Glory Hole Star to Boss' Pet Pt. 01

1

23 year old Peter hated his corporate office job. His boss made his life a living hell and his coworkers were no better. He finally exited the office at 8pm, despite having gotten there at 8am. He was spent and emotionally drained, but he wasn't going home quite yet.

There was only one thing that could help him decompress and ease his stress, and tonight he needed it bad. He dropped to his knees in the booth. He was fully nude, for some reason that made him feel dirtier. He heard the door open on the other end and hoped to god it wasn't another another confused cocksucker going in the wrong side. He'd been that person before, he understood, but he was hungry.

Peter put two fingers through the hole, beckoning the anonymous individual on the other side forward. Before long, a semi-erect cock poked through. He sighed in relief as he took the head in his mouth. He liked going hands free at first. He figured that the guy on the other side liked it too.

He moaned to himself as he wet the dick and started accepting it into his throat. He was gripping the shaft now, slightly stroking it as be bobbed his head. He'd been coming here for a year and a half now and was pretty good. He had lost track of how many blowjobs he'd given, but it had to be well over two hundred.

Peter knew the guy was close. He was disappointed it would be over so soon, but he didn't draw it out. He knew the guy wanted to cum and he respected that more than anything. He took him all the way, his face rubbing against the curves in the hole in the wall as a hot load flew down his throat.

A muted "thanks" came from the other side as the cock withdrew. Peter didn't answer,  he never did. He had grown considerably less cautious since he started doing this, but he still feared that someone would recognize his voice.

His own dick was hard, but he wouldn't touch it til he got home. Giving blowjobs was always better when he was hard as fuck. Plus, he was up for more.

The door clicked open on the other side and the situation replayed with a new cock. By the time he left, he had sucked four in total, which wasn't bad for a Thursday. He felt better already, forgetting all about work as he jacked his dick in bed while watching j/o vids.

After cleaning up, he settled in for bed and perused his usual sites. They were talking about him again. The one mysterious cocksucker who frequented the video store on 9th Street. Peter was somewhat of an unknown legend on these boards. He was good and could get guys off faster than their girlfriends and wives could.

He was a little unnerved about the fame. He didn't want to be exposed.  Still, it flattered him and kept him, and them, coming back for more. He never interacted on these sites. He just lurked, soaking up the praise.

Peter was a cowardly cocksucker due to his religious upbringing. He had wanted to try it for as long as he remembered, but was too timid to go through with it. So, he simply fantasized a lot until he moved to the city for work. His apartment was just a few blocks from a sex store.

He recalled how he had looked into the place, learning about the glory holes, all the reviews talking about how discreet it was. The first two times he visited, he chickened out. But on the third, with a little liquid courage, he had gone through with it. It was everything he imagined it would be and he was hooked.

He had visited many times since. It was his stress reliever. But not only that, it was simply his favorite thing to do. Some guys had sports and video games, Peter had sucking cock. He had friends. He'd go out for drinks from time to time. They all assumed he was gay, but no one brought it up.

His record was ten in one day. It was a Saturday, and he just hung out there most of the day, dicking around on his phone between visitors. But, most of the time he kept it to 2-3 per visit. With the exception of the city's sex workers, he probably sucked more cock than anyone else in the city, maybe the state?

He had been propositioned for more many times, offered money to go to hotels, asked if he took it in the butt. He'd simply put his finger through the hole and signal no. No one really pushed it.

Anal was something he really wanted to try, but was scared to do put himself out there. He fantasized about it sometimes in fits of extreme horniness, but never put anything up there. It seemed like a waste to him. He didn't suck dildos before graduating to cock. It was the real thing or bust. That's just how he was.

In any event, outside of the 12 hour day, Peter was annoyed and anxious about a business trip next he week he was being forced to go on with his boss, Wilson. Wilson was 55 with graying hair but still in great shape. A real Alpha type blowhard who shouted orders and criticism and never let up.

He wasn't really any different from any other macho in blowhard corporate boss, but this was the only one Peter had experience with. He made Peter uncomfortable with his abrasive style and insistence on putting his hand on Peter's shoulder and looking him directly in the eye when they spoke.

Peter did find him attractive and fantasized more than once about sucking him. Hell, he'd fantasized about most of the guys in the office one time or another. Still, his Wilson ones were hottest. Just something about how he made him feel.

He had absolutely no expectation or hope anything would happen. Deep in the closet, he feared it! Plus, seperate hotel rooms. They weren't even sitting together on the plane. That asshole was gonna be riding first class while Peter was in coach.

The next day was equally grueling but he made it through. Knowing he'd be out of town next week and not knowing the "scene" of the city they would be in, Peter gave twelve blowjobs over the weekend. He would have happily given more, but it was slow.

The chaffuered ride to the airport and subsequent flight were awkward but bearable. Wilson exchanged pleasantries with Peter but banged on his laptop and took calls the entire time. Peter was simply there in an assistant capacity.

They checked into their rooms and almost immediately booked into a full day of meetings at corporate HQ. It was incredibly tedious and filled with corporate jargon and passion that Peter couldn't care less about. Still, he diligently took notes, produced statistics when asked, and chimed in when appropriate.

Peter's research into the "scene" here had been disappointing. This state was a lot less open minded than his. The boards and sites he frequented referenced a big hook up culture, and the sex shop reviews all made reference to boothes being removed after some city ordinance passed. It was going to be a long week. He honestly couldn't remember the last time he went that long.

He was pretty wiped by the end of the day. He casted some j/o vids to the hotel tv and laid around naked, stroking aimlessly as he watched cock after cock cum. Peter, surprisingly, didn't care for blowjob porn. He had no interest in watching someone else do what he wanted to do. It was pointless. Still, in the absence of being able to suck one, he loved watching a guy solo go from soft to hard and then blowing his load everywhere.  He'd heard this was the type of porn chicks really got into and he understood completely.

It was around 9.30 pm when his phone chimed. It was Wilson, telling him, not asking, to come to his room with his laptop to go over tomorrow's agenda. Peter considered pretending to be asleep but knew Wilson would come knocking like an asshole.

Sighing as he turned off his videos, he got dressed and took the elevator to Wilson's floor. On the ride up, his phone buzzed again.

- Pete, stepping out for fw mins. Door propped opn. Get Q3 stats plld up.

Peter rolled his eyes at the boomerish and unnecessary abbreviations. Did this guy not have auto correct?

As promised, the door was propped open. Peter planted himself in a chair and got the docs open.

2

Wilson had perversions of his own. Funnily enough, he had stopped by the sex shop many times and gotten his cock polished by Peter. Both were oblivious to their already intimate history.

Bored by his wife's lower sex drive and lack of imagination, he'd gone looking elsewhere. Cocktail waitresses, secretaries, sex workers, the whole gambit. He figured that the person on the other end of the glory hole was a man but that wasn't anything new for him. 

He was clumsy setting up one particular hook up profile, not specifying what gender he was interested in. Spending the better part of an afternoon clearing out multiple requests from horny fags his own age, a few from college aged guys wanting to experiment caught his eye.

A few days later, he was balls deep in one of them. Wilson was interested in sex, not emotional needs or lasting relationships. This had been an issue with many of women he had bedded. So, imagine his surprise when this 20 year old university student sucked him, took him in the ass, sucked him again, thanked him and then went home smiling. He decided to make a separate profile for men, specifying his wants and was rolling in college ass whenever he wanted.

He KNEW Peter was a gay bitch. He couldn't explain how he knew, it was just a very strong feeling that defied the lack of any evidence. No doubt, he had tried to gather some, cyber-sleuthing and coming up empty handed. Unwilling to simply come onto him and cause a fracture which saw his last secretary bail, he sought proof instead.

Getting an extra key to Peter's room had been easy. His corporate card paid for it. They didn't bother to question the request at the front desk.

Following his text, he had watched from the hallway as Peter got on the elevator, entered his room and sent the second one letting him know he would be late.

Wilson fixed small hidden cams throughout Peter's room. One pointed at the bed from the TV, one in the light over the bed, and finally one above the shower.  Voyeurism had been a relatively new fetish for him. A risky one for sure, but that just made it more exciting for him. In all, he had been there for less than 3 minutes.

Whistling as he entered his room, he thanked Peter for his patience.

3

Peter did a double take as Wilson had just seemingly been walking the halls of the hotel in a robe. He guessed it wasn't THAT weird, but it made him feel a little uncomfortable.

Wilson sat down and feigned interest in the documents he had Peter pull as a distraction.

"OK good, great. You did good today, know it's a lot, but we gotta keep up the stamina" he said, touching Peter's arm.

"Care for a drink before you head back?" He added.

And then it happened, all according to plan. He wanted to give his employee a little taste. A plausible slip.

Without waiting for Peter to inevitably decline the offer, he pushed back in his seat, straining his arms to fetch a bottle of whiskey and two glasses. The movement forced his robe to part and, since he ditched his boxers for the plan, his flaccid cock was on display for a few seconds.

His motion back to the table covered it back up, just as he had practiced and he did not acknowledge it or act any differently as he served  them both a hearty pour.

"You want some soda or something as a mixer?"

Oh boy was Peter a ball of nerves. He had, of course, seen it. He liked what he saw. For all he knew, it had been an incredibly careless yet honest mistake. Composing himself best as he could, he accepted the soda and kept pace for the duration of the excruciatingly long encounter as he got tipsy.

Excusing himself, he went to relieve himself in the bathroom while Wilson quickly connected a contraption to Peter's phone, tapped a few keys on his laptop, and grinned as a confirmation light beamed. Everything was back in place by the time Peter meekly said he had to head back.

Wrapping up, Wilson gave him an extra bottle and some mixers in a bag to go.

"In case you want to keep the party going on your own" he laughed as he patted Peter on the back.

Peter walked back to his room quickly. He had tremendous experience with cocks, but seeing his boss' hog two feet away unobstructed by a wall was really getting him hot.

Locking the door behind him, he quickly ditched his clothes and sprawled out on the bed.

Wilson, meanwhile, laughed to himself as he watched his employee pull hard at his five inch penis. He felt an absurd amount of pride, clocking Peter for exactly what he was. He stroked his own to its nine inch length as he pondered his next steps.

Peter climaxed hard and quick with Wilson's cock on his mind. He made himself a drink and unlocked his phone.  He went to a subreddit he routinely posted in for sexually active closeted gay dudes. Wilson watched in real time as Peter typed out the saga.

"On a business trip with my boss..."

Peter typed out how excited it made him and how he had rushed to his room to rub one out.

It wasn't long before he had responses. Each doubted it was an accident. Inevitably some posers, who had likely never done anything, said they would have just grabbed it and sucked it. Peter rolled his eyes as he responded to some people, down voting others. Some posters he was friendly with opined that this was his origin story for ditching the glory hole scene.

"Never!!!" He jokingly replied.

Meanwhile, Wilson noted Peter's username and scrambled to create his own account. Pouring another drink, he kicked back and read his employees full history of sexual perversions.

4

He laughed heartedly at posts where Peter lamented his boss putting him in a bad mood and how he had spent hours on his knees as a form of therapy to get over it. There were only so many places like that back home. He wondered if he had perhaps already been blessed by Peter's mouth. Still, he found it hard to believe that this guy was sucking as much cock as he claimed.

Moving on, he was surprised that Petey had never taken so much as a finger up his ass despite wanting to. He poured over the anxieties he had about being openly intimate with another guy. Wilson didn't really get it, but acknowledged that this may be harder than he thought.

The rest was more or less the same. He was kind of annoyed at the enigma of an obsessive cocksucker who only felt comfortable in glory holes and was too much of a coward to take it up the ass. Oh well, he thought, he knew more now than he did at the start of the day. His dick swelled at the prospect of getting a crack at Peter's virgin ass.

5

The next day was more or of the same work-wise. Mentally,  Peter was electrified and could not stop thinking of Wilson's dick. Even flaccid, it looked meaty and impressive.

He spent his lunch break on Reddit, chatting with a few dudes and turning down their pic requests. A message request popped up and he swiped to it.

"Very hot story. Like the others on the board,  I doubt it was accidental but I get why you wouldn't just jump on it. If you really want to push through your insecurities and test him, I have some advice."

No, this was not Wilson messaging.  It was a guy Peter chatted with pretty frequently. 

"OK, I'm game" Peter replied, unsure of if he really was.

"If he invites you back to his room again, I'd say it's probably a pretty clear sign he's interested. You said you don't think he knows you're gay. You're going to have to give off some sort of sign."

Peter tensed up. Having never come out to anyone, this seemed out of bounds.

"Just some ideas. They may sound stupid. They probably are. Maybe you go and buy some pants that are a little tight to show off what you got. Any excuse you get near him, bend over so he gets an eye full."

"If he wears the robe again, it's another good sign. Pretend to drop something

so you get down there on your knees."

"If you're drinking a bottle of beer, absent-mindedly nuzzle the bottle against your face. Maybe take more of it in your mouth than you need to."

Peter felt himself getting hard. He responded, "no offense, but this kinda sounds like rom com stuff..or even softcore porn stuff lol."

.

"Listen. You obviously have hang up about telling people irl you're gay. Outside of that, you need to throw him enough hints where he'll feel comfortable reciprocating.  He's your boss, he has leverage...but you also have leverage.  He's not gonna go blabbing to everyone about how he's banging you unless he wants to out himself."

"Look, man. We've been talking for ages. There's so much more to this than sucking through a wall lol. Are you going to get a better chance than this?"

Peter's thoughts raced frantically. There was a weird, totally insane logic to that this guy who had initiated the conversation with a dick pick one year ago was saying. And, truth be told, Wilson exposing himself had given Peter a strange sense of courage.

Checking his clock, be realized he had just enough time. He darted into Target, picked up a pair of yoga pants a couple sizes too small, sandwiched it between some normal cheap shirts, and hit the fitting room.

He hadn't really paid much attention to his own ass in the past. The idea of it being used for sex had seemed so remote. But damn, it looked good in these.

Hitting self checkout, he paid for the pants and the two shirts he rolled them up with, making it back just in time for the resumption of the meeting. It was more of the same and ended with Wilson heading out for drinks with an exec. Peter felt pangs of disappointment and was second guessing everything.

6

Wilson pounded a few beers with the exec but was happy when the evening was cut short. He had read over Peter's exchanges and he knew could at least have him on his knees tonight. Buzzed and incredibly horny, he changed into his robe and sent Peter a text telling him to come over for another debrief.

Peter had already written off the night, thinking that nothing would happen. He was drunk, watching jo videos like normal. He saw the text and nearly tripped over himself to dig out the yoga pants. Liquid courage or not, he was incredibly nervous and forgot to factor in that he'd have to walk the halls and ride an elevator dressed as he was.

"Hurry up" another text read. Peter's dick got hard and he frantically tucked it as best as he could. He tied his coat around his waist to cover his bubble butt, drained the rest of his drink and steadied himself. This was the biggest step he had taken since that first time he blew a guy. It was a bigger step. Anxious, his horniness propelled him up to Wilson's room. Thankfully, he didn't bump into anyone.

The door was propped open once again so he let himself in. Wilson was sitting in his robe once again. Peter wanted him bad. Unable to make eye contact, he walked over and in his awkwardness accidentally knocked the TV remote off the TV stand.

"Now or never" he thought to himself at this gift of fortune from the slut gods.

"Oh, oops, I'll get it" he mumbled nervously as he removed his coat and placed it with his laptop bag near his chair.

The remote had simply fallen a foot away from him. Instead of crouching down, he turned so his ass was facing Wilson. Bending at the waist, he bent over to get it, taking a few seconds longer than necessary.

Wilson's cock tented his robe. Peter's ass was designed to be fucked. There were ways he could have handled this, but the drink and his advanced knowledge of Peter's wants and intentions threw the playbook out the window. So, when Peter turned back around he was greeted with Wilson's hard cock fully exposed.

"You wear those pants for me, boy?"

Peter was stunned at the quick escalation, having expected more of a drawn out play. He couldn't take his eyes off that big dick that was hard from Wilson simply looking at his clothed ass.

"Y-yeah" Peter replied.

"Good, I thought so" Wilson said, standing up and letting his robe fall as he walked behind Peter. Grabbing him at the waist, he ground his hard cock into Peter's ass.