I recall being hired as a cottage supervisor at the rural Bellville School, an institution for unmanageable boys age 16-20 whose being remanded to less strict supervision had proven useless. Upon my final interview with the head master I was told that liberal amounts of spankings and whippings would be required if I were to have the intended effect on the boys. Passing muster on this and other counts the head master told me I was hired and that my services would be needed immediately.
Hoping that I could begin my duties immediately after the interview I had brought along my clothing and other belongings, so immediately I set about moving into the cottage master's quarters in Building 103. Then, all settled in and reading several newspapers on which I was behind in reviewing, I heard a knock at the door. I opened it to find a tall clerk, his name was Patrick, standing before me. He was a good-looking chap, about 28, and obviously reluctant to bother the new cottage master so soon after his arrival at the school.
"Pardon me for bothering you, sir, but we have one of your boys in office detention for trying to start a fight in the gymnasium. The head master asks that you come escort him here for proper punishment."
"Thank you, I'll accompany you," and we began the short walk back to the head master's office.
"A lot of the boys here don't seem to understand anything but being strapped or caned, sir," said the clerk as we walked into the office and he introduced me to the offender, a boy of 19, slender and well-built, still wearing his gym shorts. "Chaz, this is your new cottage master, Mr. Simpson. He will take charge of your punishment now."
Chaz had a demeanor that bespoke him being punished on many previous occasions--a bit _c_o_c_k_y but still somewhat uncertain what he would be facing with a new cottage master wielding the rod. "What was it you wanted to fight about with the other boy," I informally asked Chaz as we passed through the front door of my quarters on Cottage 103's first floor. I avoided conducting a formal interrogation, choosing instead to talk with him person-to-person in getting an idea of what had happened and as to what corporal measures would be appropriate. I wanted word to get around among the students that I was a firm disciplinarian but not one who meted out strokes in a haphazard fashion.
Chaz told me the argument had arisen over who would be team captains for the the afternoon's basektball game, that the other student had shoved him, and that he (Chaz) then challenged the other boy to a fight for the right to be captain. He further related what followed was a shouting match in which Chaz became really angry and knocked the second player to the ground. At that point the physical training instructor walked in and ordered both boys to the office. The other boy was taken to his cottage master and Chaz was meeting his.
Inside my quarters I told Chaz, "The rules say you have committed an offense that requires corporal punishment. And you will receive 70 strokes of the strap and cane. I'm new here but don't think for that reason you'll receive any grace. Now come with me into the punishment room."
Once in the room, I told Chaz to remove his gym shorts and assume the position over a whipping stand that was in the center of the floor. As he dropped the shorts I couldn't help but notice the shapely form of his legs and buttocks, lightly covered with blond hair. Before he arrayed himself over the stand I informed him that the 70 strokes would be divided equally between the strap and cane and that the strapping would be on his jockey shorts and the cane would be applied to his bare bottom. "Now let's get on with it," I said, ordering him to lay himself over the whipping frame.
As Chaz lay over the upraised center bar, hands grasping leather loops attached to the frame itself, I picked up a junior cane and walked around to his left. I reached down to adjust his position and in lifting him at the waist of his cotton briefs noticed that he had a firm erection. Then I patted him on the rump and said, "Here we go."
I laid into him with 15 heavy, steady strokes of the strap Pausing, I asked him if he understood the necessity to remain calm when challenged by such people as contendors for the team captain's position and that discussion, not violence, was the proper way to solve the disagreement. He said that he did realize that. "Good," I in turn said, "now let's get back to our business." Another 15 of my best followed, by which time young Chaz was beginning to feel the burn of the strap considerably. I said then, "You are about to receive the final five strokes of the strap, then we proceed to the cane.
He took the remainder of the strapping with a bit more discomfort, but still held up well, but then he'd had a lot of practice being under the various implements of discipline at Bellville. Putting down the strap I approached Chaz from behind and told him to put his legs together and remain in position while I stripped him of his jockey shorts for the caning part of the punishment. I took his underwear by the waist band and began to work the jockeys over his shapely butt and long, well-defined legs. My hand brushed the inside of his thigh where his balls and erect penis lay. He issued a sort of half moan as he again spread his legs, affording me a clear view of his manly virtues. With the briefs now on the floor Chaz stepped out of them and I moved them aside, then picked up the cane.
Chaz seemed to half enjoy the corporal measures, so I decided the first twenty stroke of the cane would give him a special ration of peasure. I had him spread his egs further just before administering the first 20 strokes without stopping, one every ten seconds. Those 20 completed, Chaz was told to stand away from the whipping stand and bend over and hold his ankles. Doing this yielded another close look at his balls and still-erect penis. Picking up a smaller and more flexible cane, he took the final 15 with little more apparent discomfort than he had all the strokes up until then.
As he turned around to face me I saw his stiff seven inch penis which he made no attempt to hide, nor did he move to retrieve his jockey shorts nearby on the floor.
"You know, sir, you lay on the strap and cane about as well as any cottage master I've had whippings from. And I like the way you didn't insult me with all maner of demeaning questions before the whipping began. I think the others of us in your cottage will not mind so much receiving punishment when everyone knows you have a proper mind about it." He paused for a moment, and continued, "Also, sir, some of the masters here apply lotion or salve to our buttocks when they've finished punishing their boys. Would be of the same mind?"
Being somewhat taken aback by his statement I told Chaz that his resiliency in receiving his punishment had been admirable and that the least I could do would be to accommodate his request for medicine to be applied to his red hot buttocks. Retrieving a large tube of ointment I reqested that Chaz accompany me to the bedroom. There I sat down in an easy chair and asked him to lie across my lap so I could apply the medicinal compound. As he lay there I began squeezing the ointment onto his burned buttocks and massaging it into the skin, which showed only a few small breaks in the surface. I was careful to avoid the anal region but was close to it when Chaz said in a low voice, "Having some there would feel good, also."
Spreading the creme over his anal parts I slowly applied more pressure with my finger until it just penetrated his opening. He moaned rather loudly and asked me to insert my finger further into him. I did so until all of the finger was deeply planted into Chaz's rectal area and he was continuing to groan in pleasure. While slowly running my lubricated finger in and out of him I reached around his waist with my free hand and took his blood-engorged penis in my hand. He was rock hard and asked if he could turn over. I told him to get on the bed on his knees and to lower his shoulders. He did this as I positioned myself immediately behind him and reached between his legs, first stroking his large balls, then placing my thumb abd fingers around his throbbing, hit penis. As I stroked him more intensely, Chaz begn to move his hips back and forth, magnifying the length of each stroke. With the other hand I was drawing long, gentle strokes of my fingers across his balls. This continued for another 15 minutes, when I could feel both his balls and penis begin to tighten up considerably. He then spread his legs a bit wider apart and became motionless. At that point he began to squirt huge amounts of cum in and on my hand. The ejaculation continued for ten or 15 seconds then Chaz collapsed on the bed, outstretched fully, and moaning continuously.
I looked at the clock and noticed Chaz had been in the punishment session for 90 minutes. I approached him with a wash cloth and had him bend over in front of me while I cleaned away the ejaculate. He still looked good to me and probably will each time he receives punishment.
As we walked to the door for him to return to his room Chaz said, "Good work, sir, I feel another streak of misbehavior coming on now." I told him I was sure we would meet again very soon.
Then it also occurred to me that I needed to see Patrick, the attractive office clerk, but that's another adventure that will be related in Part Two.