Workplace Romance - Chicago Ch. 04

Immediately the guy sitting on the side groaned as his partner slowed her strokes. He tensed, and arched his body, throwing his head back, she held him still. Just her single hand gripping him just beneath the crown. He erupted in a long thick rope that splashed into the water, another, and another, the last few dribbled into her fist as his orgasm subsided.

I looked over at Michele, Cassie and Valerie were both suckling from her swollen breasts. From the expression on her face, and the moaning from the two girls latched onto her, I think her heavy globes were rewarding them like she had done with me last night. I envisioned warm, sweet milk squirting from her perfect nipples, filling their mouths as they hungrily sucked each precious mound of flesh. Under the water, their hands worked on Michele as well, working expertly inside her folds I imagined, other hands over her pert little ass under the water. All the time, Michele just looked at me, her eyes filled with lust, and desire, these beautiful women satisfying her as she watched Jenny stroking my length as I stood on the edge of the pool.

My orgasm grew closer, I could feel it, my breathing increased and I uncontrollably moaned as she stroked more slowly as my cock thickened further in her grasp.

Michele tensed, she gave me a look I've seen from her often, that blissful, beautiful agony as her face contorted and she came for the women touching her. Her body shook through more waves, and she never closed her eyes, always on me, watching, showing off. She wanted me to share in her pleasure the other women were bringing her.

As Michele came down, the girls softened their attention on her and she still watched me. She said something quickly to Cassie and Valerie. Cassie pulled off her breast, the nipple squirting a thin white arc of milk into the pool.

"Jenny!" Cassie called to the girl stroking my cock, "...she says you'd better not waste that!"

Jenny made even slower movements, delaying my impending release which I wanted so badly. As she did, Michele pulled Valerie off her other breast and moved to the edge of the pool near me. This breast also leaking sweet milk over her skin as she moved as quickly as she could towards me.

Jenny released my balls and urged me down, pressing on my shoulder, and brought me to a kneeling position by the edge of the water. Her hand returned between my legs to my jewels, heavy and aching in her grasp as her other hand continued to stroke me. Squeezing and stroking perfectly as Michele reached me. She looked at me with her beautiful eyes, her sweet voice encouraging me to finish how she wanted me to.

"Come for me Scott, I want to taste you, You can come for me, fill my mouth with all your sweet cum." She opened her mouth wide just an inch from the tip of my cock, and extended her tongue, licking the frenulum just under the throbbing, angry head. I couldn't hold off any longer, I didn't want to, I wanted to please Michele.

My heavy balls tightened and boiled over. Warm tingling began rushing though my whole body from my core to my face and finger tips. My heavy balls leapt in Jenny's little hand. She was still stroking slowly as I erupted into Michele's mouth. Spurts of warm and creamy cum squirted onto her tongue, and filled her mouth. With each pulse of my cock, Jenny held my cock pointed at Michele's mouth, sending my seed flying into her open mouth. My legs went weak and I sat back on my ankles, watching Michele closing her mouth. Smiling with an overflowing mouthful of my creamy sweetness.

It was then I noticed Valerie, standing next to Michele and caressing her breasts and belly. Her other hand working over her own clit furiously, her arm splashed at the surface as she rubbed her hard little pearl towards her own orgasm. She had watched every drop shoot into Michele's mouth.

"Please share," she pleaded, "let me taste him!"

Michele leaned towards her for a kiss, Valerie met her half way, still rubbing her clit quickly, opening her mouth to Valerie as their lips met. Tongues immediately dancing with one another as Michele shared my cream with her, Valerie moaned. Her hand working underwater suddenly froze, her entire body tensed as every muscle instantly flexed. She groaned as her body shuttered through her orgasmic wave. As their lips parted, a tiny drop left their embrace and dribbled down Michele's chin. Streaking a bit of cloudy white juice on her skin. Both girls swallowed.

Valerie, opened her eyes, and looked up at me, "you taste so good!" And smiled wide, "you're not bitter at all, sweet like fruit."

Jenny had released my cock moments ago and joined her husband on their lounge. The two couples from the hot tub jumped in the pool and moved closer. The couple that had been having sex on the far end of the pool alone, moved closer to this edge. All of us now surrounding the single couple still pleasing each other.

When Michele had moved toward me, Cassie had gone straight for the horse cock laying over Colt's thigh. As I was emptying what seemed like a quart of cream into Michele's waiting mouth, Cassie was using both hands to stroke his impressive length. She licked the huge head, swirling her tongue around it and sliding her tongue down the underside of his entire length and back up again. She worked her hands in unison along his shaft, making that impossibly large spear rock hard.

Now, with everyone watching, she began to make a show of it. Licking, smacking the weight against her tongue, giggling at the sensations. She clearly enjoyed playing with his monster that was bigger than her forearm. Colt moaned at her attention, he laid back on the pool deck, stretching out as Cassie worked his flesh from between his legs.

She sat up on the edge and pulled his massive meat between her enormous globes. She tucked him between those huge mounds clutching them tight on either side of his pole and began to move up and down, letting her epic breasts do the work. She spit on the head as it poked through her cleavage, making it more slippery and enjoyable for him as she worked him over putting on quite a show for us. Her impressively long and hard nipples tightened further as she stroked him through her ample cleavage.

As we watched, I slipped into the pool to be closer to Michele, held her in my arms and kissed her neck as we watched. Valerie was close to us, sitting on the pool deck, lazily rubbing her clit as she watched Cassie play with Colt.

Everyone else was with their partners, watching intently as they mindlessly touched each other. Cassie was enjoying being the center of attention, she liked showing off.

Cassie pulled Colt's cock from her breasts and desperately tried to taking him into her mouth as she stroked his long shaft with both hands. She couldn't get the thick head past her lips, only succeeding in sucking the tip. Giving up, she let his cock go, and it landed on his firm belly with a loud 'smack'. The weight apparent even more up close.

She crawled out of the pool quickly and stood over Colt, straddling him with her feet on either side of his hips. She bent over and grasped his cock in one hand, stroking him lightly.

"Get it babe." She said to Colt.

Colt's pants were within reach and he quickly reached into a pocket and produced a small bottle. Flicking the top open, he poured a clear slippery liquid all over the head of his cock in her grasp. Lube, when you're that big, I guess you keep it with you constantly. Cassie immediately began stroking his length, smearing it all over his flesh pulsating in her hand. He continued pouring the lube until she nodded at him. He dropped the bottle as she continued to stroke his length. When she felt every inch was slick, she squatted and began to position the enormous head of his cock at her entrance. Everyone around them watched in anticipation, with absolutely no idea how this was going to work. He looked too big in every way, too long, too much girth. It pulsated hard in her grasp as she slipped the head through her slit, soaking the head with her own juice until she had him right at her entrance.

"Stop!" Valerie yelled. She startled everyone, not least of all Cassie.

"I want to hold it as you fuck him!" She commanded.

"Well get over here baby and hold this beautiful man's tree trunk for me!" Cassie quipped back.

Valerie moved swiftly, sitting next to them and taking his heavy cock by the base. She leaned it back and forth a little admiring the weight and girth as she slipped it through Cassie's folds. Then positioning it straight up in the air for her, the tip just putting pressure to stretch her tight entrance.

As she lowered her pussy just a bit, her swollen inner lips hung from her pussy, dripping her own juices down his length. Those inner lips looked a little stretched from riding his monster for years. Definitely not as tight as the 'paper-cut' between Valerie's legs that she was now slipping juices from to rub circles around her aching little pearl. Cassie maneuvered her hips to line up her entrance just perfectly.

She paused as the thick head nuzzled her entrance. Cassie looked at Colt, and he looked at her.

"You hold my baby tight now, you hear?" She told Valerie in that Texas drawl. Valerie squeezed harder to hold him in place, his cock throbbed in response growing impossibly thicker, every vein and ridge pulsating and ready.

She looked back at Colt, took a moment to ready herself mentally, and then in one violent motion, slammed his cock all the way home.

"Fuck!" She grunted.

Ripping its way through her pussy until her lips stopped on Valerie's fist, holding the last two inches in her grasp. The head must have torn through her and hit her larynx. We all stood astounded at where his entire mast had gone.

Once she knew it was all the way in, began sliding up and down that long shaft, Valerie's hand keeping a tight grip. Each squat, Cassie's pussy rubbed against Valerie's hand, still clutching his cock tight.

After a few strokes, she asked Valerie to remove her hand. She did, slowly, and reached around to hold his heavy balls as his cock pressed that last two inches until her lips came to rest on his pelvis. He was completely inside her.

Cassie looked uncomfortable, someplace between pleasure and pain. She paused to catch her breath and mentally adjust, and then started riding him like a proud Texas cowgirl would ride anyone. She squatted over him, hands on his chest, and rose and fell nearly his entire length with each stroke. Every time her ass smacked down on the tops of his legs, leaving no doubt, he was fully inside her. Her pussy stretched with his girth, and each time she was near the top of her stroke, we could see the ridge of the crown pulling and stretching her inner lips around him. Each time after, she drove him deep again.

They both grunted and moaned as they fucked hard with all of us watching. Everyone was toying with their partners but mostly watching the show Cassie had invited us to see. Michele was mesmerized at how Colt's massive flesh penetrated Cassie, she watched every stroke. Valerie was holding his heavy jewels but looking the two of them over, watching their faces, their bodies, and enjoying the penetration just an inch from her helping hand.

She rode him hard, almost violently as she gritted her teeth, and kept pounding his flesh. Uncontrolled grunts escaped her lips each time be bottomed out deep inside her. Her pace increased, her noises more audible and intense. Both of them breathing heavy as she thrust into him over and over.

"Oh baby," she started, "please come for me, I'm about to come all over that beautiful cock!"

Valerie just cupped his heavy balls, and gave us a devilish smirk.

I looked at Colt's eyes, they watched his cock disappear over and over into her slippery warm cavern. He grasped her ass cheeks hard and pulled her into him, his back arched on the pool deck, and his hips lifted them both in the air as grunted into her heavy breasts smothering his face.

"Mmmmmmmmm" was all we could here as he unloaded deep inside her. She threw her head back and drove him impossibly deeper. Her entire body shuddered as she cried out.

"Colt!" She shrieked.

Their bodies flexed and shuddered together until Cassie collapsed onto his chest. Both of them breathing heavy and sweating all over each other. From our view, we could see his cock convulsing inside her.

Valerie released his balls, and moved back towards us. She wrapped her arm around me and I moved one of mine to hold both of them now, one in each arm.

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.