Starting Over Pt. 02

"I felt it at my asshole," he said. "I felt it between my cheeks. I was thinking about how I wanted it inside me."

He moved to putting all of his fingers into his ass. The wicker table began crinkling under the repetitive jerking of his body. He stopped stroking his dick and thwacked it against his abs. Then he went back to furiously pulling at it.

"Do you want that?" Brady said. He was squinting so much, I couldn't see his eyes. His face was contorted into something resembling pain.

"Do I want what?"

"To fuck my hole?"

"I want to fuck that hole."

"I want you to fuck it."

"How bad do you want my hole?" He said this in a high-pitched way.

I was so close to cumming. My balls tingled, overflowing with dick juice. My dick's sensitivity was so high it almost hurt.

"I want to fuck you up."

We stared into each other's eyes. Just one more moment, just one more thing would push us over the edge.

He pulled his hand away from his asshole. For a moment, the hole gaped open. I thought about my huge fucking dick plunging into him. I thought about destroying that virgin hole.

"Yessssssssss," I said.

My shoulders shook. Waves of excitement exploded through my whole torso. Mile after mile of cum flew out of me. I stared straight ahead, but I couldn't see anything anymore. All I could feel was the sticky cum pumping out like a hose, soaking my pecs.

When my eyes refocused, Brady had his fingers back in his hole and his head was thrown back. He tensed. He looked down at his dick as if mystified what was happening. His dick jerked and white flecks of cum sprayed directly up -- like three or four feet -- and landed on his face, in his mouth, in his hair. It even landed on the umbrella standing above him. His body jerked some more, his abs neatly flexing in and out. Some of the cum landed on the skin of his abs, and it disappeared and reappeared as the skin flexed around his abs.

He looked at his dick as if in pain until the shuddering stopped.

"Holy shit," he said. "Fuck."

We paused to look around at the mess we'd made.

"I agree," I said.

When our panting died down, all we could hear was his music on the little speaker. I had completely forgotten it was playing.

*****

We got cleaned up -- there were some party napkins left out on the patio table -- and we made our way inside. Sharon wasn't around.

I didn't know how to talk about what had just happened. It was amazing, I wanted to do more, but I also didn't know what or how we could. How do you talk to your best friend's son about that great jerk off session?

But before I could say anything he said, "Oh shit, my girlfriend called." He walked off into the other room to talk to her.

I tried to act nonchalant. I grabbed a glass of water and went back outside. I laid back down on the lounger. I scrolled through my phone. But as I stared at the screen, trying to take in the dumb videos I was watching, I was really only waiting for him to return.

Eventually, I heard him slide the door open and come out. The hairs on the back and sides of my head started tingling.

"This sucks," he said. "But I got to go spend the night at my girl's place. She feels I'm neglecting her."

"You better go then."

"Yeah," he said. That devilish grin again. "But I'd rather spend time with you, Uncle Joe."

"Yeah, I'd like that, Brady."

"I'll see you in a few days, Uncle Joe."

"We'll see each other then."

And he pulled his shorts down, showed off his dick -- already erect again -- and put it back.

"Can't wait." He laughed.

*****

The rest of the day I spent wondering what the hell I was going to do. I was fooling around with both my best friend and his son. In some part of my brain, it felt weird. But in another part of my brain, I felt good. I liked fooling around with them. I hadn't felt this sexual in years! I didn't want it to end. In fact -- I wanted to go further.

With Tyler, there seemed to be a problem. Tyler seemed to be avoiding me: he was always working late, and we were never at the gym at the same time.

With Brady, things seemed to be moving more smoothly. But did that mean I should do something with him? Brady was a consenting adult but fooling around with him felt wrong -- like breaking a promise somehow. Isn't secretly jerking off with your best friend's son kind of wrong?

Even if it was, I felt like an addict. Just picturing Brady's fingers going in and out of his asshole was enough to make my dick grow hard, and for my face to flush.

I went for a walk after dinner to try to clear my mind. I walked through the nearby park and enjoyed the setting sun. People were out walking their dogs or enjoying the last sunshine of the day. And the walk helped me. It did reset things for me. I realized, when it came down to it, I liked living in Tyler's house. Just that fact suggested that I shouldn't do anything more with Brady. I just didn't want to jeopardize my living situation.

Once I had decided that, I felt clarity. I wasn't an addict. It was just a bad decision I had made. After all, I wasn't gay. I was straight. It felt good to think these words. And while I made these decisions, I realized I could think about Brady and not get aroused. By the time I came back to the house after my walk, it was as if my crush on Brady had dissipated.

I went upstairs to Brady's bedroom and started to get ready for bed. I had a quick shower to clean my sweat off and I brushed my teeth.

I normally wore underwear to bed. But it didn't matter tonight -- Brady wasn't coming home. Instead, I laid out naked, feeling clear about how I was not going to do anything further with him.

*****

When I woke up that night, I heard him first.

Brady was snoring again. Gently this time.

I looked over at his body. He was lying with his back facing me. He was naked. I was naked.

Why was he here? Did he have another fight with his girlfriend?

In the moonlight, his back was long and lithe, and his ass was slim but plump.

If I was going to follow my new rule, all I had to do was just ignore him and go back to sleep.

It made a lot of sense. And I tried to do that for a few minutes.

But as I lay there, I could only feel my excitement bubbling within me.

I remembered what he'd said earlier in the day.

He wanted my dick inside him. And with the way my dick was beginning to chub out, I clearly wanted to put my dick inside him, too.

I was an addict, and I wanted this drug. Just once more.

I slid over to him and spooned him. I put my arm over his torso and lined up my crotch with his butt. And then I laid there.

My heart beat wildly, but he kept breathing evenly in and out. He was taller than me, so I looked at his smooth, triangular back. I breathed on it.

My dick, like a balloon inflating, flopped over. It grew and grew. I felt it grow. I waited for a sign from him.

It expanded until the head was knocking on his asshole. Just gently rubbing against it.

For a moment, nothing happened.

I briefly panicked. Did I somehow imagine what he'd said earlier? Maybe he didn't want me anymore.

The room -- the house -- was silent.

And then, he wriggled his butt.

I listened to his breathing. It was even and deep. I couldn't tell if he was sleeping or not. I pushed my dick's flaring head against him again.

A moment passed. I breathed into his back. My whole attention focused on my cock and its gentle contact with his opening. I shivered with excitement.

He wriggled again.

I touched my dick against his opening again.

This time, he whispered, "Put it in."

My hand squeezed his pec.

"Use the lube," he whispered. "On the nightstand."

I grabbed the lube from the nightstand and quickly greased up my pole.

My heart slamming in my mouth, I brought my dick to his hole again. This time, I pushed in more insistently. I put my hand on his hip.

This time, like his fingers before, I felt his sphincter giving way. But my dick was big. He may have played with his asshole before, but he was obviously new to this. I could feel the resistance building.

My head slid mostly made it in. But my shaft was very wide, particularly at the top.

"Oh Uncle Joe," he whispered. "I can't believe it."

I stopped pushing for a moment.

"Do you want this huge dick?"

"Yes," he whispered. "I really do."

I was pushing gently, but we weren't moving. His virgin asshole was still keeping me out.

"Then prove it to me, you little slut. Open up for me."

"I'm trying."

"You can do it. Believe me that I'm the one in control. I'm going to own your fucking dirty hole."

I put my hands on either sides of his hips and pushed more insistently again.

His asshole released slightly, and my dick slid a little more in.

I could feel that he was trembling. He really wanted me, but he couldn't get his asshole to agree.

"Do you really want me to fuck you?"

"I do."

"Then say it."

"I want you to fuck me."

His sphincter was slowly giving up. It relaxed a little more. I slid in further.

"Say, 'Fuck my dirty hole Uncle Joe.'"

"Fuck my dirty hole Uncle Joe!"

"Say, 'I'm a worthless little whore.'"

"I'm a worthless little whore. I want your dick so bad, Daddyyyyyy."

And as he said that last word, his asshole gave way. It was like a dam slowly collapsing. It opened slightly and then tore open. His resistance melted and he slid over the thickest part.

"Gugghhhhhhh," he said.

He rapidly slid all the way down my shaft until he was resting in my lap.

"Oh this feels so good, you little faggot."

I slid both of my arms around his torso and grabbed his pecs. I squeezed them.

He let out a little mew.

His fucktube felt like thick velvet against my overexcited dick.

I could feel his heartbeat in his asshole. His pulse was rapid, and mine was slower. But slowly we began to sync our heartbeats.

And slowly, I began to withdraw my cock from his ass.

"Unhhhhhh," he said.

I pulled it out over the thick part. I could feel his body quiver when I did that. He let out an exhalation of air. And then I pulled it all the way out.

He sighed loudly.

"Do you want me to put it back?"

"Yes, oh yes!" He wriggled his ass again.

And before he even finished talking, I was sliding it back in. This time I could feel himself pushing his sweet ass on to me. I bottomed out again.

"I'm going to take my fucking time. I'm going to fucking ruin your ass."

Slowly I began pistoning in and out, each time feeling less and less resistance. My face was mostly on his sweaty back, sliding against it. My legs slammed into his buttocks.

"Good," I said. "You're learning to fucking ride this dick."

When I felt him starting to slam against my dick, I slid out.

I quickly stood up. He looked up at me, wondering what was happening. I dragged his legs off the bed. I flipped him onto his chest.

"Face down!"

I pushed his shoulders into the bed.

"Push your ass up."

He pushed his buttocks upwards. Even in the moonlight, I could see them clearly. His ass cheeks were round and athletic, and they separated nicely to show off his hole.

I put more lube on my dick and then fed it back into him. I was kind of amazed at how his ass could fucking eat it all -- my cock is as thick as a beer bottle.

Now I could take my time. I grabbed his narrow waist. I fucked him slowly, and then rapidly, and then slowly again. He kept moaning in time with my thrusts. I just fucking loved fucking him and turning him into my little faggot. I owned his ass.

"You just love my dick, don't you, you little bitch?"

"I love it Dadddddyyyy. I love your fucking huge dick!"

My dick was in fucking charge. It felt so good -- better than it had felt in years. It was doing its job.

I looked down at his long, smooth back, and his narrow waist. I got another charge of excitement. This perfect young stud wanted me to turn him into a fucking hole. Every time he moaned that high-pitched moan, I felt a rush.

"You want me to fuck you all the time, right?"

"I want it all the time!"

I pulled my dick out. His asshole kept its craggy hole open for a moment. Pre-cum was dripping from my cock, and I painted it on his butt cheeks and then into his hole again.

I was the fucking king. I was turning a straight stud who'd just been fucking his girlfriend into my own little faggot. My huge dick was that good.

I pulled it out again.

I slapped one butt cheek and then then other one with my dick. I ran it up and down his crack. All the while, Brady was pushing his ass into me.

"Do you want Daddy's load?"

"I want you to cum in me!"

"Yeah, I want to give you my dumptruck load you little fag."

"Fucking dump it in me!"

Sweat was pouring off me. I pulled out again. I flipped Brady onto his back. His face was a look of confusion. His body looked flawless and taut, and his hard, throbbing dick had squeezed out a trail of pre-cum that stuck to his abs. I was so ready to cum that I thought about just cumming into his face. But I really wanted to drop my load in his hole.

I lifted his legs up and rested them against my chest. Then I slid my cock back into him. He mewled again.

"Give me that hot load!"

Gripping his waist tightly, I slammed him against my dick. I kept impaling him, over and over. A few minutes ago, his hole wouldn't let my dick in, and now it was sliding in and out with ease. Each time I sank all the way in, I could see his whole body jolt with pleasure.

I leaned forward, folding his legs backward. His legs squeezed against my face. My thrusts became faster and harder. I could feel my dick was on the edge. It was itching to release.

"Daddy is going to give you his load!"

I leaned right in, squashing his legs and dick between our chests. I gave him a kiss on the mouth.

Just as I did, he moaned into my mouth. Suddenly his dick began pumping. His asshole pulsed around my cock.

My cock detonated. It felt like a grenade going off.

"FUCCCCCKKKK," I said. The lights exploding in my brain felt magical. My whole body spasmed. I couldn't see or think.

My cock controlled my whole body. It seemed to pump for a solid minute. As it did, I could feel his cock shooting. The cum filled the gap between our two bodies. All the way through, it was pure pleasure.

Eventually, both of our dicks quieted down. My cock deflated somewhat. I withdrew it out of his asshole, trailing cum. We were sticky and panting.

I laid down on the bed next to him.

"That was awesome," he said.

"I'm glad you liked it," I said. "I thought it was pretty amazing, too."

Our panting slowed down.

"Can we do this every night?" Brady said.

I turned to him. He was showing me his dimples.

"Every night?" I said. "You're going to kill me!"

He laughed.

We lay there for a few minutes. I was in pure bliss. I couldn't think of anything to say. I hadn't been this happy in years. I felt big and charged. A real man.

I was just about to suggest we get a shower when I heard a quiet knock on the door.

Brady and I looked at each other, confused.

"Hello?" Brady said.

"Hello," Tyler said. "It's Dad. I was wondering if you were okay."

"Yeah, yeah, I'm fine," Brady said. "Why were you worrying?"

"I just heard something," Tyler said. "Can I come in?"

I jumped up and scurried over to the washroom.

"No, don't come in, Dad!" Brady said. He pulled the comforter around himself. "I'm naked."

There was silence.

It felt like Tyler was trying to make a decision. Finally, he spoke.

"Okay," he said. "I'm going back to bed."

Brady and I looked at each other.

(To be continued.)