Workplace Romance – Chicago Ch. 07 by AlwaysStiffScott

Cassie was getting impatient and pushed my hips to roll me over, exposing my hard cock to the night air as she flipped me onto my back. I lost touch with Michele’s pussy, holding her stocking clad ankle instead. Cassie made eye contact with me and took my cock into her mouth, making it about half way before I felt her tight throat prevent her from going any further. She struggled, pushing down, trying to get more, but my cock didn’t budge. I wasn’t nearly the size of her Colt, then again, who was? But I was still too bit for her to swallow whole. I smirked a little realizing that Michele still retained her ‘title’.

Moaning from Colt stopped both Cassie and I as we looked up at them. Still slipping between her tits, his head even making contact with her big round belly as Michele sucked and licked underneath him. Cassie moved off me and to Michele underneath Colt’s pumping ass. She whispered something, Michele didn’t stop her attention to Colt’s heavy balls but shook her head violently back and forth. Then Cassie moved up to Colt and whispered something to him. He stopped fucking her soft globes and moved to Michele’s side. Cassie said something else, and this time, Michele’s head shake evolved into a yes nod. Seconds later Colt was helping me up to sit near Michele’s head and he repositioned himself between her legs, flopping that monster down onto her round belly. Cassie had walked off to his pants, but returned quickly with a small bottle of lube we were familiar with from yesterday.

Michele looked up at me, her eyes pleading behind her messy face, coated in her saliva, and breasts still covered in a mixture of her spit and Chris’ cum. She was a mess, and looked a little scared at what was happening. I stroked her head in my lap next to my rock hard erection.

Cassie squirted the entire bottle into her hand and vigorously rubbed Colt’s massive tool. She also rubbed Michele’s folds gently as Colt moved himself to position his monster at her entrance. Cassie took Michele’s hand and guided it to Colt’s pulsating shaft, thick and veiny, looking impossibly larger in her tiny hand. She rubbed his huge head through her slit, jumping a little as it slipped over her sensitive clit, back down, splitting her labia on either side of the bulbous head. She guided him down slowly to her entrance again.

Michele tensed up, grasping my cock in her other hand, I watched her bite her lip and hold her breath. I stroked her hair gently to try and calm her as Cassie rubbed Michele’s immensely swollen breasts. I could see milk emerging in droplets from her nipples as a Cassie touched her.

Colt lifted his weight onto his hands on either side of her, allowing Michele the guiding control she needed and began to press into her entrance. The impossibly large head began to stretch her tight little opening. I thought for a moment, ‘he’s going to ruin her’ as I watched him try to press inside.

“Fuck!” Michele cried out, tears welling in her eyes. “No, no, no, go slow!”

Colt was going slow, looking down I could see barely an inch if the head had entered her. The crown still my wider than her inner labia seemed to be able to stretch. He pressed again, Michele’s grip on my cock intensified as tears once again began to stream down her face.

Colt eased up, pulling back out, Michele’s grip on him still tight, beginning to slid him through her own slit again. After a few deep breaths, Michele said “ok” sheepishly.

She lined him up and Colt flexed his hips again, only an inch at first, then another, the head beginning to stretch her painfully.

“Fuuuuuuuck, it hurts, it fucking hurts!” Michele wailed into the night sky.

Colt backed out again. I wiped the tears from a Michele’s face as she breathed hard through clenched teeth. Spit flying around her face. Colt pressed again, this time more forcefully, she screamed as every inch of his massive head pressed inside and her pussy snapped down on his shaft. Momentary relief from the huge head, but her sex still stretched further than ever around his pulsating mast.

She sobbed in my lap, crying out loud as she realized her body couldn’t take it. I looked at Colt, he wasn’t moving and inch, and seemed to have a guilty expression on his face. Cassie tried to calm her, but Michele cried openly her legs restless trying to ease the pain between them.

“Please!” She pleaded, “make him stop,” she sniffled back snot and tears, “get him out of me, I can’t take it anymore!”

Cassie nodded at Colt, and he began to pull back. Michele’s tight entrance gripped the crown with such force all he did was make the pain worse for a moment. She wailed again.

“Fuuuuuuucccckkk!” She screamed as more tears streamed down her cheeks.

Her lips finally stretched over the ridge and as they reached their thinnest point, nearly ripping, quickly slipped over and shoved him back out of her, her pussy closing on itself.

Michele was shaking uncontrollably, I stroked her hair, her grip on my now completely purple cock slightly released some pressure. Cassie kissed Michele deeply, and forced Colt into a sitting position next to Michele on the padded seats. She straddled him immediately and after pausing to position that same massive head at her entrance and giving the cameras time to zoom in, she looked at Michele and made that entire length disappear inside her.

“Fuck” she grunted as her ample ass smacked against Colts thighs. She wrapped her arms around him tightly and rode him like a rodeo star. Rough and hard she pounded his huge flesh inside her, rearranging her organs. He grunted with her powerful thrusts.

Michele watched her, her fingers beginning to trace circles on her belly and the cum still splattering her boobs. She watched Cassie do what her body couldn’t in amazement. Knowing now just what it felt like, she watched her rise and fall, I began to stroke her face and her neck.

Michele clutched her breasts and rolled her nipples as we watched the Texans fuck hard. Michele becoming more relaxed she turned her head and licked my shaft, still hard in her hand. The wetness of her mouth felt incredible again as she licked the pulsating veins. She rolled over to her hands and knees and impaled herself on my entire nine inches again. Gasps from the crowd still sticky and naked, watching us with intent.

Michele may not have been able to take that horse cock inside her, but she was my little queen of deep throating my tool. She rocked back and forth, letting my length nearly slip from her full lips before taking every inch again down to my balls. She moaned, gagged a little, gasped for breath now and again.

We looked over and Cassie and a Colt were both watching us as she buried that baseball bat inside her with more intensity. Beginning to grunt and cry out with each stroke.

Beyond them, our crowd, still slippery from round one were back to touching themselves. The guys feverishly stroking life back into their cocks and Shannon rubbing her mound for all it’s worth. They just stared and watched us please each other.

Cassie grunted, “aaaagggghhhhh” drove him deep and came forcefully all over his cock. She shuttered and I heard splashing down on the deck as her juices overflowed from both of them, her sweet release drenching him too.

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