Workplace Romance – Chicago Ch. 05 by AlwaysStiffScott

I leaned down to kiss her, our mouths sealing our passion for each other and begin to ever so slowly press my hips forward. The throbbing purple head just beginning to stretch her slightly.

Her body tensed, legs taught, she held her breath as the invader paused. I held perfectly still and waited for her to relax. After a moment, her muscles softened and she exhaled. I felt her entrance relax a bit as well and resumed my task. I pressed the crown further against her incredibly tight cavern entrance.

It felt as if I was trying to pry my cock inside a steel ring, too small for my girth. She was so tight, her newly virginal pussy, not touched for years, was protective of her depths making progress slow. It was strained, and I could tell, painful for her, but euphoric as well.

She relaxed again and I pushed further. The crown now stretching her tender flesh and muscles to their limit.

She cried out, “Don’t stop!” Tears streamed down her face as she reached around, grasping my ass and pulling my hips into her.

She wailed again, “Ungh Scott!” As her muscles allowed the invading ridge inside and snapped down around the shaft. Her impossibly tight pussy was also fiery hot and wet, and the sensations on my head, with her clutching me tightly right over my frenulum nearly made me unload right then as I pulsed inside her.

I lowered my lips to hers and kissed her passionately again. She moaned into my mouth as I tasted her salty tears on her lips. We kissed as I held myself still, waiting for more encouragement as well as trying to pause my own orgasm rushing closer from the sensation of finally being one with her.

I pressed forward slow as we kissed, just an inch of my shaft pressing inside her body. Pausing briefly then I pulled back slightly until I felt her muscles clutching the base of the crown. Then forward again, another inch. She clutched my cheeks tighter and grunted into my mouth.

“Yes Scott!” She shrieked.

Back and forth a couple more strokes and she relaxed further, now taking about half my length inside her tight cavern. I reached under her back, her head still laying on Michele’s thigh, and clutched her body lovingly up against mine. My strong chest pressed hard against her huge soft mounds. Passionately kissing she moaned in my mouth again.

I tried to think of anything but coming, I did not want this to end before it began. She’d waited too long for this moment not to be perfect. I paused, opening my eyes and looking at her as she kissed me. Making sure she was still okay, she pulled me deeper with her strong arms and another inch slipped into her depths.

“Oh baby,” was about all I could say. Focused entirely on the tight super-heated folds gripping half my cock buried inside her.

“Scott, please, keep going, don’t stop.” She pleaded with me again.

I found a slow rhythm she was comfortable with, shallow strokes as her body adjusted to it’s first penetration in years. Every few strokes I tried to press a little deeper, finally the head nuzzled her cervix and I knew how deep I could go. I held still, just pulsating inside her.

She shuddered softly, a little orgasm washed over her as I still held her close.

With the last couple inches of my throbbing mast still outside her perfect pussy lips, I silently noted her depth. So I began longer, deeper strokes, each time pulling back, the massive head rubbed against her g spot, so swollen I could feel the spongy flesh against my pulsating member. Each stroke went deep, back up against her cervix, nuzzling it just to make sure she felt full, gentle enough not to cause pain.

“Oh my God Scott!” She shrieked loudly.

I took that as a good sign and continued my invasion with more urgency. Faster for a few moments, then slower again. Changing the sensations for both of us. We stopped kissing and just looked into each other’s eyes. I changed strokes to be shallow and then deep, giving her body the variety it craved.

She began to flex back in into me as well, joining my body in our lovemaking. Clutching and grasping at each other as my cock continued to stretch her pussy with our joined thrusts. We were moaning into each other as our bodies took over, the sensations too much to comprehend for both of us.

She called out, “Yes Scott, fuck me baby!”

I responded immediately, pushing up on my hands, giving our sweating bodies air between us, and allowing us to focus on the sensations of our throbbing, and sensitive joined flesh. I began to pick up my pace, fucking her harder and faster as she demanded.

“Yes!” She wailed, “give it to me!”

My cock now invaded her with urgency, pounding her flesh, I felt her pussy lengthen under the pressure. Soon every inch of my throbbing mast was inside her, each stroke, my balls smacking against her ass as I began to drive harder.

She screamed at me, “yes baby!”

I fucked her hard, and deep, jamming her body down into the bed. The three of us bounced as the soft mattress cushioned her body against my driving force. Her body convulsed against me, flooding my cock with her juices as she came again. Her warmth squirting off my pelvis and pooling underneath us as I never stopped ramming my mast into her tender flesh.

She shrieked and cried out in agony, encouraging me as she took everything I could give her. My muscles burned as I drove inside her over and over. She came again, soaking both of us, but I never relented. Again and again she called out for me, finally begging me to finish.

“Come for me Scott, please baby, come deep inside me!”

That was all it took, her desperate words sent my own orgasm into overdrive. My balls boiled and tightened, I took a last few deep strokes slowly, enjoying the sensations, finally stopping deep against her cervix. She was completely full, her pussy gripping me tight, as my liquid warmth shot from my balls, through the length of my shaft, and emptied my creamy goodness inside her. I shuddered and flexed my hips hard as she clutched my ass, pulling me in deeper. Jets of my hot cum erupting inside her body as she shook through her own orgasm again.

“Scott, I’m cumming baby!” She shrieked as I felt that familiar flood of her sweet nectar again.

My cock pulsed again and again, each time hosing off her desperate flesh now milking me for every drop. As my body emptied itself inside hers, we kissed passionately. Enjoying the feelings our intertwined bodies as we emptied our souls into each other’s clutches. Endlessly it seemed, our bodies convulsed into each other.

I collapsed as my orgasm neared it’s end, trying to hold some of my weight on my elbows, her tight grip on me loosened slightly to hold me tenderly. As our orgasms subsided and our muscles eventually relaxed, we laid there for a long, long time. Michele stroked both our heads as her fingers slipped through our hair. Absolute bliss as we laid together, still joined as one, as our breathing slowed and we fully relaxed, exhausted.

I don’t know how long we stayed like that, or if I’d fallen asleep or not, or if she had. But I felt her lips on mine, kissing me softly. No longer with the urgency we had before, but tender and slow. I could feel her breathing slowly against me, I could feel Michele too. Both Valerie and I had collapsed between her legs as she continued to touch us gently. Valerie and I kissed a long time.

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