The Lesson Pt 02 Transgressions

Authors Note:

Thank you all for enjoying The Lesson. This sequel was written, in part, to extend the story for the many readers who enjoyed the first installment. If you haven't had the pleasure yet, you can view it here:

http://www.literotica.com/s/the-lesson-36

Thank you again, and I hope you enjoy reading this as much as I enjoyed writing it.

*

The phone rang three times before Madeline became aware of its presence. Her mind was occupied with more interesting surroundings and scenarios, and the reality of answering another call from a customer who's porn connection was down did not entice her at all.

"Technical Support, this is Madeline." She gave the rote greeting with no inflection.

Her mind wandered again. It had been three weeks since her wonderful evening with Janine and Jason. Three weeks since they had opened her eyes to a whole new world of sexuality through dominance and control. She had done research since then, which registered high on her 'lame-o-meter', but once it became clear Janine and Jason would not be inviting her back for another round of play, she searched for knowledge wherever she could.

She learned quickly that her experience with the couple was rather tame in comparison to what was out there. Pain was barely present, and the force applied was minimal. Everything was new and frightening to her in the moment, though she learned through various articles and 'video tutorials' that the Dom/Sub lifestyle was not always as tender as she had experienced.

Thoughts of Janine's nigh perfect body rocking against her with the strap-on flooded her mind, her red hair swishing back and forth over her shoulders which each thrust. She had never been attracted to women in more than an academic sense, but she had to admit Janine was more than just a figure she could admit was pretty. She actively turned Madeline on.

Then her mind wandered to Jason.

His well-built frame, sandy hair, and voice sweet as chocolate resonated in her memory. Guilt plagued her, as he was her friend's significant other, but she couldn't help but lust after him. Despite the wonderful evening, and earth shattering orgasm she had experienced, she had yearned to be properly fucked by the man. His cock had filled her mouth, which had been a great start, but the fun ended with Janine penetrating her from behind, and Jason shooting his cum down Madeline's throat.

"Hello?!" An angry voice echoed through her headset.

"Sorry," Madeline sputtered, shaking from her memories. "We have a bad connection, could you repeat that?"

A pervasive dampness confirmed she was not going to be able to concentrate tonight.

*

Madeline rummaged through her purse. The jingling of her keys were deceptive, as they proved they did in fact exist, but seemed to be invisible and intangible as her hand worked from side to side inside the pouch. She let out a frustrated growl as she stopped to focus all of her attention on the search.

"Madeline!"

Madeline would have dropped her purse if not for the strap wrapped around her arm at the sound of the bubbly voice behind her. Janine smiled, her red hair assuming it's perfect position to frame her face.

"Janine!" She exhaled. "You scared the bejesus out of me."

"Sorry," Janine gave a playful pout. "I wanted to make sure I caught you though. We never see each other since my shift got switched around."

"Yeah, I miss you guys." Madeline paled slightly. "I mean, miss you! Well, both of you, I guess, but... not that..." She flushed crimson as she continued to fumble her words.

"It's okay," Janine gave a beaming smile. "We both miss you, too. Jason actually brought you up yesterday, which is why I'm glad I caught you."

The twinkle in Madeline's eyes could not be hidden, and she felt ashamed at the glee she felt in response to Jason's thoughts of her, no matter how benign.

"We'd like to invite you to dinner tomorrow night at our house." Janine continued.

Madeline's thoughts swirled into a tempest. 'Is this it? Are they inviting me back for more than just food and good company? Would I be able to live out the fantasies I have been concocting for the past three weeks?' Her smile broadening, and her cheeks flushing, she tried to formulate a response before realizing Janine was not finished with her invitation.

"It's going to be a small gathering," She said casually. "Only about 8 or so, not including the three of us, but they're all good people."

Madeline's thoughts of the evening began to decline. 'This is not an invitation to play... or is it? Is there going to be an orgy of some kind?! That's not enticing at all. I just want Jason... and Janine, of course.' Though she was unwilling to admit it on the surface, she wanted someone very specific, and she was barely willing to share with one other.

"Some of them are pretty boring, truth be told." Janine admitted. "One couple is in their 60's, and are old family friends of Jason's. I suffer through their stories and questions, but Jason has known them since he was riding tricycles, so he keeps in touch."

'Definitely not an orgy,' Madeline confirmed internally.

"Anyway, dinner will be at 7, people will show up after 6." Janine checked her watch. "Crap, I'm late. Anyway, I'll be off that day at 3:30, so come over at 4 and we can all catch up while we prep for the night."

A glimmer of hope sparked in Madeline's chest. They would need to prepare dinner, but that gave them hours of potential.

"I can't wait," Madeline replied with a genuine smile.

*

A soft gasp escaped her lips as hands caressed down her breasts. Fingers teased at her nipples and gave a playful pinch. Her grin broadened as her legs were roughly forced open, and her lips were spread by eager fingers.

Madeline's breath came in short gasps.

She wanted it.

Craved it.

Needed it.

As fingertips stimulated her clit, another found its way around to her ass. She bit her lip and whimpered. She liked the light teasing, but had never been brave enough to invite more than a fingertip inside her forbidden area. But given the circumstances, it excited her.

"Jason..." She let the name out with a breath. "Please fuck me."

As if on command her pussy began to spread, and her body locked up with pleasure. Her face froze in ecstasy as the first inch pushed inside her, and she began shivering as her first orgasm began to rise.

A rude rattling from her bedside table intruded in on the moment.

Madeline's eyes shot open, shattering the illusion she had built in her mind, and violently pulling her back into the reality of her empty bedroom, and the dildo in her hand.

Her phone vibrated again, rattling against the wooden surface.

"Ffffffuck!" She cursed, reaching over and hitting Ignore with prejudice.

She took a few deep breaths to center herself before checking the time. 1:00 pm. She needed to get to sleep if she was going to get to work at 11 pm well rested. That was crucial if she planned on being awake for dinner... or more importantly, pre-dinner... the next day.

With a few more breaths, she closed her eyes, and resumed her fantasy.

*

The minutes crawled by. Calls that normally sped the evening by seemed to be few and far between, leaving Madeline restless and counting down the seconds until the end of her shift. She got off at 7:30 am, which gave her enough time to take a quick nap, shower, and beautify herself for the dinner party.

Though it was less than 12 hours away, it seemed like it would never come.

*RING*

Madeline answered the call gleefully, inviting the distraction from the ever slowing second hand.

"Technical Support, this is Madel-" She stopped short, hearing the telltale heavy breathing on the other line. It was a hazard of working in phone support for porn: You got your share of weirdoes who liked to call and hear a voice to help get them off. She reached forward to disconnect the call, and stopped half an inch short from the button.

Her mouth quirked into a grin.

"Can I help you, sir?"

A grunt came from the other end of the line, but no words.

"Mmmm," She gave a pleasurable moan. "Is that for me?"

The breathing stopped for a moment, as did the noise. The caller was clearly not expecting a response, much less a positive one.

"I'm all alone," She said in her best pouty voice. "Why won't you talk to me?"

A long pause, then a low, almost whispered response, "Yes."

"Yes?" She chimed back. "Yes it's for me?"

A grunt in assent was the only reply. The breathing picked back up, and muffled, slick sounds could be heard in the background.

"Tell me what you're doing to me..." She encouraged. The realization entered her mind that her job would be quickly ended if they reviewed this call, but she pushed it aside. Something in her needed this.

"F...fucking you." The voice grunted quickly.

"Oh, sweetie," She cooed. "You can do better... am I bent over my desk for you?"

"Y-yes..." The sounds became more urgent, and the voice raised an octave. "T-take off your top!"

"For you baby, anything." Madeline breathed into the mic. "Oh baby, my nipples are hard for you, will you cum on them?"

A strained gasp came from the other end of the line, and a few seconds passed as the man finished himself off. A few more moments of breathing and silence preceded the inevitable hang up.

"Aww, no cuddling?" Madeline grinned, resetting her phone for the next call. Something deviant was stirring inside her, and she embraced it. She liked the exhibitionist mood she was in, and prayed it stayed with her until the party.

*

'It's coincidence that I'm early.' Madeline told herself as she crossed the cobblestones to their entryway. 'There was no traffic, and the stores had no one in line. Otherwise, I'd be here right at 4. Not... 3:15. And not in my favorite pencil skirt that shows off my thighs... or wearing my favorite lingerie underneath...'

She shook her head to clear the obvious lies to herself. Though she had no plans, her intention to have some alone time with Jason before Janine got home was hard to justify. He was taken, and unerringly loyal to his wonderful girlfriend.

The doorbell rang, and Madeline hoisted the bag of groceries into the crook of her arm while she waited. She heard movement inside, though it took much longer than expected before the door began to open. Her patience was rewarded by a gleaming smile beamed down at her from the tall man in the doorframe.

Feeling like a schoolgirl with a crush, she hunched her head and blushed, "Hi Jason."

"You're... early." He said, more curious than annoyed. "Sorry, I wasn't ready yet." He paused for a second before realizing he was blocking her way. Stepping to the side he waved her in, "Come in, come in."

She scuttled inside, nerves jumping through her skin. Though the three of them had enjoyed lunch at a public restaurant, and coffee at a local Java House, she had not been back in their home since that wonderful night. A deep breath of the pleasant scents brought back memories of the kept home she had been eager to be invited back to.

"I'm not a fantastic cook, but I have a lasagna recipe that hasn't failed me yet," Jason smiled as he passed her, heading back to the kitchen. "Come on back, we can share some of this new Cabernet Sauvignon I opened."

Madeline was more of a white wine drinker, but that could be pushed to the side for now.

"So, who all is coming tonight?" She asked, trying to keep her stomach from fluttering.

"A few work colleagues, an old buddy from college, and a couple family friends who've I've known since-"

"You were riding tricycles?" She finished with a grin.

"Yeah," He smirked. "Janine told you, huh?"

"About them, yes. I didn't know the rest."

Jason nodded, handing her a newly poured glass of wine. "What shall we toast to?"

'Me on my hands and knees for you.' Madeline thought, hoping her eyes didn't betray her inner monologue. "To friendship?"

He grinned, "To friendship."

Glasses clinked, and ruby liquid poured past their lips. Though her preference was far from the bold vintages they sampled, Madeline knew she could grow to like this wine.

"So, Janine isn't due back for at least half an hour, but I know she's looking forward to this." He said, moving a pan out onto the counter. "She's been talking about it all week."

"Really?" Madeline grinned, shoulders twisting coyly. "I was told this was your doing."

'Madeline, stop it.' She chided herself. 'You're shamelessly flirting.'

"Well," He grinned knowingly, avoiding eye contact. "Truth is-"

His pocket vibrated, and was followed by a classic punk song. The lyric started speaking of 'fingertips' and 'memories', and Madeline knew the tune instantly. She also knew whose custom ringtone that had to be.

"Speak of the devil," Jason grinned, freeing his phone from his pocket. With a click of a button, he raised the phone to his ear. "Hey baby, how's work?" Jason smiled at Madeline as he listened, then seemed to pause. "Really? Mandatory overtime? For how long?"

Madeline felt her knees getting weak. Fate seemed to be aligning, and she was filled with false hope. Even if they had the entire night together, Jason wouldn't stray from Janine.

"Nope," He said, his smile spreading. "No one is here yet, but I'll make do on my own 'til you get here."

Madeline froze.

'Why would he lie?' She thought. 'You know why, dummy, there's only one reason to. But that means...'

Her eyes went wide and her pupils dilated with desire. Something was wrong about this. But despite everything, she didn't care. She wanted the opportunity, and despite the wave of lies she told herself, she knew she would take it, and enjoy it if it was offered.

"I love you too, babe. I'll see you when you get home." He ended the call and slid his phone back in his pocket, his eyes locked on Madeline's the entire time. "So... apparently Janine will be delayed until at least 6. That's a shame."

"Yes," Madeline squeaked out. "A shame."

A long silence filled the space between them.

"So, we have some time to kill." He scooped up his glass. "Let's go into the living room. I'll tell you how Janine and I first got together."

Madeline nodded wordlessly, cupping her own glass in both hands as she practically scurried out into the living room. She took a seat on the couch, and was silently pleased when Jason sat on the next cushion over.

"So what was your first date like?" Madeline tried to sound interested and confident, but her voice shook, and she knew she exude a calm demeanor.

"A nice dinner in the city, a little dancing, and then a few too many drinks at a local dive bar down the street." He grinned. "We stumbled back here so we could sober up before I drove her home."

"I can guess you guys didn't make it far past the entryway." She grinned, but noticed a thick guilt rising beneath the surface. This was her friend and her boyfriend she was talking about, and she had impure thoughts raging through her. This was wrong...

"Actually, we were both determined not to have sex on the first date." He said smugly.

"Really...?" Madeline said with disbelief. "So, you didn't... at all?"

"Well," He bobbed his head as if dodging facts. "We found a way around it. We played chicken."

"Chicken?" Madeline's expression shifted to puzzlement.

"We'd get close," He said as he slid next to her. "Like this, and move as if we would do something inappropriate, but then stop. The game was to tempt and tease, but not act. And if someone broke, they owed the other person a favor."

"Really," Madeline said, feeling Jason's warm breath against her cheek as he spoke. "What kind of favor?"

"Anything the winner wanted, so long as it could be completed in one minute."

Madeline flushed, hiding her grin behind her hand.

"Yeah, I thought it was fun, too." Jason's voice caressed her ears, and his smile eased her nerves. She knew then mountains would not stop her. Weeks of desire and pent up fantasy were fueling her every desire and shaking her will to nothing. She wanted him desperately, and something told her with the right invitation, she would have him.

"So, if you were sitting like this," Madeline said coyly, "I could turn like this and it would be 'legal'?"

She turned and placed her hand on the couch cushion in-between his legs, her eyes raising up to meet his.

Jason's eyes didn't leave hers, and his smile seemed to shine brighter at her action. "Right, and then I could do something like this..."

He slid his arm across the back of the couch and over her opposite shoulder. His hand hung down, hovering an inch over her breast.

"Hmm, I think I understand." She said, mocking an innocent ignorance as she placed her wine on the coffee table. "So I could then pull this down?"

With her free hand, she hooked her finger in her top between her cleavage, pulling it down a few inches to accentuate Jason's view.

"Not just that," He responded, gladly taking on the role of the teacher as he leaned in. His lips were centimeters from her earlobe, allowing each breath to sweep across her skin. "Words are fair game, too. So I could tell you I've wanted to fuck you since we first met, and that we have a house all to ourselves for hours."

Madeline melted, and she felt her hand slip up the couch and onto Jason's jeans. The bulge of his dick could be clearly felt, and a shockwave of pleasure jolted through her body.

"Ah ah ah," He chided playfully, nipping at her earlobe before continuing. "That lost you the game. You owe me a favor now."

"Oh really?" She said, pressing sideways against him while pulling her top down more. It stretched the fabric to completely reveal her lacy bra, but she didn't care. She wanted to entice him, to make him want her as bad as she wanted him. She wanted him to carnally take everything he wanted from her until they were both reduced to gasping piles of flesh on the floor. "And what favor is that?"

"I want you on your knees." He tapped the couch between his legs. "Right here."

Without any further coaxing, Madeline whimpered and slid onto her knees on the floor. She remained between Jason's spread legs, looking up at him with pleading eyes.

"Unzip my pants." He said, the casual dominance she remembered returning to his voice.

As she reached up and did as he asked, she smiled, "But you only get a minute?"

"I'm sure we can figure out something to make it last." He smiled, intertwining his fingers into her hair.

In seconds, Madeline had freed his cock from his pants. It was as she remembered, larger than average, but not too big. It stood straight at attention, and she savored the sight for a moment. She was reminded of her owed favor as Jason applied pressure to her head. He guided her firmly down onto his cock, and pressed half of it past her lips.

If the sigh from Jason's lips was a sound of pleasure, the moan coming from Madeline was one of pure elation. Janine was forgotten for the time being, and her body instantly responded to the object of every fantasy she had nursed for the past few weeks.

Jason guided her up and down his shaft, and she eagerly brought her hands into play to caress his cock and massage his balls. She wanted to please him, but she reminded herself not to make him cum. Despite her overwhelming desire to bring him pleasure, she needed to feel him inside her.

She sucked greedily, trying to take him in farther, but she knew she did not have the same tolerance for depth as Janine did. Despite her perceived flaws, she continued up and down eagerly, determined to impress Jason.

A quick succession of sounds behind her brought her out of her trance, and she realized something was very, very wrong. The wood slamming against wood was unmistakably a door, and the only doors behind her, aside from a bathroom and small closet, was the front door.