Workplace Romance – Chicago Ch. 04 by AlwaysStiffScott

After a long time, Cassie rolled off Colt. His cock slipping from her cavern with an audible ‘plop’ back onto his thigh. She lay with her legs spread, the now stretched opening to her well fucked cavern leaked a copious amount of their creamy mixture.

Michele, Valerie and I held each other and moved through the water aimlessly. Our focus no longer on the intense sex we’d just been a part of, but just to just relax. We said nothing, just floated and enjoyed being close.

Several of the guests slowly searched for their clothes and began to get dressed and left. But the three of us just relaxed for a bit, content to be together, enjoying our moment on this rooftop.

The pool was cool, relaxing, and as we huddled naked together in it, I felt close to both of these beautiful women. Michele and I knew each other very well, and we were just getting to know Valerie, but I liked what I had seen so far. Like Michele and I, she was a little broken in her long term relationship. She was missing excitement and intimacy, made to feel bad about her body, and now she’d found some confidence in Chicago. I smiled wrapping my arms around these two beautiful women.

Cassie and Colt had slipped their way into the pool as well. The band packed up, as did the bartender. I’d forgotten all about their wandering eyes in the midst of all the excitement. Guests left in couples, and soon it was just the five of us basking the the water, still naked and sated from our evening.

Cassie broke the silence. “Did y’all have fun?” That thick Texas accent emphasizing ‘fun’, made me smile.

Michele answered for the three of us, “yes we did Cassie, thank you so much for inviting us, it was…” she paused, trying to find the right word, “incredible.”

“Good,” Cassie continued. “Y’all are welcome to stay the night, we’ve got more bedrooms than we know what to do with.”

“Thanks Cassie,” I spoke up, “but we’ve got the conference early, we should probably head back to the hotel.”

“Okay sweetie,” she responded.

We separated in the pool, and exited the water our naked bodies finding the cool night air on the roof of this building a little brisk. We huddled in towels for a moment before wrapping ourselves in them and picking our clothes off the pool deck where they’d been shed earlier in moments of desire.

Cassie and Colt got out too, I turned when they did, trying to give them some privacy. They dried off and wrapped themselves in towels.

“Ya’ll at least want a shower?” Cassie asked.

“That would be wonderful.” Valerie responded for us.

With all of us wrapped in nothing but towels, holding our clothes, we walked back inside together. Cassie led us each to our own bathroom, and individually, we cleaned up.

We met back in the dining room, the women had taken the time to dry their hair and style it again, they both looked like it was the start of the night instead of past the ‘main event’ already.

Cassie met the three of us in the dining room. We said our thanks and goodbyes again, grabbed our keys and phones from the dining room table, and headed out. Valerie followed us in her rental, back to the JW where somehow, Cassie had orchestrated all this in the last few days. I smiled to myself as we drove, Michele’s hand on my arm, her blonde hair blowing in the cool night air.

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