The boss had a meeting in another city to go to that would be an overnighter and asked me if I wanted to keep him company.
As it was a Friday and I didn't have anything planned for the weekend , I told him that I was game as long as he bought me a steak for dinner. He laughed and told me that wasn't a problem since we would be having a supper meeting with the client Max and he figured Max would probably pay for the meal. Nice.
He also told me that Max was our only business so after dinner we were free to make a proper night of it. He said he planned on having at least a few drinks at the bar. "Sounds good to me"I replied. I called the wife and told her what we were up to and we were off. The roads were in great shape which was nice to see since it had snowed the day before and we had a 5 hr. drive ahead of us. We both took our coats off and settled in for a long drive in the company truck with the boss driving.
When we got on the highway the conversation turned to sex as it always did with him.
"I hope there are a few hot chicks in the bar tonight" he said ," I need to get my balls drained".
I smiled and nodded saying "that would be nice. I know how cranky you get when you don't get it".
He went on to say that he hadn't had as much as a blowjob in three weeks.
"Three whole weeks?" I laughed and told him that I found that hard to believe since he was such a horndog.
He looked over at me and shook his head, "Ya I just haven't had a chance to go get some".
I said "Then I know who you fucked last".
Three weeks ago, my wife and I had a threesome with my boss so that was an easy guess.
" That was great" he said as he looked straight ahead. I could use her lips on my cock right now".
I looked over and he was rubbing the head of his dick through his black unifom pants. It was very pronounced and obviously hard.
He looked at me and said " I remember your lips wrapped around my cock that night too".
I smiled and said " I remember that too, It was tasty, Tasted like my wife's cunt"
"You want to taste it again?" he asked.
"As long as you don't put us in the ditch" I answered as I lifted the armrest between us. He smiled and started to undo his pants and squirm around until his hard cock popped into view. I sat back and watched as he stroked it slowly . He stopped to reach down and adjust his seat back as far back as it would go and then went back to stroking. I took my baseball cap off throwing it into the back of the truck and lay across the seat with my head inches away from his dick, He was still stroking it and a large drop of precum sat on the massive crown. I reached out with my tongue and licked it off swallowing it down, MMMM he moaned as I took his cockhead in my mouth moving slowly downward. He took his hand off his cock as I grabbed it in mine, then he put his hand on the back of my head.
"Too bad I didn't know that you were a cocksucker before" He said " I could have had a lot of blowjobs over the last couple of years"
I lifted my head and replied " All you had to do was ask"
"Shit" he said as I pumped his shaft slowly occasionally licking the precum off the purple helmet.
After a few miles of this he pushed on my head and said " Suck it" I opened my mouth and took at least 5 inches of his fat shaft down my throat gagging and came back up to just the head. I ran my tongue around the rim of his fat head while sucking hard. I began to bob up and down in his lap while he pushed gently on the back of my head moaning " Ya MMMM Thats the way, Suck my Cock MMMM"
"Wow , You are almost as good at sucking my cock as your wife, I'll have to give you a little more practice"
I mumbled around his cock as he pushed my head a little quicker and harder.
I pulled my head up and licked from his cockhead down to his furry bag lifting it with my hand so that I could suck one of his big balls into my mouth. I rolled it around sucking gently. After a minute or two , I repeated the process with the other one.
"Oh fuck that feels good, There is a lot of cum in there for you to swallow" he moaned.
I licked the underside of his throbbing cock all the way up to the top and swallowed his head and 2 inches of shaft starting to bob up and down again slowly.
"I'm getting close" he moaned "Suck Suck my cock cocksucker" he started again pushing on the back of my head.
I could tell that he was very close. His balls in my hand had drawn up into the top of his sack and the head of his already fat cock seemed to be swelling even bigger in my mouth.
He began almost chanting in rhythm to his pushes on the back of my head..."SUCK SUCK SUCK SUCK Here it comes cocksucker"
As he said that, he pushed hard on the back of my head as a massive spurt of hot cum exploded into my mouth followed by at least 6 or 7 more. I swallowed as fast as I could only losing a drop or two which rolled down his shaft coming to rest on his bag. It took a few minutes of my gulping his cum down and sucking his fat spasming cockhead before he released my head. I lifted my head taking a few deep breaths before licking the escaped cum off his bag and shaft. I popped his cock back into my mouth sucking hard causing him to jerk in his seat. "Cut that out or we might end up in the ditch" He laughed as I released his cock and sat up wiping my lips.
He wiggled to get his pants back up as I reached back to retrieve my hat and put it back on.
" Holy Fuck, I wish I had asked you to do that years ago" he said as he zipped up.
" I wish you had" I replied looking around and realizing that we were almost at our destination.
He said "we have just enough time to check in before we meet Max in the dining room".
We pulled into the hotel and found our room with two queen size beds. I used the bathroom checking the mirror to make sure that I didn't have any stray cum on my face.
We had no sooner sat down at a table in the dining room when Max strolled in. A fat Italian man with a big beard and hearty laugh.
He was a longtime client of the company and I had met him before and liked him a lot.
Handshakes all around and we ordered drinks and they got right down to business. They passsed their phones back and forth talking all the while as we went through 3 drinks each before ordering dinner. By the time we were served our steaks , they had figured out what we had come for and put their phones away as we ate.
"So how was the trip?" Max asked making conversation.
"Fucking Awesome " my boss answered as he put another piece of rare steak on his fork.
"I don't hear that very often" Max said "What made it so awesome?"
I almost choked on my steak when my boss looked at me and asked if he could tell Max about out trip.
I thought for a minute and shrugged saying " why not"
Max was looking at me questioningly as my boss said " Stan here sucked my cock for about the last hundred miles"
Max looked stunned, took another bite and looked to be thinking hard as he chewed.
" Wow, how long has he been doing that?" Max asked my boss.
"It's actually only the second time" he answered " But it's the first time he's swallowed my load".
Max looked at me and asked "What brought that on Stan?"
"Well to be honest, I have sucked a couple of cocks before and 3 weeks ago while he was fucking my wife I was horny enough that I decided that I wanted to suck his fat cock too"
Max almost choked on his drink. "Fuck I wish I had an employee like you" he said as he took another drink and waved the waitress over for another.
No one spoke as we finished eating .
As we were finishing our drinks and Max put his card on the table, I asked Max if he wanted to come up to our room and have another drink. " I was gonna head home but I will if I can get me one of those blowjobs" he said quietly.
"You bought me a steak so you might just get one" I replied.
After the bill was paid, we proceeded up in the elevator to our room. The boss opened the door and the three of us stumbled in, Max sat on one of the beds while my boss got a bottle of rye out of his bag and mixed three stiff drinks. Max asked how this was going to go as he had never had a man suck his cock. I replied that it would go however he wanted it to, " do you want to lay on the bed while I suck you? or do you want to fuck my face while I kneel in front of you? Or..." Max laughed and said "I think I like the sound of door number two"
"Alrighty" I said as I accepted a drink from my boss and knelt on the floor in front of Max. He undid his pants before taking his drink and stood,his pants falling to the floor as he stood. He shook his underpants down to the floor with his pants revealing about a 5inch semihard cock with the head hidden by a drooping foreskin, his big belly almost hanging over his tool. he shuffled forward a bit so I could reach it easier. I cradled his small ballsack in one hand and stroked his cock with the other. " It's been a long time since anyone but me has done that" he said " It feels great"
" Wait till he gets his lips on it" my boss said as he pulled his pants off and settled on the other bed, his head at the foot of the bed so he could watch. He slowly stroked his own growing cock.
As I stroked Max's tool it grew in my hand. I suspect if it wasn't surrounded by fat it would be larger than my bosses 8 inches.
I slowly lowered my mouth around the head and sucked his cock into my mouth as I fondled max's balls between my fingers. I had to sit back on my legs to lower myself out of the path of his fat belly as he started to fuck my face slowly. He reached down and held my head between his beefy hands as he plunged his still growing tool into my mouth.
My boss was telling me to suck that fat cock. "Suck it Stan...Suck his cock like you sucked mine"
He urged Max on " fuck that cocksuckers face...Fuck him..Fuck his face good"
Max started to pick up speed as he responded to the urging. He started pumping his cock deeper and faster as I struggled to breathe through my nose.
My boss meanwhile was pumping his own cock on the other bed as he told Max " keep fucking his face and pump your cum straight down that cocksuckers throat"
Max did just that , with a bellow he pulled my head to his fat crotch and pumped what seemed like a gallon of cum into my mouth, Spurt after spurt ,he just kept cumming as I swallowed furiously trying to keep up. Finally he stopped squirting and slumped backwards onto the bed.
As he did my boss stood in front of me and fed his fat cock into my panting mouth.
"That was so fucking hot to watch" He said " I'm ready to feed my cocksucker another load"
He grabbed the sides of my head and furiously pumped his cock past my lips over and over until he grunted and said " swallow this one too cocksucker" as he pumped his second load of the day into my belly. I sucked and swallowed and licked until he too fell backwards on his bed still stroking his cock.
Max stood and pulled his pants up while saying that he had to go but looked forward to our next visit to the city. I stood and shook his hand as he scooted out the door. After I closed it I pulled off my pants and walked over to my bosses bed with my hard cock leading the way.
The boss looked at my hard cock and reached his hand out gripping my shaft slowly stroking it.