Workplace Romance - Chicago Ch. 04

My jaw dropped again. It wasn't surprising that we would be getting intimate, I'd guessed that on the plane, but what surprised me is Michele running the show again. She was embracing her new found boldness in asking for what she wanted. I loved seeing her come out of her old 'shell'.

Our last week together two months ago had ended up in a journey of self discovery. She'd fully opened up to me as we explored things sexually she and I had only fantasized about. I helped her make several fantasies a reality for her, as she stepped away from the oppression she'd lived under for years. Made to feel bad about herself, her body, her needs, but all that fell away with me.

As it turned out, it was a healthy trip both physically and emotionally as she'd gained a lot of self confidence, particularly regarding how she felt about herself during her pregnancy. I could see the changes during the week, and I was seeing more now. She'd continued to grow and build on what we started, and I was really enjoying what I was seeing.

Valerie responded with a smile, "that sounds interesting, I'd like to hear more about this party later, just promise me, we'll have some time together alone, after the party?" She asked, never breaking eye contact with Michele.

Michele smiled, "you can count on it. If the host disagrees, the three of us will have dinner tomorrow night instead. Sound good?"

"Perfect." Valerie responded, looking Michele over with her eyes. I watched as she paused on Michele's heavy breasts trapped under her suit jacket much like her own were. I felt Valerie's big breast heave as she took a deep breath, her large globe still pressed into my arm.

We all smiled, knowingly, you could cut the sexual tension with the steak knives on the table from our lunch. These beautiful women, flirting with each other, quite literally with me in the middle. My cock was straining now, thick and throbbing further, my heavy balls ached with desperation, I needed a release.

Valerie left the table and headed back into the conference. Michele put her little hand on my arm, silently telling me to stay seated. More people left the room, and soon no one was anywhere near us, just a few stragglers finishing up their meal and not paying attention to us. Michele quickly turned directly towards me. She looked over her shoulder, making sure no one was around again. She then unbuttoned her suit jacket, and pulled the lapels open. I could see what she wanted to show me, her thin white blouse stretched tight, barely covering her swollen breasts. They were spilling out of her bra again like they had yesterday, and her pink nipples were rock hard, pressed through the fabric of her bra and her blouse as well.

"They hurt Scott," she began, "they need your mouth right now," she pleaded with me.

All I wanted to do was tear open her thin shirt and suck her beautiful nips into my warm mouth. I desperately wanted to lay her on this table, pull her breasts from the confines of her undersized bra and suck, lick, and nibble her perfect breasts, and I wanted it now. My cock pulsated hard over and over. I twisted my legs out from under the table, grabbed my cock and readjusted it in my pants as I turned towards Michele. Her eyes fell onto my crotch.

"Holy shit!" She said softly, her mouth agape, licking her lips as her eyes sparkled.

I was stretched down my leg, tenting my suit pants as my cock was trying to tear through my boxer briefs, desperate to be released. I could feel it pulsating against my leg.

She looked over her shoulder again, and grasped her swollen breasts in both her hands. Then turned her head back towards me, her eyes went right to my cock and so did one of her hands. She grasped the thick shaft, stroking it playfully, her big beautiful tits bounced in front of me as she giggled.

My God, she stroked me right here where someone could catch us! My mind raced, but didn't want her to stop. She watched her own small hand wrap around my flesh, gripping tightly and stroking the length still straining my pants.

I didn't want her to stop, she had me desperate and not thinking straight any longer. At this point, I wanted her so badly, I didn't care about the consequences. I could have ripped off her clothes and torn into her hot pussy, damning the consequences.

Michele was clearly also desperate for her own release, but thinking more clearly. She checked the room again over her shoulder, and lightened her grip, releasing my hard mast completely. I closed my eyes and took a deep breath as she let go, trying to regain some control over my desire for her. Stopping was not what either of us wanted, but it was necessary.

Then she did something I really didn't expect. While still facing me, she buttoned her jacket, but instead of standing and leaving, she spread her legs wide. I'd almost forgotten, her panty free pussy came into view as her skirt slid up her legs. She was soaked, her juices coated her smooth lips and upper thighs. I felt my own wetness against my thigh as my cock spilled more precum inside my pants.

She quickly moved her hand to her sex, slipping two fingers through her aching folds. She scooped her juices into her fingers and stuffed them into my mouth. My lust for her exploded as I tasted her sweet essence. I sucked her fingers and slipped my tongue over them wanting to taste every drop. My God she tasted sweet!

But sadly, her fingers pulled back as fast as they'd been stuffed into my mouth. At that point, she stood up, buttoned her jacket, and straightened her skirt. She put her hand on my shoulder and leaned down, her lips nearly tickling my ear.

Words left her lips softly, "Scott, I need you to devour my pussy. I need it every bit as bad as you did yesterday in the parking garage. I want your head between my legs until I come for you baby."

Another glob of precum escaped the tip, spreading itself around the head inside my pants. I was speechless and she knew it, Michele stood and I watched her ass in her skirt as she wiggled it back out of the room towards the conference. I sat alone, waiting for this painfully hard and desperate cock to soften and settle down enough so I could walk again without causing unwanted attention. It took longer than I thought, but I finally returned to the meeting, slipping into my seat next to Michele fifteen minutes after the session started. She giggled again as I sat down.

The afternoon was filled with working sessions that I unknowingly ended up running, as my experience in training provided insight others found valuable. It dragged on, all I wanted to do was devour Michele, and I was confident, she felt the same.

Through all the sessions and break out groups, Michele stayed near me. Being that close and not being able to touch her, kiss her, caress her arms, legs, heavy breasts, and round belly, was just painful. Each time our eyes met, I could see in her eyes, desire burned just as hot in her for me, as it did inside me for her. Tonight could not get here fast enough.

The last session wrapped up, and Michele and I walked across the lobby to the street. Needing some fresh air. The noise from the city during rush hour was almost deafening after being in the relative quiet of the hotel. She checked her phone and giggled, turning it towards me.

'Sure, bring a friend, as long as she is open-minded and can keep our party a secret.' The text read from Cassie.

"I guess we're a three-some tonight." I smiled looking at Michele.

"I guess so." She giggled and happily responded to Cassie's text. "Do you have Valerie's number?"

"I do," I pulled my phone and began a text message to her, copying the details and asking her to meet us in the lobby of Cassie's building.

The response came immediately, 'I'll be there, looking forward to seeing both of you.' I showed Michele, she smiled wide and gave me a hug. "I'm so excited!" She shared during our brief but genuine embrace.

The noise on the street of the city gave way to the calm and order of the hotel as we returned to our room. Earlier in the day, we'd have torn each other apart, but now, both of us were eagerly anticipating what the evening would bring. We decided to clean up and head out, if the party was what we thought, they're be plenty of exploration tonight. If not, we were just fine losing sleep tonight once we got home to take care of each other, and the desire we'd both been building since this morning.

I insisted we shower separately too, because I wanted a surprise when I saw her ready for tonight. Somehow, there was an increased arousal inside me when seeing a woman, thinking of undressing her, when I hadn't seen her get dressed. And today, had been nothing short of one arousing moment after another, so I asked her to continue through tonight.

I waited at the bar just off the hotel lobby for her. Dressed in a black suit and a white Oxford, no tie, black leather shoes, 'cocktail attire' I thought, shaking my head at Cassie's text with a smirk, 'open mind', still wasn't sure what she meant but smiling at the possibilities.

This place was thick with ambiance, dark wood, dim lighting, felt like it had been here a hundred years. The bar was more dimly lit, than the restaurant had been, another quiet place. Given the hotel was full of business travelers, strange, but welcomed. Being in a room with 400 people all day, I craved less overwhelming interactions, smaller, more intimate groups.

Watching her walk in was nothing short of breathtaking. My jaw dropped yet again today. Michele's blonde hair framed her face, hanging down to just below her shoulders. She wore a sleeveless blue and black skin tight dress, accentuating her beautiful curves. Her swollen breasts bouncing as she walked on top of her round, pregnant belly. The dress was so stretched, it was shorter than it had been last time I saw her in it a couple months ago. It now ended a little higher than mid-thigh, showing off her long legs that poured into strappy black 4 inch heels. I didn't see a hint of a bra strap or panty line, imagining her naked under this thin, skin tight fabric made me throb immediately, raising my need for her. I was absolutely obsessed with this beautiful woman walking towards me, beaming with bright eyes and a smile threatening to light up this dark bar.

I wanted to wrap my arms around her and kiss her passionately right there. I wanted to clutch her tight ass and let our tongues explore each other and pull her close, letting her know how hard she was making me. But, we still had to keep up professional appearances. It was nice to see the same desire in her eyes as she sat down next to me at the bar, where a tall glass of ice water already awaited her arrival.

We talked for a while, it was always easy for us to do that. Michele opened up about how things were at home, so did I. The last few months had been harder in many respects, but better in others since our first time together. It was like we were able to appreciate our spouses for who they were, not despise them for who they weren't. Those other needs we so desperately craved at times, had found a trusted partner to satisfy those with in each other. But as the weeks had rolled on, both of us, wondered if we'd ever see each other again. This week had confirmed that we would, and confirmed that the passion and desire both of us held for each other had not flickered out, if anything, it burned stronger than before.

Checking my watch, we needed to go, it was nearly 7:30. Thankfully Cassie's building wasn't far. Without thinking, I extended the crook of my arm, and Michele happily took it, smiling wide, as we headed for the valet stand.

Moments later we'd driven quickly to Cassie's place, and now nervous anticipation filled both of us as we stood in the lobby, awaiting Valerie's arrival. We'd decided to meet here to give us the opportunity to leave separately if necessary. We stood close, talking just over a whisper, my hand resting on the small of Michele's back. We still were unsure what tonight would bring.

The door to the parking garage swung open and I think both Michele and I caught our breath. Valerie strutted into the lobby, she wore tall, black, 5 inch heels. Her strong legs accentuated by a very short dress. Bright red, it stretched down only to her uppermost thighs, tight through the hips over her small waist and flaring out again as her large breasts sat high on her chest, stretched the material. Her dark hair, pulled up on the sides into a clip on top of her head and hung down the middle of her back behind her. Having seen her looking attractive but more professional than sexy over the past two days, tonight, she dripped with sexuality. She smiled wide as she approached us.

"You two look fantastic!" She said enthusiastically as she eye balled both of us, but paid special attention to Michele's body stuffed into her tight dress. Her eyes poured over Michele as mine had earlier.

"You look stunning yourself," I replied, my eyes roaming her curves on full display.

Valerie turned and now looked me over slowly, "I like what I see Scott, Michele is a very lucky girl."

The three of us turned and headed for the elevator to the penthouse. All three of us visibly excited for what tonight might bring.

The elevator doors opened to a short hallway, and those double doors swung open, Cassie stood, ushering us in. Another sight to behold.

Cassie's hair was long and pulled back into a neat ponytail high on the back of her head. She wore a black babydoll styled dress that made her breasts nearly spill out of the top. They jiggled with every small movement, making it impossible to keep eye contact with her. The dress was short and ended mid way to her knees. Her powerful thighs and calves flexed as walked, not clearly defined like Valerie's but bulkier, heavy with muscles that spent years working on a ranch. Cowboy boots completed her sexy look. A smiled beamed from her as we walked through the door.

"So glad you made it!" Her Texas twang shone through, she looked like she was a couple drinks into being more relaxed. The entry to her place was grand with high ceilings and beautiful finishes. She showed all of us into her dining room, seating for ten and floor to ceiling windows that looked out over Lake Michigan. 'A million dollar view' I thought to myself, both Michele and Valerie peering out the windows. I must have looked at Cassie with the wrong expression.

"I know what you're thinking, service wages and this place?" She smiled as she spoke.

"No I didn't-"

"It's okay babe, my daddy's cattle and oil money paid for this place years ago. He bought the whole top floor, and the pool above and turned it into a penthouse for our family. When I couldn't find the excitement on the ranch I was looking for, I moved here to this place," she explained.

"Cassie, I didn't mean to-" I started again to apologize.

"You stop that, everyone wonders." She stated flatly. "Now, let me explain something, remember my directions said 'open mind'? Well, I invited you because I saw you all over each other in my restaurant the other night and thought you might enjoy this. It's why I work at the restaurant, it gives me a chance to meet people, and invite them here for a good time. All the people upstairs by the pool, are in town staying at the JW right now, and before you ask, no, none of them are guests for the conference, I checked. One other couple lives in my building, they've been here before, and my boyfriend Colt, and me."

That Texas twang was so thick on certain syllables. We both listened carefully.

"Things are gonna get a little rowdy up there," she smirked, "and if it's not for you, you're welcome to go anytime, but if you want to stay, you have to follow my 3 rules."

Valerie spoke up, "rowdy?" She questioned.

"Yes baby, I mean real rowdy." Cassie chuckling as she answered.

Michele, Valerie, and I glanced at each other, and back at Cassie. We knew what she meant.

"Now, those 3 rules are: Number 1: Cell phones/cameras stay here on the table with your keys. Number 2: If someone asks you to do something and you don't want to, you say 'no thank you', and you respect others answers to you. Number 3: By all means...don't hold back, relax and enjoy yourselves!"

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.