Training Chris And Mark Ch 08

Finale -- Fucking Chris and Mark

When I first noticed the two hot young guys following my friend Blake through the bar Friday night, I knew their scene instantly; straight guys out for pussy but willing to sell themselves to a man for the right price. I was a gambler and didn't mind sitting in on that game when I sensed I'd walk away with the pot by its end.

I took straight blond Chris home with me that first night. Before I did, I asked him if he was my bitch. He got upset at that and went into a long rant about being straight and only letting men suck his dick for money. I listened but didn't comment. During the drive to my home up in the Hollywood Hills, I had him slide his jeans down around his feet and stroke his cock for me. When we got there, my long-term boy Ron broke Chris and trained him for me a bit.

It's always amazing how easy it is to do that with a lot of these straight guys who fancy themselves to be alpha studs. It took less than an hour to discover how talented the straight young roofer's mouth could be when he was motivated. While Chris was down on my cock, demonstrating to me how motivated I'd made him, I again asked if he was my bitch. I had to ask three times before I was sure the loud gagging, choking, mumbling sound I heard coming up from my crotch was Christopher assuring me that he indeed was.

Very early morning, after stripping away the hair around his cock, balls, along his taint and very carefully, while teasing, petting, and occasionally probing his tender asshole and caging his always hard cock, I took him home to the apartment he and his dark-haired friend, Mark, shared in the Valley.

During a video chat Saturday night after the boys had rested and Chris had a chance to share with his roommate the details of the arrangement I offered them and which he had accepted for himself, Chris helped me prep Mark for his takedown.

Getting into Mark's head was easier than I expected. I knew when I saw him laying back on Blake's sofa Friday night with his eyeballs all but rolled back up in his skull as Blake sucked on his cock that he was controlled by his dick. Still, I had no idea of the extent to which that was true.

Before I knew it, the straight stud who the night before was trolling for pussy was leaning back on a chair facing Chris's laptop cam performing for me like the slut I knew he was. His long, muscular legs were spread wide as he leaned forward, looking down his body past his fingers pinching and twisting his hard little nipples over the long arcing mound of his boner still hidden by his boxer briefs into my eyes through the screen.

I waited until Mark's eyes were fully glazed before I told him to roll back onto his shoulders, lift his knees to his chest, reach back, and hook his thumbs under the waistband of his briefs. When he obeyed me and was on his shoulders with his head bent forward, looking at me between his smoothly muscled thighs over his bulging cotton covered hardon and balls, I ordered him to very slowly peel his boxer briefs down over his muscular, hairless cheeks to his knees and show me his butthole. Even though the cam, Mark's butt, spread so wantonly with his little almond-shaped honeypot deep in his crack, was as tempting as I had imagined.

Before I knew it, the straight alpha stud was before his laptop's cam lying back in a chair with his knees beside his pecs, pounding his big dick and tickling his butthole for me like a bitch caressing her pussy. At my direction, when I let Mark cum Chris caught all of his buddy's massive load in his palm, which he brought to the screen and showed to me.

With Mark still lying back, panting, Chris returned to his roommate's side, spread open his lips with his fingers, and while looking down to be sure he didn't spill any, poured Mark's load into his own mouth.

Before I ended our online session, I had Chris cage his roommate's big dick with the one identical to his own I gave him that morning. The keys to both chastity devices he now possessed would never be under his or Mark's control again after that night.

Ron and I were by the pool when a ringtone sounded on the sound system, announcing that someone was at the gate. The night before, I told the boys to arrive at my home at one o'clock. It was 12:56 a.m. I wondered if their cocks were already hardening and feeling uncomfortable in their cages.

Ron and I decided over breakfast that since Chris and Mark would be ours for the day, spending much of it "Pegging" them would be fun and an educational experience for them. During an assignment in Algeria several years earlier, I purchased and shipped two antique Pegging Planks home. I planned to keep one and give the other as a gift but never got around to doing so.

A day was not enough time to properly Peg a boy, but I was sure Chris and Mark would find enduring even a few hours on the plank memorable.

While I took the boys to the gym to prepare them for their afternoon, Ron secured my six-foot-long Pegging Planks to decorative concrete benches that faced each other on either side of the pool. Mounted on each plank were four wood pegs of graduated lengths and thicknesses. The first was a humble four inches long and only an inch and a half in diameter. The final peg on each plank, though, was not humble. That peg was nine inches tall and measured three inches across at its base. A true "Beer can dick," but taller.

Initially, in the 1700s and early 1800s, during the North African pirate wars, the arab pirates used the planks to train captured young English and American sailors before taking them to the slave markets. The boards, and more commonly modernized "pegs," have found broader and more popular uses.

As you've probably surmised, I intended to mount each boy on the smallest peg on each plank facing each other across the pool. Their cages would be replaced with a cockring like tight leather strap that encircled their ball sacks and a ring attached. That could be attached to a chain the length of each peg connected to the plank at each peg. The system allowed the peg rider to bounce his ass on the peg but not lift off it.

Before I pegged the boys, they had to be cleaned out. Ron had given Chris and Mark deep enemas yesterday. Both young guys who prided themselves on being studs at the top of their game had experienced the humiliation and the physical sensation of being naked and hairless on all fours as a man slid a greasy plastic nozzle up his ass. Now they crouched on the wet tile floor again with their backs arched and their fine young muscular butts thrust up in the air waiting for the warm rush of water to fill and possess them.

I flushed them out repeatedly, side by side. I was amused that neither of them mentioned that there was only one toilet. Watching them alternately dancing on their toes, holding their bellies, moaning, begging the other to hurry and get off the toilet was hilarious. Eventually, after I bent them over and inspected each of their assholes closely to be sure they were pristine, I knelt them down facing each other and had them jack me off with their lips.

We hadn't even made our way from the house to the pool when both guys noticed Ron on his knees finishing his work securing the second Pegging Plank to its bench. Mark first identified the plank for what it was, or at least he spoke up first.

"What's he doing?" He asked, coming to a stop and pointing. That caused Chris to stop moving and look.

"Ron's mounting pegs to those benches. You and Chris will be riding them this afternoon," I said matter-of-factly as if I was commenting on someone painting my house.

'No way. I'm not sitting on any peg," Mark said in what sounded like a definitive no.

I expected this, but not until we reached the pool. No matter. Addressing it now was fine, and it was probably better.

Turning, I said, "Chris, go to Ron. Mark and I will join you in a few minutes." Then to Mark, "I think we should talk. Let's go into the house for a minute."

Once we were inside and out of sight of the pool deck, but with the sliding glass doors still open, I spun around and confronted Mark so suddenly still moving, he almost stumbled into me, which was what I wanted. He was stumbling and off balance, standing naked and stripped of every vestige of his manhood as I stood before him looking stern, in charge, and not at all pleased with him.

"It is time you understood something, boy. Since the moment I slapped your hard dick at Blake's apartment, no, since we met at the bar that evening, I've owned you."

Mark's mouth opened as if he was going to speak, but I raised my palm facing him and ended his thought about talking.

"Your dick, balls, and asshole are shaved because I shaved them. You stroked your big cock and played with your asshole for me last night in front of a camera because I told you to. You ate your load because I wanted you to. Your cock isn't caged today because I freed it. Your ass has been pumped full of water over and over because I wanted it to be. Am I wrong?" I asked calmly and quietly.

Mark was silent for a few seconds, then acknowledged the truth of my words.

"Well then, since I own you, here's what I want you to do. Get down on all fours for me."

He looked at me questioningly.

"Really, now, down on all fours right here," I instructed again, pointing to the floor at my feet.

Mark slowly sank to his knees and then dropped to his hands.

"Excellent! You see, obedience is never difficult. Now, show me how deeply you can arch your back and lift that fine, muscular ass you've worked so hard to develop up into the air," I urged while smiling encouragement.

Squatting down fully dressed next to the naked, crouching on all-fours with his head held high and his nearly perfect, hairless ass thrust up in the air twenty-four-year-old recently straight roofer, reaching under his taunt belly to his throbbing, snapping, dancing hardon and dragging a fingertip along its underside from his balls to its already leaking tip.

"Mark, I do enjoy how your big cock gets hard the instant I start to use you. Do you think it's the use or the humiliation that excites you most? I suspect it's the humiliation," I whispered into my crouching sub's ear as I tickled the little sensitive nub of flesh on the underside of his cockshaft. At the same time, my palm caressed his upthrusted left butt cheek as its fingertips brushed lightly against his quivering pucker.

"Come, crawl outside, and let's get you and Chris settled onto your pegs," I said. "The day won't last forever, and your fine young butts have quite a bit of stretching to endure," At the same time, my fingertips tapped lightly against Mark's pouting anal lips. I repeatedly scooped leaking precum off the tip of his dancing dick and fed it to him.

Ron was seated on the far side of the pool with Chris on his knees before him, sucking his cock. Ron never failed to notice when I entered a room, even the most crowded bar. In this case, though, I was sure what caught his eye and made him speak to Chris, who lifted his mouth off Ron's cock and turned to look wasn't me but Mark crawling beside me with his handsome face held high and his ass that so many women and men lusted after thrust up high in the air.

When we reached my boy and Chris, I lowered myself onto a lounge chair beside Ron and spread my legs. Without a word from me, Mark crawled into position beside his roommate, between my legs. Ron and I talked for a while, discussing the two roofers as if they weren't present while they sucked out cocks.

After a while, when we were confident we had placed the once proud pay-for-play studs into the proper mindset, we stood up and, in doing so, yanked our drool-covered cocks from their mouths, bent them over, and lubed their assholes like the property they now were.

When our fingers had probed, explored, stretched, and lubed their tight, virgin holes for as deeply and as long as we cared to, we guided each Peg Boy to his plank. Instead of cages on their cocks, Chris and Mark wore the strap-equipped leather cockrings used to attach Peg Boys to their planks.

They would ride their pegs for thirty minutes each for two hours that day. The time would begin when each boy had slid, wiggled, or ground his ass down on his peg, and each was firmly seated on his plank. They would then perform for us by bouncing and grinding on each peg for thirty minutes before being allowed to move on to the next. To enhance our enjoyment, they were to constantly masturbate. Occasionally, Ron and I would pull a chair up and sit before them, squeezing their nuts or torturing their nipples. Sometimes, we just stood before one or the other and had them blow us.

It was late afternoon when Chris reached his fourth peg. What he offered to do or let me do if I would not make him take that nine-inch ride was not something a twenty-three-year-old straight guy should ever hear himself say. I had to remind him that only two nights before, he balked at admitting he was my bitch the first time I asked if he was. I said no; his life so far had led him to that peg. He had no choice but to ride it.

Sometimes, the most exciting sounds are whimpers, gasps, deep guttural grunts, and a man hyperventilating.

Knowing I was about to have some fun, Ron decided to jump into the pool and let me play.

I guided Chris down from his plank and, like Mark, showed him how to assume the proper all-fours presentation position. It took a little while and some heavy hand spanking of Chris's naturally hairless bottom for him to understand that when I told him that I wanted it thrust up high in the air, I really did mean high. Eventually, though, Chris accompanied me around the pool like an obedient dog to where Mark was about to complete his time on the third peg.

Watching two primo straight guys, or two recently straight ones who are friends, performing together sexually for the first time is a rare treat and one I will go to great lengths to orchestrate.

When we reached Mark, I unlacked his cockstrap from the plank and had him join Chris on all fours. I spoke briefly, and then the roommates positioned themselves in the classic sixty-nine. There was a moment when they looked as if they might balk. Me leaning forward, reaching out, and gripping each of them by their balls ended that. They instantly lifted each other's hard cocks to their lips. From then on, I enjoyed their performance, directing, encouraging, and praising when they earned it.

Chris and Mark sucked each other off for a long time. Once they got used to having each other's dicks in their mouths, I had them show each other exactly how they each sucked my cock. I wanted them both to be familiar with each other's techniques. I also had them show each other how their favorite girlfriend sucks their cock. Both guys would be sucking a lot of guys off soon. I wanted them to be able to please a variety of men.

When I was confident that Chris and Mark were orally subdued and compliant, all that remained was for Mark to ride his final peg...and for me to fuck his ass.

Mark decided to take it like a man. There would be no long, slow, drawn-out whimpering slide for him. He looked me in the eyes and climbed onto that big wood peg. I could tell from his eyes when its tip entered him and when it slid in a couple inches. I think he expected that the third peg opened him up enough to let him grit his teeth and drop himself down. That might have been, but he forgot how much time had passed while he and Chris were chowing down on each other's dicks.

I was sitting before him, holding his balls in my hand, rolling them, when Mark let his ass drop.

Nothing I was doing caused Mark to scream the way he did as his already sore and tender asshole tore down that nine-inch long, three-inch thick pole like it was trying to start a campfire. He tried to jump up, and he did lift nine inches, but the strap around his package yanked his asshole back down the pole, and he screamed again. I smiled as Mark screamed again and again, bouncing up that big wooden pole and slamming back down on it each time with his fist pounding his huge, swollen cock, over and over until I finally gave him permission to cum.

Mark's wide open, almost hysterical eyes looked straight into my smiling ones as his big bloated penis exploded ribbon after long thick white ribbon of hot baby batter into my waiting open palm and onto my wrist. His cock just kept on shooting as I reached out with my left hand a few times to pinch and twist his puckered-up right nipple and tug on it, which only seemed to make him cum even harder.

The afternoon went well. After relaxing in the hot tub and sauna, we took leisurely showers. I drove us to Geoffrey's in Malibu for dinner. The restaurant was a special place for Ron and me, and we had decided that Chris and Mark would become special to us, also. Geoffrey's is on Pacific Coast Highway on a clifftop overlooking the Pacific. Although there is a sign, those unaware of the exclusive spot often sped right past it. As I had hoped, the whales were up that night.

Mark didn't hesitate or ask a question when I told him to strip and wait for me in my gym dressing room upon our return. On my way to meet him there, I noticed Ron and Chris making drinks and appearing to be getting ready to settle in with a movie.

Routine and repetition are part of training a boy properly. Although I didn't think it was necessary, I gave Mark an enema because we had dinner. My secondary motive was to be sure that after his afternoon of pegging, his sphincter had regained enough of its snap for us both to enjoy the fucking I was about to give him. It had.

The night before, when I was watching Mark on the 72" flat screen in my bedroom, laying back his shoulders, with his head bent forward, looking at me between his thighs as he slowly peeled his boxer briefs down over his muscular, hairless butt cheeks so I could see his little asshole I decide that when I fucked him it would be in that position. When I let Mark cum and Chris caught his load in his palm and then fed it to him, I knew when Mark shot his wad while I fucked him, it would be into his own mouth.

It didn't take long to have Mark onto a chair and positioned as he was Saturday night. This time, I dispensed with the boxer briefs. Mark's pretty ass was etched into my memory. And this time, rather than viewing Mark through the internet, I was standing beside the chair he was lying back on with my hard cock resting on the warm, moist crease between his lips, with my left hand spread over the top of his head, my right hand holding his balls.

"You are such a horny boy, Mark," I chuckled as I tightened my grip on Mark's balls. "Your big cock is always so hard."

I made my long, thick cock snap up and down, cock slapping Mark's lips.

"Lift your knees back more and put them out on either side of your pecs," I ordered as I twisted his right tit.

"Such an obedient boy you are, Mark. See how your big leaking dick is hanging down right over your face now?" Smiling as I watch the first long strand of his pre begin to stretch down from the tip of his cock to Mark's lips. "Open your mouth."

"Good boy, now milk that big dick onto your tongue."

"Let that jizz pool on your licker, Marky. I need some lube. Not much. Your butthole's pretty loose, "I teased.

Dipping the big head of my cock into the growing puddle of precum on Mark's outstretched tongue, coating it lightly before I bend forward and kiss his lips.

Moving to Mark's right ear and whispering, "Buddy, shoot whenever you're ready and gulp it all down," before I move to the front of the chair, press the head of my cock to his asshole and grip him by his ankles.

I knew the pegging had prepared Mark for the fucking he was about to get and that no slow and patient workup was needed. Holding Mark by his ankles and bending his knees back, I thrust my cock to the hilt and punched his prostate. Mark's mouth flew wide open, as did his eyes, which bored into mine, but he uttered no sound. As his fist pumped faster, my pelvis lifted, then jackhammered down and punched his clock again. Then Mark's fucking began. I was on top of him on my toes with only my hands clutching his head supporting me as my piledriving steel-hard cock reamed his upturned ass like a hydraulic piston.