I was told yesterday that a new guy was starting in the office as a senior salesperson -- Charlie. I am also a senior salesperson. Never would I have believed that this was the same Charlie that I went to prep school with over 30 years ago. In fact, he had me so bullied and intimidated that he was the reason I left the school.
I'll start back then. He was one of my roommates. After a couple of months, talking to me like I was nothing and ridiculing me in front of the other 2 roommates, he just told me once privately in a soft-spoken voice "Jimmy, I'm going to give this to you straight. I don't like you. You annoy me. And I'm going to beat the crap out of you at least one day a week.
I knew I couldn't protest or report him. I would be the laughingstock of the school. I brushed it off.
He said "Jimmy, this is quite serious. Should we do this the easy way or the hard way. One option is that I just beat the hell out of you. If I do, I'm going to strip you first. Then after beating you up, I'll tie you up for 2 hours. That will be once per week on Thursdays after athletics in the afternoon."
I started stammering. He said "Shut up. The other option is simple. We can do it privately. If I share it with the other roommates or someone on the hall in the dorm, I will be sure they keep it private.
"Wh..What?"
He knew he had me. "On Thursdays at 3pm --and I mean you got to be prompt -- you come back to the room and be stripped naked for a spanking. Then you remain in the room naked until the next morning. You skip dinner. You just do your homework nude in the room. During that time, if I give you anything to do like typing my papers or doing my homework or doing my laundry, you do it. No questions asked. Deal?"
"I've got to think about this," I stupidly said -- giving him the upper hand.
"Jimmy, if you walk out of this room without agreeing (it was exactly 3pm on Thursday when we were talking), without removing all your clothes, and without getting into the position I tell you to, then the deal is permanently off. That's fine. As you know, I'll have no problem at all ripping off your clothes and beating the hell out of you. With my proposed plan -- the spanking -- the only marks will be on your ass. Otherwise, everyone will know from the marks all over you that you've been beat up. We can even figure out a time for you to shower between Thursdays and Sundays when you butt is still red and marked."
I started to walk out. He grabbed me, and literally ripped off my shirt. I said "All right. But I'm just stripping to my underwear."
Charlie said "Jimmy, we're getting off to a bad start. I don't negotiate. I'm counting to 25. If you aren't stripped naked and bent over with your hands clasping your knees, then it won't be nice picture."
At the count of 25, I was naked and in position. At his orders, I was counting each belting since he had already taken off his belt. He never raised his voice. He was as casual as if he had asked me to turn on the light.
By the evening, since I was sitting in the room typing his long term paper naked, the roommates knew exactly what was going on.
By the next week, half the dorm knew what was going on. People stopped in to chat with Charlie and the roommates -- smirking but never making any reference to my situation. When I said I was going to the dining hall on the third week, Charlie asked the other 2 roommates to please excuse us.
At that point, Charlie said "Jimmy, bend over."
I said, "All right, I'll skip dinner."
Charlie said "Bend over. One thing I don't want is insubordination. That includes asking for something that I've forbidden you to have. Your responsibilities on Thursdays from 3pm until bedtime are to complete the tasks I give you. Now take my laundry down to the laundry room now -- that is, as soon as you get the extra 25 lashings with the whip I bought this weekend.
It was excruciating. I couldn't help the yelling and screaming and pleading with him to stop. And the whole dorm could hear the first half. Then after the 14th whip, about 12 guys were standing at the door watching.
Noticing my hard, Charlie added one more rule. I was not allowed to j. o. In fact, he decided that he would increase my erection ever so carefully so it was noticeably hard. If I even considered touching it myself, it meant 50 extra on the ass.
I reached for my robe to put on before going down to the basement laundry room. "What the hell are you doing? he asked with every one of the same guys still standing there laughing hysterically.
"I'm doing your laundry." I said.
"You're doing it stripped naked. You know that. so that you don't try that again, walk over and get me the ping pong paddle. It was down the hall about 75 feet. Now another 30 or so guys could see me walking naked with a huge hard sticking out. It was like they were in a comedy club, they were laughing so hard.
This time he pulled me over his knee. At least 50 times with the paddle. He starts to take off his belt, and I run out of the room with his laundry. The laughter is going like crazy, and Jimmy has this smug, sarcastic smile.
Each week when I did his laundry, I didn't know which was more embarassing, waiting down in the basement stripped with all the people coming in and out, or going back and forth to the room while the laundry machines were running.
Eventually, Jimmy and the others were taking photographs of me getting whipped, doing laundry in the nude, and who knows what.
Any typos on his papers meant an extra whipping. One day I was doing his homework on a Thursday afternoon and Don from down the hall said that Charlie called him (Don) to say he's been delayed and Charlie wanted Don to administer the spanking in Don's room -- and Don had a few additional chores for me. I refused.
Don said that was fine. He would go to the athletic field and get Charlie, who would be furious enough to increase the Thursday program to at least twice per week. I walked up to Don's room. Don tied me to the bed, legs and arms and belted me so hard I was beside myself with crying and pleading. After handing me his laundry, he said while the laundry is running in the machine for me to come back to do nude calisthenics to his counting -- in the hall. This spectacle brought guys from all over the dorm.
Meanwhile, Don had locked me out of my room. So when Charlie got back I was standing outside of the room naked. "What the hell are you doing? he asked. I said when Don followed through with his instructions, I got locked out.
"Who is Don?" Charlie asked. It turns out Don had made up the whole story.
When I walked down to Don's room (Charlie said I still couldn't put any clothes on), Don was laughing. As I started to tell him off, he pushed me down and said "Lie on the floor. Spread your legs. and keep quiet." He took off his belt and went on belting me 75 times at least. Then he said turn over on your back. Spread your legs. Spread your arms above your head and stay like that until bedtime."
Don and Charlie became friends. And Don filled in when Charlie was busy.
I left the school permanently at the end of the year. Now, I just find in the staff meeting (over 30 years later) that the same Charlie is a senior salesman that I have to work with, attend meetings with, and visit sites with.
This afternoon (Friday), Charlie called me into his office. "Jimmy, sit down. I know this is awkward for you. I'm going to keep it simple. I have a deal for you. No options. This is it. I still have the photographs from prep school. You are very recognizable in the pictures. Let's face it. You look the same -- still thin, handsome, good shape, full head of hair. I'm perfectly glad to not show the photographs to anyone here under a few simple conditions."
"Screw you." I said.
"Fine. Walk out the door and the offer is permanently off. No 2nd chance. Everyone here -- and your friends who live here in the area -- will see them. Good bye."
"Now wait a minute."
"Good night, Jimmy."
"All right, Charlie, what are you proposing." I said.
"Jimmy, I know you have a great apartment. I need an apartment on Friday nights to spend with my girlfriend (who my wife doesn't know about) through late Saturday. I want you to strip naked on Fridays at 6pm in the conference room. I'll give you just a standard whipping -- paddle one week, whip another week, belt another week. Since the cleaning crew doesn't come in on Fridays, you'll remain in the conference room until late Saturday -- staying stripped. Once I come by here on Saturday with the key to your office, you can leave."
"What the hell are you talking about?" I said. Even if I let you use my apartment, why would I go along with that?"
Fine. Good night. I'll start distributing the photos this weekend instead of spending it with my girlfriend.
"All right. Fine. I'll do it, you bastard." I said.
"There's more, Jimmy. I want you to go to sleep Friday nights (in a sleeping bag) in the conference room early. then on saturdays, you'll do my ledger reports for me. Then on Monday morning, I want you to speak with the boss and insist that I have senior status supervising you in the office. You will tell him that you realize I have more experience. One last thing. Make sure the apartment is immaculate on Friday evenings. You inspect it when you leave after making sure it's spotless. Fresh sheets and everything. I'll give you a list of what to have in the refrigerator. Then on Saturdays when you get back, be prepared to clean up. We may be entertaining other people. Got it Jimmy?"
"Charlie, I can't do this." I said
"Jimmy, you know I don't fool around. Walk out the door. Good night. The deal's off. How do you think everyone will enjoy the photographs?"
"All right. I'll do it."
"Well, Jimmy, since you refused at first and I said it was a one time offer, I have to add something to the deal now." Charlie said smugly.
"What, Charlie?"
"We'll add an hour of naked calisthenics to occur before the whipping each week. You've got 5 minutes to strip, lock all your clothes inside your office, and give me the key."
"Charlie -- I've g--"
"Jimmy, move! I'm more short-fused than I was in prep school. And remember, you stay stripped naked, you stay in the conference room and this week just like on the floor. you don't really need a sleeping bag. When my girlfriend and I get here tomorrow, i want you lying on your back on top of the conference table, arms raised high above your head and legs spread wide. The earliest we'll get here will be 5pm so get in that position at 5pm and don't move. if it's 9 or 10, then it just means we got delayed. and don't give me any crap about being seen naked by my girlfriend. that's the way it is."
"this is ridiculous, charlie"
"it's ridiculous but you'll do it."
I left my clothes in my office, walked back to the conference room naked. sure enough, he ran me through an hour of push ups, situps, jumping jacks (with my prick flopping and charlie amiling). then he doubled the amount of the whippings (he had actually bought a whip today). i was screaming, crying, begging him to stop. then he just walked out like it was nothing. he called an hour later just to say that today's calisthenics and whipping in the conference room were on videotape (he took the tape out before he left) so no matter how mad i decided to get, that tape would be quite unpleasant for me should he decide to show it around -- which, he said, he would (since he hasn't had the prep school photos for over 30 years).