His Younger Secretarybysmallercuck©
This story has elements of humiliation (including small penis humiliation), older-younger sex, and cuckolding.
Lana was a middle-aged virgin when she married Steve, whose vast sexual experience consisted of a single brief and laughable encounter in a girlfriend's bedroom during college spring break. The experience had been so humbling and unpleasant that the slightly doughy and eminently fragile student stopped dating for several years afterwards.
By the time he met Lana, though, Steve had his degree in-hand and had started a career that was showing great potential. While most men ignored Lana, Steve felt at ease around her and he had never been happier than when courting the plainly-dressed girl who would become his bride. When Steve was with Lana, the pressure to pursue sexual intimacy was much less than with other, more aggressive, women. She was an old-fashioned girl who came from a religious family, and she preferred to wait before engaging in anything amorous. Steve and his lack of confidence liked it that way.
Since early puberty Lana had become an expert in camouflaging her curves. She had the round body of a certain earthy type of woman -wide hips and soft motherly breasts, but what natural sex-appeal she did have was bottled tight and buried under layers of wool sweaters, flower-print dresses, old-fashioned hair styles and quiet mannerisms. Lana's wide round bottom might have been flaunted to great effect by a more daring woman and her large round breasts necessitated high necklines lest she attract undesirable stares. But Lana was an expert in wholesomeness. Her face was plain and when she wore make-up it was of the most subtle variety. The conservative woman was likable and friends might even say she was an engaging conversationalist, but Lana had carefully avoided all types of flirtation. Even the slightest innuendo or overly familiar manner was off-putting to her. It was no wonder, then that Steve was the first man to show any interest in Lana whatsoever, but rather than be sexually attracted to her, he enjoyed her company in an entirely innocent and platonic way.
Outwardly Steve was a plain-spoken and successful businessman -a manager at large technical manufacturing company. Inside, though, he was the chubby junior-high boy who was teased by his classmates in the showers after gym class. When every girl in your grade knows you as "Pee Wee", you leave your hometown and concentrate on college. That's exactly what Steve Wallace did.
Sure, Boston was a huge change from growing up in rural Kansas, but at least here Steve had a fresh start. The small-town boy navigated big city life surprisingly well and Steve had even settled into a church with very Kansas-like values. Urban women could be horribly assertive and he had his share of terrible dates, but overall, he liked living where he was just a face in the crowd. Back in Kansas it seemed to Steve that everyone knew him as the guy with the small penis problem. He was a joke, with few romantic prospects. Small town rumor mills can be cruel. Getting out of there was the best thing he ever did.
By the time they were in their late twenties, Steve and Lana had been dating for several years. They had travelled together and had even slept in the same bed while vacationing, but Steve had never managed to summon the courage to hit on his companion. A small part of Lana was getting impatient, but her religious upbringing prepared the shy auburn-haired woman to wait until marriage for sex.
Lana had been sheltered. She was home-schooled by her parents who were prominent churchgoers. She had never dated before meeting Steve and even their relatively tame courtship caused a small scandal in the conservative denomination. Few of Lana's friends approved of her budding romance and rumors spread that the couple had spent several nights together prior to saying their nuptials.
Both bride and groom secretly hoped that an exciting sex life awaited them on the other side of the alter, but Lana was painfully shy and Steve, who could be quite assertive in his business dealings, was terribly insecure about sex. Once married, the couple just seemed unable to connect and when they did, Steve was so excited to be getting lucky that the festivities were over before Lana was even warmed up. Both Steve and Lana loved the other, but over time Steve's mind wandered more and more to delicious thoughts of the sexually liberated women who so intimidated him in real life. Meanwhile Lana's sexual side withered to nothing.
Ten years later, Steve and Lana were looking at forty in the rear-view-mirror. Steve was often horny but lacked the confidence to effectively court his wife, and Lana remained repressed and couldn't shake the sense that sex was sinful. It was no wonder, then, that when Steve met Allison Smith, he became so smitten with her that he set in motion the events that would lead to the demise of the couple's sheltered existence.
Steve had done well in his career and had become a respected manager at a successful business. When his longtime secretary retired, the well-liked manager spent months in search of the perfect replacement. He met with dozens of competent men and women, but could not quite settle on the perfect match. When the teen entered his office Steve's heart leapt in his chest. Allison was only 19 years old, had no secondary education, and was woefully under-qualified to be Steve's executive secretary. She did however have a perfect ass, beautiful smallish breasts, and a naughty smile that made the older man feel both aroused and weak in the knees. Her eyes seemed to say "You can have me", and Steve couldn't imagine wanting anyone more than he wanted the curvy little minx sitting across the desk. The successful man who was still the inadequate little boy, was simply defenseless against Allison's charms.
She wore a tight black skirt and stockings with a visible seam paired with a semi-transparent white blouse that showed off the swell of her tits and the lacy bra underneath. The outfit, which accentuated the charms hidden beneath, was completely inappropriate for the corporate environment. The office staff shook their heads in disbelief. Didn't this tart realize she was at a fortune 500 company, not some sleazy tavern? Was she a job applicant or a staff member's rebellious kid?
Steve, sitting across from the teen sexpot, found himself tongue-tied. Allison was the sexiest creature he had ever laid eyes upon. The girl's dark shoulder-length hair seemed to shine, and her shape made Steve's little penis tingle in his trousers. Her hips were slim but her narrow waist accentuated them and her breasts, which had such an enticing shape, rested high and proud on her chest. Steve noticed the outline of her nipples through the blouse and Allison smiled to herself when he failed to extend his hand to shake hers. His eyes were fixated elsewhere.
By any measure, Allison wore too much makeup for a corporate office, but Steve certainly didn't mind. The teen's dark red lips seemed moist and ripe to the married man and he found that the scent of her perfume made it hard to concentrate. Her olive skin looked so smooth and flawless that Steve almost reached out to touch her cheek. She smiled at him knowingly and the older man felt himself blush awkwardly under her gaze.
Compared to the other applicant's qualifications, Allison was entirely out of her depth -Steve knew this. Somehow, though, The nineteen year-old smiled and flirted and goaded him on, and by the end of the fifteen minute interview Allison had convinced the forty-year-old married man to give her the job, as well as the six-figure salary that went with it. The office gossips were suddenly very busy.
When he arrived home, Steve snuck into the bathroom and began to stroke himself while thinking of the dark vixen that had so enchanted him. Steve remembered seeing her bra-strap beneath the thin blouse as she turned to leave his office. In his mind, the teen peeled off the blouse before turning to reveal her perfect ass to him. Fantasy-Allison grinned at him over her shoulder and began lowering the black skirt over her the tight globes of her firm buttocks and the thought brought him to the edge of orgasm. Steve screwed his eyes shut and quietly rubbed the shaft of his little cock then squirted all over his hand and the bathroom floor. The entire episode had lasted two minutes.
Afterwards, the doting husband was racked with guilt over his lustful thoughts and the betrayal of his wife that he felt they indicated. Steve was also embarrassed and worried about what his staff would think of him and he knew that the higher-ups at the company would certainly not approve of his choice of secretary. Suddenly Steve felt that both his career and his marriage could be profoundly affected by the rash decision to hire a girl who was young enough to be his daughter.
That night as he settled into bed, Steve felt himself unbelievably excited to see Allison in the morning. As he lay beside Lana, his penis stiffened to its full four inch length. Steve considered trying to get his wife to have intercourse with him but instead waited until she fell asleep. Steve quietly slipped into the bathroom where, for the second time, he jerked off thinking about his new secretary.
Allison arrived twenty-five minutes late for her first day of work. For a while Steve felt like he had been stood up on a date, and he sat by his window watching the parking lot until she arrived. When he saw her swing her shapely legs out of the small car, his stomach jumped and he felt his soft penis stir in his pants. Steve realized that he was in danger of getting a hard-on there in his office. Even though he knew that the bulge in his trousers would be anything but prominent, an erection, even a small one, can be very awkward.
He spent the morning showing Allison around and explaining her daily tasks to her. Although she had poor computer skills and couldn't type a lick, Steve could care less.
When he introduced her to the rest of the office, Steve could tell that most of the staff -especially the women- disapproved. He had always been so respected by everyone, but was suddenly being reevaluated by his coworkers, many of whom he had known for ten years. When male co-workers leered at the teen - dressed only slightly less provocatively than yesterday - Steve's jealousy welled up inside him. She was HIS secretary, damn it. Not theirs.
As days passed the office settled back into a routine. Allison flirted with the guy from the mail room and Steve pulled some strings to have him transferred to another department. He sensed that he had lost the respect of much of the office and that bothered him immensely. Additionally, Steve found himself constantly having to do secretarial tasks himself as Allison's work ethic was terrible. The teen had the older married man wrapped around her finger, and both she and Steve knew it.
Steve especially enjoyed helping Allison with her computer. He could secretly look down her blouse while leaning over her shoulder. On a few occasions, Allison hadn't worn a bra and Steve had been able to see her nipples while peering down the V of her blouse. Steve had become erect on one such occasion and Allison giggled when she noticed the little tent in his trousers. The older man blushed and hastily excused himself to the safety of his executive bathroom. He wondered if the teen suspected what he did behind that locked door.
Two months after Allison was hired, one of the company's senior VPs retired. Steve had been hopeful that he would be picked to replace the man, but a less-senior female manager, Sandy Everington, was chosen in his stead. The promotion made her Steve's supervisor. Steve chalked the slight up to the company's need to add a woman VP, but he wondered if his indiscretion in hiring Allison was part of the reason he was passed over. Nonetheless, Steve and Lana prepared to attend a party at the Everington house for all the company's senior staff.
Steve dressed in his usual office attire and Lana wore her best outfit. The middle-aged wife's skirt reached midway down her calves and she wore an austere sweater over her tan blouse. While watching Lana dress, Steve wondered briefly what his wife would look like in a more current fashion -something that Allison Smith would approve of. He could hardly imagine it.
Sandy Everington's house was impressive. She had divorced her husband several years before and received a substantial alimony payment each month on top of her salary. Steve had always been intimidated by Sandy. She was an attractive redhead who was well-spoken and always seemed to be dating some ultra-successful guy. Sandy was proud of her athletic abilities and she sometimes bragged about completed marathons or having biked challenging trails. Steve sometimes got the sense that Sandy looked at him as inferior because of his pudgy physique and his lack of interest in sports or fitness.
Steve occasionally encountered women who seemed to instinctively know that he was sexually lacking and he noticed that once they sensed his shortcomings they were dismissive of him. Sandy was one of these women. Oddly enough, this dynamic always made Steve lust after the woman in question and he felt a powerful surge of submissive desire around them. Steve often found himself distracted and stumbling over himself in her presence, and he was sure that having Sandy as a supervisor would greatly hurt his standing in the company.
While mingling with the partygoers, and trying to avoid the hostess, who looked terribly sexy in a thin summer dress, Steve noticed something odd: in addition to management, most of the secretarial staff seemed to be in attendance as were workers from the warehouse and the retail offices. Steve supposed that the new VP was using this opportunity to show off her wealth to as many people as possible.
Steve was scanning the crowd with Lana on his arm when he felt a tap on his shoulder. There, accompanied by a handsome athletic man, was Steve's secretary. His voice caught in his throat as his eyes wandered over Allison's tight body which was proudly displayed in a revealing shirt that exposed her midriff and a pair of hip-hugging shorts. After an awkward moment waiting to be introduced, Allison stepped past Steve and offered her hand to Lana, "Hi, I'm Allison, Steve's secretary. Pleased to meet you."
Lana was surprised. Steve had never mentioned his gorgeous young secretary. She shook the teen's hand and smiled politely. Lana examined Allison as the young woman introduced her date. Steve's secretary looked like a dancer or a model from a men's magazine. Lana had thought that her husband was still trying to fill the secretarial position and she felt betrayed and jealous to find out about Allison this way.
Another powerful emotion gripped Lana as she watched Allison engage in conversation. For the first time in a long time the housewife felt a rush of sexual attraction. Lana found herself engrossed by the sight of the teen's stunning eyes and dark red lips. The housewife began to blush for seemingly no reason.
When Allison looked at the older woman's face, Lana was certain that the young vixen knew what she was thinking. Lana couldn't mask the jumble of emotions -jealousy, awkwardness and attraction- that overwhelmed her.
Lana wondered if her husband also felt Allison's sexual spell. Did he really work with this beautiful woman every day? Lana felt unattractive and inadequate next to the teen seductress.
Unsurprisingly, the shy housewife didn't join in the conversation much as the couples made small talk. Lana's sudden sexual attraction was both surprising and unwelcome. She was reminded of the feeling she got when, as a young girl, she would use a flashlight late at night to secretly look at the pictures of boys in teen magazines, but Lana had certainly never felt such an attraction to a woman. In fact, it had been so long since the housewife had experienced this giddy feeling that she had almost forgotten it altogether.
Whenever Allison caught Lana staring at her, the teen held her gaze with a knowing smile until Lana looked away submissively. It seemed to the housewife that the young brunette could somehow see beyond her conservative exterior into the passionate place that was suddenly awake inside her. The teen never said anything untoward, but the way she looked at Lana made the older woman feel vulnerable.
Lana, lost in her thoughts, let out a surprised squeak when she felt someone touch her on her shoulder. It was Allison's date carrying four glasses of wine in his large hands. What was his name? Lana couldn't remember. She'd been so distracted during the conversation with Allison that she was hard pressed to remember anything that was said. She smiled at the handsome college student and accepted a glass of wine. The nervous housewife gulped the drink to calm her somewhat frazzled nerves.
Allison and her date moved on to mix with the other guests. Lana felt relieved. She worried that she was embarrassing herself and that someone watching would read in her expression the jumble of feelings she was fighting to suppress. She felt like she needed to catch her breath and she left her husband for a moment to procure another glass of wine.
While at the bar Lana was approached by Sandy Everington. The attractive hostess smiled as she approached Lana. The two had met at several company events and Lana always felt like Sandy had pegged her as a bit of a square. It seemed to Lana that Steve's new boss got a kick out of teasing her and making slightly off-color remarks to see how the more conservative woman would react. Sandy asked "What do you think of Steve's new secretary?"
Lana was at a bit of a loss as to an acceptably polite reply. She finally settled for, "I like her. She's nice." Sandy wasn't buying it.
"She certainly is well put together. I don't know how Steve gets any work done. I would be too fucking distracted." It had taken less than thirty seconds for Sandy to succeed in making Lana blush.
The business woman enjoyed teasing the shy church-going wife. "Did you notice Allison's date? What a hunk. And did you see the size of his hands? You know what they say about guys with big hands."
Lana shook her head. She had no idea what the young man's large hands implied.
Sand leaned over and whispered in Lana's ear, "big cock." Lana's eyes widened and she blushed furiously as the hostess walked away chuckling with amusement.
As the night grew on, Steve became more and more concerned about his wife. She had consumed five glasses of wine -about three over her limit. She was conspicuously quiet and seemed lost in thought. Steve was terrified that his wife was furious with him. Did she suspect his obsession with the teenage girl? Was she contemplating divorce?
Steve kicked himself for not telling his wife about Allison. He could have made up a cover story. Lana would have understood if he had said that the sexy teen was someone's relative -that he had hired her as a favor. But now it was too late. Steve was certain that his conservative wife knew he was a pervert and a letch.
The married couple stood side by side at the party, each failing to understand what the other was thinking. In this way the night was not unlike many others they had shared since the beginning of their marriage.
As the party began to dwindle, Steve and Lana sat quietly in the corner. Her head was buzzing with too much alcohol while he fretted because he sensed that Lana was upset. Allison and her handsome stud, Robert, approached the dowdy pair. "You two need to come out with us. We're heading to a great after hours place. They don't close until three."
Steve began to make his excuse when he was interrupted by Lana who nodded her head furiously and said "yes" with entirely too much enthusiasm.