Reward Challenge

All comments and feedback are gratefully received as I'm hoping the feedback will encourage improvements in my work. This is a work of fiction from the deep dank recesses of my mind and any resemblance to real people is purely accidental.

This story depicts group and anal sex, if this not to your liking, please visit some of my other submissions, otherwise I hope you enjoy.

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Craig had been called into the big boss's office which was a rarity in itself that made him wonder what was afoot. He hadn't done anything to anger the grownups, or so he thought, on the contrary he had come up with a new process for how his colleagues did things that would provide benefits for months and years ahead. He tapped on the door and could hear Jim from the other side say loudly "Come in." As Craig stepped into the office Jim stood from behind his desk and stepped around the desk holding his hand out to shake "Thank you for coming. I appreciate it was a little last minute and at an odd time" as he pushed the door closed, he offered Craig a seat as he resumed his adding "I really wanted to say how much, myself especially but the Board as whole, really appreciate that idea you came up with. It will deliver sizable benefits for some time and as people outside the organisation get to hear about it will deliver significant benefits in both our reputation and our ability to raise funds going forward."

Craig sat back in his chair a little stunned to hear such praise first hand and could only reply "It's a pleasure to have come up with the idea. I like working here and want to do what I can for an organisation that gave me a job when others disregarded me."

Jim smiled easily and replied "Well their loss is our gain and I want to express in the strongest terms how much we value your efforts. Now as you'll know trading is a little tight at present but your process will show real benefits in the medium and long term and the Board want to ensure you benefit on the back of it and so we've instructed HR to draw up a new contract for you that sets out an improved benefits package."

Again, Craig looked stunned and could only muster "Thank you" as a reply.

Jim then leant forward again and lowered his voice saying, "I want you rewarded in the short term but we can't afford to award a pay rise just yet and so I've come up a solution that also addresses a problem I have elsewhere if you are willing to follow orders."

Craig's mind was really buzzing now as he had no idea what the reward could be that isn't a pay rise and replied "Of course, as long as it's legal of course."

Jim held up his hands in submission and confirmed "I can assure you it's legal, I believe it will be a very unique award that you will remember for years to come." Craig felt even more like Alice looking down that rabbit hole at this point as Jim continued "Now I'm led to believe that you have no romantic ties at the moment, is that correct?"

'Where was this going?' Craig debated as he spoke his answer "No, I'm too young for that stuff yet."

"Good" replied Jim, "Now can I ask what your opinion is of a young blond lady we have working in Sales?"

"Errrm... I errrr" Craig stumbled, not quite sure how to phrase that she was a hottie of the first order and completely out of his league but what was the context of the question in relation to him being single.

Jim held his hands up and broke the discomfort "No, let me re-phrase that. Do you think she's attractive?" Craig did and mutely nodded "Good" continued Jim "Would you say she is sexy?" After a moment's hesitation Craig nodded again without saying anything. "And finally, would you consider her your type?"

Craig finally found his voice and replied, "At present, any type is my type but she's a bit out of my league I wouldn't know where to start talking to her." 'Is this what he wants to hear?' thought Craig.

"That was the perfect answer" beamed Jim as he clasped his hands together "In that case then I have the perfect reward for you. Now I've asked Ally in for a meeting in a few minutes and I want you there. It is a very unorthodox meeting and I need you to do exactly as I say when I say it. Can you do that for me?" Craig was back to nodding again but Jim pressed on "Before we start this, I need to make sure you are 100% bought in and you will follow my every word but I guarantee you will never have a reward quite like this one."

'What the hell had his reward to do with finding Ally sexy?' but still he answered "Yes, I can do that as long as it isn't illegal."

Jim was back to his charming self, "Rest assured there's nothing illegal going on." Just then there was a knock at Jim's door to which he raised his voice to say "Come in."

The door opened and the pretty blonde popped her head around the door and on seeing Craig said "Oh, sorry I didn't appreciate you had company. Am I too early for our meeting?"

"Not at all" replied Jim as he waved his hand to his other visitor chair "Craig is part of the discussion."

Ally's senses prickled at that little nugget 'Why have I been called here at all and what does this youth have to do with it?' Ally was usually very sure of herself; inhabiting the Sales world required a certain amount of bravado, but this invite had unsettled her. She had a ready smile, stood around the 5 8 mark, was rightly proud of her curvaceous figure and either wore her blonde locks down or in plats which was today's option. She took the offered seat and waited for Jim to begin.

"Thank you for coming to see me. Sadly, I need to have a word with you regarding your last Quarters figures" Jim started the discussion with.

Ally's heart sank at his words. She had agreed to a rather bullish target last quarter but between a holiday and a few unfortunate deals that slipped through her fingers she was well down on her target. She decided to go on the offensive by stating "I agreed to that target as I wanted the job that you offered Derek otherwise my performance has to be judged on my two previous quarters especially as I was on holiday for some of the time."

Jim smiled expecting the comment and answered "Well, we discussed the target at the time, and you agreed to be held by it and so here we are. Now what would you say if I told you Derek was going to be side-lined and therefore that role will be coming up for offer once more."

Ally was shocked at this as she assumed Derek would be there for the long term, but it gave her hope "If that is really the case then I will do absolutely anything to secure the role. You name the target, and I will hit it out of the park."

Jim leant back in his chair as he waved his hands "Not so quickly young lady. There are two other individuals that could be also considered, and you've missed out on your chance to gloss over this with optimistic words. This is now the time for determined action." He stressed the point by hammering his desk with his finger a number of times "If you want this job, you have to demonstrate your determination with actions rather than words."

Ally realised her bluff was being called and decided to take the challenge. She stood up and leant over the desk as she stated "I'm having this job. You know I'd be good at it, and you know I'm the perfect candidate. Just say the word and I WILL demonstrate I'm your perfect candidate."

Jim was still leant back in his chair thinking 'Bingo, she has walked straight into the trap.' He shrugged and said "Prove it. If you want this job show me how much and remove your blouse."

Both Ally and Craig were looking at him with a similar stunned expression as the woman asked "Did you just say... "

Jim held all the cards and cut across her "You heard me correctly. If you want the job remove your blouse for me otherwise clear your desk and you're out the door." Ally turned and looked at Craig and so Jim shut her down there also "Don't look at him. I'm the one making the decisions around here but if it calms you, this man here has come up with a revolutionary idea that will save this company millions in next to no time. You on the other hand have so far been a drain on our resources with little to show for it. Strip or get out."

Ally looked from Jim to Craig and back again. Craig still resembled a rabbit in the headlights, Jim on the other hand had the look of a puppet master. Ally managed a stuttered "But... I... I" Jim's look of raised eyebrows silenced her in a heartbeat, and she stood up straight, 'He's left me no wiggle room' she debated to herself but could only see one option. This was her choice and her chance to seize the initiative. Ally pulled her blouse out of the waistband of her skirt and began to pop the first button before stating "I want to ensure that me doing this gets the job without any further 'Tests' from you?"

Jim smiled back "Absolutely. Do exactly I say while you are in this meeting, and I will guarantee an announcement to the company by the end of today. Craig you are here to witness I made that guarantee and if I don't carry that out you must report this to the board." Craig just nodded mutely.

"How far do I have to go?" asked Ally.

Jim hadn't altered his posture and reminded "I said do EXACTLY as I say while in this meeting and you WILL have that job. How much do you want it though?"

'Challenge accepted' thought Ally as she said "This much" as one by one the buttons of her blouse were undone to the hungry stare of Jim especially. The blouse was opened and pulled from her shoulders to reveal her white lacy balcony bra showing her reasonably sized tits off rather nicely. Jim hadn't coaxed her any further but without a moment's pause she reached behind her and drew the zip of her skirt down which slid down her legs with the aid of a little shimmy of her hips. She stood before the two men's gaze with her hands on her hips in just her bra and panties, still determined this was a Jim bluff.

Jim's admiring glances intensified when she performed this latest removal without the need for prompting. "He twirled his finger around and said, "Turn around for me." As she did as he had requested Jim turned to Craig and asked, "What do you think?"

Ally stopped the next turn facing the young man and he looked up her body to her pretty face and spoke with a slightly hoarse voice "Errrr, very nice. Very nice indeed."

Ally continued her turn to stop in facing Jim and waited expectantly as he considered her body "Yes I quite agree, very nice indeed although I think the bra needs to come off next."

'This was it' thought Ally. 'If I go ahead with this, I fully expect Jim is looking to fuck me but what about Craig. Is he here just a witness? I suspect not. How much do I need this promotion?' "This guarantees I get the promotion?" she asked.

"It is yours, just a few more instructions to follow and you can start planning how to shape your team and what to spend the raise on" was Jim's reply.

That did it, Ally reached behind her back and unclasped her bra. She bunched her shoulders so she could work the straps down her arms and then pulled the garment clear as she half turned and draped it over the nearest of Craig's shoulders. His senses were assaulted by the smell of her perfume on it, how warm the garment was and how spectacular her breasts sat on her chest. For good measure Ally rubbed both breasts in her hands to work off the red impression of the stitching of her bra. She allowed Jim a few moments to admire her rack before she worked her thumbs into the waistband of her panties and then pushed down, crouching to push them clear down to her ankles.

As Ally stood back up, she placed her hands on her hips and asked, "Now what?"

Jim didn't answer immediately but then said "Now you carry on taking my orders. Lean over towards my desk." Turning to his other guest he asked "Have you ever eaten pussy" another wide eyed nod from Craig as he watched her bend at the waist. "Good, kneel behind her and lick her pussy for me."

Ally altered her stance to make Craig's job easier. The removal of her bra had committed her down this path and she was determined that she would enjoy it as evidenced by the slight damp patch on her panties. Craig lost no time in sliding from his seat and shuffled on her knees behind her. He extended his tongue as far as he could and drew it along her deep pink labia which elicited a shiver and groan from Ally as she wiggled her hips by way of encouragement.

Jim leant forward in his chair and captured her dangling breasts in both hands as he asked, "Is he doing the required job back there?" while tweaking her nipples between his fingers.

Ally closed her eyes as she luxuriated in the attention from both men. It had been some months since she had been on the receiving of any action and so they were effectively pushing against an open door. "Mmmmm, yes. He's doing very well; you both are. It gives me quite a buzz getting this kind of treatment from two men."

For his part Craig was still pinching himself. He had admired Ally from afar when either was walking around the office and never imagined he get to see her naked let alone lapping at her juiced up pussy. He mulled over his good fortune 'This is certainly one hell of a bonus that Jim has arranged. Stick your extra pay if sweet pussy is on offer in the office.' His tongue began to progressively quest further as once again Ally spread her stance so that he had an easier access to work his tongue deep inside. He had a way of dipping his tongue in and out of her before he then swirled his tongue around deep inside. He loved the way she tasted but he kept extracting his tongue so that he could take her enflamed clit between his lips to suck hard on the nub.

Ally was really getting into Craig's mouth and was tempted to say he had a better tongue than her past lovers could ever muster but instead just kept pushing her pussy back into his face to encourage him to search deeper. Jim let go of her boobs and stood up unbuckling his trousers. It didn't take a genius to work out what he was after and after kicking them off his feet he stepped around his desk to present his cock for Ally's mouth. She half turned in his direction and took him as deeply in her mouth as she could. She wouldn't say anything but actually felt a bit cheated at being presented with such an average cock, but she did the dutiful thing hoping that the promotion was hers.

Jim was enjoying her mouth but wanted something different as he took a seat in one of his visitors chair he instructed Ally "Come and sit on this, I want to feel that pussy of yours." As soon as she had taken him inside Ally started to bounce on his cock figuring it the best way of getting him off. Jim then turned to Craig who was still knelt wiping her copious juices from his face "I think you deserve a suitable reward for getting the lady suitably revved up. Get your dick out and try her very talented mouth."

Craig wasn't about to look that particular gift horse in the mouth and quickly shed his own clothes. As soon as his cock came into view Ally's pussy gave a little twitch. For all her disappointment at the boss's cock, Craig more than made up for it in both length but especially in girth.

Ally lunged forward and engulfed him in her mouth starting to suck longingly along its length. She liked wrapping her lips around a good cock and this one she figured would easily be ringing her bells. Craig hadn't had that many blowjobs but the treatment his cock was receiving now was setting a new benchmark from which he would judge future ones. Ally liked to pull her lips back slowly feeling each ridge and bump of his cock and swirling her tongue around the head just before she dipped forward once more to take him back into her mouth.

Jim was too self-absorbed in having her snug pussy ride his cock to feel any jealousy at his rival's equipment. Instead he just grabbed Ally's hips as she kept rising along his cock until he held her still so that he was buried in her pussy when his balls let go coating her insides. This was the result she was hoping for so that she could push Craig back against the desk, have him perch on the edge so that she could clamber up and start to feed his dick into her.

Now this was a dick she was going to enjoy. As soon as the head was engaged by her muscles, he stretched her better than any previous lover plus when she started to rise and fall along his length, she inched a bit more inside her until he was navigating into new territory never visited by another cock or her extensive collection of toys.

Craig just sat there enjoying the way her pussy gripped and pulled at him, he figured he wouldn't last too long but his fate was sealed however when she leant forward and offered up one of her breasts for him to suck on. The rubbery nub felt good between his lips, and he sucked on it in the same vein has he had with her clit making her gasp and groan increasing the volume with each mini orgasm that triggered inside her. Eventually though Craig was rewarded by her pussy gripping at his length as she came from her exertions. The feeling of her pussy releasing even more juice around his cock really was something he would never forget.

Jim had guessed from her groans that she was about to come and decided to put the final part of his plan into action. He walked over to his desk draw and extracted a tube of lubricant. In next to no time a decent amount had been applied to his cock and as Ally stopped her riding while her climax hit, he positioned the head of his cock at her sphincter and pushed forward. Ally made an appreciative groan, which Jim took to be a reaction to receiving a cock in her butt. The reality was that she was no stranger to taking a cock there, although she would admit to it being sometime.

The enjoyment was actually down to feeling two cocks inside her at the same time, she had only felt it once before but this time she had the added bonus of having Craigs cock lead the way. The size of Jim's cock meant that she could accommodate him quite easily although she would admit later that she was surprised he could rejuvenate his cock so quickly after he had come not so long ago.

What really rocked Ally's world was when the two men alternated their thrusts and as Jim was pulling back, Craig was trying to cram his cock back in her -- or as best he could as Ally was actually doing most of the driving. Occasionally their timing was off, and she'd feel them both thrust in her at the same time and this latest occurrence eventually triggered a chain reaction. It sent Ally into a deep groan and as her pussy gripped Craig one too many times he let his come fly while he was buried deep in her pussy -- the volume of which she certainly appreciated after Jim's first climax. Speaking of Jim, her squeezing butt triggered his come and he held still as he spewed his come inside her butt.

Ally lay slumped against Craig as Jim pulled out of her abused butt and staggered back to pull his trousers back on. Ally slowly disengaged her pussy from Craig's cock -- as slowly as she could because it felt good inside of her -- and they too in turn get dressed while Jim waited sat in his office chair. Turning to Ally he pronounced "Well young lady Welcome to the upper echelons of the organisation. I have high hopes for you and your future here." Turning to Craig he added "And you young man, I hope that proved to be a suitable reward for your efforts."

Craig had the good grace to blush as he acknowledged "It certainly was."

Craig left the office still trying to process the last hour but hadn't got too far when he heard Ally call from behind him say "Hang on, I want a word with you." He stopped until she caught with him and she steered him into a nearby office that was empty. She closed the door and pushed him back against the door point an accusatory finger at him "So what does Jimmy boy have on you?"