The following story is fiction about two men seeking release from a grueling work week. This is second of four parts of the story and the characters are defined in Week 1: Getting Off which should be read first. The story contains a scene of a strapping and gay sex. If these subjects are offensive, uninteresting or if you are a minor (i.e., child) please leave now. I hope that you are smarter than my characters and take proper care to prevent STD's.
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It had been a hell of a week. One I was not proud of for I had fucked up several times. Fortunately, the foreman had not realized that it was I who wrecked his production goals and I had gotten away with the shit. Nevertheless, I was not happy with myself. Can't say I would have like to be have been sent to HR but then I would not have such guilty feelings as I do now. I would be, instead, unhappy about the lightness of my pay envelope. OK, it's really a check but cut me some slack, will ya – it has been a bad week.
When I left work, I was starved but I didn't have any appetite so I stopped in the dinner on my way to the subway and got a burger and fries and a large beer. A man gotta keep up his strength for one never knows what might cross his path. Then I headed home. I was still down but at least I had a full belly and maybe after a nap I would go out. My mood was not helped by the subways delays but I got home anyway. I showered and was about to collapse when the doorbell rang. Strange. Well, perhaps a neighbor or the super with a package. I tightened the towel and opened the door.
It was a kid. He looked like a high school freshie. He checked my name and handed me an envelope as he eyed my hot bod. I bet he was also wondering was hidden behind the towel. Well, he was going to have wonder a long time since he was definitely still jailbait. But in a couple of years, he might be fun to spank and fuck. I glanced at the envelope, saw that it had my name on it and then when I looked up the kid was already going down the stairs. Strange, he did not need a signature.
I opened the envelope and extracted a single piece of paper. It was not the standard letterhead head size but only five by six inches. In heavy bold letters across the top was: Southmost Union High School with an address. Then, also in bold, Disciplinary Report followed by a batch of check box options after my name. It was just like the nastygrams I had gotten in high school. It gave me a strange feeling in my stomach. This one had missing homework, insubordination and disrupting class ticked off as my crimes. Then, finally, Report to VP as the 'action item' rather then detention or a couple of other possibilities. It even specified a time just an hour away.
A week earlier I would have immediately dismissed this as a silly joke that did not make any sense at all. Now, however, I thought about my encounter with the rich guy last week. The chauffeur had said he would be in touch and this was a neat way to set up a scene. His timing was great – I was feeling bad because I had fucked up and he had set up a situation that was perfect to help me get over it. I did not worry about how he knew or if it had just been a happy coincidence.© YLeeCoyote
How to dress was my immediate problem. I chose a rock band T-shirt, loose jeans and sneakers. I dug into the dark recesses of my closet to find my old HS jacket. I skipped underwear because back in school it was fun to go commando.
As I headed down the stairs, I realized I did not know where to go. There wasn't any real address on the DR nor did I know where I had been last week. I had pretty much decided to go back to The Place where we met week. I was early enough that the dress code would allow it. I should not have worried for in front of my house was his car and driver. He hit the horn as I stepped out and I got in. All he said was "Buckle up, kid." as he drove off.
When we got into the garage, he handed me a note with instructions. It gave me a room number and said to wait on the bench until the VP called me. The apartment door was unlocked and inside I saw a bench by the door to the room that had been the coach's office last week. There was a sign on the door: "Office of the Vice Principal". I checked my watch and saw that I was ten minutes early. I hoped he would be on time.
Fifteen minutes latter, he came into the hall and used a key to get into his office. He turned to me and said: "I'll call you when I'm ready for you, Dobson." I sat another seven minutes before he summoned me with a loud bellow.
I entered the room which now was setup as a VP's office and he was still in his suit. I sat, as directed, in the plain chair directly in front of his desk. I did not see the paddle but there was lots of room in his desk for it. He opened a file folder and looked at some papers. I was reminded of how my HS VP, Mr. Radermacher, had done the same thing. Then I saw the name plate on the desk. It sent a shiver down my back for it read: "J. R. Radermacher".
Then he gave me a scathing lecture. He may have been taking high school stuff, but I was hearing about the fuckups I had committed at work the past week. He paused and checked the file again. "I practically have enough here to expel you and certainly enough to suspend you, Dobson." He was talking serious stuff now. "That's not going to do you any good, is it, Dobson?" He did not wait for an answer but just reached into his desk and took out a heavy strap. It looked heavier than a belt and lighter than a razor strop. "There is another option, boy." He looked very stern through all of this.
"Yes, Sir." I said. "I'll take the alternate way, Sir."
"Strip, boy and get into position over the desk. I guarantee that you won't forget this strapping for a long time." We both stood up and I started to strip dropping my clothes on the seat. He hung up his suit jacket and removed his shirt and tie. Then he cleared his desk and I leaned over it. He had me put my hands down near the floor and then slipped some ropes about them. "I don't want you moving at all during this, boy." he said as he clenched the ropes to keep me in place. Well, I was irrevocably and totally committed now.
He walked around to the other side and I felt the strap on my bare naked butt as he checked out his position. Then he gave me the first cut. It seared me like the strap was made of red hot steel and I yelled. He gave me two more just as hard. I was in agony. I was pleading for mercy. If I had not been restrained, I would have jumped up and stopped him. But he was in control and I already knew that I would never forget this strapping.
"That's only half way, boy." he said. "Fear not that I'll keep my promise that you won't forget this strapping – ever, Dobson." Then the fourth cut landed and I yelled again. It did not do any good for the fifth and sixth cuts came right behind. I could hardly believe how much my ass was burning. I was even beginning to sob and I'm sure I would have been crying if he had continued. Then I felt his hands on my fiery butt and knew what was next. There was no way I could stop his fingers from penetrating my ass as I was in so much pain not that I wanted to. Of course, last week I never asked him if I might fuck him.
He was kind and worked my hole with his fingers until it dilated when he rammed his fat cock deep into me without any further warning. He had the angle just right and his rock hard love bolt hit my love nut dead center again and again. He drove my senses off scale. He fucked me long and hard before he came. I came explosively a couple of times without my cock being touched at all. I just stayed in position trying to recover as he dressed. He put the strap back into the desk and untied me.
"My driver will take you home like last time. He's waiting in the garage." He left without another word. I used the towel that was on the desk to clean up and got dressed. I was glad my jeans were lose fitting because my tail was on fire. The chauffeur was waiting for me and even opened the door for me. As he got into the front, he asked: "Home, Sir?"
I said: "Yeah." and he drove off. Once home I filled a bag with ice and lay down with it on my blazing rump. I was exhausted and fell asleep even with the pain.
When I woke up, my ass still hurt but I felt much better. I had gotten exactly what I had needed. I knew that I would not forget the experience for a very long time.
© Copyright A.I.L. February 20, 2010
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Last updated: September 15, 2023