The Boss Boy

Remember to donate to Nifty to keep this site going. https://donate.nifty.org/

Feel free to message me, too. Feedback in general, or just to talk.

The boss's boy ==============

I looked over my shoulder as yet another trucker passed by. He hammered the door on his way in, got on the urinal between me and my partner, took his piss and got out, seemingly unfazed by my casual jerk off. "Lunch time isn't as busy," I said as I finished peeing and shook the last droplets off. "We're wasting our time here."

My partner hopped two urinals over and continued his piss beside me. "It's just not busy at all, that's what's strange," he answered. "I've been here before a number of times, it's always been a great cruising spot. So weird," he continued as his hand glided over his soft dick while his stream kept going down. He cupped my balls and let my dick lean on his fingers as I continued pissing. "So what got you so pent-up these days?"

"It's that boy," I answered as I kept on drinking from my beer can. "He's always watching us work from the other side of the pool or from the house. With those eyes, you know."

He let my cock slide over the palm of his hand and began stroking it. I looked over the shoulder once more to make sure there was no one in the stalls behind us as I crossed arms with him and reached for his cock, too. Soft, though fluffed up a fair bit, his was still such a sight to behold. "Yeah, man, I know. Those fucking doe-eyes locked onto us all day."

"And he ain't watching us for momma, no no, he's-"

"Yeah, he has the hots for us," he cut me off. "I saw he was circling around the pool just so he could get a better angle at you peeing."

I laughed. "Hell yeah! And I made a real nice show for him, whipping it out nice and good."

He grinned. "You're lucky his mom didn't catch you. You weren't being very discreet, if I were to give my opinion. Taking your shirt off while we work, these little pissing shows of yours..."

I reached further down his dick and let the tip of my fingers guide his hot stream, gently caressing the head under its generous skin. "Like you weren't doing it too."

We smiled as we kept gently stroking each other out for a few more seconds. Someone came in and pissed at the urinal near the door while we looked down at our dicks. No harsh movements, but we weren't being subtle either. The burly, bearded dude went out without ever looking at us. "TSK," my friend let out, frustrated.

"So Freddie," I broke the silence.

"What is it, man?"

"Would you do him?"

"What?" He asked as his hanging balls twitched.

"You heard me."

Took me a while, but I finally felt his cock grow on my hand. "I don't know, man, I don't think so. I wouldn't risk going back to prison," he answered. "Never again."

I nodded at him. "He's cute, though."

"So cute!" He agreed in a whisper. "You know how old he is? Like, maybe ten? No more than that, I bet," he continued in a normal tone.

"Beats me," I answered, shrugging. "Like young enough to not produce cum, I would say."

We both nodded in unison.

"But what if you were dead sure you wouldn't get caught?" I kept on pressing. I pulled his cock to point upwards as he finished pissing, so I could more easily slide my hand over his fully hard cock, easily over twice as long as the palm of my hand and thicker at the base.

He bought his time thinking about the answer. I finished my beer and held onto the empty can as I twitched my cock to let the last stubborn droplets of piss fall down. Freddie made it difficult for them to fall in the urinal, however, as he masturbated me nice and hard with a firm grip.

"I don't know, man. I mean, he obviously doesn't look like he has the room to take me."

I nodded at him.

"And I wouldn't enjoy waiting around too much," he continued.

"It would be some handfuls for him," I added smiling as I tapped at his dick with my thumb.

"You know what's up," he continued. "But who knows, maybe he's just this cute flexible boy who can go down on any cock."

"Ever met one of those?"

"No," he answered right away. "Never been with boys."

"Oh," I said, and we both laughed.

"Marco, look," he begun saying as he pulled his dick off my hand and awkwardly shoved it back inside his pants. "I know how much you perv on the boy, but don't go for it. Risks are too great, man."

"I know, I know," I answer, disappointed we ended up not getting the fat trucker dicks we were looking for.

"Go find a boy elsewhere, an easier one."

"Yeah, I-"

"One that isn't the son of some douchey rich madam."

"Freddie, I know."

"I bet you do," he said as he put his hand over my neck and pulled my body towards his with open arms. He hugged me with my hard cock pressing against his belly. "Come by my house later, we can play FIFA together and I can suck you off, how does that sound?"

"Your lady won't be home?" I asked as I tucked my cock in and pulled my pants up.

"Oh, she will. But when has that ever stopped us?" He answered, winking. "Speaking of her, I gotta pick her up at her work," he continued as he walked through the door and kept it open for me. "I can give you a ride home before that."

"Ah, sorry man," I said as I walked out and protected my eyes from the sunlight right above us. "I need to go back to the Richards. I found some extra work tomorrow, tiling the walls of a bathroom, and I need my tools."

His motorcycle was at the last spot in the parking lot at the front of the gas station. He walked towards it and I followed him. "Man, you're working on Sundays now too? I don't want to see you in your lazy, tired ass next Monday, we have a lot of work on the guest house, me and you," he cautioned me as he hopped on.

"Yeah, I hear you, but I need the coin."

"Suit yourself," he finished as he revved the engine up. "Wanna hop on, and I drop you there?"

"Come on, it's just a couple of blocks away, I'll walk."

"See you later then," Freddie said as he maneuvered the motorcycle towards the street. "And good luck. The Richards are usually out on Saturday afternoons."

I shrugged. "I'll try my hand anyway."

We both waved each other goodbye and I went on my way as I once again adjusted my boner in my pants. "Fucking waste of time," I muttered to myself as I walked to the other side of the street and looked back at the gas station. "Place was much better a year ago."

I wiped the sweat off my forehead with the sleeve of my shirt as I buzzed in, hopeful Freddie would be wrong. I got an urgent job and was able to negotiate double my usual hourly rate, and the extra coin would go straight to replacing my joysticks, both sadly at the end of their lives.

No one came through, so I buzzed it in again. My shirt was glued to my chest, which is just usual at that time of day in summer. I turned around and was about to give up when I heard the sound of the line being picked up on the other side. "Hello?"

I grinned. That girly, smooth voice could've had anyone mistaking him for a girl. "Hayden, boyo! How are you doing?" We never had the boy let us in, it's usually his mom or the uncle who comes by sporadically. "It's Marco, the mason. Would you do me a favor and call your mom?"

"She's sleeping."

"Oh, okay. Could you... wake her up?"

I stood waiting in silence for a couple of seconds. "She said she was tired."

"Oh, hmm..." I answered. "Well, I just need to come in, pick up my tools and be on my way then. Think you could let me in?"

And as soon as I stopped talking, I heard the front gate being unlocked. "Thanks, boyo," I said to him, but he had turned it off.

As I walked in, my dick started swelling faster than my brain could imagine things. I shifted my boner to the side to be a bit more discreet as I went past the front porch and took the pathway on the side towards the swimming pool. I saw Hayden's silhouette through the blinds of the window, leaning on the hallway inside the house, then I hear him race towards the kitchen on the back to meet me. "Hi!"

"Hi!" I said. Hayden was resting on his elbows by the kitchen window, wearing a dotted shirt and what I think were his pajama bottoms. "Freddie told me you weren't going to be home."

"Yeah... I'm kinda grounded," he said as he leaned his head on the window's bars and then lifted his head up again. "So mom said I would stay home for the weekend."

"Damn, boyo, I'm so sorry!" I said. "Well, I'll be right back, let me just go get my tools, okay?"

"Okay, mister!"

Freddie's words were flying around in my head as I walked past the pool and entered the guest house we're in charge of building. As I put my backpack down and packed my tools, my dick was aching for a release. Hayden's always being watched one way or another. {Don't do it,} his words echoed again, but I willfully decided to ignore it as I pulled down my shorts, took off my briefs, tossed them aside and then wore my shorts again. {It's now or never,} I said to myself as I made sure the tent raised by my cock looked nice. {Your loss,} I then told to imaginary Freddie as I put my backpack on and went back to meet the boy.

My cock began to throb as I saw Hayden following it intently with his gaze as I walked around the pool. To be fair, I did add a little of flair to my gait. Wanted my junk to flop around as much as possible. He leaned in and shoved his face in between the bars of the window as I came close. "Done! It's all here," I said as I tapped the backpack strap. "Thanks for letting me in, Hayden."

"Aww," Hayden sighed. "Okay then, mister."

I turned my side to him, so he could get another glance at my crotch and began walking out, then stopped and turned back to him. "Hey, Hayden. It's hot today and I'm a bit thirsty," I said as I fanned my shirt. "Think you can give me some cold milk and cookies like you always bring us while we work?"

"Of course!" He replied, joyful. As he went further into the kitchen, I leaned in and tried to peek at his body. Perked up, bubbly butt, certainly pillow-y. The pajama bottoms were a bit too loose, but I think I could see a cute lil' boner gently poking at the fabric, too.

"If only the bars weren't here," I muttered to myself.

Hayden took some time rummaging through the pantry. As I waited, I decided to give my cock some stern squeezes. It ached too much, and my pre-cum had begun to leave a ring on my shorts. I paid no mind to it, of course. Let the boy look.

"Sorry, mi, I couldn't find the cookies, but here's your milk," he said as he carefully handed over a glass full of cold milk between the bars.

I covered his hands with mine and gently stroked them as I took the glass. "Thank you, Hayden." My cock twitched as I witnessed the boy get chills on the peach fur of his forearm.

"I think mom might be hiding them from me," he added. "She said I'm eating too much and I'm getting fat."

"No! You? Nonsense. You look great, boyo."

"Aww, I dunno," he answered, blushed. "But thanks, mister."

I winked at him. "Anytime, boss." I drank my milk in one go, letting some spill over my beard, dribbling towards my chin and then shirt. "Here, thanks again," I said as I handed back to him the empty glass while I raised my shirt to wipe off my face, exposing to him much of my round, firm and hairy belly.

"O-of course," he said as the glass almost slipped from his hands while he gazed upon my body, tracing a path starting from my belly and zigzagging towards my bushy crotch and then right to the stretched fabric of my shorts.

"Careful now!" I said as I caught the glass and made sure he held it safely. "So why are you always watching us work?"

"You noticed me?"

"Almost every day," I said casually as I put down my shirt. "You also watch me when I take my pee breaks," I add as I tweak the waist of my shorts, making my cock to swing around, motion that was beautifully tracked by the boy's eyes. "Is your mom putting you on watch duty?"

Hayden shook his head. "No. I guess I... I like watching you work. I like how you look."

He shrugged. "Dunno. I like how your shirt often sticks to you when it's hot, and how you take it off sometimes and wipe yourself off with it. And..."

"Come on, tell me."

"I guess I like how you smell when you pass by as you say goodbye," he admitted. "Is that weird?"

"Not at all!" I assured him, laughing. "Some of us men like each other that way. Me and Freddie. You, too. It's perfectly normal."

He smiled at me. As his pink lips parted and he began to breathe out a word, I continued. "Say, boyo," I said as I came closer to the window and raised my shirt again. "Do you want to touch me?"

Hayden took no time to take on my offer. He first squeezed my nipples, letting the metal of its piercings slide through his fingers. Then he pulled his hand away and spread my sweat over his fingers, seemingly measuring my belly all around. Finally he let my chest hair flows through his fingers as he massaged me. Boy couldn't blink, such pure was his bliss.

I carefully pulled him closer to the window and pulled his other arm through the bars. "Touch me all over, come on, don't be afraid."

"Y-yes, mister," he said. "Thank you, mister."

His hands went straight to my nipples once more. "Don't worry, they're sturdy," I assured him. Hayden fiddled with the round piercings, passing his finger through them, pressing against the tips of my nipples until he felt the resistance of the metal underneath, then pinched them and witnessed me moan at him. "Ooh, that's good," I spoke, softly.

"I always wanted to touch them," he admitted with a smile from ear to ear. "Ever since I first saw them."

"And is it living up to your expectations?"

"Thousand times!" He exclaimed.

"And how about this?" I asked as I took one hand and pressed it against my cock under the shorts. "Ever wanted to touch my cock?"

Hayden giggled joyfully. "I-I can't wrap my hand around it very well."

"It's because your hands are still small, see?" I explained as I hold his other hand, and we compared palm to palm. "With the two you should be able to hug my cock, no problem."

"I hope so," he said, still giggling.

"Say, Hayden, can I touch you too?"

"Of course," he answered as he kept squeezing my cock while his other hand began to comb my chest hair.

"Can you open the kitchen door? The front door, maybe?"

He sighed. "I'm sorry, I can't. I wish I could. Mom's keeping the keys and I can't enter her room."

"She doesn't have a heavy sleep?"

"Dunno, but the keys are in her pocket. Don't think I can take them out without her noticing."

"Well, that sucks," I joked. "So how about you bring that chair over here and step on it, so I can touch you?"

"Oh! That might work!" He answered enthusiastically. "Wait here."

"Not going anywhere," I told him as I watched him do what I ordered.

Hayden placed the chair right against the wall and then jumped on top of it. I could now see the bottom of his pajamas without looking inside and down. "Take off your shirt," I told him.

As he got shirtless, my cock began throbbing rhythmically as I admired his cute, smooth body. Hayden was a bit like me when I was his age, not exactly chubby but not a slender kid either. And I do remember I used to occasionally get compliments about my butt from my great-uncle. "Beautiful," I told him.

"You think so?" He asked, striking a pose.

I laughed. "Absolutely!" I leaned over and rested my shoulders against the bars. "Say, Hayden, what we're doing here should be a thing just between you and me. Can you promise to keep a secret just between us?"

"I'm not telling mom!"

"And anyone else. Deal?"

The boy spared no second to think it over. "Deal!"

With that done then I reached for the waistband of his pajamas and pulled it down in one swift motion, letting his stiff cocklet spring up, hard as a rock with its head still timid under the skin. "Wow," he said, then stood silent as he felt my hands measure him up. I squeezed his meaty, soft thighs and massaged him down to his calves, then back inside with one hand in his inner side to gently caress his hairless balls and perineum while my other hand squeezed one butt cheek. Hayden held onto the bars with his eyes closed, trying to keep himself steady and moaning softly as I touched him.

"So cute," I whispered. Right there, as I stroke his little cock and noticed its head was still a bit too shy while I groped his butt, I had decided to explore all the boy's holes myself. That I would be His man. "Come closer," I ordered him. "Step on here and let your knee pass through the bars," I said as I gave two light taps on top of the window frame. "I'll hold you by the hip."

Hayden diligently did as I ordered, his crotch coming closer and closer to my face. Once his belly touched the bars, I dove straight towards his cock. "Oh, umm," he muttered as I let my tongue slide around it, wrapped my lips around it and swallowed it as deep as it could reach. "That's so g-g-good," he let out as he moaned. I kept on squeezing his butt with both hands, kneading them and playfully taunting his little hole with one finger as I leaned his dick on my upper lip and licked his little balls, sucking his ball sack into my mouth.

I went on sucking him off and squeezing his but for a little while until I couldn't hold myself any longer. My cock ached to cum, and I'd do anything at that point to cum inside that boy, reason be damned. As I finally let go of his cock, a string of saliva connecting its tip to my lower lip, and gave a couple steps back, I let the wind cool me down as I looked around for solutions while Hayden wobbled around as he stepped back on top of the chair.

I looked from one end of the house to the other, then I looked at the kitchen door, and it dawned on me. "Hayden, get out through the dog door, I'll help you, then we can continue playing."

Hayden leaned back and glanced at the door. "Isn't it too small? I never crawled through it."

"Oh, you'll fit alright," I said, then I pulled my shorts down and stroked my cock at him. "Wouldn't you want to play with it?" He breathed heavily and then nodded back at me. "Good boy. Just collect your clothes as you come."

It wasn't too difficult, but I had to help him pass through, clumsy as he was. One arm out, then his head, and after a bit of fiddling: poof! All done. There he was, a boy not as much tall as the distance of my belly button to the ground, naked and drooling as he looked straight towards my cock. "Come," I said as I guided him by the shoulder. "Let's continue playing there."

He walked ahead of me naked with his clothes in tow towards the guest house me and Freddie are building for his mom. We were well ahead of schedule thanks to Freddie's experience: walls and roof were up, and I spent the last few days applying mortar on the bottom floor while he indulged the boss with the plumping needs of the luxurious-to-be bathroom. "To the stairs," I told the boy as I grabbed and dusted off a stack of tarp nearby.

"Will I suck yours like you sucked mine?" He asked looking down at me halfway through the staircase.

"And more!" I promised him.

He wandered through the many rooms in progress while I took the first door to the left where the aforementioned bathroom will be. I laid out the tarp over the floor in layers to give the boy some cushioning to his knees while he waited behind me, covering his cock and balls with his hands. "Why are you hiding them?" I asked, laughing as I got naked myself. "You don't need to hide anything," I added as I stroked my cock in front of him while walking backwards. Hayden followed me, eyes locked onto my cock, and eventually stepped over the tap. "Now kneel."

"Why doesn't mine work like yours?" He asked as he tried to pull his skin back, to no avail. "Like, it covers everything but when you pull back I can see the whole head. It looks so good!"

I motioned for him to give me his hand, then placed it over the base of my cock and taught him how to stroke it. "You're too young. Yours will come out, you will see," I explained to him. I had to muster up incredible concentration not to cum as I looked down to his hand trying his best to wrap around my cock.

"I can barely touch the tip of my fingers," he said, amused. "See?"

"I can!" I said as I gently let his curly hair flow between my fingers as I rested my hand on the back of his head. "Now open your mouth. Wide."

Hayden, obedient as he was, opened his mouth as much as he could. I let my cock hover over his face and rubbed the urethra against his stuck out tongue. With his chin touching my balls my cock was perhaps just half an inch longer over where his hair met his forehead.

"Ith-shhmhells-funee."

"What?" I asked as I raised my cock.

"Your cock. It smells funny," he repeated.

"Hell yeah. You like it?"

"So much!" He replied, smiling up at me.

"I'm glad!" I returned the smile. "Now open wide for real now."

As soon as he opened his mouth again, I pulled my foreskin back and slid my cock right inside. "Mind the teeth," I advised. Much as his fingers, his mouth couldn't quite take the thickness in stride, but Hayden damn well tried his best. I was gentle in the first thrusts to give him a little taste, yet he still gagged but did not complain. "Try to work your tongue around it while my cock is in," I instructed him, forcing him to open his mouth wider to give his tongue enough room to slither under and around my shaft.

It all felt familiar to me, even though it was my first time with a boy. And Hayden was handling it better than I did when I was as young as him.

I pulled out once I noticed Hayden was coughing as he tried to breathe. He never let go of my cock as he coughed his lungs out "You okay, boyo?"

"I'm okay!" He exclaimed in between coughs. "Don't worry about me."

"Right-o," I said. I carefully lifted his head to face me by pulling his hair up and slapped his cheeks with my cock. "I'll try to go a bit deeper now, okay? Slap my thigh if you'd like me to pull out."

"Okay!" He said after wiping off spit from his chin. "Will do."

"Open up."

I held his head with both hands as I gently pushed my hip forward. His lips were about a third of the way around the length of my shaft, and I already felt some resistance. "Here," I said as I drew an imaginary line in my cock, just a hair beyond where the tip of his nose reached. "Let's try to get here."

I increased the strength of my grip as I pushed further. The boy coughed, snorted and pinched both my thighs, but no slap. Getting where I wanted was easier than expected, but I knew I had to do baby steps.

I pulled out almost all the way but still kept the head in to give Hayden some space to breathe. He took deep breathes, but did not try to get away from my cock. "There, there," I comforted him. "Pretty easy for now, right?"

He looked up at me, tears flowing from his eyes, but with a devilish smile unmistakably etched to his lips. I relaxed my grip on the boy's head and fucked his mouth softly while he moaned as loud as he could, wrapping both hands around my cock and stroking it while he did his best to feel the tip of my urethra with his tongue.

I had no doubt Hayden would be addicted to cock from there on.

I pulled it out once more, got down to one knee and stole him a kiss. Hayden had trouble figuring out what to do with my tongue invading his mouth, and unsure as well as to what he should do with his own. But we didn't part lips. He eventually got the hang of it and began to imitate my movements as best as he could. "It tickles," he spoke softly as he looked onto my lips.

"Yeah, beard does that sometimes," I said in between gentle kisses to his mouth, cheeks and chin. "Feel good, isn't it?"

"It does," he said as licked his neck and jaw. "It all feels so good."

"And I got more new experiences for you," I whispered to his ear.

I got up on my feet again and Hayden immediately went on to continue sucking my cock. "You know when you always observe me take a piss while I work?"

"Uh-huh," he said with a mouthful.

"Well, let me try to give you a little taste," I said I as took my cock out of his hands and stepped back. I held onto his jaw and lined my cock perfectly towards his mouth. "Open it."

As soon as he did as instructed I let out a first stream of hot piss directly on his throat. My foreskin was pulled back, so some of it ended up spraying over all over his face and chest. Hayden coughed and immediately got up. "Oh my god!" He exclaimed. "That's pee!"

"It is. There's more of it still," I said as I stroked my cock and waited for him to come back to his senses. "How was it?"

"Weird!" He answered quickly.

"But not weird bad, right? Just weird weird?"

"I dunno," he said as he calmed down. "I guess just weird weird."

"Then you'll get used to it. Now back to your knees."

Hayden wiped off the piss from his face as he kneeled down again, then closed his eyes, breathed heavily and, to my amusement, licked the very hand he wiped his face off with.

"Getting used to it?"

He shrugged. "I dunno." Then he opened his mouth again.

"Good boy."

I stepped closer and rested the tip of my cock on top of his lips, but he squirmed back. "Do I have to drink all of it?"

"Well... maybe not all of it. I will think about something."

"Huhh," he said, then grabbed my cock and put it over his lips again. "Ok-kay."

"Good boy. VERY good boy," I said as I relieve myself on the boy's mouth. I went slow to give him enough time to drink as much as he could, but some still spilled over his thighs and my feet, which gave me the idea. I held his head in place and stepped back and way from him, changing the direction of the stream from his mouth to his chest, then belly, and finally his cock.

"It's hot," he said. "Feels nice now."

"Doesn't it?" I said, laughing. "Now I'm almost done. How about you lay down on your belly, so I can give your cute little butt a shower too?"

"Of course!" He said as he dove in between my legs and stood on all fours.

Fuck, this boy is willing. "Grab your butt cheeks and spread them apart, I'm almost done." It was the first time I saw his little butt hole. Pink, small, unblemished and innocent. I pointed my cock down and made sure his butt was glistening and wet when I was all done.

But then Hayden stayed there, his butt hole facing me. Inviting me, even. He liked the attention, somehow I knew.

It would not be customary to fuck a hole like this on the first time, but damn, I couldn't think straight. I was set on taking this boy's cherry. "Hayden," I said as I kneeled beside him and laid down on my back. "Sit on my face, then lie over me and suck my cock."

"What will this do?" He asked as he got up and moved on top of me.

"It will make you feel good," I answered.

He positioned his butt right on top of me, and that sight was forever recorded into my brain: the view of a hard, naked and innocent boy, from below. As he slowly descended to sit onto my face, I began to stroke myself faster and faster. I didn't cum already not for sheer will, but for pure luck, that I am sure.

Once he got closer, he hovered his butt above my face unsure of what to do, I imagined. So I pulled him down. His butt wiggled as it plopped onto my face, and my tongue took no time exploring the outskirts of his delicious butt hole. Hayden moaned upon first contact of my tongue and began to wiggle his hip over my face.

I forced him to lie down with one arm while my free hand held my cock upright. He took it in his hands but wasn't tall enough to suck it properly, so he spent his time licking the head while I tasted his hole. While I massaged his thighs and butt cheeks. At times, I could have mistaken Hayden's moans for that of an adult slut. Boy was destined for cock.

I felt cum building up, so I had to gently slap Hayden on the back a few times for him to slow down, but I wouldn't hold much longer. In fact, if I hadn't taken him off of me, I would for sure have cummed in his mouth. Not bad at all, but I had bigger aspirations.

I stood there catching my breath and trying to not touch my cock to calm down a bit while he looked at me with legs spread apart, confused. "Are you okay?" He asked, worried.

"Oof, I'm okay," I said. "I'm just about to climax, so I need to catch a breather."

"Do you want some more milk? I can get it for you," he offered.

I laughed. "No, no, just wait a few seconds," I said. "Just come here and kiss me."

He got on his knees and leaned over to kiss my lips. He himself tried to push his tongue inside my mouth as he crawled over me and laid on top of my chest. "Beautiful boy," I said softly while we kissed.

We kept on this tender loving moment for a couple of minutes, more than I needed to calm down, surely, but kissing him was just too good. And now I was ready to deflower him. "Hayden," I began saying while we kissed and caressed each other's hair, "how about I put my cock inside your ass?"

"Yes, mister," he innocently answered right away as my middle finger circled his butt hole, which puckered at every touch. "I want this."

"You want me inside of you, yeah?" I asked again lovingly as I pushed and wiggled the tip of my finger inside. With little warm-up, a finger went in easily and without resistance, so I tried to slide another finger in, and I felt his chest quiver on top of mine as he squirmed. "Just relax," I said as I pulled his face back to meet mine. "Relax and tell me you want me inside of you."

Hayden groaned softly and moaned a good deal while I kept on pushing two fingers in. Once both were two knuckles deep, I stopped and hugged him. He came to my ear and whispered, "I want you inside of me, mister."

I looked into his tender eyes and we kissed again, then pushed him aside and got on my knees. "Alright, Hayden. I need you to stay on all fours now, okay? I'll try to slide this inside of you," I said as I slapped my hand with my cock. "Try not to squirm too much, or it will make it harder for me. Do you understand?"

He nodded, then followed my orders. I positioned myself behind him and began drawing circles around his butt hole with my cock. Once I felt he was more relaxed, I put the tip right on the door and held onto his hip with one hand. "I'm going in now," I said. He moaned as he felt pressure build up against his butt, but he kept on breathing loudly and trying not to pucker up.

My head wasn't going in without some tough negotiation, though. So to speak. So I held him tighter on the hip and tried to force it inside in one go. Hayden jumped forward once the head went in, cried loudly and his muscles became stiff all of a sudden. "Ouch!"

"Hey now, hey now," I said calmly while I held onto his shoulders to prevent him from breaking the lock. "It's done now, the head is in, now it's all smooth sails," I explained. "How about I stand still and let you get used to it for a bit?"

"Ouch, ouch," he kept on saying. Then I noticed he was leaning his upper body in just one arm, while the other was busy stroking his little dick. Made me smile that he kept on braving on and enjoying himself anyway. "Can we wait longer?"

I looked down. His butt clenched around my shaft, us both glistening from piss and sweat, breathing heavily. "We can wait," I assured him.

Hayden touched himself faster and faster as he became used to my cock inside him while I massaged his back. I probed his ass by pushing just a tiny bit inside, but he would stiffen up almost immediately. At least I knew it wouldn't get any more difficult for him from there on. It was my cock after all, not Freddie's.

After two minutes or so, he stopped squirming so reactively to my hip's every movement. "Hey, boy, I need you to toughen up a bit, okay?"

"It is going all in, right?"

"Yes," I told him. "I want my balls to touch your butt."

He took deep breaths, and I felt the grip on his butt loosen up. "Okay, I'm ready."

I began pushing. "Try not to scream, okay?" I said. Hayden endured it well for the first half, but on the second half he broke down groaning and moaning loud. "Hmmm, ouch! Ouch!" And yet, he did not stop touching himself for one second while I pushed further and further in.

When he felt my balls touch him, it was if a burden was taken off his shoulders. He let out a deep breath, seemingly relieved it was done, and reached behind to feel my cock deep inside him. "That feels so weird," he said, exasperated.

"But weird bad or weird weird?"

"Weird good," he said, smiling. His face was dripping sweat.

"Good boy."

"I tried touching myself before, but it never felt as good as now."

"You need the right motivation," I said as I massaged his back. "How does my cock feel inside?"

"Feels difficult," he admitted. "But nice."

"That's good." I wrapped my hand around his neck and pulled him up for one more kiss. "Now I'm going to fuck you until I cum inside you, okay?" I whispered to his ear.

He closed his eyes and began breathing heavily again. When he looked at me once more, he just nodded and waited. I pulled back and pushed it in, and he groaned. His hips were trying to increase the distance from mine by pure instinct, but I held onto them tightly. Then I did it once more, balls deep, and he moaned loudly. With each thrust I went slightly faster and stronger than before.

Hayden never stopped moaning and groaning, but after some time his butt gave up trying to resist, so I pushed him against the floor, laid myself on top of him, leaned over my hands and began to fuck him hard, balls slapping his butt as loudly as I could. Hayden tried to chant something, but his words were completely undecipherable among his moans and groans.

I was about to cum, so I laid myself completely on top of him, skin against skin, and slowed my speed. I could hear Hayden's breathing under me matching my own as I reached climax. We both cummed together, moaning in unison, as I flooded the boy's ass while he had his first dry orgasm.

As cum kept flowing out I kept on fucking him slowly until my whole body shivered, and I fell on his side with my cock sliding out of him, allowing a river of cum to ooze out of the boy's hole and onto the tarp. "F-fuck," I said. "That was good."

He said nothing in response. Instead, he came closer and hugged me, resting his head on my armpit, as exhausted as me.

We laid there naked for a good while, looking dearly at each other, exchanging loving kisses.

"No, don't wear your clothes," I said as we prepared ourselves to go out. I was already fully dressed and trying to fit the tarp inside my backpack. "You smell of piss, if you wear them your mom will notice."

"But what will I do? Walk naked back inside?" He asked, puzzled. "And I'm oozing out, too," he added as he held onto his butt.

"But didn't you already come here naked?" I said, laughing. "Now that I think of it, asking you to bring your clothes was a bit silly."

He laughed back at me. "You're silly, mister!"

I got up, backpack in tow. "Shall we go, then? I'll help you get back in, and then you go straight to shower. Deal?"

"Deal!" He said as he took my hand, and we walked back together to the main house.

We should have spent a little over an hour in total. As I got near the kitchen, I still saw no movement inside. Relieved I lucked out, I gave Hayden a goodbye kiss before I helped him crawl through the dog door again. "Will I see you next Monday?" He asked before going in.

"Absolutely!" I told him, then we finally waved each other goodbye through the window and I went on my way.

On the pathway to the front, I heard the sound of a key going through a keyhole and I got a shiver in my spine. Mother or uncle, I thought to myself, one or both. I considered tip-toeing my way back to get out later, but I didn't hear the door being opened, only the key being turned. Carefully, I walked closer to the front door, trying to see whoever it was who was there.

"Freddie?!" I said discreetly.

"Whaa-" Freddie said, startled, dropping the key.

"Where did you get that key?" I asked, aghast.

"Weren't you supposed to be home by now?" He asked back. "And where are your tools?"

I slapped my forehead as I realized I had forgotten about them. "Right. I-" I started saying as I turned back to the pool, but was interrupted by Freddie, who touched me by the shoulder.

"Why are you so sweaty and sticky? You smell of..."

I turned to him and his eyes looked down at my shorts. "The boy is home, isn't he?"