Haven’t written in a while so this is kinda like my warmup
Jim walked through the large glass doors, glancing at the email from his hopefully soon to be boss.
A reference from his college had given him the lead for the job. He figured his good college education along with him being the good guy he had good chances. He walked through some security gates and walked into a packed elevator full of people in suits. He watched as each one of the people one by one left the elevator as he passed their floors.
He was heading to the top, figuratively and almost literally, he stopped only a couple floors short of the top floor. The pearly silver doors of the elevator opened up and along with them so did Jims eyes, the office was empty except for one tall, but attractive redhead in casual clothing. Her legs were flawless and toned, and in addition were well shown off by her high cut tight jean shorts. Her figure was perfectly defined from her calves all the way up to her shoulders. Her breasts were a non exaggerated c cup and in good shape for some one her age.
“Well I can wait as long as you want for you to walk over here and shake my hand” she said laughing a bit
Jim’s eyes dart up from her breasts to her face as he said, ” uh um sorry about that I’m Jim”
She was significantly bigger than him, primarily due to the fact that her heals were about 4 inches. With them on she stood about 3 inches above six feet, and on top of that about 6 inches taller than Jim.
They shook hands as she said, “Call me Jane and don’t worry about it I get it all, especially with you younger guys, even though I have ten years on you”
Jim was shocked, how could a woman like this be like this be 33? It just wasn’t possible; regardless she looked amazing for someone her age. As she led him back to what he guessed was her office for the interview Jim, gazing at her long legs made an effort to start a conversation with her,
“So why are you so alone during the middle of this fine work day”
“Oh well when it comes to interviews I like to be truly alone with the people I interview, so I usually send a couple people home, but your a pretty special case so I sent everyone home so it would just be you and me.”
She looked back and tossed Jim a flirtatious smile as they reached the door. Jim asked
“Well what makes me so special?”
She continued to walk in and take a seat while inviting Jim to take one.
“So basically I want you to have an assistant-esque position with me, but I need you to be my special assistant if you know what I mean” she said
“I’m not sure I understand” replied Jim
She scooted up in her seat, adjusted her shorts, and leaned over her desk and boldly stated, “Well I get horny during the day and I need some one to help me out with that, can you do that?”
Jim gulped. He had heard stories of people fucking their bosses but he never really expected it to really happen to him, they were always just stories. But it wasn’t morally right to just take a job and just make money fucking his employer, as good as it sounded, he couldn’t do it.
“I’m sorry Jane but I just can’t”
She smiled and circled 2,500,000 on the page and said, “I make this much a year, and what if I told you could make a fifth of that by working for me”
Like any other kid fresh out of college he nodded his head yes too excited to even talk
Jane slowly move to the front of her desk and sat on the edge near Jim, it had now become clear there was a catch.
Jane was rubbing this massive bulge that looked like it had a hard time even staying in her jeans. She grabbed his hand and forced it onto her crotch as she said, “Still think you can handle the job?”
Jim quickly replied, “No I Definitely can’t” pulling his hand from her as fast as he could
“Aw that’s a shame cause you could make 800,000 if you just were my little assistant” she said
Jim didn’t know what to say, his mind was split. I mean it was 800,000 a year for a kid right out of college, it was ridiculous, and almost unheard of, but then again what was his job? He had to fuck a girl with a dick daily to make that money. After a minute of him almost pondering he decided, it’s 800,000 a year and he could get out if he wanted.
“I’ll take it” he said regretfully
“Great you start now” said Jane
She turned around and unbuttoned he jeans and dropped her panties.
“You ready?” she asked
“Yeah how bad could it—” he failed to finish the sentence
She turned and with it her 12 inch and thick cock, Jim was shocked, his dick was average and hers doubled his size. He regretted the decision as she stroked her long meaty pole in his face.
“You going to do something of just stand there?”
He was pale and scared, but he was a hard worker and wanted the money so he got down to work.
Still in his suit he gripped Jane’s massive cock and imitated the numerous amounts of pornos he had seen through his life. He began to move his tongue around her head. It was not long before his mouth was around Jane’s meaty member sucking as his head bobbed up and down.
“Look at me while you suck my cock baby” said Jane in a soft voice
He looked up and she was doing something that he hadn’t expected. She was filming him with her Iphone; he instantly removed his mouth from her cock but continued to jack her off.
“Hey c’mon now” he whimpered
She laughed in his face and said, “If you want that money you’ll tell me you love my cock and keep sucking, this video won’t go anywhere you don’t want it as long as you’re a good little boy”
He shamefully shook his head and moved his mouth back to her womanhood. He continued to jack her off as his mouth moved up on the first half of her shaft. He continued for another 10 minutes before Jim took his mouth of Jane and while panting said, “You plan on finishing anytime soon?”
“Not unless you really start to take this dick, instead of lollygagging on the first half” she replied angrily
She placed her Iphone back on the desk and knocked Jim’s hands off of her cock, she reached in her desk and pulled out some cuffs. She swiftly moved to his back and cuffed his hands together.
“Alright whoa I’m not ok with this” Jim shouted
“One take that bass out your voice, and two consider your situation before you talk to me like that again” she angrily replied
He relaxed as Jane moved back in front of him and resumed her position on the desk and placed her hands on his head, one under his jaw and one on the curve at the back of his head. And with out warning she forced her cock down Jim’s throat recklessly. She held him 9 inches down on her cock and after several pushes and weak punches to her abdomen she leg go of his head and sternly said, “Don’t ever fight me like that again, now swallow my cum like your supposed to” he was panting and couldn’t find the breath to respond she left one hand on his chin as she vigorously jacked her self off. It was only another minute before she guided his head back on to her cock. She made the final stroke and began to force Jim’s head down on her. Her cock expanded and forcefully sprayed load after load down Jim’s throat as he began to gag.
Jim, against his own will swallowed all of her bitter cum and once Jane let go, lifted his head off of her.
Giggling Jane said, “You know I wouldn’t have to be so rough if you were less resistant, but resistance does turn me on”
Jim as he got up and started to walk out mumbled, “Your just being a bitch is all”
Jane replied, “Ha-ha that’s funny, you’re the bitch here, and I don’t know where you think your going I’m still hard and you’re still cuffed”
“Well I’m done for the day so could you get these of me cause I need a break or something” replied Jim with some anger in his voice
“You’re not done yet bitch now come over here and bend over this table, so I can get a look at your ass” replied Jane
“I can’t do this, and I’m definitely not taking that thing.” said Jim, hands still behind his back.
“I don’t expect you to take this, but remember when I said consider you’re situation? Well I now have a video of you saying you love my cock, that I could send to who knows. So we could take that path or you could save yourself the embarrassment and make 800,000 a year…I promise I’ll be gentle, you’ll learn to like it”
She moved closer to him with every passing second until her cock was pushing up against his ribcage, due to the height difference. Jim was surprised by the change of tone he felt a bit more safe, and it did make more sense to just deal with it.
She guided him over to her desk and instructed him to drop his pants and bend over. He was wearing some rather lose fitting boxers all white except for the blue stripes that added some color to the edge of the boxers.
“Oh how nice, what a cute little ass” Jane exclaimed as her cock hovered powerfully over Jim’s back
she gave his ass a little love tap saying, “You like that baby?”
Jim honestly replied, “No, not really”
In that instant she went back to her aggressive mood and swung her open hand around and gave Jim a hard smack in this ass. Jim screamed out at the top of his lungs and tried to return to his upright position, but it was to no avail, Jane was holding him down with one arm and his ability to escape had gone.
“This is because you were defiant earlier and were also very rude to me, but I know you like this so let me know” she calmly said grabbing her Iphone off her desk to film the exchange.
She smacked his ass one more time and as soon as she did Jim said, “I love it”
She smacked him again and said, “C’mon now that’s not even believable say it like you mean it”
“I love it when you punish me” screamed Jim hoping to impress her the next time she smacked his as
“That’s very good now let’s try something else” she said as she moved behind him
She stood directly behind him and began to rub her long hard dick up against Jim’s ass, as she began to clinch tightly onto the cuffs.
Jim squirmed around as he said “Whoa, c’mon now you said you wouldn’t, you’re way too big for me”
Jane held onto him tightly and said, “Well hey sometimes I’m a liar, why are you trying to escape me anyways?”
Jim as a last shot for freedom flailed and kicked his legs around hoping to go free but he could not Jane was too strong for him. Jane had almost 50 pounds on him at muscular 170. She held him down with one arm and grabbed the lotion that was sitting on top of her desk while saying, “I’ll try to be gentle baby”
She put a generous amount of lotion all over her cock, as if it would really help Jim’s situation go from terrible to alright. She quickly leg go of the cuffs and ripped apart Jim’s boxers with ease, his ass was prone.
“The first times always a little rough baby, just stay with it” Said Jane
Jim was confused by the wide change in emotions Jane had, sometimes she was nice and other times she was, plain and simple just a bitch. But before he could fully finish the train of thought he felt a blunt and wide object pushing in his back door. It was Jane’s cock; she had begun to force the monster in.
It was no easy process, she pushed and pushed for more than 20 seconds, she was trying to be gentle but it became obvious this would take more force. Jim’s eyes were beginning to pour out tears as he knew there was now way he would get out of this situation, aside from begging.
“Please Jane, please don’t!” Screamed Jim
“I’ve got to do what I’ve got to do… you know I’ve never seen such a tight ass” She calmly exclaimed as she lathered lotion on her dick.
“Let’s give this one more try” she said as she smacked him on the ass.
She held him down with both of her powerful arms bracing for his reaction, lined up herself up and took one plunge as hard as she could into Jim’s ass, she finally fit in. Jim shouted in pain at the top of his lungs as Jane’s head had just barely fit in his ass and was nudging against his prostate.
“Now we have something to work with!” said Jane smiling and laughing at Jim’s pain. Inch by inch she forced her monstrous cock into Jim’s ass, Jim was helpless he could not escape, especially with something so large in his ass. Jane after a lot of effort had made her cock 4 inches into Jim’s as and as soon she stopped making progress Jim had shot off on Jane’s desk. Needless to say Jane was not happy.
“I tried to be a little considerate…but when I did…look what you did, you came on my desk! No more playing around time to get rough” said Jane in a frustrated tone.
“No! No! Please I didn’t meant to I’m sorry!” cried Jim
“Sorry your too late” Said Jane
At a faster pace than before she began to run her cock into Jim’s ass with no regard. Inch after inch, to Jim it almost felt as if the train that was Jane’s dick would never get all the way in. She had even begun pumping yet and Jim already had tears flowing from his eyes because of the pain. After a little while Jane realized she had hit a wall, she managed to get the majority of herself in, but no matter how hard she pushed she couldn’t seem to get the rest of herself in.
“It seems we have a stopping point here” said Jane
Jim was sobbing, bent over Jane’s desk, his knees had buckled and were touching each other, and his stomach was wet with the cum he had sprayed earlier.
“So since I can’t get all the way in I need you to help me out by squeezing the cute little ass of yours” said Jane to Jim as she gave his ass another smack.
Jim tried to clinch his ass tighter around Jane’s cock but it was simply to large and hard, Jim was almost debilitated with the thing in his ass.
“I can’t” Whimpered Jim
“Of course you can’t, you know, you haven’t done a lot right today…tsk tsk tsk its your first day too” she said with her cock still lodged in Jim’s ass
“Well I guess I will have to break you in today”
She started to get rough as she shoved Jim’s face flat against the desk as she slowly pulled her shaft out of his ass, leaving the engorged head still in. Then she forced her self back inside a little quicker. With a slow pace she began to fuck Jim. She moved her hips quicker and quicker as each thrust let her in a little deeper and went in a little smoother. And before he knew it Jane’s balls were clapping up against his butt as she vigorously fucked him. Jim’s hands were clinching the desk and nails scratching up against the wood, as he shot out another small load, making is situation more messy.
“You like that baby? Tell me how much you like my cock pumping in and out of your tight ass” screamed Jane
Knowing what would happen if what he said was not up to par he triad his hardest to appease her saying, “I love it when you big girly cock tears up my ass”
It sent Jane over the edge as her oversized member began to grow a little larger, and then spurt out shot after shot of her cum into Jim’s ass. Jim didn’t like the fact that she was cumming inside him but truth be told there was nothing he could do to stop her. Her head tilted back as a seemingly endless amount of cum poured into Jim’s ass. Once Jane had finished using Jim, she pulled out making him feel empty, as cum dripped out of him. She put back on her panties tucked her still wet and semi-hard member back under and slid her pants back on. She slid her shirt back on and smacked the lifeless Jim on the ass once more saying, “Good work today babe, see you tomorrow” as she walked out the room.