Michele, Valerie, and I did as we were told, putting phones and keys on the table, and then Cassie led us up the marble staircase. A giant multi-purpose room with more floor to ceiling windows, a pool table, a large couch with a massive projector screen, and out all of the windows, Lake Michigan, and the rooftop pool where her guests were spread out around the deck.
As we walked outside, the air filled with music, a small 4 piece jazz band played in the corner, and a bar tender was pouring drinks for a couple next to them. Well dressed couples were standing and talking, one couple quietly admiring the view, there must have been a dozen people already here and enjoying themselves. Some of them looked our way as we observed the activity on the roof.
A tall man dressed in all black, t-shirt, jeans, cowboy boots, a large cowboy hat. The only thing not black was a huge gleaming belt buckle. It was polished to a mirrored finish and stood out proudly. He strolled over casually and put his arm around Cassie’s waist. He pulled her intimately close.
“This is Colt, my boyfriend.” She beamed as she kissed him on the cheek. He smiled.
I stuck out my hand, “nice to meet you Colt, I’m Scott, this is Michele, and Valerie.” A firm grip met mine, hands that had been toughened up with a lifetime of manual labor.
“Pleased to meet the three of you,” he eyed me briefly, and took his time ogling the beautiful women at my sides in skin tight dresses. He paused at Michele’s belly, eyes opening a little wider.
“What’d you win that for?” I asked pointing at his belt buckle.
“Texas State Bull Riding Champion in 2004” he said quietly.
Cassie giggled, “You should see the one they gave me for riding him the first time! And he lasted a lot longer than 8 seconds!” Cassie burst out laughing, Colt looked slightly embarrassed for a second, then planted a passionate kiss on her neck.
We laughed, a little nervously as we looked at the two of them. I now pictured Cassie perched on top of Colt like he was a horse that needed breaking. Smirking larger now, we started toward the pool.
Cassie introduced the three of us to her neighbors, they lived 3 floors down. He was early forties, decent shape, about 6’1, made some money starting some software company I didn’t recognize. She was late 30s, attractive with strawberry blonde hair, petite upper body with a big juicy butt stuffed into the slacks she had on, they had twin teenagers away at college. They joked about being empty nesters most of the year.
It was polite conversation, no sexual overtones except for roaming eyes. Jenny seemed to be looking me over quite a bit when she wasn’t staring at Doug. But it was so polite that I began to wonder if we had all misunderstood Cassie moments ago. We moved on as Cassie introduced us to another couple, we chatted briefly before they broke off to go dance in front of the band.
Michele hugged my arm close as we both sipped water, Valerie stood close by. The three of us made some small talk about the incredible view from up here. One end overlooked the lake, and in the other directions was the Chicago skyline.
Paired shrieks from the hot tub at the far end of the pool were the first sign that this party was anything but a stuffy cocktail hour on the top floor of a high rise. I followed Michele’s eyes, and found what had gotten our attention.
Two couples were in the hot tub. The men sitting down on the edge, their pants rolled up and feet in the water. But the women, two blondes, with large breasts had stripped off their dresses and were in the middle of the hot tub naked from the waist up. At least that’s all we could see, just as their bodies came together in the middle of the tub. Their breasts pressed together as their arms embraced and their mouths found each other in a hungry kiss.
“Well now,” Michele whispered, “that changes some things.” She said smirking, looking back at me before taking in the sight before us again. I surveyed the other guests, most equally surprised, but none of them looked appalled, just excited to be watching to beautiful strangers kissing madly.
I moved behind Michele, placing my strong hands on her hips and kissing the back of her neck. A soft moan escaped her lips as we both watched the couples in the water. The guys were now stripping off their clothing quickly. Once naked, they hopped back in the water to join the girls who’s hands had started roaming each other’s bodies.
Such a sexy scene, as I continued kissing Michele’s neck, and nibbling her ear. She turned and noticed something. She stopped me and flicked her head in a direction off to the side towards the lounge chairs.
The couple from downstairs, Doug and Jenny, sat together, only ten feet away from us. She was behind him, as he was intently watching the action in the hot tub. She had unbuckled his belt and opened his fly, and pulled his cock out of his pants. Reaching around him she now stroked his cock slowly. She was whispering something in his ear as her hand slipped back and forth along his shaft.
Michele watched intently as she continued stroking him, watching him stiffen further in her grasp. The hot tub couples were still total strangers, and it was sexy to watch them. But this couple, we’d spoken with for 15 minutes or so, and they seemed a bit uptight. Clearly we had a lot to learn about reading people.
We were close enough to see her swipe her thumb over his head, smearing the silky fluid leaking from the tip in her hand and down his shaft, lubricating her efforts.
Valerie stood just a bit closer to them, between where I stood and their chair. She bit her lip while watching intently. I could only imagine what other reactions were happening under her tight red dress. Were her nipples hard? Was that beautiful slit of her tiny pussy wet?
Michele moaned at the sight of his cock beginning to pour globs of clear fluid. She reached between us and gave my hardening cock a squeeze. She groaned again as her fingers wrapped around the thick shaft still buried in my suit pants. A groan escaped my lips as she did, finally feeling her fingers on my throbbing flesh again.
To our left two people seemed to appear out of thin air. It was Cassie and her boyfriend Colt. They took turns watching the couple on the lounge, and the foursome gaining momentum in the hot tub, and then turning towards each other and kissing each other madly.
“I am so hot baby!” Cassie exclaimed to Colt, but she was looking at Michele as the words left her lips.
Cassie reached down to the hem of her black babydoll dress, and began to pull it up over her thighs. The material stretched as it rose, revealing she wore no panties, and continuing to slide up her body quickly. She raised her arms, peeled the dress over her ample chest, and disposed of her dress onto the cool deck.
After slipping off her boots, she stood in front of us in just her black balconette bra, which pressed her huge breasts up high. Her soft mounds heaving out the top of the low cut material, which barely contained her heavy breasts. Her freshly waxed or shaven bare mound glistened with her wetness from the light of the pool. Her thick hips and thighs only accentuated her curvy figure. I had been right the other night, seeing her now, nearly naked, Cassie had a lot of everything.