Gloryhole Switcheroo

"Alright Zach, deep breaths. You can do this." Zach sat in his car in the gas station parking lot, heart racing. His hands still gripped the wheel, unconsciously twisting them as he worked up the courage to make his way inside.

Zach was nearly done with his last summer before college, and like every other boy he had only one thing on his mind: getting laid. It hadn't happened for him up till now, and he was getting desperate. More than just the physical desire, he didn't want to enter college as a virgin. He was not socially adept enough to know how little it would've mattered.

Nor was he all that capable when it came to attracting the opposite sex. Zach was thin as a rake, pale, with a smattering of freckles around his black-rimmed glasses. They surrounded blue eyes, and falling to his shoulders were long, strawberry blonde locks of hair that too many fantasy movies had made him associate with 'dashing' men. At 5'7" he was no hunk, no one that was casually lusted after. And like many boys like him, he had turned to the internet to solve his problem.

Somewhere in the miasma of 3 am internet searches, Zach had found an opportunity he couldn't have dreamed would work. After striking out countless times, he stumbled upon a well-hidden offer: there was a woman who scheduled glory hole visits for attractive men at the gas station on the other end of town. The post seemed too good to be true, but had (safe for work, non-incriminating) pictures of a very attractive woman's face along with the offer, and a host of comments from men declaring their satisfaction with what she had given them.

She didn't take just any man, though. Potential suitors would have to send her a picture of their face, their cock, and their name/age. From there she would pick the lucky guy (or not), and more instructions came from there. When she messaged Zach he could feel his heart practically leap from his chest.

Her message was direct and to the point. She told him she thought he was so cute (not something he was used to hearing from women, especially ones as attractive as her), and that she had selected him to give a blowjob on a Friday night. He was to go to the gas station at 9:30 pm and immediately go up to the cashier and ask for the key to the bathroom. She said Zach would have to give the man a twenty dollar bill (the cost of getting a routine place to play), and from there he would go to the men's bathroom. The women's was right next to it, and a convenient little hole would offer a place for Zach and her to have their fun. At the end, she sent a picture of herself holding a small piece of paper saying 'See you soon, Zach!' as means of proof that she was indeed who she said she was.

And now, Zach turned the key to his car, pushing the door open and stepping out before he lost the small bit of courage he had forced into himself. The competing feelings of apprehension and lust were tying knots in his stomach, but he willed his legs forward. He looked around the gas station, but there were no other cars there. He slipped his phone out of his pocket: 9:01 am. He would feel silly if he did all this just for her to no show... but he would feel worse than silly if he missed the opportunity to get sucked off tonight.

He pushed the gas station door open, the annoying rattle of a physical bell sounding as the door pressed against it. Zach glanced left and right, laying eyes on the cashier. It was an elderly Middle Eastern man behind an almost solid wall of plexiglass. He didn't look up at a customer entering. The whole place was lit dimly and smelled of some fruity cleaning product. Zach walked slowly up to the counter, the attendant only glancing up as Zach couldn't come any closer.

"Hi, um... I'm here for... Do you have a key for the bathroom?" He looked sheepishly at the man. It felt almost like a prank; he didn't even know for sure the bathroom had a key beyond the woman from the ad telling him so. And he didn't even know her name! Zach's heart was about to beat out of his chest with embarrassment, and the old man just stared at him, face like stone.

"Oh! Uh-" Zach took a crumpled twenty-dollar bill out of his pocket and pushed it across the counter to the opening of the plexiglass. The old man looked down at it, slowly reached out, and took it, his other hand drifting under the counter. He produced a small key attached to a huge wooden spoon, sliding it back over to Zach.

"Return it when you are done. Don't lose it." Zach practically choked at the idea of losing the key on its anchor, but dutifully nodded and said a quick 'thanks'.

He quickly about-faced and made towards the even more dimly lit hallway on the opposite side of the building from the cash register. Just as he had been told, there were a set of bathrooms next to each other. The women's bathroom had a large 'Closed for Repairs' sign on it. His hands were practically shaking as he inserted the key into his door. He turned it, opened the door, slid in, and shut it behind him in one swift, hasty movement. He went to lock the door behind him for security but frowned as he saw there was no way to lock it from the inside. The sign on the other door acted to keep people out of the other bathroom, but for Zach, there wouldn't be anything but to hope no one else tried the door.

As he turned to face inward he was surprised at the bathroom's near opposite appearance as the rest of the store. It was clean, the white tile walls not even having leftover signs of being wiped, and it was incredibly well-lit. Next to the toilet, Zach's eyes settled on a small hole, and as if on cue a few slender fingers with bright red nail polish slipped through, one beckoning him over.

"Don't keep me waiting, sweetie." Came the husky voice of a woman on the other side. Zach stepped over, setting the key and spoon on the sink, and hastily unzipping his pants. Now that he was here and it looked like everything was going perfectly the lust side of his brain took over completely. As he got up to the hole the fingers quickly retreated. Zach pulled his pants and boxers down in one swoop, letting them settle around the middle of his thighs, and he brought his rapidly enlarging cock up and into the exposed hole.

"There we go." Came a breathy response from beyond the wall, and Zach gasped as cool hands took hold of him. She expertly lifted his balls up and through the hole, tugging on them a bit as her hand began stroking his cock. It was heaven. Zach pressed himself up against the wall, turning his head to press his hips as hard into it as possible. He was gasping as he achieved his full erection, feeling her hot breath on him as she pumped him. His hands flailed against the wall, searching for something to grip as he kept hoping, anticipating she would take him into her mouth.

"Ah! Hey, wait-" There was a sudden tightness around his cock and balls, like a bit of elastic getting cinched. He might've recognized the sensation as something like a cock ring if he knew the feeling, but instead, he instantly felt in trouble. He attempted to step back, but whatever was fastened around him was wider than the glory hole; his cock and balls did not move with his body, keeping him mostly anchored in place.

He winced, but the hands kept lovingly working on him. The tightness seemed to make him harder too, and soon he found he was panting and his cock was pulsing. He felt harder than he had ever been, more on edge than ever. His hair cascaded down his face and he didn't bother to move it, his breaths keeping strands from his mouth. He wanted so much for her to put him into her mouth, but he was getting so close...

And then nothing. He practically yelped as he felt the hands leave him, all pleasant sensations abating. His hips would have bucked if they had any real place to go, but he was fastened in place. After a moment, he heard the bathroom door next to him open. He froze, hearing the few steps between the two, and turned in a panic as the unlockable door to his bathroom opened.

Stepping into the bathroom was no doubt the woman he had seen in the pictures online: she looked to be in her mid to late 20s, had long brown hair (although it was a bit more unkempt than he had seen before), and she wore a white tank top that didn't make it to her waist. She was plump without being chubby, and a large pair of breasts bulged underneath the tank top with a generous amount of cleavage. She wore grey sweatpants, and other than the immaculate red nail polish she had no other makeup. She gave off the impression that she had not made any special preparations for this event. There were only two noticeable differences between the pictures he had seen online and the woman before him. The first: she was huge. She towered over Zach from the door, and must've been at least 6'2". The second she revealed as she stepped in, tugging her sweatpants down to reveal a huge, meaty cock.

Zach's mouth dropped open but no words came out. She stepped towards him with a smile but seemed too preoccupied to fully care about him.

"You bitches are always so cute when you first see it." She quickly produced a tiny bottle of lube from her pants, smearing it on her cock as she began jerking it into a much harder state. "It's half the fun of sticking it in your ass."

"Wait!" Zach yelped, attempting to step back but eliciting a pained noise as his crotch remained stuck. She laughed, rapidly stepping up behind him and pushing him up against the wall.

"No reason to struggle, boy. You're not going anywhere and I'm going to have my fun." His pants were still pulled down a bit, and her cock slid between his cheeks, poking up just above his ass crack. She ground into him, pressing him up totally against the wall. He tried to move his hips back and forth and force her away but only turned her on more. "You know I really do suck off hot guys with big cocks who come here. It's just when feminine fags like you apply that I make sure to get my nut." One of her hands gripped his ass cheek, prying it away. She took a half step back letting her cock fall, aiming straight at Zach's hole.

"No! Please!" Zach sobbed, his hands working behind his back to try to force her away. It was no use though, as the position gave him no leverage and she was already much bigger. She didn't even bother trying to fend off his hands. She just took her free hand and covered his mouth while she pushed her cock forward.

Zach's eyes bulged as the cock pushed at his sphincter, the pained words unable to make it out of his mouth as the hand squeezed tight. But the combination of his hands and shaking hips was enough to keep her from finding the right angle to continue. He panted as she grunted with frustration.

"I get what I want, baby." The three bottom fingers of her hand stayed holding Zach's jaw shut tight, while her thumb and forefinger moved up to pinch his nostrils shut. He tried to shake his head as he realized he couldn't breathe, but her hand was stronger than he was. "And I want all 8 inches inside you. So if you want to breathe..." She pushed her hips forward again, starting the process over. "Then you better let me turn you into a cock puppet."

The burning in his lungs finally overpowered that of his anus, and Zach straightened instead of turning. The cock head burst through him like a searing flame, and she wasted no time pushing as much of herself into him as she could. Her fingers slipped off his nose as she barreled forward and Zach greedily tried to suck in air, only for it to be knocked out of him as she pushed forward, deeper than anything he could've imagined inside of him.

"What a good little hole you are, taking me like this." She growled in his ear as she speared her cock into him. "Cute boys like you almost never answer my ads. I wait forever for you little bitches and once I get my hands on you..." The hand pulling his ass cheek apart released him, instead giving him three hard, loud slaps on the ass. "And lucky me that I happened to pull a fag with a big bubble butt like yours. Listen to it clap as my balls hit it. With your dick and balls stuck through that wall you look like practically a girl from this side."

Her thrusts were relentless and the tears running down Zach's face seemed to have no effect on the pace she set. She had no set rhythm and it was more like an internal bludgeoning than anything else. Zach's prostate got the occasional pleasurable sensation out of him thanks to his forcibly engorged cock, but the sweat coming off his forehead had nothing to do with that.

"God your butthole is so tight. I bet you're a virgin, too, aren't you? Hoping to stick that dick through a hole and have some magic happen. Well, my cock doesn't even fit through that hole and now it's totally in you. Think about how big your asshole must be right now. So stretched around a real cock." She punctuated her words with spanks and laughs, but Zach could hardly hear it. Her cock felt like it was up so far it was hitting him in the back of the brain, and his head being pushed against the wall didn't help.

"Thank god you can't get pregnant because I am about to leave so many babies inside you. Your butt is my own little glory hole, and I'm about to leave it a leaking mess." He could feel her cock swelling, somehow getting larger inside of him. It was like it was rearranging organs. "Tighten up for me so I cum extra hard, ok?" Her free hand smacked him on the back of the head. He winced hard, reflexively tensing his anus. "Oooooh yeah, just like that." Three more smacks in quick succession causing her to moan each time.

"Get ready get ready get ready." She whined, moving her hand around until both were clamped tightly over Zach's mouth. She pulled back, arching his back as she pulled his head for leverage, her cock larger than ever before and her thrust needier. "Swallow all this cum with your butt, bitch." Her words were almost pained and she pressed herself into him as the burst of heat hit Zach in what felt like his spine. She hilted herself in him, holding it desperately as she grunted with each rope of cum she lost up inside him. She thrust ever so slightly as her cock swelled, releasing a new load each time.

After what felt like an eternity she let out a sigh, her cock only dripping inside Zach's body. She took one hand from Zach's mouth, pulling his ass cheek aside again to allow her cock to escape from his agonized and rapidly winking anus. She chuckled as it came free along with a deluge of cum.

"Whew... that was great. I'd love to make you clean my cock off but I don't think you'll be able to reach it in this position." He could feel her pulling her pants back up, still keeping his mouth shut tight.

"I'm pretty beat from all this, so I think I'm gonna go home." She whispered, her mouth right up against Zach's ear. "I think it's probably best if I'm not the one to... release your thingy. Give it about ten minutes and the cashier will go into the other bathroom. Don't worry, he won't play with your cock or anything." Her laugh was genuine, somehow lacking any hostility. "He'll just pop the little contraption off your cock and you can run on home to jerk off. Cuz I know that's what you're going to do." She fondled his butt cheeks a little more, looking down at them as she shook them.

"You know you are a hot little piece of ass. If I don't get any more guys like you coming around I'll be sure to message you." She gave him a hard swat across his butt. "Make sure you answer."

She released her hand from his mouth and in a flash she was out the bathroom door, not bothering to stay for Zach's gasp. He panted against the wall, his forehead resting on it, his cock still rock hard despite himself. He whined softly, waiting for it to be released.