Fraternity Caper (MM, bd, sm, anal, whipping, cbt, initiation) Chapter 2
NOTE: Be sure to read Chapter 1 before beginning this one. Chapter 2 includes a shift in the coercive tone of the story. For Bobby, Ronnie, Kyle and Phil there were some `hints' about a desire for more than a job. That confirmation of consent will be made soon. The same will be true as the pledges come to center stage.
Wednesday- Bobby's Training
It was 6:00 pm, on the dot when Bobby arrived at my office. He was now dressed more casually, wearing a green short sleeved button down shirt, khaki cargo shorts, white socks and black athletic shoes. He was even more wonderful than I remembered. Unlike his ill fitting bargain suit this outfit fit him to perfection. His classic teen build was accentuated by the outfit. Little or no fat, a flat chest and trim abs and thighs and a slight waist you just wanted to wrap your arm around. All of which was topped off with a sweet boyish, dimpled face and that mop of reddish blond hair parted in the middle and swept back above his ears.
I invited him into my office and we both took a seat in front of my desk. If Bobby was nervous, he clearly did not show it. The tent projecting beneath his cargoes, confirmed his excitement. This was one amazing young man.
I smiled at Bobby. "Well Bobby, I am very glad you made it. I think you will work out fine."
Bobby's face glowed. "Oh sir I am sure I can do a good job. I really am a fast learner and will complete all the training you can give me."
"Bobby, I don't have any doubt about either, and I have a surprise for you."
His reaction was like a little kid's, he beamed at my acceptance of his commitment and was excited about a surprise.
"Well Bobby it's like this. I have no doubt that you will be able to learn all the waitering skills that you need, so much so that I will tell you up front, you have the job at Tammerlane's and can start as soon as you are ready!"
The look on his face was priceless, one of great relief and extreme happiness. His response was like a squeal of delight and he his eyes filled with water as he stammered, "Oh, sir, oh, sir, Thank you. I promise I will be the best waiter ever!"
"I am sure you will Bobby," I exclaimed while rising to my feet and extending my hand. Bobby jumped to his feet and eagerly shook my hand.
"Thank you again, sir!"
We ended the hand shake, then just stood there looking at each other. Bobby's mind was obviously racing and full of joy. I shifted my position slightly suggesting that it was time for him to go. Bobby noticed this, thought for a moment, frowned slightly and then asked, "Uh sir, does this mean I don't have to do the training tonight and tomorrow?"
What registered in Bobby's voice and stance was clearly NOT relief. It signaled disappointment!
I walked over, stood beside him and wrapped my arm around his shoulder.
"That's right Bobby, you passed the test! You don't have to do the training, you still have the job."
Bobby thought for just a moment. His cheeks reddened as he turned to look me in the eye and stammered, "But.. Uhh.. What if I really WANT the training... Can, uh, I still do it."
I smiled back at him, "Well Bobby, we'll see. If you can be absolutely honest with me and can correctly guess the nature of the training, I will take you through it."
Bobby perked up right away, thought for another moment and then said, "Well sir, I was pretty sure that there would not be much waiter stuff, I mean `that' you could learn pretty quickly." He glanced down and swallowed hard.
"Ok, good, go on Bobby," I said matter-of-factly.
His face got even redder and he shuffled his feet, while swallowing hard, "Uh sir, I figured there would be mostly other stuff, uh, you know, stuff that you just don't talk about."
I smiled reassuringly, patted him on the shoulder and said, reassuringly, "Come on Bobby, you can tell me, believe me I understand."
Bobby thought for a moment, took a deep breath and whispered, "You know, like sexual stuff, sort of hard too, maybe very hard. "
Bobby's demeanor conveyed both, relief that he had finally said it and a hint of fear that he would be embarrassed if he was wrong and that I might think he was really weird.
I laughed softly as I patted him on the shoulders. "Bobby, that took a lot of courage to say. Can I assume that you came here with that expectation in your mind?"
Bobby looked down and declared, "Yes sir."
"And even though you already have the job, you still want to do it?"
Bobby now looked me in the eye and whispered pleadingly, "Yes sir, please I think I really need it, I mean if that's what it is. I mean I've never done anything like I think I would have to do. And I have been having strange dreams for a long time now, dreams that I'm scared to tell anyone about." His words flowed out like a tidal wave. "... uh but if I was wrong, well please forgive me for thinking the wrong things."
I stepped in front of Bobby, grabbed both of his shoulders and looked him straight in the eye, "Okay Bobby, you were absolutely right! I would be pleased to take you through the training, but will tell you upfront that it will not be easy."
Bobby beamed with hope and joy, "Oh my gosh, that is great sir! I want to do it! I will do anything you say!"
I smiled broadly, "Ok Bobby, I'm convinced, I will take you through the training!"
I thought Bobby would cum then and there. What had been a pole for a pup tent, was now one for a big top. The front of his cargoes was stretched to the limit.
"Thank you sir, thank you."
"Okay Bobby, before we begin I am going to give you some instructions. Listen carefully to what I say and ask me if you don't understand."
Bobby stood now like he was at attention, listening intently. "Sir, yes sir!"
Nice touch I thought. Probably something he saw in a movie, or maybe. "Bobby, have you had any military experience?"
"Sir, yes, sir! I went through a special Army training program last summer to prepare to apply for an ROTC program next year."
I nodded, "Very good Bobby." This was going to be a fun 24 hours and perhaps something ongoing if Bobby's need was as strong as expected.
"Now Bobby listen up. During this training program, you will be treated like a slave and I will be treated as your master!"
"Sir, yes, sir!"
"You will follow all orders without question and without reservation."
"Sir, yes, sir!
I was now quite excited myself. "Once we begin, you will no longer be allowed to question anything, with the only exception being that if you do not understand an order."
He shouted his agreement again.
"Now Slave Boy, your Master needs to know something about your limits. I have no doubt you have read some stories about the types of things that can happen to you. Though you have not explored them like this, you have some limits. Tell me what you think they are."
He thought for a moment, "Master sir, I can't eat shit or drink piss and nothing that will leave permanent marks on me sir. Other than that you do whatever you wish!"
I laughed and announced formally, "Very well Slave, your limits are accepted and will be respected."
"I am now going to give you two words that are important. They are called safe words. The first is "slow", you will use that at anytime you really need me to slow down. The other is "stop", use that if you need to end our training session completely. I will not think less of you in any case and as I said will absolutely NOT jeopardize your job. Understood?"
"Sir, yes, sir! I won't need them though sir!"
"Hahaha, my you are pretty cocky for a new slave boy! Well we will see."
The look on his face was just priceless and clearly showed the depth of his need and determination.
"I will now give you your "standing orders". Any breach of your orders will result in a punishment."
"During your training, you will NOT touch your manhood in any way without my instruction.
You will also NOT cum without my permission.
You may ONLY ask a question if you are confused about an order, otherwise, you will only speak when I give you permission!
You are free to scream all you want and as needed. If I grow tired of the screams I will gag you. If I do, ONE sustained GRUNT will be your safe word for slow, TWO Clear sustained grunts will be for stop.
You will not piss or shit without my permission.
If you are in a room, and not restrained, and I enter the room, you will immediately drop to your knees and press you forehead to the floor in front of my feet. Then you will raise your head and chest back up, spread your legs wide and then lower your back to the floor behind your with your arms on the floor at your sides, and your lower legs bent underneath you. And, if I enter with anyone else, you will first touch your forehead to the floor in front of them, before assuming your back position. The tent pole in his cargoes quivered at this remark.
"If I say "present" at any time, you will immediately assume that back position."
"Very well Bobby, do you understand your Standing Orders?"
He said nothing. I waited expectantly.
"Well?" I yelled.
He continued to stand there.
Wow! This kid was really good! I laughed and then said, "You have permission to answer."
Bobby could not hide his feeling of pride as he shouted, "Sir,yes, sir."
"Okay Bobby, this is what I want you to do. You will go through the door at the back of my office and down the hall. When you reach the end you will open the door and go into the garage. One of my assistants will be waiting for you there. You will do exactly as he tells you."
Bobby's look indicated he understood.
"Okay, Bobby, now go."
Bobby turned and headed out the door.
As I watched him leave, I could see it was a little difficult for him to walk with his tent pole pressing so hard against his cargoes.
Since so many guys from the college had completed the training (and many wanting more), it was very easy to find an assistant when needed. The one waiting in the garage was Brett. He was one of the star soccer players. Plus he was an absolute fiend when it came to working out. Every part of his body was well defined and hard.
The garage was lit by several candles. Brett, still wearing his soccer uniform from practice, stood behind the only vehicle in the garage, a large black van, with heavily tinted windows and solid sides with no windows except the front driver and passenger's.
As soon as Bobby entered the garage, I rushed down the hall, turned the corner and silently drew open a curtain that covered the garage window.
I watched as Bobby approached Brett. As soon as he was in front of Brett, he snapped to attention. Brett was very experienced at this, he stood in the same position as always, so that I had a clear profile view of both.
After looking Bobby up and down, he ordered, "Spread your legs wide and place your hands behind your head and don't you dare move until I tell you to!"
Bobby obeyed immediately. His stance now made his erection even more obvious.
Next Brett took off his own shirt, revealing his beautiful chest and abs. His shirt was still wet with sweat from soccer practice and his chest, stomach and back glistened in the candle light.
Brett always followed his orders well. He knew that he could add something to the routine for his own amusement as long as he prepared the slave as required. Brett was also most creative. He used his shirt to wipe more of the sweat from his body. Then walked over and draped the shirt over Bobby's face, no doubt with the sweatiest part over Bobby's nose.
Brett next walked around behind Bobby and began to feel every inch of Bobby's body. He took his time, pinching, probing and massaging. After twenty minutes, he slowly worked his way around Bobby's waist, patted his groin and slowly opened the top of Bobby's cargo shorts. I could see Bobby shake with excitement all the way across the garage.
After resting his hand above Bobby's groin for several minutes, he gently took hold of the zipper, and pulled it all the way down. We were both in for a surprise.
Bobby was not wearing any underwear and his painfully erect and gorgeous circumcised manhood sprang through his parted zipper and assumed a glorious 45 degree upward angle. Brett moved quickly around to the front, grabbed Bobby's balls with one hand and wiped his finger over Bobby's piss slit. He then pulled his shirt away from Bobby's face and held his finger in front of Bobby's mouth. It glistened with a hefty amount of precum.
"What is this slave boy?" he demanded.
Bobby stood silently while looking at Brett's finger.
Brett squeezed Bobby's balls harder. Bobby winced with pain, but did not speak or move.
"Okay, slave boy, good for you, now lick your pre-cum off my finger."
Bobby did as he was told.
Brett continued, "Okay smart boy, you can put your feet together and lower your hands." Bobby complied.
Brett retrieved a canvas travel bag from beside the van and placed it on the floor in front of Bobby.
"Now strip completely and put your clothes in the bag."
Bobby wasted no time removing his clothes and placing them in the bag. He stood back up. Then Brett ordered him to spread his legs again and place his hands behind his head. Bobby spread em wide and placed his hands behind his head.
He made an awesome sight, with his slender well formed body and beautiful erection glistening in that candle light. And of course that gorgeous mop of reddish blond hair almost glowing.
Brett continued his assigned task. He placed leather restraints on Bobby's wrists and ankles. Then wrapped a piece of rope around Bobby's little waist and secured it tightly.
A leather collar with four metal rings was next put around Bobby's neck.
Then he tied a piece of rope snugly around Bobby's ball sac. Finally he tied a longer piece of rope around Bobby's manhood, just below the swollen cockhead. He pulled the rope between Bobby's legs, through his crack up his back and through the back ring of the collar. He tied the rope off with a taut line hitch (ahh the value of Boy Scout training). This type of knot was used on tent ropes and could be easily tightened to keep the rope as tight as needed.
Brett then stood behind Bobby and began tightening the hitch. As he did, Bobby's rock hard manhood was slowly pulled from and an upward 45 degree angle to a downward 45 degrees. He grimaced from the pain and moaned slightly.
At last, Brett moved around in front of Bobby. He smiled at him and then slowly and seductively slid his own soccer shorts to the floor and stepped out of them.
My cock rapidly completed its own rise to full erection. What an incredible sight, Bobby with his hot teen body and boyish face, standing naked with hands behind his head, legs spread and his manhood in an interesting bondage. And then Brett, naked now except for his soccer shoes and sox and a jock strap standing in front of Bobby, leering at him.
When Brett reached for his jock strap and slowly began pulling down his beautifully muscular legs, I was certain Bobby was about to cum. He was breathing hard and his pelvis began a slight humping motion.
Brett was erect as well. He stepped out his sweaty jock and stepped closer to Bobby. After waving his jock under Bobby's nose, he quickly bundled it up and rather roughly forced it into Bobby's mouth.
"Suck on that dude, until your Master says you can remove it."
Bobby began sucking Brett's jock, it was very sweaty and saturated with Brett's athletic sweat and juices. It was somewhat revolting to Bobby, but at the same time he realized he was turned on by it.
Brett slipped his shorts back on and then headed out of the garage.
He found me in the hallway and I thanked him for his excellent prep work. He of course thanked me for another opportunity and added, "Sir, if you have some time for me, I think I need another training session of my own, to help me expand my limits a little."
I smiled and told Brett that I would be happy to and would see when I could work him into my schedule. He thanked me again before we both headed back into the garage. As soon as Bobby saw us, he immediately ran over and knelt in front of me then bowed down and placed his forehead on the floor. He then did the same thing in front of Brett, then he assumed his "present" position. It was a little tougher than normal due to his current cock bondage. However, he discovered that once his back touched the floor, the slight arch in his lower back actually helped ease the pressure on his cock.
I gestured to Brett, who immediately knelt beside Bobby. He reached under him and carefully tightened the taut line hitch so that Bobby's cock was once again straining against the pressure. Bobby moaned again and I could see sweat beginning to form all over his body.
I looked down at Bobby's sweet body, it was intoxicating. I then knelt beside Bobby and spoke to him softly, "Well Bobby, since Brett did such a nice job on preparing you, I think you owe him a service." The look in Bobby's eyes indicated he understood. I removed Brett's jock from Bobby's mouth and laid it on his chest.
I had Brett bring a chair over and place it beside Bobby, just close enough to his head. Bobby continued to sweat in his "present" position. Then I said, "Okay, slave boy, Brett had to rush over right after soccer practice so he didn't have a chance to shower, so you are gonna help him out a little."
I had Brett sit in the chair and extend a foot to Bobby's face.
"Now Brett, you may help Bobby a little here and there by repositioning your feet. Bobby, you will stay in your present position, remove Brett's shoes and socks and then clean his feet with your mouth and tongue."
There was a hint of surprise in Bobby's face, but to his credit, he started right in. It took him quite some time to undo the shoe laces. But he figured out a way to use his teeth to loosen the laces. Then he took a firm bite on the back of each shoe in succession and inched them off. After that the socks came off rather quickly. At this point Bobby had the most charming look of disgust and determination. Brett may have had a gorgeous perfect body, but his feet were anything put perfect in the odor department.
Still he forced himself to wash Brett's feet. He licked them up and down all over and even went as far to suck on each of Brett's toes, which resulted in some moans of pleasure from Brett and a rapid tenting in his soccer shorts.
When Bobby had finished, he licked his lips and looked at me as if to say what next? I noticed he remained absolutely rock hard.
"Okay Brett, stand up and remove those shorts. Then straddle Bobby's face."
Brett dropped his shorts, stepped out of them and straddled Bobby's face. His cock pointed towards the top of Bobby's head and he was growing harder.
"Now my little slave boy, your mouth is now an "auto-crotch washer". Give Brett's cock and balls and pubes a good washing."
Again Bobby complied, and what a job he did! His mouth and tongue sucked and washed every inch of Brett's 9 incher and his balls and I swear his tongue washed every hair in Brett's crotch.
With his nose and tongue buried deep in Brett's pubes, I glanced again at Bobby's own manhood... his pelvis was pumping... his cockhead looked like it was about to burst and pre-cum was dripping on the floor. Bobby looked like he was ready to explode. Sweat poured from his body.
I nodded at Brett and he leaned back just enough to get his genitals out of Bobby's tongue range.
I looked at Bobby seriously, and used his name. "Bobby, you know that if you CUM without my permission you will receive a serious punishment?" He was breathing fast and hard. His eyes begging to be able to cum, BUT also confirming his orders.
"I already can tell that you are tough and man enough to accept punishment, but I DO NOT want you to CUM at this time. Use your inner strength and stop the process!"
Bobby gave me one last look of desperation, then began to slow his breathing and forced his pelvis to stop the undulation. He brought himself under control, but his manhood remained hard.
Brett then helped me get Bobby into the back of the van. It was empty and had no seats. A sheet of heavy plywood covered the floor. Large metal eyebolts were scattered around the board, and were firmly secured to the truck's floor. There were also a number of eyebolts on the walls and ceiling.
We placed Bobby on his back on the floor, spread-eagled him and secured his wrists and ankles to the floor. Bobby was also blindfolded. As a final touch I secured a small cylindrical, battery powered vibrator to the underside of Bobby's bound cock and secured it with duct tape. I turned it on low then leaned down and kissed him gently on his forehead while stroking his beautiful hair.
I climbed out of the van and closed the doors. Brett was still completely naked and sporting a major hardon. I picked up Brett's soccer uniform, jock and socks and shoes and threw them in the van.
I smiled at him and said, "You know you did such a good job that I think you deserve a challenge reward." Brett smiled broadly as his cock twitched.
"You can jog home as you are."
Luckily for Brett it had gotten dark and although his house was on the other side of town, my office was on the outer edge and he could jog around the outskirts through farm fields, a long run to be sure, but safe.
Brett thanked me then took off running. I knew this was somethimg he really enjoyed.
And with that I snuffed out the candles and drove off with my exceptional new slave boy.
The drive out to the manor was enjoyable. I could hear Bobby working hard to control his excitement. He did a lot of deep slow breathing to help control his need to cum. Glancing back I was sure he was going to lose the battle several times... the stimulation of the vibrator taped to his manhood was becoming irresistible. Yet although he flirted with the edge he was able to keep himself from cuming all the way to the manor.
As soon as we arrived, I released him from the van and guided him into the basement. I placed him in the center of the room with his back to the cells, facing the platform. His eyes remained covered as I lit candles throughout the room.
Then I walked behind him and slowly massaged his shoulders, arms, back and thighs. I also loosened the taut line hitch enough to allow his straining cock to return to its normal upright position, and switched off the vibrator attached to his cock.
I retrieved a metal D ring clamp, pulled his arms behind his back and clamped his wrist restraints together. Finally, I untied the rope on his collar, pulled it down between his legs, and untied his bound cock and balls. I left the vibrator taped to the underside of his cock. Then I removed the blindfold. His eyes adjusted quickly to the light and he began glancing around the room. As he saw the various whips and other implements of torture and restraint he quivered slightly but quickly returned to his confident stance.
I took hold of the back of his neck and guided him over to the first of several large chests. I then pushed him down on his knees and opened the chest. It contained a collection of butt plugs. I gestured towards the plugs and said, "Choose!"
Bobby took his time looking them all over. At last he leaned over a picked up a medium sized plug with his mouth. It looked like a tear shape pineapple and was covered with tiny dull rubber spikes. An electrical cord and a controller dangled from the plug. I patted him on the head, took the plug and set it on a nearby table.
Still on his knees, I guided him to the next chest and flipped it open. It had a nice assortment of tip clamps with chains. Again I motioned to the chest and said "Choose!" He looked over the selection and retrieved a set of screw down clamps connected by a silver chain. I placed it on the table and we proceed to the next chest. This one held several ball stretchers and separators.
After a brief deliberation, he selected a combination leather ball separator/stretched.
He then looked towards the next chest in line. I patted him softly on the head and said, "Not yet Bobby, you're not ready for those yet."
He looked disappointed. I pulled him to his feet and guided him across the room. I had him face the cells that lined the wall, pointed and said, "Choose!" He looked up and down the rows of cells, then focused on one of the middle cells.
I gestured toward it and said "Go."
Bobby walked to the cell and went inside. I walked over to him and explained, "This is your training cell. In the back left corner you will see a bucket, use that to relieve yourself but don't get any piss or crap on the floor. In the other corner is a bowl of water. If is fresh and you may drink it. Now sit down and wait. I will be back shortly."
Bobby, hands still shackled behind him, carefully lowered himself to the floor and sat down. I closed the cell door and locked it. I then went upstairs.
After some thirty minutes had passed I returned with a bundle of things.
Bobby perked up when he saw me approach. His manhood was softer now but not completely. I opened the cell door and walked in. He immediately knelt down in front of me, and placed his forehead on the ground. Then he rose up on his knees, spread his legs and assumed the "present" position.
"Bobby, your performance has been exceptional, especially for a brand new slave. So much so that you deserve some rewards. You may leave that position and sit on the floor in front of me. He painfully stood up and then sat down. I laid two blankets on the floor along with a pillow. Then I placed a plate on the floor in front of him along with a glass of soda with a straw. On the plate were two nice slabs of pizza.
I sat down next to him, wrapped my arm around his shoulder and proceeded to feed him the pizza and soda. When he was finished, he looked at me with glassy eyes then leaned over and pressed his face against the side of my chest in a thankful snuggle. I left him nuzzle for awhile, then declared, "Okay it is time to get you ready for bed. Go and retrieve the items you chose from the table."
Bobby rushed out of the cell. He picked up the butt plug with his mouth, then turned around and grabbed the tit clamps and ball stretcher with his bound hands.
When he returned I had him stand with his legs spread wide. Without delay, I put on the combo ball stretcher. I pulled his ball sac down and snapped the leather stretcher around the top of the sac. His balls were forced to the very bottom of the sac, and could not contract towards his penis. I completed the task by snapping the separator strap on. His trapped balls were now separated from each other as well.
Next I applied the tit clamps, just tight enough to ensure they would stay on through the night. He winced when I screwed them into place on his hard erect nipples.
I took the butt plug and then lubed my fingers and the plug. I directed Bobby to kneel and then helped him lower his chest to the floor. I forced his legs apart and slowly began probing his tight little hole with my finger. It didn't take Bobby long to relax his muscles. I helped that along with some coaching. Finally he was loose enough to begin the plug insertion. Though it was covered with those tiny rubber spines, I knew they would tickle more than the hurt. I greased the plug well and then started working into Bobby. His hole widened slowly. As the widest portion of the plug began its journey, Bobby began to moan loudly and his sweat glands went into high gear. I slapped him on the ass with my hand and pressed on the plug.
Bobby's breathing was now very hard and his moans were becoming high pitched. I reached between his legs, grabbed the vibrator on his cock and switched it to medium. Bobby began to buck.
I slapped him on the ass hard and exclaimed, "Ok slave boy, it's up to you to get the plug all the way in. I'm gonna continue slapping this beautiful little ass of yours until you get it in."
I held the plug firmly and slapped his ass much harder this time. Bobby leaned back and pressed against the plug... he moaned louder... I slapped him again... he grunted and forced his butt against the plug...
The next ten minutes were hot ones. I continued to slap Bobby's ass, he tried harder and harder. His breathing was now coming in a series of short pants, then he would grit his teeth and force back on the plug. As it slowly inched in, he would scream a little more.
Finally, covered with sweat and breathing savagely, Bobby made a huge lunge backwork with such force that the plug plunged into him and snapped into place. Bobby screamed loudly, then settled in to a rhythm of gentle sobs as I massaged his red butt.
I let him relax for a few minutes.
At last I laid him down on his side on one of the blankets, placed the pillow under his head and covered him with the second blanket. I unraveled the cords from the butt plug and plugged it's controller into he wall and adjusted the timer. With this setting, every 30 minutes during the night, the plug would switch on and warm up. Once it was warm, it would begin to throb and with the plug locked into this position, it rested snugly against his prostrate. The throbbing would last for ten minutes then stop. I thought for another moment and made one final adjustment. With this setting, every time the plug activated, the throbbing will be at a different intensity.
Then I grabbed his cock vibrator and switched it to low.
I paused to admire his rock hard member. Then leaned down and gently kissed his cockhead. Bobby shook all over and looked at me pleading. I shook my head and left the cell, locking the door behind me. I blew out all the candles and went upstairs to be. There were microphones embedded in the walls that would enable me to hear any sound in Bobby's cell during the night.
When I got to my room, I switched on the cell monitor, stripped naked and laid down on the floor between two blankets.
I began stroking myself as I prepared to sleep. Just as I was drifting off, I heard a soft buzzing sound and a series of moans from the cell monitor, the butt plug had kicked in. Just thinking about it was enough to make me shoot my load. I fell into a deep sleep thinking about Bobby and the experience he would have during the night.
Periodically throughout night I awoke from my sleep as moans and sounds of rapid, controlled breathing echoed from the monitor. As it got closer to morning, the moans became increasing desperate, the breathing more rapid and new sounds entered the mix, stifled grunts and small screams.
I awoke just after dawn, took a nice hot shower and then put on my long black hooded robe. I went to the kitchen to grab a cup of coffee and a bagel. I took them back to my room and sat down, sipped at my coffee and listened to the monitor.
The moaning was continuing. Suddenly there was a buzzing a strong buzzing sound...the butt plug's random controller must have just chosen it's highest setting. I could hear the absolute desperation in Bobby's moans. His breathing grew very rapid and deep. Then it happened, a high pitched scream, "ARRRRRGH"... a fierce and extended cry of "NOOOOOOOOOOO!", and then the familiar sound of orgasm. Judging by Bobby's moaning and squeals it lasted almost 5 minutes. When it was over, there was a long period of heavy breathing, followed by a new sound... crying.
I immediately left the room and headed for the basement. I lit the room with many candles and walked over to Bobby's cell. It was an amazing sight.
Bobby had kicked off the blanket and was laying on his back, shackled arms under him. His beautiful chest heaved with deep breaths and he was crying. Sweat covered every inch of his body, and of course there was cum everywhere... on Bobby's face, chest and stomach... on the floors... on the walls... and perhaps even a little on the ceiling.
I opened the cell and walked in, Bobby looked at me and immediately went through his bowing routine and assumed his "present" position. It was a struggle for him to do it. He tried to stop crying, and was only marginally successful.
I felt a lump in my throat. "You may stand Bobby." Bobby slowly rose to his feet, looked down at the floor and continued sobbing.
"Bobby, you have my permission to speak."
He muttered through his sobs, "Master sir, I am so... so sorry... I mean I tried real hard.. and I almost made it, but I just couldn't hold back any more. Please, please don't make me leave, punish me however you want, but let me continue the training." He looked at me with his a big set of sad puppy dog eyes.
"Well Bobby, you will have to be punished of course... but because you did such a great job holding out as long as you did, it won't be as hard as it might be... and of course you can continue the training!" I smiled at him, stepped closer and gave him a good hug.
Bobby sobbed in my arms, but these were sobs of joy. "Oh thank you Master, you won't be sorry."
We stood that way for awhile then at last, I stepped back. "Okay slave boy, you are back in silent mode again. I have some chores for you right now and then we will move on."
I carefully removed the butt plug, tit clamps, ball stretcher and the vibrator on his cock. He grunted a few times but did not moan. Not even as I removed the duct tape that had held the vibrator under his cock all night.
I retrieved a bucket from the corner of the room, filled it with hot water and some cleaning liquid and returned to Bobby with a pile of rags.
"My little slave boy will now clean his cell. Before using the rags, you will lick up your cum where ever you find it. Then use the rags to wipe everything down. Fold the blankets and stack them near the cell door. Do a good job! Oh yes, and since I will be in and out you do not need to do the bowing and "present" until I tell you to resume."
I turned and headed for the upstairs as Bobby literally bounced around his cell, licking everywhere.
I made a few phone calls, did some things in the kitchen and then returned to the basement. I had been gone thirty minutes. Bobby had done a great job cleaning. I couldn't find a drop of his manhood nectar. The blankets were folded and stacked as ordered. I also noted that Bobby had used the relief bucket in his cell to piss and crap and that he had lapped up just about all the water in his bowl.
I patted him on the shoulder. "Good boy, now follow me."
I led Bobby upstairs and into the bathroom. I pointed at the shower and said simply "Clean yourself."
He smiled broadly and immediately jumped into the shower. I left him alone for a good fifteen minutes as I prepared breakfast. When I returned, he was standing in the middle of the bathroom waiting for me. What a sight he was indeed! He had washed and dried his hair and scrubbed his body which emitted a glow of boyish sexuality and exuberance.
He followed me back to the kitchen and looked very surprised when I pointed at one of the chairs and said, "Eat!"
He sat down and quickly devoured the plate of scrambled eggs, bacon and toast and drank the whole pitcher of fresh orange juice.
Following my gestures he came over to me. I pointed to several covered dishes on the counter and to one in the oven. There was also a basket of toast, a pitcher of orange juice and a carafe of hot coffee. Then I led him into the formal dining room.
I took a seat at the table, placed a napkin in my lap, and then looked at Bobby, "My breakfast order is already prepared in the kitchen, you will now wait on me. You may speak. Think about what you have seen done in restaurants and go from there. If you do something wrong, you will know, just keep trying until you get it right. Now leave the room and return and start your waitering."
Bobby left the room and returned carrying the carafe of coffee. "Good morning sir, would you care for a cup of coffee?" he said confidently. I said yes, and he began to pour me a cup. I reached over and slapped him hard on the ass. He stopped, thought for a moment, then walked around to my other side and started pouring again. When I didn't slap him, he smiled. As soon as my cup was full I thanked him then looked all over the table. He was concerned. I slapped him hard on the other cheek. Then helped him a little by picking up a teaspoon and looking at my cup. Bobby understood immediately. He apologized graciously, turned and left the room, and returned quickly with cream and sugar.
And so it went, Bobby did a nice job, he was a fast learner, but his ass was still bright red by the time I was finished.
When we returned to the basement, I led Bobby to his cell. I had removed the blankets, but the pillow was still there. I had also refilled his water bowl and cleaned his relief bucket. I left Bobby standing in the middle of his cell, went over to one of the trunks and retrieved a large dildo. I greased it well then returned to Bobby. His eyes widened when he saw the size of the dildo.
I had him lie down on his back and lift his knees towards his chest. I handed him the dildo, pointed toward his red ass and said, "Use!"
He set to work immediately, it was tough for him, even after the night with the plug he was still very tight.
I looked down at him and laughed, "You will ravage yourself for the next hour, then you will take a nap with your little friend inside you. When I wake you, we will deal with your punishment for cumming. Also when I return, you will continue with your normal bow and "present" routine."
I left his cell, locked the door and headed upstairs. Since I was a particularly horny master, I went to my little office, sat down and watched the TV screen of the video that was being recorded of the action in Bobby's cell. He was a delight to watch.
I was amazed that Bobby came so close to judging the end of the hour, and kept watching as my wonderful slave boy drifted off to sleep with "his little friend" embedded deep inside him.
I decided to let him sleep for a few hours. He could use the rest, I needed to take care of some business and I wanted my slave boy to be rested.
Just after 2:00 p.m., I returned to Bobby's cell. As soon as I entered the cell he did his bow and then leaned all the way into his "present" position.
It was exciting to watch. With the dildo stuck deep inside it was a little more difficult and he moaned as his back touched the floor.
I left him in that position as I retrieved a few more items. When I returned, I had a leather glove on one hand. The palm was lined with soft rabbit's fur. I knelt beside Bobby and wrapped my gloved hand around his manhood. Then I reached under his butt and grabbed the end of the dildo.
"Okay, slave boy, show me some of that great pelvic action of yours. Fuck my hand." Bobby got the picture and immediately started pumping his hard cock into my gloved hand. I held the end of the dildo firmly, forcing his to fuck himself at the same time.
"When you get to the edge, stop your humping boy!" I explained.
Bobby continued this display for a good 15 minutes. Though his muscles were strained with he legs bent back under him, he maintained a good pace. His body was once again glistening with that sweet sexual sweat. At last he stopped, panting hard, his dick quivering in my hand oozing a lot of precum.
I let him catch his breath, released his cock, and had him stand. "Now slave boy, it is time for you to pay for breaking the no cum order.
I led him over to my spanking bench, which was similar to a sawhorse with padding. The position it was in added another dimension. Once a boy was secured to the bench, his face hung just above the gently rushing cool water that ran through the water trough.
I bent Bobby over the bench and secured his wrists and ankles to the metal shackles in the floor. His ass was spread wide and pointing in the air. I also had free access to his cock and balls.
I retrieved a fraternity paddle from the wall and showed it to Bobby.
"You now have permission to speak and here's the deal. Since although you may not have experienced this before, you obviously have been busy reading about it, so you can guess that you will be required to count each stroke out loud.
"Yes sir!" he announced proudly.
"And, in addition, if you lose count, you will start counting all over again at one, and I will add ten strokes to the total."
"Yes sir! He proclaimed, as his cock jerked in anticipation.
"Now, how many swats do you think you deserve boy?"
"Twenty hard ones sir!"
"Very well, boy, since you held out for so long, I will let that stand. And one more thing boy."
I knelt down and slid my "Water-Bater" over his hard cock and secured it to him, by snapping a Velcro strap snuggly around his balls. The Water-Bater, was essentially a plastic cylinder with water encased in its soft walls. When plugged in, a tiny heating element warmed the water while an elastic ring moved slowly up and down the shaft.
"You are now allowed to cum, as often as you can! Everytime you do you thank me."
I turned the Water-Bater on and waited for it to begin its stroking. Then I laid a hard swat on Bobby's beautiful pink butt. He bucked and grunted.
"One sir!"
I struck again, a little harder this time.
"Two sir!"
His ass reddened and I laid in with gusto.
"Three sir!"
We got all the way to ten. His body was now covered with sweat, ass as red as a tomato and he moaned loudly after each swat.
As soon as I laid in with the 11th swat, he screamed as his body went into a wild spasm. He bucked up and down in his restraints, shouting, "Oh god, thank you sir... thank you sir!" over and over again.
I looked under him and saw spurt after spurt of hot white jism slamming into his chest, chin and face. When at last it subsided I inquired, "How many swats was that boy?"
"Ten sir" he shouted.
"Wrong boy, it was eleven. So we start all over again, but now you have you will receive 30 swats."
I allowed him to think about it some more as I filled a bowl with some icy water from the trough. I dipped my hands into it patted Bobby's ass with it. I could tell it felt good to Bobby, so I kept at it until the bowl was empty.
Then we started again!
"SMACK"
"One sir!"
By the time we hit 21, Bobby was once more in full moaning and thrashing mode. His cock was once more hard and was again dripping precum.
At 22, Bobby went into his gyrations again and screamed as more cum shot from his dick. "AHHHHHHHHH... OHHHHHHH... thank you sir, thank you."
The amount of man spunk he had left was amazing, less than before, but still a lot.
I continued swatting his tender butt, his cock showing no sign of softening. We reached 28, and after I delivered the 29th, Bobby shouted, "Twenty-eight, sir."
I felt sorry for him. "Uh, boy, do you realize what you just did?"
He thought just a moment and then said, just a little too sheepishly, "Uh, I screwed up again, didn't I sir."
"Yes you did, and we have to start all over again, and now you get 40!"
"Yes sir, I understand sir."
"I am going use some other things on you boy. I'm tired of working that red ass. So I'll work on your back... thighs and balls." I got a small riding crop and a light whip from the rack. As I returned to Bobby, I glanced between his legs and I caught a smile on Bobby's face. `What a clever boy, and a hungry one at that' I thought. That last slip up was no accident. Well, well, I'll play along.
The cycle began again. This time I worked his back with the small whip, and inner thighs and a couple of times his balls (lightly) with the little riding crop. We proceeded slowly and this time he didn't miss a count. However, by the time we reached 40, Bobby had thanked me THREE more times. The last two being dry, but just as explosive.
I quickly removed the Water-Bater from Bobby's cock and released him from the bench. He fell to the floor sobbing. I knelt down and picked him up gently, allowing my robe to fall open, revealing my own naked body. I sat down on the edge of the trough with Bobby on my lap. I stroked his sweaty hair and patted him on his shoulder as I gently gently kissed him on the cheek. "That's ok, Bobby, you did just fine!"
He looked up into my eyes and said, "Did I really sir? I mean did I do well?
Are you pleased with me?"
I gave him a big hug and said, "You most certainly did!"
I picked up a ladle and dipped it in the stone trough. I let Bobby drink his fill. Then I carried him upstairs and laid down on the sofa. Bobby pressed his body against my skin as I cuddled him and stroked his hair.
We lay there for almost an hour. At last I lifted Bobby to his feet and said, "Just one last thing to do boy."
He followed me into my exercise room. I handed him Brett's soccer uniform, jock, socks and shoes and told him to put them on. They were a little big on him, but they wore the same shoes.
I gestured around the room. "This room is yours for the next hour. Use any of the exercise machines you want, but I want you to give yourself a really good workout. There is cold Gatorade and juice in the fridge over there, so drink what you need. I will be back in exactly one hour."
I left the room and could see that Bobby was taking it seriously. I returned to my room and dressed in my street clothes. Over the next hour, I peeked inside a few times and saw him using most of the equipment. By the time the hour was up, he had worked up a great sweat and was breathing hard.
"Well Bobby, you did really well, and I am almost sorry to say that your time is just about up."
Bobby was hunched over, breathing hard. He dropped to the floor in front of me, bowed down and then leaned back in present position. I had a hard time pulling my eyes off his body. His chest was heaving to catch his breath, and Brett's soccer uniform, now drenched in sweat, clung to his body.
At last I ordered him to his feet and lead him to the van.
This time he rode up front with me I noticed he looked sad. We drove for about 20 minutes until I spoke.
"Bobby, for your understanding, I will explain one part of this session that you wouldn't be aware of. When Brett prepared you in the garage, he was following a procedure I just started a little while ago. I use an assistant to do the preparation work. When we began, the assistant's job was to simply strip the new boy, put on wrist restraints, and then help me restrain him in the van. Some where down the line, an assistant added something as a surprise. Each time something new was added by whatever assistant was doing the prep. I keep some of them in as part of the routine the ones that amuse me the most. Brett's contribution was that rope deal. Anyway, I wanted you to understand what was up with that."
Bobby was listening, but lost in thought. We drove a little longer then I inquired, "Bobby, you may speak, and now you may ask two questions if you like."
"Well, sir, is that the end of my training?" he looked hopeful.
"Yes it is Bobby", I glanced at his face, it showed disappointment.
"That is of course unless you want to receive additional training!"
He perked up immediately and said, "Yes sir, I think I'm gonna need more! Will you continue training me?"
I smiled broadly and said, "No problem Bobby, I would like to train you some more."
He smile broadly and then looked over at me and prepared to ask another question....
"Careful Bobby", I warned. "You already asked your two questions, and since you will be receiving more training, if you ask a third, you will have to be punished for it next time."
Bobby sat there thinking for a moment, then looked at me with the most devilish, impish grin, "Uh, sir, how soon can we have the next training session?"
I looked him in the eyes. He raised his eyebrows and smiled.
We were both laughing as I backed the van into the garage, climbed out and closed the big garage door.
We walked around to the rear of the van, and lo and behold, there stood Brett wearing Bobby's clothes. They were snug on him and he had the shirt unbuttoned.
Brett said warmly, "Welcome back sir. I hope all went well."
I replied, "Yes it did boy. Bobby did extremely well."
I turned to Bobby, "Bobby, You will call me on Monday and we will schedule a time for you next session." Bobby beamed.
I have just one thing left for you to do before you leave.
Bobby snapped to attention.
"Good boy Bobby, now I want you to prepare Slave Boy Brett for a trip in the van. You will find all that you might need in that chest over there. That is of course all except your own imagination. Take as long as you need." I winked at Bobby.
Both boys stood there, surprise written all over their faces. After a moment, Bobby's impish smile returned. He looked at me and shouted, "Sir, yes sir!"
I headed towards the door. Behind me I could hear Bobby shouting, "Okay you miserable slave, get out of my clothes right now, and then get over, here!" ...
(To be continued)
NOTE: If you have any suggestions for any of the upcoming encounters send them to westwoodscotty@hotmail.com. If I can work them in I will.
Feel free to suggest some devilish challenges for the pledges OR any of the boys mentioned. LOL, like, "I would like to see Ronnie (or whoever) have to do this, or have this done to him, etc."