The Most Magical Night of My Life

by anonpencil

Strangers In The Night

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At first, Cranky was sure he’d done the absolutely most foolish thing of his life. He’d always been clever in his own way, but he’d never done anything quite so brash, so daring. Maybe he should have asked her more clearly if this was okay, let her make the first move, or let the moment pass altogether. It was too strange of him, she’d hate him, surely this was a mistake! Then he’d felt the press of her hoof against his chest, and felt her body lean against him, and he knew that he was wrong. This was the least foolish thing he’d ever done.

Matilda’s lips were soft and cool, and there was a sweetness that met his tongue as she pressed against him more firmly. He had initiated the kiss, but now he felt her lean into it hard, and he felt a little squealing murmur of pleasure against his mouth. It was surprising enough that his eyes flickered open for an instant, and he saw that she was smiling widely, eyes shut, an expression of bliss filling her every feature. He quickly shut his eyes again, wanting just to focus on the sensation of their lips joined together, to forget the world around them entirely.

He pulled her close, his hooves finding their way around the back of her head into her mane, the other to the back of her neck. He held her in his grasp, and it felt like he was holding actual magic there, that it might dissipate at any moment.

Far too soon, he felt her pull back. His eyes again opened, and he studied her face to see if she was angry or disappointed. To his great relief, her blissful smile had never wavered.

“I… see” she said, her voice sweet and trembling. “I’d wondered if you wanted to do that. Hoped you did.”

“Since the moment I saw you.”

He hardly recognized his own voice. She giggled, and he could practically taste her laughter on his lips.

“I told you that you were a charmer.”

“And you’re enchanting. Beautiful. Otherworldly.”

“Oh hush, you’re saying too much.”

“Then stop me.”

She did, in exactly the way he’d hoped. Matilda leaned forward and fixed him with another kiss, again leaning her full weight against him. This time, however, her lips were warm, as if their kiss was heating up her entire body. He allowed his instincts to take over somewhat, and his mouth opened so that their tongues could meet. She reciprocated in kind, and he again felt a rumble of sound from her, this one lower and less squealing. It wasn’t one of excitement, but one he recognized as intoxication. He was no longer the only one drunk on their interactions.

Cranky’s hooves ran down her head and neck to her shoulders, feeling the silkiness of her neckerchief under his touch, the way her coat felt even more silky than that. He felt a shiver run through her body as his hooves moved, and this time the sound that passed between their united lips came from him. She felt fragile, like he could break her in an instant, but also so alive, a being of pure energy. It was terrifying and intriguing all at once. He felt unworthy of her. He didn’t care.

He pulled his head back briefly to gasp in the cold air of the dark palace room, and it tasted bitter in comparison to her. The air felt less needed than her at that moment, and he plunged back into another kiss with abandon, his hooves beginning to move over her neck and shoulders under their own guidance. Her hooves slid up his chest to his neck, and he felt a caress down the side of his face, one of the most intimate sensations he’d ever experienced. He didn’t want it to stop, nothing could possibly be better than this.

She gave another wilting-sounding sigh against his lips, and drew her head away from him to look up into his face. The two studied each other, and Cranky could feel a silent conversation taking place. Where is this going? Do I stop? Do I tell you to stop? Is this what you want? Is this what I want?

“I…” he managed to say, his voice trembling, but there were no other words for him to use.

Matilda’s large blue eyes passed over his face as his mouth moved wordlessly, and then she smiled ever so gently, and held a hoof to his lips to still them. She looked as though she might cry, might laugh, might faint, Cranky just couldn’t be sure. At last, she spoke.

“Don’t overthink this,” she murmured. “It feels right to me too. Where’s your sense of adventure?”

It was exactly the push he needed.

Cranky clasped her shoulders and drew her with a caress of her cheek back up to his mouth. He kissed her, hard, without restraint, letting any feelings of fear or guilt slip away. He allowed himself to want her, right then, right there, in ways more intimate than he ought ever dream of. He could feel a rush of sensation, a pull of inertia working its way down his chest to his gut, and even to parts lower. He gripped her tightly, holding their bodies closer, so that even their heartbeats could feel one another.

“Matilda,” he whispered against her lips, just enjoying the way her name filled his mouth, the undulation of the syllables. It wasn’t a question, a command, only a word that tasted like starlight and silk.

She shuddered again in his grasp, and he felt her moan back against him just at hearing her name said. He said it again between kisses, working his lips across her cheek to the crook of her jaw, her neck, the curve where her shoulder met her chest. Every inch of her was warm and alive, and he could feel her energy filtering into his body with each individual kiss.

Her voice came out in thready, half-conscious moans at his touch, and her hooves began to move across his chest. They tugged at his tie, loosening it, and Cranky reached up to help her pull it free. It fluttered to the floor like a forgotten party streamer. His hooves moved up to the back of her head in response, pulling the end of the pink ribbon until her mane tumbled free in a cascade of floral scents and shimmer. He felt the mane brush his face, his ears, like it was a whisper in physical form.

He wasn’t thinking or paying attention, entirely going by feel now, so he didn’t fully notice as they sank back towards the floor. He didn’t notice as his body moved over her, and her head bent to rest against the black marble. He didn’t even notice as her mane splayed out against the smooth surface, creating a dark shimmering halo around her head. Only when her legs parted, and her back hooves grazed his hips, did he realize what was about to happen.

Finally, this gave him pause. He stopped, lifted his head away, and looked down at her beneath him. Her hooves were up against his chest, with his on either side of her head. She was in complete surrender to him, but her gaze was inviting, willing, encouraging. Hesitation again slipped into his thoughts, nerves, fear. He’d done this before once or twice, but it had never felt like this, and he’d only met her tonight. This seemed crazy all of a sudden, completely irrational. He should stop this, before he went too far.

But… didn’t he want this? She was an angel, didn’t he want her to be his angel, in her heart and body too? And just as importantly, didn’t she want this? He could get hurt, he might make a mistake, he might disappoint her somehow. But could this really, possibly, maybe… be worth the risk?

Cranky wet his lips with his tongue, only now realizing how parched with hard breathing they were.

“Matilda, should we…?”

“No, we shouldn’t stop,” she said quickly with a shake of her head.

Cranky couldn’t help but smile then, and he felt a swell of relief in his chest.

“I was going to say, should we keep going?”

She looked at him, her expression one of mild surprise, then she smiled and laughed. A real, blushing, honest laugh, the same one he’d first heard when he saw her.

“Yes,” she breathed, “for the love of Equestria, yes!”

That was enough for him. Cranky bent to seal their mouths in another kiss, then pushed his hips forward against her. He was already so hard, so wanting, and he could feel the seeping of warm moisture from her against his inner thighs. It was a matter of breaths and heartbeats for him to line himself up with her opening, and for him to make his first thrust inside of her.

Matilda broke the kiss with an abrupt gasp. At first, Cranky was afraid he’d hurt her, but the breathy gasp ended in a warbling moan of pleasure, and he knew she’d be okay. She was so warm inside, a velvety wetness completely encasing him, and the pleasure was so great that he had to force himself not to cry out in ecstasy. Her legs shuddered on either side of him, and he paused, letting her adjust to his size, relax around his member. She clenched briefly, so tight it was almost painful, and then he felt her muscles give somewhat, and her legs stopped trembling. Only then, once they’d both regained some control of themselves, did he begin to move.

His pace was a slow, steady one, just a simple in, then out. Not so deep as to cause pain, but not so far out that he ever fully exited her. With each individual stroke, he could feel her twitch and tighten around him, then release as he plunged slowly back in. It was as if her body was desperately trying to hold him inside, afraid he might withdraw. He was going to do nothing of the sort.

For his part, Cranky couldn’t suppress the occasional groan or muffled, guttural sigh of relief. As his hips began to find their own rhythm, unbidden by his thoughts, he allowed himself to focus on brief snapshots of the jenny beneath him. Her head rose on occasion to toss back, her mane lashing out against the marble like vines, her mouth opening in wordless cries and panting. Her hooves pawed against him as he thrust deeper inside her, reaching new and warmer depths than he had yet touched. Her eyes opened, half-focused and dreamy, before shutting with each specific wave of pleasure that hit her. He couldn’t be sure if it was evening dew against flower petals, or impassioned sweat that kissed her brow and cheek.

Her hips began to find a pace of their own as well. They rose as he came down against them, then withdrew against the hard stone floor as he pulled back. Each thrust became deeper, each retreat more severe. Her body plucked at him, stroking him from head to base, and his own moans became louder, more desperate. He’d never really been vocal before, but right then he didn’t feel ashamed to be so. Any nerves he had seemed to pale in comparison to the pleasure spiking through his mind and body.

In his loins, Cranky began to feel a mild urgency. It was slowly building but there, as an ache that demanded to be released. He tried to slow, to prolong things, but he felt Matilda tighten her back hooves around him, urging to keep up with his current rhythm. The tightness in her legs moved to between them, and she clamped down briefly on him. When he let out a moan this time, he could hear her own echoing behind it.

“Matilda,” he said again, breathing it out between strokes like it in itself was a sound of pleasure. “Matilda, Matilda, Matilda…”

Her soft cries of desire and lust rose in intensity and passion, and soon her hips were actually thrusting up against him in time. He couldn’t help but quicken his movements, tense the muscles in his stomach and rear, driving himself into her over and over again with abandon now. He wanted her. He had her. No matter what, in this moment, they were together, joined, one, and enjoying every second of it. It was the most alive he’d ever felt.

The urgency in his loins was now more than mild. It demanded more of him, pushed him harder, and he thrust deep and fast, his pace becoming wild. Her rhythm seemed unable to keep up, and he didn’t care, as long as she was enjoying it. At last, she was left holding onto him, gripping for dear life, her every breath coming with sound and wanting. He could feel her body clenching around him over and over again, with increasing intensity, spurring him onward. It wouldn’t be long now.

Something in him compelled him to speak, to tell her what was about to happen. But as his eyes focused down on her, he could see tears of exertion hanging in her eyes, a flush in her cheeks, and words ready to burst from her own lips. The sight was enough to push him to the very brink.

“Matilda, I…” he gasped out, feeling his body reaching the point of no return.

Wordlessly, she wound her hooves around his back holding him deeply inside her, thrusting up against his hips. As his lips parted in a moan, she pulled him down to her body, joining their cries of release into one trembling kiss. He felt her go rigid, felt a rush of warm liquid against his legs, and it was all he could take. The feeling of her cumming around him was too much, and with a shudder that rippled from his head to his hooves, he let go. He pumped his hips forward once, twice, as a burst of pleasure erupted in his loins, spilling all he had into her body.

The vibration of pleasure traveled through his form over and over, always pumping at last to the same point, where their bodies met. His final thrusts slowed, his own muscles released, and he fell towards her, barely catching himself with quaking hooves. He closed his eyes, trying to get enough cool air into his lungs to think straight, and when he opened his eyes, he found an angel beneath him on a starry marble floor, the entire cosmos gleaming in her satisfied gaze. And she was smiling, the most beautiful smile he had ever seen.

With a trembling hoof, he reached up to her cheek and touched it gingerly, feeling that her body was still shaking as well. His eyes moved over every inch of her face, a smile slowly spreading across his own lips.

“Are you alright?” he managed to whisper.

She nodded, and he continued to study her. Between pants, she cocked her head and looked at him with a touch of concern in her expression.

“What is it?” she breathed.

Cranky’s smile broadened, and he again ran a hoof over her cheek.

“Just checking to make sure you’re real,” he said. “I expect to wake up any minute now.”

She chuckled, and he could feel the rumble of it pass from her body into his.

“Charmer.”

“Only for you.”

He leaned down and gave her a gentle, affectionate kiss. He held it there, just a tender press of her lips against his, a gesture of intimacy rather than desire. When at last he withdrew, he felt he could finally breathe again.

Matilda gave a whimper as Cranky pulled out of her, and he felt a sudden rush of fluid follow. He glanced down between their bodies to see a shimmer of paleness across the dark of the marble, a stark contrast. It might have been gross to him before, messy, but right now, it seemed to fit, like another scattering of stars in the reflection on the surface. He rolled to lie beside her, and stared up through the window next to them. The moon was beginning to set, and he couldn’t say for sure how long they’d been there. But the night wasn’t over yet, they could stay at least a while longer.

There was the sound of a sigh next to him, and then her felt her nuzzle up beneath his leg to rest her head against his chest. He curled a leg protectively around her, hugging her close, and the two sighed in unison as the glitter of afterglow settled around them.

“That was…” Cranky said, searching for a word, “exactly what I needed.”

“I could say the same. You were wonderful,” Matilda said dreamily.

“You’re just saying that.”

“I most certainly am not.”

“Would… would it be foolish of me to say that I think I’m in love with you?” Cranky said haltingly.

It didn’t seem like the right thing to say, but at the same time, he had to ask. Hasty though it was, strange though it was, he had a feeling inside him he couldn’t deny, and he knew it was real. Matilda was silent a moment, then he felt the vibration of her laughter.

“It would, but you can say it anyway if you like.”

“Well, then… I think I’m in love with you.”

“I think I might be as well.”

They both went silent, basking in the words that hung in the air around them like dancing fireflies. Matilda was the first to break the silence, and now her voice was less playful, more serious.

“Hey, Doodle?” she asked.

“Yes?” he didn’t even balk at the name anymore.

“Would you… like to find out for sure?”

Cranky raised his head to glance down at her. She looked back up from his chest, smiling distantly, but nervously too. As if there was any chance in the world of him saying no.

“Well, what exactly are you proposing?”

“I offered to take you with me, travel somewhere when I leave. If you come see me tomorrow, at my room, we can talk about it more but... I don’t know, what do you say? Want to come adventuring with me a while longer, see where this adventure,” she patted his chest then, right over his heart, “will lead to?”

Cranky drank in the scene of her, taking a mental picture of her sprawled across his chest, capturing it so he might never forget. Then, once he had it all outlined and shaded in, he allowed himself a growing grin.

“It might be rash of me, but you know, maybe rash is good. Maybe it’s the push I’ve been looking for, and I really would like to see where all this leads. I know how I feel about you, I know you feel for me too, and I know that this has been the most magical night of my life. If you lead me, I will follow you. I will follow wherever you lead, because in the short time I’ve known you, you have only lead to beautiful, magical things.

Matilda gasped in, and he could see a blush return to her cheeks. Her smile grew, now hopeful, excited.

“Are you saying you’ll go with me then?” she said, her voice quavering.

“Miss Matilda,” Cranky said, as regally as he could manage. “I would be honored.”



Author's Note

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