Based on the shocking number of page views for almost all of the Drawn To You posts, MHD readers love some imagination-based dicks.  And I can’t agree more with what good taste you guys have. As I’ve said before, Handjobs magazine gave me some of the best illustration porn of my teenage life, and their stories were beyond compare. Now, I know not everybody is into the father/son incest vibe, so I’m gonna steer clear of that for Story Time. But I still want to share some of the incredibly sexy tales that accompanied some of the best erotic gay illustrations of the 90s and 2000s. Welcome to Story Time!

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Mr. Aiken’s Bad Boys
story by Allen and illustrations by Roger

From Handjobs Magazine, November 2001

 

It had been a long time since I had gotten in trouble at school. I was usually a pretty good kid. I think that’s why Mr. Herrin, my P.E. teacher, had it in for me. I had managed to stay out of trouble in his class until one day near the end of senior year. A group of my friends had all decided to cut the last class of the day and go hang out at the lake. I cut Mr. Herrin’s class. I didn’t really think anything about it. It was just P.E.

When I showed up in class the next day he was waiting for me. I had just changed into my gym clothes when he told me to report to the principal’s office. I gave him a confused looked and he said,

“That’s what happens when you cut class.”

“Aw, man!’ I said as I trudged down the hall to Mr. Aiken’s office.

I had to wait outside for what seemed like an hour before he opened the door and said, “All right, Allen. You can come in now.” I sat across the desk from him. As he took a seat in his big, leather chair, he said, “I don’t recall you ever having been sent to my office before, Allen. What happened.”

“Coach Herrin is just sore because I cut his class. He’s had it in for me since the beginning of the school year.”

“Well, you know, you’re not supposed to cut classes, Allen.”

“It was just P.E.”

“I realize that P.E. may not seem as important to you as your other,
more academic, classes,” Mr. Aiken said, “but you have to realize that we have rules here. And when you break the rules, there are consequences.”

“I guess so,” I said sullenly.

“Well, Allen, I’ll give you the same choice that I give everyone who gets caught skipping classes. You can either have one week’s detention or three swats.”

I didn’t have to think about it long. The three swats would be over with and forgotten long before a week’s detention would be up. “I’ll take the swats,” I said.

“Very well. Stand up, drop your gym shorts and bend over the desk.”

My face turned bright red. “Uh … Mr. Aiken, I’m not wearing anything under my shorts except my jock.”

“Well then, I guess that’ll help you remember not to cut class, won’t it?” he replied.
I stood up and dropped my shorts. When I bent over the desk a weird feeling came over me. I could feel my cock starting to get hard in my jock. That just made me blush more. What if Mr. Aiken noticed?

“Spread you legs a bit more, Allen,” the principal said. “I think it’ll be easier if you kick your shorts off.”
I did as he told me and spread my legs wide. When I felt the cool air on my hole, my cock surged in my jock pouch again.

Mr. Aiken pulled out an enormous paddle. It almost looked like and oar. He rubbed it around on my asscheeks and then came down hard with the first swat. The pain and heat spread over my upturned ass – and my cock jumped again in my jock. The principal rubbed my butt with the paddle again and then slammed me with the second swat. The swats really hurt, but for some reason they were turning me on.

I was waiting for the third one, but instead, Mr. Aiken said, “Stand up, Allen.”

I couldn’t stand up. He’d see I was hard! “I … I can’t,” I said.

“I couldn’t have hurt you that badly. What’s the problem.”

“I … I have a … boner,” I mumbled.

“That’s nothing to be ashamed about, Allen. Obviously, you’re enjoying your punishment. I am too. See?”
I slowly stood up and turned around. Mr. Aiken had unbuttoned his shirt and opened his pants. The fattest, longest cock I had ever seen was sticking out of his fly.

“See, son,” he said. “Having a hardon in the principal’s office is nothing to be ashamed of. Why don’t you get rid of that jock?”

He pulled my jockstrap off and reminded me that I had one more swat coming. He bent me over again and pounded my butt one more time. Then held me down and rubbed his cock over my burning asscheeks.

“You have a beautiful butt, Allen. It might be a little sore right now, but you seem to be dripping a fair amount of precum.”

I looked down. He was right. My cock was leaking all over his office floor. I had really gotten turned on by the spanking. The principal continued to run his hands all over my asscheeks. Before I knew what was happening, I felt the end of one of his fingers against my hole. I started to say something in protest, but then I realized that I was enjoying it too much. It hit me like a ton of bricks: I wanted my principal to play with my butt hole; I liked it!

“You’re not the first boy to end up in my office that enjoyed a good, hard spanking,” he said as he inserted his finger all the way into my hole. “Luke Raymond enjoyed my discipline so much that he moved in with me after graduation.”

I remembered Luke. He had been a senior when I was a freshman. I had always thought he was hot. I imagined him being spanked by Mr. Aiken as he continued to fuck his finger in and out of my butt. Suddenly, he crooked his finger up inside of me. He hit a place up my hole that made me give out a gasp and shoot a huge load of cum against the side of his desk.

“Hmmm … you seem to have spunked my desk, son. I think that’s going to call for some more punishment. Unfortunately, the school day is almost over.” He picked up a pen and scrawled something on a piece of paper. “You should report to me at this address tonight at eight o’clock. Don’t be late.”

“Yes, sir,” I said. I got the feeling he liked being called “sir”.

“Get dressed and then you can go, Allen. I’ll see you later, son,” he said with emphasis.

 

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Around seven-thirty, I told my parents that I was going to the library to work on a paper. Something told me that it wouldn’t be a good idea to tell them that Mr. Aiken wanted to see me at his house after school. When I rang the doorbell, Luke answered. He peeked around the open door and said, “Oh, it’s you. You’re right on time, and it’s a good thing. Dad wouldn’t like it if you were late.”

I stepped inside and said, “Dad?”

“That’s what I call Mr. A. now,” Luke explained. He was only wearing a t-shirt. His uncut cock hung between his legs like a thick sausage. It swung from side to side as he walked. “You should strip right here in the hall. Then we’ll go upstairs.”

After I had taken all my clothes off, I followed him to an upstairs bedroom. Mr. Aiken was waiting there for us completely naked.

“Allen,” he said, “glad to see you could make it. I want you to bend over and show Luke your butt. Then we’ll deal with punishing you for your lack of self-control this afternoon.”

Luke had flopped down on the bed. I stood opposite him and bent over. When I looked back at him that fat pole of his was standing up almost straight between his legs. The glistening head had poked its way out of his foreskin.

“What do you think, Luke?” Mr. Aiken said. “Should we give this boy another round with the paddle, or should we just fuck him?”

“Both,” Luke answered. “You swat him and I’ll fuck him.”

“I think you both could probably use a good spanking. Why don’t you join him. I want to see both of those butts up in the air.”

Luke got off the bed, pulled off his t-shirt and bent over next to me. Mr. Aiken pulled out a paddle that was a twin to the one he had at school. He wacked both of our asses good with it. I envied Luke’s hairy ass. All that fur had to act as somewhat of a cushion. By the time it was over my smooth, hairless butt felt tingly and hot. Then Mr. Aiken told us both to get on the bed. “Have you ever been fucked in the ass before, Allen?” he asked me.

“Uh … well, you had your finger up there earlier,” I answered.

They both kind of laughed and Mr. Aiken said, “I’m sure you’ll find out soon enough that it’s not quite the same thing. Why don’t you show him, Luke?” Luke pulled my left leg up, spreading my bright red butt cheeks and exposing my hole.

He began to finger me like Mr. Aiken had earlier in his office. But he didn’t stop with just one finger. He slipped a second one inside next to the first. Then he pulled them out and worked a thumb up there. Finally he pushed three fingers into me.

“Uhhhn,” I grunted as he stretched my hole open.

Luke looked back over his shoulder and said, “What do you think, Dad. Is he ready? Should I give him the real thing?”

“Work it in easy, son. We might want to use his butt again later.”

I felt the wet head of Luke’s cock prod against my hole. He pushed forward. It felt really big, like he was trying to put a doorknob up my hole. I winced. “Just relax, son,” Mr. Aiken said. “Take a deep breath.”

I did like he said and felt Luke’s cockhead pop inside. The shaft of his cock slowly eased up my chute. It felt great.
Then Luke’s cockhead grazed that same spot Mr. Aiken had found earlier. I knew I was going to cum. I made a grab for my cock, but before I could touch it, it erupted all over my chest and belly.

Luke looked back at Mr. Aiken and grunted out, “Dad … he’s bringin’ me off. I gotta … gotta … CUM!”

A stern looked crossed Mr. Aiken’s face. “Well, I see you two are going to require more punishment. Cumming so quickly, like that; not giving me the opportunity to join in. You both are very bad boys.”

Somehow, I got the feeling I was going to enjoy being a bad boy for Mr. Aiken.

 

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Oh for the days when you could get spanked in a jockstrap in the principal’s office, right? Woof.

 

– tyler