This story has elements of humiliation (including small penis humiliation), older-younger sex, and cuckolding.
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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.
