Dean had been going out with my older sister, Helen, for about two years when I found out he'd screwed a girl he worked with named Gina. I knew I could use this to my advantage. Dean also worked for my dad, and so if he got found out he'd not only lose his girlfriend, but he'd have to look for another job, too.
I was eighteen and devious. I'd had a huge crush on Dean from the first time Helen had brought him home. He was twenty-two, and had a broad hairless chest and big muscled shoulders. His face was masculine and he was quick with a smile. I loved hanging out with him, and always tried to see him without his shirt on. He came away with us one summer up to the beach house, and I loved seeing him in his shorts and nothing else. He was my fantasy material for most of my whacking off sessions.
I found out he'd screwed Gina because I overheard a telephone conversation between the two. I'd (unintentionally) picked up the phone finding that Dean was using the one in the bedroom. Helen had gone shopping and Dean thought he was home by himself. I heard them talking about how nobody could find out that they'd fucked, and Gina was crying saying she really liked him, but she promised him that she wouldn't say anything. I listened to the whole thing, and wondered how I'd use the information.
So, one Saturday when I knew that Helen was working, I went over to Dean's house. He lived in a small apartment on the other side of town. He was surprised to see me, but invited me in and even gave me a beer. We were sitting on the couch and I could tell he wondered what I was doing there.
"Dean, I've got a deal for you," I told him.
He sat back on the couch with an arrogant smirk on his face. Fuck, he was sexy. I was so hoping that my plan would work.
"What's that, my friend?" he asked casually. He had no idea what I was about to suggest.
"Well, first off, I need to tell you that I know that you fucked Gina Sanderson last month." I paused there to let that sink in.
The color drained from his face and he stared at me. "Shit," he said quietly under his breath a moment later. "How did you find out? Does Helen know?"
"No, Helen doesn't know. I overheard you talking to Gina last month at our house. And I haven't told anyone."
I could tell that Dean's mind was spinning. He didn't know what to do.
"Are you going to tell her?" he asked me.
God, this was great. He was completely at my mercy! "That depends," I said. I wanted his agony to last.
"I want you to fuck me," I told him.
He looked at me with disbelief. "What?" he said, incredulously.
"I want to suck your cock, and then I want you to fuck my ass." I was getting more and more confident.
"Is this some kind of joke?" he asked unsure of my seriousness.
"Nope," I smirked.
"You must be out of your fucking mind!" he said. "I'm not a fag. And I'm not going to fuck you in your… ass. I didn't even know you were into dudes. Jesus Christ Matthew, what are you thinking?"
He was raving. I just let him rant. It didn't worry me. I felt pretty sure he'd agree to my conditions. He was in love with Helen, and probably wanted to marry her. But I didn't care about that. I wanted his cock up my tight hole!
"If you don't do it, then I'll tell Helen what I heard on the phone. She'll dump you, you know… and you'll have to find a new job, too, because dad will fire you for sure," I said, smugly.
"You fucking shit!" He sat back down heavily on the couch.
"Dean. I only want you to do this once. And I promise I'll never ask again, and I will never say anything to Helen about Gina."
He didn't say anything, but lay back on the couch with his hands over his face. He was thinking. I sat across from him, staring at the bulge in his pants. God, he was cute.
My heart leapt. Holy shit! He was considering it.
"Yup, just once; I want to suck your cock, and then I want you to fuck me."
He was silent for several moments and then said, "And you won't ever tell anyone, right?"
"Nope. If you do it, no one will ever hear about you and Gina from me."
"Yeah, but I meant about this?" he said.
"Of course not, never."
He looked at me for a long time. "You're a fucking asshole, Matthew," he finally said. "I thought you were a decent guy, but today you've shown me what a little cunt you really are."
"Well, I guess you are entitled to your opinion… so what's your answer?"
"Yeah… I'll do it, only because I really love your sister and don't want to lose her. But I will never have anything to do with you again after this, you god damn blackmailing little faggot."
I didn't care. All I heard were the words "I'll do it". My cock nearly burst out of my pants.
He was still sitting on the couch, so I told him to stand up and take his pants off. He did, somewhat slowly and reluctantly. He was going commando, and his heavy cock flopped over his balls and he just stood there wearing only a t-shirt. Shit, I couldn't believe I was about to get my mouth around that. I knelt on the floor in front of him. He stood proudly, not looking down at me.
I didn't want to rush it. I knew I was being an asshole, but I meant what I said to him. I only wanted it once and I would keep my promise about not saying anything. So because it was going to be a one-off, I wanted to make it the best I possibly could.
I held his heavy cock in the palm of my hand. His body tensed at the touch of my male hand. His cock was fat and wrinkled. I lifted it up so I could see his balls and he crinkled his face up and groaned - more a groan of disgust than arousal. His balls were hairy and hung really low. I loved that his cock wasn't hard. That way I could fit the whole thing in my mouth and feel it grow.
I licked his balls. I felt him clench his ass. I knew he wasn't happy, but I didn't care. I had dreamed about sucking his dick for years. I nuzzled my face into his groin and licked the line between his torso and his legs. My face was up against his nut-sack and I pushed his limp cock up onto my cheek. I felt it growing a bit.
Because he wasn't hard yet I could fit the whole thing in my mouth easily. It squashed up against the back of my throat. I sucked it like a teat, and used my tongue to massage the underside of his shaft. That worked. I could feel it get bigger and swell. I knew that when it was hard I wouldn't be able to fit it all in my mouth. I had to let some of it out, but I kept sucking and covering it with saliva. He just got bigger and bigger.
I took the whole thing out and kept pumping the shaft. It was dripping with my spit and I played with the end of it with my finger. This whole time Dean was just standing still. He didn't say a word and he didn't touch me. His hands were by his sides and he wasn't giving me any encouragement at all.
"Well, even if you're not liking it, your cock sure is," I said, hoping he'd loosen up.
"Go fuck yourself," he said. The hate in his voice kind of scared me, but I was in too deep to stop. The damage was already done, so I figured I may as well enjoy it.
"No need, when I have you to do it for me," I said. Dean just snarled.
My own cock was throbbing hard in my pants, so I took a second to take my jeans and underwear off. It felt a lot better now that my cock was free. I knew I couldn't jerk myself because I would cum quickly, as turned on as I was.
I went back to work on Dean's big cock. It was much bigger than mine. I'd say it was about eight inches long and pretty fat. I really liked how it was covered with veins, and there was a thick cord which ran along the underside of the shaft from his balls up to the head of his dick. My tongue ran up and down the huge rod, covering it with spit. I loved licking his balls. When my tongue flicked underneath his balls Dean moved his legs apart a bit (probably just instinct and unintentional) to give me easier access to the part right under him, between his legs. The smell under there was amazing – musky and sweaty. I stayed under his ball sack for ages, licking and smelling him, and I could tell he was liking it.
While my tongue was working his balls I was jacking his cock. It was lubed up with my spit and I didn't want his hard-on to go down.
I thought it was about time to get his cock up my ass. I was a bit nervous actually, because I thought it might hurt. The only other guy to fuck me was my friend's cousin, Kevin. He lived over the back from us, and every now and then when he was horny he'd come over and fuck me. But I'd had other things up my ass. My favorite was to get a big fat carrot, cover it with a condom and then slip it in and out of my hole while I jerked my cock. So I knew my hole could take something as big as Dean. But that was when I was in control. I knew Dean wouldn't go slow with me. I'd just have to see how it went.
I'd come prepared. I reached over to my jeans and pulled the tube of KY out of the pocket. Keeping my mouth over the knob of his cock, I squirted a gob of gel onto my finger and lubed my tight little hole. I even pushed a KY-covered finger up inside me. With my asshole ready I took my mouth off his dick.
He looked down at me. He'd lost the hatred in his eyes and it was more a look of resignation.
"Where do you want me to fuck you?" he asked.
"Lie on your back on the floor. I'll sit on you," I replied, figuring that would give me control over his large member going in me.
He lay down and grabbed a cushion from the couch for his head. I took another look at him. My heart did a flip as I couldn't believe that I was about to sit on his dick. Even if he did hate me for the rest of my life, right at that moment I didn't care. All I wanted was to be fucked by him. I didn't care about the consequences.
His cock was still hard and pointing up at his face. I picked it up and sucked it one last time. Then I squeezed some KY onto it. When it was slippery I climbed over his body and straddled him with my ass aimed directly at his cock.
"I don't want you to push up to me," I told him. "I'm going to lower myself onto you."
He didn't reply.
The big head of his cock was pushed against my hole and I sat down further. It was stretching my ring, but I was so horny for him it didn't hurt. I pushed a little bit harder and it broke through my sphincter. He was about a third of the way in, and I stopped so my body could get used to him.
I knew that it must have felt great on Dean's cock, even if he wasn't into guys. A hot, tight asshole wrapped around anyone's cock is a fantastic feeling. Dean had his head back on the pillow and shut his eyes. I ran my fingers over his body and pinched one of his hard little nipples, making him jump.
After a bit I knew I was ready for all of him. In one smooth movement I sat right down on him, taking his entire thick shaft up my tight hole. This time he let out a small groan. Yes, I thought. You're enjoying this! I sat on his pelvis and used my ass muscles to squeeze his dick. He groaned again.
I wasn't moving up and down yet, just contracting the muscles, giving his cock a massage. He still wasn't looking at me, but I knew he had to be enjoying it. He was moving beneath me, every now and then pushing into me as if he wanted to be deeper inside.
Slowly I started to pull my ass up off his cock. I could feel it slipping out of me. I leaned forward so that only the head of his cock was still in me. And then just as slowly, I sat back down. God! I thought I would cum. My hands were on his muscled shoulders.
"Fuck, that feels so good Dean," I told him. Still, he didn't respond to me.
He opened his eyes and looked at me.
"I want you to fuck me, and do it hard. Please," I begged. "Fuck me like you fuck Helen, and like you fucked Gina. Come on, fuck me hard."
Something changed in his face. I could see him smile a little bit, like he knew he was good at this. Without taking his cock out of my ass, he rolled me over onto my back. So now my legs were up over his shoulder and he was hovering above me. I braced my hands on his biceps. His arms were muscled like the rest of him, and as I lay on the floor with my legs over my head I knew I was going to get the ride of my life.
Dean's cock was moving inside me. He was slowly bringing it out and then moving it back in again. It was too much for me. My own cock was so stiff it was almost painful. Every time Dean thrust forward into me, my dick moved on my stomach. I found the KY and squeezed some on my dick to give it lube. It got really slippery being rubbed back and forth.
Suddenly the pace changed. Dean started pounding my ass hard. I cried out in lust. I couldn't help it. Every time he banged his hard cock up my tight chute I let out a loud grunt and gasp. He put his hand over my mouth, without losing rhythm. I pulled my head sideways and started licking and sucking his hand. He put his fingers in my mouth and I sucked them like I'd sucked his cock. I think he liked that because he kept changed fingers.
While he was fucking me I was using my ass muscles to squeeze his dick. His balls were slapping against my butt. He was getting faster and I thought he was about to cum. My balls tightened and the tip of my cock got hard. I knew I was about to shoot.
"Oh, fuck, I'm gonna cum," I said, and about two seconds later a big rope of white cum came flying out of my cock and shot over my chest, landing on my face and in my hair. The second spurt landed on my chest and the third on my stomach.
Dean never stopped pumping while I was shooting my load and I knew he was close. He suddenly stopped pounding me and rammed his cock as far as he could into my body. He froze and let out a grunt. His whole body spasmed and I felt his cock swell as his first spurt of cum filled me. He must have jerked about five times as I felt my ass being filled with his hot load.
He pulled his cock out of my ass slowly. He was panting loudly, and his t-shirt was covered with sweat. He sat back, resting his ass on his heels a little bit away from me, breathing deeply, looking at his half-hard cock. It was covered with juice and there was a bead of cum sitting on the piss slit. He squeezed his cock which made the cum-drop grow. Then he scraped it off his cock-head with his finger and wiped it on my leg.
I was still lying on the floor, and knowing all his cum was inside my ass made me so horny I wanted him to fuck me again. But that was out of the question. Dean got up off the floor and stood over me.
"I'm going for a shower. When I've finished, you'd better be gone you little faggot."
"Don't forget what I know Dean. I told you I wouldn't tell anyone, and I'll keep my promise. But you'd better be nice to me, or who knows what might happen." I was trying to sound cocky, but really I was scared shitless. I didn't know how he'd treat me now. I was almost regretting what I'd done.
Dean went for a shower and I got dressed and left. Some of his cum dripped out of my hole into my underwear. I used those undies for years when I jacked off. The memory of Dean fucking my ass is still the hottest thing I can think of when I'm trying to cum.
Dean and Helen ended up getting married. He and I never talked about what happened, and I kept my promise and never told anyone what I knew. Dean treated me with absolute indifference and never spoke to me unless he absolutely had to.
Sometimes I think perhaps I shouldn't have done what I did. But mostly I remember it as the best fuck I've ever had!
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