My Teacher Ms. Miller Ch. 03

Story Info
Tony takes his teacher to prom. They play dressup.
4.5k words
4.63
103.7k
93

Part 3 of the 7 part series

Updated 10/24/2022
Created 12/13/2012
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Tony kept replaying the incidents from the past few weeks in his mind. He was deep in thought.

Tony had returned to school, and Ms. Miller remained his calculus teacher. Ms. Miller seemed to treat Tony like any other student. Tony worked hard during class and did his homework, knowing that dips in his grades might negatively affect their relationship.

She was now regularly wearing normal, professional clothes to class rather than the shapeless bags she had frequently worn before. Ms. Miller had replaced her thick, coke bottle glasses with more stylish ones with black plastic rims. She wore them only when reading.

After five days that felt like an eternity, Tony lingered after class on Friday and asked if Ms. Miller wanted to study together again over the weekend. Although he had tried not to think about his gorgeous teacher, his mind kept straying back to their previous couple of encounters.

To his delight, Ms. Miller agreed with a smile.

When he went over the next afternoon, Ms. Miller was wearing a sexy white tank top with a pair of tight jeans. The black straps of her bra were clearly visible. They were lacy.

After they had studied for an hour, Ms. Miller brushed against him, making his pulse race. Then she went back to her books. When they took a mini study break, Ms. Miller leaned her head against his shoulder. He could smell the flowery scent of her shampoo.

At one point, Ms. Miller went to get a diet soda. She drank it out of a tall glass with ice cubes. Tony tried not to stare, but couldn't help noticing the condensation on the glass as it dripped off her cup and fell on the shelf of her breasts, creating a dark spot.

When she put the cup down, Tony leaned over to try to kiss her. Ms. Miller smiled and pulled away. And that was that.

As he left, she gave him a kiss on the cheek and rubbed her hand across his hair and past his ear. Then she closed the door.

After another week of school, they agreed to meet in Ms. Miller's apartment again.

She greeted him wearing a black t-shirt with a sequiny logo painted across the front. She wore a pair of fitted khaki pants that cut off at the calf.

Looking back, it seemed to him like she was flirting with him. They sat closely together at the kitchen table in her cramped apartment. She would laugh at his jokes. She would brush against him when she stretched.

Through it all, she would steadfastly refuse his attempts to push the relationship forward. When he initiated light physical contact, like putting his arm around her waist, she accepted it.

When he tried something more serious, she refused. As he was giving her a shoulder massage, he brushed his lips against her neck. She laughed and leaned forward away from him. She was never offended, but they didn't get beyond a few light touches.

At the end of their second study date, Tony tried to ask Ms. Miller as calmly as he could, "Ms. Miller? Am I doing something wrong?"

"What makes you say that, Tony?" she replied calmly.

"Well, I thought we had something special going, but every time I try to take us a little bit further... you don't seem to like it."

There was a long pause. Ms. Miller's blue eyes looked at him closely, and held his gaze. Finally, Tony blinked, and then looked away.

"I'll give you a hint, Tony. You'll have to try harder than that to win me."

That brought Tony back to the present. What could Ms. Miller mean? How could he try harder? What would it be like to win her?

The first time he had met her was in the park. He had "discovered" that his mousy teacher was actually incredibly hot. He had gone over to her apartment, and, at her request, he had felt her body all over. She had given him a blowjob.

The second time was during a study date, much like the ones they had just done. But she had let him watch her change in her bedroom. And they had sat together while both of them were half naked. Finally, he had fucked her tits.

Try harder? How much harder could he try?

Tony couldn't wait any longer. He called up the only person he knew who could give him girl advice. This was his cousin Caitlin.

Caitlin lived about two hours' drive from his parents' house. This meant that their families got together for holidays, but did not regularly hang out.

Caitlin was herself an attractive redhead who seemed to be popular with boys. She had a sister who was older than either of them, who Tony didn't know well. Along with their other cousins, Tony could remember laughing and joking together late at night as their parents hung out in the other room.

Last summer, the conversation had strayed into topics of love, and Tony could remember sharing who he liked with his cousin. He felt extremely comfortable, and Caitlin had always seemed to understand, to empathize with him.

During family get-togethers, even when he got rejected by some girl or another, Caitlin never judged him and never condescended to him.

But this was different. The girl he liked this time, Ms. Miller, was his teacher. Tony didn't think that Caitlin would understand that, and didn't want to endanger his teacher's job.

So he decided carefully what to tell Caitlin, and then dialed her cell phone.

She picked up on the fourth ring.

"What's up, cuz!" Caitlin sounded a little out of breath.

"Are you alright? Can you talk now?" Tony said.

"Sure sure. I just had to step outside. What's up?"

"Well, I have a girl problem," Tony said. He explained carefully the story he had concocted, which was basically honest but omitted key details: he had met a girl, and they had begun hanging out. From their first date, they had been hot-and-heavy. They had been together twice and both times it had ended in something physical. Then, on their past few study dates, the girl had refused to even kiss him.

"So you're mad because she won't put out again?" Caitlin laughed.

"It sounds bad I know, but that's not exactly it," Tony replied. "She wants me to 'try harder,' but I don't even know what that means."

"Oh, that's easy," Caitlin said, "It means that she doesn't want to just get together and have sex. You have to wine her, dine her, you know? A little romance, a little fun. Then see where she is."

Tony was immediately struck by how right that sounded. Ms. Miller wasn't a girl that you could just give booty calls to.

But another objection came up for him. He couldn't exactly bring Ms. Miller to the mall, or even out to a casual dinner. Someone might see them and recognize her. And she would lose her job if anyone found out that he was her student.

He thought carefully about what to say next. "Well, this girl. A lot of people around school recognize her. She has a bit of a reputation." That was true, everyone in school did recognize her since she was a teacher.

"Oh, Tony. You don't want to be seen with her? You're just using her for sex?"

"Kind of." That sounded bad, but less bad than admitting that he wanted to fuck his teacher.

There was a pause while Caitlin thought about it.

"I have the solution. You should bring her to the winter formal at my school. It's two hours away and no one will recognize you guys. You can do something fun together and no one will see you guys together."

Tony thought for a minute. That was a great idea, and it was very romantic. To take his teacher to prom, but in an anonymous way would be the perfect way to show her that he cared.

The next evening, Tony knocked on Ms. Miller's door. She opened it, wearing a loose-fitting turquoise tank top and pajama pants with thin, rainbow-colored stripes.

He presented her with a long-stem red rose. "Ms. Miller, would you go to the prom with me?"

Ms. Miller blushed and looked down. Tony thought that she looked absolutely beautiful. "Tony, you know we can't be seen in public."

Tony explained his plan. His cousin had purchased them tickets at the location of the prom, about two hours away. He could pick his teacher up and drive them over. Between her house and the prom location was a nice restaurant that he could bring them to.

His teacher accepted the rose and gave him a big hug. Tony wrapped his arms around her and pulled her in tightly.

"Very nice, Tony. Very nice."

*********************

The days leading up to winter ball came up in a flash.

Tony pulled up to his teacher's house in his beat up sedan.

His teacher was wearing a long blue dress. It was bulky and almost shapeless, and trimmed with a white vertical wavy material. It had pale blue shoulder puffs. The bottom of the dress had a wavy flare at the edge which served to obscure her legs to the mid-calf. She also wore a loose fitting black jacket, which looked wrinkly and beat-up.

Her hair was pinned up in a loose bun, with a few strands doing their best to escape. Her makeup seemed to be deliberately garish. She had dark blue eye shadow covering her upper eyelids, heavy splotches of red rouge, and heavy red lipstick.

In short, Ms. Miller looked like a high school prom date, and not a very attractive one at that.

"I got this out of my closet." What do you think?

Tony lied, "You look really nice."

When Ms. Miller had first started teaching Tony's class, she had worn clothing that concealed her body entirely. Her dress seemed like it was drawn from the same closet.

Tony gave Ms. Miller the flowers he had brought. She had a duffel bag and a purse with her. She threw the duffel bag in the trunk and they started their drive.

*********************

Dinner passed uneventfully, as did the 2-hour drive to the gym where the dance was held.

When they arrived at the dance, Ms. Miller seemed to behaving stiffly. During the dance, she would mostly stick to an awkward version of the dancing of other high school girls. This mostly consisted of shifting side to side.

A slow dance played, and Tony asked Ms. Miller to dance. She was already a couple of inches taller than him, and her high heels made her seem much taller. She put one hand on his shoulder and the other held his. He put one hand on her waist. They circled each other stiffly.

In short order, Tony was bored. He didn't know anybody at this school, so wasn't even able to talk with his friends. His beautiful date was acting like a tremendous stiff. Maybe she didn't know how to dance?

"Tony!" Tony turned and saw his cousin Caitlin. She looked amazing. Caitlin wore a deep green dress which contrasted with her shining red hair. It looked like a gown from some medieval French period, with crisscross straps cinching it tightly around her bust and waist. The dress was cut dramatically at the chest and showed off a deep valley of cleavage. Caitlin's breasts looked like creamy mounds as they threatened to burst out of her dress.

Caitlin squealed and then greeted Tony with a very warm hug. Tony held her awkwardly.

"Oh don't be such a stranger. Give you cousin a kiss!" And she grabbed him and kissed him full on the mouth. Tony could smell the alcohol on her mouth. Apparently Caitlin had been to a little pre-party before coming.

"This must be your date! Hello, I'm Caitlin!"

She grabbed Ms. Miller for a hug and began chatting.

Tony couldn't help but compare Ms. Miller and Caitlin while watching them talk side-by-side. They were both tall. Caitlin was about his height, and Ms. Miller a few inches taller than that. Caitlin seemed to be very animated, gesticulating by waving her hands and arms around. Ms. Miller seemed standoffish. Her arms were folded as she made minimal responses to whatever Caitlin was talking about.

Tony had never noticed before tonight, but Caitlin's breasts were even larger than Ms. Miller's. While Ms. Miller was more athletic, Caitlin was more voluptuous.

Caitlin pulled Tony aside and whispered into his ear. "Tony, she seems really nice! Why wouldn't you want to be seen with her?"

Tony was extremely conscious of looking into Caitlin's cleavage. Trying to keep his eyes locked straight ahead, he shrugged, and then said, "Maybe I'll tell you later." There was no way in hell that he would tell her.

He went back to join Ms. Miller.

"Tony." Her tone was icy.

"Yes?"

"You didn't mention your cousin before."

"I didn't think I had to," Tony was a bit confused.

"This was her idea, right? For you to go to her winter prom? With a girl that you couldn't be with in public?"

"Yes," Tony suddenly felt himself on very thin ice.

"I have to go to the restroom," Ms. Miller said, and stalked away without waiting for him.

Tony waited awkwardly for her outside of the women's restroom. Other guys were waiting for their dates. He didn't know anyone around him. After 15 minutes had passed, Ms. Miller finally emerged.

She looked totally different. Ms. Miller had wiped her old makeup off entirely, made it much more subtle, and it now emphasized her finely sculpted features. She had loosened her blond hair from its tight bun.

She had made dramatic adjustments to her dress. She had taken off the ugly blue shoulder puffs, and left her shoulders and arms bare. She had removed the puffy hem as well. It looked shorter, exposing her knees and a generous tranche of her thighs above her knees. Ms. Miller had made some kind of subtle adjustment near the neck of her dress. Now, it subtly emphasized her chest rather than concealing it.

Tony didn't know what to think. Why had she changed her outfit? Now Ms. Miller looked, well, she looked sexy. Several other boys stopped to look.

"Wow, Ms. Miller, you look great!" Now Tony meant it.

"Let's dance, Tony."

When Tony and Ms. Miller walked back to the dance floor, her attitude had changed as well. Ms. Miller's danced freely, easily, almost sinuously. Her hands were above her head, now they were playing with the locks of her hair, now rubbing her hips. Tony could barely keep up.

He felt incredibly masculine as his beautiful date draped herself all over him. Their faces were close, and he could feel her hot breath against his mouth and his neck.She thrust her leg between legs and they began dancing together aggressively. He could feel her thigh rubbing against his crotch, and was starting to get aroused.

He could tell that others were watching. Some of the guys from the school, even while dancing with their dates, would stop and watch the hot blonde putting on a show. While one thumping beat played, she rubbed her ass into him. He knew that she could feel his erection through his pants, but continued to wantonly rub herself up and down against him.

Out of the corner of his eye, Tony saw a flash of green and red that could only be Caitlin. It disappeared.

Ms. Miller turned back towards him, and smiled. Tony felt uncomfortably like a bird being cornered by a cat. "Let's get out of here," she said.

Tony could only agree.

*********************

On the drive home, Ms. Miller said, "Why don't we turn off here?"

They exited in a well-lit area. Ms. Miller gave him a few directions, and Tony found himself driving up to a Holiday Inn.

Tony's breath quickened as Ms. Miller pulled up to check in. They got a room and went to it. Ms. Miller got the duffle bag out of his trunk, and disappeared into the bathroom.

"Tony? Why don't you relax from your tux?"

Tony hadn't brought a change of clothing. He gratefully kicked off his uncomfortable formal shoes. He undid his bow tie and took off his jacket. He unbuttoned the top few buttons of his white dress shirt, and waited for Ms. Miller to come out.

He didn't know how long he would wait, so he tried to distract himself from what she was doing in the bathroom. He turned on the television and started watching sports highlights on ESPN.

"Tony?" Now Ms. Miller had emerged from the bathroom.

Tony gaped. Ms. Miller was now changed out of her prom dress. She was now wearing a white cheerleader's top that was about three sizes too small for her. It had the words "JHS" in large red letters across the middle. The "H" in the letters was split open by the zipper in the middle of her top. Tony could easily see why the zipper wasn't closed; it appeared to be unable to finish the heroic task of encasing Ms. Miller's overflowing breasts.

She was also wearing a short red pleated skirt. The skirt swished as Ms. Miller walked towards him, swaying her hips slowly and deliberately. Her legs seemed to stretch out on and on under her skirt. Ms. Miller was wearing knee high white socks and no shoes.

To complete her look, Ms. Miller had tied her blond hair into two tight ponytails on the sides of her head. She had again changed her makeup, so that now she had a shiny pink lip gloss.

She looked like a ditzy cheerleader. No, scratch that, a very sexy, very slutty cheerleader, Tony thought.

Tony's mouth went dry. He was never popular enough at Robinson High School to date the cheerleaders. The most he did was admire them as they performed at football games. He would stare at them, hoping to catch glimpses of their underwear as they did they high kicks.

And now Ms. Miller was dressed in a cheerleading uniform. It wasn't a uniform from Robinson, he reflected, but it looked real enough.

"Like, thanks for taking me to prom, for sure," Ms. Miller said, in a cloying, high-pitched voice. She was playing the part of a bubble-headed cheerleader, Tony realized.

Tony tried to play along. "Err, you're welcome, baby." He tried his best to sound like a dumb jock, with extra base and words that didn't quite get every syllable correctly.

"And you are just the hero of our school! Scoring all those touchdowns!" She sat next to him on the bed and put her arm in his. She folded her legs under her. Her short skirt slid up, exposing even more of her delicious thighs.

"Well, baby, it's easy to be a star... when I have the right mobivation." He deliberatively mis-pronounced the word "motivation."

"Mmmm... What motivated you during the game, sugar plum?" She purred at him and leaned her head on his shoulder. Tony could see down her deep cleavage from this perspective. The round upper halves of her breasts were clearly visible.

"Just thinking of you, baby." Tony didn't know how far to take this.

"And what I promised you if you scored a touchdown for me?" She looked up at him with her big blue eyes. Their faces were close.

"Yeah, baby. That's right. You inspired me. When that linebacker was coming at me, ready to sack me, you know what I did? I looked over to my favorite cheerleader... cheerleader Miller, and you motivated me. He hit me, but I was like a wall. Like a fucking stone wall. That's how you make me, babe."

Ms. Miller giggled. "You are like a wall. A fucking stone wall. How did I motivate you?"

"Well, you know, you gave me a sis-boom-bah. And a rah-rah-rah. Yeah. That's what I needed."

Ms. Miller laughed, then said, "Babe, you're not a wall."

"I'm not?"

"No, you're more like a pillar. A big fucking pillar. A pillar that I just love to take in my mouth."

Tony was suddenly at full mast. Hearing dirty words come out of his teacher's mouth excited him intensely.

She continued, "That game you just played was magnificent. Those touchdowns, ooh! They made me so wet. Wet for you."

Her hands began to fumble with the buttons on his shirt. Tony watched silently as she got it open. Tony left the bed and took off his pants. He removed his shirt entirely and lay on the bed, clad only in his boxers.

Ms. Miller climbed on top of him and straddled him, sitting on his stomach lightly. Her pleated skirt draped over his chest.

She ran one lacquered fingernail over his bare chest. She leaned over and kissed him deeply on the mouth. Her lip gloss tasted of strawberries.

Tony wrapped his arms around her neck and pulled her in tightly. She eased down until she was lying on top of him as they were kissing. Her breasts pressed up against his chest. After a few moments, her tongue entered his mouth. She lay on top of him like that, with one of her legs between his.

12