Daddy issues

by Bill Drake

1 Jun 2021 4546 readers Score 9.6 (95 votes) PDF Mobi ePub Txt


Josh spent the first part of the week telling himself his hope of seeing Mr. Polo Shirt was silly. It was just a one-off hookup, and given the way Josh had acted impetuous with the guy, slutty even, he questioned where his head was.

Particularly since he found himself all Monday morning sneaking glances at his boss. Mike Richards. 52 years old, married, executive material. Not model-attractive, and in fact Josh had never even given much a thought about the man before, but that morning he found himself daydreaming, imagining holding onto his his boss's large hairy pecs while he bounced up and down on that drooling daddy dick....

Fuck, I've gotten out of control, the young man thought, trying to shake it off.

Work helped actually. There was a big project and three nights in a row he found himself working late. No time to think about Mr. Polo Shirt. Each evening Josh just got some take out, went home, watched an hour of TV, and then went to bed.

By Thursday, the deliverables were out the door that afternoon and Richards told him he could take off early.

Darren had asked Josh if he wanted to join a few folks for dinner later, but Josh declined. He wasn’t in the mood for a big group outing like that and just wanted to enjoy some time, alone in a crowd, as it were. He treated himself to a solo sushi dinner at the bar area of a trendy downtown restaurant, enjoying scoping out the happy hour crowd and nursing a drink. Not feeling ready to go home yet, he went to a beer bar in the neighborhood. A large cavernous indoor space unusual for Manhattan. It was still jammed with the after work crowd, a lot of Financial District bro dudes in their 20s and an assortment of pretty, thin, straight-haired 20-something women who went for that type.

As Josh stood and surveyed the crowd, he thought this kind of place would be his regular hangout if he were straight. As it was, he felt comfortable enough there, the guys reminded him of his high school friends and college teammates. There just wasn't much here for him. Not like for the dark-haired bro next to him with absolutely no game, for whom it didn't matter because the petite blonde he was trying to impress was hanging on his every word acted like he was Charming Charlie instead of a doofus.

There was one group of guys in there that stuck out. Not financial types, but dressed in a business casual uniform of slacks and polo or dress shirts. Older, jocky dad types in their 40s, if they were out of place, they didn't care or act like it. They laughed and were having a good time out. Josh looked them over and decided he'd pick out which daddy was the hottest. His gaze settled on one. Tall, broad back encased in a trim knit shirt, in shape waist with just the hint of love handles, big power ass.... round cheeks encased in a pair of navy wool trousers. Josh imagined those cheeks clenching, flexing, pumping while the guy fucked.

Then... fuck! The man turned his head. Mr. Polo Shirt had a shocked look on his face as he noticed Josh and after a split second recognized him. No doubt matching Josh's own surprised expression. The man's shock melted into a smile as he grinned and winked at Josh. The younger man felt the earth was going to open up beneath him, but he garnered his confidence and smiled back, raising his beer glass in salute.

Fuck, I've gotta go over and talk to him, Josh said to himself. But the man was with his friends, workmates maybe. Josh didn't have the guts to go over, especially now that Mr. Polo Shirt was back talking to his buddies, facing away from Josh again.

Josh looked down at his nearly empty beer glass. Maybe some more liquid courage would help. He polished off the last half-inch of beer and sidled up to the bar, squeezing in to catch the bartender's attention. Damn, the place was crowded now.

He hadn't waited two minutes when he felt a strong hand clasp on his shoulders.

"Here. Let me buy you a drink." That familiar laid-back tenor. If it didn't bring a hardon to Josh's prick, the close contact with this man was gonna. The man happened to catch the bartender's eye. "I'll have a pilsner," he ordered, "and whatever this gentleman's having."

"The same," Josh said, and soon they had two fresh beers. "Thanks," Josh said.

"Sure." Mr. Polo Shirt stood close. Not too close to raise any eyebrows, especially given the crowd, but it definitely felt intimate. "My pleasure. I'm glad I ran into you."

"Me too." Josh's eyes were now twinkling with desire as he looked into this man's gaze, unsure if he should say what was on his mind. Might as well. "Look, I've been hoping I could get a second chance."

The man raised his eyebrow. "Whaddya mean?"

"I think I fucked it up last time. Came on too strong. I'm not..." Josh felt embarrassed all over again. "Well, I was a little slutty when we met."

"'s all right... I mean, it did take me off guard at first. But I liked it. Spent all weekend thinking about it." Those steely blue eyes were doing a number on Josh as he spoke.

"Yeah?"

"You bet. I only wish.... well, I wish I could have asked you out. On a proper date."

Josh winced a little at hearing that, but his heart pounded, too. "Yeah, me too. Like I say, I fucked it up."

The man gave a little shake of his head no to reassure Josh and held out his him. "My name's Ryan."

"Josh." His face lit up with excitement, like a little kid with a new bike.

"Well, Josh, can I take you to dinner this weekend?"

Josh knew he had plans. He also knew he'd be canceling those plans. "Sure, Ryan, I'd like that."

The two exchanged phone numbers. Josh found out that Ryan's last name was Miller.

"You probably need to get back to your friends," Josh said matter of factly. Now that he'd found Ryan, the man who'd haunted his psyche this last week, he wasn't eager to see him go. Another part of him said this was for the better, that the date would make it worth the wait.

"They're my coworkers, but yeah, I should get back to them." He added, "One more question before I go. You more of a fine dining or a burger joint kind of guy?"

Josh shrugged my shoulders. "I like both, really."

Ryan clasped his hand on the younger man's shoulder, giving a gentle squeeze. "I wanna take you out of a really nice meal. My treat." He leaned in, so close that Josh could smell the musk of his cologne. His mouth next to Josh's ear, Ryan said real low. "Least I could do to pay you back for that amazing blow job."

"All right," Josh laughed as the man gave one last squeeze of the shoulder and made his way back through the crowd, leaving the 23 year old to watch the fine, power dad-butt as Ryan Miller walked away.



*

Ryan insisted on buying the round of drinks at the restaurant bar before dinner. "What'll you have?"

Josh decided on beer instead of wine or liquor, since he didn't want to get too buzzed. He watched as Ryan leaned over to talk to the bartender. Damn, this man made him hot. He'd dressed in a blazer, no tie, even so, it was like Ryan Miller had transformed. Looked like a perfect specimen of clean-cut executive, with just a little extra beefiness puffing out the chest of his dress shirt.

Apparently the man liked the slim-cut suit that Josh wore. Josh was a little muscular for it and always felt a little self-conscious in it, but it was the style for younger guys and besides, he had flat abs and a perfect bod, might as well enjoy being able to wear something like this. As they talked Ryan's sea-blue eyes would occasionally rake over Josh's body. He felt even taller than his 6'4".

"Cheers." The men clinked glasses.

"So," Josh asked. "What do you do for work?" He realized that up to now the two hadn't even made the normal small talk.

"Sales. Sports supplements, actually. I used to play baseball."

Josh's eyes lit up, partly surprised to have his suspicions confirmed. Ryan Miller really was an ex-jock "Really?"

"Yep. Pros and everything. Had a promising career in my 20s, never quite performed after that, and ended up on the DL for half of my last season before they declined to renew my contract."

"Who'd you play for?"

"Started off with the Astros, but spent much of my years with the Giants."

"I thought I could detect a California accent," Josh said.

"I was born and raised there, too. Bay Area. Being able to play for the Giants was a dream come true."

"I'll bet," said Josh. "You know, my dad was a professional athlete."

"No shit?" Ryan was surprised and there was a noticeable change in his body language, going from polite small talk to an immediate sense of real connection.

"Yes, sir. Football, played 7 years for the Broncos before retiring to Florida."

"That's cool."

"Yeah. Well, it's a mixed bag really. When you're young it's really cool being Mike Carter's boy, everyone in your class looks up to you and asks you to parties, and the town basically gives your family special treatment. I was REAL popular in middle school and high school."

"But..." Ryan prodded, sensing more.

"But it sucks trying to fill those shoes. And I tried to. Played ball and practiced till I couldn't practice any more. But I'm not going to be Mike Carter and that's OK I guess. Fuck... this is our first date and I'm already blabbing about my family issues."

Ryan patted him on the back. Josh liked this man was touchy-feely, it felt like having a big brother figure telling him everything was going to be OK.

"No problem, big guy," Ryan said. "I wanna know more about you. It's nice to have the chance to talk. You know, that night we first met... I thought you were still in college."

Josh gave a surprised laugh. "Yeah?"

Ryan blushed. "Yeah. I mean, you're big, like a jock, but you look young. If you don't mind my asking.... how old are you?"

"23."

"Wow."

"What?" Josh was nervous. "Too young for you?"

Ryan exhaled, "My friends would think so."

"You listen to your friends?"

"Probably too much. Listen. Fuck ‘em," Ryan said, getting his previous mojo back. "I'm out on a date with the hottest guy in Manhattan."

"I live in Brooklyn," Josh quipped.

"All right, the hottest guy in Brooklyn, then." He took a sip of his drink, then spoke. "Listen, feel free not to answer this, and you can even tell me to fuck off... but you generally date older guys?"

Sheepishly Josh nodded. "Yeah. Though to be honest, I've never gotten to the dating phase. This is the first time, really. I've always been afraid of what my friends will say, too." He paused. "Can I ask how old you are, Ryan?"

"43. Got my 44th coming up in a few weeks."

"Nice," Josh said.

It might have come out patronizing, but instead Ryan could tell he meant it as a genuine compliment. "You really like us old dudes?" he asked with a self-deprecating air.

"If they make them like you, hell yeah," Josh, "a lot of young guys would line up for a chance with a daddy like you." He saw Ryan flinch a little. "You don't like the D word?"

"It's OK," the ex-jock said, "It is what it is. I just don't always see myself that way. As a daddy. I think in my mind I'm still that regular fun-loving guy in my 20s. Maybe that's why I go for younger guys, cause I find that energy a complete turn on."

Josh took his turn to clasp his hand on Ryan's shoulder. "Look. Let's forget about the age thing for the moment. You're hot, period."

Ryan smiled. "Wise words, for a kid who looks like he could be a college sophomore." He winked. "You know, it wasn't until I saw you out Thursday that I figured you had a job."

"The way I was dressed?"

"Yep. Finance? Advertising?"

"Finance. Assistant Market Analyst."

"I'm impressed."

"Don't be. It's a made up bullshit title. Pure entry level."

"You're twenty-fucking three. Of course you're gonna be entry level. You guys today are so impatient."

Josh shot him a playful glare. "And you guys are always patronizing."

"Maybe. But I'm right on this. Unless you're in baseball," he winked. "In which case thirty-five is over the hill."

"Was it fun?" Josh asked.

"It was a job and real hard work. But yeah, it was a blast. I miss it." Ryan looked at his watch. "Our table should be about ready. Shall we?"

*

The end of the evening had been perfectly chaste. A little tongue in their goodbye kiss, which lingered for a good minute at the entrance to the F-train. But the two men said good night and went their separate ways.

Josh knew he had a dilemma on his hands. He wanted to spend time with Ryan again, and soon. But he knew he couldn't be too clingy. Couldn't rush this. Hell, maybe the guy wasn't ready to date a 23 year old. Or maybe the problem wasn't Ryan, it was Josh's fear of telling his friends. He imagined showing up with Ryan to a dinner or a party. Hell, maybe nothing would be different. His friends weren't dicks after all, even Darren deep down. But it meant Josh would have to be open, upfront, admit to himself and others the daddy fixation he had. Something about it embarrassed the young man.

He was running a million issues through his head but when he stepped out of the subway in Brooklyn a message awaited him. Ryan. "Had a great date with the hottest guy in Brooklyn. Hope we can do it again?"

Josh excitedly typed out a response. "Yessir, would like that. TTYL"

The young man felt aroused as he settled into this empty apartment. He rubbed his prick in his slacks, feeling it firm up. Man he would have loved to be doing it with Ryan Miller right now. "Patience, my friend," he said aloud to his now hardening cock.

Then, getting an idea, he opened his laptop. A couple of Google searches and he found what he was looking for. Pictures of Ryan Miller in his ballplaying heyday for the Giants. Josh actually preferred the 43 year old version to the younger man in the pictures. Still, he had to admit that Ryan was one hot looking player and that the uniform accentuated his looks even more.

He pulled up one photo, and enlarged it. Ryan at bat. His torso twisted in pure power-hitting pose as his bat connected with the ball. Josh unzipped and pulled out his cock, hard and angry now. He gave a quick spit or two into his palm and started a quick JO on his tool.

"Fuck man," he said, again aloud. "You wanna be my daddy? Show me what I'm missing? I'll suck you off, dad, just like before. Even better. Your dad spunk shooting into me, down my throat. Oh fuck me, Ryan. Fuck! Fuck!" Josh's body seized rigid and thick jets of white cum splashed on his laptop and coffee table.

He caught his breath and wiped up the mess. Leaning back he exhaled. "Josh my man, you're a fucking perv," he thought.

by Bill Drake

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