Red, Hot Ass

Mrs. Brockett, my babysitter had done it to me when I was twelve and had misbehaved. She had made me pull my pants down, bend over her big knees, and had spanked me. She had spanked me hard!
She had told my parents what I had done, and they approved of her punishment even though I complained that a babysitter should not be able to touch me!
But secretly, that night, alone in my room I jerked off thinking of her hand hitting my rubbery ass. Mrs. Brockett had no idea what genie she had let out of the bottle for as she had spanked me, I had hardened. As she had spanked me, I had imagined her fingers going where I fingered myself, where I pushed things up inside me. And then I had imagined she was a man, a man who would do what I desperately wanted.
My secret life was just that, secret. I would spank myself, I had made several paddles for this purpose. I dated, but not seriously. I went to college, got laid by a woman, but it all seemed so much less than what I really needed. I have never gotten very tall, 5′6″ and was very slim. Being small was not a benefit in college.
When I graduated, I got a job at an advertising firm. I was 22 and acted as their gopher. I knew I was beginning at the bottom, but there was a chance for me to be promoted, learn the business. The head guy was a big, tough looking man in his early fifties. He looked strong, his hair was partially gray. He was nice to me, or so it seemed, but the stories of his temper ran through the office every day, so I was scared of him.
He called me into his office, I had never been in it before. It was a big, wide open office. He was on the phone and indicated I should wait. I looked around and immediately I saw two big paddles. Both had Greek letters on them, and I realized they must be paddles from when this man was in college, fraternity paddles. I began to harden, just at the sight of them.
“Those were the days,” he had come up behind me. “See those?” I nodded. “Well, if you were a pledge for our fraternity, those got laid against your ass and I mean hard. Hell, in front of the whole damned fraternity, and you better not make a noise except to say, “Thank you, Sir. May I have another.” He stopped, laughed, “and I can tell you, they were always willing to ‘give you another.’”
“It’s Jason, right?” I nodded. “Okay, look, I need some help, understand?” I nodded again. “I need you to attend a party with my wife tonight. I can’t go.” I had no idea what to say. “Oh, don’t worry. It’s not black tie or anything. It’s a very casual fundraiser. All you really need to do is driver her there, and just hang around. Can you do it?”
I nodded. “Good,” and with that he gave me the details. As I was leaving he stopped me. “Were you in a frat at college?” I shook my head. He sighed, “too bad. Was a great time, can tell you that.”
And then his phone rang.
The party was fine, it all worked out. His wife was in her late 40’s, pretty, but old. She had big, fake tits that she showed off, though her legs and ass were very fine. But all I could think of was her husband, with a paddle in his hand spanking my naked ass.
He called me in the next day, right at 5:00. “Everything go okay?” I nodded. “Well, my wife didn’t think so.” He glared at me. “In fact, she told me you tried to feel her tits, is that true?” I denied it, but it was clear he didn’t believe me. “She said you tried to grope her at the party, and in the car. Now, what the hell is that all about?”
I had no idea what to say. He had stood, come over to me. He was huge, big, threatening. “Look,” he said menacingly, you had better tell me the truth or your ass is out of this place, understand?” I denied it again, but he was having none of it. He grabbed my arm, and I was scared as hell. I felt like peeing I was so scared.
“Look, you little shit. You have two choices right now. One, I fire your punk ass.” He stopped, and I begged him not to. I really did need the job. “Or two, those paddles get used on your punk ass.”
For a moment I had no idea what he was talking about, but then he had one of the paddles in his hand. “Understand?” And I did. And I almost fainted. Not from fear, oh no, but from desire. My face got flushed, and I felt faint. My knees went rubbery. I know I almost fell, but he caught me. And in the same motion he yanked my pants down, I was wearing no underwear. “Ah, you like to go natural, eh?”
I was still standing, he was holding me up. I wriggled, he thought I was trying to tear away, and WHAP, he hit my ass. I yelped, I couldn’t help myself. He laughed, and WHAP, he hit me again. He forced me over his couch, my naked ass sticking in the air, and he went at me. He hit me five more times, hard as hell. Then he stopped. I turned around. He was standing about three feet from me, looking at my, what I am sure, was bright red ass.
“Okay, you’ve had your punishment. No more of that shit, okay?” I said nothing. I just stood and turned around. I was bone hard. He stared at my cock. I had very little, almost no hair on my crotch. My testicles were drawn up against the base of my shaft. My penis was not big, on the small side actually, probably 5 inches or so.
“You didn’t try to fondle my wife’s tits, did you?” He said with dawning understanding. I shook my head. “She lied, didn’t she?” I nodded. He seemed at a loss for words, his anger had gone.
“But,” he began, then stopped, then started again, “but you didn’t mind the paddle, did you.” I shook my head.
He opened his pants and pulled them halfway down. His cock was fat, dark, and circumsized. The head was purple and big. He was soft. He had a big, thick bush of dark hair. His balls were big, and hung down. They also were covered with hair.
I didn’t know what to say. I turned around again and bent over the couch. When the paddle hit me, I whimpered, and then it hit me again, and again. Then I felt his blunt, thick fingers probing me, they were slick with spit, I assumed. Then one pushed into me, then another. I stayed still, I made no sound. They pulled out of me, and I knew what was coming. I had waited all my life for it to happen, and now it was happening. His hand smacked my burning ass once, then again, and again. Then I felt the bulbous, hot tip of his prick at my hairless fuckhole. It was slick, I don’t know if it was spit or precum.
He pushed forward, I pushed out, and he entered me, all the way in one movement. I grunted, but held still. And then he fucked me. I ground back against him, and as he fucked me he spanked me, hard.
And I began to cum, cum from his spear up me, and from his hard, calloused hand hitting me. I shot off all over the back of the couch. Once the hard jets finished, I just kept cumming, cum drooling thickly from my little prick.
“You fucking little queer,” he said and moved faster, harder. I could tell he was near. And then he rammed his full length up me. I could feel his cock expand, I knew he was shooting off, and then it pulsed. I was so sensitive it was almost too much to bear. He held his pose, hard into me.
Finally, his hard body, which was against my back relaxed. He pulled off me, and out of me. I clenched, I knew I was full.
Before he could even move, I turned and dropped to my knees and took his half hard dick into my mouth. He laughed as I sucked on him. His hands rested on the top of my thick hair. He didn’t harden, but I didn’t care. I had a cock in my mouth. Finally he pushed me away.
He pulled his pants and undershorts up. “Get dressed.” I did as I was told.
He went behind his desk. “No one, understand?” I nodded. “Tomorrow, at 5:00, right here.”
I nodded, and finally spoke, “thank you.”
He smiled, “No, thank you! Now get that hot, red ass out of my office.”