CHAPTER FORTY-FOUR Cole

"We were swamped today," Chad said, moving his hand over my thigh as we sat side by side on the upper deck of my home, just outside the master bedroom.

"And on a Thursday, even," I responded. "Looks like you picked a winner, baby boy."

I don't remember when I'd started calling him that, but he'd responded positively when I first had, so the endearment stuck.

He squeezed my thigh. "Looks like I have," he said, leaning into me. "The business idea was a good one, too," he added, lifting his hands over his head and stretching. My heart swelled at his cheeky comment.

He had a faded pair of my old boxers on. A plaid Abercrombie Fitch pair I think I'd had since college. You could have put a garbage bag on him and he'd be the hottest, garbage bag-wearing stud alive. Four or so inches of white skin was visible below the boxers' hem because he never wore anything short when in the sun.

"Your skin is so white," I noted, sliding my hand along the bottom edge of the boxers. His crotch bounced from the promise of something more. "And there he is," I joked. "Must be what, twelve hours since?" I asked.

"Only that long?" he mumbled, dreamily moving his hands inside his boxers. "Seems like forever ago."

"You mentioned you were tired," I teased.

He tilted his head in my direction, catching my eye before looking down at his burgeoning crotch. "You ever wonder why they put that opening in the front of boxers?" he asked, moving his hips lower in the Adirondack chair and staring at the tent he was building within the boxers.

"Hmmm?" I whispered. "I never noticed before you mentioned it just now." I ran a finger along the slit in the boxers, his dick clearly outlined in them. I pretended I hadn't noticed the raging hard-on. "Seems like a waste of an opening unless one found a use, wouldn't you say?" I asked.

"S'pose so," he muttered, suddenly using a southern twang to go along with his dimwitted boy act he'd just enacted. "Figgered a man with your high-falootin' ways mighta known about it."

I swallowed a need to bust out laughing. Chad was full of surprises, and tonight looked like a little role-play might be in the cards.

"Where you come from, boy?"

He jacked a thumb over his shoulder and behind us. "Out there," he stated. "The road mostly."

"No home?"

"Just this one since you picked me up on the highway, mister."

He positioned the head of his dick near the slit from inside where his hands still were. I let the banter lay there for a moment to add to his excitement. From the looks of the size of his dick, he was fully into something we'd never discussed: role play.

"You know you can't be staying here for free, boy."

"Figgered that'd be the case. Y'all Yankees always have your price, dontcha, mister?"

"What you got to trade, boy?" I asked, finding myself getting into the game.

My cock was fighting the briefs I wore as I locked in on Chad's erection. His hips slowly gyrated as he sold his story. The only light was the moonlight overhead and boy did it do a lot to enhance his skin.

He moved a hand to one of his nipples and slid a finger back and forth over it while his other hand remained in his boxers. "This ‘bout it, as far as tradin' goes," he said, pushing his entire cock out of the slit in front. "Been doing the trick so far as I hitch cross country, mister."

"Hitchhiking, are you?" I stared straight ahead at the ocean, glancing at his exposed cock occasionally. If he wanted role-play, I was in. "You're a dirty boy, aren't you?" I asked, licking my lower lip in pleasure, still trying hard to ignore his cock.

"Been told that a time or two, but men like you seem to be inclined to like my wiener, mister."

"We do, do we?"

"I'd be happy to stand up and let you take a closer look, mister man," he teased. "Maybe even let you touch it or sumpin' like that."

"What if I wanted to suck you off, boy? You up to something like that?" I asked, rubbing my cock as Chad suddenly pretended to be disinterested in the entire made-up scene.

He was good. Very good. I hadn't expected a sweet and angelic young man like him to be so open to adventurous experiences. But then again, my experience was limited to one man only. But in a short month, he'd been unveiling a little more each session. Chad was enthusiastic in any lovemaking we'd had so far. All I had to do was express an interest, and he was down for it. The enthusiasm was contagious and freeing because I'd become a far more verbal lover since the discovery.

He stood up and stepped in front of me, looking past me like he had zero interest in what was happening. He was selling the story so convincingly that I was nearly ready to orgasm. "Want me to pull ‘em down, mister?"

"Yes," I whispered hoarsely. Fuck, this is hot.

Chad turned around, facing away from me, and bent over as he pushed his boxers to his ankles, his sweet pucker lined up directly in my face. He waited a moment before standing upright. I had my hands in my briefs and was stroking my cock.

Without turning his body, he looked back at me shyly. "You like that boy pussy, mister?" he asked, sticking his finger in the corner of his mouth and pouting.

Jesus!If I wasn't near losing my load before, I was now. I stared at his face before dropping my eyes slowly down his backside, taking my time and letting him watch my desire as I surveyed the breathtaking territory. His perky little mounds of flesh drove me crazy with the need to bury something between them. My cock, my tongue, my whatever.

"You ever had a man in that ass, boy?"

"No, sir. I ain't never done nuttin' like that."

"Don't look at me, boy," I barked, motioning for him to look away.

Chad turned his head away, and I let time slowly tick by as I examined every perfect inch of his backside. He was long and lean, with a narrow waist, and two globes of flesh whose shape appeared to be carved from marble. But unlike marble, his ass was velvety smooth. I'd been between his cheeks several times, but somehow he was managing to create a first-time scenario.

"What you doin', mister?"

"Deciding," I muttered.

I let him stand there for another three minutes or so. I liked his little game and the more I got into the scene, the hotter my desire, the more fantastic the options seemed before me.

"Turn around, boy," I grunted. Chad slowly turned around and smiled like a little slut. "I've decided you're going to suck my cock. Time to earn your keep, boy. I might even have to fuck that pretty ass of yours."

"I ain't never done that, mister."

"Whatever," I huffed, nodding toward my bulge. "Pull them down, boy. With your teeth." Chad dropped to his knees and fell face forward into my crotch. "Pull them down," I ordered again, nastier this time.

He tugged on my briefs with his teeth while I lifted off the chair so he could get them off me. Using his mouth, he moved them to my ankles, where I lifted my feet out of them. Chad remained at my feet, waiting for instructions, still avoiding eye contact.

"Lick my balls, boy. Nice and easy until I tell you to stop. You understand?"

"Yes, sir."

I held the back of his head and moved him over my balls, thrusting my hips forward as he ran his tongue over me. After a couple of minutes, I held the sides of his head near the jawline and pried his mouth open.

"Open wide, boy," I said, leading him toward my cock and feeding it to him. "You've got a lot to learn, boy, and you better be good at it or it's the curb for you."

I held him over my cock and pumped into his mouth, losing myself in Chad's act, his idea, his fantasy. If he'd wanted to lead the entire scene, I imagined he would've spoken up, but he didn't, so I played along the only way I knew how. I led the way while playing into his scene of owing me a debt that only his body could repay.

He came off my cock and stared up at me. "It's so big, mister."

"But you like sucking cock, don't ya, boy?" I stated. "Living on the streets and giving your ass away. Is that any kind of life?"

"But I never did give my butt away, mister," he corrected. "I'm not that kinda boy."

"Bullshit!" I hissed, surprising Chad with my commitment to character, as he grinned for a quick second. "I don't believe you."

"There's no way I could take that in my butt, mister," he said, pointing at my cock. "I think that might hurt my little boy pussy."

If I hadn't been so turned on by Chad's innocent role, I would've burst out laughing at him, but he was having fun, and I was being introduced to a side of him I had not expected to find. And I fucking loved it!

I grabbed him around the neck from the front side and stood up carefully as I brought him with me. "You're no ass virgin, boy," I spat, leading him through the open glass wall to the bed. "On your back, boy." I ordered, shoving him toward the bed.

"But I'm afraid, mister," he feigned, flopping on his back and immediately pulling his knees to his chest. "I know I'd just about hate it if you ate my butt."

I returned from the nightstand on the other side of the bed and tossed a condom and lube on the bed next to him. "I'm going to fuck you with a condom on, boy. I don't trust where your ass has been." I came to my knees beside the bed, where his ass was on full display. "Let me taste this boy pussy," I growled.

I placed my tongue on his hole and flicked it. Chad quivered in anticipation while he kept his knees drawn toward him, giving me full access. "That feels good, mister. What are you gonna do next?"

I reached for his cock, which was swollen with desire, and continued burying my face in his hole, munching and slurping. Chad writhed on the bed while keeping his knees up, his feet flopping around as he let himself get fully immersed in his role. I moved higher and took his cock in my mouth, exchanging a finger for my tongue as I began to probe his asshole.

"You're tight, boy," I said. "Real tight, like you said you were."

"What ya gonna do, mister? I've never done this sorta stuff."

I stood and reached for the lube. "Open those eyes, boy, and I'll show you what I'm about to do to your trashy little hole."

I stepped back and dripped lube on my cock, tossed the bottle by his head, and stroked my cock nice and slow.

"Where's that goin', mister?"

I ignored him and grabbed both of his ankles, lifting them until his legs were straight up and down, securing them in one hand while I lined up my dick to his hole.

"Time to earn your keep, boy. This is what you wanted, ain't it?" I asked.

"Do I have to?" he asked, stroking his dripping cock. "I mean, if you want me to."

I leaned forward, grabbing one ankle with my free hand, maintaining my grip on the other, and spreading him wide. I stared at Chad's face as I sunk deep into him in one slow movement until I was buried completely inside him.

"You like, boy?" I asked, remaining all the way in and holding.

"Mm-hmm," he moaned, biting his lower lip and batting his eyelids at me, still staying in character as the street kid who had to give his body away. "Your dick is so big, mister."

I pulled out and waited for a second before pushing in again, and then repeated the same motion, slow and easy, over and over, as Chad moved his head from side to side, moaning louder with every thrust, his breath elevating.

I knew when Chad was completely available for more, when his hole relaxed around my sizable cock. Time to up the ante. My cock plunged all the way in where I'd hold for half a second before pulling out and driving back in, pumping harder with each thrust until Chad was whimpering like a wet puppy on a rainy night.

"Oh, yeah, boy. Take that Daddy dick," I growled, keeping Chad's ankles in my control as I exposed his ass to my cock. "You like, boy?"

"Yeah, fuck me good, mister. You dirty man, you. I bet you pick us hitchers up and then fuck them boys like this all the time, dontcha, mister?"

"When they're shaking their pussies on the side of the road, I do," I huffed, increasing the assault on his asshole. "You lied to Daddy, boy," I insisted. "Claiming you're a virgin. Please, you little slut. You're a nasty little fucker, aren't you?"

"Shut up and fuck my ass," he said, narrowing his eyes as he struggled to hide a laugh. "I ain't afraid of you, city dude."

I yanked him to the edge of the bed and moved the backs of his knees over my shoulders, and then leaned forward until said knees were next to his ears and pumped into him hard. His dick ground against my stomach as I pulled him tight against me. Chad moved his hands to my ass and pulled me into him hard, matching every thrust I delivered.

"How's this, boy? Hard enough for you yet?" I growled, burying my face in his neck and biting on his skin.

"Oh, mister man. Oh yeah, fuck me harder, mister. Harder!" he yelled, wrapping his legs around my waist and meeting every thrust with a grunt of pleasure.

"You ready, boy?"

"Come in me, mister. Claim my ass."

"Fuuucccckkkk," I yelled, releasing a load unlike any I'd experienced. I knew it was Chad, but the whole role-play thing had me at another level of pleasure.

Chad's entire body stiffened as his dick unloaded between us, the friction of our grinding getting him there. "Oh, yeah," he cried. "So good, mister. So good."

Our mouths met, and we kissed passionately. Aggressively at first, before tenderness took over, and we held one another tightly as our breathing regulated. I was totally spent from the unexpected scene I'd just participated in.

"Damn, that was hot," I whispered in his ear, rolling over and pulling him on top of me. "Incredible."

Chad smiled down at me, his hair almost touching my eyes. "I love you, mister," he whispered.

My eyes widened before I remembered we were role-playing. "We're still playing, right?" I asked.

He lovingly smiled at me. "Nope. This is me."