Through Heaven and Hell

But selfish motives aside, it evidently did the trick. "They pick on me because I look like a girl..." he finally mustered.

Scarlet blinked in disbelief. "What? Seriously?"

"Yes... That's what they tell me at least."

"... How long has this been going on?" Scarlet asked pressingly, forgetting her previous, calm tone.

"Since... since when I enrolled..." Daniel mumbled, before finally failing to hold it any longer. His tears burst out like from a broken dam, and his sniffling turned into sobbing as his face distorted into pure despair.

"Oh, sweetie..." was all Scarlet could think of in response. She grabbed the back of the boy's head with both hands and pressed him against her large, soft chest, this time genuinely wanting to console him without any indecent thoughts. That is, until Daniel suddenly reached around her, grabbing her in a tight hug as his tears continued to gush out between her tits. The fruity, feminine scent of his shampoo was an absolute delight to breathe in, like sniffing freshly bloomed flowers during spring, only much, much sweeter. "There, there..." Scarlet comforted, noting that the timid little tomgirl seemed to calm down rather quickly as she held him tight. "It's gonna be alright."

Time and time again, she found herself unable to rid herself of the lewd thoughts she was having, knowing damn well how despicable it was. This was one of her students, for God's sake. Bawling his eyes out right in her bosom, finally comfortable with sharing what he has been through, and the most pressing thing on the lecherous woman's mind was howfucking hot he was.

Then it hit her. Perhaps that was just the thing he needed to hear?

"You know what I think, Daniel?"

He looked up at her, his face even move attractive when covered in tears. "... What?"

"I think those girls are jealous. Jealous over how pretty you are, despite being a boy. They know they will never have your looks, so they take out their frustration on you, because that's the only thing that brings them comfort."

With doe-eyes, Daniel just silently stared at her for a moment. "You... think I'm pretty?" he asked meekly.

"Of course I do," Scarlet assured him. "Have you seen yourself in the mirror? You're prettier than any girl out there. At least out of any I've seen." She knew she shouldn't be saying all this, not to a student. But she couldn't stop herself. Heneeded to know.

Blushing crimson in embarrassment, yet looking somehow disappointed, Daniel turned away from her. "You're just saying that to make me feel good..."

"Are you kidding me? How can you not see how hot you are?"Stop, she thought to herself. "I'd date you in a heartbeat if I weren't your dean."Seriously, stop. "Just look what you did to me!"For fuck's sake, Scarlet...

There was no denying it now. By shamelessly grabbing the bulge in her crotch, she had definitely gone too far. But seeing the shocked expression on Daniel's face made it well worth it. That is, assuming he wasn't going to run away in fear. Thankfully, that ended up not being the case.

"You... you have a..." he merely stuttered, his still teary eyes fixated on the intimidating display.

"A cock. That's right, Daniel. I have a big, fat cock." Never had she been so comfortable with revealing her secret, but there was just something about her adorable little student that made it feel so right. As if he was just what she had been looking for all along. "When I see cute boys like you, the only thing I can think of is how much I wanna touch them, taste them...fuck them..."

A shudder went through Daniel's body as he registered what the dean had just said.Fuck them? he thought.She wants to... have sex with me? He couldn't take his eyes off the dean's thick meat, its outline obscenely visible through the fabric as she held it in a tight grip, while Daniel's agape mouth went dry as he stared at it. His crying seemed like a distant memory, replaced with something else, something that was hard to place, but his sudden composure was undeniable.

Despite what one might expect, including Scarlet, Daniel wasn't frightened or grossed out in the slightest. Quite the contrary, in fact. He might have been a timid little thing, but just like everyone else he had sexual fantasies, and this was a fantasy come true. One look at him was enough for anyone to understand that he wasn't exactly going to be a top in bed, and just like his feminine exterior, his interests were unsurprisingly more akin to a girl as well. And the dean was beautiful and kind-hearted, so what did he have to be afraid of?

He gulped, swallowing any feelings of doubt that might have stood in between him and his desire. "Can I... touch it?"

Scarlet stared at him blankly. "... You want to?"

"Yeah..." he murmured, biting his lip and staring back into the redheaded woman's bright blue eyes. "I'm the one who made you hard, so maybe I could be the one to... fix it?"

"Oh my, Daniel," Scarlet said teasingly, running her hand through the boy's shiny hair. "I didn't take you for a pervert."

"Is that a yes?" he asked impatiently, his face lit up in sudden excitement.

"Well, I wouldn't mind... But don't you want to do more than just touch it?" A smirk spread across her face as she looked down at the suddenly dumbfounded boy, her hand continuing to massage his scalp the entire time. While awaiting an answer, she used her free hand to let her aching cock out of their tight enclosure. Just as she pulled her skirt down and revealed it for little Daniel to lay his eyes upon, it instantly sprung out in all its glory, at full mast and throbbing hard.

Daniel's eyes went wide. Was that thing even real? It was bigger than any penis he had ever seen, in real life or otherwise. It was as pale as the rest of her skin, but with intimidating, pulsating veins all over it, and while her big balls resting below it looked smooth and hairless, her mons was covered in a thick bush of coarse hair, its red color just as full and gorgeous as on her head.

In his pants, Daniel could feel his own far smaller member stiffening, and somehow, the knowledge that he was completely outclassed made the whole situation all the more hotter to him.God, that huge thing looked so fucking...delicious. That's the only word he could think of that accurately described how he felt about it. Seeing that little drop of precum running down the thick, bright-pink mushroom head was almost too much.

"I want your pretty little lips around it, Daniel," Scarlet purred, wagging her stiff cock back and forth with a hand around its base. "Can you make that happen?"

Daniel's face lit up anew. "Yes! Yes, absolutely!" he exclaimed, showing Scarlet how pretty his face looked with a smile on it for the first time. And without further ado, he stood up, then quickly knelt down on the floor in between the dean's smooth, pale legs. As soon as he had gotten into position, he immediately went to work, starting off by grabbing her thick length with one hand, while the other reached under her fat balls, cupping their underside with the palm of his hand as his thumb gently massaged their frontside.

A mere moment later, and just as eagerly, he leaned forward, practically going cross-eyed as the thick meat-rod filled his vision. He gave the tip a light kiss, smearing his lips with Scarlet's sweet, sticky precum, giving them a lick just to savor the taste. Wanting more, he began licking the little slit, drawing out a few more drops across his tongue, then circling the head in its entirety, coating it in his warm saliva.

"Mm... good start, Daniel," Scarlet moaned from above, petting the boy's head as an indication to keep it up. "Now take it in your mouth, will you?"

Hearing the goddess of a woman telling him what to do sent shivers down Daniel's spine. It just felt soright. Just like she had instructed, he wasted no time in wrapping his lips around the glans, the sheer size of it almost filling up his mouth, leaving no room to keep running his tongue around it. Instead, he began slowly moving his head back and forth, smearing his lips against the smooth, spongy flesh of her head, from rim to tip. His tongue returned to licking her slit, eager to extract more of her sweet, viscous pre-ejaculate.

"Look at me, sweetie. I wanna see those pretty eyes."

With a face flushed with lust, Daniel looked up, locking eyes with the dean as he continued to slather the head of her cock. Seeing the arousal on her face made his heart flutter, knowing that he was the one who had brought her into that state. Biting her lip, smiling slightly, cheeks with a hint of red from excitement... It was the type of beauty that would make one think they died and went to heaven.

Fueled by the visual stimulation, he decided to go further. Instead of stopping at the rim of her glans, he pressed on, filling his entire mouth with the monstrous cock, stopping only when it hit the back of his throat. Judging by the moans coming from above, his efforts did not disappoint. He kept going at it, quickening his pace, bobbing his head back and forth, his cheeks sucked in from the intense power with which he was blowing her.

Scarlet moaned in pleasure, leaning her head back and draping her arms over the back of the couch, feeling like she was on top of the world. Daniel was surprisingly good at sucking cock, though she doubted that he had ever done it before. Perhaps with dildos, but probably not a real one, shy as he was. Not that it was anything worth dwelling over when having a sexy little girly boy filling his mouth with her thick meat, of course. Truth be told it was hard to think at all with the jolts of pleasure going through her body every time he licked the tip or sank her length deep into his mouth.

But there was one thing on her mind that needed addressing: Why should she be the only one getting pleasured?

"Stop for a second, Daniel," she said, putting her hand on his forehead to push him back slightly.

"... Did I do something wrong?" he said in a defeated tone, with a string of saliva connecting his lips to Scarlet's cock.

"Of course not sweetie." She gave him a warm smile and gently patted him on the cheek. "But I want more. Like I said when it comes to boys like you... I wannataste them."

Daniel stared into her crystal eyes, confusion evident on his face. "Taste how?"

Her warm smile turned to something else, something a bit more... sinister. "Take off your shorts and underwear, and I'll show you."

Under any other circumstances, hearing a woman say such a thing would've rendered him paralyzed from embarrassment, but now, there was only one thing on his mind: To continue what he had started. He wasted no time in doing as he was told, hooking his thumbs under the hem of his shorts and pulling them down, revealing his tighty whities that only bulged ever so slightly, in contrast to what Scarlet was packing. But just as he was about to pull them down as well, he hesitated.

"What's wrong?" Scarlet teased, a wide grin on her face as she watched the boy's face turn red. Well, redder than before, that is.

"I've... never showed myself to anyone..."

Scarlet swooned over how pure he was, feeling her cock get even harder at the thought of showing him his true calling. "Don't be embarrassed," she said, grabbing him by the shoulders. "You're literally the prettiest thing I've ever seen, Daniel. But you have to learn to be comfortable in your own body. So if you undress, Ipromise that you won't regret it."

He glanced at her again, before turning his head away with a sigh. "O-okay..."

"Good boy..."

After another moment of silence, Scarlet watched in awe as the cute little girly-boy finally went all the way. He had turned away from her, presumably in embarrassment regarding his size, but she wasn't complaining at all, as it meant that she got the best possible view she could ask for. It was almost as if time slowed down watching his underwear slide down his smooth, slender legs, revealing his perfect little bubble butt to her. Just seeing it in front of her was enough to almost have her drooling. It looked so smooth, so round, so soft... sotasty.

His underwear had barely had time to fall to the floor before Scarlet spoke up, while lying down on the couch in preparation for what she had planned. "Come here, Daniel. I want your ass on my face,now."

"Y-your face?" Daniel stammered, looking over his shoulder at Scarlet as she stroked her huge cock.

"How else am I supposed to taste you?" she said with a sly grin and ran her wet tongue over her lips, while beckoning him over with her index finger.

Daniel stayed silent, feeling a bit taken aback by how dirty Scarlet's mind was. But he wasn't disappointed. In truth, he was becoming rather excited. It's as if she was treating him like a girl, focusing on his ass rather than his penis. And that was exactly what he wanted. What he had fantasized about ever since he hit puberty.

With a newfound sense of confidence, he quickly turned around, presenting his front to Scarlet and walking over to her, his previous hesitation being all but evaporated. Despite his rather small manhood being on full display, he didn't really care anymore. Because he knew what she was truly after. His penis was never going to be the star of the show, not with the beautiful redhead's massive size dwarfing his own.

But despite its insignificant size, Scarlet definitely appreciated the view, perhapsbecause of how small it was. Paired with his girly features it almost looked more like a clitoris than a penis, but knowing that it wasn't made it so damn hot for some reason. Daniel's entire being seemed to reject the idea of being a boy, and Scarlet was happy to take him further along that path.

"Get to it already," she prodded playfully, resting her head on the couch's armrest.

"Yes, sorry," the boy replied, his face red with lust as he climbed on top of her. With both feet on either side of Scarlet and his bubble-butt directly above her face, he looked back at her. "Like this?"

Scarlet put on a face that screamed of satisfaction. "Like that. Now sit down. And keep sucking my cock."

Here it goes, Daniel thought, taking a big gulp and finally sitting down on top of Scarlet's face. He barely had any time to register the severity of the situation - that he was about to let hisdean give him a rimjob - before he felt her wet tongue slide through his asscrack. Shivers went through his entire body, for a moment causing him to forget his task at hand. When he suddenly felt her grab his cheeks and separate them, followed by a barrage of licks directly onto his little butthole, a whimper escaped his lips as he started spasming in pleasure. But even so, he knew he had a job to do. He took a deep breath and lay down on top of her, putting his face right above her intimidating cock. After giving it a quick appreciative glance, he resumed where he left off, instantly filling up his mouth with several thick inches.

Scarlet entered a near hypnotic state as she continued to coat the puckered, pink hole with her drool, feeling its wrinkly texture on her tongue and the contraction around it each time she tried to push it deeper. Throughout her entire life, she had never had the opportunity to do this kind of thing. Despite talking about it as if she were an expert, this was her first time giving a rimjob, and it was everything she had dreamed about and more. The fruity taste and smell of a cute boy who evidently went to great lengths to not only look like a girl, but to smell like one too. All the while being stimulated by his eager mouth, slurping away at her cock like there was no tomorrow.

But as enjoyable as it was, it couldn't last any longer. This was only meant as a preparation. Scarlet wanted to enjoy Daniel's body to the fullest, and it was high time to proceed to the next step.

"You're ready," Scarlet stated coldly after having ended her enthusiastic licking.

Daniel popped her cock out of her mouth and turned around to look at her as best he could. "Huh?"

"I want you to lie down on your back," she said, pushing him off of her and sliding her legs off the couch, after which she grabbed him by the shoulders and held him close enough for him to feel her breath in his ear, letting her voice come out in a soft, seductive whisper: "So that I can fuck your tight little ass. Fill you up with my seed... How do you feel about that?"

A blissful smile spread across Daniel's flushed face, merely from hearing her sweet, angelic whisper. "I was waiting for you to say that..." he mumbled, already busy getting into position on the couch.

Scarlet went quiet for a second, then let out a satisfied giggle. Although not what she had expected, she got the best response she could have wished for. She eyed him as he wordlessly lay down, resting his head on the opposite armrest and putting his entire front on display. It took all the mental power she possessed not to jump him right then and there, just from seeing his sexy body right in front of her. Thin, yet curvy where it mattered, and with skin as smooth as silk.

As calmly as she could, she took off her suit jacket and hung it on the side of the couch, then began unbuttoning her white shirt underneath. She was becoming increasingly impatient with each second that passed, her fingers struggling to properly fit the buttons through the holes, made even harder by the fact that she had a sexy little twink staring her down with bedroom eyes.

Fuck it, she thought, grabbing each edge of the shirt's placket and ripping it apart, sending the remaining buttons flying. She wasted no time moving on to her bra, which, thankfully, was a front-close one, and quickly undid it, finally revealing her second most defining asset, the first being her cock, of course. Her eyes were locked onto Daniel's, who in turn had his glued to the now-revealed chest of the sexy dean. She smirked, knowing damn well how perfect her tits were, perky and round, slightly freckled, and just as pale and rosy as the rest of her. But for now, they were only eye-candy for him. She was longing for release.

Like a predator, she suddenly pounced on top of the little boy and boxed him in with her arms around his, drawing out a surprised yelp from him. "Are you ready?" she asked, breathing heavily right onto his face while her rock-hard cock bobbed up and down between his spread legs, making her big ballsack swing back and forth.

"Yeah, I... ah!" The feeling of something huge, bigger than he remembered it being just a moment ago, pressing against his tight hole suddenly hit him. He looked down, seeing the fat, pale cock lodged between his cheeks, thinking that there was no way he was making it out of this unscathed. Furthermore, it only now dawned on him that Scarlet was about to fuck him with only spit as lube. And for some reason it was making him... really horny, pain be damned.

"F-fuck me, please..." he begged, staring deep into her eyes.

"I love it when you beg, baby..."

At last, there was nothing to hold her back. She flexed her buttocks, slowly pushing her tip into Daniel's pink little boyhole, as he moaned and writhed in what could only be a mix of pleasure and pain. Scarlet pushed on, closing her eyes and biting her lip in pleasure as his warm insides hugged her thick shaft, slowly swallowing up every inch of her.

"God fucking damnit, you're tight!" she hissed between her teeth, just as the vise-like grip of his ring gave way for her full length, ending up pushed firmly against her mound, covered in her coarse, ginger hair. She held it there for a moment of pure bliss, the entire surface area squeezed by Daniel's virgin hole. Just as slowly as she had pushed it in, she pulled back until roughly half of her cock remained inside him, then thrusted again, faster and harder this time, surely causing a great deal of pain to the poor boy, but in the moment only caring about the mounting pleasure that rocked her body. She was far too into it to even notice any noise coming from him anyway.