Loser Takes All

It was my first job out of college and I was determined to make good. I felt I was on the "fast track" when the owner of the company invited me to join him and two important clients on a sport fishing trip to the Louisiana gulf coast. It was made clear that I was to be a "go-fer" with benefits, that is my job was to see that everything went smoothly and do any heavy lifting or dirty work if the need arose. That was fine with me, I would still get a nice vacation and make serious points with the boss.

The "Boss" was a bull of a man at least a foot taller than my 5'6" and probably a hundred pounds heavier than my 160, not the least of it in a generous paunch. He was about 55 years old and balding, one of those "comb over" guys. He considered himself quite the ladies man and had a reputation as a skirt chaser. It must have been his money because he was always bragging about how much "tail" he was "nailin".

I myself was nearly a virgin, I had "done" it just once, in the back seat of a rented limo on prom night. I had been drunk and not, I'm afraid, very good at it at least according to my date a girl with, apparently, considerably more experience than I. After she had publicly discussed my, uh, "short cummings" I have been a little shy about repeating that debacle.

Back to the trip; We met the clients, Bill and Joe, at the airport where we were to board a charter flight to New Orleans. The were pretty much like the boss in age and temperament if not build, one short and heavy the other tall and thin. They left me to take care of the baggage and proceeded to get the party started in the lounge. They were drunk by the time we took off and kept me busy assisting the flight attendant hustling drinks all the way to our destination. What followed was a kaleidoscope of strip clubs, bars and night clubs. It was almost daylight when we finally went back to our hotel. I was exhausted.

I awoke and looked at the clock and groaned. It was only noon and the boss was pounding on my door. Time to load up the rented SUV and head out to the fishing cabin he had rented for the week. It was on a remote bayou with only a generator for power. The guide would pick us up every morning in his boat and take us out into the Gulf. Since they were still drunk (and still drinking) I drove. Thank God for GPS or I would have never found the place. It was, as near as I could tell, on an island with only one bridge.

The owner met us, showed me how everything worked and the went on his way. We were amply supplied with food and booze (I rarely drink; remember prom night?). There was even a big screen tv with satellite and a pile of porn movies for the dvd. So far I was sure having fun! That's sarcasm if you missed it. By this time it was getting dark and after whipping up a quick meal that nobody ate we turned in. Thank God.

We were all up at dawn and out on the Gulf by 8:00. Luckily no sea sickness. and we caught a few fish. It was almost dark by the time we got back. Thankfully the crew of the boat cleaned and cooked our catch before they departed. Boss and cronies were drunk and I was exhausted. This was turning into the most work I had ever done on a "vacation".

Before he left the Skipper warned be that a storm might be brewing and that we might have to cancel the next days outing. He would see us in the morning if he thought it was safe to go out.

That night it did storm. One hell'uva storm and sometime in the night the generator conked out. No power, no cell coverage and when I got there, no bridge! We were stuck. It rained all day and into the night. All there was to do was play poker by kerosene lamp and drink. I was terrible at both.

I think everyone was getting pretty bored and the guys started talking about our night in New Orleans and the various attributes of the strippers they had gotten lap dances from. It was pretty obvious they were getting horny, as the talk got raunchier an raunchier. By now even I was sipping on some scotch and getting kinda lit.

Finally the boss said that he couldn't take it anymore He needed some relief, and someone was going to have to "take one for the team". I wasn't sure what he meant but I had a bad feeling. One of the other guys said he felt the same way and looked pointedly at me.

The other guy suggested we cut cards to see who would "provide the service" (wink; nudge).

I started to sweat and glanced at my boss. He was just leering at me and then I knew. I knew what they were talking about!

Everybody agreed (I didn't feel I had a choice) that low card would be the "provider". Boss cut first and drew an eight. Bill next and whooped when he drew a ten. Joe's hand was a little unsteady as he chose and groaned when he cut a five. Boss was smiling now and then he looked at me menacingly.

"Your turn" he said and held out the deck. His eyes were boring into mine and I knew what he wanted. "Don't fuck this up" they seemed to be saying. "Remember! The client comes first!"

My mouth was dry and my hands were shaking as I reached out. I knew what the boss wanted of me and if I read his eyes right I knew my future hung in the balance. I cut the deck and looked carefully at my card. Three sets of eyes watched as I gently slipped a queen face down back into the deck.

My voice shook as I all but whispered "I lose".

Three voices whooped loudly as they slapped each other on the back. The tension was broke for them but I thought I was going to be sick.

The first thing they had me do was strip. I felt embarrassed to be naked in their presence and it only got worse as they had me scamper around fetching drinks while they took turns smacking my ass and commenting on how hairless my body was. Comments such as "Hell he even looks like a girl from behind", "Even from the front!" and "You sure have a pretty mouth" brought roars of laughter

Next they cut cards to see what order I would "service" them. It was to be Bill then Joe then Boss.

Bill stepped up and motioned me over. My head was swimming as he put his hands on my shoulders and gently forced me to my knees in front of him.

"Come on son, you know what to do" he said and placed my hands on his belt buckle. "I want you to look into my eyes the whole time" he said softly "I want to see your eyes as you suck my big cock. Now take it out!"

It felt like I was outside my body as I undid his pants an pulled them down. I couldn't help but glance at his cock as it came into view. "Look at ME!" I looked back up. That one glance had told me it was long and thin much like Bill himself and only semi-hard. He flexed his hips forward with a grin and bumped my lips with his cock.

"Give it a kiss, son. Kiss it real nice."

I leaned forward and kissed the shaft. The texture was smooth and there was a musky scent in my nostrils. It twitched slightly and I jumped like I was bee stung. He laughed and said "It won't bite you, son. Just make damn sure you don't bite it! Now get on with it. Take it in your mouth and suck". I noticed the room was quiet and I wanted to look around to see what the others were doing but my eyes stayed locked on Bill's as I leaned in again and took the head of his cock into my mouth. He groaned and somehow that pleased me. Leaning farther in I tried to work up some spit as I took more of him into my mouth. He pulled back slightly and then flexed his hip again forcing more of his cock into my mouth. This time I groaned. Then he rested his hands on my head and started to fuck his long, slim cock into my mouth, each stroke going a little deeper than the last, all the while looking into my eyes. He soon reached the back of my throat making me retch. That brought a chuckle from behind me. Bill backed off slightly so I didn't choke and I was grateful for that. I realized that I now had one hand stroking his shaft and one on my own cock.

"Oh my God! I was hard and I was jerking off while a man fucked my face!" I thought as I blushed with shame. Bill saw the emotions sweep over me and smiled. Slowly he put more pressure on my head and steadily forced his cock deeper and deeper down my throat. He was good at sensing when I was about to gag and withdrawing. With wonder, I realized that he was teaching me how to deep throat cock as he went along. It seemed like an hour, but probably wasn't, when I managed to take him all the way down. I could feel his pubic hair tickle my nose and saw his eyes sparkle as I slowly withdrew off his cock. I had a strange sense of pride and slipped back until just the head remained in my mouth. Then sucking as hard as I could I started back down. His eyes were starting to get a glassy look to them as I swallowed his big dick over and over, faster and faster. With a groan he started sinking to his knees pulling away from me. I panicked and used both hand on his ass to try to keep his dick in my mouth. I was confused. "Why was he taking his cock away from me"

But he wasn't. He was just re-positioning so that now I was on my hands and knees between his legs as he lay back on the floor. It had the effect of forcing my ass up and I became aware with a start that Joe was behind me. I started to panic again and I heard Joe tell him to hold me. Bill grabbed my ears and forced his cock down my throat and Joe smacked my ass hard and told me to "behave". I felt a cool liquid being pored over my ass and then a hand gently massaging my buttocks. It actually felt pretty good and I started to relax a bit. I heard Joe murmur "He does have a nice ass" he mused, "Hell I think it's better than my wife's! " That brought a chuckle from Bill who relaxed his grip on my ears and allowed me to continue sucking him off.

I felt a finger start to probe my asshole. Luckily it was well lubed and before I knew it it was sliding in and out. Just as I was getting used to it it was joined by another. That was uncomfortable but Joe was taking his time and I was slowly stretching to accommodate them. By now I was trying to concentrate on Bill's blowjob to take my mind off what Joe was doing to my ass. The term "sloppy" could certainly be applied. For some reason I was drooling like a faucet. With little nudges from Bill I would vary my pace, sometimes short and quick, sometimes deep and slow. I thought Bill had amazing staying power. He was obviously enjoying my "services"and I could hear him moaning as I lost myself in the moment. My whole world seemed to be that cock .

That changed the second I felt the tip of Joe's cock touch my asshole. I felt a stab of pain and stopped sucking as I tensed up. "Just relax" someone whispered. The cock in my mouth twitched and I went back to sucking to try to take my focus off my ass as Joe's big cock pressed harder and harder against my poor sphincter. Sweat broke out on my forehead and I could hear an agonized wail that I realized was mine. Then, with what I can only describe as a "pop", the head of Joe's cock entered me. Luckily he stopped to allow me time to adjust. After a few moments Bill nudged me to continue and then Joe slowly started to shove what felt like a telephone pole up my ass. The deeper he went the harder I sucked, trying desperately to take my mind off my ass. Just when I thought he must be all in and it couldn't get any worse he started to pull out. I thought he was taking my insides with him. Now tears were mixing with my drool on Bill's cock. With only the head still in me, Joe reversed course and started back in, slow but firm and steady. This went on forever and it came as some surprise to me when I realized that the pain was greatly diminished and what I was now feeling was alternately the sensations of full then empty, full then empty.

Before long Bill got back up on his knees and with his long thin cock in my mouth and Joe's shorter, fat cock in my ass I had the sensation of one huge cock running clear through me. Bill would pull me forward burying his cock down my throat then Joe would pull me back burying his cock in my ass. Over and over until finally I was throwing myself back and forth on that huge single cock. Faster and faster I went until Bill and Joe were just holding on for dear life.

My cock was as hard as glass and I could feel myself close to cumming. By the sounds of the moans coming from Bill and Joe they were close too. Finally Joe reached around and grabbed my dick between his thumb and forefinger and gave it a little tug. That was all it took. I shot off like a geyser. With a mighty shove by both Bill and Joe, they too started to cum. Bill was groaning as he shot spurt after spurt of cum down my gullet. I didn't even have to swallow, he was that deep. I felt a little disappointed that I wasn't able to taste my first load of cum but he pulled out enough that the last couple of spurts landed squarely on my tongue. Perversely, I savored the taste. Simultaneously I could hear Joe snarling like a pit bull as he slammed into me and dumped what felt like a quart of cum in my ass. Spurt after spurt of deliciously warm cum flooded my hole and I wiggled my hips like a bitch in heat to get it all! We all collapsed in a pile, me on the bottom laying in a puddle of my own cum.

I slowly became aware of my surroundings. I was still nursing on the head of Bill's cock like it was a baby bottle. With a chuckle he slowly disengaged and patted me on the head like I was his favorite puppy. He actually said "Good boy!" as he got slowly to his feet. I groaned with humiliation. Joe and I were still tangled up and even though he was still buried in my ass I could tell his cock mad shrunk. I was not nearly as full. With a moan he pulled out and I could feel his warm sticky cum run out of my gaping asshole. I instinctively reached down as if to stop the flow and was shocked when I could stick my index finger in without touching the walls of my sphincter. I scooped up some of the mess and brought it too my lips catching myself just in time before licking it off. Joe caught the gesture and I blushed. He rolled over on his back and, grabbing me by a hand full of hair, he pulled my face over to his cock.

"I'll give you a taste, you little faggot!. Get your lips around it and clean me off!" he snarled.

Burning with shame and humiliation I did just that. In fact once I got started he had to finally push me away. I don't know what came over me. I just couldn't stop sucking, I know it was disgusting, I mean his cock had just come out of my ass but I couldn't help myself.

He finally got up and left me, joining Bill at the bar for a tall scotch. I lay where I was in a puddle of my own spunk.I heard a growl and looked over to where Boss was sitting in an overstuffed chair. He was completely naked. I took one look and knew it wasn't "just" his money that attracted women. Standing up from between his hairy legs was a huge cock. It looked at least a foot long (its actually 11", I've measured it!) and as big around as my wrist. The veins stood out from the shaft and the head, the size of a lemon, was an angry purple color, in fact, angry was the way I would describe the whole thing. His body was practically covered in thick hair which made his baldness ironic. In spite of his gut he was powerfully built.

I found myself both intimidated and strangely thrilled when he held out his hand and crooked a finger at me to come. I crawled (it just seemed "right" to crawl) over to him and kneeled between his thighs when he spread them. I assumed he wanted me there but he surprised me by gesturing me up onto his lap. It was like sitting on Santa's lap when I was a child except of course this Santa was naked with a huge hard on. He wrapped his big arms around me and drew me in in a hug. He was very gentle and as he hugged me to him I felt very warm and secure. He murmured how proud he was of me and how he was going to take "good care" of me and I was going to be his little "slut" boy. He said he had known from the start what kind of a boy I was and that he would see to it that I got all the "yummy" cock I could handle. Then he kissed me. A deep soulful tongue down my throat kiss that left me breathless and my "little dickie" (his description) throbbing.

Telling me to go pour him a scotch and get him a Havana, he gave me a swat on the ass to get me started. I don't know what came over me but I squealed like a little girl and I couldn't help wiggling my hips a little as I scampered off to do his bidding. Bill and Joe just smirked at me. Returning, he sent me off to clean up while he waited. I just took a bar of soap and stood under the eaves to shower off in the rain water.

I toweled off as I padded back to my Boss, falling to my knees between his wide spread thighs. His cock had softened and was laying across his thigh. Without being told I started to nuzzle, then gently suck on the head, to bring the monster back to life. I didn't understand it at the time but somehow I knew that I had found my place in the world. I was where I belonged.

What a sight Bill and Joe must have had as they went off to bed that night. There was the Boss, sitting back in his chair, sipping fine scotch and smoking his huge Havana while I slowly and languidly made love to the biggest cock I've ever seen.