Son's Unconventional New Job

Disclaimer: This is a fictional story about a sexual encounter between a father and his son. If it's illegal for you to read this type of erotic material, please close the page or click the back button.

"I can't give you anymore money. I'm paying your car insurance, gas and incidentals but if you want anything more you're gonna need to get a job. You're 18 now, it's time you start working. I'm sorry bud." I had to deny my son's request for some fun money, I hated to do it but it's time. I had my first job at 16 but Tyler hasn't even worked at a summer fair yet.

"Ah, come ooooon dad, I don't wanna flip burgers just so I can go to the movies or buy a video game. That's crazy." Tyler crosses his arms in defiance. He's not spoiled but he's far from self-sufficient. That's on me though and it's time to course correct before it's too late.

I felt bad for cracking down, I know how expensive most things are and how long it can take to save up enough money to afford the fun stuff.

"Alright, look, I'll cut you a deal. I'll ease you into it, once you start working I'll pay half the cost of your games, shoes, trips to the movies whatever it is you're trying to get. I'll help you out for a while. But it is time you start understanding the concept of money; how it's earned in relation to how easily it's spent. I really am sorry, growing ups the pits." I open my arms and Tyler walks into my embrace. Hard to accept he's all grown up when I still easily envelope him in my arms.

"Dad, that's not an expression." He quietly corrects me.

"Yeah, kiddo, it is. It's just a little archaic." I smile and kiss him on top of his head before ruffling his hair as he breaks off the hug.

"A relic from your time in the 1900's, huh?" He retorts, teasing me about my old age. I'm only almost 40 and I still feel young at heart. I gotta admit, don't look too bad either. I'm no muscle God but having had a consistent gym routine over the years has kept my belly at bay and my shoulders are naturally broad. Lifting weights weights has kept my strong, toned muscles nice and big.

"Hey now, I may be twice your age but I'm far from an old man, got it?" I hold his face in my palms and look into his eyes. My sweet boy, well young man, all grown up and soon to leave the home he grew up in to head off to college.

I guess that'll make me an empty nester. The first time I'll live alone in my whole life. His mom left us when he was about ten and we've gotten along just fine without her, now with Tyler leaving soon too, I wonder how I'll fair without him. I miss him already.

I lean down and kiss him on his forehead, "I'm proud of you, you know that, don't you?"

"Yes, dad. You tell me almost everyday, I'm starting to think you're just trying to convince yourself." He raises an eyebrow inquisitively, smirking.

I start to tickle his lean, toned sides and tell him I really am proud of him. "But I'm serious about the job, it'll do you some good."

"Fine, but don't expect me to share my employee discount!" He jokes as he walks toward his bedroom.

The next day after I get home from work, Tyler greets me in the living room with a hug. "Dad, I got a job! I've made $50 already on my first day." He excitedly shares his news.

"See, son, I knew you could do it!" He runs into my arms and I spin him around. As I lean forward to kiss his cheek, his face turns toward me and our lips accidentally meet. We don't move for a beat until I reluctantly pull away. I chub up a bit from the contact. It's been too long since I've kissed anyone, my body must've gotten some wires crossed. I haven't gone on a date in a while and I couldn't tell you the last time I had sex, that's gotta be why I'm getting hard after the accidental lip lock with my own son.

"Yeah and it's all online so I don't even have to leave the house. No smelly uniform! But it doesn't come with an employee discount either. Sorry dad, no free burgers." He says with a big smile on his cute face.

I couldn't help but smile back at him. "Online, huh? Well that is the future, son. I'm proud o-"

"Yeah, I know dad. Thank you." He interrupts me, already knowing where I was going. "Alright I'm going to get back to it." He turns and heads back to his bedroom, which now seems to double as his workplace.

A little while later I hear him calling for me.

"Dad, can you help me?" Tyler shouts from his bedroom. I get up to go check on him and see why he's calling for me.

"Yeah, bud, what do you ne-" I stop at his doorway as I see my son laying naked on his bed with one hand on his hard cock and the other rubbing on his hole, two fingers repeatedly entering him. The squelching sounds and the scent of his most private parts fill the room and I'm shocked at his brazen openness. We've always been pretty comfortable around each other but never on this level. I stood there in shock staring at my boy naked on his back with two fingers in his asshole.

"Dad, can you help record me? I want this camera to stay here but I was hoping you could also use your phone and record me at some other angles? It'll really help the content." He asks as he nonchalantly continues finger fucking himself.

I knew he was flexible from his days on the track team in high school but I had no idea he was capable of putting his legs behind his head. This was quite the scene and I had to try my damnedest not to spring wood right there in front of him but damn, this was a sexy sight to see.

I pull my phone out and start recording my son as I'm watching him finger fuck himself. I couldn't help but feel like I was intruding on something private. He moans and tilts his head back, enjoying the feelings he was giving himself.

He adds a third finger and his hole is really loosening up now. I stare in awe as his sloppy hole eagerly swallows his fingers. I had no idea his body was capable of such things or how he had even ventured to discover it. I was impressed at how natural and easy he made it look.

I didn't think it was too appropriate, me standing here watching and recording this sexual act, but how can I deny my son's request when he needs help with his job? What kind of job did he get that requires him to perform such a lewd act?

"Wow buddy you're really good at that." I say impressed, recording a close up shot of Tyler finger blasting himself. I get down to eye level to get a clear view of my sons beautiful, winking hole. His hole was hairless, pink and clearly made to be entered.

He opens his eyes and smiles up at me, "Thanks dad. I've been practicing for a while now, I never thought it'd come in handy as a job skill. Working feels a lot better than I expected." He says over the squelching sounds of his hole swallowing his fingers. Having a casual conversation with my son while he works his pink rosebud and I film it was definitely not how I imagined this day going. But if my hardening cock was any indication, I sure as hell was enjoying it.

"Actually, uh, I could really use some help, my wrist is cramping up a little. Do you think you could take over?" He says as he rubs his wrist a little. "You can use this." He hands me a thick purple dildo that's almost as big as my cock.

"Woah bud, are you sure that's not gonna hurt you?" I worry about causing damage. None of my exes were willing to try butt stuff so I wasn't well versed in the art of ass play.

Tyler chuckles a little. "No dad, I've been using that one for a while. I can easily take it now, it feels so good. Watch, try it out." He says as he removes his fingers from his hole with a pop and spreads his cheeks wide. His hole is on full display, still slightly gaping. It looks hungry, anxiously waiting for the dildo to stuff it up.

"Should I lube it up first?" I ask, unsure how to proceed.

"No need, I've been playing with my hole for a while, it should be pretty slick already. Just slowly push it in." I place the head of the dildo at his entrance and do as he says. He's right, he was pretty wet and ready. The head plopped in and easily started sliding down my boy's chute. He moans deep and his head tilts back as his eyes close.

It was a wild sight to behold. Tyler had his ankles behind his head and was holding onto his butt cheeks as I'm penetrating him with a massive dildo. He looked incredible.

He must be some kind of a pornstar now. This isn't really what I had in mind when I told him to get a job but if my rock hard cock was any indication, I think a lot of people would be happy to pay to see him in action. Here I was lucky enough to get free admission and a front row seat.

"Ohh dad, that feels so good. Angle it higher so it hits my prostate harder." I follow his direction and aim it at his G spot, hoping I'm hitting it right. "Oh yes, like that. Mmm, that's so good." Yep, I think I was.

"Does this really feel good? Do you like it?" I ask, genuinely curious. I've never played with my ass before and none of the women I've been with seemed interested to try it. The look on Tyler's face really seemed like he enjoyed it.

"Hell yes, dad. Faster please." I pick up the pace a little bit, nearly pulling all the way out before slamming it back into him. "Nnh, yeees." His toes flex and curl as his tight, hairless balls clench in their sack. He pulls on his cock a few times and points it towards his face, sticking his tongue out in attempt to lick the head and I was surprised to see he could make contact. I had no idea that was possible! Tyler gives his dick a few licks before stretching a little bit further and sucking the head in.

I momentarily stop pounding into him as I'm shocked, staring at the sexiest sight I've ever seen. No wonder he doesn't date much, no need to if you can suck your own cock! I resume fucking Tyler with the dildo as he looks up at me, mouth full of cock and I stare back in awe.

"Tyler, uhh, that's so hot. Holy shit." I comment, full of awe and admiration.

"Thanks dad, I'm really thankful for this talent. I have the best sex and I don't even need another person to be present. But having you here working my ass is a welcome addition." He says as he plops his cock back in his mouth. He bobs on it, stretching further and filling his mouth a bit more with each pass.

I was so enthralled by watching him blow himself and fucking him with his dildo that I wasn't paying attention to what my phone was recording. "Hey Tyler, I think I should put the phone down, I'm not sure I'm that good of a cameraman." Hopefully I got at least a couple good shots.

"Sure, put it down on the table next to you. Make sure it's angled so that it gets the action on my hole and my face." He directs me, knowing exactly what kind of footage he wants. I reluctantly leave his dildo fucked ass to put the phone where he says and quickly return to my spot near his hole.

I grab the dildo with two hands this time, emulating the motions of churning butter as I really work it in him. Tyler's enjoying it and moans from my manipulations. My erection is threatening to rip through my pants so I use one hand to slide them down and take them off. Now in just a tee and my underwear, I feel a little relief.

"Yeah dad, get comfortable. Take all your clothes off." Tyler moans around his cock. I never thought I'd hear my son say those words to me, especially not with a mouth full of cock.

Not needing to hear it twice, I quickly slip my shirt off and tug my underwear down. It felt so good to be out of the confines of my clothes as my eight inch cock sticks straight out. "Oh yeah, that's much better." I say with relief.

"You look so hot down there dad. I love watching you work my hole." He says as he tugs on his dick and massages his balls.

My face was so close to his ass i could smell the sweet smell of his skin and the sweaty, earthy smell of his sex. Something was wrong with me to be so turned on by my son. I was even starting to wish it was my cock that was in his ass instead of the dildo I was using to fuck him with.

Now with one hand on the dildo and the other rubbing my cock, I confirm my eight inch cock is a little thicker and a little longer. "Is this dildo the biggest thing you've had inside of you?" I ask him curiously.

"Yeah, so far. The toys I've bought have progressively gotten bigger and this is the biggest one yet. I really like it, it feels so good, especially with you working it in me." He drops his dick and holds on to his butt cheeks, head tilted back enjoying the dildo in his ass.

"You're so hot! I mean, you're a very good looking young man." I say while watching his ass swallow this purple monster. "This dildos almost as big as my cock."

"Really?" His interest was piqued as he opens his eyes to look my way. "Lets see it." He grabs a hold of the dildo and starts working it so I can stand up in all my glory. "Holy shit dad, you're so hot too." He compliments me while fucking himself.

I smile down at him. "Thanks bud." I pull on my dick a few times, giving it a few long tugs.

"I mean it. I know I tease you for your age but you look damn good." I liked hearing him compliment me, even if he was working a fake purple cock in and out of his ass as he said it.

"Actually, this might be weird but, it might be pretty cool for the video if you put it in me." He shares his idea with me. "What do you think?"

"Yeah I think your dildos going to look great on camera." I agree with him.

"No dad, not that. Well yeah but I was talking about you. And your huge cock. It would really spread me open and give my videos some variety showing me get pounded. What do you say, dad? Wanna help me out a bit further?" He says as he removes the dildo with a noisy plop and his ass hole gapes, inviting me to plug it up.

"Holy shit. Really, Tyler? Would you be okay with that?" I ask for reassurance. I was really starting to enjoy helping Tyler with his new job.

"Oh fuck yeah dad, I'm so horny just looking at your big dick." He says as his eyes don't leave my cock.

"Okay but let me know if it hurts or you change your mind." I say as I don't want to cause damage, physically or emotionally.

"You won't have to worry about that at all." He says, full of lust.

I step forward and lean down a bit so my cock head is lined up with his asshole. "Oh fuuuuuck." We moan simultaneously as the head of my cock pops into my son's tight asshole. I easily enter him, his ass seemingly swallowing me into it. My eyes roll to the back of my head as my cock enters heaven.

"Oh daddy, fuuuuuuck mee." Tyler slowly moans as I bottom out in his most precious part. It was crazy seeing his legs still behind his head, I've never had sex with someone so flexible. I was so turned on as I slowly pulled out my cock to push it back in.

"Mmm Tyler, you feel so good. So warm and tight. Your ass is squeezing my cock so hard." His overworked ass still feels so good wrapped around my thick eight inches.

"Harder. Mmm. Smash into me." It was crazy hearing my son say these things to me. He sounds so horny, so desperate for cock and I was more than willing to give him what he wanted. He started sucking on his cock again and each time I slammed against him, more of his cock entered his mouth.

I start humping into him faster and faster until my balls are slapping against his ass, the sounds of sex filling the room. I pull almost all the way out before slamming back into him, pile driving into his hot ass. Tyler's moans are gutteral and incessant as I continuously abuse his prostate.

I have to slow down for a bit to put off my impending orgasm. Already my balls were tightening against my body, threatening to put an end to one of the best sexual experiences of my life. I couldn't hold out for very long before I get back to long, fast strokes. Pulling almost completely out before slamming all the way back in.

My breath gets shallow and i feel sweat trickle down my temple as I feel my impending climax building. "I'm gonna cum, baby. Are you ready?" I wish I could hold off longer but it's been so long since I've had sex and my son's hot hole was working overtime, squeezing me like a vice grip.

"Yes daddy, cum in me. Fill me up." Tyler says as he starts furiously masturbating beneath me. "I'm ready to blow too." He moans as his hole clenches around my cock with each spurt of cum shooting from his. Spraying his chest, he drenches himself with his cum.

His anal walls flexing around my cock set me off and I couldn't hold out any longer. My deep strokes slow down and stutter as I start flooding his guts with my seed. "Oh fuuuuuck." I groan as my balls empty into my son's accepting ass. The first orgasm I'd had in years that wasn't by myself and probably the best orgasm I've ever had.

My balls felt so empty, so relieved. I stay inside him a short while longer, my softening cock enjoying the confines of Tyler's ass. I slowly pump in and out of him, not quite ready to leave the comfort of his hot hole.

As we're both recovering from our climax I lay on top of him, squishing his smaller frame with my body weight. His legs finally dislodge from behind his head and wrap around my waist. I hold him in my arms as we enjoy the cum down from our mutual orgasms. What an unexpected day today turned out to be.

After a couple, relaxing minutes I break the embrace and look into Tyler's eyes. "That was incredible. Let me know if you need any more help with work, okay?" I give him a quick, tender kiss and get up to leave, my cock flops out of his ass leaving us both missing it already. I look down to see his hole still wide open and gaped, cum leaking out as it's slowly closing back up. I look in his eyes and give him a warm smile before heading for the door.

"Thanks for your help." He says and I turn to look at him, seeing him spent and used up. A hard day's work will do that.

I smile as I reassure him. "Anytime." I say as I leave his bedroom.

The next morning Tyler walks into the dining room while I'm reading the paper and drinking coffee. "Good morning dad."

"Mornin', son." I give him a warm smile, hopefully casually enough to cover up the anxiety and worry I was feeling over yesterday's events.

"I had a blast yesterday, well literally and figuratively. Thanks for helping me out." He leans in to hug me and then sits sideways on my lap. I couldn't help but remember how it felt inside of him. My own son. My cock started to remember as well as I hardened underneath him.

"Are you sure son, I would hate to have crossed a line we can't get back over." I ask, concerned I may have damaged our relationship.

"Dad, I really don't think that's be possible. I had a great time and I'm pretty sure you did too. There's nothing to feel bad or guilty about." He said as he slightly grinds his ass into me. My eyes roll back and I squeeze him a little tighter, trying to resist the urge grind back into him.

"Tyler, I'm your father, I don't know if this is appropriate." I try to cling on to the last bit of responsible decision making I had.

"Fuck appropriate, I want you to fuck me. A lot. I posted that video you helped me make and I got a lot of positive responses already. People are asking for a sequel, a lot of guys thought you were such a sexy daddy and that it was so hot watching you pound my hole. So what do you say, should we make this a family business?" He asks, inches from my face, his beautiful blue eyes piercing mine. I've never been good at denying him much, why start now?

It may not have been right what we did but it sure as hell felt good. And any good father would do anything to help his child succeed, right?

"Well, if it's good for your growing business, I should help and support you any way I can." I reply, caving in to my sweet boy's wild request.

"Thanks daddy, I really appreciate it." Tyler leans in for a hug and plants his lips on mine. Our mouths open and our tongues meet as a new level to our relationship begins to unfold.