Workplace Romance - Chicago Ch. 03

We drove along Lake Shore Drive about as far north as it would take us and it was almost sunset. We decided to head back the way we came and find a spot to enjoy the changing sky.

As we drove, it allowed me to think about just how fortunate I was today. How small the odds were that Michele and I had been randomly thrust back together on another out of town work trip. I was enjoying the company of this beautiful woman as she enjoyed being 'out of her shell' again with me.

It still surprised me that she could be married to someone who never appreciated her beauty. Never showed her how sexy she was or made her feel beautiful. Or even, made her feel like a woman and satisfy her. Then it occurred to me, I was in the same situation. Completely ignored by my spouse when it came to intimacy, and was ridiculed every time I tried to bring it up. We both loved our respective spouses for many other reasons, but unfortunately, in the intimacy and sex department, they had both inadvertently shoved Michele and I into each other's arms.

I was so good though to see her exploring again, pushing her boundaries. Trying things she 'never thought she'd do'. It was so exciting to see her test me. Our last trip had mostly been about me testing her, and bringing her out of that shell. But today, she was pushing me too....and I really enjoyed seeing her self confidence in her own sexuality. Her need to explore, be playful, and have fun, was exactly what I needed. We had broken down that barrier of exhibitionism last trip, and from what I'd seen today, she liked it, even craved it. That could make this trip very interesting.

Given that she was about to burst from pregnancy made it more arousing for me. I'd never been necessarily attracted sexually to pregnant women, it wasn't a 'fetish' if you will. Meaning, I didn't seek out women who were pregnant specifically. It wasn't that I found them unattractive at all, just had never been with a woman sexually who was pregnant. Over the last couple months, I may have taken a double take a few times at the grocery store or in a restaurant when a beautiful pregnant woman walked by. It made me think of Michele and take that second look at the unassuming woman nearby.

So this feeling that I'd come to love about her from our time together 2 months ago, was only stronger now. I found her incredibly arousing. I guessed even she was more aroused in this state. I'd heard of women becoming more sexually active when pregnant, but hadn't experienced it until Michele. Must have just made our chemistry that was already there, even stronger.

She played with her hair whipping in the wind with her right hand as her left found my leg again. She slid it up and down my thigh, squeezing now and again, making sure I knew that she was attracted to me. What a great feeling to be with someone who wanted to touch and be touched.

I looked over at her, I didn't know what she was thinking, but she was smiling, grinning ear to ear actually as the fading sunlight splashed her face and the wind rushed through her hair. Her right hand dropped and unconsciously rubbed circles on her round belly.

"Let's go out there!" She blurted out, as we came up on the turn off for Ohio Street Beach.

It was a tiny little piece of sand that offered a great view of some of the Chicago skyline and the lake, a great setting to watch the sunset. I quickly found a place to put the Porsche and we walked quickly, hand in hand, past Caffe Olivia and onto the sand.

The sand was just a bit warm to the touch still, but fading quickly as did the sunlight. The beach was deserted this late in the day, and we walked to a place furthest away from the road, where it was more peaceful. I sat down first, and offered her the spot in the sand between my legs and helped her awkwardly sit down. She must have been so uncomfortable all the time being 8 months pregnant, but she never complained. She seemed to enjoy being pregnant immensely, at least around me.

She sat back against me and leaned in, snuggling her head into my chest, as I wrapped my arms around her. We looked at the skyline and the beautiful lake, already the sky was turning to warmer colors at the daylight faded away below the horizon. The last glints of direct sunlight reflected off the windows of all the high rises, which were built right up to the shore.

The sunshine, reflecting from the glass created a shimmer over the tops of the small waves that was incredible to watch. She nuzzled her head deeper into my embrace, a soft moan escaped her lips, "this is nice," she said.

"Very." I agreed with her.

Had it not been for her draining my life force out not more than an hour ago, I would have already been caressing her with devilish intentions. Her silky blonde hair, her soft skin, those beautiful heavy globes of sensitive flesh and her large, round belly. Knowing she was still naked under her long skirt, her smooth sex, probably still wet and engorged from when I was going down on her earlier, and likely again from when she'd done the same to me.

I still couldn't believe how she'd just shown off in a very public place like that, and made a show of bringing me to orgasm. Sure we'd had some fun by the pool of our hotel months ago, but the number of prying eyes was limited and more calculated then. Even the parking garage had no witnesses, just the excited security guard watching us on video. But the park was much riskier and could have drawn a larger crowd.

However, at the moment my cock hung soft in my pants, sated, for now. Later was likely a different story, Michele and I had been playful today, with hands and mouths, but I hadn't been inside her yet, and didn't plan on going to bed until that happened. The touching At the moment was just for the sake of touching her, helping her feel safe and cared for in my embrace. Sliding my hands along her arms and thighs as she was curled up against me. I brushed her hair off her face that has slipped from her pony tail. She was beautiful.

We watched the sun sink lower behind the buildings. The changing light bounced off those buildings and the water as the sky turned from blue, to red. The sunset was something to see.

She nuzzled up a little higher, lifting her lips to my neck. She kissed me once, then opened her mouth and let her tongue trace a little circle inside her lips on my skin. She moaned when she was done.

"Baby, that felt so good." I told her.

She giggled and did it again. This time with more purpose, she knew what she was doing to start pushing my buttons. All the contentment I was feeling moments ago disappeared, as her touch began stirring my desire for her immediately.

"Keep that up, and everyone in the W Hotel is going to see you get fucked on this beach." I joked with her, pointing at the huge building just off the beach. "Let's not forget the folks eating at Olivia either."

"Maybe one of them will join us and bring us dessert." She laughed after her own comment.

I can only imagine the scene. A sexy idea for sure, but not without serious risks. When she'd pulled my cock out earlier on the plane, sure in public, but more controlled risk as we had a chance to see people before they saw us. One passenger had watched, thankfully Valerie had responded positively, well, let's be honest, her reaction wasn't just positive, it was encouraging, enabling even. But now, with 50 or so people in the restaurant and who knows how many in the buildings overlooking the beach, it was too much. All it would take is one person to ruin our fun.

She kissed my neck again, she slid her fingers around the back of my head and through my hair as she did. I felt myself begin to thicken in my pants again. Thoughts began to run wild as my libido took over again. But I needed to stay in control right now.

I gently turned her back to me and pressed her up against me again. Pulling her back into my embrace where should couldn't kiss my neck. I reached around her, holding her beautiful pregnant belly. My hands slid over the material of her blouse and opened a couple of buttons near the bottom, releasing her belly to the cooling evening air.

She moaned at my touch and squirmed a bit as she tried to get comfortable, pressing harder into my back. My hands slid in circles around her belly, then tracing the edges of her skirt as well as the bottom of her bra. Touching every inch of exposed skin. The sky continued to turn colors, darker now as the light faded, no more shimmering waves, just a dark expanse.

Her skin was soft to the touch, her belly tight, hard, and perfectly round. As I touched her belly, I could feel her relax, the weight of her body pressing more firmly into mine as her muscles gave in.

"Mmmmmm," she moaned. "My belly and breasts are so sore."

Her breasts are sore. Now all I wanted to do was satisfy her, I wanted to peel off her clothing and touch and lick her perfect breasts right here. But then we're back to getting arrested for having sex on the beach. But the ache inside me grew, I wanted her again, needed to feel more of her skin against mine. I looked back and forth over the beach, assuring myself that we were alone on the sand.

I slid my hands over her belly again, this time slipping up over her blouse and removing another button. Caressing the underside of her breasts from over her bra. My hands never stopped moving and the next time I came up near them, I unbuttoned the next one. More of her bra was exposed. Again, with one big sweeping circle over her belly and back to her chest, I ended up at her last button. I released it, her blouse fell off her swollen bra covered breasts to the side of her rib cage. My hands slid over her skin to the tops of her mounds, her flesh soft to the touch, I traced some of the veins in them I'd spotted earlier on the plane. So swollen from her pregnancy, already producing and storing milk. This left her with much larger boobs than she was used to, so swollen and sensitive.

She moaned again at my soft touch.

Her bra was white, the edges over her chest and the straps covered in soft lace. Satin on the inside of the cups to be soft against her sensitive skin. Supportive too, and pretty, for the soon to be mother. It was then I noticed the clasp between her breasts. Without thinking I moved my hands to it and opened it. Her bra snapped away quickly, each cup falling where her blouse had gone. This sprung both her heavy boobs free of the confines of her bra. They swung for a brief second before stiffening again in their perky state, her nipples were hard and pointing towards the darkening sky.

"Mmmmmmmmmm." She moaned as her pink nipples touched the cool air.

They were so beautiful. Much larger than I'd remembered, she was now either a very full C or D cup. Last time we were together, they were much smaller. A cups that would vibrate more than swing when she moved. But now bigger, and just as pretty. Her breasts still sat tight on her chest, large, heavy, they sloped gently and were topped with her medium sized pink nipples pointing skyward. I remember her nipples were smaller when we were together a couple months ago. Previously her areola had been the size of quarters, her nipples, like pencil erasers, now they were larger and stretching with her growing chest to contain the volume of milk within.

But her bra had been painfully inadequate at fitting their growing size. Red lines in her skin left marks where it was too tight. My fingers went to those lines and caressed them lightly. Tracing them on her soft skin, across and underneath her heavy chest. I cupped both her breasts, gently putting pressure on them without squeezing too hard. I gently slipped my palm over her nipples and they stiffened to my touch. They sat right on the tips of her perky breasts, begging to be sucked.

I pulled my eyes from her perfect breasts and looked at her face. Her eyes were closed, her lips parted, breathing slowly and deeply. I wanted to kiss her, but we'd be having sex in no time, and I was trying to retain some level of control.

Michele's lips parted again as she exhaled, as little whimper followed. All I wanted to do was nuzzle the engorged head of my stiffening mast against her slick lips between her legs. Feel her clit stiffen under the weight of my cock.

I slid my hands back down and around her belly, over her breasts. I made circles on her skin, gently caressing her entire chest and belly over and over. She moaned again through her parted lips. I traced my fingers lightly over her engorged and erect pink flesh. Her nipples seemed to tighten further, even her areola swelled, making her pink nipples look puffy, aching for more.

My cock began throbbing with more urgency in my pants. Surely she could feel it thumping against her back, getting longer and thicker as I caressed her skin. But with how relaxed she looked, I wasn't sure if she wanted to do anything about it. I was still nervous about people in the hotel and restaurant. What if someone saw us? But maybe giving a pregnant woman a 'massage' would be more easily explainable. We definitely couldn't take it further here.

A difficult decision given how she currently sat, leaning against me with her achingly hard nipples pointing skyward. My cock thumped against her back. The carnal need I felt for her again today would have to wait to be satisfied. I forced my own self control. I focused on just caressing her breasts and belly as I slid my hand slowly over her, trying to be sensual, but not sexual. It was more difficult than I could have imagined. I touched her until long after the sun had set and we sat in darkness.

We needed to get moving, so I kissed her forehead, slid my hands to her bra, her lips made a pouty expression as I struggled to reclasp her bra over her swollen flesh. Once done, I reached for her shirt and helped her button up again. She sleepily and begrudgingly acknowledged our necessary relocation. We stood, and walked slowly to the car hand in hand again.

"That was really nice Scott," she said with a grin and squeezing my hand. "Thank you."

I just smiled and opened her door, allowing her to slip down into the seat, shut her door and moved around quickly to get us moving. We still had a hotel to check in to, and I was starting to feel hungry for real food.

We drove quickly the few blocks to the JW Marriott, crossing the Chicago River again, passing City Hall, and finally turning into the valet at the main entrance to the JW, just a block from the Willis Tower which stood, dwarfing the surrounding buildings.

Checking in, we asked if it was possible to have adjoining rooms, and they were able to accommodate us. They also had rooms on the west side of the building facing the Willis Tower. We quickly rode the elevator up and entered our own rooms separately, but immediately dropping our bags and unlocking the adjoining door between them and creating a huge suite for just the two of us!

"This is awesome!" Michele said excitedly, as we both walked toward the window. We were on the top floor of the JW, floor 12 of the building's 21 stories, and trying to see the top of the tower at 108 stories from a block away practically required us to lay on the floor against the windows and look skyward. But a view of one of the tallest buildings in the world, was pretty cool.

"Ok, what's first, shower, or dinner?" I asked playfully.

"You're asking a pregnant girl if she wants to eat?" She retorted with a smirk.

"Dinner it is," I started, "let's unpack quickly and go eat."

She nodded, gave me a quick kiss and we separated for a few moments to hang suits in closets and place bathroom things where they were needed. I put my empty bag away in the closet and waiting for Michele to finish as well.

"Let's go!" She said excitedly from the doorway of our adjoining rooms, her eyes lit up bright as she did.

I didn't need more encouragement and we headed downstairs to the restaurant. This was a work trip, and we still weren't sure on all the attendees, so we needed to be on our best behavior. Or at least, 'better work appropriate' behavior. We didn't hold hands on the way down the hallway, but while alone in the elevator, I did manage to pull her close and steal a brief kiss. Her soft lips were irresistible, and she giggled as I let her go, just before the door opened.

A busy lobby as guests arrived to check in themselves, likely many of them attending the conference that was to begin tomorrow in one of the ballrooms of this hotel, just upstairs. We made our way to their main restaurant. The head chef had been highly touted as one of the up and coming culinary wizards in Chicago.

The last time Michele and I had dined in a hotel restaurant, we ended up having sex with the hostess as well as the waiter by that hotel's pool. I remembered how the waiter's thick cock had stretched Michele's pink folds, and how eager she'd been to devour the hostess as I'd entered that college girl's ass.

Seeing how this hostess seated us, it did not seem that it would be a repeat performance. This girl had paid no attention to Michele, only me, and even then, the young brunette was 'all-business' and seated us at a table for two, over on one side of the restaurant. Away from many other guests that were already dining. Once seated she moved on quickly and unremarkably back to her stand near the entrance.

The booth was half a circle, Michele had been seated at on edge, and I sat on the other and scooted around to the back, or middle, as it were to sit next to her. This way two of our knees could touch but we both still looked as if we were just waiting for a third person to arrive.

The restaurant was dimly lit, only pendant lights over illuminated the tables. The lights from the ceiling were turned down low. Only specific lighting illuminated some artwork on the walls and dividers around the restaurant. The walls between tables were higher for privacy, but low enough for me to see across the room and note that there were not many tables occupying this end of the restaurant.

I looked over at my date for the evening already eyeing the menu like a famished lion. We hadn't eaten anything since the snacks on the plane, and I too was hungry. Still in her pinstriped blouse that I'd opened a couple of times today, now barely concealing her heavy globes. Her flowing white skirt, that had earlier been hiked up to her hips as I tasted her sweet pussy in the parking garage, now slipped all the way down to her ankles. Those cute little feet in her white, strapped sandals.

It occurred to me that I still had her panties in my pocket. The same little white thong she'd removed on the airplane after I'd made her cum so hard she'd soaked them. I didn't think she had time to put a new pair on in the room, which meant this beauty next to me, eyeing the menu, had her perfectly smooth pussy just underneath the thin fabric of her skirt. Just the thought of that made me throb again. Visions of picking her up and setting her on the table in front of me, spreading her legs wide and devouring her pink little pussy rushed through my head, an absurd thought, but a sexy one.

The waitress seemed to appear out of no where, someplace in the relative darkness not illuminated by our table light. Her white name tag stood out in stark contrast to her black pants and black button down shirt, it read "Cassandra".

"I'll be taking care of you," she said confidently with an accent that clearly placed her from Texas, "what can we get started for you?"

"What appetizer gets here the fastest?" I responded smirking and look at Michele who giggled, knowing why I was asking. Her boobs jiggled on top of her pregnant belly whenever she did that, and I couldn't take my eyes off her.

"Well, breadsticks are pretty fast, our calamari is pretty quick too...." She kept thinking.

I stopped her thought, "yes, both please. And when you get a chance, just two ice waters to drink."