Bryan's Roadtrip Pt. 01

One of my favorite places to visit is Chicago. Since becoming self-employed in the wine business, I try to visit the windy city twice a year. A fantastic food town, Chicago has great museums, restaurants, live theatre, and my lifelong friend from high school and college, Terry. And although my wife of 30 years has warmed up to Terry, she is never thrilled when I announce that I am heading off to Chicago to sell wine and see him. Perhaps it's Terry's reputation for being a perpetual bachelor, or maybe it was the time he came out to visit us during our first child's baptism, bringing a date who frankly was significantly younger than us? In any event, I am looking forward to spending a long weekend with him since our schedules have not seemed to line-up in almost two years. Convenient to downtown and the L, Terry invited me to spend the weekend at his place. He owns a nice 3-bedroom condo that takes up the entire floor and has its own elevator stop. It was with positive anticipation of a nice hot shower and a visit to Gibsons for a stiff Manhattan "up" and a bone-in grass fed rib-eye that I departed my Uber in front of Terry's.

"Good evening" I said to the doorman, "can you buzz me up to the 10^th floor please? I should be on your list, Bryan Johnson to see Terry Albright?" The doorman, whose name was Hal, from the name embroidered on his doorman jacket, gave out a small chuckle and said, "my pleasure" and then added "Terry must be throwing one heck of a party tonight since you appear to be prepared to stay all night."

Perhaps it was the expression on my face, not quite sure, but then Hal added, "I've been buzzing folks up all evening, and you've actually got what looks like an overnight bag." and at that, the elevator doors opened, and I bid my thanks, as I stepped into the small chamber. Great... ugh... a party, it was going on 7:00pm and I really wanted a hot shower, which I now guessed will need to wait. That positive anticipation I felt down at street level had been replaced with trepidation on what I might be walking into. Terry does have a reputation...

Before I knew it, doors were open, and I was out onto a hallway. To my right, I could hear smooth jazz and some laughter and voices coming out of the living room. To my left, my sanctuary, the guest bedroom, and bathroom. Maybe I could slip unnoticed down the hall and get that shower in before anyone was the wiser. But before I had a chance to move in either direction, I heard my name booming down the hallway from the living room. "Bryan my boy, welcome back to Chicago! It's been ages!!!" and the next thing you know, I'm receiving a bear hug from my old friend. "Come, let me introduce you to my guests! I figured after a day of travel you'd want to just hang out here and that gave me an idea to throw a little party!"

Abandoning my valise and laptop bag in the hallway, Terry took me by the arm into the living room to meet his friends. There appeared to be four couples, but on first glance, it was unclear to me who would have been Terry's girlfriend. He had mentioned over the phone that I'd get to meet her on this trip, but everyone in the room seemed to be coupled up. Perhaps she was in the powder room I thought? "Hey everyone, this is Bryan, one of my oldest and dearest friends"

The room erupted with "HI BRYAN" Terry then asked, "what would you like to drink my friend?"

"How about a Scotch over a couple of rocks and if you wouldn't mind, I would really like to use your facilities to clean off a little of my travel dust before making all of the rounds, OK?"

"You go guy..." was Terry's response. So much for a shower I thought. After dropping my bags in the guest room and using the facilities to wash up, I returned to the party and was handed my drink by Terry who then again took me by the arm and began making introductions. As we made our rounds to the folks in the room, I quickly learned who was paired with whom and at this count, two of the couples were straight and married with kids and one was a gay couple whose names were Mark and Dave and lived in the building on the floor below.

It was now obvious that Terry was saving the best for last. "I have one more set of introductions." Terry said with a very large smile on his face, as we started walking towards two rather tall woman, with their backs turned toward us, looking out one of the expansive windows facing the city. They appeared to be having a serious conversation as they faced each other. One of these women was blonde, with shoulder length straight hair wearing a little black dress that showed off a very tight derriere and very toned and tanned legs. If I had to guess, this was Terry's girlfriend, given his attraction to tall blondes. As Terry came up to her, they appeared to be about the same height, but she was also wearing a pair of black stilettos, so my guess was that without shoes, she was probably around 5'10", still tall, and a good match for Terry who was 6'1".

The other woman, a brunette with short hair, was wearing a stunning red dress that was open in the back, complimenting her backbone and a tasteful gold neckless. She also appeared to be tall, wearing heals that weren't as spikey as her friends, I'd say she was also about 5"11". Her figured showed off someone who was in good shape, very tight rear with very toned legs.

Interrupting their conversation, Terry said, "Excuse me ladies," and they stopped what appeared to be an impassioned discussion and turned towards us, "This is Bryan and I'd like to introduce you to my girlfriend Monica and her close friend Debra. I have already told them ALL about you!" Terry added with a bit of a laugh and exited to likely get another round of drinks.

"Hello, Nice to meet you both" was all I struggled to say after both women faced me with gorgeous smiles. My first guess was accurate. Monica was blonde and Terry's girlfriend. She had piercing blue eyes, large DD breasts with ample cleavage showing accentuated by the cut of her little black dress.

Debra was equally stunning with green eyes, her gold neckless which seemed to only draw my eyes down to her more modest cleavage than Monica's. Her red dress was only slightly more conservative than Monica's, but you could also tell that her waste and hips were smaller as were her medium sized breasts, likely a C cup. What tantalized me most though was the sheer fabric of Debra's dress. I'm certain she was wearing a bra, but it too must have been quite sheer since I could just make out the shape of her nipples underneath. Between the smile on her face, and how she looked in this red dress, I could feel stirrings of my own beneath my trousers. All in all, both women were stunning, and their smiles and good looks only made me feel more uncomfortable as I tried to muster something to say.

In my profession, I'm used to working a room when selling wine, but this seemed to be slightly different. If I didn't know better, I was being setup by Terry and his girlfriend Monica, but why? Terry knows I'm married and although I've been unhappy for many years, I've never really hinted much about wanting to stray and wander. However, I've also always been good about sizing things up quickly and upon my first assessment glance of Debra, she was at least wearing a wedding band like me. OK, relax and breath I told myself...

Monica breaks the ice with "So Terry tells us that you're a winemaker from California?"

"Yes, I live and work in Sonoma County, about an hour north of San Francisco. Have you ever been there?" Monica first responds, "sure have, many times in fact. I just love Napa... "

Inside I cringe -- there has always been a strong rivalry between Napa and Sonoma Counties. They are very different places and sadly, most people only associate our 'wine country' with Napa. I respond, "what about you Debra?"

"Call me Deb, and yes, several times with my husband Jack. I love the Russian River Valley. It's closer to the coast than Napa Valley is, and generally much cooler. In fact, I've always been more of a fan of Sonoma County wines over the wines made in Napa."

One point for Deb as we start to make small talk. Suddenly a gong can be herd, interrupting our conversation as Terry announces that dinner is about to be served and to take our seat at his massive dining room table for dinner. For the first time since arriving, and not getting my hot shower, I can see that this evening is starting to look up.

As Terry started plating dinner, Monica directed everyone to their seats. I was placed at the head of the table with Dave and Mark to my immediate left, Diane and Steve next to them, Terry across at the other head position with Monica to his left and that left Anne and George in the middle and Debra to my right.

I figured this will be some fun dinner conversation. A nicely prepared pork chop with mushroom risotto and some rainbow chard was served along with one of my Pinot Noirs. Since college, Terry and I have always competed in the kitchen. He's an awesome home chef and somewhere buried inside his inner self, probably pined to be a professional chef. Instead, he became a 'VC guy' and has the income I wished I would have with a pretty good lifestyle, while at the Debe time he wishes he had the freedom I had. If he only knew. The good thing about his situation is a reliable income and that he's an awesome patron of my winery!

The food was delicious and as the evening progressed, Dave engaged me in what it was like to own a winery. He was a kept man. His husband Mark worked with Terry at the Debe VC firm in town and in fact it was Mark who introduced Terry to the realtor of his condo. So as Dave peppered me with questions, I kept a side eye on Deb as she talked to Anne about the trials and tribulations of raising a 'teener'.

Perhaps it was the alcohol, or the good food that always leads to some fatigue, but I could have sworn that I felt Deb's foot rubbing my leg. In any event, at some point during the tiramisu, I asked Deb about herself, since she already knew much about me from Terry and Monica. "I'm married, no kids thankfully, and an art professor at UofIUC." my response, "Champaign / Urbana? -- so you don't live here in Chicago?" "Oh no" she said, "I'm just up for a long weekend with Monica. We are old college buddies and I've found that even my husband prefers me to come up her to Chicago as much as I can."

I temporarily ignored the last part of her reply and responded, "So what is your art focus, I mean, what did you write your doctorate on?"

She responded with "The Impressionists, or more importantly, the impact and bias of the Impressionist movement. It's one reason why I love being so close to Chicago, because of the Art Institute and their collection of some of the best Impressionist works."

I was impressed, and perhaps a fun connection because I truly love these works. She continued, "Are you familiar with these artists?" I said "of course, these are some of my favorites." "Really?" she said, continuing "Who is your favorite? Monet, Renoir, Pitre, Caillebotte, Morisot, Magritte, Manet, Cassatt, Hopper?"

I could smell a test a mile away... but where were my traps? Hopper was a give me, since I loved his work and he was an American painter... but think, where were my other traps? "You say you have a doctorate and your focus is on Impressionism, sorry, Hopper doesn't belong to this list!" "OK, you caught me... it's a game I like to play when someone says that they are familiar with the impressionists. It's fun to see when someone is BS'ng me, or not... so can you tell me who else shouldn't be on this list smarty pants?"

With a smile on her face, I can now tell it was a total set-up and the challenge is on... "the other name that I immediately recognize is the surrealist Rene Magritte!"

"I'm impressed, ok so you kind of know who the impressionists are, but is there anyone else from the list of names that I mentioned who shouldn't belong on this list?"

"Can you repeat the remaining list again?" I ask, so she does, this time excluding the two names I had already called out. To my delight I recognized something that I didn't recognize as an artist's name at all. "Oh, ok, there is just one more name and it's the name of our host..." I say, leaving that hanging while watching her face trying to read mine.

"Ne pensez-vous pas que notre hôte est le Pitre? Oui?" In French I ask, if she thought our host was the clown, since the only name I didn't recognize was 'Pitre' or clown.

"Tres bien, tu parles francais?" she asks.

"Non, un petite parl" which I know only means 'a little talk' but tell that to someone in the south of France who is debating 'pain au chocolate' vs. 'chocolatine'. I love the French! And at this moment, I now know I felt a foot rubbing my ankle and I looked directly at Deb who gave me a little wink and a wicked smile.

Dessert had been served and the evening was drawing to a close. Folks started to get up to leave the table and at a quick glance of my watch, I could see it was well after 10:30pm. After a day of travel, I could say I was a bit tuckered out, but I was happy to enjoy the company I was in. As the last guest left, leaving just the four of us to finish the clean-up tasks, Terry looks at me and says, "hey buddy, would you mind starting the dishwasher? I have something I need to show Monica..." and before I knew it, he and Monica disappeared to his bedroom, leaving Deb and I alone in the kitchen.

"Got to laugh, leave it up to Terry to put his guests to work, cleaning up after HIS dinner party." I said.

Deb was a good sport. We were standing next to each other washing and drying and then all of a sudden, she grabbed the last plate from me before I was ready to hand it over and said, "give it here, I'm done washing dishes and want to dry my last plate!"

the aggressiveness caught me off guard and at that, she also flicked her towel at me while grabbing the plate. I let go of course, and with plate in hand and another off centered playful swat of the towel, she lost her balance. During this swing, she had been leaning towards me, so of course, she only had one direction to fall was towards me. I quickly reached out to catch her, only to find myself with one hand on her right breast and the other on her left hip. You could hear a pin drop, all silence as I held her for a few seconds that seemed like minutes.

For the short time my hand was cupping her breast, I could feel the nipple underneath starting to swell, leaving no doubt that the fabric of her dress and bra was extremely sheer. She was also now close enough for me to smell the scent of a perfume under her ear. She must have modestly applied some when she last visited the power room, since this was the first time that I smelled this scent, and I have an extremely sensitive olfactory.

As she gained her balance and composure, our faces were only inches apart and she was looking directly into my eyes. The look was not one of surprise as would be expected, but more playful and almost a look of lust, which caught me off guard. I still had one hand resting on her hip and decided to take a chance that could end up getting me slapped, or better, rewarded. Without asking, I proceeded to pull her in close and planted a delicate kiss on her lips. After pulling back enough to see her eyes and face, and judge her expression, I could tell there was no protest. Within an instant, I could feel her body press into my own with forward motion. The sound of a plate, the one she had pulled out of my hand, dropping to the wood countertop behind me. With her weight adjusting once again, I could feel her free hand now resting in the center of my back pressing me towards her as she moved her lips towards mine, kissing me in return.

There is one thing in life that you can never ask to do again, and that's of a first kiss. As our lips touched, we just stood there exploring each other's mouths with our tongues. There is nothing sexier than prolonged kissing. I can spend hours kissing and be totally satisfied because it is a real way to communicate passion and feel pleasure. I lost track of time standing there in Terry's kitchen, kissing someone who I had only met a few hours before. I could feel sensations come alive in me that have seemed to lay dormant for years. And there we were kissing like teenagers. At one point, we stopped our embrace and took a step back and just looked at each other, eyes gazing.

She then asked, "is this real?" I laughed, and all I could think of saying back is "I think so. Would you like for me to pinch you?" "I have a better idea", she said and as we embraced again, picking up where we had left off, she grabbed one of my hands and placed it on her ass. Because of the sheerness of the material in her dress, I could feel that she was likely wearing a thong, since all I felt was tightening flesh underneath.

Breaking our kiss again, I asked "Do you think the kitchen is cleaned up enough?"

"Do you think it really matters at this point?" was her response, with a seductive smile on her face.

"Well, how about we get more comfortable then." Not really asking a question, but making a suggestion as I guided Deb into the living room and onto one of the cushy leather sofas. As we sat down, she pulled off her pumps and tossed them a few feet away. Figuring I should probably do the same, I pulled my shoes off and tossed them near her pumps. I then put an arm around her and turned to look into her eyes. It didn't take long for each of us to lean in towards each other and resume deep kissing. With one arm around her and my free hand resting on hers, which was in her lap, we continued to kiss and explore each other's mouths going from a kiss, to light French kissing to deep French kissing.

Her perfume was a combination of floral and spice and gave me inspiration to start nibbling on her neck, starting with her right ear, and kissing my way down to her breastbone. She was delicious and I could feel my cock grow, forming a pronounce bulge in my trousers.

With my right hand now on the left side of her face, gently touching her hair and massaging her ear. I could hear her purr and her breathing become more heated with desire as we continued to kiss. The intensity of desire blocked everything out, including the soft music that was now playing in the room. With the back of my hand, I caressed her breasts. Through the sheer fabric, I could feel her nipples swell into what felt like large erasers making me hunger to see them and lick, suckle and nibble on them. I glanced over at the clock in the room, and it now said 1:10am. One of her hands was now on my thigh and I could feel her slowly rub me, moving towards the now pronounced tent that was my erection waiting to be freed.

In my ear Deb whispered, "I need to get more comfortable; I hope you don't mind." As she pulled away, she was now in a more upright sitting position as she reached behind herself with both hands to unclasp the hook at the top of her dress, and then unzipping the small zipper at the bottom, she then stood up facing me and wiggled free of her dress. With a wicked grin on her face, she whispered "now that's much better!"

The view of her was a gorgeous treat. She was wearing a very sheer red bra, the outline of very dark, and almost puffy areolas was as clear as day. Her thong panties had matching sheer material covering her crotch, allowing me to make out a very well-groomed dark runway where her coifed pubic hair remained. I was spellbound and full of lust.

"Are you comfortable?" she asked? At first, I was a little confused by her question, then I realized that she was looking down at the tent that had formed in my trousers, and that this was a strong hint that I needed to make myself as comfortable as she just did. Unclasping my belt and unzipping the fly, I pull off my pants and lay them over the back of the couch next to us with her dress.