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Jerry Gets His Chance

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Jerry Monroe is your typical single mid-thirties guy. He drives a four-door sedan and lives by himself in his one bedroom apartment. It is decorated circa 1990 and he likes it that way. He has worked at Johnson Technologies since he graduated from college 14 years ago.

Sarah Blaine is a sexually repressed twenty-eight year old woman. She always dresses in a quite conservative blouse and skirt for her job at Johnson Technologies. Her roommates are cats and she spends most of her alone time dreaming of a knight who will take her away from her boring life.

Rich Gordon recently turned thirty. He is a surfer dude and enjoys spending most of his time at the beach. He has been surfing since he was ten years old and playing competitive beach volleyball since high school. He has had no problem getting laid whenever he pleases and generally oblivious to people while he is working his day job at Johnson Technologies.


Jerry sits at his usual corner table. He has just started eating his regular Thursday lunch of turkey on rye with a container of peaches and a Diet Coke, when Sarah enters the room. His eyes lock on her as she walked to the vending machines. Jerry has been carrying a crush on Sarah since the week she started here at Johnson Technologies. She always seems to be a very private person and has never given him much more than a glance. Jerry would love to have a chance with Sarah.

He watches as she sways her hips a little while she tries to decide what she wants from the machine. Although she dresses conservatively, Jerry is quite sure she has a killer body hidden under her façade. Being a single thirty-six year old had led Jerry to be quite the connoisseur of adult films and he takes great pride in being able to picture a female figure even if it is fully dressed.

Sarah makes her selections and takes them to a table about twenty feet away from Jerry. She has a magazine in her hand and begins reading as soon as she sits down. As usual, not even a glance in Jerry’s direction. He sighs to himself and continues his lunch.

About this time, Rich Gordon walks in the room. He is basically the arch nemesis of Jerry, as they are complete and total opposites. Jerry frowns at him although Rich wouldn’t notice if Jerry were lying dead on the lunch table.

“Oh, hi Rich,” says Sarah.

Jerry fumes to himself as the object of his affection would even talk to a guy like Rich.

Rich looks briefly at Sarah, “Hey babe.” He then swings his body around and makes a couple quick steps to put himself in front of the sport drink machine. He makes some sound effects as he drops his coins in and then does a judo punch to make his selection. He laughs to himself as he is obviously amused by his own antics. Jerry rolls his eyes and looks back to Sarah. She is staring at Rich with a longing in her eyes and Jerry then notices that one hand has dropped to her lap. She is ever so gently running her hand back and forth across her skirt. Jerry had seen this before in one of his movies, she is actually masturbating right there. This sickens Jerry to know that Sarah truly does have an interest in someone like Rich.

He mumbles to himself, “What I wouldn’t give to be Rich for a couple days…”

The rest of the day goes by quite normally and Jerry heads home for the evening. An evening filled with network television, a light dinner, and of course some masturbation. He falls asleep about nine on the couch in his work clothes.

Morning arrives and his alarm is there to greet him at five sharp. He stands up and stretches a little.

“I gotta quit sleeping on the couch, I feel awful this morning.”

He shuffles towards the bathroom, hitting his head on a light fixture in his hallway.

“What the hell, today sucks already! I’ve never hit my head on that thing before!”

He continues in to the bathroom and makes his way to the toilet. He pulls down his boxers to take a leak and…

“Holy shit… where did that come from!”

Somehow during the night his five inch penis had grown to a healthy eight inches and quite a bit more girth. He stares for a moment and then turns to look in the mirror over his sink.

“Oh… my… God…” is all he can manage as he is looking directly in the eyes of Rich Gordon. How could this be happening, why would he be forced to become his enemy?! Then it hits him, this is exactly what he has asked for, only he didn’t actually think it would happen. He thinks back to lunch on Thursday and about watching Sarah respond to Rich as he entered the room.

A familiar tingle moves through his crotch as he thinks about Sarah. He glances down to see his new cock slowly rise to attention. He touches it a little, as it still seems a little like he is touching another guy’s dick. However, the sensations running through his brain as he thinks of Sarah masturbating quickly take over. He begins stroking it and moaning to his mental images of a nude Sarah. Moments later he cums on the floor of his bathroom.

“Shit, now I Antalya Escort have to clean that up,” he comments as he grabs a towel. He then quickly showers, all the while admires how good of shape Rich is in. He is torn between wondering what this body can do and feeling a little bit of his homophobic feelings surface.

Lucky for Jerry, an old roommate of his had been built about like Rich and had left behind some clothes when he moved out. Jerry, being your typical pack-rat, had kept the items. He digs out the clothes and gives them the once over with some Febreeze.

He quickly dresses and bolts for his car. As he speeds towards the office he realizes that “Rich” can’t show up in Jerry’s car, so he stops two blocks away at a city lot. He grabs his briefcase and then decides against it. He knows he doesn’t need anything in particular to do Rich’s job, in fact he had done Rich’s job many times from his own workstation at his boss’s request.

The two block hike seems like no big deal as “Jerry” is now in tremendous physical shape. He feels like he could walk all day with no problem. He enters the building and casually strolls towards his office.

“Hey!” says a voice from his right.

Jerry looks over and sees a cute brunette with a feigned frown on her face. This could be interesting he thinks.

“You were just gonna walk on by and not even say hello!”

“No, babe,” he says, trying to imagine what Rich would have said. “I wouldn’t skip talkin’ to you for nothin’!”

She giggles and looks up at him. “So, are we still on for our normal Friday appointment?”

“Uh, yeah, of course we are,” he says wondering what this appointment could be.

“Good. Now you better be in your office at ten when I get there, and not off chasing some other piece of ass!” she whispers to him.

“Oh, I’ll be there.”

He gives her a wink and turns to head for his office. He begins to realize that Rich may just have an unlimited supply of pussy here at Johnson Technologies.

He winks or gives a thumbs up to all the ladies as he makes his way to his office up on the third floor. He plops down in his big leather chair and takes in the view, as his window looks out above the surrounding buildings and out across the ocean.

“Son of a bitch, this guy has it made.”

The phone buzzes and Rich’s secretary’s voice comes across the line.

“Mr. Gordon, I have your morning paper if you are ready.”

“Yeah, sure,” he replies.

About ten seconds later a tall, blonde, Playboy looking woman walks in his office. Jerry struggles to keep his jaw from hitting the floor as she walks toward him. She lays the paper neatly at the corner of his desk and walks back to the door. Jerry is glued to her perfect ass as she walks away.

“Will there be anything else this morning, sir?”

“Oh, you know, typical Friday…”

She grins and pulls the blinds closed. She then closes his door and locks it. Jerry must have luckily said something right. She immediately peels off her blouse to reveal her braless and obviously silicone double D breasts. Still no complaints as she walks around his desk.

Jerry leans back in his chair and just watches as she clicks the button on his chair to release the arm rests. They fall to the side of the chair as she pulls down his zipper. She gives the waistline of his pants a good tug and then snickers a little. Jerry immediately wonders what has gone wrong.

“Oh, Mr. Gordon, you are wearing underwear today? That’s new!”

Jerry cannot believe what he is hearing, this is almost too good to be true.

“I thought I’d mix it up.”

She just shakes her head playfully and pulls the boxers down too. She then grabs his already hardening cock and gives it a few good strokes. He decides to get all he can from this situation and slides her skirt up, revealing a beautiful and hairless pussy. She immediately swings her leg over his lap and lowers her pussy toward his now hard cock.

Jerry just sighs as her warmth surrounds his penis as she slides down to sit on his lap. She begins rocking back and forth, quickly milking his cock. Jerry can’t help but think she has done this many, many times.

Her pussy begins to make a squishing sound as she pushes down against him. He is focused on the gorgeous breasts in front of him and takes a nipple in his mouth.

“Oh, Rich, you’ve never done that before! It feels so good!”

Jerry says nothing but brings his hands up to massage her breasts and makes it easier to suck on her big tits. She continues to fuck him as he can feel her pussy grow tighter. Reality snaps back in as he feels a tingle down in his balls.

“I think I’m gonna come soon,” he says.

“Thanks for the warning,” she says as she grins. “I am counting on it!”

She redoubles her intensity as her clit is crushed against his pelvis again and again. He lays his head back as he feels the cum making its way to his cock. She slams down again with great force and he erupts inside Antalya Escort Bayan her. Her pussy walls grab him as a small orgasm tears through her body.

“Fuck…” is all he can manage as he pumps what feels like a gallon of cum into her.

She squeals a little and collapse against him, her giant breasts heaving against him. She then looks him in the eye.

“That is the first time in three years you made me cum, you know it! I was about to give up hope on you, but I guess I’ll keep trying now!”

She giggles as she raises herself off of him, placing a handful of Kleenex at her pussy to catch anything that might run out as she stands up. She then quickly bends down and takes his cock in her mouth. Jerry’s eyes roll back in his head as she quickly licks him clean.

In a matter of moments she has dressed herself and zipped his pants back up. A full service secretary for sure! Jerry just smiles as he watches her head for the door. She turns and blows him a little kiss as she unlocks the door. The door closes behind her and he just lets out a sigh.

“Holy shit, I wonder how I get one of those for my office…” he wonders as he glances over at his computer. A reminder has popped up on his calendar. “Ten minutes until Julia arrives,” it says. The clock reads 9:50, so he assumes Julia must be the brunette from the lobby. He straightens his clothes and sprays some air freshener to mask the sex smell in the room.

Sure enough, ten minutes later the gorgeous woman he had seen in the lobby walks in. She closes the door behind her and notices that the blinds are already closed.

“I suppose you were trying to help me out?” she chuckles as she clicks the door locked.

She walks over and leans forward on his desk. Jerry can’t help but stare down her blouse, which is of course what she wants. He also catches a glimmer off of her hand. He glances down and sees a very nice diamond ring on her left hand. Jerry knows this must be quite the affair.

“Admiring the ring again, huh?”

“Oh, well, you know…”

“Look, that jackass won’t even attempt to stick his cock in me, so don’t worry about him. Hell he probably wouldn’t even care if I told him someone else was getting me off for him. I just wish you’d give in and fuck me one of these days!”

“Look, you know I’d love to, but…”

“Oh, what? You have some morals now?” she says with a smile.

“Let’s not be silly… of course not…”

“But the jackass is your brother, right?” she says. Jerry can hardly believe what he is hearing. Even Rich’s sister-in-law is trying to fuck him.

“Yeah, you know how it is.”

She just smiles and nods. She then walks briskly around the desk and kneels beside his chair. She spins the chair until his crotch is right in front of her. Without saying a word she opens his pants and pulls out his cock. Leaning forward, she takes it in her mouth.

She begins sucking with abandon, running her tongue all over his meat. Jerry can only imagine that getting a blowjob from you sister-in-law is fine, as long as you don’t fuck her. What a crazy life Rich has.

He holds out for a while, as he just dumped a huge load in his secretary. A few minutes in to the blowjob he reaches down and feels her tits. They are real for sure, and at least a large C. Why in the world would anyone refuse to fuck someone with a body like this?!

“I know you like ’em, Richy. You sure you don’t want me to take them out for you?”

“No, I think you better leave ’em in there,” he says. She doesn’t respond other than returning to the blowjob before her. A few minutes later, he sprays a small load into her mouth, which she swallows with no problem. He hands her a Kleenex and she wipes the corners of her mouth.

“You know,” he says with a thoughtful look on his face. “I think I know of a guy who you could fuck all day and no one would even begin to suspect you of it.”


“Yeah, there is this nerdy little fuck down in IT. He probably hasn’t ever even seen a pussy. He’d probably cream himself if you made a pass at him.”

“Hmm,” she says. “Well, do you think he could be discrete?”

“Oh, I’m quite sure of it really. He owes me a favor, and he’d owe me much more if he knew what I have planned for him.”

Julia smiles, “Well who is it?”

“His name is Jerry, but I think he is out today. I’d look him up on Monday. The key is you can’t tell him I sent you and you probably shouldn’t mention him to me. Deal?”

“Look, if it gets a cock in my pussy on a regular basis, I don’t care what it takes. So, yeah, deal. You do know that I may have to cancel our Friday appointments if this works out, right?”

“I’ll just consider it to be me taking one for the team, ok?” Jerry says, smiling at her.

He knows that even if he only gets to touch her on Monday, it will be better than any other Monday before. Julia stands and walks to the door, leaving his cock flopping in the breeze. Jerry smirks at her and zips up his pants.

She Escort Antalya waves as she opens the door and heads back to her post in the lobby. Jerry can hardly believe how perfect his Friday has been so far. It is now ten thirty, he has already had a good fuck followed by a masterful blowjob. He has one more task in mind for the day, but he is now leaving all options open.

“Time for snack I think.”

He walks out of his office and towards the elevator, giving his secretary a wink on the way by. She just smiles and shakes her head as she continues working. He pushes the button labeled “B”. He knows this floor all to well from his normal life, but that is where management had decided to put the break room.

He walks casually from the elevator towards the break room, although he is eagerly anticipating the presence of Sarah Blaine when he gets there. However, when he pushes the door open, he sees no one. Even the sad little table in the corner, where he normally ate his lunch was eerily empty.

“Damn,” he says as he looks around the room. “I was really hoping she’d be here.”

“Who?” says a voice from behind him. Jerry doesn’t even need to look as he knows that voice anywhere. Sarah had caught him by surprise. He turns slightly and grins at her. She returns the smiles in a sheepish fashion.

“Well, you, of course, babe”

“Oh Rich, you are crazy,” Sarah says as she walks past him, barely brushing against him on her way to the vending machine. Jerry watches her and then closes the door. He quietly clicks it locked, as it would normally be when maintenance is working in here.

He then slowly walks around behind her, admiring her ass.

“Are you looking at my ass again Rich?” she says without looking away from the machine.

“Maybe, just trying to decide what I want for lunch…” he says as his voice trails off. This is some cheesy shit is coming up with. He can only thank years of horrible dialogue in many porno flicks for ideas of how Rich talks. Unfortunately, that is how Rich talks!

She chuckles a little and then pushes a button. A soda drops to the opening at the base of the machine and she bends to pick it up. Jerry seizes his chance and steps forward, pressing his hips against her. He puts a hand on her back to keep her bent over and quickly pulls her skirt up.

“I think I figured out what I want,” he says as buries a finger in her pussy. Jerry can hardly believe that Sarah doesn’t even have panties on. He saws his finger in and out of her as she just stays in that bent position, leaning against the soda machine. She reaches back and grabs his cock through his pants, giving it a good squeeze.

Jerry knows he always wanted to be romantic with Sarah, but this was probably as close as he would get. He deftly uses his free hand to loosen his pants and free his cock. Sarah grabs it and begins running it along her pussy. She is soaking wet in no time and jams this cock inside her. Sarah had craved this moment for years and could hardly believe she finally had Rich Gordon’s cock inside her.

Jerry begins pushing into her, flexing his penis as he finally reaches the end of her tunnel. Amazingly, he still has about an inch of cock left. He can see her wince a little as he pushes against her cervix. Jerry can hardly believe that Rich’s cock is too big. He doesn’t give this too much thought as he simply adjusts his strokes to fill her, but not hurt her.

Jerry pulls out and grabs her by the hips, guiding her to a table.

“Turn over, babe”

Sarah sits on the edge of the table. Jerry quickly reaches for her blouse, unbuttoning it quickly. He unfastens her bra and releases the breasts he has sought for years. He gently takes one in each had and gives them a good squeeze. She moans her approval as he kneads them. Stepping forward, he bends slightly at the knees, he then brings his body back up as his cock slips back into her pussy.

Sarah just braces her self on the table as Jerry fucks her and plays with her tits. She is in heaven and so his he. He releases her tits and hugs her close as his cock begins to twitch. Sarah quickly reaches down and pulls his cock from her pussy.

“Oh, Rich, I’m not protected… I would love nothing more than to let you cum in me… but not today…” she says in disappointment. He stares at her, trying to figure out a way to keep from getting blue balled.

He lifts her off the table and spins her around. He then leans her over the table and sticks two fingers in her pussy. He twists them around for a moment and then smears her juices on her asshole.

“Oh, yes, Rich, fuck my ass!”

Jerry wastes no time and gives a solid push as the head of his penis penetrates her ass. She shrieks a little at the size of his cock in her ass, although this isn’t the first time she has had one in there. He begins pushing into her and the swelling in his balls begins again. Only minutes later he impales her ass with his cock and fills her with his cream.

“Oh, fuck yeah!” he yells as he spurts several times inside her.

“Yes Rich, YEESSSS!” she screams as she feels as orgasm starting. Jerry decides this could be his chance to make Rich look bad and manages to have the presence of mind to execute the plan. He pulls out of her ass steps back.

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