Jan's Chicago Business Trip Pt. 02

First a brief recap of my original story, "Jan's Chicago Business Trip".

I'm Jan, 5'9" 36D breast, blonde straight hair, long sexy legs. Not a youngster, but still turn plenty of heads. Single but in a long term relationship (many years) with my "significant other" Michael.

During a business conference in Chicago, I met, and ultimately had an affair with, an extremely attractive black man named Thomas. During our time together, I let Thomas know that Michael, my significant other, likes watching me having sex with other men. Normally, Michael and I agree ahead of time on the man, lucky enough to be selected for one of these sexual "adventures". It works for us, and I love how excited Michael gets watching me perform. It provides us with hours of sexual entertainment, as we relive these dalliances at a later time.

This time with Thomas, I was alone when it "just happened". Just a fling, no strings, but without Michael's consent. I had every intention of telling him about it as soon as I saw him. Hopefully he wouldn't be upset or too disappointed in me for breaking our "rules".

Michael flew to Chicago to join me, his flight late, so we agreed to meet at the cocktail party. With everything going on, I hadn't yet found the right time to tell him about Thomas, but planned to do so when we returned to my hotel.

As we made our rounds at the party, Thomas boldly introduced himself to Michael, then proceeded to tell him about our affair, even showing Michael graphic pictures of the two of us.

Knowing Michael's proclivity for watching me having sex with other men, Thomas boldly offered Michael and I the possibility of a repeat performance, the difference being Michael could be there to observe in person.

Michael was totally blindsided by this. I took him aside immediately, and began to explain the details our affair, as covered in my earlier story, "Jan's Chicago Business Trip". This is what happened next.

Chapter 1 - The offer!

The details of my affair now complete, there was one final decision to be made before Michael and I returned to the party.

"After everything I've told you, are you really interested in Thomas's offer? I wasn't very happy with the way he sprung our tryst on you, and for that I am truly sorry. It shouldn't have happened this way, and promise it never will again. Do you really want him to join us tonight, while you watch, after him pulling that stunt?"

"Babe, yes I was surprised, a bit taken back, but not upset with you. If I was there, I would have agreed with your choice, so I'm ok with whatever you decide! Look, I saw the pictures of the two of you. Obviously he showed you a good time. I agree, he's a cocky S O B, but after seeing pictures of the two of you together, I'm willing to swallow some pride for the opportunity to watch you having sex with him again. Pictures are nice, but for me there's nothing like watching you in real time. Consider it a re-do. Blowing off this opportunity because of his attitude, would be like cutting off my nose to spite my face. Besides the offer includes me taking my own photos. You know my vote!"

Discretely touching Michael's crotch, feeling his hard cock thru his pants, I knew for sure we had made the right decision. Still at Michael's side, I kissed him, whispered in his ear, "I love you honey!"

"Love you too babe! Let's make this happen!" His simple response.

Our discussion over and decision made, we returned to the party. I left Michael with some other guests and walked over to the bar alone. I caught Thomas's eye, and signaling him to join me. We both ordered another drink. I quietly spoke.

"We are on for tonight, that is if you are still interested."

As we both leaned forward facing the bar, he turned towards me, his crotch rubbing against my hip, I could feel his hard cock thru his pants.

"I think I just showed you my answer, but if you need to hear it directly from my lips, I want to be with you tonight. Been thinking about you all day. Your lips around my cock, fucking that hot cunt of yours again. How could I possibly say no!"

Continuing, "And Michael? Is he down for this as well?"

"Yes he is."

"I was almost certain he would be! I saw the look on his face when I showed him your pictures earlier. First, the look of shock, which quickly turned into sheer sexual anguish. I'm sure his cock was fully erect before seeing even the 2nd picture. Adding, "By the time I finished showing them to him, I wouldn't have been surprised if he came in his pants. They are so hot! I've wanted to jerk off every time I viewed them, but didn't, I wanted my balls fully charged for you, almost certain that we would be together tonight."

"Michael is more than ok with this!" I told him. "He really wants to see you fuck me."

"Perfect, now tell me something! Is you're pussy wet, just talking to me about it?"

"You know it is, and if we weren't here, I'd let you check it for yourself! Boldly adding, "You know this isn't only about Michael, I want you to fuck me again, feel your huge cock inside me, multiple times if possible! I can't wait!"

Before leaving Thomas, I arranged for us to meet him in the hotel bar at 9 PM for drinks, then ultimately head back to my room for the evening's fun-time "activities".

He said, "Drinks are a good idea. It will help to ease any anxiety between the three of us, then we can proceed to the main event!"

Turning his attention from me, he looked across the room, spotted Michael and gave him a grin and thumbs up, indicating the deal was done. Michael raised his glass, signaling his affirmation.

The party now over, we returned to my hotel room. The door was barely closed, when Michael came up behind me and started kissing my neck, hungrily. His hands first squeezing my breasts, then one found it's way under my skirt, feeling my cunt thru my panties. He didn't comment on finding them soaking wet, but I assumed he knew the reason.

Michael literally tore off my clothes, threw me on the bed, spread my legs, burried his head between them. Lapping at my cunt, covering every inch with his tongue then proceeded to suck on my clit.

I wondered if he was trying to taste any remnants of Thomas, perhaps fantasizing it was freshly fucked. Well, it kinda was, but that was more than 8 hours ago, but it didn't matter. With thoughts of events yet to come, and his talented tongue, I was quick to orgasm.

Michael then quickly climbed between my legs and started fucking me. I couldn't help but wonder if my cunt felt looser to him, especially since Thomas recently fucked me so many times with his huge cock. If it felt looser, he never mentioned it, now fucking me hard and fast. I'm sure the pictures Thomas showed him, and the story I told him, was more than he could take. He came in my cunt after only a few minutes. I think he gave me his largest load ever.

After a brief nap, I got up to shower and prepare for the evening. Hair perfect and makeup impeccable, wearing the sexy red lipstick that Michael loves so much. Selected a thong panty, short miniskirt, and a slinky low cut halter top. One that showed generous cleavage, and would easily reveal a nipple, if I made the right move!

My 5 inch sexy stiletto heals transformed me into a 6 foot 3 inch Amazon woman. Now towering over Michael, but still leaving me several inches shy of Thomas's 6 foot 6 inch hulking frame. Seeing me like this, Michael told me this was going to be like watching the "Battle of the Titans".

Chapter 2

Meanwhile, Thomas, resting in his room, thinking about events yet to play out, decided to call his old football buddy Jason, and share the details of his latest conquest.

"Man, have I got a story to tell you!" Then proceeded to tell Jason about me, this super hot woman he met at a business meeting, and how he has been fucking the shit out of her for the last 24 hours.

"Bro, I'm telling you, this chick is the fucking bomb. Tall, hot body and loves black cock. I've been fucking her brains out at every opportunity. In fact, I spent all last night with her. I can't tell you how many times I nutted in her cunt!" Then added, "Here, I'll text you some pics! Let me know what you think!"

Upon receiving them Jason said, "Wow, she is so hot! Man, you are one lucky dude! Are you going to be hitting that again tonight?"

"Here's the deal. This chick's boyfriend is now in town, but likes to watch her suck cock and being fucked. He's a real cuckold, doesn't even want to participate. I offered them my services for tonight, and they were down with it. No hesitation from either. All he wants is to be there, watch, and take some pictures. All fine by me, so it's on!

Jason saying,"You lucky dog!" Adding, "Hey, any chance of me getting in on this as well? We could run "train" on her! You know I've shared with you in the past, this is a golden opportunity for some payback!"

Thomas, "That's why I called. I might be able to make this happen. Jan is hot for black cock, but don't think Jan has ever been with two brothers at the same time though. I think the boyfriend will be down with it, but If I call to check, I'm afraid she might give it too much thought, and bow out. This needs to be a spontaneous arrangement. Let's just meet at the bar at 9 PM and see where it goes. I think we are both in for a great night!"

Adding with a laugh, "Whatever you do, don't let Jan know about that monster cock of yours until we get her behind closed doors. You'll surely scare her away before we even get started if she finds out!"

"Thomas my friend, you are the man! Thanks for thinking of me! Seriously, my balls haven't been emptied in a week. Looking at her pictures, her cunt or mouth would be the perfect place to drain the load I've been building up!"

Thomas hung up the phone, pleased with himself. Now he was not only getting to fuck Jan, but would most likely be able to tag team her with his buddy. His only regret, was he would lose his title of the biggest cock that Jan ever fucked, to his friend Jason. The consolation being, he would be there to watch him earn it. All was well in the world of Thomas!

Chapter 3

Arriving at the hotel bar at 9 PM, Michael and I immediately spotted Thomas, standing at the bar, talking with another black gentleman. This man was even taller, with a more imposing frame than Thomas, but still handsome.

Spotting us as we approached, Thomas extended a hand to greet Michael, then leaned in giving me a lingering kiss on the lips.

Immediately breaking the ice and taking control, Thomas's tongue was in my mouth, as if Michael wasn't even there. I was somewhat shocked, but went along with it. Giving him my tongue as well. I'm sure it was a turn-on for Michael though, a sure sign that the evening was heading in the right direction.

When he broke away, he introduced the other man as his friend Jason. Jason didn't appear phased by Thomas's bold greeting kiss. After shaking hands with Michael, Jason boldly leaned in, and kissed me on the lips, but at least there was no tongue action.

Jason was a giant, heavily muscled, strikingly handsome. Forgive me but I was already picturing his huge black cock in my mind. As I was to soon find out, the image I had in mind didn't give him sufficient credit.

"So nice to meet you both. Thomas has told me so much about you!"

"Probably way too much!" Spilled out of my mouth before I realized I said it!

Thomas, ignoring my dig, telling us, "Jason is an old football buddy, coincidently staying at a nearby hotel. We had already planned on getting together tonight for drinks. That was before a more attractive offer happened."

Obviously Thomas was now referring to our planned "ménage a trois". It was now obvious, Thomas had told Jason about our "plans" for the evening. What else he told him was still in question, but I was pretty sure it was full of details, and likely a review of Thomas's photo album.

Of course Jason was very interested in meeting us, especially me! His hungry eyes were already undressing and devouring me. I knew almost immediately, if he had his way, he would definitely be fucking me before the night was over.

I was already thinking the same thing. From what I saw so far, I wouldn't be throwing up any roadblocks.

After introductions, Thomas suggested we take a booth and order a round of drinks. Adding, "I hope you don't mind if Jason joins us." giving me a quick wink.

Not really surprised, I found myself immediately saying, "Of course not, Jason please join us." I had to stop myself from adding, "For the entire evening!" He was that hot! Now I had an image in my mind I hadn't even considered. Entertaining two black cocks. I wondered briefly to myself if Michael would object, but knew right away he would tell me to "go for it"!

As we approached the booth, the seating arrangement seemed almost pre-planned. Thomas took my hand and we slid into one side with Jason sliding in next to me. This left Michael sitting by himself on the other side of the table. A glance at him as he shrugged his shoulders, let me know that with this unexpected turn of events, the outcome was entirely up to me.

As the conversation moved along, it was obvious that both men were completely focused on me.

Michael was there basically as an observer.

Initially we engaged in small talk, but eventually the conversation turned towards the real reason for all of us being there.

Thomas explaining to Jason, "Jan is basically a "hotwife", even though she and Michael aren't technically married. Free to have sex with other men while Michael remains completely faithful. Permitted to go off alone, but prefers to have Michael there with her, for her safety, but also to watch her in action. It's a big turn-on for both."

As he said this, I felt Thomas's hand come to rest on my knee. Almost immediately it began moving upwards, kneading my inner thigh as he did so. I did nothing to impede his progress, actually spreading my legs slightly to permit him ease of access. My glance to Michael was all that was needed, silently letting him know that events he would be interested in, had now begun.

Thomas continued, "Michael, you are ok with this right? I know you are turned on watching Jan having sex! I understand completely. I would love to stand by and watch her in action myself, which brings me to the reason I asked Jason to stop by!" Then the big question finally came, "Jan, Jason finds you very attractive, and would like to join us tonight. If it is ok, with the both of you? He is a gentleman and very respectful. Jan, you will surely enjoy his company! Then adding with a laugh, "He's also hung like a horse!"

As I glanced around at the men at the table, it was suddenly quiet, everyone looking at me intensely.

I felt Jason's hand come to rest on my other knee. I wasn't really surprised when I felt his hand beginning a similar journey upwards under my skirt.

A few moments later, I noticed one of Michael's hand had disappeared beneath the table as well. I assumed that he was now massaging his erection thru his pants, his mind running wild, imagining what was happening on my side of the table.

Thomas's hand was the first to win the race to my thong. Once there, his fingers began rubbing up and down my slit, teasing my clit thru the now sopping wet silky material.

Telling Michael and Jason, "Jan's pussy is so wet, it has already soaked her thong."

His next move was to hook a finger under one edge, pulling it aside.

Thomas again reporting, "Michael, you should know that now that I am holding her pesky thong out of the way,

Jason's fingers are now doing their best massage on Jan's bare pussy lips and clit!"

I was slightly embarrassed by Thomas's bold announcement, but Michael didn't seem offended. It appeared he was enjoying Thomas's, "state of Jan's private parts" report.

Thinking to myself, "it is what it is", so all I could do was lean back against the bench seat, close my eyes and enjoy the attention I was receiving.

When I finally opened my eyes, I saw Michael's smile, showing he was perfectly happy with the events in progress.

Leaning close to my ear, Thomas whispered his request.

"Jan, we are going to take off your thong!"

After a brief hesitation, I raised my hips clear of the bench seat. Working in a coordinated effort, Jason and Thomas moved my skirt upward, bunching around my waist, then slid my soaked thong over my hips and down my legs.

Once below my knees, I reached down, removing them completely. About to put them in my purse, Thomas stopped me, had me place them on the table for Michael to see. I did as he asked. Thomas picked them up and brought them to his nose. After sampling their fragrance, he handed them to Michael.

"I think you might like to hold onto these, especially since Jan won't be needing them anytime soon."

As I started to pull my skirt down, Thomas stopped me.

"Please leave it where it is, for now!"

I did as he asked. Now my naked ass and bare pussy was resting on the bench seat.

Leaning back, feeling Jason and Thomas spreading my legs. Their fingers again touching my cunt. Thomas's circling my clit, Jason busy teasing my labia.

Pressing even further back into the seat, it was all I could do to not orgasm, right then and there.

Surely, anyone even seeing our booth would notice the unbalanced seating arrangement, two huge black men closely surrounding a sexily dressed blonde white woman, her husband or boyfriend seated alone, on the far side of the table.

This unusual scene itself invited even closer inspection. Anyone doing so, would find the same blonde woman with her skirt up around her waist, both black men busy with their hands between her legs.

I tried not to think about it too much.

My nerves were getting the best of me. As I glanced around the room, it appeared our little four-some was indeed gathering attention. Mainly from other men standing at the bar, repeatedly glancing in our direction, making muffled comments to each other.

Luckily, I didn't recognize any of them from the todays meeting!

Sensing my growing discomfort, with such obvious activity in a public setting, Michael suggested, "Perhaps we should take this to our room!"

Adding, "Jan, I assume Jason will also be joining us?"

"I think Jan has already signaled her consent." Thomas said with a sly smile, then wiped his fingers, now wet from my juices, on a napkin.

I quietly added my approval, "Yes of course, Jason please join us."

"It will be my pleasure!" His enthusiastic reply.

With that said, I pulled my skirt back down, covering my ass before standing up and leaving the booth.

Thomas now saying, "Jason and I will escort Jan to her room. You can join us after you settle the bar tab."

"I'll join you in a few minutes." Was Michael simple reply.

Chapter 4

Thomas, Jason and I headed off to the hotel elevator. The door had no sooner closed and they were all over me.

Jason's hands under my skirt, massaging my cunt, Thomas behind me, hands inside my top, kneading my naked breasts, gently teasing my nipples to an even more erect state.

Hopefully no one was monitoring the elevator camera. If it was, they were being treated to quite a show. I'm sure it was being recorded for security purposes, but suspect it wasn't the first time that hot activity occurred there.

My room just down a few doors from the elevator, Thomas already knew the way, having visited me there only the night before. The key to the hotel room was produced and the three of us entered.

There was no pretense, no small talk, both men simply started removing their clothes. Following their cue, I did likewise.

Jason, like Thomas, just wanted to get down to it. Their cocks hard and ready for me. Ready for my attention. Truth be told, I was ready for them as well.