around, still no one.

I kissed her quickly, her soft lips even pleading with me for more. "Don't worry baby, just come along this ride with me, I promise, you'll enjoy yourself." I smiled and winked at her.

"I'll do anything you ask of me Scott," she responded, still in her pleading tone, "I mean it, anything baby."

I helped turn her chair back and did the same with mine. As I did the first few people made their way back in.