Workplace Romance – Chicago Ch. 07 by AlwaysStiffScott

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.

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