Chapter 5: Lessons

The next day, Lily made sure to arrive at school a few minutes early. The vibrator and lube were tucked away in her backpack, along with an extra pair of panties. She was afraid that she would end up soaking the pair she was wearing and wanted to have a change ready at hand. She slipped into the girl’s room before going to her homeroom.

She nervously checked to see if anyone else was in the bathroom, but she was alone. She went into a stall and double checked that the door closed and latched. She had thought to wear a skirt and pulled her panties partly down. Then she applied lube to the vibrator and slipped the long end into her pussy. It felt good, like a penis, only smaller than Trip’s. The shorter end nestled snugly against her clit. She twisted her hips, and the vibrator stayed in place. It didn’t seem like it was going to fall out, especially once she pulled up her panties, which she did. Then she exited the stall and washed the excess lube off her hands.

The vibrator moved inside her and rubbed against her clit as she walked to class. That was very pleasant, but she knew that if she had to walk a long way it would make her cum. Fortunately, it was a short walk to Ms. James’s classroom.

Lily entered the room. Ms. James wasn’t there yet. She took her usual seat next to Alex, who smiled at her in greeting. Lily was worried that the other students might notice she was walking funny or otherwise acting strange, but Alex didn’t seem to think anything was amiss.

Alex leaned over and whispered, “Can you come over after school today? I’ve missed you, and we could have some fun.”

“I can’t. Ms. James is making me take extra lessons as punishment for not paying attention in class.

Alex made a face of disgust. “She gave you detention? The bitch! When do you get out. Maybe Trip could give you a ride after his football practice. Then the three of us could play.”

“No, I have to go to her house.”

“Really!” Alex’s eyes widened.

At that point Ms. James entered the room and quickly took attendance. Then the first period bell rang. Ms. James unpacked her bag, placing her books on her desk. Then she pulled out her phone and, looking directly at Lily, put it on the desk in front of her.

The class was reading The Great Gatsby, and Ms. James asked Laura Hogan to read a section. As the girl was reading, Ms. James touched her phone, and Lily felt the vibrator inside her start to hum. It was nice but not distracting. Laura finished reading and Ms. James asked the class about the character of Mr. Wolfsheim and antisemitism. She touched her phone again, and the vibrations intensified. Lily found it difficult to concentrate.

Then Ms. James asked Lily to read a section. She found the page and started reading.

“Over the great bridge, with the sunlight through the girders making a constant flicker upon the moving cars, with the city rising up across the river in white heaps and sugar lumps all built with a wish out of non-olfactory money.”

Ms. James touched the phone again, and the vibrations increased. It was all Lily could do to speak the words on the page without stumbling.

“The city ... ahh ... seen from the Queensboro Bridge is always the city seen for the first time, in its first ... ahh ... wild promise of all the mystery and the beauty in the world.”

The vibrator insider her throbbed, but it was the buzzing against her clit that was driving her wild. Lily could feel her orgasm start to build.

Lily continued, “A dead man passed us in a hearse heaped with blooms.” Lily lost her place on the page, then found it again. She continued, “followed by two carriages with drawn blinds and by more cheerful carriages for friends ... mmm ... The friends looked out at us with the tragic eyes and short upper lips of south-eastern Europe, and I was glad that the sight of Gatsby’s splendid car was included in their somber holiday.”

Lily had to pause and breathe deep. The combination of the throbbing deep inside her and the faster buzzing on her clit was becoming too much. She had to suppress a moan before continuing, “as we crossed Blackwell’s Island a limousine passed us, driven by a white chauffeur, in which sat three modish Negroes, two bucks and a girl. I laughed aloud as the yolks of their eyeballs rolled toward us in haughty rivalry.”

Lily was at the point of inevitability. She looked desperately at Ms. James, who nodded at her to continue. Neither her teacher nor the machine inside her showed any mercy.

“‘Anything can happen now that we’ve slid over this bridge,’ I thought; ‘anything at all... ‘ Even Gatsby could happen, without any particular wonder.”

“Thank you, Lily,” said Ms. James as the building orgasm slid Lily over the falls.

Lily closed her eyes and bit her lip, suppressing another moan, as she shuddered in her seat, oblivious to the question Ms. James was asking about race in the novel. She didn’t see Ms. James touch her phone again, but she felt the vibrations decrease back to their original level.

When Lily was able to notice her surroundings, she saw that Alex was looking at her.

“Are you okay?” Alex whispered.

Lily quickly glanced around. None of the other students seemed to have noticed anything. She nodded yes to Alex’s question.

“I’ve seen that look before,” whispered Alex. “It looked like you were cumming.”

“I’m fine. It’s nothing.”

More students read from the book and there were more questions. Throughout the vibrator continued its low throbbing and buzzing, bringing Lily to three more orgasms before the bell rang and Ms. James touched her phone again, turning the vibrator off.

Lily quickly packed her things and scurried off to the bathroom. Once in a stall, she removed her panties, which were, as she had expected, soaked, and slipped the vibrator out of her pussy and into her backpack. She put on the clean pair of panties and exited the stall. Alex was standing there.

“Are you okay?”

“I’m fine,” said Lily as she tried to exit the bathroom.

Alex grabbed her arm, preventing her from leaving. “I don’t think you’re okay. There’s something up with you.” Then in a whisper, “Were you cumming in Ms. James’s class?”

Lily looked around. There were no other girls in the bathroom. Then she opened up her backpack and showed Alex the vibrator.

“Ms. James made me wear this. She controlled it with an app on the phone.”

Alex’s eyes grew wide. “Get out! No way!”

Lily nodded.

“We’re going to be late for our next class,” said Alex. “Tell me more at lunch.”

But it was raining at lunchtime, and they couldn’t go outside to talk. And the cafeteria was too crowded to have a private conversation. So the school day ended before Lily could tell Alex anything more.

Lily’s mother dropped her off at Ms. James’s house again promptly at four. Lily rang the bell, and Ms. James ushered her inside. The teacher was again wearing the leather bustier, fishnet stockings and garters, and stiletto heels. She wore no panties, and Lily could see the orchid leaves of her inner labia emerging from her pussy.

“I’m disappointed with you, missy,” said the teacher.

Lily was confused. “I did what you told. I wore the vibrator. I don’t think anyone noticed.”

“Don’t contradict me!”

“Yes, mistress,” said Lily, remembering finally how to address her.

“Alex Carter noticed. And even worse, you told her about it afterward. Not only could you not control yourself, you disobeyed me.”

“I’m sorry, mistress.” How did she know what she had told Alex?

“You’ll have to be disciplined if you want our training to continue. Do you want me to discipline you? Or do you want to study The Great Gatsby? It’s your choice.

Lily gulped and hesitated. She feared what the teacher meant by “discipline,” but something deep within her psyche wanted it.

Finally, Lily heard herself saying, “Discipline, please, mistress.”

“Good. Now strip.”

Lily undressed once again under the watchful eye of her teacher. Having done it the day before made it no less unnerving to be stared at while getting naked. She carefully folded her clothes, placing them on a chair in the entrance hallway, correctly divining that this was what the teacher wanted her to do. Then she stood naked before Ms. James, covering her breasts with her right arm and her pussy with her left hand.

“Hands at you side!” snapped Ms. James.

Lily dropped her arms to her sides, ceasing the pretense of covering up.

“You can’t hide anything from me. Now follow me.”

She led Lily back into the “playroom.” Then she turned to Lily and said, “Do you remember your safe word?”

“Pineapple, mistress.”

“Very good. Do you remember mine?”

Lily panicked for a moment, straining her mind to remember. After what seemed like an eternity, but that couldn’t have been all that long, she remembered.

“Bicycle, ma’am ... I mean mistress.”

“Excellent. Evidently, you’re not a hopeless case. But you’ll still need to be disciplined for your disobedience this morning. Bend over the exam table, feet on the floor.”

Lily walked over to the table in the middle of the room and bent over, as she had been told.

Ms. James followed her, and placed her wrist and ankles in leather cuffs, holding them in place, legs spread apart. Then she went over to the peg board and selected a rather large strap-on dildo. To Lily it looked about eight inches long and was as thick as her wrist. She watched wide-eyed as the teacher stood in front of her and strapped it on. Then she went back to peg board and selected a riding crop. Lily’s eyes went even wider.

“I think twelve strokes should do, at least to start,” Ms. James said as she walked behind her, disappearing from Lily’s view.

The wait seemed eternal, then suddenly Lily felt the crack of the riding crop on her ass. It hurt, but Lily was surprised to feel a contraction, a mini orgasm. Then another, this time on the other cheek. Lily let out a yelp, this time, partly out of pain, partly out of pleasure. Then ten more blows, and ten more moans. Each one making her more excited and bringing her closer to a full orgasm. Then just as the thirteenth would have pushed her over the falls, they stopped.

There was a long pause, and Lily could not see what was happening. Then she felt her Ms. James spreading her ass cheeks apart and pressure on her asshole. She wasn’t trying to fit that monster dick into her ass?! No, it was something smaller that was pushing her rosebud open. Then her sphincter snapped closed around it. It was a butt plug. Then she felt the strap-on push through her labia into her vagina. It was big, but to her surprise she accommodated it without difficulty.

The teacher started thrusting in and out of her student’s pussy. Lily reveled in the feeling of being filled by the large silicone cock. Exciting her almost as much was the skin-to-skin contact, the feel of the older woman’s thighs slapping against her own and of Ms. James’s hands gripping her waist. But what was truly driving her to orgasm was the feeling of helplessness, the struggle against the leather restraints with each thrust, her inability to escape her situation, and being at the mercy of the older woman.

It wasn’t long before the teen was bucking against her teacher’s thrusts in the throes of an orgasm.

Lily went limp, and Ms. James slowly withdrew the strap-on from the girl’s pussy. Then, before she was fully recovered, the teacher unfastened the cuffs from the bench, and grasping her hair by the roots, she dragged Lily on the floor.

“Kneel,” she told the girl.

“Yes, mistress,” said Lily, complying with the order.

Then Ms. James fastened Lily’s wrist cuffs together behind her back and went over to the peg board once again. She selected another dildo, this time a smaller, but still good-sized, one attached to a gag and a rubber ball. She returned to Lily and strapped the gag to the girl’s face and placed the rubber ball in the girl’s hand. Then she unstrapped the large dildo that she had been wearing.

“You are to face-fuck me.”

Lily tried to say, “yes, mistress,” but because of the gag ended up just nodding her assent.

“Since you can’t speak, instead of a safe word, you will drop the ball if you want me to stop. Nod if you understand.”

Lily nodded again.

Then the teacher straddled the girl’s face, letting the dildo start to penetrate her. Ms. James moaned softly as she slowly slipped down the length of the silicone cock.

Lily watched the older woman’s pussy slide closer and closer to her face, until her nose was buried in the folds surrounding the woman’s clit. The smell was intoxicating, and Lily felt herself becoming wet again.

“Don’t just sit there. Fuck me!”

And with that command Lily started moving her head back and forth, sliding the dildo in and out of the woman’s pussy. As she did so, her movement caused the butt plug that was still inserted in her rectum to move, and that sensation combined with the scent and close-up view of that delicious pussy and the fact that she was still restrained by the cuffs, started her once again on the path to orgasm, this time without her pussy even being touched.

But it was Ms. James who reached orgasm first. Watching the older woman in the throes of ecstasy from such a close-up and subservient angle was unimaginably exciting to the teen, but while all this stimulation brought her to the brink of cumming, the fact that her pussy was untouched kept her from going over the falls.

Finally, Ms. James slipped off the dildo and released the orgasm-deprived teen from her restraints, but she left the butt plug in.

“There are some cleaning supplies in the cabinet,” said the teacher. “Clean up this mess, and put the toys away. I expect this playroom to be spotless and you kneeling on the floor when I return.”

“Yes, mistress.”

The teacher left the room, and Lily silently went about cleaning up the pussy juice and lube that had dripped onto the equipment and the floor. Then she knelt and waited for her mistress to return.

She didn’t have to wait long. Ms. James returned wearing a robe, but to Lily’s shock and surprise, her mother was with her.

“You see, she is quite the good, little sub,” said Ms. James to Lily’s mom. “You were right to think this was the right kind of training for her. She seems to really enjoy it.”

“Did you have fun?” her mother asked Lily.

Lily hesitated, overwhelmed by what was happening, but finally she nodded.

“I expect you want to know what is going on,” her mother said. “But right now, why don’t you go to the bathroom and get cleaned up and then get dressed. I’ll be waiting in the living room. We can talk then.”

Obediently, Lily left the room, thoughts racing through her confused mind. She went to the bathroom. She hesitated over removing the butt plug. She hadn’t been told to, but it seemed like playtime was over. So she slipped it out and washed it. Then not sure what to do with it, she left it on the bathroom counter. Then she stepped into the shower and quickly got herself clean, then dried, and finally dressed.

She found her way to the living room, where her mother was waiting, sitting on the couch. Ms. James wasn’t there.

“Come, sit beside me,” said her mother.

Lily did so and looked timidly at her.

“Just so you know, you’re not in any trouble. I’m not the least bit angry; quite the opposite. I’m happy for you. Your father and I are aware that you’ve been fucking the Carters. And everything that Ms. James has been doing with you has been with our approval.”

Lily was dumbfounded. She heard and understood the words but was having trouble grasping the implications.

“Your father and I,” continued her mother, “are what you might call ‘swingers.’ We have an open marriage and have sex with other people, like the Carters and Ms. James.”

“And the Phillipses?” piped in Lily, who was starting to get her bearings.

“Oh, you know about them? You’re a bit ahead of where I thought you were. But I want you to know that while we have sex with other people, your father and I love each other very much. The extramarital sex enhances our marriage. It makes the sex your father and I have with each other even better. Do you understand?”

“I ... I think so.”

“Well, if you’re not sure, it will become obvious in time. We also want to make sure you learn how to enjoy sex and find out what excites you. Anything you do, so long as it’s consensual and safe, is all right with us. Before I go on, do you have any questions or anything you want to say?”

“I saw you having sex with the Phillipses,” said Lily, getting up the courage to confess.

“Oh, I didn’t mean for you to see that, at least not yet. Did it upset you?”

“A little. I didn’t know what to make of it. But then I started to to ... play with the Carters, and everything started happening all at once.”

“I’m sorry. That must have been really confusing.”

Then the pieces started to fall into place, and Lily asked, “So you and Dad have sex with Ms. James too.”

“I do. But Ms. James is a lesbian. She doesn’t have sex with men.”

“But you’re not a lesbian?”

“No, I’m bisexual. I prefer men, but I enjoy sex with women as well.”

Then Lily made the leap. “Do you have sex with Alex and Trip?”

A surprised look came across her mother’s face. “Yes, we have. Did Alex tell you that?”

“No, I kinda just figured it out just now.”

“Clever girl. Now, I want to know, does the fact that Alex and Trip have sex with their parents weird you out?”

“It is weird, but kind of exciting, I guess.”

“Well, your father and I want you to know that we’re open to having that kind of relationship with you.”

Lily’s eyes went wide again.

“If you’d like to, you’re welcome into our bed. But only if you want to. You don’t have to, and if you’d rather not, we’re not going to love you any less.”