His First Time Cheating On His Wife

If you haven't read the first part, I hope that you do. I had a wonderful time writing it, as it was my first attempt to write from the man's point-of-view. Based on the responses many of you sent, I was fairly successful. This picks up from where I had given, and taken, some great oral sex with my boss. He is much older than I am, about the same age as my father. I must admit, there was a little bit of weird incest-type of thing going on, as I have always had a "thing" for older men. So, let's begin. This story takes up where the last one left off; when Elaine promised her boss that he could have sex with her.

_______________________________

Richard had always wished that he had come-of-age in the glory days of the advertising agency business in New York of the 1950s and 1960s. This is the era portrayed in the TV program "Mad Men," and he had no reason to believe it was much different than that fictional account. Three martini lunches, smoking in your office and plenty of extramarital sex. But, now, today the business is much different. To begin with everybody under the age of 55 has an MBA, a killer drive and a loyal-less attitude toward where they worked.

So, the standard of today is truly defensive (especially for the older guys), which means that they ate at their desks, drank bitter Starbucks Coffee grabbed at Grand Central on their way from their Connecticut manses to the office. The agency where Richard worked was staffed, as most are, by many young men and women. At 63 he was one of the most senior account managers in the company, and, despite being very fit and reasonably trim for his age, he often felt old. Richard was also was envious of the younger men whom he assume were getting "it" from some of the younger girls.

There is one young woman in his office; a copywriter on one of the accounts he manages. Her name is Elaine. She reminded him of a young Diane Lane, and he is powerfully attracted to her. But, he was loyal to my wife. As much, he thought, because of lack of opportunity as anything. His wife is still attractive, but as with many couples married over 30 years, her ardor has cooled. So, while they still play tennis about once a week that is about all they do together that raises a sweat.

All this ended one afternoon when Elaine was showing Richard some work-in-progress on a new campaign. Somehow, Richard blurted out that he wanted to "fuck" Elaine. He was very flustered, even frightened that he had actually spoken out loud his thoughts. She thought it was charming, and then proceeded to pleasure him with a magnificent, there is no other really good word for it, blowjob.

After a few days of cautious flirting, he caught Elaine alone in one of the conference rooms. He was as nervous as a schoolboy. Nevertheless, he asked her if she had meant what she said about them getting a hotel room together; that there would be a "next time."

"Of course," she said, running a finger beneath the glistening thin gold chain she wore around her neck, drawing attention to her beautiful cleavage. "I always mean what I say," she continued looking at him, head slightly bowed in a submissive pose. But, a small smile playing on her luscious lips. He stared at the light dusting of freckles scattered over her chest.

"Of course.., of course," He mumbled in reply.

"Besides, now that I've had a taste of you, I have to have more, don't you think," she said, her hand sliding gently along the inside of one silk covered thigh to just under the hem of her skirt. She ran her pink tongue around her lips, now smiling a broad smile that crinkled the skin at the corners of her eyes. "Just give me some warning, so I can create a cover story to tell my husband."

And this brought Richard to the lobby of a small hotel; a pension it would be called in Europe. This pension had only a few rooms, but each was elegant and very well appointed, not to mention expensive. Arranging a meeting-time for the two of them for this particular Saturday was actually pretty easy. It was not at all unusual for agency staffers to work on Saturdays. It has been said, correctly, that at any given moment there are staffers beavering away at agencies around the world.

He was sitting in a leather armchair in the small ground floor lobby. A bored clerk of indeterminate age and ancestry dozed behind the desk. Richard's palms were moist and his stomach fluttered. He rubbed has hands on the arms of the chair, and then chaffed them between his knees, trying to pull the anxiety out.

He glanced up, suddenly worried that she had had second thoughts, and he saw Elaine through the glass door, standing on the sidewalk her body sidewise to his view. She was holding a bright white file card and looking from it to the number above the hotel door. He could see her black bra incasing her breasts outlined slightly through her blouse. She had a large, shapeless bag over one shoulder. Elaine turned and stepped to the door, opening it.

There she stood, holding the door open with her left hand, her right one shading her eyes as she tried to adjust her vision from the bright Saturday sunlight to the dim interior of the pension. The background noise of cars, cabs and voices typical of Manhattan leaked into the lobby around her. She was dressed just as he had hoped. She was wearing a slim gray skirt; white starched blouse opened enough to display the tops of her wonderful breasts. She was smiling at him, her green Irish eyes glinting in the light reflecting from the lobby mirrors. Her auburn hair was worn to just to her shoulders. Her neck was slender and encircled by the thin gold necklace she always wore. Her face a pleasing oval with well defined cheekbones, and she wore large gold hoop earrings.

She stepped into the lobby, her black heels clicking on the tile, accompanied by a slight, soft swishing as her black silk-clad legs rubbed slightly together as she walked straight into Richard's arms, her light perfume enveloping him and setting his heart racing and the blood flowing into his penis with a sudden force that surprised him.

"I was so afraid you weren't going to meet me," she said, rising on tiptoes and whispering in his ear. She then placed her lips to his and pushed gently against him. He tasted her as her lipstick lips slid erotically over his, just the tip of her tongue sliding along the mere inside of his mouth against his teeth.

Avoiding eye contact with the clerk, Richard ushered Elaine into the small elevator and pushed the button for the floor their room was on. Elaine clung to his arm, her breast pushed against it warming him. In what seemed an eye-blink they were in the room. It was small and dominated by a king sized bed, a large screen TV on the black enameled dresser. There was a small closet, a small under counter refrigerator, and a tiny, but elegant bathroom. Thick black curtains covered unseen windows.

Centered on the small round table by the window was a bottle of Merlot, two glasses, backed up by a vase containing a dozen red roses. The smell of the roses permeated the room, causing Elaine to exclaim, "How lovely. Richard, how thoughtful you are!" She hugged him, running her hands under his blazer, lifting it from his shoulders and down his back and arms.

Taking the jacket, she carefully hung it in the small closet, and turned to Richard, saying, "This is soooo exciting. I've been thinking about you for days and days."

Richard's mouth was dry and he was suddenly very nervous about this whole affair. He didn't know how, but suddenly he had the wine bottle opened, his back to Elaine. When he turned around he was stunned to see that Elaine had removed her blouse. There she stood in her gray skirt, flawless white skin and smooth, smooth breasts encased in a nearly transparent black demi bra. He could see the shadows of her silver dollar sized areolas through the lacy material. His penis suddenly swelled, filling his boxers, the tip tingling with anticipation. His fingers felt large and numb.

While he watched, Elaine slowly slid her skirt around to her front, and unzipped it her luminous green eyes locked on Richard's. She stepped from it and tossed it over the desk chair. She stood before him, turning slowly around in a small circle. Her panties were boy cut and matched her brassiere. He could see the valley between her buttocks, and the bottom curve of each of them where they peeked from the bottoms, and the darker triangle of her well-trimmed bush through the black material. Her legs were encased in thigh-high nylons with a dark paisley patterned elastic tops, and there was an incredibly erotic line down the back of each leg in a 1940s fashion style. Her feet were still in her shiny black high heels.

Elaine stopped her pirouette and said, "See anything you like?"

Richard's cock was so hard it almost hurt. He absently reached down to adjust his engorged member in his shorts. Elaine, smiling, stepped forward saying, "Here, let me help," as she reached for his belt. She slowly unbuckled his belt and slowly pulled the zipper of his slacks down with one hand, the other tracing the outline of his inflated penis. As she moved, her breasts swayed slightly, adding to the almost overwhelming view. As she pulled his zipper down, her breasts compressed between her upper arms. Richard could see the traces of blue veins under the white, white skin of her tits, just lightly dusted with freckles like those across her small nose. He placed a hand on each of her hips as she reached into his pants for his cock. He said, "What about the wine?" stupidly.

"Let it breath," she said.

He was almost overwhelmed when he felt her small hand touch his penis, and then grip it, the other hand cupping his heavy hanging balls. "Here," she said, "As she pulled his pants and drawers down his legs, using one hand to motion for him to step out. She tossed his trousers onto the bed, and knelt before him, his cock bobbing as she bent her head and pulled his loafers and socks from each foot. Richard began removing his shirt.

Elaine looked up at him, her face serious as she slid her hands up the outsides of his thighs, around the tops, and finishing with her fingers lightly spread on his stomach, thumbs just touching his scrotum where they descended from his body. Her touch was electric, and his blue-veined covered penis throbbed and bobbed as more blood pulsed into it. She gazed up at him, his cock just millimeters from her slightly parted lips. He dropped his shirt onto the bed near his pants. She exhaled a warm breath from between her lips onto the iron-hard, blue-tinted mushroom head of his cock. He involuntarily flexed his stomach muscles causing his turgid member to flex and bob again.

Elaine, looking up at him, smiled gently and then touched the tip of his penis with her pink tongue. She licked and probed his pee hole without moving her hands from his stomach, but her thumbnails caressed his scrotum, coming to rest on either side of his cock. He could see her red-painted nails through the nest of his grey public hairs. His cock was rigid, veins snaking down its length providing a bumpy appearance, to where it joined the flaring helmet-like mushroom head. His cockhead was larger in diameter than his penis, which was also thick. He knew his balls were hanging down between his legs, heavy with his spunk. He smiled, pleased with Elaine's soft licks, the view down between her beautiful breasts to her gently curving tummy and the two gaps between her panties where they stretched from her hips to her lower stomach was luscious.

"You have a lovely cock," Elaine whispered. "I've dreamt of it since I first pleasured you in your office," she continued.

She smiled, gripping his large cock with her small hand. It barely encircled it. Her other hand cupped his full ball sack and gently squeezed. "Your cock is so big. Bigger, certainly, than my husband's." He could see her engagement ring and gold wedding band, which somehow added to his excitement. He was glad she hadn't taken them off.

Richard smiled down at her; his hands reached down and cupped her face. "You are a lovely, girl, but I bet you say that to all the boys,"

"Maybe," she answered, "But with you I don't have to lie. You have a monster. Maybe the biggest I have ever tasted." Her eyes glittered up and him. "Should I taste him again?"

Richard sighed and said, "Yes. Yes, please taste me again, Elaine."

He watched her, his lips opened just a bit in anticipation as she leaned into him, letting his flaring cock slide over her lower lip, and onto her tongue. She closed her lips around his penis, holding it about three inches in her hot mouth. She sucked on him gently. Then he could feel her tongue sliding over and around his cockhead; her fingers squeezing his balls ever so gently; weighing them in her smooth palm, her nails softly scratching the area between his balls and anus. Richard immediately felt two things. His stomach lurched in pleasure as her mouth's damp heat radiated up his body, and his knees felt weak.

Elaine must have felt his knees buckle, because she used both her hands to push on Richard's hips so he would sit on the bed. As he sat, she kept his hard member in her mouth, and as he sat, she sucked more of him into her mouth, then deeper into her throat until her lips were buried in his public hair completely engulfing his rod to the root. The feelings were almost indescribable as Richard watched is cock disappear into Elaine's wet, wet mouth until her nose was touching his stomach. His cock, especially the head, felt as if it was gripped in strange and gentle vice.

Then, and then he felt his penis snaking out of her throat and over her tongue as she kept a tight suction. He wondered if she was going to siphon the sperm out his balls. She let this knob slip from her lips, the shaft shining with her slippery saliva. She looked up at him and exclaimed, "Wow! That was wild... I've never had a cock as big as yours so far down my throat. What a rush!" Elaine's eyes were shining, and spit dribbled from the corners of her mouth. She absently wiped her mouth with the palm of one hand, and then rested it on his thigh. Her other hand squeezed one of her breasts. Richard could see her mash her tit against her ribcage, furiously pinching her nipple. The cool wetness of her hand on his thigh made his stomach flutter, and he wondered what he had gotten himself into.

Elaine stood up, as Richard leaned back on his elbows, his bare feet hanging on the edge of the bed, touching the floor. Richard regarded his raging hard on, bobbing slightly with each beat of his heart. From this position his cock reminded him of one of those Japanese "pillow books," that depicted men with obscenely large penises. He was pretty certain that his was now as rampant as it had ever been, even as a young man.

Elaine reached behind her, also looking at Richard's cock, and unhooked her demi bra. She slowly allowed it to slip from her breasts, keeping her nipples covered with first one arm, then the other as she let it slip from her body. Richard sighed as he watched Elaine uncover. Slowly she moved, cupping her ample breasts in each hand as if offering them to Richard. She cupped each mound of flesh and then jiggled them, smiling hugely. "You like?" she asked.

"I like," Richard replied as Elaine moved between his spread legs, and bending over offered a nipple to Richard, who sucked it between his lips, marveling at how hard and long her nipples were. With one hand he grasps the other and squeezed it. Elaine squeezed the one as he suckled. She shut her eyes as wonderful sensations slid up her nerve endings, snaking beneath her skin and concentrating in her tummy. With her free hand she reached between her own legs and began to squeeze her mound in concert with her breasts. She felt her chest growing warmer, and her hot cunt growing wetter. She could feel her labia beginning to feel slippery as her juices began to flow, and she was surprised, as always, at the amount of heat generated by her sex.

Elaine could feel the hot shaft of Richard's penis as it touched one inner thigh. She thought she could detect some slime from his cock, precum, adding its heat to her leg. She wasn't aware, but she moaned low in her throat as she touched herself and as Richard nibbled on her nipple, his lips surrounding her entire aureole, raising reddish bumps. Richard switched breasts, and began to suck gently on the other, his hands now on Elaine's waist. He slipped his hands under the elastic of her panties, and pushed them down over the twin globes of her ass. His large hands squeezed her wonderfully soft cheeks. His fingers probed between her globes and, separating them slightly, his fingers searched for her hot center, fingers grazing her anus, causing her butt to clench slightly and a small thrill to flash through her womb.

One finger found her wetness, and slithered back and up from her tiny bud through her silky labia to touch, to just barely touch ever so lightly, her hardening clit. It was Elaine's turn for weakening legs. Richard pulled his mouth from her breasts, her nipple being engorged with blood and passion from his sucking. Using both wrists, he pulled her panties down her thighs to mid-calf when she, reaching out to hold his shoulders, kicked them off and to the side.

Richard immediately buried his nose in her mound, pushing against the top of her slit. Her soft stomach leaned against his forehead as he inhaled her scent. She smelled like baby powder, perfume and her intoxicating female musk. Pulling his face from her middle, and using his thumbs he spread her, and he gazed at her pink, wet slit. He rubbed her pronounced clit with one thumb. She hunched her hips forward to expose her cunt to his inspection, sighing.

"Here, he said, lay down," He said.

Elaine slowly crawled onto the bed until she was on all fours alongside Richard her breasts were hanging down and he could clearly see her nipples poking out, and he could see the her thin gold necklace glinting. He thought her breasts must be perfect; perfectly formed for her lovely, lovely, nubile body. They were lovely to his gaze.

He, too, crawled up along side her, and pushing against her shoulder gently said, "Lay down on your back. I want to eat you." Elaine shuddered; her skin rippling like that of a horse as she silently lay down beside Richard, her hand reaching out for him. She pulled him to her, their lips joined as his body pressed down on hers. His tongue pushed roughly between her lips as his kiss took on an urgency. Within moments both of their mouths were open to each other while their wet, hot tongues danced with each other, his hand slipping between her soft thighs. She spread her legs for him, as his hand slipped through her silky public hair. He pushed a finger into her, and began to push it in and out. In and out. She was soooo wet, and soooo hot to his touch. His thumb began to push against her clit in small circles as she sucked this saliva-covered tongue. She could feel the hot steel of his penis pushing against her thigh as he slowly hunched against her. He slipped one thigh between her legs. She ran her hands along his ribcage, sliding down until her hands rested on his ass cheeks. She felt the soft hairs on his buttocks as they flexed as he pushed his cock against one of her legs in the soft flesh above her stocking clad thigh. He loved the slippery feeling of her stocking against him.

He broke the kiss, his lips and tongue probed her neck and ear, tangling some in her hoop earring, his weight began to push down on her body, flattening her soft breasts against her body, her sharp nipples pushing into his chest like soldering irons. His muscled thigh pushed against his hand as he shoved two fingers into her smoldering snatch.

Richard then spread her legs, and moved until he knelt between them. He ran his hands up and down her soft inner thighs; so white between her black stocking tops and the soft red-brown curls of her pubic hairs. Elaine sighed, and shut her eyes, her hands resting on her breasts, squeezing gently. She sighed. Elaine look so sexy to Richard, her beautiful breasts spread across her chest, her nicely curved and soft stomach with its nice bellybutton center, Her auburn hair spread out across the bright white of the pillow. The sparse hair on her Mons was nicely trimmed and more red than brown and he could clearly see the top of her slit through them. Her slim legs, open to him, were encased in the shear black thigh-high stockings that came almost two thirds of the way up her thighs, the elastic tops darker black, decorated with a beautiful paisley pattern. The black high heels, still on her feet, made her look impossibly wanton. Her thighs, above the stockings were almost impossibly white, the skin flawlessly smooth. He could see fine blue veins running beneath her skin.