Before last weekend, you could say I was going through a bit of a dry spell. I started my own tech support company, myself as the only employee. My services were in pretty high demand, but it cost me much of my social life. Suddenly, one Friday night, I hook up with a super cute guy on some dating app and the next morning have some unexpected fun with one of my best clients. I guess some would call it a really lucky weekend. That is what I thought! And by the end of Sunday, I had gotten the name of that guy who owned the bed. Sam and I started flirting a little bit by text. Of course, I felt a little guilty still about hooking up with Jim, that hot client of mine. Even though he said that everything was okay, I knew I had crossed into a grey area. Little did I know that I would be living in this grey area for a little while... and enjoying every minute of it!
That Monday started out like most others. I looked at my week, what maintenance needed to be done on my accounts and what times I had free to set appointments, possibly make some sales calls. About an hour into my day, I got a call from a guy named Tim.
Tim, like many of my clients, ran a business from his home. He is a consultant and had a business partner named Mark.
"Our old tech support wasn't cutting it and a friend of ours referred us to you," Tim explained.
"Really? That is excellent. May I ask who?" I asked.
"Oh shit! Is Jim trying to get me to fuck him again?"
Is what I thought.
"Jim is a great client! I'm excited to come see your set-up and see what we can do!"
Is what I said. Regardless of how I felt about that little fuck sesh with Jim, business is business. We set-up a time the next day for me to go over to Tim's place and see their office set-up.
Tuesday morning, after going through their office, seeing their tech, Tim invited me into his garage to play some pool and "go over the details".
Tim and Mark were quite the handsome pair. They had been in business together for about 5 years, after having worked together in a larger consulting firm. And their looks alone could keep their business afloat. They were both in their mid-thirties. Mark was about 2 inches shorter than me and a little fuller. He was super clean cut, looked like he shaved the minute he saw stubble, and seemed to be the kind of guy that was more comfortable in a shirt and tie than the simple khakis and designer tee he had on today. But don't get me wrong, Mark wasn't all business. He had this playful side that just needed a beer and a dirty joke to get out.
Tim was about my height, slender and toned. He was a little more rugged, sporting that constant scruff on his face. And Tim was smooth and quick to smile a sexy grin that probably had all sorts of women and men wet. He was wearing a pair of comfortable jeans and a ribbed tank, but it didn't make him seem any less professional. You could tell that Mark was the brains, and Tim was the salesman.
After a round of pool and a couple beers, we were getting to the end of negotiations.
"So you would maintain the office equipment and supervise the website?" Mark asked, summing things up.
"Yes I will," I responded. "And anything extra we can negotiate along the way. You will see that I am fair and easy to work with. I can probably go home and write up the contract for you to review this afternoon."
"There is one service that we didn't talk about." Tim broke in, punctuating his remark with a masterful shot. "Jim mentioned to us that you may be willing to help us with some other things."
I nearly dropped my pool cue. "What?!?"
Mark was quick to step in and cover for his partner. "What we mean is, Jim mentioned that you guys... have had a little fun together on the side. Not connected to your business at all. And when he showed us your website and Tim and I saw your picture we... thought..."
"Wait!" I stopped him. "You two are more than just business partners?"
Tim walked around the table to stand next to Mark. He rubbed Mark affectionately on the back. "We've been together for a while, since before we left our old firm."
"And you're wanting me to..."
"Well," Mark started to explain. As he did so, Tim continued to rub him, growing more sensual in his touch and nuzzling into Marks neck. "Tim is pretty versatile. But I'm more of a..." Mark stifled a soft moan and tried to maintain his composure as Tim kissed his neck and started to grind into the back of him. "I'm all bottom. Jim got the impression that you were vers yourself and maybe would be willing to have some fun with us when Tim is in the mood to bottom. You know, outside of our business relationship. We had something similar with another client, but he moved away and..." Mark faded out for a moment as Tim ran his down his chest and rubbed his crotch. Mark moved his head back and Tim and Mark kissed a deep, passionate kiss.
This sudden request and Tim's display as he kissed and rubbed Mark had me aroused. I mean who wouldn't. But even as I was growing hard, I knew that this was that grey area that I went into with Jim and told myself I wouldn't go there again. I leaned against the pool table, so my growing dick wouldn't be quite so apparent.
"I... I just don't know..." I stammered.
Tim looked up at me and smiled his sexy smile. He came over to where I was leaning on the pool table and put his body right next to mine. His chest was against my chest, I could feel his already hard cock against my hip. I didn't notice it before, but he smelled so, so sexy. He started to kiss my neck, right above the collar of my shirt. He slowly kissed his way up to my ear, all while grinding his hard cock into my hip and using a free had to find the hardon I was trying to hide. He bit my earlobe just as he found a loose section at the top of my jeans, reaching down into my boxers and grabbing hold of my now throbbing dick.
"I'm in the mood to bottom right now." Tim whispered in my ear. Then he went back to nibbling on it. I closed my eyes Tim's sexual energy charged through my body.
I thought about trying to regain some composure. But then I thought... why?
"Okay," I said. Smooth! "um... (moan) what about..."
"Mark," Tim explained, "is going to watch you fuck me. I want him to see you fucking me hard."
I opened my eyes and looked over at Mark. He wasn't his nervous self anymore. He had actually already unbuttoned his pants and was playing with a decently sized cock that was growing underneath a pair of grey, cotton boxer briefs. Mark smiled at me and playfully said, "I want to watch you ride him like he rides me. Make it a little rough" and he tossed me a wink.
That little bit of permission was all I need to give in fully to the situation. I moaned and writhed slightly as Tim continued to kiss my neck, bite my ear and play with my dick. I reached down the back of his pants and started to rub and squeeze his ass. This started to get him a little more excited and Tim moved so he was right in front of me and kissed me full on the mouth.
I love to make out with men who have a little scruff. Generally they tend to be more passionate kissers, nothing sucks more than making out with somebody who kisses like a dead fish. Also, they can sometimes be more aggressive than a clean-cut guy. I like it when they bite a little or pull on your hair or suck on your neck like they're going for blood. And also, I love the feel of their rough stubble on skin. Tim was every bit the scruffy kisser. Mark was a lucky lucky man.
I was fully into him when Tim started kissing me. I could have made out with him for hours. On top of the incredible kissing, I could feel his hardon grinding against mine, both wanting to be let out for some fun. I wanted to feel more of his skin. I pulled off the polo shirt I had on and then almost ripped his tank top off his body. His chest was hairy but well groomed, a nice bit of curly hair that all pointed down to that bulge in his pants. God I wanted to get at that cock!
I reached down into Tim's pants but his crotch was so swollen that I couldn't get in. So I unbuttoned his jeans and his pants nearly burst open, the force of his massive cock unzipping them. I was given a nice surprise ... Tim wasn't wearing any underwear! And he had a massive uncut dick! No wonder he was the top! I tugged on his rigid cock with one hand and continued to rub him with the other.
At some moment during all this kissing and jacking Tim's cock, my pants had gotten around my knees and my ass was hanging halfway out of my boxers. I was a little self-conscious because I was wearing a pair of loose baby blue boxers... the kind that are super comfortable but something I would only wear to work, not fuck (and definitely not if I was trying to impress a client!).
Obviously Tim didn't care because he was moaning to the rhythm of my hand rubbing his cock and sucking on my neck. He started to finger my ass and I started to get the feeling maybe I was going to get all of that massive dick when I heard Mark start commanding us.
"Get on your knees Tim. Get him ready to fuck you!" I looked over and Mark was draped across a chair, completely naked and slowly stroking himself. His cock was even larger than Tim's! God! I couldn't even begin to imagine these two beasts fucking.
Tim obediently got on his knees and pulled down my boxers. He was no slouch in the oral department! He slowly took in my throbbing cock, getting it nice and wet from his spit. I didn't think I could get any harder but I did as he deftly swirled his tongue around the head of my dick.
"Tell me how he tastes" Mark demanded. "You like that cock, don't you? You little cock sucker."
"Fuck, he tastes so good!" he said, pausing to look up and grin that devilish smile. Then he went into a hard rhythm, using a hand and his mouth to pump on my cock. I was nearly about to burst when Mark instructed Tim to stop.
"Now I want Tim to take it in the ass." Mark instructed, jacking off his own cock to the beat of Tim sucking on mine. "Put him on the pool table and give it to him hard."
Tim stood up and kicked off his jeans. As he climbed onto the pool table, I stepped out of my pants and boxers. My cock was nice and slick from Tim working it with his hot wet mouth. Tim laid down on his back. I positioned myself in front of him. His ass was already a little lubed up from sweat, but I added a little more with some of my sweat. Mark's total domination of our fucking got me in the mood to play it rough, so I didn't really try to ease myself in. I gave it to Tim all the way with my first thrust, my abs pressing against his ass and legs.
Tim groaned loudly, a mix of pain and pleasure. Mark came and stood next to me, put his hand on my back and said: "That's right! Give it to him!"
I started to thrust hard and steady, you could hear the soft slap of my balls slapping against his ass. Tim moaned with pleasure at each thrust. He had his hands on the table and just let his own hard cock swing wildly as I slammed him, occasionally it slapped hard against his own abs. Tim had that look on his face like he could cum at any second. I was pretty sure I was going to see the man cum without anybody working his cock.
Mark could see it too and knew just what to do. He had been rubbing my back and playing with my ass with one had while vigorously working his huge dick with the other. When Mark noticed that Tim could possibly cum, leaned into me and kissed me. It was a long passionate kiss. This elicited a loud moan from Tim. I turned just in time to see Tim shoot a huge load of cum from his wildly swinging cock. He shot several times and it got everywhere: his face, his chest and on the pool table.
This sent me over the edge. I pulled out of Tim and shot my own load all over him. My first shot of jizz landed on his face and then on his chest and abs, mixing with his own. Mark climbed on the table and knelt next to Tim. He finished himself off, shooting his cum onto Tim's chest. Poor Tim was a mess. But he just smiled, ran a finger through all of the cum and stuck it in his mouth.
He winked at me and said, "Tastes like we have a deal."