Chapter 2: Guys and Guys

Zack and Derek’s dad.

Maybe a month after Derek went to college, we swapped sex pics every day and masturbated together on the phone; Derek’s dad asked me over to help with cleaning their gutters.

It was a hot day. Me in loose shorts with a jock under and a tank top. Derek’s dad, built like him, six-foot and thin, blond and blue, a really good-looking guy also in loose shorts but no shirt. I’ve known him all my life, but now, after Derek and I have been fucking, he looked different. I need to think of other things.

“Thanks for coming over, Zack. I have to clean the gutters, and there’s one corner that’s tough to reach. I’ll need you as safety guy.”

“Yeah, sure, Mr. C, no problem.”

Jack, Derek’s dad, went up the ladder, I steadied it on the ground. As he went up, I could see up the leg of his shorts. He had nothing on. I watched his ass, a little hairy, flex, and if he took a big step, I saw his hole and the tip of his cock. I’d never thought of him that way, but now my horizons were broader, and I found this older guy attractive. I was getting hard and looked away. I’ve become such a perv.

Jack had to lean off the ladder to reach the gutter. He stopped.

“Hey, Zack. I’m not feeling safe this way. Can you come up and steady me?”

As I climbed the ladder, Jack’s butt was on display up the leg of his shorts. My erection was hidden by my jock, so I just enjoyed the view. Jack has a nice round ass, and when he moved, I saw his sack and the tip of his cock.

I was a few rungs under Jack. My head at his knees, enjoying the view. I put my hands on his calves, enjoying the firm muscles and warm skin.

“Higher, Zack, please.”

I’m like, sure, Jack, I’d love to. Now my hands are on the back of his thighs, at the bottom of his shorts.

“Yeah, that should be good. Hold on.”

I gripped his thighs as he leaned over. I felt the muscles flex under my fingers. My cock was rigid. He messed around, and the ladder squeaked as it shifted. Jack looked over his shoulder. “Higher up, Zack, I almost slipped there.”

Now my hands were shaking. This was definitely not casual. This man was coming on to me. I moved my hands up until I felt the bottom of his round ass. My thumbs were in his crease and almost on his hole. I was panting.

“Oh yeah, that’s better. Just hold there.”

With pleasure. I thought and pictured myself masturbating later to all this. I’d never done anything like this with Derek’s dad. He stopped reaching.

“Shit, can’t reach. Zack, your arms are longer. Mind if we change places, and you can try?”

“Sure, Mr. C.”

As I climbed down the ladder, Jack turned and looked down. “You’re an adult now, Zack. Call me Jack.”

As Jack got off the ladder, he made no attempt to hide that he was totally erect and tenting his shorts. He took a long look at the fat bulge in my shorts. It’s going to be an interesting afternoon.

I climbed up the ladder, my jock-restrained cock rubbing the rungs. At the top, I waited as Jack moved up behind me. His head was even with my ass. I leaned off the ladder and felt his hands on my legs.

He didn’t even hesitate. I felt his strong hands glide right up the back of my legs, under the hem of my shorts. His hands clenched my ass.

“There, I got you now. See if you can reach.”

I could and worked at cleaning the leaves, and junk out as Jack’s hands explored my ass. I felt his thumbs caressing my hole. I was so turned on I was shaking. I made the job last as long as possible, then leaned back. Jack slowly took his hands away.

“Thanks, Zack, that was great.”

“I’m glad I could help, Jack. Thanks for steadying me.”

Jack blushed. “It was my pleasure.”

Mine, too, even more so. I thought.

On the ground. Jack tenting his shorts, and my cock sticking up almost out of the waistband of my shorts. We both knew what was going on. I grabbed the rope for the ladder to lower it.

“Leave that for now, Zack; let’s hit the pool.”

“Thanks, Jack, but I didn’t bring a suit.”

Jack walked to the big inground pool and shoved off his shorts with his back to me. “Kerry won’t be home till five. It’s just us guys, come on.”

Jack dove in. I stood at the pool’s edge, waiting for him to surface. He popped up, looking at me.

“You sure this is ok, Jack?”

“Oh yeah, go ahead.”

I flipped off my tank top and ran my hands over my hairless chest. “Man, I’m sweaty. I’m gonna mess up your pool water.”

Jack’s hand was below the water. I could see him holding his cock. “Don’t worry about it, Zack. Come on in.”

I turned around and shoved my shorts down, bending over to do it. I heard him gasp as he saw my ass and my nice little hole framed by the straps of my jock. I tossed the shorts on a lounge and turned around.

“I’ve never done this,” I said.

Jack was gently stroking his cock, trying to be subtle. I slipped my fingers under the elastic of my jockstrap. “Here goes.”

The head of my cock was already over the waistband. As I slid the jock down, I exposed more. Jack was nearly drooling, fighting to be cool. I stepped out of it, giving Jack a good view, and dove in, surfacing next to him and, on the way, seeing his hand on his erection.

“This is different. Feels good with nothing on.”

Jack kept a little distance, his hand off his cock. “I love it. I’m naked in here all the time.”

I laughed, “Even when Mrs. C, Jane, and Dereck are here?”

He laughed. “Well, Kerry, but not all of us.”

We stood in the water for a minute, listening to the birds. Jack moved in front of me, took a deep breath. “I saw you and Derek the other day.”

So that was it. That’s what brought this on. I had to be sure. I laughed. “Jack, you see us all the time.”

He moved closer. I felt the tip of his erection touch mine. “No, Zack, I saw you two naked in bed, Derek’s hand holding your erect cock.”

The feeling of Jack’s cock tip touching mine was electric. He was going slowly, so I followed. “I’m sorry, Jack. Derek and I were wrestling one day, and it kinda turned into experimenting.”

Jack put his hand on my shoulder, laughed. “Don’t be sorry, Zack. It’s very normal. Lots of guys experiment. Was that a one-off?”

“No, we’ve done stuff a few times. We like it, it’s fun. Does it mean we’re gay?”

Jack massaged my shoulder; it felt good. “Not a bit. When I was your age, public views said that. But in reality, no. Lots of people enjoy sex with men and women. You’re lucky. These days it’s not such a big deal.”

I shifted my hips, flicking the tip of Jack’s cock with mine. “I’m not sure the guys on the swim team would agree.”

Jack pressed in, his arms around my waist. Now our cocks were vertical between our bodies. He looked into my eyes. “I’ll bet at least half of them have had a cock in their mouths and some up their ass.”

“Really?”

Jack’s arms were around me, so I put mine around him. “Zack, I was on the swim team. I’ll tell the story another time, but I found out when I caught two guys sucking cock in the locker room.”

“Wow. Did you_?”

“Not with them, but when I told my best friend, he was like, you didn’t know? We didn’t think you were into it.”