Workplace Romance – Chicago Ch. 05

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Big Tits


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

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!


We pulled into the valet of the JW with Valerie still right behind us. Traffic had been light on a weekday evening, and made the drive back from Cassie’s party smooth and enjoyable.

The valet helped Michele out of the Porsche as I walked around to meet her. We waited for Valerie to do the same. Michele touched my arm again, and I felt tingles throughout my arm as she did, a warmth wash over me. She always knew just how to make me feel wanted.

She must have remembered that we needed to be on our best behavior again. No longer the freedom we had this evening, our roof top pool orgy required less professionalism. She drew her hand back, but still stayed close.

Valerie approached, tugging her very short dress down as not to expose her ample butt cheeks to anyone. This hadn’t been professional attire at all, pure sex attire was more like it, and she looked amazing.

“I don’t know about you, but after the day I’ve had, I need a drink!” She announced to us.

“I agree,” I responded. Knowing that Michele would have water because of her pregnancy and I’d join her out of respect. But I wasn’t going to let Valerie drink alone. Not after what we just did together, someplace down deep I wanted to make sure she was okay.

We entered the hotel, it wasn’t late, barely 10:00, so we headed the the dark bar that Michele and I were in just before the party. It was almost entirely empty, we found a half round booth near the back of the bar, dimly lit with an overhead lamp that shown on the table. Darkness all around provided some privacy, or at least ‘perceived-privacy’.

Drinks arrived, two waters for Michele and I and a Grasshopper for Valerie, we were quiet for a few moments, the three of us lost in thought and processing over what we were just a part of. Staring into those freshly poured beverages on the table, glasses already sweating from the humidity.

“A toast,” I started, “to new friends, and new experiences!”

“To happiness!” Michele quipped.

“To all of that,” Valerie agreed, “and to me sorting all this craziness in my head!”

She smirked but her eyes looked worried as we all clinked glasses. I’d nearly forgotten that this was her first time having a sexual experience outside of her marriage. Michele and I were so comfortable together, and we’d been with others on that first week of exploration, so it wasn’t out of the ordinary for us. But Valerie looked a little like she might be freaking out a bit.

She smiled wide at both of us, “Damn you two are sexy together. First, seeing you on the plane, and now tonight. The two of you just ooze passion for each other.”

“Thank you Valerie,” Michele responded, “Scott really brought me out of my shell. Just a couple months ago, I was an unhappy sexually repressed woman, now, I feel like I can do anything, all thanks to meeting this guy.” She squeezed my arm, and winked at me.

“I still can’t believe you went down in him in front of me in the plane. My God that was sexy. You both turn me on so much.” Valerie shared.

My cock thickened under the table, I felt it pulse at the thought of how Michele had devoured me on the airplane in our first class seats. Looking over and discovering Valerie watching us intently, it was too vivid a memory. My mast stiffened further. Michele must have noticed my expression, she reached over, underneath the table, and gave it a playful squeeze.

We glanced at each other. Smirking, both of us thinking the same thing. That flight was a hot moment we’d both remember forever.

Quietness overtook the table again. Michele and I looked at each other and over at Valerie. Even in the relative darkness, I could see tears welling in Valerie’s eyes, she lowered to head to try and cover her reaction.

“I’m sorry,” she started to begin to sob quietly. Her eyes overflowed and tears began down her cheeks.

“Valerie,” I returned, handing her my cloth napkin to wipe her eyes. “Please don’t apologize to us, We both know tonight was a lot to process.”

“No, it’s just…” she stopped herself, wiping her eyes, and clearing her throat before continuing. “I was so happy tonight for the first time in as along as I can remember. You both made me feel beautiful, and sexy, and sensual. I let go of all my fears and hang ups about my body with you. I barely know you. What does that say about me? I can’t be happy with my husband, but I can be happy being naked with a bunch of strangers!”

Tonight had been sexually fun, but lacked the passion and intensity gaziantep eskort that Michele and I had our first time together. Because Michele and I were further along in our journey, it felt okay for us. But I just realized for Valerie, it may have been lacking that emotional connection she needed with a lover on her first time stepping out. She hadn’t really ‘fully’ cheated on her husband tonight I suppose, she made Michele orgasm with her fingers, tasted my cum from Michele’s lips, and gripped that tree trunk of that Texan’s huge cock as she assisted the couple having sex in front of everyone. But this was clearly weighing heavily on her, we’d momentarily forgotten about the passion and intimate lovemaking Michele and I had shared mixed with the lustful, uninhibited sex that we’d first experienced together when we became each other’s first ‘affair’ months ago.

“We aren’t strangers Valerie.” Michele pleaded.

She looked up, “you’re right, but we haven’t known each other very long.”

“Valerie, you’re right about something here, we haven’t known each other long, and I think I can speak for both Michele and I that we’d love to hear more about you, about your marriage, what’s your story?”

Valerie looked at both of us, composing herself further as she dabbed the last tears from her eyes. She was thinking about where to start.

“Just start at the beginning Valerie.” I assumed.

“Okay, well, she paused, taking a sip of her minty chocolate beverage and remaining quiet for a moment, thinking.

Michele and I took sips of our waters and waited to hear what she had to say.

“My God, I have done this for a living, asking people to tell me stories and share their feelings, but this is the first time I’ve had to do it!” She smiled and chuckled. “Ok, here goes…”

She took another sip of her drink, cleared her throat, and began.

“I met my husband about 16 years ago, we worked at the same clinic just after college. We’d had a whirlwind of a romance. He had been constantly flirting with me at work, and it wasn’t long before we started dating. I can remember melting when we kissed, and his body feeling a similar connection, passion seemed to overflow from us when we were together. The most exciting thing for me was the sex was constant. We’d sneak off to an unoccupied office sometimes for lunch and do it on that Doctor’s desk, or the patient couch. Or we’d go out to eat at a restaurant and have sex in the car before returning to work. It was incredible, and it wasn’t just the sex, we talked and listened to each other, he really made me feel loved all the time.”

She continued, “Before him, I was always a very conservative person. I never dated much, always focused on school. Sex was something I enjoyed, but I never really came out of my shell until him. After we’d been together a few months, he started pushing my boundaries, and I loved it! We explored a lot together, oral sex in semi-public places, light bondage, I can remember sucking him off from under the desk secretly while he was on a phone call with our CEO. We got married after about a year of dating, the relationship kept getting better and so did the sex. Damn I loved fucking him!”

Michele and I exchanged knowing smirks and sipped our water, now intently watching Valerie again. My cock stirred to life inside my pants, I knew that Michele’s smooth lips were getting slippery between her thighs with Valerie recanting her past sexual exploits.

“You see!” Valerie exclaimed, “that’s what I mean. Two people communicating with a glance, or a soft touch, because they know each other so well. Just like you just did, I miss that connection.”

“So did we until we found each other,” Michele beamed looked at me with a smile.

“I can see that. It’s beautiful what you two have, I still can’t believe you found this while being married to other people, you’re so lucky.”

We smiled, I said, “please continue your story Valerie.”

“Well, like I was saying, the sex was incredibly passionate, and intimate. I realized my physical love language and came out of my shell. We loved pleasing each other, and it was fantastic. And then, all that changed on one day, and I remember that moment completely. It was the day I told him I was pregnant.”

She paused, gathering herself before continuing. “He just looked at me different after that, the sex completely stopped, that moment. He wouldn’t touch me, not even in a non sexual way. We still kissed now and again, but even that stopped one day. I went that entire first pregnancy with really no meaningful contact. No way to express my love or feel loved. By the time our oldest was born, it was like we were just roommates that slept in the same bed.”

“Awful,” Michele agreed, “I had a similar experience over the past 8 months. I’m sorry Valerie, please continue.”

Valerie smiled at her shared kinship with Michele, and pressed on. “He is a great father, eskort gaziantep helped with everything, diaper changes, feedings, whatever I needed, except the love I needed to feel. We didn’t have sex at all. I tried to initiate it nearly every day, playfully licking his morning hard-on, or pouncing on him while naked, he’d push me away or have some excuse. Eventually I stopped trying, couldn’t deal with the rejection. It was awful, he wouldn’t kiss me, or even look at me. I blamed myself, how I looked, I thought the pregnancy had destroyed my once super-fit body. I felt like I was ugly.”

Her face became visibly sad, but she continued.

“One day, for our anniversary I decided I was going to change things for the better. I went out and bought some really pretty lingerie, arranged for a babysitter for the weekend, and made a reservation at a resort hotel. We were going to have a little getaway to rekindle what we’d lost. I convinced myself, I’d remind him what a good lover I could be. Well, what a disaster that turned out to be. He spent the weekend avoiding contact with me, we hardly spoke, we did have sex, once. I remember how disgusted he looked while he was inside me. For the first time I remember being thankful it was over quick. He came, I didn’t. Wouldn’t you know it? I got pregnant again from that night. First time having sex since getting pregnant the first time, and I’m pregnant again. I stalled telling him in the hopes we’d fix what was broken, but it didn’t get better. When I did tell him, all my hope was lost, he returned to ignoring me, he became so distant.”

“I’m so sorry, Valerie.” I started, “that must have felt so awful and lonely. I know how that feels.”

“Thank you,” she continued, “so now with two kids, he’s still a great dad, but there’s no passion for me at all. I started wondering if he’d found someone else, but he’s easy to keep track of, and I learned quickly, it wasn’t the case. So I blamed myself even more.”

She went on, “I started working out again, lost all the baby weight and got back in shape. When I did, I never quite looked the same. Not quite back to my fitness competition shape.”

“You look amazing!” I said a little too enthusiastically.

She smiled, “thank you, I work really hard. Back then, I was in good shape, but not what you see now.”

I nodded in understanding.

“One day I got up the courage to try and seduce him again, I stood in front of him, fresh out of the shower, completely naked. I’d just shaven everything smooth just the way I knew he used to like it. I stood there, totally naked, water beading off my body. He told me my tits we sagging, and walked out of the bedroom. I was crushed, the pain of being rejected while so vulnerable was unbearable. So, within a month, I had them done. Perky again, I thought he’d be happy, but not the case. He found something else to criticize, my lips, so I had them enhanced, then he said my nose was too big, I had that reduced. Each time I thought he’d find interest again. But each time, nothing.”

Michele and I shook our heads in mutual frustration and understanding, we’d both been there in our own lives. But Valerie had gone to extremes we hadn’t considered to change her body for her husband.

“I masturbated constantly, to fulfill my own deep need for release of all the tension. Everywhere, in the shower, in the car on my way to work, I even secretly rubbed myself at work once during a video conference!”

“Wow!” Michele exclaimed. “That’s hot!”

Valerie smiled for a moment, and continued, “my youngest was three before my husband and I had sex again one night. Afterward he told me my pussy wasn’t pretty and didn’t feel as tight as I used to. So I had vaginoplasty to tighten things up again, and I had labiaplasty to make ‘her’ pretty again. I even went through laser hair removal of everything down there so I’d always be perfectly smooth for him. He knew about the surgeries, obviously, but again, zero reaction, he didn’t even want to see it when I had healed. We haven’t had sex since that night over seven years ago.”

“It’s perfect, I said quietly” remembering the first time she showed us on the plane. The last few moments answering questions in my head of just how she got her pussy to look so perfect, so smooth, tight, and perfectly pink.

“Yes it is,” Michele agreed quickly.

Valerie blushed a little, “thank you both, you’re the first people to say so,” she paused, “you’re the first people to see it since the surgery when I pulled down my pants on the plane….still can’t believe what possessed me to do that! I guess seeing your passion together made me want some of what you two had.”

“So,” she continued, “after that, I went back to masturbating again. And after a little bit of exploration one time with my finger, I discovered how tight I was. It felt like it did when I was an inexperienced thirteen year old exploring myself in my bedroom. I decided that gaziantep bayan eskort the next person I chose to have sex with was going to have a surprise. A newly virginal pussy, that’s not been penetrated by anything.”

I nearly spit out my drink. “Hold on, you haven’t even slid a finger inside yourself for real? I thought you were joking earlier.”

“No, I haven’t had sex in over 7 years, not even so much as my own fingers or a toy inside me. I didn’t think it would be this long, not finding anyone else. I’ve been so busy with work that I kind of lost interest in the search.”

“Oh my God Valerie,” I responded, quietly being turned on, my cock stirring again under the table. “You have incredible discipline. I could not wait that long without losing my mind.”

“I used to think that too,” she continued, “it hasn’t been easy, I really miss connecting with someone. Until you that is, both of you. I’ve never felt anything like this before. I was so excited seeing you please her on the plane, and then when she fished your gorgeous cock out and went down on you…..I found myself not just wanting you Scott, but both of you. Obviously I want to touch your throbbing cock and feel you inside me. I want you to be the first inside my tight pussy. But I also wanted to feel Michele’s beautiful belly, touch her pussy, and make her feel sexy. Being able to explore some of her today, made me feel more like a woman than I have in years.”

Michele blushed, just a couple of hours ago, Valerie has been latched onto her breast, slipping her fingers through her folds in the pool in a joint effort with the party host. They had both made Michele come right in front of me, and quite a few other onlookers.

After not touching another person for years, I underestimated the impact that must have had on Valerie. In the pool, when Michele leaned over and kissed her with a mouthful of my cum, she had orgasmed instantly while rubbing her pearl. It was sexy for sure, but I didn’t understand the magnitude of that moment until now for Valerie.

Valerie looked less upset now, she stared at her empty glass, as the images of tonight flooded our minds. My cock throbbed again, beginning to ache. I felt a small hand reach over and caress it over my pants, Michele, always alert to my needs. Valerie was lost in thought again, oblivious to Michele’s playfulness.

“Valerie,” Michele started, not removing her hand as she spoke. “My husband has no interest in me either, it brought me to a really dark place. When Scott and I met a couple months ago, we only spent a week together.” She smiled at me, and playfully stroked and squeezed my cock, “but it was the most incredible week of my life. I went through a journey of personal discovery I didn’t expect. I found myself, I found a passion inside I didn’t know I still had. All because he took his time with me and pushed me to explore those feelings.”

She squeezed my cock hard as she finished as if to emphasize the importance of what she was saying. I throbbed hard in response, it was now at a painful angle stuffed down the leg of my pants. Her small hand felt both amazing and agonizing.

Michele continued, “if anything, it made me a better wife, I no longer despised my husband for his lack of attention toward me. I no longer needed it, I felt, for the first time in a long time, empowered. No longer constantly rejected and ridiculed, I could focus on work and let him do his thing. I didn’t resent him, partially because I couldn’t stop thinking of how Scott had fulfilled those needs, but partially because I just felt stronger too.”

“I need to find someone like Scott.” Valerie said, just as the bartender brought us another round of water.

“She’s going to need another drink too,” I stated to him. Valerie just smiled.

The bartender disappeared to make her drink. Michele spoke up again, “you do need someone like Scott,” she squeezed hard, causing me to gasp, “but he’s one of a kind.” There was a long pause, Valerie stirring her straw in an empty glass.

Michele looked at me and back to Valerie, “Maybe I can loan him to you?” She gave me that devilish grin as I locked eyes on her. I looked at her a little panicked as she released my stiff member and smiled more broadly as Valerie looked across the table at her incredulously.

“Wait, what?” Was all Valerie said in response.

“Scott,” Michele started, “is an incredible lover, and I’d be willing to share him with you. I want you to experience what he’s done for me.”

“No, no, I couldn’t, I’d ruin what you two have, I need to find my own partner.” She adamantly retorted.

“Valerie, listen to me,” Michele’s tone became hushed as she leaned into the table towards us. “I’m confident in what he and I have, and if we can help you find that connection, rediscover that important part of you, I want to do that. I think Scott would agree.”

I smiled, trying to process what she just said. She and I had talked a lot, but hearing her profess how her life had changed for the better, made it real. I’d felt the same way. Now she was adamant about my ability to do the same for Valerie. It might be too much. I was really attracted to Valerie, but could I be as passionate a lover for her? It does take two people for that level of intimacy, would Valerie and I connect that deeply?

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