Ch. 21 – The Flip Side (Part 2)
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“Oh? What other tricks do you have?” he moaned, hypnotized by the show. 

 “I just want you to understand how such details feel from a woman’s perspective, so you can make more educated choices in your future,” she purred, looking down on him imperiously enough that he could feel the weight of her gaze through the opaque veil. 

Her words tumbled in his mind, but he couldn’t quite grasp them. Instead, they slipped out of his mental grasp time and again. Though each word made sense on its own, they simply didn’t make any sense when they were put together like that. Feeling from a woman’s perspective? Even as he tried to understand, his body began to feel very strange, like things were shifting in a way that they shouldn’t beneath the thin surface of his skin.  

“Wait, what?” Matthew asked. That was all he had time to get out, though, because suddenly, the exquisite sensations he felt mutated and amplified. For a moment, he thought she’d made his dick huge again, but a quick check showed the same size dick was sliding in and out of her as before. 

If it was the same dick, then how could it be feeling this different, though. The pleasure wasn’t even coming from his dick now but from somewhere further up near where his shaft met his body. It was like the pelvis was suddenly an erogenous zone or something. It was only after giving that thought a little more scrutiny that he peered closer and discovered that he wasn’t quite seeing what he’d thought he was seeing. There was still a dick that was connecting them, of course, but it wasn’t disappearing in and out of his partner. Instead, it seemed to be attached to her and was disappearing in and out of…

Matthew’s mind had trouble allowing him to complete the thought, and for several seconds he lay there in denial. In the end, it was only the rising pleasure that was building in him in an unfamiliar way that allowed him to finally break free from his mental paralysis. 

“W-wait, are you fucking me?” he asked with a trembling voice, afraid of how she was going to answer. 

“I am, master,” she panted, not slowing down as she spoke, “I’m fucking your pretty new pussy with your own dick. How does it feel?”

“Like we should stop,” he groaned, afraid of how good it felt and how fast that pleasure was building deep inside of him in a part of his body that shouldn’t even exist.  

“Shhhh…” she answered, not stopping her rocking. “We will in a moment, Master. I just want you to understand, really understand, what you’re doing to these women in your life.” 

Matthew had no idea what it was that pushed him over the edge, but whether it was the taboo nature of the experience or the way she was in complete control, he came hard in a way that was utterly unlike every other experience in his life. It wasn’t necessarily better than cumming deep inside Mrs. Hale’s pussy, or all over Mrs. Laurens’ amazing tits, but it was intense enough to short-circuit his brain and force his hips to rise up to meet her, which triggered another small fireworks show inside his reeling body. 

“Ooooo-okay, I get it, we can stop now and—” Matthew moaned, even more overwhelmed by the experience than he was weirded out by it. 

“Soon,” she purred. “So far, you’ve only cum from your old cock. To really understand, you have to feel what your teacher felt, Master.” Even though she used the word, Master, Matthew did not feel very in control at the moment. He didn’t feel like he could stop this now if he wanted to, but he wasn’t really sure that he wanted to. After all, no matter how strange it was, this was a once-in-a-lifetime experience. Without a magic book and a strange sex spirit, he would never be able to experience something like this as a man. 

He tried to hold on to that thought as he felt the cock stretching him out start to grow slowly. At first, Matthew noticed the girth more than anything and the way it stretched out his tight little hole, but after a few inches had been added, he noticed that it changed everything. It wasn’t just that the strokes were longer, either. It was that they reached deeper inside of him to places that he could barely imagine. He had a series of small orgasms to this thought as he tried to imagine where eight inches of dick could even fit inside his body. Whether it felt better or not wasn’t even a comparison worth making. There was no doubt that white-hot bliss coursed through him down to his toes and felt better than it had the first time. 

Somewhere past nine inches, it started to hurt, and he whimpered at the feeling. Each time Tomé’s dick bottomed out inside him, it slammed against some tender barrier, sending a jolt of pain through him alongside the overwhelming pleasure. For the first couple of strokes, it was a distraction at best and something that urged him to reconsider what he was doing. After half a dozen long slick strokes, the pain blended into the pleasure, becoming one more layer in the symphony of sensations that were assaulting his body in ways he could never have imagined before now. 

“I never knew it could feel like this,” Matthew groaned. “It hurts, Tomé.”

“It does,” she agreed, “but you love it, just like your teacher loved the way you hurt her, but you need more to really understand how you made her feel, don’t you?”

“Yessss…” Matthew hissed, despite his better judgment. He’d gone far enough, and he’d cum hard enough. Somehow he knew that more wasn’t necessarily good for his mental well-being, but he was too far gone for that now. “Fuck me, Tomé. Fuck me harder.”

As her cock got longer and thicker, he thought that he was going to die. Each thrust felt like it was never going to end, and when it did, it was a tectonic sensation that drove the air from his lungs, and all he could do was lay there and endure it. He couldn’t stop cumming now. His body was completely lost to the pleasure of the moment, and that pleasure seared his mind away an inch at a time. 

“Your pussy is really tightening up, Matthew,” Tomé teased. “If you keep it up, I won’t be able to hold back much longer. Then you’ll finally know how good it feels when someone cums inside you.”

Matthew’s mind boggled at the idea. It was such an unnatural thing that he couldn’t even think about how to respond. Instead, his head lulled to the side, and his detached mind fixated on the view of his masturbating teacher. 

There she was, hiding away from her husband while she relived the brief moment that they’d shared, and the whole time she was making herself cum in a desperate attempt to reclaim a portion of that pleasure, she was moaning his name. Would he end up the same way, he wondered? He’d thought that getting to fuck his dream girls had been the best feeling in the world, but if they felt like this while he was doing it, then he was getting the short end of the stick. 

He might have despaired about it, but despair was impossible right now. Instead, all he could do was lay there and moan while Tomé showed him secrets that man was not meant to know. 

“Here it comes, my master,” she whispered, unable to hold back any longer. 

When her impossible cock finally erupted inside of him, he felt warmth flood his core immediately, adding another layer of complexity to the pleasure that had consumed him and triggering another orgasm so strong that he felt himself starting to lose consciousness in the face of the impossible undertow dragging him down. 

At that moment, he could feel everything. The way that her cock was so thick it was painfully stretching his pussy lips. The way that she was grinding her dick against his womb. The way each fresh burst of cum made the shaft pulse and spasm deliciously inside him. All of those things were nothing more than notes in the symphony that assaulted him, and he could only concentrate on each for a moment before the next one stole his attention away. In the end, all he wanted was to get lost in this and never wake up again, but finally, the darkness took everything, and his dream fell apart in a storm of images and disconnected thoughts. 

“What a pretty little woman you would make,” Tomé murmured in his ear as the dream dissolved around him. “Maybe we’ll go even further next time.”

Matthew had no idea how he would have responded to such a terrifyingly tempting offer even if he could have, but fortunately, the darkness finally claimed even those thoughts, and sleep took him before he could do any more damage to his psyche.

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