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Training the New Boy

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He emailed me on a site where boys look for daddies. I agreed to meet with him after checking out his pix and sending him some basic rules for training and play. He agreed to the basic rules which were once I enter his apartment, he is to strip naked and wear nothing until I give him permissions. Next, he is willing to learn. I will demonstrate what he will learn to do and then he is to learn it. Here is the list of tasks he will learn to master: suck cock, lick and suck balls, suck nips, lick pits, rim ass, take a cock up the ass, get fisted, shave whatever he is told and swallow my piss. All of these will be taught in small steps to get him used to the routine.

He was an eager boy of 23. He readily agreed and I decided to start the lessons right away. His first assignment was to meet me at his door, say nothing, and allow me to enter, then remove all his clothes and kneel. He followed my written instructions immediately and patted his head and kissed his forehead. I told him the lessons would get harder and there would be some rough stuff so he had one last chance to back out, all he had to do was get dressed and we were done training and would just fuck and I’d leave. He remained kneeling and did nothing.

I asked him to take off my shirt and lick and suck my nips, twice each. Then open my zipper and suck my cock for sixty seconds. These were tests to see how much he knew and what I needed to teach him. How did he use his tongue, teeth, lips, etc? Where did he place his hands if he used them? He licked my nips like a lollipop so he would need work there, but he sucked my cock like a Hoover vacuum so that needed little instruction.

I told he did well for the first demonstration of his skills but his tit sucking needed work. I led him by his rock hard dick to the floor of his living room, had him lie on his back and slowly went to work on his man teats to show him how it was done. I licked his right nip, then slowly formed my lips around his tit and sucked in forcing the nub end up into my mouth and using my tongue to rub along the end. Then I slowly and gently bit down until he was just at the point of pleasure and pain and held him there for a full sixty seconds before releasing my mouth and freeing his nipple. He moaned and his breathing became more like panting while I worked his nipple. When he had recovered a bit, I began the same process on his other nipple. He moaned like he was a teenager in heat. He reached for his swollen cock and began to stroke it but I slapped his hand away and told him he was not to touch himself nor could he shoot any cum unless I told him it was okay to do so. I continued to work his tits alternating one to the other for the next fifteen minutes. By now, his nips were swollen and red and stood at stiff attention, hard enough to match his stiff boy rod.

It would take several days of training on working nips hard and rough before he mastered that technique on me. I had him work my nips raw for the next four days. I applied nip clamps with a chain and loops to attach weights. I added a half pound to each nip and teased the end that was squeezed out of the clamps to get it used to rough play. I had him kneel on all fours and reached under the dangling weight and flicked them a few times. Every ten minutes I would remove the weights and clamps, then ten minutes later add them back and rub the nub ends of his tits to get them hard. I told him how I enjoy rough play and love it when my shirt causes friction on my nips and they stand hard and proud all day because they have been worked so much they ache from just a light touch of cloth.

His next lesson was to learn to suck balls. He had the cock sucking thing well in hand, but getting a good hard set of testicles ready took some time to learn. First I sucked in just one nut and rolled it around in my mouth. Then I moved to the other nut and did the same. Finally I took both in my mouth and played tennis with them bouncing them back and forth with my tongue between them. After several minutes of play, I clamped my lips down hard and slowly withdrew my head pulling his nut sack down away from his body until there was almost two inches of stretched flesh and held it there, running my tongue over the taut flesh and fully loaded balls. Then I made him shave his balls. I repeated the same treatment again on his shaved balls so he would know the difference and sensitivity. Now I had him work on my nut sack the same way I worked his. For thirty minutes each day, he would practice on my nuts. Sometimes he would reach for his cock and begin to stroke it. I had to slap his hand away more than once and on one occasion I grabbed his balls and threatened to crush them if he did not leave his prick alone. That worked. It took the boy more than a week to master playing with my balls before he got it right every time.

Now we moved to his lessons on how to suck a real man’s cock. He had enough suction power and good lip form, but he did not know how to play with and tantalize a piece of soft meat or prolong the pleasure on a hard rod. I demonstrated how to work just the mushroom head and piss slit and swallow no more nor tease any other part. Next I demonstrated how to work the ridge and veins on the underside of a cock to get it rock hard and keep it that way. Finally I showed him how to nibble on the underside of a man’s meat to work him into a frenzy.

Now the boy worked my cock. I made him dig his tongue down into my piss slit and play inside there. I had him lick the mushroom head like it was candy and wrap his tongue around the ridge of the mushroom. Now he worked just the ridge under the cap, the small half inch that is really sensitive. He flicked his tongue at it, he lapped at it, and he chewed on it. Next he worked down to the base of the shaft and nibbled there with just his lips, then gently with his teeth. Finally I had him swallow it all down to the base and run his tongue around the base and work it slowly up the shaft to the head and then work his tongue back down. We set aside one entire Saturday for him to practice and work these techniques. He worked on me from 7 Am until 6 Pm, stopping for water and soup for lunch. Using my self control I let him work only five loads out of me that day.

Now we turned to working a man’s pits. We exercised for several minutes, doing push ups, jumping jacks and sit ups. Once we had worked up a sweat, I licked his pits for several minutes, chewed on the hair and gently pulled it with my teeth. I nuzzled his pits, sniffed them, and rubbed my beard into his underarms. Now it was his turn to show me how to be erotic with my pits. First, he licked lovingly around the hair, then slowly swiped back and forth and then around all the hair, finally lapping deep into the pit. He buried his nose deep under my arm and wrapped my arm around his head to get a good solid whiff of my man sweat. He nuzzled there for several minutes then dug his tongue back into my pits and growled while he munched on my pits, hair and arms, licking my bicep and sucking on it like a baby before going back to my pits.

This boy was very good at learning; he mastered everything I taught him to date. Now came the tough parts. Rimming, fisting, getting fucked up the ass and drinking someone’s piss would take more work and patience. I wanted a clean ass so I had the boy give me two enemas. I did the same to him. Then we climbed into the shower and used my turbo anal cleaner and washed out our holes. We dried off and he got on all fours.

I spread his cheeks and alternating, ran my thumbs across his puckered hole. I spit on his ass lips and wiped it around with my tongue. Now I slowly opened his hole with my tongue darting all the way inside him as deep as I could go and wiggled my tongue around and around his insides. He squealed like a pig in heat and pushed his ass back on my tongue begging for more. I rubbed my nose and unshaven face and beard across his sensitive hole and buried my nose up his chute. Then I replaced it with my tongue. I worked the boy for a full hour. Now it was his turn to show me what he had learned. He spread my cheeks, rubbed my hole with his fingers, spit on it several times, licked it once on the outside and spread some lube around it. He inserted one finger but rimming would not come easy to him. I convinced him to place his head down on my hole, and gently blow on it. Next I had him stick out his tongue and lap around my hole but no in it. After several minutes, he finally agreed to lap right over my pucker a few times but he winced each time. Finally I reached back, grabbed his head and pushed right into my ass and told him to start licking and dig his tongue up my chute or he would stop breathing. He opened his mouth and reluctantly dug his tongue in. It would take several days for him to get used to eating my hole. He loved it when I worked his, but he had trouble eating mine. Eventually, I sat on his face and forced the issue and he began to eat ass. While his tongue is not a along as mine, it does have a stud piercing which feels great rubbing inside me.

Next up in training was fisting. This took weeks to get him ready. I lubed him and inserted a large butt plug and worked that around and in and out for several minutes. Then I moved to an eight inch plug. This took more time to work in and I duct taped it up inside him and made him walk around with for several hours to get used to the full feeling. His next lesson was a ten inch long five inches at the base dildo. I worked this in over several minutes, and let him lie still fully plugged. Once he had adjusted, I made him walk around for two days with this taped inside him. We worked out in the gym, swam laps, jogged on a treadmill, and wrestled, all with his ass fully plugged by a mammoth dildo. Now he was ready for the fist shaped butt plug that was the length of a forearm. For the next 30 minutes, I eased the rubber fist deep inside his well lubed hole. He lay on his back in the sling for an hour before he felt comfortable enough to sit up. For the next three hours, he lay back and sat up, all the time filled to the brim with a fake fist and arm. Meanwhile, I coated my gloved forearm with Crisco so it would slide right in when I was ready. Now the boy lay back, I eased the rubber fist out of him and slowly but steadily inserted my fist and forearm inside his stretched and gaping ass hole. Finally, success! After fifteen minutes of maneuvers to show him what to do, we swapped places and I got in the sling with my legs spread and ass exposed. He gloved his arm and lubed my hole and caked Crisco on his fist and forearm. HE made a fist, punched through my sphincter and in a steady push was all the way inside my love canal. I verbally guided him through what to do, how to twist and rotate, rub my belly while inside, pump in and out with his fist and spread his fingers to massage my insides and especially my prostate as he went in and out so I got huge rush and orgasm.

The next series of lessons were the easiest to teach as he had already been fucked by men for years and was experienced as both pitcher and catcher. What he lacked was experiences in different locations and environments. Most of his experience had been in bedrooms, bathrooms, locker rooms, bath houses and parks. He almost no experience in a sling, rim chair, fuck machines, group or gang bangs, outdoors or in moving vehicles. Since I had a sling, we used to teach him how to position his ass, how to sway his fuck hole so it bounced back and forth on my cock with little effort from me, on his back and stomach in the sling and holding his ankles while being pounded. I borrowed a fuck machine from a friend and using a St Andrews Cross, strapped him in and set the machine on the ground to come up and into his chute. After lubing him and stuffing lube deep inside, I put the machine in place, stuffed his man cunt with the probe and turned it on, slowly then revved up the speed. He was pounded in this manner for an hour, and then I stopped the machine, checked for sufficient lube and turned it back on for two more hours. He was stretched and sore when I turned it off and removed the probe.

Next up was outdoor and moving vehicle sex. I took him to a park where there were several trails that became remote areas. I led him to one very remote are with a picnic table under a tree. He removed his clothes and knelt on the bench, bent over the table and stretched out his arms. I secured his arms to one bench and his legs to the other. His ass was up in the air and face rested on the table with his jaw right at the end of the table. I had pre-arranged with four friends what was about to happen and they arrived on time to take turns fucking his ass and face fucking his mouth. I stood guard on the trail to prevent anyone outside form intervening. It was a four hour afternoon of sweaty sex. When we were all done, he pulled on his shorts and shirt and followed me back to the parking lot. There we climbed into the cab of an 18 wheeler and took off. He was stripped again and as we drove onto the interstate, I had him start to give the drive a blow job while I fisted his ass hole. After several minutes of this hot action, I climbed into the cab, shed my pants, and pulled the boy’s ass in my direction while he continued to suck the driver’s rigid cock. I mounted his ass and began to pound away. The drive and I came about the same time. He was filled at both ends with our seed.

The final lessons were to shave his body smooth and learn to drink and swallow piss. Shaving him was no big deal. I shaved his head, chest, pits, legs and arms. Then I shaved his ass, balls and man bush. Lastly, I shaved off his eyebrows. Earlier in the day, I took a piss in a cup and now the boy was to sip from it. First he got his tongue wet with it. Then he took a small sip. Next a small gulp and finally a larger and larger gulp until he was ready to drink from the cup. Once he was used to the acrid taste, he was fine. Now for graduation, he was to drink directly from the stream coming from my penis right into his mouth. I started with my dick in his mouth and let go a short stream. Then another short stream and finally let go the rest right down his throat. He opened his mouth wide so I could shoot my stream directly down his throat.

Happy graduation!


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