Gay Erotic Stories

His employees knew him as a high powered, take charge, no nonsense executive. Oliver was rarely if ever seen wearing anything other than a three piece suit. But no one in the office had ever seen him without a tie, which was always tied in a tight double Windsor knot.

Oliver didn't attend happy hours or company picnics. He was too busy for such things. He was stern and all business. There wasn't one employee who had ever seen him crack a smile. He did not joke and had no time for those who did.

He had created this image for the world to see--an image of a powerful successful businessman who was always in control. And this truly was one side of Oliver. But like most people Oliver had another side--a side that he kept hidden from most of the world. A side that he allowed only a few chosen few ever see. A sexual side. A kinky side. But today unbeknownst to him that side was about to be exposed to all of his employees.

As previously stated Oliver went out of his way to project the perfect persona of power and control. None of the employees who worked under him would ever guess that one any given day underneath Mr. Cromwell's Armani suit he could be found wearing a pair of stainless steel nipple clamps. Or that instead of a pair of neatly pressed conservative boxers he was wearing either a leather thong or a leather jock.

It was also inconceivable that anyone would ever guess that underneath his leather under gear firmly wedged between his ample buns was a 4" stainless steel butt plug. A butt plug that came with a remote control with ten speeds for various levels of intensity. And certainly no one would ever guess that wrapped around his extra large low hanging shaved nuts and ridiculously small dick was a sterling silver cock ring. And of course no one would ever guess that from the neck down Oliver was as smooth as a baby, having had all his body hair waxed off.

And Oliver liked things this way. He got off walking through the Savings & Loan with his vibrating butt plug turned on to a level 1. Allowing it to gently massage his prostate. He was an imposing figure and his presence struck fear into each of the men who worked for him. He got off on this knowledge. But he also got off on the knowledge that as he stood there intimidating his underlings his prostate was being manipulated and they had no idea of what was going on. But, today his secret was about to be exposed.

It was a Friday evening just five minutes before closing. Old Jasper stood at his post at the door in the exact same spot that he had stood in for he past thirty-five years. His cocoa brown skin not showing the signs of his fifty-five years on this earth. In the tellers cage was Robert (age 26) and the young blond twin; college intern, Jack (age19) that he was was training. And behind them was Raul, the 42 year old accountant who was just finishing up balancing the books. And in his office, behind closed doors, sat Oliver finishing up some last minute paperwork.

It was the Friday before a Holiday weekend so the Savings & Loan was working with a skeleton crew. Even the cleaning crew who normally came in every night had the evening off. Another five minutes and each of the men would head home to their families. Or so they thought.

Old Jasper stood at the door half nodding off, after all nothing out of the ordinary ever happened. But, tonight would be different. At exactly 5:56 PM two men wearing black ski masks came storming through the door. Both were waiving handguns. The taller of the two, whose name was Dan, ordered Jasper to lock the door and pull the blinds to indicate they were closed. Jasper fumbled for his keys and shaking did as he was told.

At the same time the shorter of the two men, whose name was Al, ordered the three other men out from behind the counter. He instructed them to line up in front of the teller window. By this time Jasper had locked the door and Dan was directing him to join the other three men in line. Old Jasper spoke first, "Look we don't want any trouble. Just take the money and be on your way. We ain't gonna fight ya."

Dan laughed, "I know your not gonna fight us old man. But we want you secured first. Now first things first. I want you all to strip."

"S-s-s-strip?", asked Jack, confused by this command.

"Yeah, strip,” barked Dan. "You’re gonna strip then were gonna tie you up and when we leave well take your clothes to stop you from following us."

Al laughed as Jack innocently and naively said, "Please don't make us strip. We promise not to follow you."

Dan responded to this by raising his gun and aiming it at the teen, "I said strip. NOW!"

With that the four men knew that Dan & Al meant business. Eight shaking hands began fumbling at belt buckles, loosening ties & unbuttoning shirts. They kept going until every stitch of clothing that every man had been wearing was lying in a heap on the floor. They were even made to remove their socks and underpants.

Each man was lightly embarrassed at being so exposed before his colleagues in this manner. Each man tried to cover his manhood with his hands but Dan wouldn't have it. "Hands at your sides he barked." Obviously enjoying the power he had over his four captives.

Each man dropped his arms to his side and both Al and Dan were shocked by what they saw. These men certainly had nothing to be ashamed of. Each man was incredibly well hung. It was as if they were part of some club for men with over sized endowments.

Robert's cock was thin but a good 8.5" limp. Raul's was uncut and slightly darker than the rest of his deep tan colored skin with an average thickness but was just over 9" limp. Next was Jack, the intern, with an amazing 11x7" monster, and once again that was flaccid. But leading the pack in both thickness and length was Old Jasper who was sporting a soft 13x8" dick.

Both Al and Dan were straight and got no sexual pleasure out of seeing these men naked. Though this was not the first robbery or either man. And they always liked to strip their victims partly to prevent them from following them and also partly to humiliate them. But there was nothing about these four men that was humiliating. What would they do insult them with taunts like "Your dick is massive." That made no sense so instead they opted just to tie up the group of horse hung men, grab the money and run.

Al pulled out four bent wood chairs from the waiting area and placed them across from the teller window. He placed them in two sets of two back to back and ordered each man to take a seat. Old Jasper and Jack were back to back and Robert and Raul sat back to back. Then Al worked on securing each man first to his own chair then he tied each chair to the one it was back to back with so that it would prevent movement.

Next Al gagged each man by using the underwear of his fellow co-worker. Al took Raul's red and white stripped bikini briefs and shoved them in Old Jasper's mouth as he opened it to protest. Then he secured them in place with duct tape. Likewise Robert was gagged with Jack's white boxer briefs, Raul with Jasper's blue boxers and Jack with Robert's black Calvin Klein briefs.

Once the four nude men were securely bound and gagged the two masked gunmen made their way behind the teller’s cage and began emptying the drawers into their sacks. Not knowing that Oliver was in his office the two crooks made their way for the exit. Looking back on this day Oliver would ask himself over and over again why he didn't wait another minute or two before exiting his office. If he had the two gunmen would have been gone and things would have played out differently. But sadly for him he did come out just a Al was scooping up the clothes of the four bound men and making a retreat for the door behind Dan.

Oliver didn't see the gunmen at first but he did see his employee's naked, bound and gagged. His first reaction was to yell out, "What the fuck!?"

At that Dan and Al turned to see a stunned Oliver Cromwell making his way toward his staff. "Hold it right there!” command Dan as he aim his gun at Mr. Cromwell. Oliver turned quickly and in an instant it all came together. The Savings & Loan was being robbed. Dan waived the gun at Oliver as he ordered him in front of the teller’s cage. Oliver raised his hands high in the air to show surrender and made his way to the front of the cage. His four employees sat there wide eyed and helpless as they watched their in control boss show the first signs of emotion they had ever seen.

Oliver's deep manly voice cracked like a thirteen year old boys as he pleaded, "Don't hurt me. You have what you want. Just be on your way."

Dan looked Oliver up and down in his designer three piece suit. His red silk tie tied tightly in it's usual double Windsor knot. Dan knew in a heart beat the Oliver was the big man around here. "I'm giving the orders, Boss Man. Now strip like the rest of 'em."

Panic flashed across Oliver's face as he realized what was happening. He was going to be made to strip like the rest of his staff. But he couldn't. If he did they would see his hairless body. They would see the black leather jock he had chosen to wear today. They would see his nipple clamps. They would see his thick silver cock ring. They would see his sterling silver butt plug. But worst of all they would see his little dick!

As he glanced at his underlings he couldn't help but take note that each one was better hung than the last. He'd be forever humiliated if these men knew his secret sexual desires. He would be further humiliated if these men saw his embarrassingly small cock. Oliver was only 3.5" fully erect. The butt plug in his ample ass was larger than that. Looking at Old Jasper he was guessing that his fat schlong, which snaked it's way down the chair, had to be over a foot in length and that was soft. What must he have been hard!? And Jack, the kid was only 19 and so damn skinny, but that dick it was huge. All four men were massive and Oliver was not, this embarrassed him greatly. It made him feel like less of a man somehow. It even made him feel less powerful. He had to look away.

Oliver Cromwell began pleading with the two masked men, "Please. No don't make me strip. Just tie me up. I beg you. Pleeeease!!!"

Dan loved it when they begged to be spared the humiliation of stripping. He waived his gun the executive's face and barked, "Strip, Boss Man. I won't ask again."

Oliver knew he had no choice. He closed his eyes as he slipped off his jacket. As he did the remote for his butt plug fell to the floor but was unnoticed by anyone including Oliver--unnoticed, at least for now. He then began to unbutton his vest slowly hoping that something would happen to stop this humiliation. He could feel his face getting hotter by the second and knew he had to be beat red as he tossed his vest in the pile with the other men's clothes.

Next Oliver reached for his tie. He began to undo his perfect double Windsor knot and pulled the tie free. He slowly began to unlace his well polished wingtips. Next he undid his pants extra slow, hoping that's something would happen to stop this humiliation. But, it didn't as he slowly peeled them from his full plump round ass and over his massive thighs. He now stood there in his sheer black nylon dress socks which were held up by a pair of black sock garters and his starched white dress shirt. He scanned the eyes of each of his employees and he could see the fear on their faces but there was something else. Was it glee? Were they enjoying seeing him humiliated like this. Of course they were. He knew they were. They resented him so of course they were enjoying his shame. Oliver closed his eyes as he began to unbutton his dress shirt. He could feel all six men watching him. He knew it was only a matter of seconds before his secret was revealed to them all. He finished unbuttoning his shirt and let it just slide of his well muscled shoulders to the floor. This was the moment of truth.

Dan & Al burst out laughing. Raul, Jack, Jasper & Robert could only gasp through their underwear gags. Oliver felt his face redden as he stood there in his stocking feet, leather jock, nipple clamps and not much else. "What the fuck you wearin' Boss Man!?", laughed Dan.

Oliver Cromwell just hung his head in embarrassment and looked the other way. He couldn't bear to face his tormentor.

To Al Dan said, "Looks like Boss Man has a kinky side."

"Sure does, Dan."

Dan walked toward Oliver and circled him. "Damn, Boss Man those little leather underpants don't have a back. That ‘cause your ass is so big you couldn't find a pair that would fit it?" Then he and Al broke out laughing.

"No.", said Oliver in a low humbled voice. "It's a leather jock strap." Fortunately he hadn't noticed the butt plug wedged firmly between Oliver's big plump gluts.

"Oh, sorry.", said Dan sarcastically as he reached up and gave a tug on the chain of the clamps firmly attached to Oliver's nipples. "And what do you call these?"

Oliver looked away as he whispered, "Nipple clamps."

That got a big roar from Dan & Al. Al spoke next saying, "He is kinda kinky Dan. Looks like he even shaved off all his body hair."

"He sure did. There's not one hair on his body below his neck." Then Dan turned his attention back to Oliver, "You sure are one perverted bastard. Okay Boss Man drop you leather underpants...Oh excuse me I mean leather jock strap.", said Dan as another fit of laughter overtook him.

Oliver wished he could just disappear. As embarrassing as this had all been he knew he was going to be even more humiliated once they saw his tiny dick in the sterling silver cock ring. But what could he do? They had guns. He had no choice so as his captors and staff watched he lowered his jock.

There was another group gasp from his staff and another round of laughs from Dan & Al as they saw Oliver's itty bitty flaccid cock for the first time. And wrapped around it was the thick silver cock ring.

"Look Dan.", said Al. "What is that wrapped around his dick?"

"Hold on…” said Dan, “I'm having trouble finding his dick." More laughter. "Damn, Boss Man, you sure ain't packin' much compared to your employees. They're all horse hung but your mosquito hung." Again the two masked men laughed.

Oliver turned crimson at this latest round of jibes. He had never been so humiliated in all his life. And worst of all his employees were here to see it.

Dan got in Oliver's face. He was so close Oliver could feel the other man's hot breath on his face. "Pretty small dick for such a big man. What are you about 2" hard." More laughter.

Mr. Cromwell couldn't even speak any longer his shame was too great. He just lowered his head and looked off to the side hope to escape this humiliation in some way. But that is when things got even worse. As Oliver looked off to the side he saw the remote to his butt plug. It was lying out in the open on the floor. His eyes grew wide as he realized this. Unfortunately for him Al caught his reaction and followed his gaze and spotted the remote. He walked over and picked it up. "What's this?” he asked Oliver.

Oliver found his voice and softly lied, "I don't know."

To Al Dan asked, "What is it?"

"I'm not sure,” replied Al. "Looks like a remote of some sort. It has ten speeds."

"Well, turn it on,” said Dan. "Let's see what happens."

Al just shrugged as he flipped the switch to level 1. Oliver twitched slightly as the 4" plug buried deep in between his mountains of ass came to life. His fleshy slabs of ass muffled the low hum of the motor. But everyone notice him twitch as the remote was turned on. Dam instructed Al to bump it up to level 2. This caused another twitch from Oliver. And this time there was the unmistakable low hum of a motor. Dan and Al began walking around the room trying to locate the source of the motor. Oliver's blush deepened as his prostate was massaged by the vibrating of the plug. It was starting to feel good. Too good. He could feel a stirring in his groin. Then it happened. His cock began to grow. As much as Oliver tried to fight it the massaging of his insides was too much for him.

Jack was the first to notice Oliver's tiny dong grow. He chuckled behind his gag of Robert's black Calvin Klein briefs. This got the attention of Robert, Raul and Old Jasper. All four men sat there wide eyed, just as naked and exposed as Mr. Cromwell but none sporting wood like Mr. Cromwell. Each man smiled to himself thinking of the way he'd been treated by Mr. Cromwell. Each man enjoying seeing this arrogant prick brought down a peg.

Oliver saw all four of his employees staring and laughing at his small hard prick. He covered his miniscule manhood with his hands. He could feel his face burning with humiliation.

Then Dan turned and saw Oliver covering himself and snapped, "Hands at your side, Boss Man!"

Oliver didn't want to move his hands but he knew he had no choice so he lowered them back to his sides slowly. Dan roared with laughter as he saw Oliver's little penis growing, "You getting off on this, Boss Man? You like be exposed like this? You like having your employees see that tiny little dick?"

"No.", whispered Oliver. But his stiffening dick made Dan believe differently.

To Oliver Dan just spat out, "Pervert." Then to Al he said, "Turn it up another level. I wanna find the source of that humming."

Al went up to level 3 and Oliver twitched again; a fact that no one in the room missed. The humming of the motor got louder. Al and Dan made their way toward Oliver. His cock rock hard at it's full length of 3.5".

"It's coming from him, Dan.", said Al.

"It can't be."

Al got down on his knees. "I can hear it louder. It's coming from...This is gonna sound crazy but it's coming from his ass."

"What!?" barked Dan. He grabbed Oliver and spun him around and bent him over. "Grab your ankles Boss Man."

Oliver had no choice he did as ordered grabbing his calves just below his sock garters. His over stuffed ass was aimed skyward and visible not only to Dan and Al but also to his staff. Dan spread Oliver's big rump and saw for the first time the end of the butt plug sticking out his ass. He grabbed it and popped it out; his puckered ass hole visible to everyone in the room. The stainless steel plug just continued to vibrate. Dan held it up and burst out laughing.

"What is this Boss Man?"

Humiliated Oliver looked at Dan between his legs and softly said, "It's a vibrating butt plug."

"You are one twisted fuck.", said Dan as he rammed to plug back inside Oliver.

Oliver bucked forward. "Please no.", pleaded Oliver. "Don't put it back in me."

"What’s' the matter you must like it in there. You put it in there in the first place." laughed Dan.

"Please at least turn it off then." begged Oliver.

"No.", snapped Dan. "Al, turn it all the way to level 10."

Oliver straightened up and turned to face Dan, "No, please. Don't. If you do that I'll..."

"You'll what?", asked Dan

Oliver looked away as he said, "Cum."

Dan roared with laughter as he ordered Al to crank it up. He then ordered Oliver to stand in front of the teller’s cage and face his employees so they could see the show. Oliver felt the vibration climb in intensity. As the intensity grew it caused Oliver's hips to involuntarily thrust forward as if he were fucking the air; his small cock flopped up and down as he fucked some imaginary being. Old Jasper and the rest were obviously laughing behind their gags as were Dan & Al. Oliver was involuntarily fucking the air and moaning with lust. The massaging his prostate was getting over trumped his humiliation--at least for the moment.

The whole time Dan kept telling Oliver what a sick pervert he was, humiliating him further by pulling on the chain that joined his nipple clamps. As much as Oliver hated being treated this way he definitely liked having his nipples worked over and his insides massaged. Soon it was too much. Oliver let out a loud scream of ecstasy & shame as he felt his nuts explode. Stream after stream of warm white jizz spewed from Oliver's undersized manhood. He was humiliated beyond belief as he watched his seed hit the floor of the Savings & Loan.

"Fuckin' perv,” snarled Dan. "Help me tie him up, Al"

Dan & AL decided to further Oliver's humiliation. They tied him standing up spread eagle to the teller’s cage. His arms securely tied to the cage and his legs securely tied to the posts on the ground. He was facing the rest of his staff. His cock was still fully erect and the butt plug still vibrating on level 10.

"Please turn off the plug.", pleaded Oliver.

"No way Boss Man, you can entertain your employees all night.,” said Dan as he pulled some duct tape from his jacket and began wrapping it around Oliver's ass taping his ass cheeks together so he couldn't expel the plug.

"NOOOO!!!” pleaded Oliver once he realized what was happening.

Then Dan & Al gathered up all the money and the five men's clothes and made a quick retreat leaving Oliver on display for all his employees to watch as the vibrations made him fuck the air. Oliver couldn't help but stay hard from the massaging of his prostate. And it felt so good he couldn't stop himself from moaning out either. Robert, Raul, Jack & Jasper just watched in stunned silence.

The next evening when the cleaning crew arrived they found the four men still bound and gagged in their seats and Oliver still tied to the teller’s cage wearing only his sheer black nylon dress sock, sock garters & cock ring. He was still hard and fucking the air. At his feet and dribbling down his leg was a huge puddle of his own cum--some of it dry and crusty and some fresh. Over the course of the past 24 hours Oliver had cum no less than 15 times. He had actually reached a point where nothing more would come from him but air. But that didn't stop the feeling of ejaculation and the moans of pleasure that followed them.

In the end Oliver managed to get the cleaning crew, Raul, Robert, Jack & Old Jasper to keep what had taken place a secret. Of course that meant raises for all as well as a new found humility in Mr. Cromwell. But Old Jasper made sure Oliver stayed true to his work when he confiscated the security tape before Oliver had a chance too.

And they all lived happily ever after. That is except for Oliver Cromwell. He no longer felt the sense of power he once did as he walked among his staff. He had heard them whisper amongst themselves and though he could never make out exactly what was being said occasionally he would make out a word or two here and there. Like butt plug or nipple clamps. Oliver had been humbled not by choice but by force. And it was a lesson Raul, Robert, Jack & Old Jasper were going to make sure he never forgot.

The End