Total Woman Odyssey Ch. 03

The first portion of this story was previously published as part of Total Woman Trainers Ch. 06. I have republished it here with some changes and continued into an expanded story. Please vote, comment, and enjoy.

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** Cate Cassidy 01

Cate was born Catherine to an affluent couple in an upscale Connecticut ex-burb. Her mother descended from 'old money' and her father, a hard-charging New York City financial lawyer, had considered his wife the perfect match: wealth and beauty. He had wooed and won the Scottish heiress and used her money to run up his own sizeable fortune.

But fortune was not as kind in their home. His wife turned out to be a sexually aloof woman who, after having done her duty by delivering Catherine, lost all further interest in sexual congress. The marriage devolved into an arrangement where the husband spent his weeks in Manhattan and maybe half his weekends back in Connecticut.

As she grew and matured, the daughter's name morphed through childhood as Cathy, to teenaged Caty in her preppy high school to her current collegiate age moniker of Cate.

Her pre-college influences came mostly from her mother, a socially challenged suburbanite who wanted her lonely life validated by creating a kindred spirit, instinctively steering her daughter towards the same sexually-repressed existence.

By fate alone, Cate lost her virginity on prom night to one of her exclusive prep school's football players, a painful non-event where she lay motionless as he rutted at her groin. Its only purpose was to get equal post-virginity status with her more outgoing clique mates.

As her high school days were ending, her parents explored various high-class universities. Ivy League was a foregone conclusion. But her father wanted a more rounded education and leaned on his network to achieve his aims. He generated Cate's Scholarship Referral from his TWA Pledge Contributor network which he had developed through his regular attendance at Guest Coach Tutor events; of course, without Cate's or her mother's awareness.

Cate's mother wanted her daughter to be like her, a coy chaste wallflower. On the contrary, her business scion father wanted to be a Wall Streeter cock chasing wild thing, a future deal closing aid in his drive to financial dominance. He wanted his demure daughter's life enriched by the TWA curriculum, nixing her mother's suppression of Cate's sexual passions, hoping to grow her into a viable helpmate in his fiscal empire.

His TWA colleagues had met Cate at family and community gatherings. They found her demure character both charming and provocative. They saw that she was socially detached and almost never smiled. They suspected she was perpetrating a shrewd subterfuge and speculated that she cloaked a vivacious libido underneath the sour disposition.

"Aren't you fucking her yet?!" his friends chided him.

His shifty denials only fueled their fantasies and gave his locker room standing a bogus boost. They complained he was hogging her succulent pussy all to himself.

After all, he was freely fucking their female offspring on his frequent visits to TWA campus events. They nagged him incessantly to enroll his nubile daughter and divvy up his selfish hoard of her sexual gifts.

"Fair is Fair" they whined, "Caring is Sharing".

He desperately wanted to bed his little beauty but hesitated; it wouldn't be easy. If her mother suspected anything, well... divorces are fickle affairs. He loathed letting go of any of the family bankroll, let alone a potential half. So her mother must remain oblivious to his intentions for Cate's coital incursion into the exotic realm of elite alpha males.

Still, he was dying to have TWA acclimate her to physically gratifying older males as part of her TWA guest coach tutor encounters. That would be the deeply gratifying component of her poise curriculum. After prep school graduation, or sooner if practical, he wanted to leverage her erotic participation in closing some of his stalled business deals.

And he was not himself immune to her shy sexual allure. He looked forward to the time when TWA unencumbered her mind from her mother's prudish brainwashing. A time when they made her accessible to him like the other TWA coeds he fucked, but especially during Father-Daughter Weekend, although he prayed it would happen sooner.

That fall, her parents enrolled Cate in the coveted Ivy League college, Cornell University, tucked away in the vineyards and wineries in Upstate New York's Finger Lakes. And keeping with her superior affluent standing housed her in a converted downtown boutique dormitory, an old Victorian mansion. Accommodating just four bedrooms, the shared common areas were equipped with modern luxury furniture and fixtures.

Cate never really emerged from her homebody routine, engrossed in reading poetry, shunning any attempts at campus social interaction. But fate has a way of moving things forward.

Cate's housemates, unknown to her as recent TWA graduates, encouraged her to answer an anonymous summons and clandestinely abetted the TWA Recruitment's vetting. The institution then apprised Cate of the elite scholarship availability.

The Recruiters shared vague highlights of the tri-fold curriculum, and its prerequisites for enrollment, including a decision making evaluation assessment of her basic feminine maturity by a TWA Coach Tutor.

"Will I be able to pursue studies in poetry?"

"You will be challenged to embrace the depths of your passions and sensations in TWA's lively and exhilarating romantic curriculum" they assured her.

Unadventurous by nature but foreseeing some life enrichment possibilities, she agreed.

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"ITH, Ithaca Thompkins Control, this is TWA 001, requesting a vector for landing."

"TWA 001, this is Ithaca Control, proceed to the outer marker for Runway 32. Winds from the north, 5 MPH, gusts 20 MPH. Welcome to the Finger Lakes, sweetie."

Krystal rolled her eyes; she was only a 'sweetie' now?

"Roger that, Control."

She keyed the intercom.

"Seven minutes to touchdown, sir. Please buckle in."

Ned had already secured himself and peeked outside at the low rolling hills of Upstate New York. The countryside was a patchwork of private vineyards and the pressing vat barns, filled with last fall's harvested barrels of wine, aging and waiting to be bottled and distributed for the regional consumption. The wheels bumped down, and the plane shuddered as Krystal reversed thrust, slowed, and taxied to the terminal.

Per routine, she shut down the engines, trotted down the foldout stairs first, and gave directions to the ground crew to have the jet fueled and ready for takeoff tomorrow. She focused again on her VIP passenger.

Krystal escorted Ned to the black town car waiting on the apron, opened the rear door, and seated her alpha male charge inside. She wheeled the car from the airport, down Route 13, towards the town of Ithaca, overlooked by the Cornell University campus perched on a ridge beside Cayuga Lake.

Ned had reviewed the assignment package in flight. It described Cate and her background and spurred his thoughts on his approach to her erotic emergence.

Ned's challenge was to tease out Cate's repressed sexual decadences. He knew she had them, those same buried carnal passions innate in every fertile woman, even chilly ones like Cate and her mother. He must go slow and easy, not spook her, but still move her steadily towards the primary goal. And he only had one night.

He strolled into Carl A Kroch Library to the William Wordsworth Collection. He found her serenely waiting for him at a tucked-away reading space at Kroch Library.

She was folded into a big comfy chair: green headband, plaid skirt, turtle mock neck green sweater, low heeled walking shoes. Her long thick auburn hair lay down her front and back. She was reading a book of poetry.

Ned quietly greeted her. He asked what she was reading. It was "Perfect Woman", a 19th Century short poem by William Wordsworth, her personal copy since the original manuscript was stored hermetically within the nearby Rare Manuscripts Collection. She just liked being close to it, as if the original manuscript's romantic aura could seep through the protective walls and into her heart.

She knew he was coming. He said they should get started, and gave a hand, helping her out of the chair.

She asked whether before the formal interview began they could first attend a Bohemian café poetry reading nearby so he could get an impression of her present life passions. The real-life example might help him jumpstart the interview.

Ned was already enthralled by the eye-catching redhead and thought he would prefer jumpstarting her interview by jumping right into bed. But with curiosity and professional patience, Ned abided her request and she led him to the nearby smoky, low lighted bar.

They sat at a small table, each with a glass of local merlot. He watched her emotionally burble sweet nothings under her breath as the wimpy onstage presenter nasally intoned his non-rhyming tome.

Ned recognized that her romantic admiration for these shallow toadies would bode well for the staff and guest coach tutors. They would get an ego boost from bursting through her prim preppy shell and forcing her body and soul expeditiously and deeply into the TWA poise curriculum.

But not yet. She needed to be gently drawn to her fated future.

Ned maintained his amorousness subterfuge as they strolled in the chilly spring evening through the street-lamp lit town, his arm across her shoulders, holding her body close.

He halted their walk several times for sweet touching in shadowed places. Cate behaved complaisant and unaccommodating as any shy young lover would.

He stopped once to press her back gently to a wall, she looked down and away but his index finger lifted her chin. She closed her green eyes as she bashfully accepted his light kiss on her lips.

Ned huddled his arm tighter on her shoulder, walking slower, closer together. They traveled a bit further and he stopped her again in a doorway alcove.

She tilted her face up, shrouded by her thick red hair. He took another light kiss from her more willing lips. His furtive hand stole inside her wool felt coat to cup her breast through the thin sweater and bra. It was warm and pliable, a fine handful of feminine flesh.

Ned's libido was hyper-fueled by her coy cooperation. Now she walked in time with his stride, signaling her growing ease in his masculine presence.

They arrived at her address, ascended the stone steps to the Victorian porch with its white painted wood columns and gingerbread eaves edging. She opened the door and they held hands on entering.

Her three roommates were lounging in the front room. Cate stutter-stepped, uncomfortable under their judgmental gazes, self-conscious about being escorted by a man at least twice her age. Ned didn't falter and kept going, towing her by the arm, a silent demand to keep up.

He perceived but didn't acknowledge the fascinated and amused stares from her girlfriends at his bold control of their normally shy housemate. His peripheral vision saw a couple of appealing ones that he might schedule for later routine TWA Fine Tuning. It was a post-graduate program just for keeping the TWA graduates primed with regular doses of alpha male cock.

Entering her quarters, he closed the bedroom door, locking it this time because it would let Cate feel safer. He undressed the redhead coed in this private space: the green wool felt coat, her gray wool pencil skirt, the green pullover sweater, and her flat heels.

All the while she looked shyly down, moving in cooperation but nothing more. He unclipped her bra and slid off her panties. She stood naked with hands clasped shyly in front, a sign that she unconsciously wanted to cover her feminine places but consciously resisting the urge in deference to Ned.

Ned saw that she was a natural beauty, a well-built body, sparse freckles sprinkled evenly from her forehead downward, and fading out at her teardrop-shaped handful of boobs. Her overall figure was balanced between proportionate chest, hips, and legs.

However, her red pubic hair was only scissor trimmed, not shaved. Her downturned green eyes were highlighted by chestnut brownish colored cosmetics, her only attempt at makeup, none for her rosy erogenous zones.

The long red hair covered her ears and half the cheeks of her lowered face, flowing down her chest and back. She wasn't playacting. This was her pure look of innocence that immediately spurred the lust of the men she met and it was working quite well on Ned, who was mulling judgmental sentiments.

'She's been left to get by on her own for too long. But the TWA curriculum will indoctrinate her with exceptional man-pleasing arts. And she will blossom like a budding flower into a full-blown rose.'

He still held the simple cotton panties which he had removed last and he stashed them in his pocket as his collected souvenir.

He didn't require her to assist him as he removed his clothes. He saw her innocent green eyes go wide on first sight of his stiffened cock. She stared at the long, thick penis with the purple knob, only the second one she had ever seen since before her virginal prom night long ago.

He steered her by the shoulders and laid her in her own bed, her singular comfort zone that he was about to violate. He eased his naked body above her, on knees and elbows, hovering himself over top of her. He brushed back her hair for a gentle kiss. Her floral shampoo and rinse fragrance filled his nose and her lips tasted like the red wine they had sipped at the poetry café.

She showed a small hint of true acceptance when she loosely hugged his neck. He embraced her body for a stable hold, one hand delving beneath her ass, the other cupping the back of her neck. It was a masculine grip, needed for the looming lunge and if she reneged her cooperation at the last minute, tighter control of her body.

He moved his hard erection into position, barely touched her vaginal portal with his cock tip. He felt her hips flinch at the contact.

This was the magic moment that stirred men's souls; the tense female's instinctive last misgivings at the ultimate intimacy with a new man. It was this moment that her father and his buddies had each dreamed of: the innocent maiden trapped beneath them, no chance for her to escape but her final act of consent not yet realized.

Those thoughts alone swelled cocks and egos with a macho sense of sexual dominance. Ned was not immune to the fantasy. Even if she balked now, it was too late. He was set to penetrate her pussy and he would not be denied his conquest. He held her ass and neck just a tad tighter, ready to do more if needed.

For a flashing moment, he felt the ghostly presence of Cate's crafty father and his old friends, hovering in the room like spectators. A faint gallery of dim faces, tart with resentful expressions, floating in the air above him. Their envious eyes watched where Ned's veteran cock was perched against Cate's novice cunt, exactly where they longed themselves to be, if not now then at least someday soon.

Their turns would come. Her years at TWA would yield them a multitude of opportunities. Each would have his chance at his own first time with her. But right now it was Ned's turn for 'first time'. His swollen cock twitched and swelled a little more at the jealous imaginings.

He held her steady and tried again, touching her plump labia gently with his spongy tip.

She reacted again but, this time, rather than a pullback, she widened her thighs out just a little more, offering him easier access for the sexual junction that she had experienced only once before. Ned pressed forward and felt her moisture wet his tip. It eased his fear of having to force her.

'So she's not completely opposed to my presence, whether outside or inside her body, just edgy as this relatively unknown act unfolds.'

He pressed half of his knob in, retreated, pressed again to the coronal rim, and retreated again, gained some moisture and another inch, and again, and again, bit by bit until he was partially in. All the while, she emitted small throaty moans.

'God, she's so tight!' he thought.

He rested a moment, feeling the compression on his knob, allowing her to stretch while bathing his cock in her juicy warmth. But he couldn't stay immobile for long. He pressed and retreated some more until he worked his erection fully inside her.

He felt her heartbeat throb on the tip. He adjusted their body angle so that he rode high on her hips; his pubic bone pressed to her clitoris.

He fucked her gently with long, slow strokes, burnishing their sensitized conjoined skin and membranes. She lay almost still. Her ass was rocked by his forceful thrusts but she was not moving of her own volition. He sensed she was struggling to control her reactions.

He sped up. She intermittently held her breath, hugging his neck tighter, pressing cheek to cheek. He felt her jaw clench whenever she did.

Three ascending breathes escaped her mouth. Cate suddenly surrendered to her passions and cried out her orgasm in his embrace, biting her lip to still the sound, fearing the embarrassment of disturbing the household.

Ned paused his pumping, heard faint girlish giggles of glee from the next bedroom. He figured the other girls were listening through the thin old walls and thoroughly enjoying the imagined scene.

Slowly, Cate relaxed her body to dwell in the tingly afterglow buzzing in her pussy. Ned held her in his tight embrace and reignited his strokes, quick piston thrusts that finished himself off in her womb, jetting his semen deep inside. His final grunts were joined by another round of next door giggles.

He stayed with her in her bed and tried her out again in the middle of the night.

They were lying prone, side by side, when Ned awoke. It was after midnight. He looked at his sleeping bedmate and rolled sideways towards her. Her firm nubile boobs lay open to his view. Her dense freckles spaced out as they swept from her neck to her upper cleavage, becoming almost nonexistent around her areolas.

He stealthily moved a finger to trace the outer border of the claret wine-colored disk. He touched his fingernail imperceptibly and scraped a full circle, reaching across and rounding the other one. The center nubs rose up ever so slightly.

Cate's drowsy eyes stirred opened; she was awakened by a weird tickle on her breasts. She lay quiet at first, her mind clearing while she took stock of her situation. She was in bed, her own bed, and a naked man she had met only today lay next to her. Her pussy still tingled with the lingering afterglow of this new experience of sexual ecstasy. His finger was moving on her nipples. He craned his neck and planted a kiss on her cheek.

She turned her face to his and accepted his second kiss on her lips. He shifted and lifted his body up and over hers. She was more willing now, opening her legs as he crawled atop her. He positioned their bodies and repeated his cramped insertion, bit by bit, easier this time with her growing sexual awareness.

Ned took his leisure now. With both his hands under her ass, it helped roll her hips to get a nice massage on his under-corona. He stretched up, got mounted high on her pubes, stimulating her clitoris on each full depth bump. He felt his chest roll her supple nubile boobs between them as his body slid over hers.

He built his pleasure steadily until he heard her telltale ascending breaths. He let himself go just as she joined him in another bout of rapture. The orgasmic outburst was met with silence this time, unheeded by her slumbering housemates.

Cate lay awake afterward, pussy throbbing with even more pleasure, staring at the ceiling as Ned dozed beside her. Her thoughts were befuddled by her first-ever orgasms, induced by a man she had just met. She considered him her first true man, discounting her rutting virgin termination last year. Were these the promised worldly pleasures awaiting her at TWA? She really hoped so.