Workplace Romance – Chicago Ch. 08

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Author’s note to readers: Please be advised this is one chapter of a much longer story. The character development takes time, so this may be confusing if read ‘stand alone’. I highly recommend you start at the beginning of this series, or even better, the original series.

The original starts with the ‘Workplace Romance’ series and leads into the ‘Workplace Romance – Chicago’ series.

Hope this is helpful to you. Please enjoy reading them!


My eyes fluttered in the bright morning light streaking in through the windows of our top floor room in the JW in downtown Chicago. I squinted to keep them closed, not ready to wake up yet. I felt warmth next to me, Michele was still asleep in the crook of my arm, head on my chest, her arm and leg draped over me. We’d fallen asleep in this exact position in the early morning hours, both of us so exhausted we hadn’t moved.

A long, hot shower together had preceded our passing out. That much was needed after our night out. My plans to help Michele live out a couple of her fantasies had played out even better than I had anticipated. The sex had been epic, but we’d also connected on that deep, soulful level again. I don’t think we’d gone the rest of the night without touching each other, never wanting to be out of reach. It felt so good to feel this close to someone again. We’d shared a lot, and had some incredible sex, but the intimacy between us ran much deeper.

It was hard to believe we’d spent a total of less than 10 days together, ever. A week, just two months ago, and another this week. It felt crazy to bond like this with someone in such a short time, but we’d had a lot of quality time together. In addition to just talking to each other, there was the incredible physical attraction, which in a number of ways, sped up the intensity of our relationship. It certainly didn’t hurt that we kind of operated in a ‘fantasy land’ of sorts when together. The pressures and responsibilities of mundane daily life never infiltrated our work-vacation lifestyle. That helped keep things pure as well.

Suddenly, her fingernails scraped my belly and she nuzzled her cheek into my chest harder. I thought she’d woken up, but her slow, deliberate breathing hadn’t changed. It wasn’t until that moment I realized I was fully aroused and pulsating. My brain was slowly clearing and focusing on it’s more pressing needs. That morning hard-on could be demanding in the early hours. But I really wanted Michele to wake on her own. Last night was incredible, both emotionally and physically exhausting, especially for her. With today being our last day together for a what might be a long time, I wanted it to be about her. Besides, I knew as soon as she woke up, she wouldn’t let me down in that department either. We were always attentive to each other’s needs.

The drive back to the hotel had been quick. After letting everyone off the boat in front of us, partially because we didn’t want the ambiance to end. But there was also a twinge of embarrassment of having to face the people we’d shared very intimate, arguably carnal desires with, would be difficult. Seeing them sober, no longer drunk on the dopamine coursing through our veins, it might have been uncomfortable. We held hands as we had walked from the boat to the Porsche, and she’d held and stroked my arm as we drove. I remembered how cool the air felt as we drove through the city under the glowing night sky, always partially illuminated above the bright city.

We’d arrived back too late for any hotel bars to still be open, so we’d headed to our adjoining rooms and showered. I let Michele rest and washed every inch of her body in the warm running water. Even with the towel wipe down on the boat after all the sex, her breasts and belly had remained cum-crusted from our sexual gluttony. I took my time, carefully soaping every inch of her, and gently caressing her tender skin in the water. Michele didn’t even open her eyes during the entire experience, just focused on the sensations of my slippery hands on her flesh, and the warm water pouring over both of us.

Finger nails scraped lower down my belly. Slowly, as if driven by an absent-minded lover toying with my skin. But Michele still slept soundly, her breath still deep against my chest. The tips of her fingers found my pulsating erection. They scraped down my throbbing shaft, the tight skin making her incidental touch incredibly erotic. I held my breath for a moment as I focused on her tender touch. Her finger tips just grazed up and down the stiff mast. I let my breath out slowly and quietly trying not to disturb her sleep, or her unconscious attention.

A soft moan escaped her lips, her body stirred, nuzzling in closer, as she did, her hand wrapped around my shaft at the base. Her teasing suddenly felt more desperate as she grasped me. My hand was on her hip, still not wanting to wake her quickly, just holding her close. I couldn’t see it happen, with her head and hair all over my chest, but I was sure a glob of precum escaped the tip. Her breathing changed a bit Bursa Escort from its labored state as the soft skin of her heavy breasts pressed against my rib cage. She fell motionless again, just breathing against me.

For a long time we laid together like that. My own desperation was getting the best of me, I could have waited for more stimulation before, but now with her hand wrapped around my pulsating erection, it was too much. I tightened the muscles in my pelvic floor, forcing my hard-on to thicken in her hand and pulse in her delicate grasp. She moaned unconsciously.

I smirked, that seemed to work, subtle, but got a reaction. Again, muscles flexed, and a moan, this one more urgent, followed with a squeeze from her hand. One more time, one hard flex, followed my her moan, and now her hand slowly stroked my shaft up to the top and back down. I could feel the precum leave the tip and drip onto my belly this time.

I felt her eye lashes flutter against my chest, she moaned again and stroked me with a corresponding squeeze. I moaned in return. My God, even the simplest of attention from Michele felt amazing this morning. Everything was so sensitive.

She stretched her entire body against mine, letting out a quiet roar against my chest as she did.

“Good morning!” She said sweetly.

“Good morning beautiful.” I responded quietly.

“Looks like I found your present for me.” She giggled.

“Mmmhmmm.” Was all I could respond as she stroked and twisted the skin of my shaft in her tiny hand.

“Did I sleep like this all night?” She asked.

“No, you just found your toy a while ago.” I joked back.

“Such a big toy!” I felt her smile against my chest. “Looks like I didn’t wear it out last night…..maybe I should try again this morning?”

“You sure you aren’t worn out from last night?” I asked.

“I am sore, but I’m not letting this beautiful thing go to waste!” She exclaimed, waking up more and stroking me with a little more enthusiasm. “And oh look, my treat!” She lowered her head, lapping a fresh drop of precum escaping the slit and then licked all that had pooled on my belly. “Mmmmmmm, you’re so sweet for me baby!” Her excitement expressed in a whispered moan.

All I could do was moan in response. Then came a thought, I wanted her feelings on last night, we really hadn’t talked much after the sexual crescendo on the boat. “What’s the most sore?”

“I think you pushed my cervix into my throat.”

We both laughed at that one.

“I’m sorry baby.”

“Don’t apologize, I wanted it up there!” As she spoke, she laid her head on my chest again, looking down and playing with her toy in her hand as she spoke. “Damn you felt so good. Yesterday was intense baby. All the buildup keeping me almost edging, wanting you. I don’t know how you planned that, but it was amazing and thoughtful.” I could feel her smiling as she was remembering, all good so far.

“I had always pictured making a sex tape to be from a cell phone in a hotel room or something, nothing as professional as you put together.” She stroked my entire length gently, including cupping my heavy and aching balls now and again as she spoke. I desperately needed more, my aching and the intensity of my erection only increased with her touch. “And I’d always wanted to show off in front of people on a boat, you remembered my Venice fantasy didn’t you?” She didn’t wait for a response, but her hand gripped my shaft tight and she stroked more intensely as she continued. “My God, all those guys and all that cum all over me! All those eyes watching us, even Shannon was so hot joining in. I loved being with you while watched by others. Our movie had a live audience! I wonder how many of those people in the big group went home and had great sex thinking of us? So sexy! Baby, you managed to wrap like three or four fantasies into last night. And I was so glad it ended like it did. I felt so close to you, I mean…” she paused, thinking, “early on it was great sex, but how you finished with me was just so sensual.” She paused to lick the tip of my cock, tasting more precum. The heat from her soft tongue felt amazing in the cool air of the hotel room. “You were so strong, and lasted such a long time, through everyone else’s orgasms. I loved feeling so close to you for so long. Then finally crashing into you was the biggest orgasm of my life!”

I smiled, ‘mission accomplished’, I thought. I’d set out to make it a night for her to remember, based around a couple fantasies, and the way our night played out, I’d apparently over-delivered. She seemed well beyond happy and content.

“Colt’s cock hurt though.” She said a little sad tone in her voice. “I’m sorry I couldn’t take him in front of you.”

“Baby, don’t apologize, Cassie and Colt were there for you. They helped me organize the boat and the people, but him trying to push inside you happened organically, it wasn’t planned. Last night was about your pleasure and fantasies.” I paused, “Honestly, I’m kind of glad you couldn’t take him, that thing scares even Bursa Escort Bayan me.” Chuckling a bit, I tried consoling her and joking too.

“I wanted to try and see if I could,” she continued, “my pussy is just too small.”

“That’s a good thing.” I encouraged her.

“Before him, you were the biggest I’d ever touched, and you know it still takes me a while to be used to you. His was just too much. But I’m okay, he didn’t tear anything.”

“I’m glad you’re okay, and happy you still wanted to make love to me last night.” I soothed her.

“That’s what it was, initially, I needed you to fuck me hard. I needed this toy-” she wiggled my mast back and forth by holding the base. Partially satisfied she licked and sucked the head briefly, “-deep inside me, I wanted my cervix shoved into my throat. But-” she moved her head and tenderly licked down the entire shaft and back up. “What you did after that,” she raised up and looked me in the eyes, “you made love to me. I needed that even more Scott, you were still so strong but more tender. Our eye contact, our kissing, you made last night so special….thank you.” She kissed me softly, lowered her head again to my pulsating flesh in her grasp and licked the tip again. She moaned, no doubt tasting more of my juices.

She lifted her head to my chest, laying it down again. Content for the moment to gently, carefully even, stroke my length in her hand. My hand caressed the soft skin of her little round ass cheek.

“Thank you….but….we did that together Michele,” I confirmed but pivoted, “that lovemaking happened because of us, who we are together, not just what I did to you.”

She smiled against my chest. In the most agreeing tone she spoke softly, “we are so good together.”

After a long pause she continued, “that’s what makes this so hard. I don’t want to leave you and go back home. I don’t want this fantasy to end. I’m afraid I’ll change next month and we’ll never see each other again.”

I felt a tear drip onto my chest from her face. I moved my hand from her butt cheek up to her head and stroked her hair. My body’s attempt to try to calm her a little, and give her some confidence.

“I don’t know what the future holds, but I’m not going anywhere Michele. I’ll be waiting for you when you can see me again.” I tried instilling some confidence in her with my voice too.

“I know you need this as much I as I do,” she sniffled, but strengthened her voice. “So I don’t want you to want for anything. I don’t want you trying to find some random girl to satisfy you when I can’t be there.”

“I won’t-” I started to say.

She lifted her head, and looked at me, a few tears still streaked down her face. I moved to wipe them as she spoke again. “I don’t want you to find some random girl. I want you to help Valerie. I want her to be the one you’re with if I can’t be there. She needs you like I do, and I trust her. I want you to make her as happy as you’ve made me.”

“Michele, I-” she cut me off again.

“Only until we can see each other again, then it’s back to the two of us.” She tried to be confident in her words, but they sounded pleading rather than assured. “I trust her,” she repeated, “and I trust you together. You can do for her what you’ve done for me. I know you can Scott. Make her happy, show her what she’s been missing. Awaken that part in her that you found in me!” She was now smiling, lowering her face, she kissed me so sweetly. “Please Scott, tell me you’ll focus on her for a while.”

I was speechless. She hadn’t really poured her heart out like this about Valerie or the changes coming in a month when she gave birth. We’d had brief conversations about what things would be like after the baby, but I wasn’t prepared for this wave of emotions or her request. Seemed silly to be taken aback, we’d already shared so much with Valerie. In fact yesterday, Valerie and I had discussed the possibility of continuing to see each other, but what Michele was asking was different. What we’d shared, Michele was still the center of. Even when Valerie and I had made love for the first time, her head was in Michele’s lap! I didn’t know if Michele really knew what she was asking of me. What the consequences could be if things went differently than she envisioned.

“Because you’re asking, and you know me better than anyone, I promise you, I’ll try this.” I tried to explain, “but if it gets weird for you or me, I’ll stop immediately and we’ll figure something else out. Okay?”

“Okay.” She agreed, and kissed me passionately, her full lips and warm tongue invading my own, expressing the desperation I’d heard in her voice earlier. This woman astounded me in so many ways, this was really just the beginning of the next evolution of our relationship.

We kissed as her grip became more insistent around my shaft. Tugging gently, squeezing, she milked more precum, I felt it pooling on my belly again. Her mouth was hot, and there was a passion in her kissing that I felt nearly every time we kissed, but I’d never grown tired of. A desperation, Escort Bursa like it might be the last time we ever kissed, then I thought, ‘maybe this would be?’ God I hoped not.

She pulled back from me for a moment, her tiny hand still working my pulsating beast in her grip. She was breathless raising up from our brace.

She smiled wide, and her eyes brightened, and exclaimed, “I want my breakfast in bed!”

She immediately turned, kneeling over me from the side and repeated what she’d done a few moments ago. Licking the precum from the head and the pool on my belly. Moaning as she did.

“Mmmmmm, God you taste so good Scott!”

“I want my breakfast too!” I challenged.

Reaching under her belly and finding her hip, planting my elbow into the bed, I raised her off the bed and swung her close leg over my head so she was straddling me. She steadied herself on her elbows, her pregnant belly making this a bit challenging. As I set her knees down, she found her perfect angle to take my mast, and slowly took every inch past her lips to the base. It felt incredible as I folded a pillow behind my head to bring my mouth right up against her perfect little pussy.

Her juices were already pouring from her body for me. Her smooth lips, and thighs already glistened with her wetness. Her sculpted pink folds slightly engorged and aching for attention. They found all they yearned for as I extended my tongue and slid through her wet slit from front to back. Her beautiful pussy poured more sweet juice for me immediately. She engulfed me again in response.

“Fuck,” I moaned softly into her lips, before continuing to explore her pink flesh.

I loved the taste of this girl’s most sensitive places. Just like strawberries, so sweet and succulent, and always just sopping wet for me. Her clear juices now streamed from her lips and over mine. I could feel my cheeks and chin dripping between her thighs. As I licked, I watched her butt pucker and relax as my tongue tickled her lips. Grasping her cheeks in my strong hands, I continued tasting the breakfast she was all too happy to feed me.

“Mmmhmmmmmm” came a moan from around my cock. She vibrated my mast in her warm mouth as she enjoyed what we both were doing to each other.

She worked over my cock slowly, slipping my hard nine inches entirely past her lips with each stroke of her talented mouth. The heat and warmth from her tongue felt incredible on my skin, stretched tight for her as she used her hands to cup and caress my aching balls. She spread her saliva running down my cock from her lips over my balls and underneath, caressing a slippery finger over my tender starfish. Electric impulses shot through my body as she took me deep at the same time.

Taking a hint, I stretched my neck, slipping my tongue through her honey pot, over her flesh behind and tickled her tiny pink pucker. She clinched and giggled before relaxing and letting me flick my warm and wet tongue over her sensitive flesh. I gently spread her cheeks to allow my tongue better access and was rewarded as she somehow moaned over a throat full of my pulsating mast while slipping her fingers over my own bundle or nerves.

Her mouth felt searingly hot as she pumped slowly back and forth along my entire length. Every inch gliding effortlessly past her lips, over her tongue and deep down her throat. She was so sensual about the entire process. Not rushed or forced like we had been last night, now she was slow, tender, everything was soft and deliberate, it made my need for her just rise higher. My mouth returned to her sweet pussy, gently sucking her lips into my mouth, sliding my tongue between her aching folds, finding her stiffening clit once again. My tongue circled and flicked over her hardening button.

She moaned and slobbered over my cock as I began to flick her clit with more intensity. I was trying to build her up how she was building me, slowly and deliberately. Our tender flesh enjoying each other’s oral talents. I loved all kinds of sex with Michele, but oral, and mutual oral in this beautiful 69 position, was nothing short of breathtaking for both of us. Her body poured more of her clear juices into my mouth. I dipped a finger inside her entrance, it was instantly slippery, then removing it from her between her lips, I tickled it over her starfish. I caressed her pucker with that slippery finger while another finger dipped back inside her steamy cunt. My tongue continued it’s assault on her clit, flicking a little more strongly now, feeling it stiffen further against my warm tongue.

“Mmmhmmmmmm,” came another moan from around my cock, vibrating my flesh in her embrace.

Her fingers slipped around my starfish, her other hand caressing my balls, and her mouth expertly sliding up and down my shaft. I could feel her saliva pouring onto my belly as her efforts became messy.

She grunted and pushed back as I pressed my finger inside her tight little ass. Now I had fingers inside both her entrances as my tongue ravaged her clit. She rocked back and forth onto her invaders as she inhaled my cock, now painfully rock hard. I could feel her struggling to get the bulbous head into her throat, much more enraged than it was before. Both thicker and longer, she struggled and waggled her mouth to feed herself what she desired.

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