It isn't Really Cheating Ch. 01

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Frustrated boss gets a helping hand from a colleague.
3.9k words
4.61
15k
17

Part 1 of the 5 part series

Updated 10/14/2023
Created 08/25/2023
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PLEASE NOTE

1 References to Dan's wife's disability are intended solely as an explanation for his reluctance to stray, and is NOT implying that disabled people are incapable of having a good sex life. Please don't shoot me down over this issue.

2 It's been a long time since I wrote any stories and it's taking some time to get back into it. Please also bear this in mind if submitting comments. I've titled this as "Ch 1" in the hope that others will follow before too long.

3 Spellchecked for UK usage.

__________

"It's not really cheating..."

Her soft voice had been reassuring as she unzipped his trousers and slid her long fingers inside, and although they both knew that it wasn't really true, he had latched onto them to excuse himself. With each occasion and with each new step, he silently repeated the mantra.

"It's not really cheating..."

When alone and troubled by shame and guilt, Dan called to mind Rose' gentle, reassuring voice, and repeated the words over and over. With each repetition he almost came to believe it...

For a long time after his wife Linda's accident, he had no libido at all. The shock of it all, the massive change in his role, and the amount of time and numerous ways which he now spent caring for her hit him hard. Linda was now confined to a wheelchair and although she still had all her mental faculties, she was physically very limited in every other way. Not that he resented caring for her. She was his wife of twenty-six years. Although she had bad days, Linda worked hard to be as positive as she could. Everyone was impressed by her attitude and determination and told them both so.

Dan wished that he could be more positive himself. He had paid for a series of counselling sessions, and gradually he managed to be more stoical and not to dwell primarily on his challenges. It was no easy fix, and he had better days and bad days. They still enjoyed quality time together and laughed (and cried) together, and he would still class their relationship as good.

But as his own state of mind improved, his libido started to return. Although Linda still enjoyed being intimate, sexual activity was very limited. He wasn't resentful against her, but there was no denying the frustration that he felt. He shrugged his shoulders and assured her it didn't matter, of course. Their sex life had previously been good but rather conservative, and after sixteen years sex wasn't easy to discuss or to experiment with.

He had never been immune from looking at women, of course, but he now watched certain female television presenters and actors with new interest and intensity. A lady in her thirties a few doors away often drew his gaze, too. He had resumed masturbating on a regular -- now daily -- basis. Three or four junior colleagues in the accountancy firm of which he was a partner also drew his eye.

He was very cautious concerning them, however. He had no intention either of making a fool of himself or of getting drawn into an affair. He had always maintained a high level of professional behaviour and had always avoided anything more than a fleeting glance at female colleagues. He still strove to act in a professional way, but he did find his glances becoming brief rather than fleeting, and sometimes becoming discreet gazes rather than quick glances. Nor did he ever fantasise about them or masturbate with them in mind. He really didn't want to go down that road, not only because it might it lead to acting indiscreetly, but because he genuinely felt it disrespectful to them and a betrayal of their trust.

Rose was part of his team. She was hard-working, thorough, and very personable. She was always cheerful, too, and well liked both by colleagues and clients. She was in her early thirties and slender, (he found out later, a dress-size 10). Her build was similar to that of Linda when in her thirties. Rose's breasts were small but high-mounted and pert, and in perfect proportion to her slender body. She wore dresses rather than skirts, and although she was too professional to dress provocatively, her dresses were always quite short, reaching just to her mid thighs. They weren't figure-hugging, but they fitted closely enough to be discreet and prevent views inside its hem when she was going up or down stairs.

When seated, her short dress hem rode still higher, revealing more lean, well-toned thigh and soft looking skin. Dan genuinely tried hard not to look, especially when they were alone in his room and looking through a client's account or having their monthly one-to-one meetings, but he found it almost impossible not to glance at least. Rose never seemed to notice his fleeting looks. Or, if she did, she seemed not to mind. Either way, she never mentioned it or made any attempt to adjust her dress for the sake of modesty.

To be truthful, Dan had begun to find the mere fact of being alone with her intimate, then arousing. Rose's mother had died suddenly a year or so earlier, and he had done all he could to support her through it. It had hit her hard, and Dan's soft spot for her had grown. Perhaps the intimacy of having her cry on his shoulder (metaphorically) had laid the foundation for what followed. Since then, her soft voice and slim figure, pale eyes, her minimal make up and tied-back blonde hair began to intrude increasingly upon his thoughts. So did her sunny disposition, and he began to enjoy their one-to-one time together more than he really should.

Despite his misgivings, sometimes in private he found himself imagining her in her underwear, trying to picture the tops of her little orbs above a lacy bra, imagining the tops of her bare, lean thighs, and her crotch under matching tiny panties. He felt ashamed when such thoughts first arose, and tried to drive them away. It seemed a betrayal of her trust and of her genuinely nice personality. But the thoughts kept returning. He flushed with embarrassment when he caught himself wondering fleetingly whether she shaved or trimmed her pussy hair or whether she left it natural. From the fact that she kept fit at the gym, he guessed that she probably at least trimmed it.

The fateful day began like any other. He had a one-to-one meeting booked with Rose at ten-thirty. All the partners held these with each staff member of their team. They served as catching up sessions to ensure that any work or workplace difficulties were aired and addressed. She knocked on his office door, slid the sign on the outside to "Do not disturb", and greeted him with her usual sunny smile. She was wearing a grey pinafore dress and white polo-neck top underneath. He swept his eyes over her high-mounted pert breasts, her slim arms and her flat stomach.

The weather was mild, and Rose' legs were bare (she always wore black tights in cooler weather). As she sat down, he watched her dress glide up her thighs. He felt flushed, the intimacy of being alone with her arousing him again, and, to his horror, he felt his member begin to stiffen as his curiosity about her underwear came to mind. The harder he tried not to glance at her lap, the more difficult it became to avoid doing so. And the harder he tried not to think of her sexually, the more aroused he seemed to become. They began to talk through what she was working on that week.

"Are you okay, Dan?" she asked softly after a few minutes.

He looked into her piercing but kindly, pale eyes and at her soft looking lips that bore just a tinge of pink lip gloss. Her question took him aback. He sensed that she had rumbled his straying gaze.

"Er, yes, Rose, yes, thanks. I just find it a bit warm in here, that's all."

"You could touch as well as look, if you like?"

A bolt of shock hit him, and a wave of shame swept over him. As if it wasn't bad enough to be caught looking at one of his staff, he was being confronted, and by the very person in question.

"Sorry, Rose?"

He hated himself for resorting to the old trick of playing the innocent, pretending not to understand, but he had to play for time. To make matters worse, he felt his face flush with embarrassment, confirming his guilt.

"My legs. You can touch them if you like, Dan."

"Really, Rose... I..."

Further pretence was futile. Better to come clean and apologise.

"I didn't mean to. I'm sorry. I'm really sorry, Rose."

She leaned across and gazed into his troubled face. She took his hand in hers and placed it on her right thigh.

"I meant what I said, Dan. You can touch my legs -- my thighs -- if you like, instead of just looking at them. If you want to... and I think you DO want to..."

He felt suddenly hot, and flushed deeper. His semi-hard member gave a twinge of excitement. Her skin was deliciously soft under his fingertips, and invitingly warm. However, he forced himself to withdraw his hand.

His mind was in turmoil. Was she playing with him, punishing him for his indiscretion? Or was she trying to provoke him into action and would then make a complaint against him? Would it all blow up in his face and ruin his position in the firm? The possibility that she might have no ulterior motive was incomprehensible. After all, he was sixteen years her senior.

"Er, I don't think that's a good idea, Rose. We, er, need to talk about the Jackman accounts. B... but it just isn't a good idea anyway. And... it wouldn't be right. I'm sorry for any misunderstanding..."

He hated himself for his incoherent babbling.

As if in slow motion he saw her hand reach out for his, and he noticed that his hand was trembling slightly. He looked into her face. Her pale eyes were kind but eager, and she smiled reassuringly. She raised his hand to her lips and kissed his fingers softly, then, slowly and still smiling, she led his hand down to her lap again.

"My legs don't bite, Dan!" she murmured. "Why not stroke them and caress them? There's no harm in THAT, Dan..."

She guided his hand up and down her lean, firm thighs, then over one outer thigh... then to her other, inner thigh. She led his fingers suggestively along the hem of her grey dress.

"Please, Rose... I'm married... we... I...mustn't... I can't..."

Again he withdrew his trembling hand, but again she took it in hers again. She pressed his fingertips against her warm, firm flesh and rubbed them round in gentle, circular movements. He stared down helplessly at the movement of his hand under hers.

"Oh Dan, I know you want to. There's no harm in just touching. I... I've seen the bulge in your trousers. I know you want to..."

He began to move his hand unbidden, just a little, caressing the soft skin of the front of her thigh. To his shock and delight, she parted her thighs slightly wider. He let his fingers stray to her inner thigh, teasing in little circles and kneading her firm flesh. Then, summoning his remaining willpower, he removed his hand once more.

"Rose... we mustn't... I'm married... Linda..."

His hoarse, stuttering voice was racked by shame, tension, emotion -- and arousal.

"Shhh, Dan. Shhh. We needn't go all the way. It's not really cheating..."

He watched her hand glide over his thigh to the zip of his trousers and tug it open then slip inside.

"It's not really cheating, Dan..."

He gave a gasp as her hand cupped his balls through his boxers then sought his half-hard shaft. He looked down at the rude sight of her hand moving inside his trousers. His shock and shame were equally matched by excitement. He had never once cheated on Linda in their twenty six years of marriage. The illicitness and arousal of acting unfaithfully was fuelled by doing so in his office while others were in the building.

"Just doing THIS isn't really cheating..." Rose insisted.

Her fingers gently and deliciously squeezed and kneaded inside his trousers, and he did the same to her bare, firm thigh. Then, still stroking him, she stood up slowly and nudged his chair away from the desk. She stood in front of him. Still stroking him slowly and gently, she guided his trembling hand up her dress.

"I think you should caress my private bits, too, Dan..."

The coyness if her term thrilled him. Her panties were made of stain and were enticingly warm and silky to his touch. He ran the back of his hand across the front of them, exploring her mound, and briefly nestled the back of his finger into its little depression. His mouth was dry with excitement.

"Oooh, Dan, that feels nice," she cooed. "I think you should pull my panties down and get a proper look -- and a proper FEEL, Dan..."

With her left hand she lifted her dress to her waist and held it here. He stared, transfixed. Her hips and waist were narrow. Her skin was pale, its paleness accented her black, scant satin panties. Through them he could make out the camel-toed shape of her mound and its discreet cleft.

Although he could no longer protest, he needed to follow her initiative and encouragements, anxious not to moving too far or too fast. Remain relatively passive and following her lead also mitigated his sense of guilt and shame. He followed her exhortation, leaning forward to hook his hands into the waistband of her panties. He stared at her crotch as he slowly bared it.

She was smooth-shaven and her pussy was small and trim, her labia a mere hint of fleshiness.

"Do you like what you see, Dan?" she murmured.

He nodded. His conscience berated him, but his desire was fuelled. Apart from looking occasionally at soft porn, this was the first naked crotch other than his wife's that he had seen in the flesh for twenty-six years. The thrill made him feel almost lightheaded.

"Yes, Rose. Oh yes!" he croaked.

"Touch it if you like, Dan. Touch that little pussy. It's okay. Touching each other does no harm to anyone..."

She parted her legs slightly wider. Her panties remained strung provocatively between her pale, lean thighs. The sight enthralled him. It seemed more wanton and provocative than if she no longer had them on at all. He stared, fascinated, at her discreet slit nestled between her little lips, and traced his trembling fingertips over them. He stroked them. He ran his fingers over her surrounding soft mound. He cupped the palm of his hand over it. He pressed his hand against her more firmly and rocked his hand in circles against her smooth-shaved, firm but slightly yielding flesh.

Rose gave a whimper of pleasure. He hoped it was genuine. He looked into her face, delighting in its serene expression. He stared down at the rude ballooning of his trousers as her right hand worked its magic inside them. He feasted his gaze once more on her hairless pussy and at his own fingers playing with it. He again rested the back of his finger between her trim, moist lips. He rocked his finger from side to side against the warm, dank flesh that wrapped around it. He slid his finger joint higher, seeking her clit. It was hard and lightly sticky. He felt her give a shudder of satisfaction and heard her sigh her appreciation.

"Why don't you stand up, Dan, and let me take your trousers down?"

He pulled away.

"I... I'm not sure, Rose..."

"I am, Dan. I think you should let me finish pleasuring you. I think you should let me bring you off. That isn't really cheating. I'd like to do that for you, Dan. And I know you'd like me to. In fact judging by how hard you are, I think you NEED me to..."

His resistance was all but gone now. There was no denying that he did indeed want her to wank him off, and there was certainly no denying that he needed her to do so. He fought back his shame and latched on to Rose's assuring and imploring tone. It wasn't right, but, given his current sex life, maybe it wasn't too wrong just to let Rose wank him off. Surely, he reasoned with himself, it wasn't much different than masturbating himself. Was it? He knew that there was a huge difference really, of course. But the illicitness of it all aroused him further.

He stood up, and with eager eyes he watched her lithe fingers unclip his belt, unzip his trousers and tug them down to his knees. She did the same with his boxers. Still standing, he leaned back against the desk. She stepped close to him. Her panties were still strung wantonly wanton between her slender knees as she parted her lean, pale thighs a little wider. She pulled up her dress hem again with her left hand and, reaching over, placed his left hand on the hiked-up hem of her dress.

Again he stared at the slender fingers of her right hand as they guided his right hand back to her pussy, then he switched his hungry gaze to the fingers of her other hand as she wrapped them around his hardness, shafting it slowly and sensually. She teased his slit, spreading his seeping pre-cum over his throbbing tip. The sight was lewd and very arousing. She let go of his hand and he watched his fingertip touch her clit tentatively then roll it around. He gave a soft moan, savouring its hardness and its stickiness. She gave a low sigh in response.

They looked coyly and briefly into each other's faces, then he shyly looked down again. Her hand was shafting him harder and a little faster. Under her dress her small breasts were shaking subtly in time with the movement of her hand. He pressed his fingertip against her hard, sticky clit, rubbing it harder and faster in synch with her jerking hand.

"Oh that's good, Dan. Like that, yes!" she hissed. "Make me come, Dan, and give me your hot sticky spunk. I want to feel it shoot all over my hand..."

Her coarseness was in stark contrast to her customary demureness and professionalism, and excited him greatly. She relaxed her grip a little and he began to shaft her cupped palm and fingers, lubricated by his pre-cum. He thrilled to hear her breathing becoming quicker, as he frigged her harder, and realised that his breathing was also becoming faster and shallower. To his delight, while she continued to pump him, she slid her other hand inside her pinafore dress, She cupped it over one of her small breasts and squeezed it quickly and rhythmically through her polo-neck top. He longed to see her breasts naked, but things were moving too quickly for that now.

"Give it all to Rose, Dan," she cooed. "Fuck my hand and give me your juicy load," she urged softly.

He always enjoyed being on the brink of orgasm and anticipating the sweet release almost as much as the release itself.

"That's it, Dan... shoot it, go on, go on... YESSS!"

Her coarseness enhanced his excitement. He was now at the point of no return and gritted his teeth, watching his pulsing tip thrusting lewdly in her slender hand.

"Oh yes, Rose, oh yes..." he croaked, as, gasping, he watched his gooey cum shoot onto her young, eager hand and ooze through her fingers.

Embarrassed, he saw some of his cum drip onto the office carpet. He slowed down his pace but did not stop his thrusts, enjoying the sensation and determined to prolong it even though he was spent. He switched his gaze to her crotch and to the frigging of his fingertip on her glistening nub. He looked into her eyes and noticed that they were closed. Her expression as blissful. She had parted her lovely slender thighs wider and was bracing herself more firmly against the floor.

"Give me your fingers, Dan... put three fingers into my pussy and finger-fuck me... oh yes, Dan, YESSS!"

Her enveloping flesh was tight and slippery as he obeyed her plea. He knew that her own orgasm was fast approaching, so he contented himself with plunging his fingers back and forth without any subtlety. She raised one leg and locked it around his, clasping him firmly to her. Her slick tightness gripped his thrusting fingers. He stared at the rude sight of her pussy being pleasured simultaneously by his own fingers and by hers. She was still squeezing her breast rhythmically inside her pinafore dress.

To his delight he noted her breathing turning to little gasps. Her serene expression gave way to a contorted one, and her body began to jerk and spasm with her climax.

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