Lipstick & Miniskirts

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Lipstick & Miniskirts Page 7

by John Dylena


  He gets up and runs out the door, leaving me alone on the floor, with cum oozing out of my pussy and asshole and dripping off of my face. I smile the best that I can with these thick, cock-sucking lips and drift off.

  Bimbo. Fuck doll. Whore.

  The words fill my mind, but they grow weaker every second. I can hear the noises of the convention going on outside the door. I can hear people talking and laughing. No one comes in while I’m lying there. The voice in my head grows fainter until it vanishes all together.

  My mind becomes clear again and I groan as I sit up. I try to stand, but I’m too tired and weak. I fall back onto the couch with a grunt. I look down at my body and notice it start to change. Seconds later I’m back to my old self.

  Well, a fragment of my old self.

  I’m a guy once more. The hot pink and purple costume changes back into my graphic T-shirt and shorts, and the boots turn into my regular walking shoes. I’m back in the clothes I wore before this whole thing happened, only I’m thinner, much thinner. The mess is gone too; no trace of any illicit activities happening in this break room.

  I stand up, inspect my body, and let out a sigh of relief when I confirm that I’m back to being a guy. On the ground by the couch I find my backpack, which vanished during the transformation.

  That’s right. That all really happened.

  My gut twists into knots when I recall the events. What I said and did, what I thought. I bend down and pick up my backpack and stop when I find the planet button on the ground underneath my backpack. I pick it up, inspect it, and notice there’s a trashcan by the door.

  What if it makes me transform again? Do I want to experience that again?

  Then I hear the voice again, the soft, honey-sweet voice that tempted me and seduced me.

  You have paid the price for your words, thoughts, and actions. The button is yours to keep. Wear it, and you’ll become Val Quinly once more. Your body and mind will be your own; you won’t be controlled.

  “Unless I want I want to experience that again,” I say aloud.

  Correct. Unless you want to be controlled once more.

  I flick the button into the air and catch it before stuffing it into my backpack and smile as I walk out the door back into the convention.

  I wonder what else that old lady has for sale.

  A PASSING GRADE

  “What do you mean I’m going to fail?! I… I have to pass this class if I want to graduate!” Tyler paced frantically in the front of the classroom. He rubbed his face with his hands as he tried to figure a way out of this hole. A senior in college, he was almost done with his very last semester of school. His college degree in Economics was so close he could taste it.

  He had it all planned out and had worked his butt off in all his classes so that he could coast through the last semester. But even the best laid plans often go astray, and one of his classes this semester had completely caught him off guard.

  Everything else was going smoothly; the other classes he was taking were easy A’s. Needing one more core class, he thought it would be fun to take a psychology class about sex. Not only that, but he’d heard that the teacher was pretty hot. A class about sex with a hot teacher? Who could resist that?

  That hot teacher, Ms. Abby Kilia, turned out to be rather difficult. The reviews for her all said the same thing: “hot, but strict,” and Tyler knew that going in. He figured the reviewers were exaggerating, but the workload for that class made up for the rest of the ones he was taking, and while the material was interesting, it was ultimately Ms. Kilia that kept him coming back to class.

  Smart, cunning, and cold, Ms. Kilia showed no mercy. With a class that talked about sex and the psychology behind it, things could get out of hand fast, especially if the students were all horny coeds and immature frat boys who still laughed at dick jokes. Fortunately, Tyler was neither.

  Two weeks into the semester, half of the class had dropped out. All that remained were the psych majors and other students like Tyler who needed the class to graduate. Unfortunately, the few women left either already had boyfriends, or were too unattractive for him, which left him with little to daydream about during lectures.

  Ms. Kilia was the only hot one left. Her outfits were almost always skirt suits of different colors and styles, and she always wore high heels. When it wasn’t a suit, it was a dress; rarely did she wear pants.

  She had black hair and dark eyes that glimmered behind short, rectangular glasses. When lecturing to the class, she often held the frames in her hands and she’d occasionally bite down on the curl.

  Tyler never really had student-teacher fantasies. Most of the time, his sexual dreams were about slutty sorority girls, or the quiet nerdy girls with a secret wild side. It wasn’t until he stepped into Ms. Kilia’s classroom on the first day of the semester that he found himself fantasizing about visiting her during her office hours for some “one on one” time.

  He figured that the combination of a body like hers—incredibly sexy for a woman who was probably forty—plus all the knowledge she had about sex would make her a very competent and skilled lover. Not to mention that she wore no wedding ring, which meant she was fair game.

  Throughout the semester, Tyler tried to get to know her better, hoping to get on her nice list and score a date, and hopefully some amazing sex, too. But as the weeks went by, he found that just wanted to pass the damn class, which at the moment, wasn’t looking all that good.

  Crumpled up in his hand was his graded essay, marked up with plenty of red ink and the terrifying letter “D” circled at the top. Tyler’s heart had sank when she’d handed it back to him in class earlier. But he wasn’t the only one; several others scored pretty low, but for every D and F, there was also an A and B. There were a couple other seniors in the class alongside Tyler, but he was the only one that was on the verge of failing.

  Ms. Kilia watched him as he paced back and forth. She sat on her old school wooden desk, her legs crossed and her hands resting on the edge. She leaned forward and patiently waited for him to calm down, occasionally checking her nails or adjusting her seated position. “I’m sorry, Tyler, but there is nothing I can do. Study hard for the final.”

  He stopped pacing and set his essay on the desk behind him. “I have to get above a 95% if I even want to pass this class.”

  “Like I said, Tyler, study and you’ll do fine.” She looked at him from behind her shiny black frames. Her voice was calm and collected; professional and apathetic. He would find no solace from her.

  “Ms. Kilia, is there some way I can make this up?” he whimpered. “I’ll do anything.”

  She hesitated. Normally, she’d reply right away with a cold, hard no. Tyler was not the first to come begging for extra credit or leniency, and he wouldn’t be the last, either. But she was feeling strangely accommodating today, and Tyler was different from the rest of her students.

  Everyone else just came and went without a single hello or goodbye. It was just business with her students. But Tyler was so much more capable than they were, and she knew that he wasn’t trying hard enough. He needed motivation; a push. She thought about it for a second more, but ultimately, she shook the thought away.

  She knew that he was attracted to her, and that complicated things. He wasn’t the first. In the years she’d been teaching there, she’d had male—and female—students straight up ask her out. Abby always reminded them that she was their teacher, and if they brought it up again, she would report the student.

  Tyler was different. She would notice him staring at her, his eyes not on her chest or face, but on other parts of her body. At times, she’d catch him staring at her heels and legs. He was shy and timid in her class, never raising his hand to answer a question. He’d only say something if he was called on.

  “Sorry, Tyler, but it wouldn’t be fair to offer extra credit to you and not to the rest of the class. But like I said, you can still pass. You just have to study.” Ms. Kilia slid down from the desk and stood in
front of him. With her high heels on, she was just a tiny bit taller than him.

  Tyler hung his head. His shoulders slumped. “Okay, I’ll try.”

  “Don’t just try to work harder,” Ms. Kilia said. “Actually work harder. I know you have it in you.”

  Tyler said nothing as he slowly walked out of her classroom, dragging his feet. Ms. Kilia watched him go.

  If Tyler really wants to pass this class, he’ll have to study extra hard, she thought, her lips curling into an evil grin as she packed away her notes. His offer to do anything in order to pass remained on her mind, and the following week, she decided to take him up on it.

  “Tyler, would you mind hanging around for just a few minutes?”

  Tyler remained by his desk while the rest of the class shuffled out of the door. It was the Friday before a long holiday weekend, and about half of the class had decided to skip in order to get an early start. He was one of the few that remained. Even though there was nothing he could do to save his grade, he figured it would still be a good idea to stay on Ms. Kilia’s good side.

  She stood behind her desk and waited until they were alone. Even after the last student left, she remained quiet for another minute or two.

  “Did you need me for something?” he asked, looking around suspiciously.

  “Last week, you asked me if there was something you can do to help with your grade. Well, there is something, but it will require some effort on your part.”

  Tyler’s face lit up and he smiled from ear to ear. For all he knew, she could be offering him the best sex of his life, but that didn’t matter. At that moment, all that he cared about was not failing, and he hadn’t been looking forward to spending hours every day studying.

  “Come to my office tomorrow morning at seven-a.m. sharp,” she told him, narrowing her eyes. “Tardiness will only harm your chances.”

  The smile and the glow on Tyler’s face vanished, and she added: “You don’t have to come if you don’t want to, but you’re the first person I’ve ever offered this chance.”

  “No, no,” he said quickly. “I’m sorry, Ms. Kilia. I’ll be there. I promise.”

  “Seven-a.m. sharp!” she reminded him.

  “Understood.” He smiled a fake smile as he grabbed his backpack and walked out the door.

  “Don’t fail me, Tyler,” she said to herself once she was sure he was gone.

  This place is creepy when it’s empty, Tyler thought, yawning as he stood on the top floor of the school. He looked down at the lobby below him. The building was long and rectangular with a wide, open middle. Plants grew out of pots on the bottom floor, and the early morning, sun beamed in through the skylights that covered the rooftop.

  In the four years he’d been attending this university, he’d been in this building many times. Even on the weekends, there’d usually be people here, but on this extended weekend, it was entirely empty.

  The quiet was unnerving. He expected to see a security guard patrolling, or even a janitor, but there was nobody except him.

  The sunlight gave way to blinding fluorescent lights as Tyler left the atrium and entered one of the hallways. Most of the classrooms had doors that opened to the atrium, but all the offices had to be accessed from one of the passageways.

  He walked down the long, narrow hallway that ran parallel to the atrium until he arrived at the psychology department. All the offices were cluttered together, their doors facing a large, open room with couches, tables, and desks.

  The only office with a light on was Ms. Kilia’s. Clenching his backpack, Tyler walked up to her door and raised his fist to knock on the wood, but Ms. Kilia opened the door before he even had the chance.

  “You’re late,” she said. Tyler looked away from her to the large clock mounted on the wall, then at the watch that he wore. The clock on the wall said it was a few minutes past seven, while his watch said it was seven-a.m. exactly.

  “Guess my watch is slow.” He forced a laugh, hoping to lighten the mood. Ms. Kilia stared at him, unamused.

  “Come with me,” she said, walking past him. He opened his mouth to speak, but his attention turned to the small suitcase that wheeled behind her. “Hurry up!” she called over her shoulder, sensing his hesitation.

  “Yes, ma’am!”

  He followed her down the labyrinthine hallways until they arrived at a small, secluded classroom located deep within the bowels of the building. I could probably find a doorway to Narnia in this place, he thought as he watched her unlock the door.

  The classroom was small and square with five rows of six desks. At the far end was a rectangular wooden desk, and in the corner, there was a desktop computer hooked up to the room’s projector. The whiteboard on the wall was pristine and Tyler noticed a thin layer of dust on the smooth desk surfaces.

  Ms. Kilia said nothing as she walked down one of the aisles with her suitcase in tow. The walk from her office to this classroom was short, maybe a couple of minutes, and the entire time, he’d wondered what was in her suitcase. Normally she carried a large designer bag where she kept her laptop, book, and notes, among other things.

  When he left her classroom the previous day, his mind went over all the possibilities of what was in store for him. He figured it was going to be a private study session, but lingering in the back of his mind was the belief, and the hope, that the tutoring would get rather… intimate.

  He thought there might be some validity to this possibility when he arrived at her office earlier. She’d greeted him wearing a long black coat pulled tight across her body. Other than the coat, she wore dark stockings and black patent stiletto heels. She moved so gracefully in them it was like she was defying gravity.

  Ms. Kilia left her suitcase by the desk at the far end of the room. Then she walked up to Tyler and sat on the desk in front of him.

  “You said last week that you’d do anything for the chance to raise your grade, correct?”

  “Yes, ma’am.”

  “Are you still willing to do anything?”

  Tyler hesitated, his words stuck in his throat.

  “Tyler?” Ms. Kilia prompted him. “This is your last chance.”

  Last chance for what? he wondered, though he answered anyway.

  “…yes, I am.”

  “Good.” She climbed down from the desk and walked to the door. He watched her poke her head out and look around. His eyes went wide when he saw her close and lock the door. Oh god, what did I get myself into?

  She winked at him as she walked past and to the metal computer desk in the corner. After searching through a couple of the drawers, she pulled the cap off of the dry erase marker, inspected the tip, and then walked up to the whiteboard.

  Tyler’s jaw hung slack as he watched her write the word “detention” in big capital letters on the whiteboard. He nearly died when she turned toward him after writing the word and removed her thick coat. His mouth dried up and he stared at her.

  Ms. Abby Kilia stood behind the desk wearing a tight white blouse, gray miniskirt, black stockings, and high heels. Tyler could see the tops of her stockings and the garters that held them up. Her white blouse had the top buttons removed and her cleavage was in full view.

  Tyler found himself in a real life student-teacher themed porno.

  He remained seated in the desk, as standing up would’ve revealed the massive boner in his jeans. His dick pressed hard against the fabric of his pants and threatened to burst through the denim. It throbbed when she spoke.

  “Tyler, you’ve been a bad girl, and you need to be punished.”

  He was so entranced by her beauty that he only caught on to the last part of what she said. Tyler fidgeted in his desk as she sashayed toward him. Ms. Kilia played with the buttons on her blouse as she stood next to him. She bent down and placed her hands on his desk as she inched closer and closer to his face, her lips puckered and moist.

  He lifted his head toward her as he slowly lined up to kiss her. Tyler closed his eyes as she moved within inche
s of his face, only her lips never touched his. He opened his eyes to see her lingering, taunting him with her beautiful red lips. His heart pounded in his chest and he whimpered quietly as she moved away from him back to the large desk at the front of the classroom.

  She picked up the suitcase and set it on the desk. He heard the zipper open and he watched her remove the contents. Tyler went pale when he saw what she brought with her to “detention.” He saw a pink plaid miniskirt, a white button down blouse, white lace panties and a matching bra, a pair of shiny, pink patent Mary Jane high heels, white stockings, a brunette wig, and a makeup kit.

  He sunk lower in his desk as she continued removing items. There was a strap-on, double-ended dildo with harness, an inflatable butt plug, a pink leather collar, a riding crop, and finally, a clear plastic chastity cage.

  The raging boner he had seconds ago vanished. He looked back at the door and considered making a break for it.

  “If you leave now, I’ll fail you,” she said, catching his furtive glance. “But if you stay and play along, you might just get an A.” Ms. Kilia walked around to the front of the desk and sat up on it. She crossed her legs and looked down at him. “You told me you’d do anything.”

  “I… I…” Tyler’s heart raced and beads of sweat formed on his brow. He bit his index finger as he went back and forth in his mind. She said nothing, only smirking as she waited patiently for him to decide.

  Either I fail and don’t get to graduate, thus losing the amazing job waiting for me, or I endure a couple of hours of sexual humiliation and I get an A.

  Over the long winter break, a family friend told Tyler that there would be a job waiting for him once he graduated. All he needed was degree, and he would have a solid career right out of college.

  Not many get that opportunity…

  He hung his head low and grumbled a reply.

  “Louder.”

  “I… I’ll do it.”

  It took all his willpower to say the words, and once they left his mouth, he wanted to grab them and stuff them back in. She got off the desk and walked up to him, holding the pick collar in her hands.

 

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