This story is completely fictional. This is a story about adult sexual relationships between a man understanding his role as a Daddy for younger men. If the nature of the story offends you, or if you are under the legal age to view this content, I ask you not to read this. If you have any questions, comments or criticism, email me at loverboystory28@gmail.com.
I had my assistant up against the wall, his face pressed against the plaster as I held him from behind. Undoing his belt, I let his dress pants fall to the floor and grabbed my prize, his soft young ass was like putty in my hand, and with every rough smack, he moaned louder.
" Do you like my ass Mr. Schwartz? " He said, his face still scrunched against the wall.
" You know I do, I've seen you trying to get my attention, but just looking won't get me off, I need a little more than that. "
I slid my hand between his firm ass cheeks and rubbed his hole, my gentle touch at odds with my animalistic desire. His hole was tight, and lubed, Mike laughed to himself, as his assistant had clearly planned to entice him into this situation, and a new wave of lust came over him, he could not wait to fuck him, to be inside of him, to make the much younger man moan and sweat before the night was through.
Terry was his shadow at the firm, as his secretary and assistant he was constantly at Mike's side, an nineteen year old boy, he was only in his second year of college and twenty years younger than his boss. Mike let him work for him in part because he was the child of one of his associates, the other because he was a good worker. It was only once he started working as his aide that Mike realized that he was gorgeous, a boyish face with soft brown eyes and the clean haircut of a young professional, Mike was happy that he had a bit of eye candy to look at while he was working, it kept the work-day interesting.
But it did not stop there, a few months into working with him, Mike noticed something different, Terry began to come into his office more and more, looking for any excuse check him out. Mike could not remember how many times Terry walked in and would start to undress him with his eyes, first sizing up his arms, and then his chest and then his face, occassionally one days when Mike would not shave he would linger just too long on his five o'clock shadow and give himself away.
At first Mike was flattered, a young hot thing like Terry could have any man he wanted, and it boosted his ego a bit to know that Terry wanted him. It was a little spring in his step and made every day at work a little more exciting. Before long he was calling Terry back and forth, watching the young man bite his lip at the corner of his mouth everytime he handed him a document or told him to print something, flexing his upper body to the youth could get a nice look.
Looking back, Mike knew it got out of hand when he decided that he would not wear his boxer briefs that morning, in his younger days he always had the problem of too much bulge, the way his dick rested against his balls would created a lump in his pants no matter what he wore. He learned early on he needed to do everything but tape it down to keep everyone's eyes off his crotch. Boxer briefs had just become fashionable thanks to Calvin Klein, and he found that they hid everything in a still noticeable, but much less distracting bulge.
In just his dress pants, his dick pushed against the fabric and created a particularly obvious outline that Terry could not miss. Looking at himself in the mirror, he liked the way his dick bounced from one side to the other when he walked, the large head would especially enticing, he thought. That day at work he walked over to Terry's desk instead of calling him in, walking with a swagger he had not felt in years, his fingers tingled at the thrill of seeing Terry's response.
The young guy's eyes nearly fell out his head watching his boss's cock moving in front of his very eyes. Mike stopped right in front of him and handed him some nonsense paper, his junk sitting right in front of his assistant's eyes. At this distance, Terry could see everything, the crown of his dick, the sizeable shaft that hung lower than his balls even when soft, the noticeable thickness that made his cock a literal mouthful and a pair of two hefty balls that swung with every step. Terry almost reached out and touched it, but he held himself back with the kind of determination that Mike had never knew, when he was done he walked away, his heart racing and his cock quickly stiffening in his pants.
He had not expected anything more than that, but the next day Terry had managed to raise the stakes, while Mike was in the bathroom, his assistant followed him in. While Mike was standing there taking a piss, Terry came up right next to him at the urinal, making pretend conversation while he took an obvious and thirst-quenching look at his boss's cock. Pulling his pants down, Mike's mouth nearly dropped when he saw the boy's naked ass fall out of his clothing. He was wearing a tight jockstrap, his entire backside was uncovered and clear for Mike to see. It was round, a nice perky bubble butt that Mike could grab entirely in his hand if he wanted to, it was framed by two rosy pink dimples on either side of his hips.
His eyes told Mike that he should touch it, and he almost did if not for the another one of his workers walking in at the worst possible moment. Terry quickly pulled up his pants and Mike had to fish his boner back into his before the man noticed.
They had finally reached an impasse later that day, Mike told Terry that he would be working late getting some much needed work done, and almost immediately Terry agreed to stay behind with him in order to input some future appointments into the system. As the last worker left for the night, and before the janitor's started cleaning the building, Mike knew he had a firm hour with his sexy assistant. He called Terry into his office, and his secretary was at his door before he could even finish his sentence.
" You wanted to see me sir? " Terry said, playing the part of the young ingenue, unaware of his boss's desires.
" Yes, Terry my boy, Valentine's Day is coming up, I wanted to know if you could get some flowers sent to Paul for me. " The name of his longtime boyfriend had dropped from his mouth, until now he had almost forgotten it, and even now it seemed a bit hollow.
" Yes sir Mr Schwartz. " Terry said, almost downtrodden that something more did not happen. As he left the room, I grabbed his hand.
" Tell me Terry, do you have anyone special you wanted to send something for Valentine's Day? "
" No. No sir, I haven't had the time to meet a guy, I spend most of my time working here or going to class. "
" Really? How does a young man like you not have guys begging to take you out? You're a catch. " Mike positioned himself just right, leaning against his desk so that his cock and balls sat alluring against his thigh, immediately his assistant's eyes fell on it.
" I'm not really into guys my age, there's a man I've had my eye on, but he hasn't made his move yet. " Terry said, shrinking into himself, hoping that Mike would bite the line he was reeling out.
" Men? I never pegged you the type to be interested in older men. " The bulge in my pants was growing larger, and Terry did not fail to miss it.
" Yah, I have this fantasy. A boss and his secretary. " The bulge in his pants was growing too.
That moment I exploded up, startling Terry. When he regained his senses, I had my arms all over him, one holding his head, while the other was holding both his ass cheeks in my hand. Up close I finally noticed how much smaller than Terry was than himself, half a foot shorter than me, I could wrap him up in my body, my size dominating his.
He relented, he let his body fall under Mike's control as he pushed him against the wall, undoing his pants. Sliding his pants around his ankles, Mike pressed his dick up against his assistant's hole and heard him suck in his breath.
" Do me right here sir, I want you to fuck me. "
Mike pushed his assistant's ass out with his hand and slid into him, at first there was a bit of resistance as his asshole accept his intrusion and he was able to feel the warmth of his assistant's asshole ans it enveloped him. Just the right amount of tightness without hurting either of them, he was able to start a good rhythm, sliding his thick cock in and out of his asshole. Terry was pleased, offering nothing but grunts of approval as he pushed back against the wall, his ass taking so much of Mike's dick that he could feel Terry's ass against his pubes.
It had been months since I had sex with anything other than his hand, Paul was always so busy with his work that would not even think of fucking him. He needed an ass to fuck badly, and since Terry was more than willing, he could not hope to turn him down. He was not even thinking anymore, he was just satifying his urge to cum.
The entire encounter was short, but in Mike's head it lasted forever, pounding a hot young piece of ass, bareback, without any thought to the consequences was more sexually satisfying than the act itself. A few minutes into the pounding he was giving Terry, he busted his load deep inside his ass, the first time in months. Terry yelped when he felt the first burst of cum hit his insides, but he continued moaning as Mike filled his hole up.
Mike had forgotten how good it felt to fuck his load into a man's ass, and even though he was spent, he hungered for more. He felt himself go soft and his cock fell out of Terry's ass, the head of his pole slick with the cum that he had just unloaded into his aide. He wiped his dick on his boxer briefs as he pulled his pants up, redressing into his formal clothes while Terry cleaned himself up.
" Thank you sir. " Terry said, stuffing his dress shirt back into his pants. " I've wanted you to fuck me since I was 15. "
" You are a cute kid Terry, how could I say no? " Mike said, wiping the sweat from his brow, the room was beginning to cool down and high from the sex was giving way to contemplation. " Now how about you finish putting the my appointments into the system? "
" Yes sir. " Terry said, walking a little stiffly from the Mike's office, before closing the door, he looked back in to ask Mike something. " Can we do that again sir? "
" Of course, do a good job and you can come here every night for your reward. " Terry closed the door behind him and Mike sat back in his chair, playing the entire experience back in his mind, he thought he would feel guilty, but he didn't.
His fun did not last forever. Every week or so, Mike would stay late and have Terry service him, either by fucking him or having his secretary blow him while he worked. Most of the time Mike was putting his cock down Terry's throat, it was quick and all the mess was gone when Terry swallowed it. It was during one of these occassions that Paul had come to his work, hoping to surprise him, needless to say it was like a bomb went off in his office.
The next few months were whirlwind, by the end of it Paul was gone and Mike was living alone in the house they bought together. It was a ugly breakup, but Mike felt it was for the best, lately he began feeling his ex-boyfriend's lack of a sex drive and financial needs put a strain on their relationship, and Mike was beginning to realize what he needed was to be single, date around and to better understand his own life. Ultimately he felt like he grew from the experience, and his newfound freedom was a godsend.
Now he was single again, he did not know how to go about meeting guys, before he met Paul there was no such thing as social media, and the only way to truly meet another gay man was to meet him at a bar somewhere and take him on a date. Mike was uncomfortable with the idea of using one of those apps to find a guy, and he preferred meeting someone face to face.
One night he found himself stopping by a local gay bar, it was much more of a dive than a nightclub, and a lot of the men who went there were about Mike's age or older. He sat and had himself a drink, not really feeling up to putting himself out there just yet. The bar was quaint and the patrons seemed friendly, and right around twelve in the morning, things got more interesting.
Several young guys has entered through the front door in a large group, a smattering of ages between eighteen to twenty three, the bartener chuckled to himself and just as Mike was about to inquire further, he answered.
" Watch out newbie, the Daddy's Boys are coming. Better watch your wallets. "
" Daddy's Boys? " Mike asked.
" Yup. Young guys who date men old enough to be their fathers. They like a guy who's a little bigger, rougher, manlier. Like I said, watch out newbie, a guy like ends up pretty popular around here. "
He was not lying, not even five minutes later he was being chatted up by what he suspected was an eighteen year twink, blond hair and blue eyes not even peache fuzz on his face. In nothing but a tanktop and short-shorts, his slender frame was more than enough to get the guys in the bar jealous of Mike.
" Hey Daddy, want to buy me a drink? " He said, luscious pink lips standing out in the dimness of the bar.
Mike felt a little odd about the use of the word 'daddy', Mike had never really heard it used outside of the ordinary context of children talking to there father. He tried not flinch at the sound of it, but it did sound odd, to hear the word in an entirely sexual sense.
" I'm not sure I can buy you a drink, how old are you? "
" Old enough to know what I like. " He said, taking his index finger, he ran it through Mike's beard and stopped it on his lips. His fearlessness was appealing, as was his body; Mike would not hate for a young guy like him pursuing him.
" Normally I would say no, but for a sexy thing like you, I think I can make an exception. "
Ordering him a drink, I nodded to the bartender for him to water down the drink a bit more, and wordlessly he agreed. When the drink came over, the kid drank in down in seconds.
" I'm Mike, what brings you here tonight? "
" Sammy. Me and my friends like to come here, the bartender doesn't mind if we come in on the weekdays, and truthfully, I just come here to meet hot daddies. "
" I was never that daring when I was your age. I could barely even talk to a guy, much less pick them up at bars. "
" Yah, I'm just daring I guess. " Sammy reached for my hand and guided it to his chest, smooth and hairless. " What are the chances of you and me getting a little daring tonight? "
Taking the lead, Mike began to inspect his chest on his own, the younger man was more skin and bone than muscle, but it was the difference in their body types that made it all the more erotic to Mike. He was just a step from his prime, and had a little more pudge in the ordinary places, but more and more he was beginning to realize that he had a thing for younger guys, the idea of a big hairy man like himself in contrast to the smaller, younger guy got him boned up almost instantly.
" Pretty good, I would say. What do you like in your men? "
Mike started rubbing Sammy's nipple, gently, and Sammy softly cooed in response, placing his hands on Mike's thighs, trying to steady himself and enjoy the older man's touch.
" I want a rough daddy, the kind who will order me on my knees and suck him dry. Whenever, wherever. "
Mike's ears perked up, he could never say no to a good blowjob, and Sammy's lips looked like the kind that were built for sucking dick.
" How would you feel about going in the bathroom over there and getting on your knees? "
"Yes daddy. " Sammy said.
The two walked into the bathroom, passing by another pair who had been making out on the bathroom counter. Sammy lead him into one of the stalls and got on his kness. He was rubbing Mike's dick through his jeans, and Mike's fingers and legs were shaking the tiniest bit in anticipation for what was going to happen. He had never thought in his wildest dreams that he would be getting his dick sucked in a very public bathroom, other men so close to him that they would hear everything that was going on in the stall.
" Oh fuck, your dick is so sexy. "
Sammy had fished it out of Mike's boxer briefs and was lubing it up with spit, rubbing the entire length with both hands. Mike loved how the twink's slim fingers made his dick look huge, a modest six and a half inches long, he was never winning any awards, but it was his thickness, another six inches in girth that kept them satisfied.
The blonde twink wasted no time getting to work, having worked him up to full erectness, he tried to get the full thing into his mouth in one go, the thickness alone had his luscious pink lips struggling to fit the head of Mike's dick entirely. Curiously, it just made him want to suck on it more, and after licking his lips a couple of times, he managed to finally fit the head into his mouth. Soft and moist, Mike started pumping the shaft in and out of the young guy's mouth in a fast but steady pace.
In Sammy's other hand he worked Mike's balls, massaging them while he went further and further on Mike's dick. Once he had reached the base of the shaft he slid the entire length of the dick out of his mouth until he was sucking on only the head. Waves of pleasure flew from Mike's cockhead through his entire body, causing him to lean backwards and rest his body against the back wall of the stall. He laid there, watching Sammy work the head, working him up more and more until he continued the blowjob.
" Fuck. Keep this up and you're going to make me cum. Do you swallow? "
Sammy could only give a nod of approval.
" Oh right. Can't talk with your mouth full?" Mike said, chuckling to himself.
Sammy's response was a mixture of an agreement and a moan. Picking up the pace, the constant stiumulation was getting Mike close, really close. Unconsciously, he started rubbing his hands through the younger guys hair as he sucked, making loud gulping noises as Mike's cock worked the back of his throat.
" Fuck. I'm going to cum, swallow it, swallow it! " Mike gasped and pushed Sammy's head down further on his dick, the blonde-haired boy choking a little as Mike dumped a fresh load of semen down his throat. He held the boy there until his orgasm passed, and afterwards helped him clean up the leftover spit and cum that he still had on his lips.
" Thanks Daddy. "
" I should be thanking you, I haven't had someone suck me dry like that for some time. " Mike cleaned up his dick with a piece of toilet paper and exited the bathroom with Sammy following close behind him. The patrons cheered as they reentered the bar, evidently every single one of them could hear the sounds of Mike's blowjob all the way from where they were sitting.
They congratulated him on his 'initiation'; it was something of a tradition for new members of the bar to hookup with someone they had met the first night they were there. By the time the night was through, Mike had managed to make tons of new friends, and even score some numbers, before returning home, excited for the first time in months about what his future would hold.
Thanks for reading! This story is apart of a number of one-shots that I'm doing to in order to my name out there on Nifty. If you liked the story and want to read more, email me at loverboystory28@gmail.com