Connie's New Boss

It happened in a time when a boss could get away with it and they were often successful.

Connie is an excellent Executive Assistant. She has worked at the head office of a global food conglomerate in Toronto for seven years and rose steadily to her current position of Executive Administrative Assistant to the North American Sales Manager. She has a good rapport with her manager, Mr. Wilson and he trusts her implicitly.

Wilson is nearing retirement and rumors are rampant as to who his replacement will be but all the rumors turn out to be wrong and a guy from head office in England is brought in to fill the vacancy. Connie meets her new boss, Mr. Hilton and his wife as they do the grand tour of the building and to Connie he seems nice enough.

It was about two weeks since Hilton became Connie's boss when he first hit on her. To then, their relationship had been strictly professional. She politely turns him down saying she is a happily married woman, which is an exaggeration but this does nothing to deter him. For over three months he persists in his offers to take her lunch then on to a hotel where they would spend the afternoon. When they are alone in his office he makes constant sexual innuendos, tells her how sexy she is and how much he wants to have a sexual relationship with her. Things at home aren't great of late and her husband hardly touches her anymore. She enjoys the attention and sexual banter and she begins to wonder what an afternoon in a hotel room with her boss would be like .She has to admit she is attracted to Hilton. It is certainly a naughty and exciting thought to be fucked in a hotel room by her boss while the company is paying her but can she do it? She just doesn't know but with each offer Hilton makes she knows she is coming to the inevitable decision.

To this day she doesn't know why she says it. It had been a particularly bad weekend with her husband and when Hilton called her into his office at 9:15 she was angry and sexually frustrated. They go through the business for the day in about twenty minutes and she gets up to leave. "You really are lovely, Connie. Long blonde hair, slim with curves in all the right places and your bottom . . . perfection, let's have lunch tomorrow then, you know," he says.

It is nothing he hasn't said before but this time it sounds different to Connie somehow. She turns and looks him straight in the eye and says, "I'd love to, Mr. Hilton. Let's have lunch then . . . you know."

For several moments Hilton is stunned into silence, he just stares open-mouthed at Connie then, "Yes, well yes, very good, very very good. Lunch then . . . er . . . then hotel." He smiles broadly; she is another conquest and he is looking forward to fucking yet another assistant and another man's wife.

Connie smiles back, "Tomorrow then, lunch and hotel, I'm looking forward to it, Mr. Hilton."

"Umm, so am I Connie, so am I, yes indeed!"

She closes the office door as Hilton ogles her beautiful ass and imagines fondling, licking and, dare her think, fucking it. He rubs his incredibly stiff erection and mutters, "All in good time, Robert my boy, all in good time. Slow and steady wins the race, first her cunt then her ass, her entire body will be my playground and she'll keep coming back for more." Connie sits at her desk staring blankly ahead and realizes she is very moist between her thighs and allows herself to enjoy it.

At 1:40 the following afternoon Hilton is walking down the hallway of the hotel with the key to room 1641 held in a slightly trembling hand. Connie walks beside him and is equally nervous, she has never been unfaithful to her husband unless the three times they have swapped for sex with their friends David and Susan counts as being unfaithful but he seems not to want sex with her so if Hilton does she'll be happy to let him fuck her. Hilton opens the door and Connie walks in then turns around. The door clicks shut and he flips the security lock over. They kiss passionately, their hands urgently roving over one another's body. Connie's coat comes off and Hilton mauls her ass with both hands, "Ah, I've wanted to feel your ass for so long," he blurts.

She kneels as he takes his coat off and in a flurry of activity unbuckles his belt, unzips him and pulls his pants and underwear down. His cock springs up, fully erect and hugely engorged, "My, is he ever ready and big," Connie thinks. It's much longer and thicker than her husband's cock and David's for that matter whom she thought was big. She stares at it briefly, the blood-filled head pulsing with arousal, the thick, rigid shaft and his low-hung balls sack then wraps her lips around the throbbing knob hungrily as she fondles his balls and jerks him.

He moans and rubs his hands through her hair, "I've wanted to fuck you from the very first day we met," he pants.

"It's the same for me," Connie gasps as he lifts her up and takes her to the bed.

Hilton frantically removes her clothes and when she is naked he pushes her onto bed, "Now, spread your legs and play with your cunt, you fucking slut," he barks. Connie obeys but a little surprised by his tone. He strips off and she watches his big erection sway as he crosses the room to a leather bag he brought along and takes out some ropes. He stands and strokes his cock as he watches Connie fingering herself then extends his hand to her. She takes it, not sure of what is happening and he leads her over to the window. He ties her hands in front then loops the rope through the curtain rod and hoists her arms up and pulls her backwards until she is bent forward a little and her bottom is nicely presented. Although she is on the 16th floor she is in full view of the street below but Hilton doesn't seem to notice or care as he stands beside her as his big dick throbs against her thigh.

"It's been my experience that office sluts benefit from a spanking before they are fucked and don't worry, you'll like it, all the other sluts have and it reinforces who the boss is." She's confused as he proceeds to maul her ass and tits and finger-fuck her pussy but it feel so horny she goes along. The first spank comes as a shock and plenty more follow. Connie yelps and whimpers as her boss spanks her ass harder as his excitement rises and she begins to find it arousing.

"Tell me to stop, plead with me you slut, beg me to stop," Hilton yells.

Connie is sexually very aroused for reasons she doesn't understand yet and obeys his demands, "Oh please, ow, oohh, Sir please stop spanking my bottom, oh Mr. Hilton, Sir, please stop," she pleads. He ignores her and her protests only heighten his arousal and the spanks land on her, now pink, bottom. She realizes she is super wet and as aroused as Hilton and the heat on her bottom matches the heat in her pussy.

"Fucking office slut, tell me your a slut and want to get fucked."

Connie is enjoying this now, it's new, exciting and different, "Mr. Hilton, you knew I was the office slut from the very start, all the men in the office have fucked me and I want you to fuck now. Fuck me, Mr. Hilton, I want your big cock in my pussy, make me cum!"

"Oh you fucking horny slut," he cries and spreads her ass cheeks and thrusts into her willing pussy all the way to his nuts.

"Oohhh yes!" Connie screams, "Fuck your office slut, fuck me!. He grasps her hips and pumps savagely and relentlessly into her. Her bottom tingles but his cock in her pussy is like she's never experienced before, she moans, orgasms and cries out continuously, "Yes, yes, ooohh fucking yes! Fuck me, fuck me, fuck me!

After several minutes of hard fucking Connie from behind, Hilton pulls out and spanks her ass again. He unties the rope from the curtain rod and hurriedly takes her back to the bed. She staggers, still in a sexual daze from the spanking and pounding she has just experienced, not to mention feeling weak from multiple orgasms. She's not sure what will happen next but she knows whatever it is, she wants it. Hilton ties the rope to the headboard so that her arms are above her head then picks up other lengths of rope and secures them around her ankles and ties the ropes to either side of the headboard. Her legs are spread very wide and far back and her ass and cunt are lewdly displayed. She whimpers as he stands looking at her, stroking his cock which appears bigger and harder to her than before. She looks down at her pussy and it gapes wide open, it's soaking wet and her clitoris bulges like she's never seen it before.

"I knew you were the office slut the first time I saw you and married office sluts are the best kind. They appreciate and enjoy a good fuck when they get one and I think you know you are getting one and who the boss is in this arrangement."

"Oh yes Mr. Hilton, I love the way you fuck me. Do it now, do it again," Connie begs, almost in tears.

"I will you slut whore, all in good time. " He goes to the bag again and brings out a small riding crop which he lays on the bed. He kneels beside her and spreads his arm across the back of her calves and forces her legs even further back, this causes her butt cheeks to spread, exposing her asshole. "Ah, a nice, little puckered anus," he rubs a finger over it, "we'll do more with this erotic little hole in the weeks to come and you will learn to like it, won't you slut?!"

"Yes Mr. Hilton, Sir, anything, I will, I will, anything you want but please fuck me now!" she gasps.

"Yes you will and I am going to fuck you again but for now we'll just warm your asshole a little." He picks up the crop and commences a rapid spanking of her anus. At first it feels weird to Connie but after a half dozen smacks it feels weirdly sensual and she wriggles, squirms and whimpers with erotic delight, she has never had so many new sensations as she is having with Hilton. He notices that her pussy remains gaping and very wet and after he finishes cropping her anus he pushes four fingers into her cunt and listens to her cries of pleasure. He moves his arm from across her legs and moves the crop onto her pussy. Her clit is fully erect, exposed and very sensitive and receives a firm rubbing and pulling before it too receives a sound spanking that she finds intensely stimulating and climaxes again. She lies panting and gasping when he finishes but he gives her no respite. His cock is inside her again and thumping into her cunt hard. As he nears ejaculation his thrusts become ever more violent and both he and Connie are crying out in sexual ecstasy. She begins her umpteenth orgasm several seconds before Hilton unleashes a huge ejaculation of hot cum that spurts deep within and fills her.

He lies quite still on top of her for a few minutes as they catch their breath. She feels his cock soften and slip out of her pussy then he rolls off and unties her. She just lies there in the aftermath of a tremendous sexual encounter she never thought possible. Hilton knew what she needed and wanted and he delivered it in spades. He lies beside her and caresses her body, fondling her breasts and nipples, roving over her tummy and thighs. She jumps when his fingers find her clit, she is still highly aroused and very sensitive. He delves into her vagina and presents her with three cum-covered fingers and she tastes his semen for the first time. His deft fingers return to her pussy and work their magic and she shudders through another orgasm. He kisses her tenderly on the lips, their tongues dancing sensuously together. His gentleness after the spankings and rough fucking is an equally erotic contrast for Connie. Her hand drifts to his cock and he is already semi-hard. "Umm, you're already getting hard again, you naughty boy, do you want to fuck me again?" she whispers in his ear.

"I am going to fuck you again, I've always had quick recovery and when you're not getting it a home a new pussy or cock is extra exciting, don't you agree?"

"How did you know?"

"I've seen the look before, seen you staring at the bulge in my pants whenever you are near. I knew if I persisted you would eventually submit, I knew you were in need of some hard cock and thought it might as well be mine." Hilton is rock hard again now and he rolls back onto her, lifts her legs over his arms and slips easily inside her once more. His lovemaking is tender and sensuous. They fuck in different positions, enjoy a sixty-nine and he gives her a second filling of cum. They shower together and he drives to her car and they go their separate ways.

Hilton was out of town for the rest of the week and Connie misses him. On Monday morning, shortly after nine he calls her into his office. She sits in the chair and crosses her legs. Hilton smiles and Connie smiles back, he looks at her legs and says, "Open them, Connie, show me." She obeys and hoists her skirt so he can see her white panties. "You know what I want you to do," he says and Connie rubs her pussy then pulls her panties to one side and fingers herself. Hilton wheels his chair to the side of the desk and she sees his cock is out and very hard. "Come here," he says and jerks his cock and looks down at it. Connie goes to him, kneels down and sucks his cock and balls. After several minutes he stops her. "Sit on my desk," he says and when she is nicely spread he eats her to an orgasm. Before she leaves the office she adjusts her clothing and as she reaches the door Hilton asks, Lunch tomorrow?"

She looks up at him, "Yes please, Mr. Hilton, definitely lunch then . . . you know," she smiles and adds, "I'm also available on Thursday evenings if you wish, Sir."

"Connie, you are a wonderful office slut and by the way, that reminds me, in the hotel you called me Sir several times, I like that. From now on when we are in the hotel don't call me Mr. Hilton, call me Sir!"

"Yes Mr. Hilton, Sir!" she replies in a tone that indicated submissive deference then smiles sexily at him.

"Good girl, I still have much to teach you and we will both enjoy the lessons, I assure you. I'll make the reservations now for Tuesday afternoons and Thursdays for 5:00PM." As Connie begins to leave Hilton asks, "Leave slowly, I want to look at your backside. She sashays to the door, gives her hips a little wiggle then she's gone. Hilton's cock is stiff as he imagines fucking her again.