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, 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."
"Thank you."
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 about enrolling in grad school for library science and I wanted to kind of pick your brain about a career in that field."
"That's wonderful!"
The phone on Ms. Lione's desk rang.
"Excuse me for a second," she said, picking up the phone with her left hand.
