When it rains it pours. That summer I had been in a real jam. First the air conditioner went out and had to be replaced. Then the water heater, and then the last straw, the transmission went out on my car. I had canceled my vacation and still wasn't going to make it. I had bought my first house a year earlier and was sure I wasn't going to have it another year. I had three bedrooms and a study so I decided to bite the bullet and get my first roommate. Somehow, I ended up with two.
I had told Joe the room was his. He was a twenty-four year old mechanic. He worked 3-11, so he wouldn't be around much when I was there. He would be coming home from work just as I was going to bed and he'd be there during the day to watch things so I thought it would work out great. He was straight but he didn't have a problem with my being gay. He was also sexy as hell. Naturally muscular, with dark hair and a rough look, but he as soon as he started talking you knew he was laid back and easy going.
A week after he moved in Joe asked me what I would think about having a second roommate. His friend Sean needed a place to stay. Sean was twenty-six and working on his masters degree. Sean was gay and really seemed together for his age. He was way more together than I was nine years earlier when I was his age. He was tall with dark blonde hair and long legs and a strong chest. He was extremely outgoing and had a great smile.
Everything was working out great. Our schedules worked out perfectly, we didn't get in each other's way and we were usually only in the house all together once or twice a month on weekends. The third month, I Joe was late with his rent for the first time. He hadn't said anything about it and I was trying to decide when to say something when he came to me. He told me he had lost his job, but he would have some money coming in a week and he'd give it to me then. The next month he was late again. And then in November he hadn't paid me and hadn't said anything and it was the eighth.
On top of that Sean had come to me the day before and told me he had to pay for his next semester and asked if he could pay me everything for December and January on January 5th.
"Hey John, I'm a little short right now, I get paid a week from Friday and I'll have it to you then. Late charges and everything." Joe said casually.
"This is becoming a regular thing, Joe. I didn't get roommates because I needed company. I need the money. When you're late it screws up my bills."
"I know man, I'm really sorry. It won't happen again. I'll pay the late fees." Joe told me. It was the same thing he had told me the month before.
"The late fees don't get my bills paid on time. That's not a favor to me. That's part of your rental agreement. It's supposed to deter you from being late but it's not working." I said. "I don't think this is going to work."
"Dude, come on, you're not thinking about throwing me out are you?" He asked. He seemed genuinely scared and I couldn't help but take advantage of the situation.
"Like I said, it's not working out this way. The late fees are supposed to be deterrent to keep you from being late. Maybe you need a stronger penalty."
"What do you mean? A higher late fee?" He asked.
"No, that would only get you further behind. Maybe a stronger punishment."
"I can do more work around here." He offered. "Pretty much anything you want."
"So you'll accept your punishment?" I asked. "It'll be a punishment you won't forget and you'll be more likely to remember to have your bills ready on time. If you agree to that, then you can stay. If not you need to make other arrangements." Joe didn't say anything. "You think about it, Joe. If you agree, meet me in the kitchen in fifteen minutes." And I got up and left the room. I was shaking. I couldn't believe I was acting this way but I was more turned on than I had ever been. And then another idea hit me. Sean was in his room studying. I knocked on his door.
"We need to have a house meeting. Can you be in the kitchen in fifteen minutes?" I asked.
"Sure." Sean answered.
I found them both in the kitchen when I came up from the basement.
"Have you made a decision Joe?" I asked. Joe looked at Sean and then at me.
"Yes. I want to stay." Joe said quietly.
"Joe has been late three months in a row with the rent Sean. And now you tell me you are going to be two months late. I'm sure you realize this puts me in a bad position with my bills. So Joe has agreed that starting today he will accept a new punishment for being late. I'm hoping this will help him become more responsible and I want you to see it so that you know what's coming if you make a habit of being late. Let's go downstairs." I said and I led them down to the basement.
I had unlocked the door to the room off the main basement. Inside there was a sawhorse that I had thrown my old futon mattress over. On each leg was a leather restraint.
"OK Joe, Strip." I ordered. I walked over to the cabinet hanging on the wall and opened it. Inside there were two paddles. One was a Jokari Paddle. Jokari is a round paddle. It's wider than a ping-pong paddle, and much thicker and heavier with a rubber grip. The other was a frat paddle with several holes drilled into it and the words bad boy carved through.
"John, come on. You're not serious." Sean said.
"Do you want to take his place Sean?" I asked. "You're late too. As a matter of fact, I want you to strip as well. Strip and sit in that chair and watch and wait." I told him. "Unless you'd rather find another place to live."
Sean looked at me in disbelief and then he pulled off his shirt. He kicked off his shoes and began taking off his pants. Joe paced nervously. He began to take off his shirt and then he stopped. He was completely frustrated.
"When I give you an order you need to answer me 'Yes sir.' Now Strip." I told him. Joe looked down and quietly answered "Yes Sir." And he took his shirt off. I looked over and Sean was stepping out of his pants revealing his long strong legs. He pulled his briefs down and revealed a thick dark blonde bush and his long thick cock. He was definitely excited. I don't know if it was from stripping in front of us, or what he thought he was about to see but he was definitely excited. Joe was out of his jeans and stood in his underwear. I shot him a look and he pulled them down and kicked them off and stood trying to cover his dick. Sean took his seat in the metal folding chair and hugged himself trying to keep any warmth he could in his body.
"I need you to step up to the sawhorse and bend over it." I instructed Joe.
"No way." He protested. "You ain't going to fuck me."
I grabbed his face and looked into his eyes. "This is a punishment. Me fucking your ass would be a reward. Now step up to the saw horse and bend over it like a good boy." And I pushed his face away. Joe looked at Sean and Sean immediately looked at the floor. Joe stepped up to the sawhorse and bent over exposing his ass. I bent down and attached the leather restraints to his ankles. His legs were spread and his ass was slightly pulled apart revealing the thick dark hair there. Joe was still trying to hang onto what cool he had left but his round globes were quivering. I caught Sean staring at Joe's ass and when he realized he was caught he quickly looked down at the floor.
I walked over to the cabinet and took the Jokari paddle down.
"Joe, this is the third month you've been late on your rent." I started.
"Yes sir." He answered. I could tell his mouth was dry.
"You're eight days late already and you told me it's going to be twelve more before you can pay me. That's twenty days late, is that right?" I said. I walked to the front of him and let the paddle hang right in his face.
"Yes sir. But I told you I'm sorry and I promise, it won't happen again." He said quickly. I put my arm on his shoulder.
"I know it won't Joe. And I'm sorry too, but we have to make sure. So twenty days late and last month you were six days late and the month before that it was nine days late. Thirty-five days late total, right?" I asked. There was a pause before Joe answered quietly. "Yes sir."
"So, your punishment is going to be thirty-five swats with this paddle." I laid the paddle down next to Joe and began pulling my belt off. "I'm going to give you a warm up first with my belt and then a clean up with the other paddle hanging there. This is a warning so you don't put me in a situation where I have to do this again next month. Do you understand Joe?" I asked as I walked around behind him. I let the belt run up the crack of his ass and watched the gooseflesh react.
"Yes sir." He answered.
"And you are ready to accept your punishment?" I asked as I continued to tease his ass with the thick leather belt.
"Yes sir." He answered quietly. I waited until his ass relaxes slightly and raised my arm and let the first blow hit. Right across the middle of his ass. I raised my arm and let down two more swats immediately. The crack of the belt on his ass echoed loudly in the room. Joe's hands were firmly gripping the mattress and the muscles in his ass and legs were tense but he didn't make a sound. I walked around in front of him so I could see his face.
"Joe, you need to know I'm doing this for your own good and you need to thank me after each swat. Do you understand?"
He took a deep breath. His face was very red. "Thank you." He said. I walked back behind him. "Thank you what?" I asked.
"Thank-" WHACK, WHACK, WHACK. Three fast swats before he could finish.
"Thank you sir." He said through gritted teeth. His ass was now redder than his face. I walked around and picked up the Jokari paddle.
"Are you ready for your punishment to begin Joe?"
"Yes sir." He answered. As I walked around behind him I noticed Sean was completely hard now and was leaking quite a bit of pre-cum. He was tickling his balls and rubbing the shaft. He immediately stopped as I glared at him.
"What the hell do you think you are doing?" I asked. "Do you think we're here to get you off? Joe, do you know your buddy is jacking off over there watching you get your ass paddled? Do you like him beating off looking at your red asshole Joe?"
"No sir." He answered.
"Anything you want to say to him Joe?"
"Knock it off man, you're just making it worse." He was starting to get whiny now.
"Maybe he should take your place since he seems to be enjoying this so much. What do you think Joe?"
"No, come on, please. Can't we just get this over with?" He asked. I could tell by his voice that he was trying to hold back his tears. I rubbed the paddle in a little circle on his right cheek.
"It feels cool against your ass doesn't it Joe. It's going to warm up though. It's going to get very hot. I want to make sure you understand what's going to happen. After each swat you count and then you thank me. If you're not able to count and I go on to the next swat you lose that one, and it will add to the total. If you try to block me you will get a penalty swat added to the end. Do you understand Joe?" I asked.
"Yes sir." WHACK right in the center of his right cheek. Sean jumped at the sound. "One, thank you sir." Joe grunted. Another slow circle with the paddle against his right cheek WHACK right in the center of his left cheek. "Two, thank you sir." He said through gritted teeth. , WHACK. I gave him two on the right cheek quickly. "Three" and there was a pause as he tried to get a breath in. "thank you sir," he said very slowly. Trying to remain steady. I rubbed his ass with my bare hand.
"Good boy. You're being a very brave little man." I said in a soothing voice. I rubbed his ass with my left hand as I raised the paddle with the right. I removed my hand just as the paddle made contact. WHACK. And on it went. We had finished nine and Joe had only missed the third count but his voice was definitely getting strangled. And then the tenth swat, WHACK and there was the unmistakable sound of Joe's first sob and Joe gave in. he was crying hard now.
"Teeennn, Thank you sirr" he sobbed. WHACK "Pleaassse,. No more. I promise I won't do it again. Pleease." WHACK.
"Come on Joe, Don't be a little baby. You can take it like a man." I said as calmly as I could as I rubbed his back and ass. "Sean." I said. Sean jumped, his eyes were wide as he jerked his head from Joe's ass to my face. His cock was rock hard and leaking like a faucet. "Don't you think you should come over and help your friend out?"
Joe was really crying now.
"What should I do?" Sean asked. I gave him a stern look and he quickly added "Sir."
"Come over here and rub his shoulders. Encourage him." I said pointing to the other side of the sawhorse in front of Joe's face. Sean stood up and at least seven inches of hard cock stood out in front of him. He got to Joe and stopped.
"Come on." I said impatiently. "Let your friend know you're here for him." The way Joe was bent over Sean's cock was right in his face. Joe began to bawl harder. Sean reached out and rubbed Joe's shoulders.
"Dude, I'm sorry. You're ok. It's almost over." Sean said and Joe cried even harder. "Come on, he's had enough. He's learned his lesson. Please stop." Sean pleaded looking in my eyes. His cock flexed like crazy as Joe's spit and tears dripped down on it. It was aching to get into Joe's mouth. WHACK.
"Is that true Joe? Have you learned your lesson.?" I asked.
"Yes, please stop. Pleeeease. " He sobbed.
"Sean are you willing to take the remaining fifteen blows Joe is supposed to get?" I asked. Joe reached out and grabbed Sean's Thighs. "Please." Joe whimpered. Sean was trembling. He swallowed hard and he looked at Joe's ass. "Yes Sir." He answered quietly.
"Come around here." I told Sean. He came around to Joe's ass. "Feel that." I told him. "Feel how hot it is. You're willing to take the remaining fifteen blows?" Sean's hand was shaking as he touched Joe's ass. "Yes sir." He answered again. "Undo him." I said. Sean's hands were shaking like crazy as he undid the leather restraints. I went to the cabinet and hung up the paddle and took out an egg timer. I was amazed when Joe stood up to see how hard he was. At least eight inches of hard cock with thick veins running along the sides laid flat against his stomach. His balls were drawn up tight.
"Take a seat Joe." I said indicating the metal chair. Joe's ass barely touched the cold metal seat and he jumped up. "SIT." I commanded and he grimaced as he sat down.
"I'm sorry Sean." Joe cried. Sean began to bend over the sawhorse.
"Not so fast. We're done with that for now" I said. He turned and looked at me with a hopeful look on his face. "Are you a good cocksucker Sean?" I asked.
"What?" He asked.
"Are... You... A... Good... Cocksucker?" I said clearly as I stepped closer to him.
"Uhm, Yes. I think so sir."
"You'd better be." I said. I have ten minutes on this timer and you have ten minutes to thank me for the lesson I've taught you both and for the mercy I've shown. If you don't thank me completely, we'll finish Joe's punishment and then you'll get yours." Sean looked at me blankly. "Go." I said as I started the timer. Sean was on his knees immediately and he ripped open my jeans. The head of my cock was barely out of my underwear and he had swallowed it and sucked the rest of me in. He sucked me for all he was worth as Joe watched in amazement. I tried to hold out but that kid sucked like crazy. He bobbed his head while sucking me with force and licking right under my head. He corkscrewed his head as he bobbed. I've never been sucked by someone who so desperately needed my cum. "Good boy." I said. "If you want to jack off while you suck me you can." He took his cock in his hand and stroked like crazy. He went all the way down to the base of my cock and looked up at me as he sucked back up to the head with everything he had. "You're getting me pretty close but time's running out. I don't know if you're going to make it." I said. "Mmmm, mmmm, mmmm" He moaned around my cock as he sucked harder and faster working his tongue around the head like a madman. He looked into my eyes and I felt his cum splattering against my legs as I began to fill his mouth. The timer went off as I caught my breath. "Clean up this mess." I said and Sean dove down and licked his cum off my legs. I pulled up my pants and left the room.
Joe was late a few more times and knew to immediately go to the basement and wait for Sean to bring me down. I caught them sucking each other off one afternoon when I came home early and had to take care of that but we're still living well together.