Pegging For Promotions

Doug was less than five years out of college, only in his late twenties and had already started one of the most successful businesses in his city. It seemed as though he had made every right decision since leaving school. That is, until he decided to hire a personal assistant.

There were a number of qualified candidates, but when Melissa walked into his office, he was almost hypnotized. She was young, had just turned twenty years old, tall, and tan with a thin but athletic build, her breasts were small B's and her clothing was somehow professional but provocative. When she shook his hand, she caressed his wrist with her left hand, looking seductively into his eyes, he was hooked.

After what could barely be considered an interview, Doug said, "I think you'll be a good fit for this position."

Melissa produced a big smile, and said in an excited and bubbly tone, "You won't regret this sir!" giving a cute little salute to accompany her words. And with that she left, as Doug sat back in his chair, he smiled, and thought about how nice a little eye candy in his life would be.

Unfortunately, within a week, Doug was regretting his decision. Between Monday and Thursday she had arrived late and left early every day. She barely did any of her duties, and he suspected she was stealing from the petty cash account. When Friday afternoon came, he specifically asked her to stay until five, he shouldn't have had to of, but he did.

Doug waited until the last employee had left and it was just Melissa and he. Having never fired anyone before Doug was nervous as he called Melissa into his office. She was wearing a low cut top and a small skirt, and carrying a large purse when she came in and took a seat. "What's up boss?" she asked almost oblivious to what was coming.

"Um, well Melissa..." he struggled to find the words, "I am afraid based on your performance I am going to have to reconsider your position with our company."

Melissa rolled her eyes and let out an annoyed sigh. She got out of her chair and came to the side of the desk before dropping to her knees. "Come on," she motioned for Doug to get up and lean on the side of the desk before her.

Doug stammered, "Melissa, what, what are you doing? This really isn't appropriate."

Melissa again sighed, "Look, we both knew this was coming, I really can't lose this job right now, and so will you come over here and let me take care of you, I really don't feel like working at the strip club again." She knew exactly what she was doing as she adjusted her breasts and licked her lips, alluding to herself undressing.

Thinking with his cock had gotten Doug into this mess, and repeating that certainly wouldn't get him out of it, but he couldn't help himself looking at her on the floor. He rose out his chair and took his position before her, hastily undoing his pants, shoving them along with his boxers down to his ankles.

Melissa sprung to his crotch; she ran her hands along his thighs, gently kissing around his cock, taking care to not actually make contact yet. She took his cock in her left hand and began to suck on the middle finger of her right. She removed it, drenched in saliva and reach around him. She looked up, into his eyes with a wicked smile, as the tip of her fingers touched his asshole and he instinctively clenched.

"Relax," she said in a cool tone, "I am going to make you cum like never before, you just have to trust me." When she finished talking she began to nuzzle the base of his cock with her closed mouth, she had no intent of actually blowing him. Doug was past the point of reluctance and did his best to relax his asshole as Melissa's finger bore into him.

Melissa's skilled hand found his prostate quickly, and as she encircled it with the tip of her finger Doug's cock stiffened like it never had before. Between his throbbing member in her hand, the evaporating resistance from his sphincter, and the look on his face, Melissa knew she had her boss right where she wanted him. "Here, turn over," she instructed him as she withdrew herself from him, and popped up to get her bag.

Doug was in a daze, his dick was harder than he ever thought possible. The new sensation of having his prostate massaged left him speechless; literally, he went to speak and had no words. He simply turned and bent over the desk leaning on his elbows exhaling sharply awaiting Melissa's attention.

Meanwhile, Melissa had withdrawn a few things from her bag; she was indeed prepared for this, and knew just how to handle the situation. Standing before the desk she made a bit of a show of putting on a black latex glove over each of her hands pulling them taught before coating the middle and index fingers of her right hand with a small vile of lube she had.

As she walked behind him, Doug finally mustered the ability to speak, "Melissa, I..." is all he got out before again her left hand was grasping his cock and the fingers of her right were working their way into his asshole as she took position behind him. With no instruction, he widened his stance, allowing easier access to his anal canal.

"Good boy, you're a fast learner, and I have a few more lessons to teach you." With that she again found his prostate, this time trapping it in the slight divot between her fingers, with a gasp Doug's head shot up, she knew she had his full attention. As she gently worked his man-clit, she began to tell him, "I don't think I'll be going anywhere except up at this company, and from now on it's Miss Melissa, understand?"

Doug was nearing orgasm; no one had ever touched him or controlled him like this. "Yes Miss Melissa, I understand," Doug released in a breathy tone amongst his moans. At his acknowledgement, Melissa again withdrew her fingers, sensing he was close, not wanting him to finish just yet, and returned to her bag.

After rifling through it briefly, she brought out a strap-on harness with a small purple dildo in it. Doug's eyes grew wide as his saw the rubber cock, as he had a good sense of where it was going, he began to protest, "Melissa, uh, I mean, Miss Melissa I don't think I am ready for this, I'm mean this has been fun but..."

Melissa again simply ignored him, and his pleas. She returned to his back side lubing the dildo as she walked, a wicked smile growing on her face, she knew just how to shut him up, dropping her purse on the desk. She brought the tip of the dildo to his spread asshole, all pretext gone she inserted it fully, cooing at Doug, "There we go, not so bad, is it?"

Doug moaned in response, cutting off his sentence, he had been brought so close to orgasm that any stimulation was welcome. He exhaled deeply, as he felt Melissa place one hand on his shoulder and the other on his hip; she found a good rhythm with her hips as she steadily fucked him up the ass with her cute little purple dildo. She tugged at the fabric of his shirt, after a few solid thrust into him, she let the toy slip out of him, "Take this off, and sit on the desk, I want to look into your eyes while I make love to you."

Doug readily complied, he had never been controlled like this, but he took to instruction like a fish to water. When he was completely nude and sitting at the edge of the desk Melissa, still fully dressed, returned to him, she reinserted the dildo fully, and stared deep into his eyes. Doug met her gaze momentarily before she leaned in and began to passionately kiss him, never ceasing the motion of her hips humping that dildo into him.

When she pulled away from the kiss, she again took his cock in her hand, and with the other found his prostate once again with the tip of her dildo. She exhaled a small laugh knowing how little control he had over himself or the situation, as she went for the coup de gras, Doug's eyes almost rolled back in his head as his cock flexed and his asshole gripped her little purple dildo as he came harder than ever before. Melissa aimed his cock at Doug's own face, to further his degradation, but this was fruitless as his sperm shot clear over him and landed on the floor beyond the far side of the desk with a bit of a splashing sound.

Doug was panting, out of his own head when Melissa reached for her purse strategically left on the desk. She pulled out another toy, which broke down into three parts as well as a moist cloth like a baby wipe. With the dildo still firmly in place, in his refractory period Doug's asshole involuntarily clenched, the grip on the dildo he found oddly pleasurable. He was still out of it as Melissa took care to thoroughly clean his dick before beginning to assemble something around it.

"This," Melissa explained, "is a chastity belt. It will keep you in my control. If you ever want to have another orgasm like that I suggest you not tamper with it." While she was talking all the pieces fit together, and when it was assembled she applied a small padlock. "Now," she went on as she slipped the key onto her charm bracelet, "lay back, it's my turn to get off, and I will tell you how it's going to be from now on."

Doug, finally regaining some composer, looked down at newly caged cock, he mind was a blur as she spoke, but he made out that there would be more orgasms like he had just had. He lay back on the desk as Melissa stepped away letting the dildo fall out of his ass. She stepped out of the harness, letting the dildo fall to the floor, hooking her thumbs in her panties stepping out of those as well. Coming to the side of the desk, she reached into her purse at the side of Doug's head. She pulled out a blind fold, which she immediately slipped over Doug's eyes. She climbed the desk and placed herself over Doug's face, "You haven't earned seeing anything just yet," she laughed at him before lowering her pussy onto his awaiting mouth.

Before she even could give the order, Doug began to eat her pussy hungrily. She took a moment to close her eyes and enjoy the sensation before beginning to lay out her future at Doug's company. "As I said, I will be moving up in this company, there will be a lot of training and rewards, for both of us. I will train you to be my chastity butt slut, and you will reward me with steady promotions and pay raises, in turn I will reward you with release from your little belt, your little chastity belt, and reward you with an orgasm with each promotion." She adjust her breasts again just how she had in their first meeting, and chuckled, "Who knows maybe one day you'll even get to see my tits."

Doug shoved his tongue deep into her as she spoke; her degradation of him turned him on immensely. Even having just had an orgasm, his dick was getting stiff again, but was quickly rebuffed by the hard, unforgiving plastic of the chastity belt. Melissa further laid out her plans for their personal and professional relationship as he had her eat her asshole as well, letting herself orgasm on his face.

Doug was eager to promote Melissa in his company; he yearned for release from his chastity belt and another orgasm like she had given him. But he couldn't be too hasty to let the other employees get suspicious.

It had been two months since their first encounter. Melissa had come in to work only six times in the eight weeks. Each time she and Doug had what she liked to call a 'strategy meeting' where she would take him in the ass with a strap on dildo behind the locked doors of his office. She stayed fully dressed, wearing a strap on over her jeans as Doug completely disrobed to become her play thing, wearing only his chastity device. Usually he would have him bend over his desk as she pumped into him, his caged cock bouncing back and forth with each thrust, before turning him around and taking him in the missionary position toying with the chastity belt as he was forced to look into her eyes as she fucked his ass with her toy cock.

On the last of the six visits she brought a larger dildo than before. "I know you can handle it sweetie," she cooed at him as pressed the tip past his sphincter. Doug groaned as it entered him, it was both longer and wider, but Melissa got the entire thing in before she found her usual rhythm she liked to fuck her boss with. She laughed at his new facial expressions, and noted at his cock helplessly growing in the chastity device. "See, you can't pretend you don't like it," she gave a deep thrust into him, finishing, "don't worry, I have more that are even bigger."

Doug just exhaled deeply as his body adjusted to the new girth and he began to feel pleasure from the rubber running past his prostate, "Yes Miss Melissa, I think you're due for a promotion."

Melissa smiled wide, "Am I?" she said with delight excitedly increasing the speed and depth of her thrusts of her large dildo into Doug's ass. "That's great," she jingled her charm bracelet holding his key, "and when I get it, you'll get your half of the deal too." When she had her fill of fucking his ass, she had him suck the dildo clean before donning him with a blindfold to eat her pussy.

There was a small office party for Melissa's promotion later that week. She was given some bullshit title, and there were many snickers that she only got it because she was probably fucking the boss, if people only knew the truth.

Later, after everyone else had gone home Doug was waiting in his office when Melissa stood in the door way. "I have a surprise for you," she said as another woman followed her into the room. "This is Daisy, she got me started at the club, and with my promotion, I think now I am the one who needs an assistant." Daisy, like Melissa was beautiful, and in her early twenties. "Don't worry though boss," Melissa started stifling a laugh, "I told her she had to fuck you to get the job, so why don't you get ready.

Doug face wore a shocked expression; he didn't know what to make of this. But when Melissa and Daisy got to his desk and started making out, his cock, pressing against his chastity belt, made up his mind for him. He took his clothes off quickly and sat on the edge of the desk.

Daisy went to take her clothes off as well and Melissa stopped her, "Oh, that won't be necessary," she laughed. Melissa pulled out the harness and larger dildo from the previous time and laid out the real deal to her friend.

When Daisy heard what Melissa had set up for herself she was in a state of utter disbelief. Stepping into the harness, Daisy said, "Jeez, Mel when you said I had to fuck the boss I had no idea you meant like this," she thought a moment eyeballing the chastity device around Doug's dick, "and he can't even get hard?!"

Melissa laughed leading her friend between Doug's legs, "No, not usually, he just loves it up the ass that much, I've been training him to take bigger dicks, and it feels so good for him he doesn't mind that he can't get hard, though his cock looks pretty cute trying to in that chastity belt," Melissa took Doug's chastity belt between her fingers giving it a shake, "besides, that's how I keep him so well behaved. Isn't that right Doug?"

"Yes Miss Melissa," Doug's head sunk as he submissively agreed with both facts of her statement.

"Good boy Doug," Melissa taunted, "tell Daisy how much you love it that I have total control over you."

Doug went on, complying with his mistress' request, "I love taking it in the ass from Miss Melissa while my cock is locked up in a chastity belt. She controls my dick and my ass, they are her playthings."

Daisy couldn't help laughing, "Mel, you have to teach me what you did to this guy. You're the master"

Melissa smiled back, "Sure thing Dais, lesson one is get that cock in his ass." And with that Melissa helped Daisy guide the dildo into Doug's ass. Melissa stood behind her friend, helping her find the right rhythm like she was helping her with a golf swing.

Once Doug was getting his ass reamed out like he was used to by this new girl, Melissa came to his side with key in hand, she explained to Daisy as she unlocked the small padlock, "we have a bit of a management training program going here, I train his ass to take bigger and bigger cocks and his dick to have fewer and fewer orgasms, and he promotes me in turn."

She took the tube portion of the belt off, Doug's cock sprang to life as she continues explaining to her friend, "and with each promotion he gets to have his little cock come out and play, it's been two months since things even been hard."

"Two months?!" Daisy asked in shock, "man he'd probably come just from taking it in the ass."

Melissa raised an eyebrow, "hmm, you know maybe, let's try it, what do you say Doug?"

Doug pleaded, "Miss Melissa please, like it was before, please make me come like that again."

Melissa laughed at him, "Ok, I will make you deal, if you can last ninety seconds, I will make you come however you want, and I will let you see my tits. Go on Dais, give him all you got."

Daisy aggressively worked his ass with her strap on, and stroked the length of his thigh with her finger. She pulled the dildo out almost to the tip before ramming it fully back in. In under half a minute Doug gritted his teeth as again he came so hard his sperm went airborne and his ass gripped the dildo tightly. Both women laughed hysterically.

Daisy remained at her position, leaving the dildo fully inserted as Doug lay back on the desk panting, "He hasn't seen your tits?" she inquired still laughing.

"Oh that's nothing," Melissa said. She quickly cleaned Doug's cock and reassembled the chastity belt before blindfolding him again once more. The remainder of the night he pleased both women orally as they each took another turn fucking his ass with the strap on.

In the next few months Melissa and Daisy took full advantage of their new positions. With two of them working there not a single week went by that Doug didn't get fucked up the ass at least two separate days. This also allowed them to increase the dildo size more frequently. Some days they would both come in, Doug would take in the ass from one while eating the other out and then they would trade positions and do it all over again.

Daisy earned her keep as Melissa's assistant coming up with new ideas for debasing Doug. Soon they had Doug wearing the strap on, he could fuck them both until they came without him feeling a thing himself, and then they would use their own juices on the dildo as lube, putting it right back up Doug's ass.

Daisy also researched milking, as a way of draining Doug's prostate without letting him orgasm. The first time they tried it, Melissa accidentally made Doug cum, and he was forced to promote her the very next day. But from there on out they were able to drain him without giving him an orgasm. This milking helped alleviate the pressure on his loins and allowed him to be kept in chastity for longer periods.

Some days, when they were there together, while working a rubber cock into Doug's ass, Daisy and Melissa would talk about some of the men they've been dating or just casually having sex with. Daisy didn't stop humping her toy into Doug when she grabbed his caged cock and balls in her hand, his dick struggling against the plastic from the stimulation, as she asked casually, "How about you Doug, you fucking any new ladies we should know about?" Doug had no answer, partly because he obviously hadn't and partly because as she finished her question Daisy thrusts deeply in him with a little extra power. It wouldn't have mattered, because both women were laughing too loudly for him to answer anyway.

Within two years, both women had been promoted so much that they were able to abandon stripping entirely. Amazingly, when he wasn't taking it up the ass, Doug was still running his company well enough to burden two do nothing employees. This was also due in part to his non-existent social life, there wasn't much sense in him dating when his cock was under lock and key, and he couldn't even get hard without Melissa's permission. With their new found free time, Melissa and Daisy worked out a schedule system. Daisy came in Mondays and Wednesdays, Melissa came in Tuesdays and Thursdays, and they both came in on Friday. Not a day went by Doug wasn't having his ass toyed and stretched, and the girls were made to cum by Doug's mouth or forcing him to wear a strap on over his own caged cock.