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The Naughty Secretary

Trisha had enjoyed some affair dating in the past but she had never contemplated what it would be like to fuck someone who was also her boss. Richard was attractive in an older man sort of way but it wasn't until they had shared some drinks at the Christmas party that she had started to have sexual fantasies at work, sneaking peeks at him through the glass walls of his office, even reaching down occasionally to touch herself gently. He had almost caught her in the act once already, looking up at just the wrong time. She pretended to be getting on with work as best she could but she was certain he had seen her hungry gaze and her furious blushing.

the secretary with her red shoes on her boss

She had tried to stop thinking about him to begin with but the more the fantasies came unbidden, the more she start to think, well, why not? Would it be so bad? Richard was a married man but that could mean experience and a lot of pent up passion. She couldn't help but wonder what the sex would be like. Would he be shy, or would he be dominant? What kinds of things would he ask her to do and would she say yes? I probably would, she thought, smiling to herself and sliding her hand down between her legs one more time.

....And Then One Night

Trish surprised herself by starting to do kinky things at work. She would wear sexy underwear to work though she still had no intention of making a move on Richard. She just liked the thought of this sexy secret she had that only she knew. She even started to masturbate in the bathroom cubicle to the thought of him bending her over her desk, the sound of his belt rattling as he opened his trousers making her wet even as she listened. I'm going to draw blood next time, she told herself, thinking of how she had to bite down on her finger to keep from screaming when she came in the bathroom to the thought of Richard inside her as she straddled him on the leather couch in his office.And yet, for all of it, a part deep inside her knew or at least believed that she would never go through with these fantasies. The risk to her job would be just too great and what if he decided to break their affair dating off later and fired her just to make things simple again. These thoughts ran through her mind constantly until the night she picked up her bag from her desk, turned to go home and saw Richard standing in the doorway of his office and staring right at her.

The Risk Only Makes Affair Dating Sweeter

'Working late?' he asked her. Trisha looked around and realized that they were the last ones in the office together. Where had the time gone? 'No later than you' she replied, thinking to herself that, under the circumstances, that was a pretty good comeback. Richard approached her slowly, continuing to hold her in place with his stare alone. All too quickly, it seemed, he was in front of her, his broad chest breathing in time with hers. She could feel her breasts heaving up and down beneath her shirt, and she berated herself for leaving her top button open. 'Wha..' she began, even as he reached down and took her slender wrist lightly between two fingers. Such a gentle touch and yet it sent an electrical bolt through her whole body. She could feel herself becoming wet, felt a single drop trickle its way down the inside of her leg. Before she knew what she was really doing, she had reached into his trousers and taken hold of his cock with her hand. They both gasped a breath somewhere between mutual surprise and explosive lust. He reached forward and tore her shirt open, revealing the black bra underneath, while at the same time she fumbled with his belt. The rattling sound it made reminded her of her fantasy so much that she immediately turned and bent over her own desk.

The Joys of Working Late

Richard finished undoing his belt the rest of the way and then ran his palms up the side of her legs, raising her skirt as he did so. She gave a little squeal of delight when his fingers glanced against her lips as he pulled her wet knickers down. Then she gasped as he entered her. Running his hands through her hair, he thrust again and again. His heavy breathing behind her exhilarated her, driving her to push her hips backward onto him so that each thrust drove a little deeper. She began to moan, her sounds joining with the rattle of the desk as each thrust inched it a little closer to the wall. She was close, and she could tell by his groans that so was he. 'I want you to come inside me, big boss' she breathed. It was a little cheesy and she didn't know where it came from, but what the hell, this affair dating had to continue! She was throwing caution to the wind here and loving every second. Then the seconds vanished as she came hard, feeling him come deep inside her and shudder with the release. 'Yes, yes, Yeeeeeeeesssss!' she screamed, arching her back upwards, her palms pressing into the surface of her desk. Then she collapsed forward and lay there panting, shuddering occasionally in response to little aftershock twitches from where he was still inside her.She looked back dreamily over her shoulder at him. 'How was that for you boss' she said, smiling. 'Excellent work, Trisha' he replied, out of breath, 'Unfortunately, I'm going to need you work late again tomorrow night'.

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