A Worplace Bet Goes Too Far

My name is Keshia and I'm a 35-year-old ad agent working for an agency in NY. I've been married to my husband Marcus for twelve years now. We decided early on that we didn't want kids right away because we wanted to focus on our careers. Marcus and I are the same age, and he works in marketing. I first saw him while I was cheerleading in college, and he was on the football team. Sparks flew from the beginning between us, and we've been together since.

I've been working at this advertising agency for almost seven years now, and I've been involved in securing several multi-million-dollar contracts with well-known companies all over the world. Our team has had a lot of success, and we all work well together. Our boss, Mike, just turned 50 and he's the oldest one on the team. Mike has the reputation of being a player, and he's never been married. It seems that he's slept with just about every decent looking woman in the building whether single or married.

There are two women on our team that have slept with Mike that I know of. Tran is a 30-year-old Chinese woman and Lexi is a 25-year-old Hispanic. I'm the only African American on the team, and we have two other Caucasian men. There was a rumor that Mike was "gifted" in the anatomy department, and these other two women both confirmed it. Mike has been shamelessly flirting with me for years to the point that it could be considered harassment, but I don't pay much attention to him.

You would think that he'd just give up after being declined so many times, but he doesn't. I do have to say that he's persistent. I guess that I should take it as a compliment that he keeps it up. It's either that or the fact that he sees me as a challenge since he can't have me. It's probably the latter. I have stayed in great shape and take pride in my body. I'm only 5'2" with long jet-black hair that falls mid-back. My ass is still firm from countless hours of working out, and I have natural C cup breasts that have defied my age.

People are always telling me that I look like a black Megan Fox. It's flattering because I know she's sexy and lusted after. We had been working on a pitch for a company that was based out of LA that would be our biggest contract in the agency. It was a longshot pitch because we heard from a reliable source that they were going with someone else. Our president insisted that we put the time in and make a run at it anyway.

We worked countless hours coming up with slogans and angles to land this account. We were due to fly out to LA in a week to make this pitch. Mike had chosen me and Tim to join him on the trip and assist with the presentation. We were to spend a total of four days in LA. We flew out the day prior to the presentation to give us time to make final tweaks.

The three of us worked well into the evening until we came up with the final plan. We were having dinner in one of the restaurants at the hotel along with a few drinks. Tim had excused himself and said he was going to bed. I think the jet lag was getting to him. I was excited for the presentation, but knew it was a long shot. I asked Mike what he thought our chances were, and he says, "just make sure you put on a skirt with a high slit and a top that shows those beautiful breasts and we're a shoe in."

The slight buzz I had between the alcohol and jet lag caused me to jokingly say, "maybe I should just go naked, and it'll be a lock." I should've known better because Mike's eyes lit up as soon as the word naked came out of my mouth. That seemed to be a segway for Mike to start back in with his flirting.

"Who could resist that sexy caramel skin?" Mike said with devilish grin.

"Knowing my luck, it'll be a woman that we are giving the pitch to." I replied.

"Maybe she's into chicks." Mike said laughing.

I knew that I shouldn't have opened pandora's box, but I just couldn't help myself.

"Hopefully she's sexy then. I wouldn't be opposed to a little girl on girl to get the deal sealed."

Mike's eyes bugged out. Anytime his innuendos started to fly, I would shut them down right away. I figured I'd feed it back to him this time and make him suffer a bit. I could tell he was in sensory overload imagining that image.

"I'd love to be a party to that situation." Mike said.

"I bet you would. Maybe if you land this pitch by some miracle, I'll make it happen."

Mike was quick to respond, "you're on!"

I'm not much of a skeptic, but I knew the chances of us landing this were slim to none and slim's ship sailed a long time ago. I had just finished another drink and decided to take it further.

"I tell you what, if you can pull this off, I'll let you have me our last night here."

By the look of determination and focus that Mike had on his face, it hit me that I may've screwed up. It would be great for the company to land this contract, but not at the expense of my marriage. I'd always been faithful to Marcus, even though he's had a couple missteps throughout our marriage. Mike was a handsome guy and obviously lusts after me, but I just couldn't. We decided to call it a night and get some sleep.

I woke up the next morning and the first thing that came to my mind was that stupid bet I made with Mike. I was feeling guilty like I'd already cheated, so I called Marcus to hear his voice. We talked a little about the hotel and if I was ready for this presentation. Marcus wished me well, and then I hopped in the shower. As I was washing myself in the shower, I found myself daydreaming about the scenario of being with another woman. Since our conversation last night, I found myself becoming more curious.

I started soaping my supple caramel toned breasts and felt a tingle between my legs. My next vision was of Mike feeding me this glorious cock that I've heard the other women in the office talking about. "Could it really be that big?" I thought to myself. Is he really the lover that they've described. My fingers started to explore my pussy. First one finger, then two. I was now probing my swollen clit with one hand and caressing my breast with the other. Before I knew it, I was trembling in orgasm. The rush that came over my body was overwhelming.

I gathered my senses and finished up the shower. I laid out a couple different outfits to wear. They were both considered business attire, but one was more revealing than the other. I was thinking about what Mike said last night, and I decided to go with the more revealing one. The shirt was lower cut and exposed the tops of my breasts with the skirt having a higher slit. I had some 4" pumps and left my hair down.

When I walked down into the lobby, Mike and Tim were already waiting.

"Damn, you look sexy!" Mike said unapologetically.

Tim agreed and laughed at Mike for blatantly saying it. Tim was married also, but I heard his faithfulness to his wife was questionable. Tim was about my age also. He was a handsome guy, but he wasn't an Adonis. We loaded up into the rental car and headed out for the meeting. We were greeted right away by their hospitality team and showed toward the board room. We took our time setting everything up to make sure we could give the best pitch possible.

Finally, it was game time. Their team filed into the board room and gathered around the large meeting table. Their people were an equal split of men and women. I caught myself thinking about last night's conversation as this one blonde woman walked in. She was gorgeous. I don't consider myself bi-sexual, but I did experiment with some of the girls on the squad in college. I noticed that she was sizing me up also. There was also a very handsome man that appeared to be in his mid-fifties that was locked in on me. It turns out that he was the president of the company.

We went around the room and made our introductions. The blonde woman's name was Lacy and the president's name was Carl. They started out by giving us a background on the company and telling us what their goals for advertising were. Mike was sitting next to me and squeezed my thigh as he stood up. I have to admit that I was impressed by the way Mike seemingly took over the room for the next thirty minutes or so. Their team stayed engaged, and they were nodding in agreement for most of what Mike was pitching. I noticed that Lacy and Carl frequently brought their eyes back to me.

I stood up when called upon by Mike to aid in the presentation, and the stares became more noticeable. Mike and I fielded questions for the next hour it seemed, and then we concluded the meeting. As they were exiting, Carl stopped and whispered, "I look forward to working with you." This took me by surprise because we didn't think we'd have a decision for a while. Maybe I was reading into it. Lacy stopped by and told me how impressed she was with the pitch and our agency.

"How long will you be in town?" She asked.

"We are scheduled to be here tonight and tomorrow night and then head back the following morning." I replied.

"Where are you staying?" She asked with a coy look.

"They put us up in a hotel downtown."

Lacy slid me her business card and told me to shoot her a message when we got settled later. We could have a drink while discussing more business she told me. I found this rather odd. Lacy was the VP, so maybe it was legit. She seemed kind of young for a VP. I will gladly meet with her to talk business if it gives us a better chance at landing this deal. Tim asked me what she said, and I explained it. The whole ride back to the hotel, the guys were hassling me saying that I was going to have to be the one that closed the deal.

We all changed over when we got back to the hotel and decided to go for some lunch. We found a local lounge and decided we'd try it out. Mike was going on and on about the pitch saying how good he thought it went as we ordered our drinks. We all decided that cocktails were in order to celebrate our win or loss. At that point, we had no idea which. As we ate our lunch, we continued to sip on our drinks. Before I realized it, I ended up having three or four drinks and was now beginning to feel buzzed.

Mike and Tim seemed to be getting loose as well. I told the guys that I wanted to relax for a while back at the hotel, so we all headed out. As we went to head to our rooms, Mike made a comment that I should get ready to pay off my bet. I quickly told him that we'd have to land the account first. I wanted us to land the account for the company, but I didn't want to have to deal with Mike trying to make me live up to the bet.

When I got to my room, I stripped off my business attire and just laid on the bed. It felt good to just lay there and relax. I found the business card that Lacy gave me. I went back and forth on whether or not I should message her. I decided to go ahead and do it.

"Hey Lacy, this is Keshia. I just wanted to let you know that I'm back out our hotel now, and I don't have any plans for the evening."

Lacy immediately responded. "Drinks at 7?"

I told her that would be great.

"I'll be at your hotel at 7. Dress casual." She replied.

I laid on the bed and found my hands exploring my body again while I pictured Lacy. It had to be the buzz that was taking over me, but I brought myself to another trembling orgasm. My moment of bliss was interrupted by a knock at the door. I jumped up and put on the hotel robe and went to the door. I opened up to see Mike in swim trunks and a tank top.

"What's up Mike?

"Put your suit on and let's go down by the pool for a while." He said with a smile.

"Ok. Give me a few minutes and I'll change over." I spoke.

Mike stepped in and said, "I can help you tie your suit if you'd like."

"Ha Ha funny man. I think I can get it on perfectly fine by myself."

"Well, It never hurts to ask." He said with a grin."

I grabbed my bikini out of the suitcase and headed to the bathroom. As I dropped the robe, I reached for my bottoms and realized that I'd grabbed the wrong suit. I ended up grabbing my other white bikini that had a thong for the bottoms. This was one that I only wore at our house. To say that this was revealing is an understatement. It was a microkini that had just enough cloth to cover up the sweet spots. The top barely covered my dark areolas. I was feeling embarrassed to go out in front of anyone but my husband in this. I knew this would also stir up Mike relentless attempts to have his way with me.

I began looking into the mirror as I got it on and noticing how sexy I felt. Not to be vain at all, but I did look good in it. My caramel skin popped next to the pearl white straps and cloth. The contrast alone was arousing. My supple breasts poured out of the sides of my top with just the nipples and areolas covered. I decided that I was going to just wear it proudly. I did pack a sarong to go around my waste for walking through the hotel. If I were to bend over, anyone behind me would surely get a good look at my pussy and asshole.

I stepped out of the bathroom and Mike almost fell off the chair.

"Good lord woman! How am I supposed to focus on anything while you're wearing that?" He spoke.

"I screwed up and brought the wrong suit. This was meant for only my husband's eyes." I said with a devilish grin.

"I'd give anything to be your husband." He blurted out.

I noticed that he was starting to get a bulge in his pants, and I couldn't believe it. I could see the outline of what appeared to be a huge cock.

"Come on Casanova. Let's get down to the pool before you get too excited."

He quickly followed me out the door and made a point to stay behind me the whole way to the pool. We found a couple lounge chairs and staked our claim. I asked him where Tim was, and he said that he wanted to relax in the room for a while. The pool had just a few people laying around it. The women that were there looked to be closer to Mike's age and attractive. Mike's head was on a constant swivel trying to continually check us all out. When he laid back on the lounge chair, His swollen member became more prominent.

I tried not the stare, but I couldn't help myself. What if it was as big as the other women in the office said. I'd never been with a white man before, and I've always heard that they had average sized cocks that were only about 5 inches. Marcus isn't the stereotypical black man that's hung like a mandingo, but he does have a nice 7-1/2" cock that's thick. I closed my eyes, and my mind started to wonder what it would feel like to have this pale white cock filling my pussy. I kept playing the scenario over and over in my head.

I found myself wondering if I could even get it in my mouth. I have an affinity for giving head. Marcus loves it. I wonder what he'd think right now if he knew I was imagining putting a thick white cock between my pouty lips while I massaged my moist pussy. To be honest, I didn't care at the moment. These visions were keeping me on a high that I was going to ride right at this moment. I decided to tease Mike, so I rolled over on my stomach. Now my bare caramel toned ass cheeks were fully exposed with just a string parting them. I spread my legs just enough to get a good look at my pussy consuming the thin material of my bottoms.

I acted like my eyes were completely shut, but I could see Mike fidgeting and nonchalantly rubbing his growing bulge. It looked as thick as my wrist from what my squinting eyes could see. I felt my pussy start to get wet. I was afraid that this would be obvious since my bottoms were buried in it. The erotic thoughts were becoming overwhelming. I was fighting the urge to bury my fingers in my pussy. I started to wiggle and grind my hips into the lounger. Every movement sent the cloth from my pussy deeper into the now soaking wet crevasse.

Mike's eyes were focused on my ass, so I just assumed that he could tell how wet I was. I couldn't take it any longer. I needed to have my pussy explored. I opened my eyes and told Mike that I was going to head back to the room. He made no effort to hide his raging hard on when he stood up from the lounger. I wrapped my sarong back around my waist, and we headed back to our rooms. I could feel Mike's eyes burning a hole in my caramel black ass as I strutted in front of him.

Mike couldn't take it any longer. As soon as the elevator doors closed, he grabbed me and stuck his tongue in my mouth while cupping my ass cheeks. My first reaction was to resist, but I found myself exploring his mouth also. I instinctively reached down as he was kissing me passionately and grabbed his cock from the outside of his trunks. It felt even bigger than I imagined. The elevator doors opened at our floor, and he whisked me away to my room. His hands were all over my ass, and I couldn't swipe the card fast enough.

We got into the room and Mike resumed kissing me. I reached inside his trunks and grabbed his bare cock while gasping from its size.

"Do you like what you feel down there?" He whispered.

"Ohhhhh god, it's so fucking big. All the girls were right." I replied as we continud to kiss.

I dropped to my knees with no hesitation because I had to see it. Moreso yet, I needed it in my mouth. I pulled his trunks down and let them fall to the floor. The next sight I saw nearly took my breath away. His cock was semi-hard and looked to be almost 9" long in this state. It was as big around as my wrist. I raised it up with one hand and the weight impressive. I had to taste it. I put a second hand on it while lifting it to toward my mouth. As I stuck my tongue out, I saw a milky white glob of pre-cum that had formed at the tip.

I licked the glob of pre-cum from his cock and then kissed the bulbous head. I stroked it up and down a few times with both hands while admiring its size. I held it up next to my arm and it was longer than my arm from my elbow to my wrist. The contrast of his pale white mammoth against my skin was breath-taking. I started licking and sucking on the head while swirling my tongue around it. Mike threw his head back and let out a moan as I forced the head into my mouth. His girth was so big that my lips were stretching to get it in my mouth.

I looked up at him with my big brown eyes as I tried to get more of his cock into my mouth. Mike continued to moan with each movement. I had him lie down on the bed, and I climbed back up between his legs. I resumed my position, trying to get more of his thick shaft down my throat. I only managed to get a few inches past the head before I was gagging. I spit and slobbered on it as I stroked it to keep it lubricated. I'd never seen a cock this big in real life. Fully erect now, it had to be 9'-1/2" or 10" long. It definitely defied the stigma of a white man.

I spent several minutes sucking and slurping as much of this beautiful cock as I could while he laid there moaning. I slid my top and bottoms off, exposing my tits and drenched pussy. I had to have it in me. I pulled his cock from my mouth and straddled his hips. I almost had to stand up to raise above his erect shaft because of its length. I guided the tip to my pussy and slid it up and down my moist crack. I slowly lowered myself, forcing the enormous head into my tiny pink hole. The pressure of the head passing my entrance was enormous.

I moaned with wanton lust as I continued to lower myself down. Inch by inch, I felt my vaginal walls stretching as I took his length. When he began touching my cervix, he still had a few inches exposed. The pressure was great, but slowly subsided as I worked it in and out. I was glad to be on top, so I could control the depth at which he impaled me. I developed a slow and steady rhythm as I continued to impale myself with his cock. His cock was glistening with my juices as my cream started to form a ring.

Mike's eyes were rolling back in his head as I was riding him. He grabbed my hips and attempted to impale me deeper, but my pussy wouldn't allow it. He started thrusting up into to a point that it almost hurt. I raised up from his cock and then quickly stuck it back into my mouth. I could taste the combination of my pussy juices and his pre-cum as the head slid back into my mouth. I was stroking his monster with furious intent now as I sucked it. Mike's moaning became more pronounced.