It seemed like foolish bet at the time…on his part. Roger and I were finishing up 18 holes of golf during which we had bet something on just about every hole. Who can get a birdie on this hole, who will have the longest drive, who can get closest to the pin on a par 3, etc.
Then came the 18th hole where Roger came up with a crazy idea for a bet. Since I had last two or three bets in a row, I was almost out of cash, and he knew it. We both had reached the green in regulation but I was left with a relatively short putt of about eight feet while Roger was looking at a long putt over an undulating green of probably twenty-five to thirty feet.
“I’ll bet you I can sink this putt,” he boasted.
“No way in Hell,’ I replied, “You couldn’t make that putt in ten tries!”
“Twenty bucks says I make it in one shot!”
“I don’t have twenty bucks left and you know it,” I said. “I only have enough for a beer in the clubhouse after the game.”
“Tell you what I’ll do. If I don’t make it, I will give you the twenty, but if I sink it, you will be my slave for eight hours. You will do whatever I ask, without question.”
“You are definitely ON with that bet!” I laughed. “Maybe I will have two beers and the clubhouse special cheeseburger instead after you miss it.”
“The bet is on,” he declared as he set his putting stance above the ball. Due to the undulation in the green, he started the ball way out to the right, assuming gravity would pull it back down to the left as it neared the hole.
My first guess was that he didn’t hit it hard enough, and sure enough, as the ball travelled across the green it slowed appreciably. But then as it neared the hole, the slope of the green caused it to turn left toward the hole and allowed it to maintain speed.
I could not believe my eyes as the ball headed straight for the hole. But then it slowed, and it slowed and stopped right on the lip of the cup. I let out a sigh of relief as my mouth started to water for that cheeseburger.
“Hold on,” he cried. “You have to give it 10 seconds!”
Unfortunately, he was right, and upon closer inspection, I could see that there was just one little blade of grass keeping that ball from falling into the hole and sealing my debt of servitude. Then, at about the seven second mark, the ball slowly started to move and there was only one direction it was going…into the hole!
“Damn!” I cannot believe this has happened to me. I swear that was a one in a thousand shot for a guy of Roger’s talent and golfing ability.
“Bingo!” Roger cried, “I think you had better plan on showing up at my office at ten o’clock next Saturday morning and we will put you through your paces.
“Just what I wanted to do with my Saturday morning,” I thought, “schlepping rugs and carpet in his warehouse.”
Roger ran a carpet sales business in a small building, not far from where I lived. Over a beer in the clubhouse after the game he explained to me that I was to be his personal slave, and was to show up at his office/warehouse on Saturday morning when he was normally closed for business. I had no choice: a bet is a bet.
He had instructed me to dress casually, so I was wearing only a T-shirt, cargo shorts, underwear, and tennis shoes when I arrived at my appointed time. His business was housed with a reception office in front and a small warehouse in the back where he kept a lot of rugs, carpet rolls and samples.
When I arrived, the door to his business was open, so I walked in to find him sitting behind what normally would be a reception desk. Without speaking, he immediately, walked behind me to lock the front door then instructed me to head back into the warehouse.
This kind of surprised me as Roger was not being his jovial, happy-go-lucky self but rather acting very serious and stern. I was told to stand in the middle of an open space facing him as he sat on a barstool with a padded back and arms. Right away I noticed he had picked up a leather riding crop, which certainly made me a little more nervous about what was about to transpire.
“If you are to be in my service, I will require you to undergo a thorough inspection. You understand you are to obey every command without question or hesitation,” he instructed. “You are not to speak unless spoken to.”
“Whoa,” I thought, “What the Hell is this?” This is not at all what I was expecting, even though the bet was to be a slave for the day. But, with really no other choice…
“Yes,” I replied simply.
“Very well then, Strip! Remove all your clothes, slowly.
“You’ve got to be kidding!” I cried out. I knew the guy was a little different but this was going off the charts!
“Did you forget your instructions already? That transgression will cost you later. Now Strip!”
The guy obviously was not kidding so I slowly began to disrobe. First my tennis shoes, then my tee shirt and cargo shorts. I stood there at ease, ready for his “inspection.”
“Another transgression already? Do you not understand the word, strip?” he exclaimed. “Get rid of those briefs. Now!” He was obviously becoming annoyed.
“You want me totally naked?” I asked incredulously.
“That’s what strip means! Now do it!”
Reluctantly, I removed my underwear and stood before the man, naked as the day I was born.
“Much better,” he said. “Now we will begin.”
He slid off the bar stool and walked slowly toward me. He slowly and gently traced the outside of my arms and up onto my shoulders with the leather tab at the end of the riding crop. Then as he circled behind me, he did the same across my shoulders, down my back and over my buttocks. The light gentle touch, coupled with the suspense of what was going to happen next, actually felt good and I hated to admit was turning me on just a bit. How weird is this!
Then he slowly ran the velvety crop right down my buttcrack and down the back of my legs causing a shiver to run up and down my whole body. When he stopped at my ankles, he tapped the crop on the inside of my leg indicating I should move my legs apart for him.
When I moved my legs about 10-12 inches apart, he slowly ran the tip of the crop all the way up the inside of my leg till he was gently tapping the bottom of my scrotum, not enough to trigger a pain response but enough to know someone was knocking.
He then lifted the handle of the crop straight up in the air so that the shaft of the crop was snuggled right up my buttcrack. When he jiggled the crop up and down, the surface of the shaft played a little tune on my butthole that once again, was sending mixed signals to my nerve center. This shit was starting to turn me on.
When he came around to the front, I could see that he had quietly removed his shirt and shoes and appeared before me bare chested. Still working with the riding crop, he gently played with my nipples and rubbed the tip of the crop down towards my genitals. Skipping over my slowly emerging penis, he once again trailed the tip of the crop up and down the inside of my legs, this time from the front. Once again, he also gently tapped my scrotum which produced another notch up in my slowly engorging member.
He reached back and put the riding crop on the barstool he had vacated. Then, while standing about 3 feet in front of me, he slowly lowered his slacks to the floor and stepped out of them. He stood before me wearing only his boxer shorts.
Once again, he started to circle around me only this time, instead of using the tip of the riding crop gently massaging my skin, he used his fingers. When he was directly behind me, he started to very gently rub my shoulders, neck and ears. He ran his hands down the outside of my arms, then indicated by pulling up on them, that I should raise them just a bit so that he could reach around to caress my chest.
He held both my nipples between his thumb and forefinger and gently massaged them, then unexpectedly, squeezed quite hard and dispelled the reverie that was slowly coming over me. He ran his hands down my stomach, eventually massaging either side of my genitals without actually touching them.
At this point, I was screaming to myself for him to grab them, caress them. I was actually getting really turned on by his ministrations.
However, I was to be denied, as he brought his hands around to my back, gently, rubbing them up and down my back and down onto my butt. For a few seconds his hands were not touching me but with the noises I could hear, I could only assume that he was removing his boxer shorts.
Next, what was a gentle motion on my butt crack was so obvious it was not his hand, but rather his now-rigid cock. I had to admit it felt good, but I really was hoping not to lose my anal cherry on the floor of a carpet warehouse.
Thankfully, he moved around in front of me again, gently stroking my cock and fondling my balls. By this time, I was at full rigidity, as was he.
He looked at me with a smile on his face, acknowledging his ministrations had accomplished their intended purpose. “So now,” he exclaimed, “let’s deal with those transgressions.” Ooops, I had forgotten completely about them.
He reached back to the barstool and grabbed the riding crop. Taking careful aim, he swung the crop, causing instant pain to my already throbbing cock. He had struck it directly in the middle of the shaft, and the pain was pretty intense. The second stroke was upward and landed squarely on my scrotum. Now that really hurt!
He instructed me to turn around and bend over, facing away from him. Then began an assault on my butt cheeks, striking each one with what I perceived to be pretty hard strokes from my left to my right. By the time he reached 10 strokes on either cheek, I was not only flinching with each stroke, I was calling out in pain, and begging him to stop.
He finally stopped, and as I turned back around to face him, he stood there with his still rigid cock in his hand and gave me the succinct order, “On your knees!”
Well, I had never sucked a cock before, but I guess there’s got to be a first time for everything. My heart raced with a mix of fear and excitement. I’d fantasized about taking a stiff cock in my mouth, but this was happening so fast that my mind was a swirl of unfinished thoughts.
My eyes were wide as he slowly moved forward, his large, swollen cock and balls now inches from my face. He reached out, putting one hand on either side of my head. Slowly, gently, he pulled my face directly into his warm junk, his balls pushing against my mouth and nose, his throbbing cock resting against my eyes and forehead. Breathing in deeply, the earthy smell of his junk infused me with a desire to embrace him and take his cock deep into my throat.
I reached around, grabbed his ass cheeks and pulled him into my face. I licked his balls then slowly moved my tongue up his shaft. Finally, my tongue found that beautiful, warm and throbbing head! I couldn’t wait any longer! I devoured that cock in one fell swoop, taking him into my mouth and down my throat. My head bobbed up and down on his shaft, going deeper, and deeper with each downward push. And there it was – my face was fully buried right up to his groin. I reveled in that moment of full connection, my nose pushing into him while his cock filled my throat.
With my face firmly implanted in his junk, my right hand gently caressed his balls. I began sucking his cock up and down slowly. As I bobbed my head, I swirled my tongue around the head of his cock, and turned my face back and forth to massage him toward orgasm.
Hearing him moan with pleasure told me I was giving him exactly what he wanted. I was actually starting to enjoy this and I could have continued sucking his cock forever. Now with my hand firmly around the shaft of his cock, moving up and down in concert with my mouth, I increased my speed to match his moans. His engorged head throbbed against my lips and in my mouth.
“Ahhhhhh!” he cried out, as he pulled my head deeply into his groin. His cock exploded its warm reward, filling my mouth and throat. I held him deep inside me, moving only very slowly as his quivering body delighted in the ecstasy. I continued to suck him gently, swallowing every last drop of his deliciously warm cum. When the quivering subsided, I looked up and just smiled at him.
We were both spent. He sat back on the barstool; I sat quietly on the floor. No one spoke for several minutes, then he grabbed his clothes.
“Well, you passed inspection. The bathroom is the door to your right in the front office. You can clean yourself up and see yourself out. I will be in touch to set up our next appointment to complete your eight hours of service.”
I cleaned up, got dressed and quietly left, wondering how I felt about that next appointment; mortal dread or nervous excitement and anticipation?
