Jan's Chicago Business Trip

This is a resubmission of an earlier story and I feel a much improved version. The story is complete, but If there is sufficient interest, I have left myself an opening at the end of the story for a Part 2.

I'm interested in receiving any constructive criticism as well any other possible sexual scenarios for Jan & Michael. Please take the time to apply whatever star rating you feel is appropriate.

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Before relating the details of my Chicago business trip, let me first tell you a bit about me.

I'm Jan. Taller than average at 5'9". However in my trademark 4 inch stilettos, I tower over most women, and many men as well. I like it that way! Long straight blonde hair reaching to the middle of my back. While not a youngster, I've kept my figure, long legs and 36D breasts really helping my image. I still manage to turn a fair share of heads.

As a business woman in the manufacturing industry, I know that sex sells, so I try to showcase my best assets, wearing short skirts or dresses with tight or low cut tops. Classy enough for business, but with a hint of the provocative.

While technically single, I have been with my significant other Michael for many years. Our relationship strong, we are virtually a married couple in all aspects, except in the eyes of the law. Both open minded, comfortable being nude in front of others, not swingers but "lifestyle" friendly.

As an executive assistant for a large manufacturing company, part of my job is to set up conferences with potential customers. These meetings normally held at hotels at various location around the country, usually with 20 to 40 people attending.

On this occasion, I was conducting a 2-day session, introducing my company and the services we provide to a group of existing and potential customers from the Chicago area. In addition to my presentation, I brought along members of various departments to discuss manufacturing details. The schedule also included a Meet and Greet on Thursday afternoon, and a cocktail party at the conclusion of the event on Friday.

As with most conferences, the attendees were predominately male. Although the group was interracially mixed, it was primarily made up of middle-aged black men.

Since the meeting bumped up against the weekend, I thought staying a few days to explore the "Windy City" would be fun. And why not take advantage, I was already here. Not wanting to be alone, I asked Michael to fly out and join me for the Friday evening cocktail party, and stay to enjoy the weekend.

Now for the crux of this story. Fast forward to Friday night. The cocktail party was in full swing, drinks flowing, everyone was chatting, having a good time. Being one of only a few women in the room and the conference host, I was the center of attention, I looked my absolute best, wearing a sexy low cut cocktail dress, hair and makeup perfect. I knew Michael would be excited to see me, and I wanted to impress him. I wanted him to be in the best possible mood, especially since I had some information I desperately needed to share, preferably in the privacy of our hotel room.

When Michael arrived, the cocktail party was already well in progress. I didn't have an opportunity to chat with him in private. We kissed, then I led him around the room, introducing him as my "significant other" of many years. Then the thing I was dreading finally happened. A tall, handsome, well built black man walked straight up to us and began his introduction.

"Hi, I'm Thomas, you must be Michael". As he shook Michael's hand, he continued, "Jan has told me so much about you, it's great to finally meet you in person. I guess I don't need to tell you, she is one hot lady!"

His self-introduction and bold statement left Michael with a quizzical look on his face. I cringed, hoping Thomas would leave it that, but really fretted about what Thomas might say next. I just stood there speechless, momentarily frozen.

Before I could interrupt, my worst fears were suddenly realized. Thomas put a hand to his mouth, a feigned attempt to muffle his voice, then began to speak directly to Michael.

"I hope you aren't offended, but Jan told me how much you like watching her having sex, especially with black men with large cocks like mine. Michael, let me tell you, your Jan is the best fuck I've had in a long time, and sucks a mean cock as well. Here, check this out," then takes out his cell phone.

And just like that, there I am with my lips wrapped around a thick black cock. Thomas's cock!

Thomas continued flicking his way through the photo album, showing Michael many pics of me, first posing with my legs spread, holding my pussy open, sucking his cock, then several others showing him fucking me in multiple positions. The final photo, his "coup de grâce", showing him kissing me, while come leaked out of my cunt, his large black cock and freshly drained balls, visible for maximum effect.

"Pretty hot, right?" Thomas said. "I just couldn't wait to show you these! I just knew you would love seeing them! Perhaps the three of us can get together tonight in her hotel room, like she and I did last night. You can join in or just sit back, watch the action first hand, take all the pics you want. As you can see, I'm not camera shy. I'm game if you guys are up for it! Just let me know and I'll be there!"

"Thomas, I'm glad that you got to experience Jan's sexuality. As you said, she is one very hot fuck, and although I love her dearly, I'm happy to share her on occasion with discriminating men such as yourself. However, it is Jan that decides when and whom she wants to have sex with, so your question about tonight should really be posed to her!" Michael replied, with more composure than I would have expected. We then walked away, but some of the smug grin on Thomas's face was erased.

Still startled, I started to explain, but Michael interrupted.

"No worries Jan! You did exactly what I would have wanted you to do. No explanation or apology is needed. All I ask is that you tell me exactly what happened, in the greatest possible detail, so I can enjoy your experience as well." The shock of hearing Thomas's speech beginning to fade, he added with a little laugh, "Try to get Thomas to send you a copy of those pictures. You looked amazing, so hot! I immediately got a hard-on just briefly viewing them!"

Since Michael didn't appear too upset, I was somewhat relieved, even proud of the way he handled Thomas's ballsy announcement. From the excitement I heard in his voice, I knew he would want to hear some details immediately! There was no way he would wait to discuss it later, in the privacy of my hotel room. Taking him aside, outside of the party where we could talk in private, I started to explain what happened!

This all began yesterday at the meeting. Of all the men in attendance, Thomas stood out head and shoulders above the rest, both figuratively and literally. Not only was he was the most handsome, but also the tallest. At least 6'6", perhaps more, towering over me, even in my 4 inch high heels. Dark skinned, a lady killer smile, exuding confidence. Impeccably dressed, his slacks framing a muscular ass and narrow waist. Wearing a trendy sport coat over a tailored dress shirt, open at the neck, and neatly tucked in at the waist. Overall his body gave the impression of an athlete, perhaps a football player, maybe recently retired Not a hulking lineman, but more like a wide receiver, lean and ready to out sprint his competitors. Any lady seeing him, would feel an instant attraction! I wasn't the exception!

Since I was here on the company clock, I tried to keep my growing attraction in check, and hopefully unnoticed by Thomas. Obviously my plan wasn't working too well. Throughout the day I could feel Thomas's eyes on me constantly, always flashing me a beautiful smile. I'll admit that I was enjoying his flirting, and did nothing to discourage him. Perhaps I was doing some flirting myself.

At the Meet & Greet, Thomas always seemed to be a part of whatever group I was socializing with. The other men didn't seem to mind, as he seemed to be a local hero, probbly due to his past involvement in sports. While we were chatting, he would casually touch my hand or arm. It appeared innocent enough, but I was aware and excited by it none the less. Later as I was socializing with some of the other businessmen, Thomas squeezed thru the crowd carrying drinks, and brushed against me, his hips touching my ass. I swore that I could feel his cock thru his pants.

"Oops, please excuse me!" he said, then gave me a wink. Silently indicating the contact was not entirely an accident.

"No problem, feel free to bump into my butt anytime", I said with a laugh. Perhaps I was being too bold, but with a couple of drinks in me, it just slipped out!

"I'll keep that in mind, then gave me another wink and smile." Not letting my comment slide.

A short time later, I excused myself from the party to use the hotel restroom. It was the trendy new unisex style, each stall completely private with a sink, mirror, and commode. As all of the stalls appeared to be empty, I picked the nearest one. Hiking up my skirt, then pulling down my thong panties, I sat to pee. My business almost complete when I heard the restroom door open, followed by footsteps that stopped in front of my stall. A light knock on the door soon followed.

"Sorry, it's occupied." I said

"Jan, it's Thomas! "

I couldn't believe what I was hearing! He must have seen me leave the party and followed me. Normally I would have been concerned at this type of behavior, but must admit, I was also excited and anxious to see where this was heading. Before I could think what to say, he continued.

"We've been flirting with each other all day, even caught you checking out my junk a few times! I know you felt it, when I bumped into you. Don't you at least want to chat in private, perhaps see what you have been wondering about? I promise you won't be disappointed! Now please unlatch the door before the next person comes in, so we can explore our mutual curiosity! If someone sees me standing outside of your stall, talking thru the door, it might be difficult for either of us to explain!"

Hesitating for a brief moment, I thought about the likely outcome of obeying his request. Throwing caution and common sense to the wind, as my breathing and heart rate increased, made my decision! With my hand trembling, I unlatched the door. As soon as I did, Thomas boldly stepped in, closing and re-latching the door behind him. Here I was, sitting on the commode, with my panties still around my ankles, and a large black man standing right in front of me. Now having second thoughts, I was about to protest, to tell him this was not a good idea, when I heard the restroom open again, as someone walked in and occupied another stall. Thankfully it was not adjacent to the one Thomas and I was now together in.

Thomas put a finger to his lips, indicating for me to be silent. He unbuckled his belt, then unzipped his pants, letting them drop to the floor. Pulling his boxer shorts down around his knees followed, allowing his cock to spring free. I wanted to say something, but was afraid that the other restroom occupant might hear.

I just sat there quietly, but couldn't help but give a muffled gasp when I saw how large his cock was. It was huge! Uncircumcised, at least 8 inches long and insanely thick, with large bulging veins, capable of reaching great depths in any woman! His large balls hanging low, keeping his sperm at a healthy temperature. The man was a baby making machine.

Making the first move, he took my hand and placed it on his cock. I offered no resistance or objection.

His hand still on mine, together we pulled back his thick foreskin, revealing its large mushroom-shaped head. His cock was so thick I couldn't wrap my fingers fully around the shaft. Soon I was holding his huge member entirely on my own accord, marveling at its girth and weight, reluctant to let go. I began to nervously stroke him, totally fascinated, watching the foreskin swallow up the large head when released, only to watch it slowly reappear, as the foreskin tightly clung to his cock when pulled back.

As my excitement grew, without additional encouragement, I used my other hand to heft his huge ball sack, feeling the nuggets it contained. Each one nearly the size of a hen's egg, but soft and spongy. I couldn't imagine the amount of come they would be capable of producing, but had a good idea I would soon find out, if I didn't bring this encounter to an immediate halt.

Talk about an unplanned and strange circumstance! Here I was, sitting on a commode in a restroom stall, stroking a near-strangers huge black cock with one hand while the other massaged his balls. The fact that there was another occupant in the restroom made me extremely nervous, but must admit, it was also very exciting. You can imagine what happened next.

Not wasting any time, Thomas placed his hand behind my head and pulled me towards him. As his cock loomed in my face, I could clearly see the copious amount of pre-come he had generated, so much that it was about to drip. As my lips neared the head of his cock, I instinctively reached out with my tongue to catch it, before it fell to the floor. It tasted almost sweet! Returning to the task at hand, wrapping my lips back around him, when I heard the low click sound of a camera shutter, realizing he had just taken a picture of me sucking his cock. I should have protested, ended it right there, but was too excited to do so!

As he continued to pull my head towards him, I further parted my lips as he pushed more and more of his cock into my mouth. Still holding his foreskin back, I swirled my tongue around the head, paying special attention to the sensitive bridge of skin, between the underside of the head and shaft. Hearing more pictures being taken, I briefly thought to myself, oh well, one or twenty, did it really matter?

At first, he used his hand on the back of my head to guide his cock in and out of my mouth. After sucking him for a while, I finally realized that he had removed his hand, as I continued to suck him on my own, without any additional encouragement. It was like I was on autopilot, and just did as he asked, now a willing participant.

Finally we heard the commode flush in the other stall, its unknowing occupant washed their hands then left, leaving us alone again. Now free to talk, albeit with lowered voice, he continued.

"You like sucking my cock, don't you? Aren't you glad I made the first move and called you out on our flirting?"

My mouth full of cock, I nodded my head in the affirmative.

"Jan, please look at my face, while you suck my cock! I want to see those big beautiful eyes of yours, watch your lips as my cock disappears between them. I want you to see my face, to see just how much pleasure you are giving me!" Thomas said, taking full command of this encounter.

I did as he asked, but what I observed was more of a grin of mastery, rather than the face of sexual pleasure. It didn't matter, I was now enjoying his large cock, one that I had only subconsciously fantasized about, just a scant while ago.

Continuing to exert his dominance, Thomas pulled my head back, asking me to give his balls some additional love. Removing my mouth from his cock, I lifted his ball sack and began to caress them one at a time with my tongue. He then encouraged me to take them into my mouth and suck them. At first, I didn't think that I could fit one in my mouth, but trying hard to please him, I opened even wider and one just slipped in.

"Oh yeah, that feels fantastic! Suck those balls Jan!" Moaning in appreciation.

Despite its size, I managed to gently roll one around in my mouth, using my tongue as much as possible given the limited space available. Satisfied I had sufficiently serviced one, I repeated my efforts on the other. When I felt both balls were thoroughly attended to, I returned to sucking his cock, determined to bring this to closure. His trash talking began again.

"Girl, that was fantastic! You really know how to treat my junk. Do you do this for your man as well? I'm guessing you do, that kind of talent comes with lots of practice. Tell me, does your significant other know you like other men's' cocks, especially if they're big and black, like mine?

"Yes!" I mumbled .

"Does he like to watch you suck and fuck other men?"

I nodded my affirmation, but kept on sucking.

"Ok, now it all makes sense, he's a cuckold! " Then with a little laugh Thomas chided me. "Tell me your boyfriend's name. I want to be able to greet him properly when we meet."

"It's Michael, his name is Michael." lifting my mouth from his cock momentarily.

The camera shutter clicked again.

"Well, your Michael is going to love seeing this, and all of the others, isn't he?"

He turned his phone towards me, showing me the picture. I said nothing, then returned to sucking his cock with renewed energy. Partially because I was so turned on, but also wanting to make him come before someone entered the restroom, and maybe discovered what was going on. Finally feeling his ball sack beginning to contract, I knew I was getting close to my goal.

Suddenly removing his cock from my mouth, he helped me to stand, then turned me around to face the sink and mirror at the back of the stall. It was now obvious, a simple blowjob wasn't going to cut it for Thomas. He wanted to fuck me, and I must admit, I was hot to feel him inside me as well.

"Don't worry", He told me. "If someone walks in, I'll just quietly slow stroke you. No one will be the wiser. All you have to do is keep silent."

Not totally reassured, I allowed him to bend me over the sink, then used my hands against the counter to brace myself. With my face now in the mirror, I was able to watch what was going on, as Thomas prepared to fuck me from behind. As he worked my skirt up over my hips, it bunched around my waist, revealing my ass and pussy to his view, my panties already around my ankles. Running his hand over my ass, even slapping it, he started rubbing his cock up and down my now sopping wet slit. Telling me my cunt was the wettest he'd ever seen, and how he couldn't wait to get his cock inside me. Using his hand, he distributed my juices over the length of his cock. He was now poised and ready, as was I!

After working the head into my cunt, he asked me if I was ready to be fucked. Before I could even respond, he began sinking the remainder of his huge member into me, in a single, agonizingly slow thrust. It was so big, but felt so good!

"Oh fuck, oh fuck," escaped from my lips before I realized just how loud I was moaning, as his cock continued its descent into my wet cunt. I had to bite my lip, reminding me to quell any further sounds of pleasure!

An expert, Thomas knew just how fast my pussy would stretch and spread to accommodate him, without causing undue pain. My cunt felt like a sausage casing being slowly filled with hot meat. It just kept on expanding as the head of his cock penetrated me deeper and deeper, adapting itself to his large size. I was unsure my pussy could contain all he had to offer. That question was soon answered, when I finally felt his hips come into contact with the cheeks of my ass. I must admit, I had feelings of relief, and a sense of proud accomplishment. Now bottomed out, Thomas remained momentarily motionless, then leaned forward and whispered in my ear.

"That's a good girl, you've taken all my cock like a champ! Now get ready for a real fucking!"

And fuck me he did! Slow stroking at first, but that didn't last. With one hand on my hip and the other still grasping his cell phone, he transitioned to fucking me harder and harder! As he fucked me from behind, I could hear the sound of his camera shutter clicking over and over again, and could only imagine the images being captured.