Teaching New Tricks

Sorry for the earlier upload, that was a rough-draft. I accidentally copied it here from the docx file. This one is the right one.

It had been another strange but exhilarating day at school for Kyle. The new roles assigned by the app had started to feel almost natural. A morning fuck with Britney, holding her hair in a fist, pushing her face against the bathroom board, while railing her from behind was a great way to start the day. Figuring out new ways to fuck Brad up was a bit challenging, but Kyle got an idea.

"Okay, I am almost there!" Kyle pulled out of cheerleader's wet pussy with a gasp, her juices coating his cock. He grabbed it and started jerking off getting himself to orgasm.

"Common, leave my boyfriend a present!" Britney's open mouth and taunting eyes were all the motivation Kyle needed. He stroked his cock faster, feeling his balls tighten. With one final thrust, he erupted, filling her mouth with hot, sticky cum.

Her eyes sparkled with mischief as she smeared his cum on her teeth and lips. "Thanks," she gurgled, standing up and fixing her skirt.

"Master? Are you okay?" Cory's voice was a soft, worried whisper from outside the bathroom door. She had been waiting for what felt like an eternity, her own arousal building with every muffled moan and slap of skin against skin that she heard from within.

The door swung open, and Britney emerged, her cheerleader top slightly askew, her full lips glistening with something other than sweat. She smirked at Cory, her eyes sparkling with mischief. Before Cory could react, Britney grabbed her by the face, and bent her down to cover her lips.

"Mmmmmm," Cory struggled for a second before letting Britney's tongue into her mouth, the taste of her master's cum coating her own tongue. Gulp-gulp-gulp. She swallowed, the taste of him mixing with hers. "Master's... cum," she murmured when Britney pulled away, her eyes wide with shock and arousal.

"Th-than you," Cory stuttered, her cheeks a fiery red, her eyes never leaving Britney's smug smile. She could feel the stickiness of Kyle's cum on her face, and the humiliation washed over her in waves.

"That's it! Now, I can talk and yet ;et Brad taste the surprise," Britney chuckled, her voice dripping with satisfaction. She gave Kyle a hand-wave and strutted away, leaving him and Cory alone in the empty hallway.

“I'll be fucking your pussy after lunch, slut," Kyle told blushing Cory as they parted ways. Cory nodded, her cheeks aflame, and scurried off to class. Kyle couldn't help but smirk, the life couldn't be better. Except for one thing, Kyle still couldn’t figure out how to get his language teacher.

Later that night, back at home, Kyle lounged in his room, scrolling through the app with an idle finger. His brain, however, was working overtime. Emilia Walker—the sweet, red-haired language teacher—had a profile in the app, but no role had been assigned to her yet.

If only there was a way to change it, but she was unmarried and was not spilling any beans about her boyfriend. Kyle was not even sure if she had one. Then came the idea. If you cannot change the objective role, why not try the subjective?

"Cory," he called out, breaking her moving her head up and down his cock, "Come here." She immediately stopped and crawled over, her eyes filled with curiosity.

"Yes, Master?" she said, eyes lowered respectfully.

"I need you to do something for me. Get a prostitute. Online, discreet. I want someone older, professional… and ask her to act like a teacher."

Cory blinked, startled. "A... prostitute?"

He waved her hesitation away. “Don’t worry. She won’t be here long.”

Once Cory left, Kyle opened the app and began to review the vacant role tags. Emilia’s profile shimmered with potential. It was a basic entry now—Name: Emilia Walker. Age: 30. Occupation: Language Teacher. No linked roles.

Half an hour later, Cory returned. “She agreed. She’s coming in about an hour. Her name’s Ruby.”

Ruby arrived on time. She was in her late thirties, wearing a fitted blazer and skirt combo that screamed "sexy professor." Her auburn hair was pulled into a loose bun, with glasses perched on her nose. She looked the part already.

“You’re the kid?” she said, raising an eyebrow with an amused smirk. “You’re into role-play, huh? Want me to scold you for skipping class?”

Kyle didn’t answer. Instead, he tapped her name into the app and opened the switch window. The screen split: Ruby – Current Role: Escort (Teacher Role-play/client – Kyle). Emilia Walker – Current Role: None.

He clicked "SWAP."

The app buzzed. Ruby blinked twice. "Sorry, I… actually I think I have the wrong client." She stepped back, confused. “You said you were—Never mind, I should go.”

Kyle watched her leave, his heart pounding. A minute later, his phone vibrated.

**New Message: Emilia Walker**

*Hey Kyle, sorry if this is weird, but did you still want to meet? Today works, or tomorrow might be easier. Let me know.*

Kyle grinned. It had worked.

She arrived promptly at 8:30 p.m., wrapped in a beige trench coat, her fiery red hair tied back in a low ponytail. She tapped at the front door lightly, her phone in one hand, her purse slung over her shoulder. Kyle opened the door w...

“I don’t have much time,” she said briskly, stepping inside. Her voice had that mix of embarrassment and urgency that made Kyle’s stomach flutter with amusement.

“My boyfriend’s home,” Emilia explained while slipping off her coat to reveal a tight cream blouse tucked into a high-waisted pencil skirt. “We planned a romantic evening. Takeout, candles. I told him I had a lesson to give… just not who or what it was.”

Kyle leaned against the wall, arms crossed, app open behind his back. “So while he’s lighting candles, you’re over here playing sexy schoolteacher for his student?”

Emilia didn’t meet his eyes. “Let’s just get this over with.”

Kyle tilted his head. “Oh no, Miss Walker. If you’re my slut, I expect a little enthusiasm. Don’t you think it’s more fun when the teacher tries?”

She flushed. “I’m not—”

“You are,” he said calmly, tapping the phone with one finger. “You're my sexy language teacher now. That's your job, isn't it?”

Her breath caught. “Kyle, do you really want to do that role-play.”

Kyle smirked. “100%? Common teach, give me an oral lesson!”

Kyle lead his teacher to his room, his hand firmly on her back, guiding her to his bed. He watched her every move, the way her tight skirt hugged her curves, and the way her blouse stretched over her generous chest. As they entered his room, she couldn’t help but take in the mess of books and clothes strewn about, a stark contrast to the neatness she always maintained in class.

"It seems you need to learn a lot, Kyle!" Emilia said, her voice shaking slightly with a mix of excitement and nerves. She took a step back, her hand shaking as she loosened the tie that held her hair in check. The fiery red locks fell around her shoulders, framing her face like a fiery halo.

"Oh yea? What am I missing?" Kyle grinned and spread his legs sitting on the edge of his bed, the tent on his pants pointing straight at her, demanding attention.

Emilia smile and used her best teacher tone, "Let's start with the basics, shall we?" She knelt in front of Kyle, her eyes never leaving his as she reached out to unbuckle his belt. "Now, Kyle, when you get excited, your penis gets hard." She pulled his pants down, revealing his erection, which bobbed up and down with his pulse. "It's called an erection," she whispered, her eyes widening slightly as she took it in her hand.

"It's a very simple process, really," she continued, stroking him gently, watching his face for reactions. "Your blood rushes to the penis, making it firm and erect." She leaned in and kissed the tip, her lips leaving a wet trail down the shaft. "It's quite fascinating, isn't it?"

"And these," she said, her hand moving up to cup his balls, "These are testicles. They're where the sperm is made." She kissed his thighs, her tongue tracing the lines of his muscles. "But we're not going to focus on those today, are we?"

Her eyes glinted with mischief as she stood up and unbuttoned her blouse, revealing a lacy black bra. "Now, these," she said, pushing her breasts together, "These are breasts. Or, as some people call them, tits." She reached behind to unclasp her bra, letting it fall to the floor. "They're used for a baby to drink milk," she explained, her voice a little breathless as she straddled him.

Her skirt rode up, and she slid her panties aside. "But they can also be used for pleasure," she added, her cheeks flushing as she lowered herself onto his cock. "You see," she gasped, "When you touch them, or kiss them, or when they're squeezed, it feels good."

"Can I kiss them?" Kyle asked, his voice low and hungry.

Emilia giggled, a sound that was so unlike her usual stern teacher persona. "Of course," she replied, leaning forward. He took her breasts in his hands, feeling their weight and warmth, before bringing his mouth to one of her nipples. He flicked it with his tongue, watching as it grew hard and erect. "Good boy," she murmured, rocking her hips slightly.

"Now, let's move on to the next lesson," she said, her voice taking on that authoritative tone that sent shivers down his spine. She leaned back, her breasts bouncing with the movement. "These are called nipples," she said, taking his hand and placing it on one. "When you play with them, it feels good for both of us."

Kyle took the hint and began to suck on her nipple, his teeth grazing the sensitive flesh. She moaned, her hips bucking as she rode him. "You're such a good student," she breathed. "You make me feel so good."

For minute or two Emilia tried to keep her breath slowly moving up and down, feeling her student's cock in her pussy, and his lips on her nipples. When suddenly, her phone began to ring. She froze, her heart racing. "It's my boyfriend," she whispered, her voice filled with panic.

"Don't worry," Kyle murmured against her skin, not missing a beat, "just answer it." He sat up a bit, his cock still buried deep within her.

Her eyes went wide, but she knew she had ****. She picked up the phone, her hand shaking. "H-hello?"

Her boyfriend's voice was on the other line, and Kyle could hear the muffled concern through the phone. "Is everything okay, Emilia?"

"Mmhmm," she moaned, her hips still moving. "I'm just giving... extra tutorship," she whispered into the phone, her voice thick with lust.

Kyle's eyes sparked with mischief as he reached to her nipple and squeezed it, making her gasp into the phone. "Miss Walker, I think you need to pay more attention to me," he said, his voice low and commanding.

Emilia's eyes widened, her breathing becoming more ragged as she tried to keep up the conversation with her boyfriend while Kyle's cock filled her and his teeth grazed her sensitive peak. "Yeah, I-I'm just... busy," she stuttered, her cheeks flaming red.

"I see," her boyfriend said, his tone hinting at suspicion. "Well, make sure you come home soon."

"I will," she promised, her voice tight with pleasure. Kyle didn't let up, his other hand reaching down to rub her clit in time with his thrusts.

As she hung up, she threw the phone aside and leaned back into Kyle's touch, her breath coming out in **** pants. "Oh, God," she moaned, her body tightening around him. "Make me cum, Kyle."

"Oh, yea? Slutty teacher wants to cum on her student's cock? That's a bit naughty, don't you think?" Kyle smirked, his hand moving faster, his teeth pinching her nipple gently.

Emilia's eyes rolled back into her head, and she couldn't form coherent words. All she could do was nod vigorously, her body begging for release.

He leaned in, pressing his lips to hers, swallowing her moans. His hand found her neck, squeezing gently but firmly, as he felt her walls tightening around him. He knew she was close, and the thrill of it had him on the edge too. With a final, deep thrust, he pushed her over, and she screamed into his mouth, her body convulsing as she came hard.

He didn’t stop, his hips moving faster and faster as he chased his own release. Emilia’s nails dug into his shoulders, her breath coming in ragged gasps. He felt himself getting closer, the pressure building in his balls. With a roar, he came, filling her up with hot cum. They both collapsed on the bed, breathing heavily, their bodies sticky with sweat and passion.

Emilia’s eyes were glazed over, her mind still reeling from the intensity of her orgasm. She looked up at Kyle, her chest heaving. "That was..."

"Oh yea, I bet I showed you some new tricks, teach?" Kyle's smug voice filled the room, his cock still twitching from the aftershocks of his orgasm.

"That was five hundred dollars worth," Emilia said with a gasp, her breath still ragged from their intense encounter. She slid off Kyle, her legs shaky but her mind clear.

Kyle's smirk fell, and he looked at her in confusion. "What are you talking about?"

"Our little... arrangement," she said, her voice still laced with desire. "You know, the one where I have sex with you, and you pat me money. Kyle, you do know how prostitution works, do you?"

Kyle's smug smile fell from his face as reality hit him like a ton of bricks. He had been so caught up in the moment that he had forgotten about the transactional nature of their encounter. "Oh," he murmured, his voice small and deflated.

Emilia stood up, her legs wobbly as she reached for her bra and blouse. "Don't worry," she said with a knowing smile, "it's not like I don't enjoy it. But a girl's gotta get paid."

He nodded, his face reddening as he reached for his wallet. He pulled out three crisp 100 dollar bills, fuck.

"You can dress up, I'll meet you downstairs!" Kyle called out, his voice echoing through the hallway as he rushed to get dressed. He had a plan. A plan to make sure he could keep his sexy language teacher coming back for more... lessons. He knew his parents wouldn't be happy about giving him that kind of money, but he had to find a way to make it work.

Knocking on his parent's bedroom door, he took a deep breath and tried to compose himself. "Mom? Dad? Can I talk to you guys for a sec?" He heard the muffled sounds of his parents shifting before the door finally opened.

Sarah looked at him with a knowing smile, while Mark's eyes held a hint of confusion. "What's up, Kyle?" Mark asked, his robust laugh from the night before nowhere to be heard.

"I, uh... I need some money," Kyle stuttered, his eyes darting between them. "It's for... uh, a school project."

"How much?" Mark's voice was gruff, his arms crossed over his chest.

"Two hundred dollars," Kyle said, his voice barely above a whisper. He could feel the heat rising in his cheeks.

Sarah raised an eyebrow, her expression one of amusement rather than surprise. "A school project?" she repeated, her voice dripping with sarcasm. "That's a pretty expensive school project you've got there."

"Yeah, it's... it's for some special supplies," he said lamely, waiting for his dad to pass him the bills.

"Thanks! Enjoy your... drama!" Kyle closed the door behind him, feeling the weight of the cash in his pocket. He took the stairs two at a time, his heart racing as he descended into the living room.

Emilia was waiting for him, her trench coat buttoned up to her neck, looking every bit the demure teacher she portrayed during school hours. But Kyle knew better—he had seen the wanton desire in her eyes, felt the heat of her passion just minutes ago.

"Here you go," he said, handing her the money. Her hand grazed his as she took the bills, sending a spark of electricity up his arm.

Her eyes searched his, and for a brief moment, Kyle saw a glimpse of vulnerability in them. "Is this... is this what you want, Kyle?" she asked softly. "To pay for me to do this with you?"

"I mean, that was fun. How much for a BJ, by the way? Maybe we can make this a regular thing," Kyle tried to play it cool, his heart racing with excitement and the thrill of his newfound power.

Emilia took the money, her gaze never leaving Kyle's. For a brief second, he saw something flicker in her eyes—a mix of amusement and resignation. She tucked the bills into her purse and gave him a knowing smile. "If it's just BJ, without freaky role-plays, I can do for a hundred."

Kyle watched as his sexy language teacher got to her car, and after giving him a little hand way, pulled out of the driveway. Kyle decided that whatever explanations for the "school project" he has to do, can be done tomorrow.