Jay's Letter to Red Caboose
as Ordered by CPBoss

Red Caboose--

CPBoss disciplined me last Tuesday night and instructed me to send you a report on the punishment he gave me; this is that report.

I was to be punished because I had gotten a speeding ticket. CPBoss instructed me to wait for him in my motel room. I had arrived early. CPBoss called and told me he would be there in a little over an hour. As I waited I got more and more scared. CPBoss had punished me before, and I knew I could expect a painful, humiliating session. I was concerned about whether I could take the punishment I deserved without hollering. CPBoss is a strict authority figure, and when he punishes a boy he makes sure it gets the boy's attention and teaches him a lesson. I've got a tough butt and could just laugh off a whipping (I use "whipping" generically, without regard to instrument) from most discipline daddies, but CPBoss is another story; when he whips a boy, he doesn't fool around. It's PUNISHMENT--bare ass from the get-go, no warmup, and the real thing -- no easy licks. So I was scared because I knew it would hurt like hell. But I had fucked up and gotten the ticket, and now I had to take the consequences. And my dick told me I wanted it too. Still, as it got closer, I got more and more scared, waiting, playing solitaire on my laptop computer.

Then came the knock at the door. I let him in. CPBoss is an attractive, hot looking man. It was clear he was a man with a purpose -- paternal responsibility -- and a mission to give me the correction I needed.

CPBoss got right down to business. He interrogated me about what I had done, which, to make a long story short was 76 mph in a 65 mph zone, for a fine of $52. He reminded me it wasn't the money. I had broken the law. I had compromised the safety of myself and other motorists. He reviewed these facts and made me acknowledge them, which humiliated me. He asked me if I had anything to say for myself. I hung my head in shame and murmured, "No excuse, Sir." He replied, "You're right boy; there's no excuse for it." He ordered me to strip for my punishment. When I had taken off everything, including my socks and watch, he put a condom on my soft dick and instructed me to get over the bed with my stomach on the pillow. He asked if I thought I could take the whipping without being tied down; I answered yes. He ordered me to spread my legs and clasp my hands over my head. Failure to keep my hands in place, he warned, would mean the particular set of licks where it occurred would be repeated. When he saw that I was in place, he rubbed an oil-based lotion into the skin of my buttcheeks. He didn't say why, but I knew it was so the strap would make maximum contact. Then he went to his bag of punishment implements. I didn't see what he got out; turning around to look would have meant extra licks.

Returning to the side of the bed, CPBoss pressed hard on the back of my right knee with one hand and delivered the first lick with his other. It was a thick, narrow strap of some kind, and it hurt like shit! This was the first lick, and I cringed in fear of the punishment I now knew I was facing. I trembled and felt my face contort in what could have been a crying expression. I would have been bawling if I were a kid. I've often heard it said kids don't cry until the second lick -- they're in shock with the first lick. Don't believe it. With a tough punishment master like CPBoss, a kid would bawl from the first lick -- I almost did!

He continued to lay that strap across my butt, and everywhere it hit it felt like a red hot poker. The lotion made it a lot worse. He must have given me 25 or 30 licks with it before he even paused, and by that time my ass burned like I had been exposed to radiation.

Then CPBoss selected another implement. I later learned it was a short, thick rubber strap he had gotten in Toronto. Maybe I was warmed up, maybe it was the instrument, but it didn't seem to hurt quite as much as the first strap. It was no piece of cake, but all in all, I could take it pretty well I thought.

After a long round of licks with that instrument, CPBoss ordered me to my feet and told me to face the bed, bend over with my hands on the bed and my legs spread. He then gave me a round of licks with two paddles. The first was a thick, narrow one with a sort of rough surface that hurt like hell. The second was a regular frat paddle with a varnished surface. It had a real kick to it. By this time I was getting into my whipping; this was reflected in a half-mast erection.

CPBoss then ordered me to stand at attention. He told me to look at my ass in the mirror; I tend not to get very red, but the punishment he gave me had turned my butt SCARLET. Placement was perfect: all over my ass, no red marks elsewhere. Then he "took matters in hand". First, he held my dick and squeezed my nuts until I was practically yelling. He also smacked my dick with the outstretched fingers of his other hand. Then he jacked me off, getting me to full erection. Remember, I was wearing the rubber he had put on me at the beginning. I got more and more into it, and he kept up the jacking. Finally, I reached the point of no return. CPBoss had made me cum in the rubber. After allowing me time to compose myself, CPBoss removed the condom from my dick.

You may think you know what was next, but you'd be jumping the gun, as it turned out. The next thing turned out to be real punishment for me. Total humiliation and disgust. CPBoss ordered me to lick my cum out of the rubber and swallow it. I would never have expected to feel as humiliated as I did. If I had been a teen-ager, I suspect I would have protested, finally given in under threat of more severe punishment, and sobbed quietly as I did it. As it was, I found myself grimacing and exhaling emphatically in short bursts -- exactly as if I had been sobbing.

Now to what you thought was coming. The old adage, of course, is that a whipping feels a lot worse when you've just cum. Maybe my endorphines were still flowing. Whatever the cause, I was not, shall we say, unexcited by the prospect of more ass beating. The difficult part, though, was the implement CPBoss used on me. It was a thick rubber paddle made from a truck mud flap mounted on a wooden handle. Fuck, man! Licks with that sucker were enough to make you want to jump out of your skin! That instrument would be appropriate for heavy-duty prison use! After several starter licks that would have made anyone but a punishment glutton cry like a whipped puppy, CPBoss told me to start counting the licks. Then he started laying on the licks really hard. One, Sir. Two, Sir... Ten, Sir.... Fifteen, Sir.... Twenty-five, Sir... Forty, Sir... It continued up to 65, the speed limit. CPBoss taught me the speed limit, 65, with that heavy rubber paddle. He then gave me the extra five licks to bring the number up to 70, the new speed limit (I'd gotten the ticket under the old limit). Man did he make my ass smoke!

Then CPBoss made me lay on the bed while he stuck a dildo in my ass -- with NO LUB. I'm not used to getting fucked or having things put in my ass, and the very idea of that dildo dry, with nothing to ease the insertion, had me grimacing and almost crying again. CPBoss had not fully expected my reaction and impressed on me that this was PUNISHMENT, and I was to "Take it, boy!"

After getting the dildo, I was given additional whipping. CPBoss used a twin-lash whip made from a thick leather jump-rope. He first used this on my butt, but, while it hurt a lot, it did not elicit a full reaction from me because of the punishment my ass had already received. Seeing this, CPBoss made me kneel in front of him next to the bed and laid the lash across my back. This hurt tremendously, and I was afraid it would make long-lasting welts. My fear and pain was reflected again in my grimacing and dry sobbing. The punishment was effective. It harkened back to the one time my father had whipped me across my back. I had talked back to my mother; he heard me, grabbed me, dragged me outside, broke off a switch, and laid about a dozen smart licks with it across my back, over my shirt. Adult punishment for his teen-aged boy. Now CPBoss was applying the lesson in a new context, and he almost had me bawling. (This whip made red strips across my shoulders but no welts. The stripes were gone in the morning.)

After this, CPBoss rewarded me by allowing me to suck his condom-covered dick. He fucked my mouth and made me keep at it when I choked. It harkened back to the first man-to-man discipline I had experienced, when the topman had allowed me to suck his dick. I fucked up somehow -- now sure just how -- and he grabbed me by the hair, jerked my head back, gave me a hard smack across the face, and told me, "You can do a better job than that!" That smack shocked me and made me feel deeply humiliated. But it also taught me the potential sexual turn-on of humiliation. Of course, Dad had smacked me good a couple of times when I mouthed off as a kid, so it harkened back to that. Not every boy needs or responds well to that type of treatment; it just happens that I do. CPBoss knows that one of my biggest turn-ons is a hot mean-looking leather-clad topman lunging his big hard juicy dick, ordering me to get down on it, and holding a strap ready and eager to lay it across my back if I fuck up in any way.

In due course, CPBoss rewarded me by shooting his load into the rubber in my mouth.

Jay