Starting Over Pt. 02

A few months after moving in with Tyler, my life had changed completely: I was no longer trapped in a marriage I didn't like and a job I could barely stand. I was getting back in shape -- and I was looking the best I'd ever looked in my life. And to top it all off, Tyler and I had jerked off together.

At first, we didn't repeat our masturbation session. We'd still work out, we'd shower and get changed -- all the while sporting chubs and halfies, but I think we both felt that we'd gone a little too far or something. Neither of us made another move, and I was actually okay with that. I had just ended a long relationship, and I liked my friend as a friend -- I didn't want to screw anything up.

But sometimes I'd wake up at night, and my dick would be painfully, enormously hard. My underwear would be stretched tight, my dick's movements testing the tension of its elastic band. I'd put my hand in my underwear and run my hands along my shaft.

I would think about going into the living room. My buddy would be sleeping on the couch, his huge, muscled body spilling off it. His blanket would cover some of his lower half, but his fat pecs and gigantic biceps would be clearly visible. That marbled chest would slowly rise up and down.

I'd take off my underwear off and lie on the couch next to Tyler. I'd sidle up against his hard, warm body. I'd run my hands along his sides, feeling the solid ripples of his virtually fat-free torso. I'd grab his dick, and after a few pulls, it would turn from thick and floppy to hard, warm steel. Then I'd hold our dicks together. As I looked into his eyes, I'd feel him pulse as I pulsed. His mouth would open in desire. Then, and only then, would I pull his face closer, pull him in for a kiss.

As soon as our lips touched, the fantasy would end, and I'd be back in Brady's bed, cumming all over my hand.

As the days wore on, I thought that I would have to make a move. That is, until Brady showed up.

*****

Yeah, that's right. One day, Tyler's twenty-year-old son Brady showed up at the house when I was the only person there.

"Hey, is anyone home?" I heard someone ask. I had been getting some snacks from the kitchen, and so came out holding a banana.

A tall young man was standing in the front hallway carrying a giant gym bag. He was wearing a tank top and long board shorts. He had a swimmer's build -- broad shoulders, powerful legs, and a very narrow waist.

"I'm here," I said. "I'm your father's friend, Joe."

"Dad told me about you!" He said. He reached out his hand. It was big, with long fingers. "Nice to meet you, Uncle Joe!"

I reached out my right to shake his hand and realized I was still holding the banana. "Sorry," I said, and quickly switched it to the left hand.

Brady laughed. "Don't worry -- I won't grab your banana!"

His joke embarrassed me. I tried not to look at his face as his fingers gripped around mine. His hand was bigger than mine, and also somewhat playful -- he squeezed me.

"I've heard you've been staying in my room," Brady said, putting down his gym bag.

"Oh yeah," I said. "I hope it's okay."

"Totally," Brady said. "My Dad told me how close you are as friends."

Brady moved into the kitchen, went to the refrigerator, and began pulling food out of it. It looked like he was getting fixings for a sandwich.

"We've known each other for a long time!" I said.

"It's cool," Brady said. "But you are going to get a bedmate for the next little while. I'm still working near college, but my girlfriend wants to hang out with me more, and she lives down here. I'm annoyed she can't come see me, but I guess she makes the rules."

While I listened to him, I watched him put together the sandwich. His arm muscles were taut but impressive, and they visibly tightened and loosened as he slapped the fixings together. His eyes were bright and mischievous. He had that hair cut that so many young guys had these days -- sort of a bushy mushroom. And he had dimples in his otherwise very square cheeks.

I realized that I was finding Brady attractive. My dick began to stir in my pants. As I was wearing grey track pants with no underwear -- I hadn't expected anyone to come home -- I had to move somewhere to hide it.

"Shit - should I find another place to stay?" I said, sitting down at the table.

"No, no, it's cool. It's a king bed. I've had two or three guys from my volleyball team crash in the bed with me, and it's so big we almost don't even notice if anyone else is there."

Brady licked some mayo off a thumb. As he continued making his sandwich, a nipple peeked out of his tank top. My dick grew.

I could just imagine it now: I'd get behind him. I'd slam him against the counter. I'd push his shorts down, and my fat cock would plunge into his virgin asshole. He'd wriggle as I entered him. I'd make him beg for mercy. But he'd love it, the dirty slut.

It was good that I was sitting down and the kitchen table was over my lap because now my dick was standing at full attention. It pulled the grey sweatshirt material into an awkward tent. I could feel my breathing change, and my eyelids sank over my eyes.

Brady came over to the table with his finished sandwich. It was gigantic, and mustard and mayo were glooping out of the sides. He began eating it while talking to me about his life, his girlfriend, his job. I couldn't pay attention to any of it, except by watching him hungrily devour this gigantic sandwich. It was almost too much. I don't know where this sudden arousal had come from, but I needed to let loose. I could feel pre-cum starting to spew out of my dick.

Fortunately, while he was talking, his phone rang. It was one of his friends on FaceTime. He picked up the phone. He began laughing and saying, bro this and bro that. While he was distracted, I shuffled off to the bedroom. Over the sink in Brady's bathroom, I jerked for about thirty seconds. The cum absolutely flooded out of me.

What the hell was happening?

A few months ago, I had never thought about having sexual contact with a guy, and now I was thinking about it all of the time, and with two different guys -- a father and a son! I could kind of understand it with Tyler -- we had been friends for years. But with Brady, it seemed thoroughly random. I couldn't understand it.

But I had also not been this happy for ages. For the last ten years of marriage, my wife and I had barely had sex. I was starved for some dick in hole action. I had felt so bad about my looks and my relationship that my sex drive had dwindled to the point that I hadn't even masturbated that often. I definitely wasn't getting random boners. And I definitely wasn't filled with sexy fantasies.

My life now, with all of this new sexual interest, was strange. But while I didn't know what was going on, it felt amazing.

And Brady was right -- sleeping in the king-sized bed wasn't an issue. That night, we both slept in our underwear -- we oddly enough had very similar tiny white briefs -- but we were never even remotely close to each other. The only real problem was that when I woke at night with my erection fighting to escape my underwear, I wasn't thinking of going into the living room to be with Tyler. Instead, I was looking over at the sleeping Brady -- at his gentle, slack face and his sleek, toned body, and most importantly, the bare tip of his erect dick pushing out from the waistband of his underwear. I was thinking of him, instead.

What the hell was I going to do?

Before I could make a decision, things got weirder.

*****

Tyler got busy at work. He started missing our workout sessions, and he sometimes missed dinner. He'd come home late, and crash on the couch, exhausted. Some days, I had dinner with just Brady and his mom, Sharon, which was very weird. She still didn't like me.

Brady, on the other hand, seemed to really like me. He'd tell me stories about his life and all of the dumb shit that him and his friends would get into. During the day, if he wasn't working, we'd hang out in the backyard, listening to his music. After my initial horned up moment, I could usually contain myself when we were hanging out, even when he usually didn't wear a top.

But at night, things were getting strange.

I usually slept on the side of the bed nearest the bathroom. I had chosen that side because it was the side I always slept on. When Brady started sleeping in the bed with me, he slept on the other side. He told me that my side was normally his side of the bed, but he was flexible -- it didn't matter to him.

And it worked for us until one evening he got home drunk.

I didn't notice when he got into bed. I had gone to bed early. He must have come in while I was sleeping. But at one point, I woke up. It took me a moment or two, and then I noticed I was spooning someone -- my body cradled theirs, and my arm was reaching across them and hugging them across their chest.

A moment longer, and I realized that it wasn't my ex that I was cradling -- it was Brady.

Brady was out cold. He was snoring loudly in that way that drunk people do.

That's also when I noticed that Brady was naked. He wasn't wearing anything. I was wearing underwear, but my erection was very noticeable. And because of the way Brady was sleeping, my erection was resting against his meaty, round ass checks.

I felt my heart race. How did this happen? Did I get drunk? Why was I in this position? Could Brady feel my erection? If I moved suddenly, would he wake up and accuse me of attacking him?

I paused. I listened to his breathing in the otherwise silent room.

Another part of me was very turned on. My dick was resting against his ass. I'd been starved for dick in hole contact for years. In particular, I hadn't been able to fuck an ass in a long time - my ex-wife had never been into ass play. But I loved it. I missed it.

And now, I could feel the sweaty heat of his buttocks on my dick. It sent shivers of pleasure through me.

I tried to control my breathing.

I wanted to rub my cock along those cheeks.

I wanted to reach down and feel if he, too, was erect.

I wanted to just bring my dick a little lower and test his asshole.

Just let a dollop of pre-cum drip into his asshole.

I let these thoughts roll around in my head. The delicious euphoria coursed through my body.

But I couldn't. I was worried about what could happen. I was staying with my best friend, and I didn't want to ruin it.

But I also couldn't tear myself away.

I felt Brady's chest expand and relax. I felt the warmth of his back. His foot was a little entangled with mine. And best of all, I could feel his ass cheeks on either side of my dick.

Right then, he coughed. He smacked his lips. He stopped snoring.

My heart stopped.

I just waited. My heart began to thunder in my chest. I waited.

There was no movement from him or sound.

Was he awake?

I didn't know what to do, but I felt I had to stop this.

As carefully as I could, I unravelled myself from Brady. I shimmied over to the middle of the bed.

I lay on the mattress. My dick was throbbing painfully with desire. My heart beat like I'd just finished a sprint. I waited to fall asleep again.

But I was also somehow waiting for Brady to wake up and for him to grab my dick.

Eventually, I fell asleep.

*****

Some barrier seemed to have broken that night, because in the morning, I awoke to Brady's voice.

"Oh sorry, Uncle Joe," Brady said. "I'm all up in your business."

I was on my back in the middle of the bed, and his arm was flung across my chest. His erect dick was touching my leg. He did not rush to move it, but he withdrew his arm.

"It's okay, Brady," I said. "I hadn't noticed."

He slid out of bed and stood up. His erection waggled.

"My morning wood has been nuts lately," he said. "Is it this bad for you?"

I looked at his long, smooth dick with a beautiful red head. It wobbled as he shook it side to side.

"Sure, even us old guys get boners too," I said.

"Shit," Brady said. "Sorry I was rubbing it all over your leg. I got drunk last night, and I guess I just tried to get into my usual side of the bed."

"It's okay Brady," I said. "These things happen. I'm taking up space in your bed."

"No, no," Brady said. "It's cool." He started pulling at his dick a bit. "I'm going to yank it in the bathroom. If you want to jerk out here, that's cool."

That morning, while listening to him masturbate in the bathroom, I came myself and wiped my cum on one of his dirty pairs of underwear.

*****

Later that day, I was hanging out in the backyard. The backyard was small. It was fenced in all sides. There were a few trees on the far end, but it was mostly empty except for some lawn furniture under a patio umbrella near the sliding glass back door.

I laid on a lounger in a pair of tight shorts I'd bought recently to show off the gains on my legs. I didn't have a shirt on. The summer sun beat down. I was getting steamy from the heat.

Meanwhile, Brady was inside the house. He was talking to his mother. I overheard him defending me.

"I think it's weird that this guy is still here," Sharon said.

"Oh you don't like him because he's Dad's friend," Brady said. "He pays to live here, doesn't he?"

"He started paying something because I complained," Sharon said. "And why does he have to sleep in your bed. A grown man in your bed? That's odd."

I felt embarrassed to hear them talk about me. I had probably overstayed my welcome. But I also liked living here.

"Chill out Mom," Brady said. "I'm happy to have him in my bed."

That comment sent a tingle through my head.

"Besides," he said. "I don't stay there that often."

He was right: several days a week, Brady stayed at his girlfriend's house. Sometimes, late at night, it was just me and Sharon in the house. At those times, we tried to avoid each other as much as possible.

Brady came back outside carrying a few bottles of beer. He was wearing his regular long board shorts with no shirt. His body had an athlete's natural perfection: everything was tight and toned and his skin was smooth and flawless.

"I got you another beer," he said. "My Mom is such a tool sometimes."

"What's wrong?" I said, taking the bottle.

"Oh nothing." He opened his beer bottle and sucked back half of it in a big gulp.

For a few minutes, we sat in the sunshine, listening to his music on a little speaker he'd brought out. Because I was lying on a lounger next to him, I couldn't really see him. Occasionally, I'd hear the sound of a swig of a bottle.

"Uncle Joe," he said. "Can I ask you something?"

I could feel the sun and the beer having a slight buzzy effect on me. I was feeling relaxed and chill.

"Sure," I said.

"Why did you and your wife break up?"

I laughed. My buzz died a little.

"What? Why do you want to know?"

"I'm having some problems with my girlfriend."

"Well," I said. "Me and Annie were just not meant to be together -- we were a bad match from the start. And we kept it going because we thought we should. I don't think it's anything like you."

"Maybe it is," he said. He took a swig.

"You're just going through regular stuff," I said. "I remember being your age. You fight about everything."

"Yeah, maybe," he said.

He was silent again except for the occasional swig.

"Did you have any sex problems?" he asked.

My dick twitched in my shorts.

"We didn't have sex for years," I said. "If that's what you mean."

I paused.

"Is that what you mean?"

He was silent. I took off my sunglasses and looked over at him. He pulled at the silver chain around his neck and put it in his mouth.

"Our sex is great," he said, lowering his voice a bit. "I love fucking her, and she's a great lay. She does everything, BJs, hand-jobs, and she's got a nice tight little pussy. She always makes this little high-pitched moaning sound when I'm fucking her good."

The blood was moving toward my dick. I could feel pleasure radiate through the whole area of my crotch.

"But?" I said. It was hot out and sweat had pearled on my stomach. I rubbed my hand across it.

"But," he said. "She won't do some of the things I ask."

He looked at me. There was a glint in his eye, and his dimples appeared even though he wasn't smiling. I had a feeling I knew what he was going to say, but I also felt like we had to go through the whole charade.

"What won't she do for you?"

I could feel my dick slowly growing, the fabric of my shorts subtly moving as it grew. I wasn't wearing baggy board shorts like Brady, so if I kept chubbing out, he'd eventually notice. But unlike last time, I decided not to hide it. I felt like this was part of it, too.

"You know," he said. "Butt stuff." He covered his mouth to hide his grin.

I ran my hand over my pec and squeezed it.

"She won't let you fuck her in the butt?" I said. I knew it wasn't what he meant, but I wanted to get him to say exactly what he meant.

He rolled his eyes and ran his hand through his hair.

"No, no," he said. "I want her to play with my butt."

He laughed and ran his hand over his bicep.

"Have you ever done that before, Uncle Joe?"

My dick was pretty stiff at this point -- I'm sure it was noticeable. But he never looked at it -- he only looked at my eyes.

"I can't say I have. Have you?"

"Yeah," he said. Laughing again. "Yeah."

My dick was spewing pre-cum. I wasn't looking, but I could feel a wet patch on my shorts developing.

"What's it like, Brady?"

Once again, he rolled his eyes, and pushed his hand through his floppy hair.

"Why don't I show you?"

Before I could say anything, he stood up and pulled his shorts down. His solid dick popped out, standing straight.

He sat himself back down on the chair with his large, tanned leg propped up on the wicker table next to him.

"Can you see?" he said.

I could see. From this angle, I could see his beautiful erect cock. He had pubic hair above his dick, but his balls and visible asshole were hair free.

He licked a finger and inserted it into his asshole. The puckered opening gently withdrew for him and then hugged him tight.

He began pushing it in and out of his hole while tugging on his dick.

The laughing, funny guy from before had become serious. His eyes got squinty, and his mouth opened a little. He was working his finger in and out of his hole like he was impatiently tapping a button.

My dick's thumping movements in my shorts were creating an audible sound from the fabric moving. The precum was gushing.

Before long, he had switched to two fingers. He began to push them in and out. The sphincter smoothly slid opened and closed around his fingers. It seemed to be sucking on them.

I would have liked to have him suck my fingers.

After a minute of neither of us talking, and the only sounds being him pulling his dick, he finally spoke.

"Let's see it."

He nodded at me.

Without breaking my eye contact with him, I wrestled my dick out of shorts. It snagged a little as I was getting it out, and that made him take a deep breath in.

"It's so fucking huge," he said. "That's a monster."

"It is," I said. "Nine inches. Yours is pretty big, too." And it was true, it took some time for his hand to run up and down the length of his shaft. He did it in this smooth practiced motion. He had fucking totally figured out the perfect way to jack that dick off.

"No, no," Brady said. He took his fingers out and spat on three of them and put them back in. He was slamming them in and out. "Yours is so fucking big. It's bigger than I thought. It looks bigger than it was in your underwear."

I was pulling at my dick too. Brady's Mom could come out at any moment, and here I was jacking off with her son on her deck furniture, in the middle of the day.

"I felt that monster last night," he said.

"You felt my dick last night?" I said. My pace speeded up. Pleasure was coursing through my brain. Pinpricks of joy rushed all over my face.