Librarian Finds Long Overdue Love Ch. 17

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Tom escorts Angelina into New York for a kinky shopping trip.
6.6k words
4.15
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Part 17 of the 31 part series

Updated 01/02/2024
Created 04/10/2013
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RVon
RVon
42 Followers

January 23, 1988

Single, middle-aged and bespectacled Angelina Lione may look the part of the prim, proper and sexually repressed, buttoned-up bibliothec, but she's most definitely NOT your father's librarian - at least not while in a lover's company. Blessed with a ravenous and unquenchable sexual appetite, Angelina's orgasms are so intense that she oftentimes faints during the throes of passion.

While never mistaken for a perfect 10 with her large brown eyes, tucked behind oversized, Diana Prince-style eyeglass lenses, Angelina still cuts quite the desirable figure, with a fetching face always perfectly and tastefully made up, and a sleek and shapely body. Her short, black hair, speckled with gray, was cut in a chic, wedge/pixie-style, puffed and piled on the top and curled forward around the ears. Angelina's attractive physical traits, however, always paled in comparison to her overwhelming sex appeal. Using her vast store of feminine wiles, Angelina negotiates about her lovers' hearts, minds and bodies as deftly as she navigates the Dewey Decimal System, manipulating infatuated men for her monetary and personal gain.

High maintenance and even higher fashion, Angelina always models the latest designer threads - oftentimes accentuated by any one of her dozen pairs of high-heeled dress boots. Her sophisticated look even extends to smoking accessories. The haughty diva wouldn't dream of smoking a cigarette if it wasn't filtered through her long, black holder. More of a cigarette holder sucker and stroker than a smoker, Angelina seductively works the black shaft with her mouth, tongue and fingers as if it was a penis proxy; the effect that playing with the long, stiff holder has on would-be lovers is like snake charming. Under the sexy siren's magic spell, they're entirely at her mercy; powerless to resist the temptation to pleasure her - as if they really would.

Angelina spent her 20s and 30s as a fully-committed member of the sexual revolution of the 1960s and '70s - bedding dozens upon dozens of men. Only when she reached age 40 did her love life settle down - for her anyway - when the lusty librarian entered into a long term, nearly exclusive, torrid affair with the principal at her school. After the forbidden relationship unceremoniously ended six years later, Angelina found herself alone at a time when her peers had long since settled down into blissful domestic life. A prolonged romantic dry spell followed, until a former student unexpectedly burst into her life.

Twenty-two year old Tom Bailey had been in lust with Angelina since he was a 13-year-old student of hers, drawn in classic fetish fashion to the sexy librarian's stylish, high-heeled boots, seductive smoking and even her pretentious and snobbish personality. Over the past nine years his feelings - like his fetishes - for the femme fatale only grew stronger, until he could no longer keep them to himself. The pair had just launched an intense, physical relationship when Harry Seymour, Angelina's old boss and lover, re-entered her life. Unable to decide between the two romantic suitors, Angelina proposed a date-off - or "fuck-off" - as Tom bitterly described the arrangement.

Now, with her love life once again in full bloom, the amorous woman was in sex heaven - reliving her youth, when men practically lined up around the block to date her. Preying on the men's sexual addiction to her, Angelina gleefully bounced between their beds for nearly a month, until Tom finally prevailed.

The love triangle finally broken, Angelina and Tom were finally free to embark on a committed, loving relationship. But the couple's path to romantic bliss was lined with a phalanx of challenges - not the least of which was familial. During their first fortnight together, Tom met Angelina's family - and had been unnerved by her brutish and overprotective brother-in-law.

It was a couple months into their relationship before Tom worked up the nerve to introduce Angelina to his folks. The encounter set off a tremor that was bound to trigger aftershocks along the fault line of their courtship. The meeting with what turned out to be an old work adversary so unnerved Tom's mother, in fact, that she subsequently resumed a long dormant smoking habit.

That introduction went poorly enough, but how would Tom's college friends react to seeing him with a much older woman? What would be their impression of her? What would he see in her? Sure Angelina was attractive enough - but she was an attractive older woman. Why would young Tom be interested in a 50 year old, when there were plenty of lovely ladies his own age available? And when they got a whiff of her pompous and bitchy personality, they'd really question what was in this relationship for Tom and the age difference would be even more pronounced. The very real possibility existed that they'd disapprove of this affair, judging Tom a weirdo and mere boy toy to Angelina's dirty old woman.

Private by nature - and especially embarrassed to confide in anyone about his smoking and boot fetishes - how could Tom possibly explain to them that Angelina embodied all that he found physically alluring in a woman? How every time he saw the haughty diva smoking from a cigarette holder or strutting about in a pair of delicious, high-heeled, knee-high leather boots it made his dick dance and pulsate with delight. Or that when every time he and this MILF-before-the-term-was-coined made love it brought him to heights of pleasure he never dreamed possible.

To temporarily escape from and forget their family pressures, the May-December couple took a romantic Caribbean cruise over Christmas break, 1987. The getaway was just what the doctor ordered - if the physician in question was noted sex therapist Dr. Ruth Westheimer, anyway. Tom and Angelina engaged in a month's worth of uninhibited and lusty sex in just one week. It was like their weekends back home - only uninterrupted by family and work obligations - when they oftentimes enjoyed thrice-daily, intense and passionate lovemaking. In these heady, early days of their dating life, Tom felt like he was attending a sex fantasy camp with his boyhood crush, while to Angelina, she was thoroughly caught up in the joy of what could be her last shot at romance and passion.

Still, for as much fun as they were having, Tom began to have grave doubts about how their relationship, such as it was, was evolving. To him, it seemed like all they did was make love. They didn't really talk or act like a textbook dating couple, and this concerned him. While Tom wasn't complaining about having the best sex of his life whenever, and practically wherever, he wanted it, the young man couldn't shake the nagging feeling that maybe he was only keeping Angelina's bed warm until the next in a long and varied succession of lovers came along. Perhaps one who was closer to her age and who had a career that allowed him to spoil the materialistic woman more consistently than Tom, with his entry-level publishing salary, could afford to.

Tom took heart in the prospects for their long-term relationship that Angelina went mad with jealousy when his ex came to town for a recent visit. But even someone as young and romantically inexperienced as he knows that jealousy doesn't necessarily equate to love. He needed more evidence that Angelina considered him more than a mere fling.

----------------------------------------------------------

"You're up early for a Saturday. What for?" asked a sleepy-eyed Paul, emerging half dressed from his bedroom to find his roommate, Tom Bailey, sitting in a chair in the living room of their Hoboken apartment, showered, shaved and wearing a winter jacket.

"I'm going clothes shopping in the city with Angelina, she's picking me up at 10:00," he responded, glancing at his wristwatch that now read 9:58 a.m.

"Shopping?! Man, you've got it bad. Better watch it, buddy, or you'll have a serious girl friend on your hands."

I hope so, Tom said to himself. Boy, do I hope so.

Desperate to break free from what he believed was an endless loop of nonstop sex, the young man yearned for a substantive relationship with his on-again, off-again lover of nearly three months, 51-year-old Angelina Lione. A day of shopping may seem like torture to Paul, but to Tom Angelina's invitation represented a meaningful step in their romantic life. They were finally engaging in a normal, dating couple activity; something that didn't involve jumping into bed together.

Bzzzzzzzzzzzz

"Oh, that's her," Tom said, launching from the chair and pressing the intercom button by the front door. "Hello, Angelina?"

"Yes, darrhhling, I'm here," crackled his girlfriend's voice over the squawk box in her exaggeratedly sophisticated and snobby tone. "Are you ready?"

"Be right down."

With a hand salute to his roommate, Tom opened the apartment door and was gone. Not wanting to keep Angelina waiting, he bypassed the elevator and instead ran down the three flights of stairs to the lobby where he found his girlfriend sitting cross legged on a chair. Looking casual yet chic and elegant in a crème-colored, cardigan jacket coat top with matching leather knee high, high-heeled boots tucked into a pair of tight and tan pleated trousers, the forever fashion plate had a burgundy mink stole wrapped around her neck to protect against the 26-degree chill of a late January day.

"Good morning, darrhhling," a smiling Angelina said, unfolding her booted legs and rising from the chair to greet her lover with a hug and an air kiss as she turned her head so his lips only connected with her right cheek. "Shall we?"

Tom was hardly surprised at the seemingly passionless response normally reserved for a platonic friend, not an intimate lover. For as sexually insatiable as Angelina was, he also knew his much-older girlfriend came from a more socially-conservative generation where public displays of affection were generally frowned upon. Nonplussed by the passionless kiss a mother might give her son, Tom performed his gentlemanly duty and promptly opened the front door of his apartment building. Angelina slipped on a pair of Foster Grant sunglasses over her prescription eyeglasses and arrogantly strode through the door, toward the curb and her parked, freshly washed, late-model, red Volkswagen Scirocco.

"So, where to?" Tom asked, when the two were settled in the front seat of the car.

"Well, first stop is Sak's Fifth Avenue," Angelina replied. "I have an appointment with a personal shopper in a private fitting room at 11:00."

"First stop?"

"Oh, yes. From there, it's to Bergdorff Goodman and then Bloomingdales."

"Three stores?!"

"Yes, is that a problem, darrhhling? Do you have other plans today?"

"Oh, no. It's just that those are some upscale, expensive places. How can a school librarian afford to shop there?"

"You forget, my dear, I've been working for quite some time and I have no dependents. I have quite the nest egg built up. What else do I have to spend money on but clothes? This is my one big shopping trip to the city, that I make each year to check out the new fashions and treat myself to glamorous clothing that's terribly expensive and impractical. After all, fashion is my favorite past time...well, second favorite, as you personally know very well by now. Right, darrhhling?"

"Ummm...right. Okay, but you said you have an appointment with a 'personal shopper.'"

"That's right."

"I guess I don't understand then. I mean, it's great you asked me to come with you, but if you have a personal shopper lined up to help you, why do you need me, other than maybe to keep you company on the drive? I sure won't know any more about what to buy than a professional fashion expert."

"Oh, I believe you'll be quite useful to me on this little shopping excursion, darrhhling," the sophisticated and sexy woman said. "I trust your taste in fashion more than you know."

Angelina grinned devilishly at her lover, gripped the stick shift with her black-leather-gloved right hand, pressed the clutch to the floorboard with her booted right foot, then downshifted into fourth gear, as the Scirocco raced up Clinton Ave. toward the Lincoln Tunnel for the six-mile drive into Manhattan.

Half an hour later, Angelina pulled the car into a parking garage strategically located in the middle of the three midtown department stores and the couple strolled the short distance to Sak's. It was the first time Tom had ever entered the legendary store and even a self-confessed fashion dolt like him couldn't help but be awestruck by the elegant displays of glass and class.

In contrast to the young man's unfamiliarity, stood Angelina. As a yearly visitor to the store, she knew her way about the floorplan as if it were her second home. Making a beeline for the escalator, with Tom in tow, the two rode it up to the second floor. At the top, Angelina took a right turn and led her boyfriend through a maze of aisles dotted with handbags and glittering jewelry until they reached a checkout counter at the far corner of the floor.

"Hello, madam," the attractive 30-something-year-old brunette behind the counter said. "May I help you?"

"Yes, you may," Angelina said with an air of sophistication and conceit in her voice. "I'm Angelina Lione. I have an appointment at 11:00 for a private fitting of evening gowns, dresses and formal wear."

"Oh, very good, Miss Lione. My name is Juliette. I'll be your personal shopper today. I've prepared a number of gowns and dresses for you to try on. So, if your son would like to meet us back here in an hour, I'll escort you to your dressing room."

Angelina looked at Tom, then turned back to the personal shopper.

"He's NOT my son!," Angelina shot back in reserved but obvious agitation, as if she were at school scolding a student. "He's my boy ta...my boyfriend... and I want him to be involved in this session. And my name is NOT 'Miss', it's 'Ms.""

Did she almost call me her 'boy toy?' Tom asked himself, unsure of what he just heard. She did call me her 'boyfriend,' but I could swear she started to call me her 'boy toy.'

"Oh, I'm terribly sorry, Ms. Lione," said the embarrassed woman. "Please, follow me."

Juliette led the May-December couple behind the counter to the private fitting area.

"Please, sir, make yourself comfortable," she said to Tom, motioning to a plush leather chair in front of the curtained fitting room. "Would you care for a beverage?"

"No, thank you, I'm not hungry," said the clearly distracted Tom, still turning over in his head what Angelina may or may not have referred to him as.

"Right this way, Ms. Lione," the personal shopper said, holding the curtain to the fitting room open for Angelina.

For the next 10 minutes, Tom replayed her statement to the sales lady dozens of times, alternating between questioning if his ears had deceived him and confident that he heard correctly.

"What do you think, darrhhling?" Angelina asked upon her return, startling the young man from his obsessive daydream.

"Oh...uh...it looks great on you," Tom said unconvincingly, as his girlfriend stood before him, hands on hips of the red Halston gown with the slit in the front that revealed her booted left leg and most of her thigh.

"That's it? Just great?"

Angelina slowly twirled, then stopped, so Tom could get a look at how the frock complemented her shapely butt.

"Well, yeah, you look great in it," he repeated.

"Hmmm...okay," Angelina said, retreating back into the dressing room with confusion etched on her attractive face, surprised that the sight of her in the sleek and sexy gown hadn't piqued his interest more.

Next up in Angelina's personal fashion show was another Halston number - a black, off-the-shoulder drape gown. Strutting about the room, she finally cocked her right hip to allow the slit on the left side of the formal evening wear to show even more of her sexy, high-heeled, black knee boot than the first dress did.

"Well?" she asked, arms hanging straight down at her side next to her hourglass figure.

"Lovely," Tom said, his mind clearly elsewhere.

Annoyed at the repeated lack of input from her young lover, Angelina stormed back toward the fitting room, flinging back the curtain in anger as she entered.

The scene repeated itself a half a dozen times more over the next 45 minutes, before Angelina finally settled on the first two numbers. With her bank account some $800 lighter and Tom's arms about 8lbs. full of boxes containing Angelina's latest designer gowns, the two exited Sak's and headed up 5th Ave. in search of lunch.

"What are you in the mood for, darrhhling? French? Italian? Chinese?" Angelina asked, pausing outside Sak's front door to affix a Virginia Slim into her long black cigarette holder. "Shopping always makes me famished."

"Whatever," Tom said. "It doesn't matter."

"What's wrong, Thomas? You've been acting peculiar ever since we got here - and you were not terribly helpful to me in there."

"I think we need to talk."

Tom shifted the packages from his right arm to his left and gently took Angelina's elbow, guiding her close to the side of the building, out of the way of other shoppers and passing pedestrians.

"What is it darrhhling?" Angelina asked in concern.

"Remember when you corrected the sales lady in there about me?" he questioned. "I coulda sworn you started to call me your 'boy toy' before you caught yourself."

"Is that what's been troubling you?"

"Well, yeah."

"But I called you my 'boyfriend."

"I know. I know. But it didn't sound like that at first."

"Darrhhling, I think all that rock music you play on that electric guitar is affecting your hearing. I called you my 'boyfriend'.

"Yeah, it's just..."

"Now, stop all this foolishness and give me a light, will you? I need to get something to eat. We've still got a lot of shopping ahead of us and if I don't get some nourishment I'm going to pass out from exhaustion."

"Yes, Angelina."

With her black-gloved right hand, Angelina inserted the holder between her lips and patiently waited for Tom to finishe fumbling about with his packages so he could dig a hand into one of his pockets and fish out his lighter. After finally finding the correct pocket, Tom flicked the lighter and held it up to his girlfriend. Angelina accepted it and after taking the shallowest of inhales, slid the moistened black tip from her lipstick-coated mouth as effortlessly as Tom's penis glides out of her mouth during oral sex.

Turning about to walk down the street, Angelina caught a glimpse of herself in Sak's storefront window and paused, with a knowing smile, she admired the glamourous reflection; the stylish sunglasses, sophisticated cigarette holder and sexy-as-hell boots in all their glory. After taking a shallow pull from her holder and blowing out a soft puff of smoke, the vainglorious woman set off down the street, leaving her boyish boyfriend juggling her packages and struggling to catch up.

Following a casual lunch at a nearby Thai restaurant, the couple resumed their shopping trip - this time for lingerie at Bergdorff Goodman's on 5th Avenue between 57th and 58th Streets.

Angelina wasted no time turning up the heat in the private fitting room. Modeling a flower-embroidered green balconette bra and matching thong, the middle-aged librarian got her boyfriend so hot and bothered that he was nearly willing to pawn his beloved electric guitar and amplifier to help bankroll it. But at $900, Angelina declined to purchase it. Still, the outfit had done its job; she now had his full attention.

"How's this?" she asked coyly, her booted legs stepping in the room to show her off the lace-hem, silk chemise nightgown that hung about her chest.

"Wow!" was the only comment Tom could give, as he sat up on the end of his chair and stared hungrily at his sexy girlfriend.

RVon
RVon
42 Followers
12