Sinful Tutoring: Next Semester Pt. 02

As with the previous part and story, this wouldn't exist without the amazing content of the lovely Synful Mistress/Mistress Everlynn/Synful420B. If you like these stories you'll love her.

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She stared down at him, spread-eagle and naked on her bed. Wrists and ankles bound tightly and the blindfold off to the side.

His eyes were wide with fear as he took in the sight of her strap-on- far bigger than his own cock, much as he hated to admit it.

Some nights, she didn't even have to try. This was one of them.

Mistress Syn had picked him up earlier, although she'd scarcely had to do anything but sit there and wait. He'd spotted her across the crowded campus bar and likely assumed she would make for an easy lay based on her choice of 'costume' for the evening.

He couldn't have been more wrong.

It was the school's Halloween mixer, which meant a mess of drunken students sporting cheap costumes and trying to get in one another's pants. Syn had shown up more or less dressed as she usually was in her spare time. And if someone thought it was simply a costume, well, that was their mistake, not hers.

A pair of over-the-knee red and black laced-up leather boots, black fishnets covering her toned, tattooed legs, a green plaid tied top which showed the slightest glimpse of her purple bra, and a spike-covered leather mask with cat ears completed the ensemble.

If anyone were to hazard a guess, they would probably assume she was dressed as some kind of twisted schoolgirl.

Which frankly, she was.

Even if no one knew it. Least of all him.

The moment he started making his way towards her, Syn made him almost immediately. The fact that he was wearing probably the most basic of costumes- a caveman, with a cheap animal print loincloth and a plastic club was proof he really wasn't the brightest. Add in that he was tall, muscular, and had been hitting on everything with tits over the course of the night, that was all she needed to know.

Odds were, he was some jock type who'd wound up here on an undeserved scholarship and was trying in vain to relieve his glory days. Pathetic.

Not that that didn't mean she couldn't have some fun with him. She was in the market for a new toy.

Oh, she'd managed to give Shawn a few more lessons since he'd 'accidentally' stumbled into her dorm at the beginning of the semester, but Syn needed some variety. And this guy certainly fit the bill.

From behind a pair of slightly demonic yellow contact lenses, she watched him close in on her. Flashed him a smile so seductive that there was no way he could ever hope to resist. Like so many before him, he took the bait hook line and sinker, and the moment he stopped in front of her, Syn prepared to reel him in.

"Hey," he started, slurring his words yet still carrying the misplaced confidence guys like him tended to hold onto like a security blanket. "Does the kitty like to be petted?"

Mistress Syn suppressed the urge to roll her eyes. Typical asshole alright. Which of course only made her want to break him even more.

"Maybe," she replied, her voice sounding as sweet and innocent as possible.

That seemed to do the trick, and he placed his red solo cup down on the table in front of her... "I'm Jake baby, but you can call me Daddy..."

The poor bastard had no idea what was coming... Or who would be calling who what before the night was over.

"My name's Cynthia," she replied, never breaking character. "But everyone just calls me Syn..."

She didn't reveal that the people who called her that tended to add a title to go along with it, but what Jake didn't know wouldn't hurt him. Much.

He looked her up and down, taking in the sight of her lovely legs and ample chest, and his expression told her that he certainly agreed with the nickname. "Well, how 'bout we blow this joint and you can show me just how sinful you are..."

With a twirl of her purple hair around her black-painted fingernail, Syn giggled. "Sure... My dorm's not far from here."

Jake's eyes widened as he finished his drink. He honestly believed he was going to score. After being shot down by every other girl he'd tried with tonight, his luck had finally turned around.

At least, that's what he thought.

Syn practically led him by the hand out of the bar and across campus, moving slowly so that her drunken conquest-to-be wouldn't fall behind. Or just fall. Not that she thought he would- his eyes were so clearly glued to her fishnet-covered ass that he would likely follow her straight into Hell if she asked him to.

Which wasn't all that far from what she had in mind.

The moment they were inside, she silently beckoned him with her finger towards her bedroom, and Jake practically fell over himself as he stumbled after her.

"Wait," she said coyly as they stood just outside the door. "Put this on first. Please?"

She handed him a black blindfold, and he was so horny, so drunk, so desperate, that he didn't think twice as he slipped it around his head.

Once it was tied, she took his hand again and led him into her bedroom, then playfully pushed him onto the bed. Taking hold of his wrist, she slipped it into the first restraint and secured it tightly.

Jake didn't struggle, figuring in his inebriated state that she was just into some kinky stuff. Which she was, just not the sort he was liable to enjoy very much. His other wrist followed, then his ankle, and he didn't even fight when he felt her slowly remove the loincloth of his costume.

The only clothing he was wearing, as it turned out.

But if he thought he would soon feel her slide on top of him, he was dead wrong.

Instead, the next thing Jake heard was Syn stifling a laugh. One which quickly burst free from her lips.

"Oh my God," she began, still giggling. "I knew guys like you tended to have tiny dicklets, but that's even smaller than I expected!"

Drunk as he was, Jake was still taken aback by her comment. None of the girls he'd been with before had ever dared say that about him, and this creepy bitch thought she could. Fuck that. He was done and struggled against the restraints in vain as she continued to laugh.

"Shut the fuck up!" He yelled, but Syn kept laughing, making him feel as small as his cock truly was.

"Here," she continued, her giggles finally subsiding. "Let me show you what a real cock looks like."

Jake heard her bootheels click against the floor as she walked towards the head of the bed. And once she stopped, she pulled the blindfold off, and the moment he could see again, his expression turned from anger to outright fear.

Syn was standing there, a huge black strap-on in her hands. One she had every intention of using on him.

"Aww, did you think you were gonna get to fuck me tonight?" She asked as she slipped the harness on. "Silly Trinket. The only one getting fucked tonight is you. Slowly."

Sobering up as much as he could at the sound of that, Jake shook his head in anger as he continued to struggle against the restraints, but Syn wasn't the least bit intimidated, no matter how much he tried to cuss her out. "You crazy fuckin bitch, untie me right now!"

Instead, Syn walked over to her dresser and picked up something that made him even more afraid.

A gag.

But not a typical ball gag.

This one had a small cock on it.

"Sorry sweetie, but if you're gonna keep calling me a bitch, I'm gonna have to shut you up."

He tried to move his head to stop her from shoving it in but restrained as he was, Jake had little to no control over the situation he was in. Syn simply grabbed a hold of his face with one hand and shoved the gag in, cock first, then closed the strap around his head. "Suck on that for a little bit."

Much as he didn't want to, he had no choice. It wasn't leaving his mouth anytime soon, and one way or another, he had to suck it.

Syn made her way to the end of the bed, where his naked ass lay waiting for her, and once she was there, Jake's eyes got even wider.

From behind the gag, he tried to plead, to beg her not to go through with this. And though she couldn't hear him, a wicked grin still filled her face. "Oh, don't worry 'Daddy'. I'll be gentle... At least to start."

Dropping a wad of lube onto the smooth, black rubber, Syn slid her hand up and down until the cock started to shine under the dim fairy lights of her bedroom. Then she took hold of his legs for support and slid the tip into his tight little asshole.

Jake tensed up immediately, still hoping in the depths of his drunken mind that this was just some weird kind of foreplay and that she would eventually untie him and let him fuck her... Yet no matter how badly he tried to clench, no matter how much he wished his asshole would remain shut, Syn was determined to shove her cock deep inside him.

And the more she pushed, the more he knew that like it or not, she was going to get her way.

At first, only about half of the slick rubber phallus made its way inside him, the cool sensation of the lube making it feel a little better than he'd expected. Then she started to pull it out slowly, and for the briefest of moments, he thought that was proof she was just messing with him.

Then she pushed it back inside, a little more this time, and Jake realized that much as he wished to believe otherwise, this was happening.

He groaned through the gag, the small cock pushing against his teeth and tongue, forcing him to lick it even unconsciously. Syn slid the strap-on in and out of his ass, seemingly refusing to put the entire length of it inside him. She wanted to wait, wanted to build up the dread and fear in his eyes before she fully committed to fucking him for all he was worth.

The same fear and dread that was already getting her so wet.

There was just something about having a man at her mercy like this, especially one who was clearly used to just fucking random women with his useless cock, that made her pussy throb like nothing else.

"Just relax sweetie," she said mockingly, sticking a little more than two-thirds of her cock inside him this time. "It'll be so much easier if you just let me fuck you like the little slut that you are..."

Jake shivered, both from the sensation in his ass and her words. He hated being called a slut, but he also knew she was probably right. If he stopped resisting, it might not feel so bad... Even so, he didn't want her to give her the satisfaction. He was going to fight as much as he could.

Unfortunately, that wasn't all that much in his current state.

The strap-on slid out once more, Syn leaving on the tip inside him this time. She sighed. He was going to have to learn things the hard way it seemed.

Luckily, she loved teaching those kinds of lessons the best.

"Can't say I didn't warn you," she said, then shoved the full length of the cock inside his ass.

Jake's eyes shot open as he felt the rubber balls of her strap-on bounce off his cheeks, Syn's cock practically impaling him. He groaned once more, but much to his dismay, it wasn't all in discomfort. A small part of him- one he'd rather not listen to right now, didn't mind the feeling at all.

It likely didn't help matters that, crazy as she clearly was, Syn was still extremely hot, and the fact that she was enjoying herself turned him on just a little. He could see the mix of sweat and pussy juice leaking out from behind the harness and along her legs, and the sight of that was enough to break down what little defenses his drunken brain still had.

"Mmm, see how wet this is making me Trinket? This is the only way a slut like you can ever hope to get me off."

She laughed wickedly, and Jake shut his eyes in despair. But that was far from the worst of it.

"Aww, I think you're enjoying this too, aren't you bitch?" Syn giggled, looking down at his cock.

It had started to get hard somewhere along the way, much to Jake's dismay, and he could only groan as he felt one of her lube-covered hands wrap around it. "You like getting fucked by my big cock, don't you?"

He tried to shake his head, to deny the obvious truth, but she tightened her grip around his erection and started to stroke it slowly, her eyes practically boring into his own as she stared down at him. "Don't you dare lie to me Trinket..."

Another groan, and with it, all Jake could do was nod. He was starting to give in, and she loved it.

Syn's strap-on continued to slip in and out, his ass a little more relaxed now, and her hand began to slide up and down his shaft. After a few moments, they began to move in time, a shared tempo that started to break Jake down even more. No matter how much he tried to tell his cock to stop, it continued to grow in Syn's slippery hand.

Jake had never been fucked like this. The very idea of anal sex of this sort had never interested him, yet the more Syn fucked and stroked him, the more he realized he was coming around to it. And that terrified him even more than the strap-on did. This was twisted and wrong and he couldn't do anything about it.

Nor was he sure he even wanted to anymore.

After a moment or two, he shut his eyes, essentially giving up and giving in.

Syn smiled at the sight, increasing the speed of both her strokes and her assault on his ass. As she did, her other hand let go of Jake's leg and picked up her phone. Flipping it on and over to camera, she pressed record and started filming. This was going to be fun, and she didn't dare miss a single second of it.

The feeling of her cock pumping in and out of his ass in time with her hand moving up and down his cock began to mix together, and in his drunken state, Jake's brain was begin to link the two acts together in a twisted sort of way. The pleasure of the latter was being informed by the former, and whether he realized it or not, his mind was equating getting fucked in the ass with the orgasm building up in his hard cock.

Just as Syn intended.

"Mmm, feel that Trinket? You gonna cum for me? Gonna blow your load with my big cock deep in your fucking ass?"

A loud moan slipped out from behind the gag as Jake's mouth fully embraced sucking the gag stuck inside it, and Syn stroked faster, never letting up her assault nor stopping recording. Normally she wouldn't do something like this, but it would add so much to Jake's humiliation she simply couldn't resist.

His cock started to tremble in her grasp, and Syn happily added more fuel to the fire. "Come on, shoot that pathetic loser load for me. Let that tiny little dicklet sputter. Do it. Do it now!"

The moment she finished her command, Jake felt his cock seize up, and he bit down hard on the gag in his mouth as he exploded in her hand, a scream of pleasure just barely audible while she began to milk him even as her own cock continued to fuck his ass.

Not even when he felt the last few drops spill out of his cock did Jake dare open his eyes. So lost in the euphoria of Syn draining him that even her strap-on slowing down barely even registered.

It was only when she pulled it out completely that he decided to open them and look up at her.

Which was when he came face-to-face with the sight of Syn holding her phone, a wicked smile plastered across her lips. "Smile Trinket."

She snapped a few quick photos to go along with the video, then wiped her hands on his loincloth, staining it with his juices before walking over to the head of the bed.

Once there, she took a seat beside him and showed off what she'd recorded, and Jake's eyes filled with tears of shame as he watched her fuck him and make him cum at the same time. He felt completely and utterly degraded, and yet she still wasn't quite finished with him.

"Mmm, how badly do you want me to keep these a secret?"

Her question burned into his mind, and Jake realized what she was getting at. He struggled against his restraints once more, unable to answer her even as his expression spoke volumes. If anyone ever saw that video or those pictures, he would never live it down. He'd be mocked mercilessly, not to mention the fact that no woman on campus would ever have sex with him.

He was beyond fucked. And Syn knew it.

"I bet you'll pat a lot to make sure these never ever leave Mistress's phone, won't you Trinket?"

Jake sighed. She was right.

With a groan, he nodded his head.

Syn laughed, then removed the gag from his mouth. "I want to hear you say it bitch."

"I'll pay to make sure those never leave your phone."

She stared at him, her contact-covered eyes filling him with dread. "Never leave whose phone?"

Jake considered her question and realized what she wanted him to say. "I'll pay to make sure they never leave Mistress's phone."

"Good boy," she said, then brought the strap-on towards his lips. "Now open wide. You're gonna suck Mistress Syn's cock before you get to leave. Understand?"

He shut his eyes as the rubber cock slipped inside his mouth, He fought back even more tears as she slowly began to fuck his face, knowing that any dignity he may have had was now long gone. This was not how he'd expected the night to go, and it had only just begun.

As had his time as Mistress Syn's newest toy.

One she was looking forward to playing with again and again.