Teacher's Road Trip Pt. 01

Disclaimer -- All characters are 18 or older.

Introduction -- An older straitlaced 48-year-old high school teacher is attracted to a high school student from out of town. She's not a model. She's a 48-year-old woman who looks her age. And she strikes up a relationship with a much younger person. If none of this is your cup of tea, then kindly move on.

Callie started her car and backed out of the driveway. She questioned herself for the one millionth time if she was really sure she wanted to go through with this.

She watched as she passed her neighbor's homes, the familiar trees and driveways lining her path. It was a comfortable typical middle-class suburban neighborhood in Louisville, Kentucky. She had taught high school for the past 25 years and lived in this neighborhood for the past 18. Callie had done everything by the book and as expected. She was always a good girl growing up, listened to her parents and got good grades in school. After high school, she went to college and got a degree in History and Education. She came back to her hometown and her alma mater to teach.

She watched her friends get married off and have families, but her life just didn't work out that way. She'd had some serious relationships and was even engaged once, but things just fell apart, and the marriage never happened. Her parents and friends used to always ask or tease her about getting married and having kids, but after she turned 40, they stopped bugging her about all that. Now she was just resigned to being the old maid in their eyes. Maybe in her own eyes, too.

Now 48, she was single and lived alone, as she had lived her whole adult life. For the most part, she was happy. Friends always remarked how they wished they had her freedom. She wasn't tied down by a husband and kids. She could go out wherever and whenever she wanted. Still, there were times no one was available to go out with her, and that just left her feeling an emptiness.

As her car turned onto the interstate on-ramp, Callie thought about how she had arrived at this point. It was about 6 months ago that Brandon first texted her.

It was obviously a wrong number, and she replied as such. But then they started up a friendly banter. He was friendly and flirtatious, and it all started as harmless fun. It had been a while since Callie had been in a relationship, and the playful conversation reminded her of what was missing in her life. Fun.

Brandon was coy for a long time on specifics about himself. He said he lived in the Nashville suburbs, which was about 2 1/2 hours away from her. She suspected for a while he was married and bored at home. She gave him such a hard time about it that he finally came clean. He was 18 years old and a high school senior.

As a high school teacher, she was used to dealing with the raging hormones from the teenaged boys. Usually it was centered on maintaining classroom order and separating the oversexed boys' minds from the teenaged girls who relished the attention.

Usually, teachers could remain invisible, but there were always a few boys who definitely sent signals and innuendos to their teachers, fishing for any luck. There was a teacher at her school who gave in to the temptation about 5 years ago. She ended up losing everything. She was caught after her nude pictures had circulated amongst all the students. Her reputation was ruined, and she was fired, served a year in jail, and became a registered sex offender.

Back in her 3^rd year of teaching, Callie grew close to one 18-year-old senior, tutoring him after school most days. He made it obvious he was interested in pushing their relationship into forbidden territory, but Callie came to her wits and ended their tutoring sessions.

She still caught the teenaged boys dropping their crass innuendos and double entendres whenever possible. She blew off most of it as harmless bluster with the knowledge that horny teenaged boys were probably desperate enough to sleep with any vagina with a pulse.

Callie couldn't afford to throw away her teaching career and life for a relationship. She decided to keep her distance from the students, although there are always some that become your favorites and you grow closer to.

Every year, it seemed there were one of two boys she taught that became objects of her affection. She could never act on the feeling and risk her career, but she envied any girls that garnered their attention. This year the flight of her fancy was Edward Moore, an 18-year-old senior in her AP US History class. He was sharp and witty, but also a star on the track team. Physically, he was 5'9" and very fit since he ran long distance track events.

Part of her was enamored with the youthful perfection of Edward. He was a young intellectual with a bright future ahead of him. The kind of guy Callie wished she could have dated in high school, but it never worked out for her.

Even now, Callie was still relatively fit herself. She walked regularly, watched what she ate, and had stayed in far better shape than some of the other teachers in the building. She was shorter, about 5'3", but still weighed about 120 pounds, only a little bit more than when she was in high school herself. She knew she was rather plain overall, though. She came off almost like a mousey librarian. Her skin was too pale, and old age was catching up with her. Her shoulder length brown hair was streaked with grey, the wrinkles were becoming impossible to hide, sunspots dotted her arms and shoulders, and her glasses were at least a decade out of fashion.

Realizing that Brandon was in high school stirred all kinds of emotions in Callie, though. She carefully avoided even entertaining any illicit relationships with her students, but Brandon wasn't her student. And he was 18 and legal. And he lived almost 3 hours away. If she visited him, no one would recognize her.

She had initially maintained a text relationship with him because he seemed witty, educated, and kind, all the traits she valued most. Soon her texts with Brandon turned more personal. There were still lighthearted and playful moments, but now they also started opening about their personal details. He revealed he came from a broken home and his dad had effectively been AWOL the past 10 years. She told him about her failed engagement and the loneliness in her life.

Eventually, Brandon asked her for a picture. Sure, why not, she thought. She sent it to him, and he complimented her looks. He's just being kind, she thought. And then she received his photo, and she almost did a double take. Wavy dirty blonde hair, strong nose and chin, high cheekbones, and thin, athletic build. He looked so much like Edward Moore, it scared her.

Now Callie couldn't tell anymore if she was attracted to Brandon or if she projected her infatuation with Edward Moore onto him. Maybe it was both. Either way, she decided to keep in contact with Brandon.

The texts soon became phone calls. And then the phone calls became video chats. Brandon had wanted to start off with video chats, but Callie was still old fashioned and felt more comfortable on the voice phone.

"What does your mom think of all this?" she remembers asking him on their first call.

"Mom thinks I'm basically an adult, so I can do as I please."

"She doesn't know about me, does she? You're afraid to tell her, aren't you?"

"What is there to tell her? Besides, have you told your parents about me?" Brandon playfully teased.

No, no she had not, Callie remembered thinking. Her parents were nearly 80 years old, and she could imagine the news causing them heart attacks and sending them to their deaths.

10 miles to Elizabethtown, the interstate sign read. Callie was making good time on I-65. She was doing just a few MPH above the speed limit, not wanting to get pulled over and have an officer ask her where she's headed in such a hurry. She didn't have a good answer to that question. Not one she wanted to offer, anyway.

As she continued driving, Callie thought back to when their relationship really started to take a turn. It was probably about 3 months ago. At first, Brandon coyly hinted at wanting more. Callie knew what he was getting at. She wasn't that innocent or naive. Her natural instincts told her, enough is enough, end this relationship. But her emotions all told her to keep pursuing it. There was nothing illegal, even if it felt wrong. They were both adults, albeit with an over 30-year age gap. But he made her feel wanted and cured her loneliness.

It became obvious that Brandon was as equally infatuated with knowing she was a teacher as she was with him as a student. He encouraged her to send him pictures of herself. She didn't mind sending him clothed pictures, although she felt silly and awkward posing. But then he encouraged her to show him more and to dress more provocatively in the pictures and during their video calls. He never demanded Callie to do anything, so she didn't mind. Edward was still kind, fun, and supportive. Truth be told, she liked the attention he gave her and enjoyed the newfound naughtiness in their relationship.

Callie had always walked the straight and narrow, and having the chance to be the bad girl excited her. At first, she texted pictures of herself in her bra. Then she let Brandon see her topless on a video chat. She was scared the pictures could somehow make their way back to her students, but she loved having a secret, possibly scandalous, affair. She took comfort that nothing in her actions were illegal. Worst case, maybe some pictures made their way to some folks at her school. It would be embarrassing, but she'd be the victim and hadn't done anything wrong. She was willing to take the chance.

More recently, Brandon had encouraged Callie to embrace her sexuality. Nothing brazen, but he encouraged her to do more to feel sexy. Callie had always worn long skirts and dresses that reached down to her ankles. She added some slightly shorter skirts to her wardrobe. Nothing that would even remotely raise any eyebrows for inappropriateness, but they reached to just below her knees. When she sat down, the skirt rose above her knee and forced her to be conscious not to give anyone a peek under.

All her life, she had worn plain white cotton panties. Not granny underwear, but nothing terribly sexy, either. With Brandon's encouragement, she bought some lacy underwear. Most recently, she had bought some sheer matching bra and panty sets and even a thong. He had suggested she could go commando, but that was still a step too far for her.

The past few weeks in class now, she was hyper aware of how she presented herself to her classes. She occasionally went braless to school. With her smaller B cup breasts and small nipples, it wasn't always obvious, and it seemed to turn on Brandon to know she did this. Truth be told, it turned her on, as well.

Callie also started wearing pantyhose as opposed to the bare legs she'd had all her life. That change she immediately appreciated since she was self-conscious of her pale legs.

In class, she could swear that Edward took notice of the changes and tried to sneak glances at her. As similar as he looked to Brandon, Callie imagined that she was doing all this for Edward. She did little things to innocently tease Edward. She sometimes sat on a high stool in front of class while leading discussions. With the shorter skirts that rose up, she had to be careful not to give a show. But she made sure she was pointed in Edward's direction when there was any possibility of something extra showing. The possible exposure thrilled her, and she'd find herself damp and moist in her nether regions by the end of class.

Not that anyone really noticed. Maybe Edward, but she couldn't be sure he read anything into the extra attention she directed to him. To everyone at school, she was just a doddering old teacher. A wallflower. Background noise in their day they endured before they could return to their teen social lives.

The interstate wasn't very crowded in this stretch of highway. It was littered with mostly truckers since I-65 was a major thoroughfare. Just endless green hills and a good 30-50 miles between towns. Brandon had awoken something in Callie. For years she was almost asexual. Life was just an endless cycle of work and chores. She masturbated infrequently.

More recently, she took pleasure in exploring herself. She bought a vibrator many years ago, but she found that her own hand provided more pleasure than any hard lump of plastic or rubber could. Between her conversations with Brandon and the little bit of daring she did in class, her sexual desires, somewhat dormant, were fully rekindled. Now she fingered herself constantly. Every night, as she lay to sleep, she worked herself to an orgasm. She imagined her lover going down on her. She imagined him entering her with his manhood. Was it Brandon? Was it Edward? She couldn't always be sure. She's not even completely sure it mattered, as long as she achieved her sweet release.

Callie always masturbated on her back, imagining her lover mounting her from on top. Her lover's handsome face smiling down while his cock stood at attention below before sliding into her. She slid her fingers inside and searched for her elusive pleasure zone. Callie was always amazed at how wet she could get. She was glad she had a queen sized bed, even though she was single. The right side had noticeable wet stains from the constant masturbation. The left side she slept on.

Callie even fingered herself at school last week. The first time, she locked her classroom door during her free period. She made sure she was out of sight of the door glass pane. Just the other day, she dared to touch herself while sitting at her desk in front of all her students. She discreetly lowered her hand down while pretending to read a book. The rest of the class was taking a test. Did anyone notice her hiking her skirt up and reaching inside her panties to finger herself.

The desk had drawers on the sides and a privacy shield in front, but the feel of the air against her exposed vagina while she sat in plain view of all her students was the most daring thing she had ever done in her life. She quickly fixed her dress and lifted her right hand back on top of the desk as Edward came up to ask about one of the test questions. Did he suspect anything? Did he notice why her right fingers appeared wetted? She hoped he didn't. Or did she?

There were no cars close to her on the interstate. She lifted her dress and revealed the thong underwear she wore. Her hand slipped inside as she slid down slightly on her seat. She turned on the cruise control so she could play more freely. After a while, she came up on an 18-wheeler. She moved into the left lane to pass him. She started to fix her dress and then thought better of it. She was feeling good and didn't want to lose that feeling. She'd heard that women occasionally flashed truckers on the open interstate. She didn't know any truckers and would never see this trucker again. He probably wouldn't notice anyway.

Callie decided to keep her dress hiked up. The road was fairly straight, and she raised her legs up on either side of the wheel. She steered with one hand while the other went back to work on her mound as she pulled alongside the blue cab. Did he notice? With her in the driver's seat and to the trucker's left, probably not. She couldn't see him, so how could he see her? Still, she'd never attempted anything this daring, this public in her life. She continued fingering herself as she slid past the semi and moved back into the right lane. A few minutes later she climaxed, the scent of her arousal noticeable in the small cabin of her car.

A short while later, the hills of Appalachia were giving way to the outer suburbs of Nashville. The same strip malls, Wal-marts, and big box stores that served as the modern hallmark of suburbia slowly inhabited the landscape.

How did it come to this, Callie wondered? What had she become? A few months ago, she'd have thought it crazy if anyone told her the turns her life took since then. Yet, here she was, simultaneously thrilled and terrified.

How well did she really know Brandon? No one knew her plans to visit him. What if he was dangerous? Yet, she trusted him. She knew he was a good person, that he wouldn't hurt her.

Most recently, he had suggested they finally meet up. Callie had reservations, but her own heathen desires quickly overwhelmed her trepidations. Callie had been slowly putting herself more and more out there, becoming more and more daring. It reinvigorated her, made her feel young again. She was having fun and felt better about herself than she had in a long time. She also recognized that the pleasures from the risk taking could become rote, and sometimes you had to up the stakes to keep that high, almost like an addict.

Brandon had been good to her. He helped Callie explore her more sensual side without forcing her, and she appreciated that. She was ready to take the next step in their relationship.

Brandon offered to visit her, but Callie feared being recognized by someone, even if they didn't meet at her house. She had lived in Louisville for so long, she constantly ran into old colleagues, students, and friends when she was out and about.

Then Brandon mentioned that his mother would be out of town to visit relatives down south for the upcoming weekend. Soon Callie made reservations at a motel, and Brandon would come stay with her.

But how foolish was she? Who was she kidding? She was an old maid. Was she just an easy mark that he would discard as he gained confidence and experience in the world? She knew that was a very real possibility, and yet, Callie was perfectly comfortable with wherever their relationship led. There was trust and companionship between them. Was it love? Probably not. Callie was a realist. The odds of their relationship lasting were slim to none.

Callie worried they would meet in real life, and he would be disappointed. They'd spent so much time texting, talking and chatting but never meeting face to face. To some extent, Brandon was a fantasy to her, and she recognized that. She also recognized that she was a fantasy to him. But what happens when the fantasy becomes reality?

When the thrill of bedding a teacher wore off, would he just see her for the aging, pale, saggy woman she was? She herself was excited to taste the forbidden fruit of sleeping with a student. But would he just become another immature and impatient teen after the initial thrill? It didn't matter, Callie decided. She'd throw all caution to the wind. Callie had always been the good girl. The cautious and safe one who didn't take risks. She didn't date the bad boys. She always did what was expected of her. And where did it get her? It left her lonely and forlorn. For once in her life, she decided, she would live in the moment.

She sucked in a deep breath as she finally exited the interstate and her destination came into view. The Starlight Motel. This is it, she told herself, as she pulled into the parking lot. Here goes nothing.