A Walk Through Town Parts 9-10.5

A Walk Through Town Part 9

When Maggie returned to class, she was a complete mess. The vibrator was still humming deep inside her, a constant reminder of the blackmail her professor had used against her. She had been reduced to a mere object, her body used for her pleasure for so long that every inch of her body felt hypersensitive. The scent of sex and arousal clung to her, a pungent reminder of her degradation.

She made her way to her seat next to Brian and the girl whose name she still hadn't learned. On her seat was a surprise—her shorts and shirt, neatly folded, but covering something beneath. As she peeked under the clothes, she looked at Brian and said, "You can't be serious."

Beneath the clothes was a massive dildo, attached to a suction cup, firmly fixed to her seat.

"Nope, completely serious," the girl replied, reaching under her hoodie for the string loop and pulling gently. The vibrator slipped out with ease, causing Maggie to cross her legs and pull down the hem of her hoodie, worried someone might have seen. But the lights were dimmed, and everyone was engrossed in the lecture. It was unlikely anyone had noticed, and even less likely that anyone in this class was awake enough to realize what was happening.

"Come on, or else," Brian spoke, reaching for the back of her hoodie and pulling it up just a bit, exposing her bare ass cheeks. She spun around and began to sit. The girl moved the clothes aside and held onto the dildo, guiding it into Maggie as she sat down.

Maggie eased herself onto it, her body, especially her pussy, so sensitive that the well-detailed and enormous dildo sent shivers through her. Her legs started to burn at the angle, and they gave out, taking the rest of the dildo in a hard thrust. She clamped a hand over her mouth, stifling a loud moan that caused a few students to stir and look back at her. Thankfully, her legs and body hid the secret now firmly planted inside her.

The sensation was overwhelming, her body trembling with a mix of pleasure and humiliation. She could feel the dildo spreading and filling her completely and touching every inch of flesh of inside her, a relentless reminder of her situation. She tried to focus on the lecture, but every movement, every shift in her seat, sent waves of sensation through her. She could feel the eyes of her classmates on her, wondering what had caused her to react so strongly.

Maggie's mind raced, her thoughts a chaotic mess. She had been reduced to this, a mere plaything for their amusement. But despite the humiliation, despite the pain, she couldn't deny the desire that burned within her and it terrified her.

Maggie's heart pounded in her chest as she realized the gravity of her situation. She was completely exposed, her body trembling with a mix of fear and arousal. The dildo, now a monstrous intruder inside her, pulsed with a life of its own, each vibration sending shockwaves through her sensitive flesh. She glanced around the dimly lit classroom, hoping against hope that no one had noticed her predicament.

Brian's hand, rough and commanding, continued its exploration of her ass, his fingers probing deeper, hitting spots that made her gasp involuntarily. The girl beside her, with a cruel smile playing on her lips, toyed with Maggie's nipples, twisting and pulling them with a sadistic glee. Maggie's mind was a whirlwind of conflicting emotions, her body betraying her with each new wave of pleasure and pain.

"Please," Maggie whispered, her voice trembling. "I can't take much more."

The girl leaned in closer, her breath hot against Maggie's ear. "You're doing great, Maggie. Just a little longer."

Maggie's body convulsed as another orgasm ripped through her, her muscles clenching around the dildo. She bit down on her lip to stifle a scream, her eyes rolling back in her head. The sensations were overwhelming, her body a battleground of pleasure and torment.

Brian's voice was a low growl in her ear. "Tell me what you are, Maggie."

She hesitated, her mind a jumble of conflicting thoughts. "I... I don't know what you want me to say."

"You know what I want to hear," he replied, his tone insistent.

Maggie's face flushed with humiliation. "I'm a kinky little exhibitionist slut who craves cum. Expose me, use me, fuck me, whatever. Just make it stop."

The lights flickered on, and the two of them pulled away, sitting back in their seats. Maggie quickly pulled her hoodie down to cover herself, her heart racing. She wanted to run, to escape, but her body was too weak, too spent. People began to file out of the lecture hall, giving them odd looks. The professor, oblivious, gathered his things and left without a word.

Maggie was a trembling mess, her body on the verge of another orgasm. "Please, please make it stop," she pleaded.

The girl held out her hand, a silent demand. Maggie, in desperation, pulled her hoodie up and over her head, handing it to her. She looked down at the bump that was her swollen pussy, feeling like she had been inflated to bursting.

"You can't, please don't leave me like this," Maggie tried to project her voice, hoping no one would hear.

"You can do it, come on, but some energy into it," the girl encouraged.

Maggie tried to stand, her legs like jelly, burning with exertion. With all her energy, she heard a loud pop as the suction cup released. On wobbly legs, she made her way to the front, naked and humiliated.

"See, that wasn't so hard," the girl said.

Brian grabbed her by the hips, lifting her up and sitting her hard on the desk on the lecture hall stage. Her feet couldn't reach the ground, and she tried to push herself up with her hands, but her arms were too weak.

"Don't worry, it takes a few minutes to turn off and deflate. Take care of it, or else," the girl said as they both left.

The vibrator turned off, and Maggie heard a slow hissing sound. Maggie's heart pounded in her chest as she sat there, naked and exposed, the monstrous dildo still inside her and locking her to the teacher’s desk. The minutes felt like hours, each second stretching into an eternity of humiliation and fear. She could hear the faint sounds of students in the hall, their voices a distant murmur that seemed to mock her vulnerability.

Finally, the hissing stopped, and the dildo was deflated. Maggie's body, already hypersensitive, shuddered with relief and revulsion as the intruder slowly shrank within her. She gritted her teeth, her hands trembling as she tried to maintain some semblance of dignity. With all her strength, she managed to pull herself off of the dildo and it off the desk, feeling a sickening pop as it finally dislodged from the desk.

She stumbled, her legs weak and unsteady, as she made her way to the door. The hoodie hung innocuously on the door handle, a cruel reminder of her degradation. She glanced through the window, her breath catching in her throat as she saw a group of students walking by. Ducking down, she quickly grabbed the hoodie and pulled it over her head, covering her nakedness.

The dildo, still warm and slick with her juices, she stuffed into the pocket of the hoodie. Her hands shook as she fumbled with the fabric, trying to hide the evidence of her humiliation. She could feel the weight of the dildo pressing against her stomach, a constant reminder of the ordeal she had just endured.

Maggie's mind raced, her thoughts a chaotic mess. She needed to get out of there, to escape the prying eyes and the whispers that would surely follow. She grabbed her things, her movements jerky and frantic, and made her way out of the lecture hall.

As she stepped into the hallway, she kept her head down, her hoodie pulled tight around her. The cool air hit her skin, sending shivers through her. She could feel the eyes of students on her, their curious glances making her skin crawl. She quickened her pace, her legs wobbling with each step, her body still trembling from the aftermath of the ordeal.

She made her way to the nearest bathroom, her heart pounding in her chest. Once inside, she locked the door and leaned against it, her body sliding down to the floor. She pulled the dildo out of her hoodie pocket, her hands trembling as she stared at the object of her humiliation.

"What have I become?" she whispered to herself, her voice breaking.

She couldn't deny the arousal that still lingered within her, the desire that had been ignited by the relentless assault on her body. But with it came a deep sense of shame, a realization of how far she had fallen.

Maggie's mind was a whirlwind of conflicting emotions. She wanted to cry, to scream, to lash out at the world that had reduced her to this. But instead, she took a deep breath, trying to steady herself. She needed to get home, to find some semblance of normalcy, to figure out what to do next.

She stood up, her legs still shaky, and made her way to the sink. She splashed cold water on her face, trying to wash away the remnants of her humiliation. She looked at herself in the mirror, her eyes red and puffy, her face pale and drawn.

"You can do this," she whispered to her reflection. "You have to."

With a final deep breath, she gathered her things and left the bathroom. The walk to her car was a blur, her mind a jumble of thoughts and emotions. She kept her head down on the drive home, she kept her eyes forward, trying to avoid any more unwanted attention.

When she finally reached her apartment, she locked the door behind her and leaned against it, wondering what was going to come next and whether or not she wanted it.

A Walk Through Town Part 10

The next day, Maggie logged into her online class, her stomach churning with anxiety. She had two blackmailers now, not just one. The student remained an enigma, a faceless tormentor she couldn't identify. And then there was her professor, Ms. Sae, who had become another source of her torment. What Maggie didn't know was that Ms. Sae, or Sarah as she preferred to be called, had her own blackmailer: the dean.

As Sarah prepared for her online class, her mind was a whirlwind of thoughts. She knew this class would be different, more intense, and she couldn't shake the feeling of dread that had settled in her chest. She was about to embark on a new, harrowing experience, one that would push her to her limits.

Just as she was about to start the class, the dean entered her office without knocking. His presence was a looming shadow, a reminder of the power he held over her. "I've come to oversee your class in a way," he said, his voice dripping with condescension. His intentions were clear: he wanted to find out what little slut she had in her office hiding before he got there, and to have a little bit of fun with her as well.

"I also thought of a little game," he continued, his eyes glinting with malice. "To keep you in line."

Sarah knew exactly what that meant. It meant something sexual, something degrading. It meant he was going to push her, and she had no choice if she wanted to keep her job and finish her PhD. "Yes, sir," she replied nervously. "What did you have in mind?"

"Well, first of all, strip," he commanded. "And lay out your clothes neatly on the desk."

Sarah's heart raced. "Please, sir, my class starts soon, and I can't give my online class naked. I'll be fired for sure, and my reputation..."

"Your class starts in 20 minutes," he interrupted, his tone icy. "Plenty of time. Please don't lie or back talk me again, Sarah, because for that, there will be a penalty."

She swallowed hard, her hands trembling as she began to comply. She removed her white blouse first, followed by her long skirt. Her bra was next, and as she put an arm over her breasts to cover herself, he stuck out his hand. She handed it over, her cheeks burning with humiliation.

Next, she hooked her fingers into her panties and lowered them to the floor, stepping out of them and reaching down to pick them up. The dean's hand brushed over her bare ass as she did, sending shivers up her spine. She left her heels on, knowing that was probably what he wanted.

He looked over her clothes, his eyes lingering on her exposed body. "Good girl," he said, his voice a low purr. "Now, here’s the game, you may earn back a garment, by making me cum in one of your holes and you can’t do the same hole twice in a row. Let me tell you I may seem old but I can cum multiple times and if I were you, I’d start before your class does or you’ll have to figure out somewhat that they don’t see your nakedness.”

Sarah's eyes widened in shock as she realized she had only 13 minutes left before her class began. Panic surged through her veins as she glanced at the webcam, knowing she couldn't adjust it without drawing attention. With a desperate hunger, she pounced on the dean's pants, her fingers fumbling as she unbuckled, unzipped, and unbuttoned them. She reached for his cock, her hands trembling with urgency, and dropped to her knees.

Her lips wrapped around his shaft, sucking with all the desperation she could muster. The dean chuckled, a low, menacing sound that sent shivers down her spine. "Remember, can't cum in your mouth again. I did that yesterday," he taunted. Sarah moaned in frustration, her eyes watering as she continued to work his cock, her tongue flicking over the sensitive head.

Once he was fully hard, she pulled back, her breath ragged. She stood and bent over her desk, her ass high in the air, looking back at him with pleading eyes. "No, my dear," he responded, his voice dripping with sadistic pleasure. "You have to make me cum, not the other way around." Another sound of frustration escaped her lips. If it wasn't bad enough that he was forcing her to do this, he was also making her take control, making her do all the work.

"Please, have a seat, sir," she said, her voice strained with effort. She guided him to one of the chairs where students usually sat. As he complied, she walked up to him and straddled his lap, her hands gripping his cock. She rubbed the tip along her slit, trying to coax her body into arousal, but the situation was too overwhelming. She was barely wet when she started to lower herself onto his cock, the surprisingly massive dick stretching her beyond anything she had ever experienced.

Halfway down, it started to get easier, not because she was stretching to accommodate his size, but because her body was betraying her, becoming wetter and more aroused. When she finally took him fully inside, it hit spots deep within her that she didn't even know existed, causing her back to arch and moans to escape her lips. "Good girl," he finally spoke, his voice a low, approving growl.

He reached a hand down, his fingers spreading her lips, finding her clit, which was already erect. With the tip of his finger, he grazed over it, and her pussy clenched around his cock, sending a jolt of pleasure through her. She gasped in surprise and delight, her body trembling with the intensity of the sensation.

The clock was ticking, and Sarah knew she had to make him cum quickly. She began to ride him, her hips moving in a desperate rhythm, her hands gripping the chair for support. The dean's hands moved to her breasts, squeezing and pinching her nipples, adding to the overwhelming sensations coursing through her body.

"Faster," he commanded, his voice a low growl. "Make me cum, Sarah."

She obeyed, her movements becoming more frantic, her breath coming in ragged gasps. The chair creaked beneath them, the sound mingling with her moans and the dean's low, satisfied grunts. Her pussy clenched around his cock, her body betraying her with each thrust, each movement bringing her closer to the edge.

"Oh, fuck," she gasped, her voice breaking. "I'm... I'm close..."

"This isn't about you; it's about me," the dean spoke, his voice cold and commanding. "And if you cum without my permission, it'll be another penalty." Sarah's teeth ground together in frustration. He was in control, and she couldn't even enjoy the pleasure of it. She was just a pawn in his twisted game.

"Yes, Sir," she replied through gritted teeth, her voice trembling with a mix of fear and arousal. She continued to ride him, her hips moving with a desperate, frantic rhythm. She clenched her pussy around his cock, trying to milk it for all it was worth, but that only added to the overwhelming sensations coursing through her body. The fear of punishment was a constant, gnawing dread in the back of her mind.

It was hard to gauge how close he was. His eyes remained calm, unreadable, as she stared into them, her own gaze filled with a mixture of desperation and desire. He was keeping such a composed demeanor that it worried her. She feared she wouldn't make him cum in time.

"You only have five minutes left before your class, Sarah," he reminded her, his words sending a jolt of fear down her spine. The thought of teaching her class naked, trying to conceal her state from their prying eyes, was almost too much to bear. She clenched around his cock even tighter, her body trembling with the effort.

She bit her lip, her eyes locking onto his with a look of pure, unadulterated desire. "Please, Sir," she begged quietly, her voice barely above a whisper, hoping no one outside her office would hear. "Please..."

The situation was a double-edged sword, driving her body to the brink of madness. She had to hold off her own orgasm while simultaneously bringing him to the edge. It was a delicate, maddening balance.

Without warning, not a gasp, not a drop of sweat, he began to cum inside her. The sudden, intense sensation drove her over the edge, sending her into a mind-numbing orgasm. Her body convulsed around his cock, her moans muffled by the desperate need to stay quiet. The pleasure was overwhelming, a tidal wave of sensation that left her gasping for breath, her body trembling uncontrollably.

As the waves of pleasure subsided, she collapsed against him, her body spent and trembling. The dean's calm demeanor remained unchanged, a stark contrast to her own state of utter exhaustion and vulnerability. She knew she had to get up, to compose herself before her class began, but for a moment, all she could do was cling to him, her body still reeling from the intensity of the experience.

"You came, didn't you, Ms. Sae?" The dean's voice was stern, almost parental, as he addressed her. She sat up straight, feeling like a child caught in a misdeed, rather than an employee being reprimanded by her boss.

"Yes, Sir," she replied, her eyes cast downward, her voice barely above a whisper. She felt the weight of his gaze, the authority in his words pressing down on her like a physical force.

"Please hand over your panties," he instructed, his tone leaving no room for argument. "You know you did something wrong."

She got up on wobbly legs, his cock slowly withdrawing from her as she stood. It felt like she was pulling herself off a metal rod, the hardness of his member still pressing against her sensitive flesh. She made her way to her desk, her movements unsteady, and grabbed her panties, holding them out for him.

"Ok, now get dressed," he said, his voice cutting through the air like a whip. "You have your class to teach."

She reached for her skirt, her hands trembling slightly. "You only made me cum once," he reminded her, his words sending a shiver down her spine. "So I would choose wisely which you get to put on, since you don't get both."

She bit her lip in worry, nearly drawing blood. The skirt wasn't going to cover much, but the blouse was a little sheer without her white bra. She had no other choice. Quickly, she put it on, sitting at her desk, bottomless, her skin against the cool fabric of her chair. Her body was still sensitive from riding the dean, his cum dripping out of her pussy, a constant reminder of the encounter.

The dean walked up to her just before her stream was about to start. He unbuttoned two buttons on her blouse, exposing the tops of her cleavage. Before she could protest, she was on screen, her class watching her. The shock of it all made her heart race, her face flushing with embarrassment as she tried to maintain some semblance of composure.

"Good morning, class," she began, her voice steady despite the turmoil inside her. She could feel the dean's eyes on her, the weight of his presence a constant reminder of her vulnerability. She knew she had to get through this, to maintain her professionalism, but the memory of his cock inside her, the intensity of their encounter, was never far from her mind.

As the class progressed, no one would have suspected anything was amiss. If her students had actually paid attention, they might have noticed the state of her dress, the pale tops of her bare breasts that had never seen the light before peeking out from above her blouse, the faint darkness of her nipples through the fabric. She wasn’t sure if she was more disappointed or relieved by their lack of attention. She watched Maggie’s webcam and saw, for once, nothing was out of the ordinary, and maybe she had learned her lesson.

"Ok, let’s start with the PowerPoint part," she spoke up, pulling it to full screen. The relief that the webcam was no longer watching her was short-lived as the dean walked up next to her, his cock rubbing up against her cheek. She muted her mic for a second, and asked, "Sir?"

"You still need to earn back your skirt, little girl," he replied, his voice low and menacing. "And you have till the end of your class to do so."

Her eyes widened; he couldn’t be serious, not in front of her students, even if they couldn’t see her. This was just too much. She opened her mouth to say something, but he traced her lips with the tip of his cock. Her scent and his all over his cock, the taste of both of them and his cum lingering on her lips as a drop of precum was rubbed across her mouth. He reached down and clicked the mouse button, unmuting her. She pulled back and began talking about the PowerPoint, he wrapped her hand around his cock and made her stroke it as she taught.

It was almost comical as she tried to teach, hidden by her PowerPoint, switching between stroking his cock and sucking on it, licking it while talking at the same time. At one point, he grabbed the back of her head and shoved his cock down her throat, causing her to cough and gag. The sound must have been horrible through her mic, and she prayed no one knew what it was. There was no way she was going to make him cum while teaching at the same time, and they both knew that. He went behind her, standing her up and bending her over.

But she knew the rules: no cumming in the same hole twice would work. That’s when she felt the tip press against her virgin asshole and panicked. The sensation was overwhelming, a mix of pain and pleasure as he slowly pushed inside. She bit her lip, trying to stifle her cries, but the sound of her muffled moans filled the office just before she muted her mic. She could feel his cock stretching her, filling her in a way that was both terrifying and exhilarating.

"You still have a class to teach, Ms. Sae," the dean reminded her as he continued to fill her ass with his massive cock. He reached forward and clicked her mouse again, unmuting her mic. The look of panic and pleading filled her eyes as she looked back at him, her teeth biting into her lips, mixing in her unmistakable desire. As she read, there were brief pauses, some may have thought a bad connection if they were paying attention, but a noticeable gasp did escape her lips when she finally bottomed out on his cock. His cock was fully in her ass now, while she was teaching her class on her webcam with all of her students online with her.

She bit her lip as he began to pull out and took considerable concentration to continue as he made his way back in. She felt like he was going to turn her ass inside out until at one point she realized, she was not getting pulled back with him as he was now easily sliding in and out of her with no resistance. The pain was gone and now it was the pleasure she was trying hard to fight back on expressing. In and out he went, with no regard for her trying to keep a straight face or speaking her lesson, he had one thing in mind at this moment and it was to fill her ass with his cum.

With 20 slides to go though he had to do it fast or else go back to the cam for all to see. She stalled the best she could but the countdown began and her anxiety of being seen, bent over, being fucked from behind by an anonymous man with an obvious view down her blouse of her braless breasts. With 8 slides to go she felt his movements begin to become erratic, his breath quickening a huge contrast to when she rode him and he made no reaction. 5 slides his cock started to throb inside of her and at 2 she felt him start to fill her, his fingers digging painfully into her hips as he thrust himself completely into her and came.

Pump after pump after pump of his cum filled her, she had no idea where it was all coming from or if it was all in her mind. As she was at her last slide, he pulled out of her, and she felt her asshole gaping, his cum spilling out of her, but she had no time to deal with it. She quickly sat down and fixed her blouse the best she could, the only thing covering her, and switched back to her webcam. Her face was flushed red, her hair slightly disheveled, she could feel the dean’s cum leaking out of her pussy and ass onto her chair. She quickly summarized her lesson, spoke the homework and the lesson for next week, and watched as her students slowly logged off one by one, all except Maggie.

Maggie's face was as red as hers, she looked like she was breathing heavily, and Sarah knew, they both knew, as they both looked into their cameras at each other. Maggie knew what she was doing, and Sarah knew Maggie was still doing it. The dean gave a quick glimpse out of camera view, seeing the name of the last student in the class, Maggie Hill. He knew what his next conquest was going to be. Without a word, he left Sarah in her office and made his way to his to find out more about Ms. Hill.

A Walk Through Town Part 10.5

Now while Sarah was busy with her ordeal, she didn’t know Maggie was dealing with her own. Maggie was just wearing an old running shirt and some soft shorts, she had a sickening suspicion they were going to end up on the floor anyways, and she was right. A text message came in, startling her out of her half-awake state.

"You’re overdressed," it read, and she knew what that meant.

She stripped off her shorts and ducked down to remove her shirt. Half-awake, when she sat back up, it took her a second to realize her breasts were on full display before she moved her camera up slightly and sat lower in her chair.

"LOL" was the next text she got, and she was certain why, hoping no one else had seen.

She thought Ms. Sae would have noticed, but watching her do her lesson, it seemed she was preoccupied with other things, and she wrote it off as she was probably just busy focusing on teaching, which gave her a little relief.

"There’s a package at the door for you," another text appeared, "go get it."

She ducked out of sight with her phone and went to her front door, she opened it and carefully looked outside, still naked, and saw a small brown box waiting for her. She brought it in and opened it, finding a weird pink device and instructions. It took her minutes to set it up and connect and went back to her room, slipping back into her seat without showing anything off. "

Put it in," the text message instructed.

"Put it in where?" she responded.

"You know where, that needy pussy of yours," the text read.

She gasped and put a hand over her mouth and looked at it now knowing what it was. She pressed the large egg-looking end into herself, it was big and thick, and with how tight she was and not so wet, it was a little hard, the tail end was left outside of her pussy.

"Now go into the app and click accept," she did what she was told, and the device buzzed twice inside of her nearly making her moan.

Then it came to life with a soft vibration, stirring her up and starting the burning arousal she had come so used to and craved.

“Oh, it looks like I have a little treat for you,” the next text read.

Maggie responded back, "What, a vibrator for my ass too?”

“Maybe next time if that’s what you really want," another text, "no, right-click on the teacher’s webcam and click switch input to her webcam.”

Maggie blushed at the thought of him making her put something in her ass, but did as she was told and was filled with a huge surprise as the webcam switched with the presentation. Her teacher, Ms. Sae, was servicing some random cock while she was teaching. She watched as she didn’t know how to react or take it as she watched her jack off and suck on this massive cock.

“Who knew the teacher was such a slut too, maybe whatever you have is contagious and turns all innocent girls into sluts,” the next text read.

She should have been mad or embarrassed, but it didn’t register in the face of what she was watching. The vibrations grew stronger as she continued, she bit her lip knowing she probably wasn’t allowed to mute her mic as she watched, but between the new toy inside her being controlled by some faceless person and watching her teacher, it was hard to keep her arousal in check.

When she thought it couldn’t get any more intense, she watched as her teacher stood, and saw she was only wearing her white blouse and then as she bent over, saw she was braless and her bare breasts on cam and the look on her face as she was obviously being taken by this anonymous man. She was so confused why she would do this, why she would take the risk and if it really was her fault, all the time the vibrator slowly got stronger and stronger as Maggie slowly lost all thought of where she was and what she was doing.

All she could manage to think about was her teacher being fucked from behind and how turned on it made her as she secretly watched. She started to rub her clit and grope her breasts. Her first orgasm quickly hit her, hard, and as she watched, it seemed to just continue and continue like it would never stop as her teacher’s fucking seemed to get harder and faster from behind her.

She wasn’t even sure when she stopped lecturing, just watching her teacher fix her blouse and sit back down fixing herself as she finished her class and after everyone logged off, they both watched each other knowing in a way what just happened.