Toby stood at the photocopier. Watching it churn out reams of paper bored out of his mind. He didn’t know how the secretaries coped. He’d go absolutely mad if he had to do this all day. He wished his assistant Jenny was here. He would have much rather be sat at his desk watching her bend over to get more paper. Photocopying is about all she was good for anyway. She was incredibly stupid and terrible with computers; but the big positive was how she looked in a tight skirt and high heels. Which was the main reason Toby had hired her to be fair. So it was his own fault really; but what man doesn’t hire their assistant on looks over ability.

Annoyingly a few months after she started Toby had found out Jenny was a lesbian. And whilst that gave him incredible mental images to masturbate over; it meant he had no prospect of actually fulfilling his fantasy of fucking his sexy assistant. Still it was nice to stare at her arse as she walked around in sexy pencil skirts and very high heels and looking at her admittedly quite small breasts as she bent over the desk opposite him. She did make up for them by wearing slightly see through blouses and push up bras. So at least she made the most of what she had. She was hot and that was the main thing in an assistant.

Jenny had only been with Toby six months and so far he had refrained from coming onto her. Not because she was a lesbian but because he was still on a warning after his actions to his previous assistant. Lucy was just as beautiful as Jenny. And Toby had got into serious trouble for squeezing her arse and asking if she wanted to share a bed on a business trip they were going on. She then sued him, for sexual harassment. Luckily everything turned out ok, thanks to his Dad.

A little bit of background, Toby’s full name is Tobias Farquhar-Smythe, son of Hugh Farquhar-Smythe, owner of HFS Logistics, one of the world’s largest haulier companies and thanks to him Toby wasn’t sacked. However he was still not in his Dad’s good books. Which was why Toby wasn’t allowed to lead on this bid for the project with the massive retail chain.

That pitch was the reason why he was working so late this particular evening. The pitch was the next day and Toby had stayed late to help Rachel put the final touches to it. Everyone else had gone home but Toby had said he would stay and help her. Besides it was only going to be the two of them in the room for the actual pitch.

Therefore, as everyone else had left and sadly she was team leader, it was Toby that got to stand watching the fucking photocopier.

However, Toby had another reason to stay behind with Rachel. She was just incredibly beautiful. She had the most beautiful, soft face; gorgeous green eyes and lips to die for. Oh how he longed to kiss those lips or better still have them wrapped round his cock. She had an incredible body too; at the time she was wearing a tight black skirt that gripped her curvaceous hips and perfect, round arse. She also had great legs although she never showed them off. They were currently hidden behind some dark tights and she was wearing flat shoes which didn’t accentuate them or her bum at all. Toby would much rather have seen her in the ridiculous heels Jenny wore. This was the main problem with Rachel she was too prim and proper. She always had her dark brown hair in a tight ponytail and she always dressed conservatively. Although today she was wearing a tight skirt. She had a completely unrevealing polo neck sweater on as well. However, one thing she couldn’t hide, were her tits. Her tits were massive and that was the main positive she had over Jenny. Despite the unflattering jumper you could see the size of them bulging out from her chest. Oh how Toby wanted to rip that jumper off her, grab hold of them and squeeze them so hard as he pushed her onto her back and fucked her right on the desk. Anything to get rid of that disdainful look she always had around him.

For this was the last and biggest problem about Rachel. Since she had joined the company, Toby and her had got on like a mongoose and a snake. It didn’t help that she had joined just as the whole fiasco of Toby sexually harassing Lucy had come out. And being a massive feminist Rachel had not taken too lightly to this. Toby had also said some silly comments about her to a friend in the kitchen just as she had walked in. This led to them having a large row, where Toby ended up insulting her family and calling them common. Unbeknownst to him, Rachel that very weekend had been in an almighty row with her family over them perceiving her to be moving away from her roots with her high end job and this had meant that she had vowed never to speak to them again. However the comments about her family, understandably still upset her and this had proved to be the final straw and since then they had an extremely frosty working relationship.

However, as the top two salespersons in the company Toby’s dad had requested that they work on the project together; annoyingly with Rachel taking the lead. Something she had been keen to point out at every possible moment. Toby was sick and tired of it and couldn’t wait for this project to be over with. He was also determined to get back at her for making him do remedial jobs like photocopying just because she was team leader. So Toby had hatched a plan. He wanted to completely ruin her and take everything, and throughout this project, whilst contributing perfectly to the team. Toby had also been working on his own project. One that just involved him and Rachel!

Finally the photocopying was coming to an end. It was so late that literally everybody had gone home. Toby picked up the stack of paper and said goodbye to the cleaner, who was putting her coat on as he returned to the project area with the photocopies of the presentation slides and diagrams and whatever other bullshit Rachel had thrown in just to waste his time.

“Ah Tobias you’re back. Thanks for doing that, now if we could just run through the pitch one more time. Then we can go home”

Toby sighed. They had gone through the pitch so many times that he knew both his part and her part word for word. But Rachel was always like this the day before a big pitch. Toby sighed again and then started pitching to the empty office. A very surreal experience as the only response he got was a click of the air conditioning turning off. Eventually the fake presentation was over.

“Excellent, I think it’s going to go great tomorrow. Thanks for all the help tonight Tobias and sorry I’ve kept you so late.” Rachel said.

Toby cleared his throat. “That’s fine Rach (he knew this would wind her up) and please call me Toby (he hated the long posh name his dad had given him). Listen I just wanted to say something before we go. I know we got off on a bad foot. But I feel like this project we have both got to know each other a little better and I just want to say I’m sorry for all the times I have said something that has offended you. I just hope we can put that behind us and maybe be friends.”

“Thanks Tobias…Sorry Toby. That means a lot. Apology accepted. Also please call me Rachel. I hate abbreviations.” And for the first time ever she smiled.

“Great. I know this may be too far. But shall we hug it out.” Toby said spreading his arms. Rachel seemed reluctant but to Toby’s surprise she stepped forwards and put her arms round him. Toby loved it; it felt good to feel her large breasts pressed against his chest. After a few seconds Toby started to pull away and Rachel removed her hands from his back. However Toby did not do the same. He kept his right hand on the bottom of her back and pulled her against him; whilst he moved his left hand to the back of her neck and leaned in to kiss her. A look of shock appeared on Rachel’s face and at the last minute she turned her head so that Toby only kissed her cheek. Rachel then started wriggling violently and broke Toby’s grip and backed away.

“What the hell are you doing?” She shouted. “I mean what the fuck? You stupid arrogant twat! Why the fuck did you do that? Just cos we seem to be getting on slightly better, that does not give you the right to try and kiss me! I’m going to tell your fucking Dad and you’re going to be out of this fucking company, you fucking prick!”

Toby let her rant and rave; it was nice to see a bit of energy and passion in this normally so calm and restrained person. “I’m not going to rest until you are sacked, you posh twat.”

Toby’s hand shot out so fast, and his palm connected with the side of her face with a crack; sending her flying sideways into a chair.

“Don’t you ever call me posh you fucking bitch.” Toby screamed towering over her. Rachel stared up at him clutching her stinging cheek; tears forming in her eyes; there was hatred in those eyes too. “You’ve treated me like shit ever since you joined this company. I’m fucking sick of your attitude and thinking you’re better than me, because you’re not. My Dad owns this fucking company in case you didn’t know, and I think it’s time I taught you a fucking lesson.” And with one quick movement he grabbed her arm and dragged her out of her chair.

“Oi, what are you doing?” she shouted “Get off me!” He continued to grip her arm and pulled her wrist behind her back and slammed her face first onto the desk. Luckily for her, her breasts gave her a nice soft pair of cushions to land on.

“Please stop. What are you doing?” Rachel screamed. She was wriggling trying to get away, so Toby placed a hand between her shoulder blades and pinned her to the desk. She twisted and turned trying to get a hold of his hand, but her arms just didn’t bend that way. Toby pressed on her back harder, inflicting greater pain as he crushed her spine causing her to try even harder to get a grip to release the pressure on her back.

However she was soon distracted by the noise of his other hand unzipping her skirt, and immediately switched her focus to grabbing the waistband.

“HEEELLLLLPPPPPP!” She screamed. Now Rachel was really wriggling. And the more she did the more difficult it was to keep her pinned. Toby raised his hand and spanked her arse hard, a number of times. She squealed in pain at the shock of the attack. This subdued her for a while.

“I would have thought you would have realised by now that no-one is going to help you. We are the only ones in the office.” Toby cackled as Rachel sobbed in pain, her arse throbbing. With her subdued he quickly ripped her skirt off and let it fall down to her feet. He then gripped her boring black tights and tore at them to reveal a bright red hand print covered arse cheek. Toby felt slightly guilty for hitting her so hard; but at the same time felt a stirring in his groin. In fact, he didn’t really feel guilty at all. Besides she had to get used to the pain.

Toby thought she had stopped fighting but he could feel her body still straining. And then he realised what she was up to; he had released her arm to rip her tights and she was now stretching it out across the desk, for sticking out of a pencil holder, was a pair of scissors.

“Great idea, Rachel. These will make taking your tights off much easier.” He said snatching them up; and then proceeded to tear and cut at the tights until they were just a pile of shreds on the floor.

At one point in his haste, Toby accidentally caught Rachel’s leg with the blade of the scissors, causing her to cry out, as a trickle of blood ran down her hamstring.

Rachel’s whole body language had deflated after she had not picked up the scissors, she had seen that as her chance, but now it was in Toby’s hands and her tights were shredded she was losing her fight, especially as she now only had a very boring pair of white underwear on her bottom half. With two quick snips of the scissors these joined the pile on the floor. Rachel started to sob even harder now, she was completely subdued with her naked bottom half, and Toby holding a sharp pair of scissors. However Toby liked a bit of fight, and so he flung the scissors across the room and proceeded to rub his hand over the outside of her cunt.

“Please stop.” She whimpered. “I’ll do anything you want. Just don’t rape me!”

“I think we are bit beyond that Rach. And at the minute the only thing I want is to stick my cock in your sexy arse.” Toby said giving it another spank.

“M…M…My arse! Please no! I have never…”

“Well that is very interesting. You’ve never been fucked in the arse before?” He said, feeling his cock harden at the thought. He started unzipping his trousers, pulling them down his legs.

“No” she cried.

“Well it looks like I’ll be taking your anal virginity then” He goaded pulling his boxers down to allow his rock hard cock to spring free. However as he did this, Rachel saw her chance. With his trousers round his thighs, Toby had limited leg movement and had also released the pressure he had been applying to pin her to the desk. So she wriggled out from underneath him and attempted to run for the door.

However she had forgotten about her skirt still balled up around her feet, and as she tried to flee her foot caught in it and she stumbled. This gave Toby the perfect opportunity. He dived and wrapped his arms around her ankles sending her tumbling to the floor with a thump. He then immediately jumped on top of her and sat on her back, pinning her to the floor. She wriggled greatly, but he wasn’t budging. He calmly took of his shoes, trousers and boxers. He wasn’t going to make that mistake again. If she was going to run again, Toby wanted to be free to chase after her. He also rolled a condom onto his dick; to protect his cock from her dirty shit.

Toby then stood and scooped her up and slammed her unceremoniously back onto the desk. He then gripped her hair tightly and pulled her head right back. She screamed as the hair yanked at her scalp. Toby bent over, his face right up against hers and hissed in her ear.

“Don’t you ever try and run away again! If you do, there will be dire consequences. Do you understand?”

“YESSSSS!” She screamed, as the pressure he was applying to her head was threatening to tear her hair out.

“Good” he said releasing her hair causing her head to jerk forward and bump hard into the solid wood.

Toby then positioned his cock, in the gap in her arse cheeks. She desperately tried to stand on her tip toes and raise herself up so his cock was in line with her pussy.

Toby found it highly amusing how she had now resigned herself to being raped she was just trying to choose the hole. But Toby only had one intention, he’d never taken anyone’s virginity before and the fact it was her anal virginity, turned him on even more. So he gripped her hips and held her in place and then pushed his cock between her arse cheeks. She froze as the tip of his cock came into contact with her sphincter. Toby paused for a second savouring the moment, and then pushed forward. He pushed hard but she was clenching it so tightly he couldn’t get it in at all. The harder he pushed the tighter she clenched, until in his frustration Toby spanked her arse. He felt the soft flesh compress under his hand and watched the red mark blossom from beneath his palm. God that turned him on; however the spanking also had another effect, for as Rachel jumped in shock and pain, her arse muscles loosened slightly. So Toby raised his hand up again and this time as he brought his hand down, he thrust forward hard. Rachel’s yelp turned into a scream as Toby’s bellend buried itself inside her; stretching her previously un-entered arse.

Now although Toby would only classify his penis as average sized, it was still considerably larger than any shit her dainty little body had ever produced and so the feeling of his hard, unforgiving rod entering her tight virgin ass must have felt like it was being torn in two. Toby pushed deeper until her clenching arse muscles meant he could go no further. He pulled out slightly, then spanked her again and thrust forward pushing himself deeper inside her.

Toby looked down to see her ring gripping his member; he could just see the curve of the bottom of his bellend poking out of her. He thrust again. She was so tight, he could only get about a quarter of his 7 inch cock inside her, before he could go no further. It felt unbelievably good though. Her arse was gripping his cock like nothing Toby had ever experienced before. It was so much tighter than a pussy. He enjoyed the way she gripped it, squeezing him harder as she tried to stop his advances and unintentionally making the experience even better. This had the effect of turning Toby on even more and if possible making his dick even firmer. He continued to spank her and with each spank thrust deeper inside her. He’d then pull out of her, before spanking and thrusting again. And with each thrust his cock entered further and further inside her. Rachel was screaming in agony as Toby’s cock plundered her, splitting her in two. To her it felt like there was an elephant’s trunk being shoved up her.

After a while the progress got easier. Her ass was starting to adjust to the width of Toby’s member and the muscles were starting to loosen their grip and pull him inside. She had also stopped screaming so much and it had been replaced with a series of sobs and moans. With her muscles adjusted, Toby could slide in and out of her more easily. He started to up the tempo and started to pound into her arse. The screaming started again as his cock pummelled her against the desk, sliding against the tight walls of her ass, ripping past them. Toby’s cock was now fully buried inside her; every time he thrust forward he could feel his balls slap against her cunt. He was so turned on; the combination of her pubes tickling his balls and his cock sliding in and out of her tight arse, was bringing him very close to orgasm. Toby put his foot on the edge of the desk, allowing him to pound her even harder. Rachel squealed and cried as he punished her brutally, ripping her arse as he rammed into her. Toby grabbed hold of her ponytail and pulled her ass onto him as he thrust forward.

He wanted her to feel like a worthless, pornstar slut; because to him that’s what she was and he was treating her like it. He fucked her ass like an animal. Doing whatever he liked to her. And soon the constant pace and pressure meant that he could hold back no more. The sensations rushed through him, running from his cock up, along his nerves and into his brain. He could feel the blood rushing along his arteries, down from his heart, along his groin, and into his swelling cock. Causing it to pulse as the pleasure rushed through his whole body. Then as Toby thrust forward one last time, and his cock slid the length of her asshole and her pussy lips kissed his testicles, Toby could not hold it back any longer. His cock exploded like a grenade inside her, expanding and stretching her ass even further. She bawled in agony and humiliation and to further this, Toby placed his foot on her head, pinning it to the desk. This degraded and demeaned her even more; she felt so used and worthless as Toby thrust the last bits of sperm into her helpless body.

When Toby was completely finished he slowly slid his cock out of her arse. Rachel collapsed onto the desk in exhaustion and relief as Toby’s cock finally pulled clear. She lay there completely degraded, her body aching all over. Toby looked down at his softening cock, he could see the white cum beneath the thin condom, but was shocked to see the outside was covered in red blood. He gently pulled it off and tied a knot in the end so as to keep any evidence inside. No wonder his passage had got easier, her blood had acted as lube. He had clearly torn her ass as he raped her. He felt slightly sorry for her. That would be the end of the pain for now. But Toby wasn’t done; he wanted to completely humiliate her too.

Toby left her there whilst he started to get dressed. He pulled his trousers up and put on his jacket. He then pulled a digital camera out of his pocket and took some photos of her, still slumped on the desk; her plundered ass poking up beautifully in the air. He snapped some close ups of her ass and pussy and then Toby unzipped his trousers, to get some photos of his cock between her ass cheeks. Her whole body seized up, thinking he was going to fuck her ass again. And Toby could see it relax again as he pulled away.

“Get up!” Toby ordered. Slowly she pushed herself up off the desk and clutched her throbbing ass as she turned to face him, tears pouring down her face. Her eyeliner was running terribly. Toby gave her some tissues to wipe her face with. Eventually she started to recover.

“I…I…I can’t believe you just r…r…raped me” she stammered. “I hate you! I’m not just going to get you fired. I’m going to go to the police and you’re going to go to prison.”

Toby laughed. “I’m tired of your threats Rachel. I knew it might come to this. I knew you wouldn’t just give in and submit to me. And to be honest I liked you fighting; it was a massive turn on. But I thought I better bring some insurance for this very moment.” And he reached into his pocket and pulled out a shiny metal gun. Rachel jumped back, gasping in fear. She backed up as Toby advanced on her, until the back of her legs were pressed against the desk. Toby advanced until he could feel her breath on his neck and then calmly placed one hand on her breast, and pressed the gun to her temple, before whispering in her ear.

“You are going to do everything I tell you! Or I’ll blow your fucking brains out! Ok?” Rachel nodded nervously. “Good” Toby hissed menacingly. He then stepped back and surveyed her up and down.

“Firstly I want you to remove that polo neck. And make it sexy. Well as sexy as you can with a polo neck.” Toby joked, surprisingly casually considering the situation.

Rachel nodded and slowly she started to sway her hips as she pulled the polo neck seductively upwards; revealing her perfectly toned body. Eventually the bottom of her bra came into view and as pulled it up over her head, so did her cleavage. She leant forward to give Toby a better view. She was wearing a boring, plain, white bra, which was a bit of a let-down; but Toby still got some good photos.

“Great! Now kiss me!” She looked shocked and Toby knew she was about to complain.

“Uh uh.” He said showing her the gun and shaking her head. “Don’t even think about protesting. I hold all of the cards. Now come over here and give me a kiss. Oh and make it passionate!” He instructed. She shook in fear and disgust, but placed her hands on Toby’s cheeks and pulled him to her lips. It was incredible. They were full, soft and moist. Toby savoured the feeling of her warm breath; he slid his hand down her naked back and onto her bum. She winced in pain. But Toby didn’t give her time to dwell on that as he pulled her close and slid his tongue inside her mouth. She closed her lips round it. God she was a good kisser. He nearly forgot to photograph the occasion but did manage to take a few snaps and then stepped back.

“That was very good” Toby said. “Now I want you to finger yourself!”

“What?” She exclaimed.

“You heard. I want you to finger yourself. I need some incriminating pictures. Now put your fingers in your cunt or I’ll put my gun in there.” Toby said twirling the gun round his finger menacingly. She sighed, staring at the gun in fear and then started to rub her pussy. Toby took a few close-up snaps. She had started crying again, so he rummaged in her bag and pulled out a make-up wipe and proceeded to wipe her tear stained face. She looked so much more beautiful now.

Rachel began by pressing against her pussy, rubbing the outside. She then slid one finger between the lips and ran it along the parting. Rachel started to gasp as she started to pleasure herself. She then spread her pussy lips further and began rubbing her fingers over her clitoris; then with Toby’s encouragement she slid her finger inside herself and gasped in pleasure. She tilted her head back as the pleasure rushed through her, as she aroused herself. She looked back at him, clearly starting to enjoy herself, and that couldn’t be allowed.

Toby took a couple more photos then ordered her to stop. However she didn’t. Rachel was too caught up in the moment. She was actually moaning in pleasure. Toby quickly switched to video. Before stepping up to her and pulling her hand away himself.

“I said stop!” Toby hissed. “You can’t cum unless I say you can! Got that?”

Rachel nodded; disappointment stretched across her face.

“Good girl” he said, pulling her to her feet and slapping her bum causing her to squeak in pain.

“Right now get dressed!” He ordered and she bent to pick up her skirt. Then Toby caught sight of the condom and had a better idea to humiliate her further.

“Actually! Stop! Give me your clothes!” And she handed over her jumper, skirt and shredded pants. “And your bra!” She reached behind her and unclipped her bra, putting it in his arms with everything else.

Toby then put the clothes down on the desk behind him and picked up the condom; still completely full of his juices and handed it to her.

“What am I supposed to do with that?” She inquired, looking at in disgust.

“You are going to drink it” Toby ordered.

“What? That’s disgusting.” Rachel howled in horror.

“Yeah it is. But you’re still going to do it or I’ll shoot you in the head. And you’re going to make it sexy!”

Her head drooped. “Ok” she mumbled, Toby couldn’t believe it. She then looked at the condom and then at Toby. “How am I supposed to make it sexy?”

“Here let me help you. Stand side on to me!” Toby took a photo of her naked curves. Then he photoed her sexy abused bum.

“Right now put your hands on your hips and look sexily over your shoulder! Oh and hide the condom behind your other hip! But don’t spill any!” She did a sexy look over her shoulder, faking a smile.

“Now wink!” She did. This was Toby’s favourite photo of them all. This stunning woman standing completely naked; her breasts sticking out in front of her and her arse sticking out behind; as she winked seductively. It was something straight out of a porn mag.

“Very nice. You are so fit. Now tilt your head back!”

“Good, now open your mouth! Put the condom to your lips, tip it up and swallow the contents!”

She gave one last scowl and gulped nervously. Then she leant her head back and put the end of the condom between her lips, so that it drooped over her chin. Then she pinched the end and lifted it so that the sperm trickled out and down her throat. Toby could see her swallowing. He got some great shots. It was a surprisingly sexy look. She struggled to keep up with the stream of liquid flowing out of it. Toby had produced a lot. She started to gag. Toby was scared she was about to throw up over the office, but through sheer willpower she kept it down and managed to swallow every last drop. When she was done swallowing, she pulled the condom down and glanced at Toby hoping he was done with her. He was for now.

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