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.
