A Tale of Two Sidneys - Cover

A Tale of Two Sidneys

Copyright© 2009 by Ted55

Chapter 2: Crossing the Lines

Erotica Sex Story: Chapter 2: Crossing the Lines - This is the story of two men; one at the beginning of his sexual life and one closer to the end. Each crosses generational boundaries to fulfill their needs. Not without consequences.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Consensual   Reluctant   Coercion   Drunk/Drugged   Lesbian   BiSexual   Heterosexual   Slut Wife   Group Sex   Oral Sex   Voyeurism   Big Breasts  

Melissa hadn't made the dress for the interview and it was quite inappropriate. The stretchy and difficult to sew high tech material was too tight, too short, and too off the shoulder to be considered acceptable business attire. When she looked at herself in the full length mirror she got a rush. She looked irresistible—even to herself.

The small handbag she picked up from the hall table near the door to her apartment was another of her own creations. The aqua swirled together with pink and orange pattern complimented the sexy dress. Slipping into her beige three inch heels she fluffed her armpit length shiny auburn hair one last time before exiting into the public hallway. Her apartment door closed with a reassuring clunk.

She couldn't resist a quick glance at how the short skirt rode up as she started the past its prime Honda. She needed to replace it but that was impossible with her current income. When the car was in drive Melissa wiggled her hips just enough for the baby blue of her panty crotch to come into view. It didn't take much.

During the short drive to her interview the recent college grad wondered just how far she'd need to go before Mister Dickens would get the hint.

'Maybe he's a different man in the office, ' Melissa worried. 'Maybe he saves his philandering for the bar.'

Stepping out into the industrial area parking lot she tugged her skirt down as far as it would go. It still just barely reached her mid thigh.

"Show time," she said under her breath and the butterflies in her lower belly took flight.

She'd been told to come in through the plant entrance since the office door would be locked. Walking down the short hallway lined with bulletin boards she passed the time clock which read six-thirty.

The end of the hall opened into the manufacturing area which was not huge. The shift supervisor noticed her almost immediately and approached. The coarse looking man stripped her naked with his eyes enroute. It wasn't new to her.

"You're here to see Sid ... uh, Mister Dickens," the foreman asked with his eyes on the prominent cones that shaped the top of the dress.

"Yes ... I'm Melissa Somers," she introduced herself and extended her hand in greeting.

'Best to make a good first impression, ' she resolved.

'If ... when I get this job I'll probably be working with this blatant lecher.'

The name tag on his shirt said Bill and she judged him to be in his late forties.

'Old enough to be my father, ' Melissa concluded as the big rough hand enveloped hers.

"Bill ... Bill Mitchell," he supplied his name and condescended to shift his gaze from her chest to her face.

"Follow me," he directed and headed for a doorway to her left.

The rap on the door post of his open door brought Sidney back from his reverie. He saw his nightshift foreman first and prepared to be informed of some production glitch. A second later the vision of loveliness whose photograph was still lying on his desk emerged from behind Bill's broad shoulders.

"I think you're expecting Miz Somers," the foreman introduced his companion.

"Yes ... uh, yes," Sid stammered but did not get up.

Melissa crossed the office with her hand extended, "Hi Melissa Somers."

The owner of the manufacturing plant accepted the small soft hand and felt an electric sensation flow from their joined hands to his turgid penis. The young woman's handshake was firmer than he'd expected. He realized that despite how lovely she looked in the photo that it really didn't do her justice.

"Please, have a seat," the shop owner invited his prospective employee.

Melissa smoothed her skirt behind her thighs and applied firm downward force to keep the hem from riding up as far as it might. If things worked out according to plan she'd flash him and maybe more, but right now she didn't want to come off looking like a slut. The dress, she knew, had her off to a somewhat shaky start in that regard.

Sidney was pleased with himself in maintaining a reasonable level of professional decorum during the interview. He managed to make eye contact a majority of the time and did not stare at Melissa's chest or her thick wavy hair as he was tempted to do. It was a good thing that the visitor's chair was too close to the desk to provide a view of the applicant's legs.

Sid rose from behind his desk signifying the end of the interview. Melissa got up as well.

"Thank you for coming in," Sid said extending his hand again. "I'll be making my decision by the end of next week."

The young woman did not tug her skirt down as she accepted her prospective boss's hand. The stretchy but tight material stayed where it had ridden up to which left the hem only inches from the crotch of her panties.

"Is there anything I could do to influence your decision in my favor?"

The question grabbed the knock-off clothing manufacturer by the nuts. Sid wondered if the incipient erection was noticeable on the front of his grey Pierre Cardan slacks. His eyes dropped from Melissa's face, down over the cone shaped hills past the pinched waist and settled at the flair of the twenty-one year old's hips.

He estimated that the hem of the girl's dress was no more than two inches below the crotch of her panties. He suddenly found himself wondering about the status of her pubic hair. He was experienced enough to know that it was a virtual certainty that she trimmed, the question was how much. He regretted the thought and the twitch. His eyes shot back up to the young woman's face. Sure enough her eyes were on the front of his pants and the half smile she was wearing was sufficient evidence for Mister Dickens.

Melissa met his gaze and the word that came to his mind was mischievous.

"Do you like the dress? I made it you know," she asked running her hands from just below her breasts to her hips; "my own design."

Normally moving her hands down her body like that would be to smooth out any wrinkles but she did the opposite. When her fingers reached the puckers that were created when she'd been sitting she curled her fingers pulling more material into the folds at her hips.

Sid's eyes followed the young woman's hands and was surprised at how fast the vision of her panty crotch impacted his balls—at the speed of light you might say. The hem line of the dress continued to rise until the whole bulging baby blue triangle covering her mons was visible. The factory owner wished, and not for the first time in his life, that he had telephoto vision. She was only six feet away but that was about five and a half feet further than he would have preferred.

While the manufacturing plant owner's eyes were riveted to her crotch trying to discern every detail of her pussy, Melissa got a warm rush from her exhibitionism. It was like his eyes were sending infra-red waves heating her vulva and the inseparable connection made the nipples go all crinkly and itchy.

The twitch he'd felt in his balls was the harbinger of his meat reaching its full potential. His slacks weren't tight but there wasn't enough room for even his modest manhood to scribe the arc necessary to achieve the vertical position that his libido was calling for. The restraint of his erection was uncomfortable. Melissa watched in satisfaction while the impact of her little show became painfully evident.

"Oh Mister Dickens, I don't think you're even looking at my dress," the girl sighed with an adorable pout.

The stretchy material of the dress was tight enough that the hem did not move downward at all when she drew her hands up over her ribs. It was partly for him and partly for her own comfort when she ran her hands up to her pert cones. The warm wave that descended to her pelvic region when she cupped her boobies and felt their stiff points pressing into her palms was like a reflection or a backwash of the one that had flowed in the other direction a moment ago. The pliable flesh nestled into her hands and over flowed as she gave them an affectionate and ball grabbing squeeze.

"I know that I can be a valuable member of your team," the applicant assured giving her lush auburn curls a shake. "I'm very good at problem solving ... uh, especially problems like the one you have right now."

Sid hadn't said a word since he stood up to end the interview. Shock was too strong a word to describe what he was feeling during the young woman's lurid little show—delight was probably better. He'd lusted after the girl for quite some time before she'd arrived but in his heart he felt the impure thoughts were fantasies. He had expected to feast his eyes and nothing more. The thought that if he hired her for valid business reasons that he could, over time, perhaps suggest that being extra nice to the boss would have material benefits wasn't a plan; just a daydream. Melissa's move was so bold that for the brief time that they'd been standing, hardly a minute, he'd been completely mesmerized—speechless.

When the coin dropped and his big head got back into gear the secondary rush hit. As always there was a sexual component to the feeling of power and authority.

"Well Miss Somers, this might be an unexpected opportunity for you to display your problem solving skills ... just how would you deal with this <<clears his throat>> situation."

"Well..." the temptress said pensively, "the first step in solving a problem is to get intimately familiar with it in ... um, in every detail."

"I concur that is an excellent strategy," he responded.

His balls tightened appreciably when the stunning job applicant rounded the desk and stood immediately in front of him. His disappointment that the short walk had resulted in the dress working its way down far enough to hide her thong was short lived. He basically forgot about the lost spectacle when she sank to her knees.

"Hmmm ... there seems to be some swelling," she observed looking up at him with her big green eyes.

"I'm going to need to take a closer look ... okay?" she cooed as she began to work his belt buckle—the question was rhetorical.

The clothing plant owner's boner twitched involuntarily as his waistband fastener was released followed by the zipper being tugged to the bottom of its travel. The young woman's dexterity suggested that she may have done this before. A second later his trousers were around his ankles.

If his Pierre Cardan slacks had been doing a poor job of disguising his excitement the white boxers were outright pitiful. Sid's manhood sprang up nearly slapping against his overhanging belly when Melissa pulled them quickly down to his knees.

Relief of the strain on the ligaments that had been straining to hoist his cock into the vertical position was offset by new pressure in his scrotum. In spite of the exposure to the coolness of the office air Sid felt his tackle getting hotter—much hotter.

He was looking down at the luxurious auburn curls and waves when the dainty little hand took hold of him. There was nothing tentative about it.

'Oh fuck!' Sid managed to keep the words from coming out of his mouth but the guttural sound that did escape caused the kneeing job applicant to look up nevertheless.

The fact that her hand felt sort of cool was more a testament to how hot his member was than any indication of her temperature. She seemed to be squeezing as if testing his rigidity. He felt a tremor in his knees and wobbled a little.

"Oh Mister Dickens you'd better sit down before you fall," Melissa suggested and used her free hand to guide his executive desk chair up against the back of his knees.

The black leather was cold on his bare ass but that was the only thing that was cold; he barely noticed.

"Ah yes I see..." she continued the charade, "there's too much blood or something in here ... but how to get it out?"

Her manicured hand had begun a slow and rather short stroking action as she spoke. The length of her up and down movement was even long enough to completely retract her boss's uncut foreskin.

Never confident of his endurance Sid knew if he wanted to complete the show that Melissa had begun earlier that he'd need to do it soon. Especially when she began to explore his sack with her other hand. It was a paradox that her gentle caress created the vise like pressure he felt internally.

"Show me your tits."

He hadn't meant it to sound so demanding but the fact that he had his teeth clenched, straining against Miss Somers' effective ministrations made it come out as a growl.

The command diverted Melissa's attention back up to her boss's face. The sweetness of her smile was worth the price of admission.

The dress was already off the shoulder and the kneeling girl had no trouble peeling the elastic material down her arms. The bodice clung and dragged over her sensitive cones causing her to bite her lip. Her nipples were so itch and tingly already that dragging the fabric over them sent shivers of pleasure out like the spokes of two entwined wheels.

Sid watched the resilient flesh squashed as the top of the dress passed over them and then they spring back to their normal front projecting youthfulness. He was admiring the pebbly little areolas with their breath mint sized nipples pointing straight at him when the soft hands that had abandoned his manhood to lower the dress came up to cup and squeeze her plump cones.

"Are they okay..." she asked in a syrupy little voice that Sid felt in his loins.

He was driven to take his throbbing member in his own hand while he watched Melissa playfully display her tits. He only managed a grunt in response to her question.

"Mustn't lose focus," she announced in a business like voice, returning her attention to his lap.

The clothing plant owner moved his hand aside as the job applicant resumed her task.

Her grip was firmer this time and her stroke was longer. Moving up and down with a slight twisting motion Sid settled in to enjoy the effective stimulation. For an instant there was slight disappointment that this was going to turn out to be just a hand-job, but hey he hadn't expected anything at all half an hour ago.

"Hmmm..." she said, "I'm not sure this is working."

Sid thought it was very cute that she was caring on the pretense that this was a conundrum.

"Maybe I need to cool it down," she added pensively.

Her stroke had been moving his foreskin up and down exposing most of the head. At the bottom of the next stroke she spit a large amount of saliva onto the purple crown of his rigid member. Loosening her grip, she slid her hand up and smeared the spit over the exposed glans. The seated man felt his balls jerk at the direct stimulation of his most sensitive part. When his hips twitched in response he saw Melissa's smile broaden.

Her manipulation became multi-facetted. Several quick, firm up and down strokes retracting and replacing the superfluous skin, then at the bottom of a stroke, with his corona exposed the nymph took a gentler grip and moved up over the helmet shaped tip. Her twisting little hand seemed to be attempting to polish the shiny slippery knob.

The combination was repeated over and over. Sid had not reached the stage where he needed to concentrate on holding back yet so he was free to enjoy the delightful attention his dick was receiving while he watched how her firm little titties jiggled with the movement of her arm. As the sputum was used up she replenished it by spitting on his dickhead again.

When she leaned forward a couple of minutes later he was expecting her to apply more saliva and he wasn't wrong—just the method was unexpected. Melissa brought her spit laden tongue up over his frenulum and keeping it very rigid probed his urethra with it. Sidney was familiar with the technique but it took him by surprise. It was not unusual that he felt it deep in his balls and probably wouldn't have bothered to stifle the groan even if he could have.

"I just learned that ... it seems as though you like it," the kneeling girl giggled.

"Oh yeah!" he returned her smile enthusiastically.

She did it again with the same appreciative vocalization.

Sid felt things getting hotter and tighter. He had to pull back on the reigns but it almost wasn't enough. She took about half of his boner in her mouth and, after rubbing the head against the velvety softness of her inner cheek, wrapped her lips around the shaft and started sucking—hard!

"Oh fuck!" the clothing manufacturer wailed and this time the expletive did come out of his mouth.

The sinews stood out on his forearms as he gripped the arms of his executive chair trying desperately not to prematurely fill the auburn haired cocksucker's mouth.

Up and down the mouth and the hand working in perfect unison; Sidney found himself fighting a loosing battle. He knew that he shouldn't, but he entwined his fingers in Melissa's silky auburn locks deep enough to feel the hardness of her skull. When his feet went numb he knew he'd lost the war.

The hot tingling began at his knees and rose up his thighs at amazing speed. The thought of warning her and allowing time for her to avoid taking the ejaculation down her throat occurred much too late. His balls and prostate spasmed simultaneously and the first forceful jet hit the back of Melissa's throat. The spine tingling release from his reproductive system shot to his head making it spin. Some deep conditioned reflex was listening for the choking gagging reaction and when he didn't hear it he took the plunge into the pool of warm post orgasmic tranquility.

His breathing began to return to normal though his head wasn't clear. The first thing he was sure of was hearing water running in the little bathroom attached to his office.

A woman's voice from somewhere out of his vision ruptured his balloon;

"When do I start?"


Julia Dickens pulled her XK8 into a parking spot near the clubhouse. She was thinking how fortunate it was that she didn't have to drive far; didn't even have to leave their gated community to reach her dinner destination. She was aware that the second martini wasn't a good idea but she'd made the little pitcher and it didn't seem to want to go in the fridge. How could she sit in the bar waiting for Sidney and not have another? Well she could, but she wasn't going to.

There was fleeting eye contact with Ivan the Wonderful behind the bar as she entered the lounge adjacent to the restaurant. Julia scanned the dozen other members enjoying cocktails and beers before she spied Gwen Dumas sitting in one of the booths. The newest member of the club was all alone; but not for long.

As she crossed the room she felt the men's eyes on her but paid no attention. The pale purple cocktail dress didn't flaunt her charms but it displayed them very attractively. The swish of her skirt and the rolling twisting motion of her backside was her natural gait in the three and a half inch heels. If it drew the attention of almost everyone in the room, that wasn't her fault.

"Hi Gwen ... mind if I join you?"

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