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Recent college graduate Tom Bailey stood poised at the entrance to his old middle school library like an anxious puppy waiting at the back door of his owner’s house. Nervously, Tom raked his fingers over his hair and straightened his tie with a sweaty hand.
Would he summon up the courage to knock on the door and finally reveal his love for his grade school librarian, or slink away and keep those feelings to himself as he’d done for the last nine years?
At 22, Tom thought he was finally old enough to maybe have a chance with the longtime object of his affection: Angelina Lione; old enough that his love wouldn’t be dismissed as a mere crush. No, crushes don’t last nine years. This was love and he intended to act on it, if only Tom could get up the nerve to knock on that door.
Sure, Angelina had to be at least 50 by now, but there was nothing Tom could do about the vast differences in their ages. Now was the perfect time to strike, while he was single and Angelina, hopefully, not too old — or worse married. He just had to hope that the sexy librarian he’d fallen in love with nearly a decade ago still looked close to how he remembered her.
If nothing else Tom had to knock on that door and take that first step to getting his love off his chest. No one — not even his closest friends — knew of his feelings. He was too embarrassed to tell them. After all, 8-9 years earlier Angelina was in her early 40s — she could have been old enough to be his mother.
Angelina never wore a wedding band or engagement ring, helping to fuel rumors amongst the student body that she was a lesbian. “Her hair’s too short,” went the popular argument, to which Tom countered to himself But it’s nicely shaped, curled around the ears and puffed a bit on top. Plus, she always applies a light touch of makeup to her face, whereas stereotypical lesbians didn’t use any makeup. There was nothing remotely ‘butch’ about her look. “She calls herself “Ms.” rather than “Miss” or “Mrs.” That’s weird.” So. Just because she’s a feminist, doesn’t mean she’s gay, went Tom’s silent defense. She could still be straight, but doesn’t want to be defined by her relationships with men; nothing wrong with wanting to be an enigma. The added mystery made Tom want her even more.
Yet, even Tom would admit that Angelina was not a classic beauty. While her figure was nice, there was nothing exceptional about it. She didn’t have an overly shapely rear end or very large breasts. Her face was certainly attractive but not particularly striking. Angelina’s hair was short and dark — not blonde and long like the pinup girls of the day his friends were into, like Cheryl Tiegs and Christie Brinkley. She even wore large-framed glasses that made her look rather owlish.
No, what really appealed to Tom was Angelina’s attitude and footwear. Tom had Ms. Lione to thank for the raging boot fetish he acquired at age 13. Ms. Lione seemed to wear boots nearly every school day. Tom loved winter because he got to see Ms. Lione’s extensive boot rotation — from classic knee-high, high-heeled black, white, tan and brown leather, to high-heeled, knee-high black suede. She had them all and in all the best styles — some even stiletto.
Ms. Lione and her form fitting, sexy boots arrived in Tom’s life at just the right moment: puberty. The timing was perfect — a collision at the intersection of Adolescent Hormones Street and Sexy Object of Desire Avenue.
Out of nowhere one day, the sight of Ms. Lione strutting around the library “innocently” enough in her high-heeled boots suddenly provoked Tom’s first boner. The experience simultaneously scared and excited him. He was too young at the time to know what a fetish was, but old enough to know — and like — the fact that Ms. Lione and her boots aroused him to no end. From that moment on, Tom was head over high heels in love and lust with the sexy librarian and looked for any excuse to pop into the library to see Ms. Lione and no doubt experience his daily woody.
While actresses and fashion models, who wore fashion boots, were everywhere, they were only available on TV or the pages of a magazine. They weren’t real to Tom. Ms. Lione, though, was real. She was actually in his life. Sort of. Even though to her he was probably just another anonymous teenager at school. She was a genuine, in the flesh woman, who wore stylish and sexy boots in his presence. A woman who allowed him to exercise nearly all of his four excitable senses. He could see Ms. Lione and her gorgeous boots up close and get a whiff of her exotic French perfume when she passed by. The only things he couldn’t do were touch the wrinkled leather of Ms. Lione’s booted legs or taste her full, moist and cherry lipstick covered lips. Well, two out of four wasn’t bad.
If boots were sexy to him, Tom determined that they must be to other men, as well, so Ms. Lione had to be making a conscious effort to look sexy for someone or ones — maybe for a man or men at school, for all he knew. Who cared? Just so long as she kept wearing them, escort mamak Tom would be close by in the library at recess angling to get a good look at her. Sometimes, if he was lucky, he’d see Ms. Lione cross her boot-swathed legs, revealing some luscious thigh in the process.
As it turned out, boots weren’t Tom’s only fetish. Around the age of 13 he also discovered he had a thing for women who smoked. Again, Tom was too young to understand the phallic meaning behind smoking, but he had a good idea what it represented and that it sure looked like any woman who would put a forbidden cigarette in her mouth could easily substitute it for an erect penis. Unfortunately, he never saw Ms. Lione smoke, but he was certain she had the habit. A fellow classmate had been in her office once and reported back to some boys — Tom included — that it smelled a little like cigarette smoke.
Ms. Lione had two of the top criterion Tom looked for in a woman: someone who smoked and wore sexy, high-heeled boots. In the late ’70s, Angelina Lione may have been a 40-something year old librarian, but to Tom’s hormone-fueled imagination she was a wild, sexually aggressive woman just waiting to burst out of her shell and fuck him.
Ms. Lione also had an arrogant way about her which Tom liked. She ruled the library with an iron hand, forbidding students from just hanging out there to kill time. She was bitchy, a real diva. Imperious, temperamental and overly dramatic and for reasons he couldn’t understand, Tom was turned on by that behavior.
Ms. Lione was his “first.” The first woman he ever masturbated to and even years later remained his “go-to” woman to stimulate himself to. He’d tried masturbating to other women and even been with a few physically, but always when it came time to ejaculating, the image of Angelina Lione wearing a pair of her sexy boots and seductively bringing a long, white cigarette to her lips appeared in his head and brought him to heights of orgasm that he could never reach with any fictional or real-life partner. To Tom, Ms. Lione was a MILF, long before the term was coined.
All of the preceding had brought Tom to this place at this time. To the threshold of fulfilling a quest born when he was a teen. It was now or never. Tom closed his eyes and silently — almost passive aggressively — wrapped his knuckles on the door. A few seconds later, the door opened. It was Angelina Lione, standing before him looking exactly like he remembered her eight years earlier. And below her plaid skirt, which tastefully matched her form-fitting black sweater, she was even wearing her trademark knee-high, high-heeled black leather boots — although Tom didn’t dare look down at them too long. Around her neck, Ms. Lione wore two necklaces. On her head were the same large eye glasses. Hoop earrings dangled and swayed softly from her lobes. Her makeup was a light, but effective touch, the rouge highlighting her high cheek bones and ruby red lipstick coating her full lips.
“May I help you?” asked Ms. Lione, her tone suggesting that she clearly did not recognize Tom as a former student.
“Yes…ummm…hi, Ms. Lione,” stammered Tom. “I’m…ahhhh…Tom Bailey. I used to attend Riverdale. I graduated in ’79.”
“Okay. Okay. What brings you back?”
“I graduated college a few months ago and a wave of nostalgia came over me and I thought I’d visit and see the old teachers…not like you’re old, Ms. Lione. You’re not.”
“Oh. Would you like to come in? I have a free period between classes.”
Ms. Lione opened the door wider and allowed Tom to enter the library.
“Let’s go to my office and catch up,” said Ms. Lione, sweeping her hand to the right in the direction of her office.
Tom entered Ms. Lione’s office. It didn’t smell like cigarette smoke. Either Ms. Lione quit smoking, he thought, or the rumors were untrue.
“Please, sit down,” Ms. Lione said, motioning to the chair in front of her 6′ long all wooden desk.
Tom took a seat and stole a glimpse of Ms. Lione from the rear as she walked by on the way to her desk. In that brief instant, she seemed a bit curvier and shapelier than he remembered around the waist and firmer in the butt, but maybe that was due to Ms. Lione’s skirt, which looked to be on the tight side.
Ms. Lione sat behind the desk and crossed her booted legs.
Crap, Tom said to himself. That desk is blocking a view of those beautiful boots.
“Well, this is a pleasant surprise,” said Ms. Lione, folding her hands neatly and resting them on her desk, her red-manicured fingernails shimmering from the sun streaming through the window of her office. “It’s not every day one of my ex-students visits. Tell me, Tom, where did you go to school? What did you major in?”
“Well, I graduated from Fairfield in August with a degree in liberal arts,” replied Tom.
“Oh, very good school. What do you plan to do with that degree?”
“That’s sort of the real reason I’m here,” Tom lied. “I’m thinking ofise gelen escort about enrolling in grad school for library science and I wanted to kind of pick your brain about a career in that field.”
The phone on Ms. Lione’s desk rang.
“Excuse me for a second,” she said, picking up the phone with her left hand.
Tom studied the hand — a silver gemstone dress ring wrapped around her middle finger and a sapphire band adorned her pinky, but, thankfully, the critical ring finger of his dream woman was bare.
“Angelina Lione…” the librarian answered into the receiver. “Okay, I’ll be right there.”
“I’m sorry, Tom,” she said, hanging up the phone and rising from her chair. “But there’s an impromptu meeting in the principal’s office.”
Tom was crestfallen. He’d finally worked up the nerve to have an audience with Ms. Lione and she was called away not two minutes into their conversation.
“It’s too bad,” continued Ms. Lione, walking to her office door. “I’d love to hear about those plans of yours.”
Following from behind, Tom was now feet from the exit — feet from walking out of Ms. Lione’s life again; maybe forever. Suddenly, in a rare display of quick thinking under pressure, the shy young man spoke up before it was too late.
“Ah…Ms. Lione, if you’re free tonight, would you like to join me for dinner? We could talk about library science then.”
“Why, that’s a wonderful idea,” exclaimed Ms. Lione. “I’d love to. Do you know Rotini’s in Cromwell?”
“No, but I can find it.”
“Quaint and charming little Italian place. Make a reservation for 6:00, would you?”
“Okay. It’s a date. Meet you there. Gotta run.”
Ms. Lione darted past him — leaving behind the scent of her light, flowery perfume — down three steps — her boots click clacking on the linoleum floor like only boots can — through a set of double doors and was gone before Tom could move. He was virtually paralyzed by his sudden good fortune. She had even said the word “date.”
Wow, could she really be thinking of this as a date date, Tom wondered. Snapping back into reality, he assumed the role of devil’s advocate and figured that could very well have been just her slip of the tongue. After all, as far as she knew, Tom wasn’t there for romantic purposes. This was allegedly just a fact-finding, educational dinner.
Plus, he still didn’t know what Ms. Lione’s relationship status was. She could very well be dating someone already or married — naked ring finger aside. Then again, she agreed to the dinner very quickly, without so much as a moment’s thought. If she had a husband or boyfriend, certainly she’d have to run it by him first, to let him know what her evening plans were, right? Of course, maybe the man in her life was out of town, so there’d be no one to check with.
The possibilities were staggering, as Tom staggered out of the school. Whatever. It was still progress. Sure, dinner could be a bust. Ms. Lione could reveal right off the bat that she was in a committed relationship and then broken-hearted Tom would be stuck, having to listen all evening to her prattle on about library science — or worse yet — the man who he was jealous of; the man who got to make love to Ms. Lione, while he was left to just masturbate to her.
Five hours later, Tom sat nervously at an intimate table for two at Rotini’s. Arriving some 15 minutes early (no way would he risk being late), he ordered a scotch and soda (his first ever) in an attempt to appear more adult than his 22 years.
At 6:00, Tom began checking his wristwatch every 30 seconds, becoming more anxious each time that Ms. Lione had yet to arrive.
Finally, at 6:05:23 she appeared at the entrance to the dining hall. Led to Tom’s table by a waiter, Ms. Lione was dressed in her work clothes — including her intoxicating pair of knee-high, high-heeled, black leather boots. Standing up, Tom immediately walked around to where Ms. Lione would be sitting and pulled out her chair before the waiter had a chance to.
“Chivalry isn’t dead, after all,” said Ms. Lione with a sly smile, as she tucked her hand under the back of her skirt and sat down.
Tom gently eased her chair into the table as the waiter gave him a nasty “that’s my job” look.
“Would the lovely signora care for something from the bar,” the waiter asked in a northern Italian accent, while placing a menu in Ms. Lione’s hand.
“A glass of Chianti please,” said Ms. Lione.
“Sorry I’m late,” she said, turning back to Tom, a moment later when the waiter left them alone.
“That’s okay,” he answered. “I was early. It evens out.”
Ms. Lione smiled and let out a small laugh.
“You’ve been here before, Ms. Lione?” asked Tom.
“Yes, many times,” she said. “I live only a few blocks from here.”
“Oh, really. It’s funny. When you’re a student, it’s hard to imagine teachers having a life outside of school. Going otele gelen escort out to a restaurant seems sort of out of context.”
Tom was hoping to riff off of Ms. Lione’s reply, but her one-word answer left him speechless. Instead, he buried his head in his menu to pick his entrée selection. A minute later, the waiter returned with Ms. Lione’s drink.
“Gratci,” said Ms. Lione.
“Is the signora and her son ready to order?” asked the waiter.
“He’s not my son,” Ms. Lione responded, dabbing at her mouth with a cloth napkin after practically doing a spit take on her wine.
When composure was restored, Ms. Lione and Tom ordered their meals and the waiter retreated to the kitchen.
“What should we drink to?” asked Ms. Lione, raising her glass to toast.
“How about to library science — and every mother’s son?” answered Tom, raising his glass.
“That’s funny. Cheers.”
The two clinked glasses and took sips of their respective drinks.
“Speaking of library science,” Ms. Lione continued, “that’s exciting that you want to make it a career. You don’t find too many men in that field.”
Tom didn’t know how to interpret that remark. Was Ms. Lione insinuating that he might be gay?
“Well, my girlfriend at Fairfield got me interested in it,” he replied, intending to put that thought to rest straight away.
“Girlfriend?! Are you still together?”
“No, we broke up before graduation.”
“I see. If you’re interested in attending Seton Hall for grad school, I could introduce you to the dean of the library science program. We were classmates.”
“Really?! Oh, that’d be great, Ms. Lione. Thank you. That’s very thoughtful of you.”
“My pleasure. So, was your ex-girlfriend the sole reason that sparked your interest in library science?”
“No, I’d been thinking about it ever since I attended Riverdale. I still remember your lessons on card cataloging and the Dewey Decimal system.”
“You don’t say. I didn’t think anyone really paid attention in my classes.”
“I did. I hung on your every word.”
“What a charming thing to say. Thank you. You know, when you’ve taught for as long as I have, sometimes you wonder if you’re really getting through to students.”
“You sure got through to me.”
“To tell you the truth, if it wasn’t for my teacher’s pension, I’d have resigned long ago.”
“And done what?”
“I don’t know. Maybe worked for a county library.”
“I bet you’ve gotten through to more students than you realize. I’m sure a lot return to visit, right?”
“Not me. They seem to visit their math and science teachers, but you’re the first ex-student to visit me in years.”
“That’s their loss, Ms. Lione. You left quite an impression on me.”
“Thank you, Tom. Please, call me Angelina. You’re not a student anymore. You’re a young man. An adult now.”
“Thanks, Ms. Fi…I mean, Angelina. Sorry, you’re about the only former teacher I ever visited who’s treated me like an adult.”
“Maybe it’s that scotch and soda you’ve been nursing,” Angelina said slyly.
A moment later, the pair’s meals arrived. Between bites, Tom proceeded to beat around the bush in a futile attempt to see if Angelina was married or in a committed relationship.
When the two finished their dinners, a busboy came to clean away their plates.
“Would you excuse me for a moment?” asked Angelina, rising from her chair. “I’d like to use the powder room to freshen up.”
“Certainly, Angelina,” said Tom, rising from his chair in gentlemanly fashion.
Permission granted, Angelina picked up her purse, turned on her booted heel and walked to the women’s room. Tom took in the view from behind of Angelina’s shapely ass pressing tightly as she walked against the fabric of her skirt and fine high-heeled leather boots glistening in the low light of the restaurant until his dinner date turned right to the women’s room.
She even talks sophisticated and elegantly…powder room, Tom said to himself. The fact that she said she wants to freshen up I think is a good sign that she thinks this is an actual date, I think. Shows Angelina pays attention to her appearance and wants to look good for me. She wouldn’t put it like that if she had a man at home or was in a relationship, right?
A few minutes later, a fresh coat of cherry red lipstick applied to her voluptuous lips and another layer of mascara lightly brushed to her cheeks, Angelina returned to the table and sat down.
“You freshen up very nicely, Angelina,” Tom said, standing up to push Angelina’s chair in for her. “Not like you didn’t look fresh before. I don’t mean you’re fresh, I…ummm…”
“I think I know what you mean,” said Angelina with a reassuring smile to her flustered date as she settled back into her seat.
“Do you mind if I smoke,” she asked Tom, looking at him while reaching into her purse.
Those six words uttered by his dream woman, confirming his long-standing suspicions, were enough to immediately stir Tom’s loins.
“Um…no. Go right ahead,” Tom said, as he tried to keep his cool.
Sweat began to form on his forehead, while Tom placed his napkin back down over his lap. Thank God, he thought, that I don’t have to stand up for awhile. That would be embarrassing.
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