Due Diligence

fucking, intergenerational

by Natty Soltesz

I needed a promotion at work and the competition was fierce. In my desperation I turned to my son Chase.

“Chase, son, I have to ask a favor of you,” I said one night after I’d finished washing the dishes.

“Yeah, Dad?” he said, looking up from where he was studying at the kitchen table. I sat across from him. 

“I’m inviting my boss, Mr. Bonasaro, to dinner on Friday night. It’s really important that I impress him…and I was wondering if you could help me out with that.” 

“How?” Chase said, chewing on the end of his pencil. 

“Well, son, there’s rumors about Mr. Bonasaro – he’s a married man, but, well, most know that he likes to have some fun on the side with cute and, uh, younger individuals…boys and girls.”

“Yeah?” Chase said, arching his eyebrow. 

“Yeah,” I said. “And, I mean, you can totally say ‘no,’ but I was wondering if, when I brought him over for dinner, you could…you know, maybe wear something he might enjoy. Your wrestling singlet, for instance. You could pretend like you just came back from practice…”

“Dad, are you asking me to seduce your boss?” Chase said, widening his eyes.

“Well, not seduce him necessarily, but just give him something to look at, at least…” Chase picked up his phone and started tapping and scrolling. “What are you doing?”

“I’m looking for a pic of him,” Chase said.

“I mean, I know you’re queer and have a really…active social life,” I said, trying not to say what I was thinking, which was that my boy was a bit of a slut. I mean, he had every right to be – he was gorgeous and fit, a really fine and muscled specimen of youth who got plenty of attention from men and women. 

“This him?” Chase said, showing me an image of my boss on his phone.

“Yeah, that’s him,” I said. Chase glanced again at his phone, nodding in approval at the image of my boss’s handsome face and impressive frame. 

“He’s hot,” Chase said. I wasn’t surprised he thought so. A lot of the office had a crush on Mr. Bonasaro – not just because he was our boss, but he was a well-built, salt-and-pepper haired lady-killer. 

“So would you be willing to…” I continued.

“Sure,” Chase said, cutting me off. “Whatever you need, Dad.”

“That’s my boy,” I said, and ruffled his hair.

—

“So my son is going to be joining us at some point,” I said to Mr. Bonasaro that Friday after he’d arrived at my house.

“Oh, good,” he said, looking appraisingly at my home. “He’s in high school?”

“Yeah, a senior…on the wrestling team,” I said.

“Oh really?” Mr. Bonasaro said. His interest was apparent; I took it as a good sign.

We had our meal and I was just about to serve dessert and bring up my interest in the promotion when Chase came home. 

“Hey Dad!” Chase said. “Sorry, I was out for a run,” he said. He hadn’t worn his singlet, but he’d done me one better and came in wearing nothing but his short running shorts, his nearly nude and smooth-as-butter body covered in sweat. “Who’s this?”

“This is my boss, Mr. Bonasaro,” I said. Mr. Bonasaro rose and held out his hand.

“Please, call me Tony,” he said. My eyes widened at that. I’d never called him by his first name.

“Cool, nice to meet you, Tony. I’m Chase,” he said, looking into my boss’s eyes as he shook his hand. 

“We’re just about to have dessert, join us,” I said.

“Sweet,” Chase said, pulling out a chair close to my boss and smiling at him as he sat. “So you’re my dad’s boss, huh?” 

“Sure am,” Tony said. I set three slices of cake down on the table in front of each of us and sat across from my son and my boss. 

“Gonna give my dad a raise?” Chase said. I was about to apologize for my son but before I could say anything Tony spoke up.

“I don’t know…depends on how far he’s willing to go for his job. The employer/employee relationship is based on what each has to offer the other,” Tony said.

“Oh Dad has a lot to offer,” Chase said. He’d turned toward Tony and now leaned back in his chair, to display his rippling muscles, his fine-toned teen physique. Tony looked him up and down then turned to me.

“Is that right, Franklin?” he said.

I nodded. “What’s mine is yours,” I said.

“Hm, well, in that case, maybe I’ll skip this cake and get to know your son a little better,” he said, his eyes swarming over Chase’s body. “Is there somewhere we can go that’s a little more private?”

I stood up. “You can use my bedroom,” I offered. “But, uh, there’s one thing…” 

“What?” the two of them said at the same time.

“Well, I just feel like I should monitor the situation…it is my son, after all…”

“Dad wants to watch,” Chase said.

“By all means,” Tony said, and I led the way to my bedroom. Chase raised his eyes at the candles I’d lit for atmosphere. I sat in my chair across from the bed.

“Just pretend like I’m not here,” I said. Chase rolled his eyes and Tony smiled. 

“Won’t be hard with this fine piece to occupy my attention,” my boss said, grasping Chase’s shoulders then running his hands down his muscled arms.

“I’m all yours, boss man,” Chase said as Tony caressed my boy’s sweaty chest and tight stomach.

“Let’s get it all out on the table, then,” my boss said, and knelt down in front of Chase to slide down his running shorts. His eyes widened when he saw my son’s massive, shaved cock. To be honest, mine did too. I hadn’t seen my son naked since he’d been a boy, and I’d had no idea he’d matured so impressively.

“Very nice,” Tony said, and immediately went down on Chase, taking my son’s limp, heavy cock between his lips and holding it in his mouth.

“Oh fuck yeah,” Chase said, glancing over at me with a look of surprise. It wasn’t long before Chase was hard. My boss sucked him hungrily, moaning as he bobbed his head. I never would’ve figured my controlling employer was a first-rate cocksucker, but that did seem to be the case.

“Damn I love teen dick,” Tony said before stuffing Chase’s cock back down his throat. 

“You suck it good,” Chase said. I watched in amazement. It was one thing to see my son in action as a fully sexual adult, and yet another to see my butch boss on his knees, worshipping cock like he was born to do it. Even in his submissive position, Tony held his air of control, keeping hold of Chase’s cock as he stood and wiped his mouth. 

“You eat ass, kid?” he said as he unbuckled his pants. Chase glanced at the full, muscular butt Tony was packing in his pants and nodded enthusiastically. “Good, cause I like it licked deep,” my boss said as he dropped his pants. Out popped his huge, hairy ass. Chase reached back and clutched it. 

“Damn, what an ass,” Chase said. 

“That’s right, kid. Eat it good,” my boss said, and tossed Chase onto the bed. He straddled my boy’s face and sat right down on it. “Oh goddamn that’s the stuff,” he said, eyes rolling back in ecstasy as he ground onto Chase’s tongue. Tony slipped off his shirt and tweaked the nipples on his hairy, well-built chest as he rode Chase’s tongue, matching my son’s muffled moans with his own.

“Eat that big butt, boy. Fuck you’re tonguing me good. Damn, Franklin, your son’s got some skills,” he said.

“Thanks,” I said weakly. My cock was jumping in my pants. I didn’t know what to think about that. It only got harder as Tony leaned forward to suck on my son’s cock while he ground his ass onto his tongue. He wasn’t sucking it so much as getting it wet. And then he stood right up, turned Chase’s body so that his legs were at the edge of the bed, straddled the boy’s hips and sat right down on his cock.

“Holy shit,” Chase said, eyes wide.

“GodDAMN, that’s some good dick,” Tony said as he rode my son. “Now don’t you cum yet: I wanna enjoy this dick for a while.” I watched in amazement as my tough-as-nails boss rode my son’s raw cock like a horse on a carousel. In a million years I never would’ve guessed that he was a bottom, and Chase seemed surprised too.

Tony stroked his hard cock as he fucked himself on my son. He seemed to go into a trance, riding himself steadily and keeping up a stream of dirty talk as he did: “Oh fuck yeah give me that teen dick, fucking shaved raw teenage cock in my ass, so fucking good…”

Chase smirked at me, we shook our heads at one another. Then my son motioned to the hard dick I was pawing in my pants and motioned with his head that I should take it out. Quietly, I undid my pants and unleashed it. Still standing a ways back, I stroked it as I watched them.

“Can I fuck you from behind…sir?” Chase said to my boss.

“You damn well better, kid,” Tony said, and dutifully rose up off Chase’s cock, then positioned himself on all fours on the bed as Chase got up and came around to the older man’s bouncy, spread-wide rear.

“This is fucking sweet,” Chase said as he sank his cock back into Tony.

“Damn straight it is, kid,” Tony said. “You better fuck that load into me when you’re ready to cum, don’t you fucking dare pull out, you understand? Every fucking drop…” Tony continued. He was so lost in his experience he didn’t notice as Chase motioned me to come closer.

“You’ve got me so close, sir,” Chase said. He began to slide his cock all the way out of Tony, holding it for a moment at the maw of my boss’s pink, gaping hole before plunging it back inside again. Each time, Tony would groan.

“Keep giving me dick like that. Fuckin hell, man, I needed this…” Tony said. Each time Chase took it out he would wait a little bit longer before putting it back in. Finally Chase slid out and nodded his head at me. I got the idea real quick. We quickly switched positions and I sank my cock into my boss. Goddamn did it feel good, and he never noticed, I guess because our cocks are so similar.

We kept that up for a good ten minutes, me being real quiet as we switched off again and again, taking turns fucking my boss in the ass with our raw dicks.

“Yeah you like that big ass, boy? You gonna fill me with cum?” Tony said, furiously stroking his cock, his face to the wall as he took our dicks again and again.

“Hell yeah I am, so much cum,” Chase said, laughing quietly and sticking his tongue out at me conspiratorially. I was balls-deep in my boss’s ass and I knew I wasn’t going to last.

I’m gonna blow, I mouthed to my son. He nodded in understanding.

“Oh fuck Tony I’m gonna cum in you,” he said, indicating I should go ahead. I sunk all the way into Mr. Bonasaro and held my cock deep as it unloaded. “Oh fuck I’m cumming,” Chase said, and I held my breath as my dick pulsed and shot.

“That’s it kid blow that load in me, oh fuck I’m gonna cum too…” Tony said.

“Hold on hold on I got more,” Chase said. I could tell he was close so I pulled out and stepped aside, my cock still oozing a little. Then I watched as Chase plunged his cock back into Tony and began to shoot his own load. “Fuck I’m still cumming…” Chase said.

“Damn I can feel it! Goddamn ain’t nothing like teen cock, so much fucking cum…” Tony bellowed as he blew his own load over my bed – not a huge load either, I noticed. Kinda paltry.

I quietly made my way back to the chair in the corner, buckling up my pants and acting like I hadn’t just shot a load into my boss. Tony seemed none the wiser, in fact he looked completely satisfied – as happy as I’d ever made him, as an employee. Chase collapsed back onto my bed as Tony got himself dressed.

“Well, Franklin, I have to say, you make a compelling case for your advancement in the company,” he said as he buttoned up his shirt. “Let’s talk on Monday.”

“Sounds good, sir,” I said, and Chase gave me a wink.