Twilight Night

by SmutAnon

Rating: mature
Tags: Human, Romance
Length: 3450

You have the privledge of helping Twilight through her first time, and she yours, though one of you is a little less nervous than the other.

You and Twilight have been together for months now, standing happily by each others' side in everything. Everything except sex.

Oddly enough, she was the first to bring it up. It's taken time, but you think you've finally warmed up to the idea. Now it's time to take the plunge, but, as the mare is wont to do, Twilight's over-analyzing things. Just a bit.

Colored cover image source

Published 1970-01-01 00:00:00 UTC
Last updated 2013-09-19 04:30:04 UTC

Twilight Night

"Are you sure about this?"

"Yes, Twilight. For the millionth time, yes."

"Because you were really indecisive for a long time and I don't want you to feel like I'm pressuring you or anything."

"I know." Looking down at Twilight, you can't help but crack a smile. She makes the cutest faces when she gets nervous. "I don't feel pressured."

"Okay, well, you know, you've always told me you just wanted to make sure you're ready, and I'm okay with waiting a little—"

Seizing her horn, you crouch down to her level. Her mouth zips shut.

"Twilight. I'm ready. You can stop delaying."

She turns away, blinking, dousing you in another wave of cuteness. "D-delaying? I'm not delaying."

"If there's one thing you've picked up from all those books, it's how easy you are to read."

Her cheeks bloom red. "That easy, huh?" The excited, shaky tone in her voice disappeared, replaced by a much more tempered, almost wary one. As much as she might try to hide it, she's nervous, just like you.

For months since the two of you started dating—if you could call it that; with Twilight, it was more like going to class—this question had always been at the front of your minds, like a shadow tapping on the shoulder. It had been brought up a few times, always by Twilight, as tactfully as she could manage.

"So... how comfortable are you with having sex?"

Yes, as tactful as possible.

The first time she mentioned it, you were floored. It's not like the thought had never occurred to you, but it's more that you'd completely forgotten you had a partner with sexual needs and wants as well. You made a joke about how she just wanted to do some 'research', but that only frustrated her. Even if you hadn't overcome the species barrier, she had, and you found yourself at a loss for what to do next.

So began the wait.

Twilight, the understanding pony she is, gave you all the space and time you needed. She didn't let you forget about the issue, but as soon as you showed any sort of distaste or hesitance on the subject, she backed off. And each time it happened, you felt worse for being able to overcome your weakness. For weeks, you felt defeated. Alone. Faced with the real possibility that, as much as you loved Twilight, you couldn’t find her attractive.

You don't know when it started, it was so gradual. One day you noticed her rump bouncing up and down as she walked and caught yourself staring at it. Another time, when she was in heat—you can only imagine how difficult that was—the musk she left behind awoke something in you. Then, just yesterday, when you felt her nuzzle up against your side for warmth—that's when you knew.

But for all her wants and needs, if there's anything that can get between Twilight Sparkle and what she wants, it's herself.

"Heh, now that you're actually ready and everything, I'm not so sure."

She stands at the base of the stairs to her bedroom, looking at them like they might as well be a mountain.

"C'mon, Twilight. We'll take it slow, get through it together. I've never done it with a pony, and you've never done it with a human. It'll be a learning experience. You love those, right?"

Her ears perk up. "Y-yeah. It's just so... unknown. Even reading up so much about it, when I'm actually faced with the task, it's like everything in those books meant nothing."

You walk over to her, laying a hand on her back. "Let's go up together, okay?"

With a nod, she takes her first step, you right there with her. "The books never put any emotion to it." Another step. "But that's completely inaccurate." Two steps, this time. "Because all I can do right now is think about how I feel about it." Almost there. "And wonder what you're thinking, too."

"I'm thinking the exact same thing as you. Kinda funny, isn't it? We're so worried about what the other is thinking we can't even enjoy ourselves."

You make it to the bedroom, taking a deep breath while looking at the bed. Twilight had made it much bigger when you started sleeping next to each other, and it'd be more than enough to handle the both of you. Snapping your fingers, you get an idea.

"That's what we'll do, then. We'll enjoy ourselves. We’re so worried about making this perfect it’s getting in the way of having any real fun. Just... do what feels right. Sound good?"

"Y-yeah," she says, putting on her best smile. "I call top!"

Her grin is infectious, and soon you're smiling right along with her. That's another thing about Twilight: you never have to worry about messing up around her. Sure, she won't waste any time in correcting you when you make a mistake or rolling her eyes when you goof around, but she never holds it against you. If anything, you swear she likes it.

Lying down on the bed, you gaze at Twilight, standing next to you, still not entirely comfortable. You can only imagine the hailstorm of thoughts rattling around in her head right now, most probably about how she could mess this up, but you calm her by stroking her mane. Her eyes snap out of the glazed overcast they held and she pushes her head into your hand.

"You called top, remember? And I can't start this without you."

"Right. Okay, here we go."

She hops up onto the bed, crawling on top of you, careful not to step on anything important as she gets into position. Once in place, her eyes meet yours, so full of anxiety and excitement you can feel it.

"So, how do you want to start?" you ask.

"Um, well, I think ponies usually start with a kiss, so..."

Gradually, she lowers her head, closing her eyes and pursing her lips. You don't want to wait around that long, though. You take her head between your hands and push your lips together, testing her mouth with your tongue, trying to get her to open up. If you can just get her to take that first step and relax, you know she'll enjoy herself.

In fact, if your suspicions are correct, she'll be the one taking you for a ride.

She's still too tense for a full kiss, so you break off, running a hand through her mane. "Hey, I'm nervous, too, Twilight, and if I'm going too fast you can stop me, but you should meet me halfway. Open your mouth when I kiss you."

"O-oh. I'm supposed to open my mouth?"

Wait, that wasn't nervousness? Just ignorance?

"Yes. Our tongues are supposed to touch and play around with each other."

"But, but that sounds weird."

"We're about to have the first human-pony interspecies sex ever. I think 'weird' has already come and gone."

"Y-you're right. Calm down, Twilight." She takes a deep breath, and then goes in for the kiss again. This time, though, you don't have to encourage her. She guides your mouth to hers with magic and once again you're locking lips. This time, however, her tongue eagerly encroaches in on your mouth and meets your own tongue, twirling with around with it in an awkward waltz. She's not the best kisser in the world, but for a first time, she's doing just fine. Hugging her neck, you delve deeper into the kiss, returning Twilight enthusiasm with your own.

When she breaks it off, you can tell her eyes have a much more satisfied gleam in them... right alongside a growing hunger.

"That was good. Did you like it?"

"Yes, very much. You're pretty good."

That earns a blush from her, making her look away for a second.

"Sweet-talker." Her eyes drop to your chest and she touches a cursory hoof to it. "So, we should probably get these off, next."

"Ye—"

You're interrupted by a bright flash. The next second you notice you're naked with your clothes folded neatly on the nearby dresser. Of course she would fold them.

"That wasn't too fast, was it? I just... really liked kissing, and I didn't want to waste any time."

"It's fine. I liked kissing too." You let a hand fall down her cheek, feeling it blush hotter than ever.

"Next we stimulate the genital area, right?"

Twilight almost ruins the moment with her comment by about making you laugh, but you hold it in. "I don't think that's the best way to say it. I think you're supposed to talk more frank or even dirty."

"Dirty t-talk? I mean, I've heard about it, just n-never thought about actually doing it."

"You don't have to dirty talk if you don't want to, just don't talk about it like it's some kinda science experiment."

"Got it." She looks around some more, as if trying to find something to do. "I, uh, want another kiss."

"Okay." She starts lowering her head again, but you hold her back a second. "You know, you don't need to run everything by me. I'm here because I trust you, so if you feel like something, just do it. If I want you to stop, I'll tell you."

"Alright."

For the third time, your lips meet, this time more ferociously.

Twilight's practically eating your mouth, plumbing the depths of the kiss to see what she might find in it. You're only too eager to accommodate her, holding her close, pushing back with just as much force as she.

A new sound pops up; a light jingle as her magic flares up. You're curious about it only a moment as your member is undulated with an explosion of pleasure. The shock about makes you pass out, allowing Twilight to dominate the kiss and send your head back into the bed. Whatever she's doing is incredible and impossible; like a thousand tiny shocks riveting your entire shaft, sending wave after wave of bliss through your body. Even with the lack of foreplay, you can feel the edge rapidly approaching. She must be taking the whole 'stimulate the genital area' literally. She isn't stroking your member or touching you at all: she's using magic to directly stimulate the nerves in your cock. Twilight could make you cum in just seconds like this!

Regaining control of your mind, you push Twilight away as gently as possible. The kiss breaks, taking along with it the pleasure in your member. It takes you a few deep breaths to get a hold of yourself again.

"Oh, no, did you not like that? I'm sorry, I went too—"

You wave her off. "No, oh dear god, no, Twilight, that was incredible. But I have a limit, and if you use powerful stuff like that on me right away we'll never get to really enjoy ourselves. I wouldn't do that any more for now, but definitely save that away for future use."

For the first time since getting on the bed, you see a genuine smile light up her face. "Okay. But was the kiss good? Nothing too forceful?"

"Yes, the kiss was—" You shake your head. After that thing she did, your body was rearing to go. You can't restrain yourself any more. "Goddamnit, Twilight, stop talking and fuck me."

You crash your lips to hers, rolling over and putting her underneath you. She gasps but does not protest. Instead, she wraps her wings around you, relishing the contact, pulling you in closer. The kiss dominates your thoughts, your tongues desperate to play with each other. Twilight's no longer the unsure, passive alicorn of second ago, wrapping her legs around you and latching on. Her wings explore your back like hands, touching the skin however they can, kneading and massaging. Her belly rubs up against your chest and her tail wraps itself around one of your legs, wandering over your calves and thighs, down to your shin and ankle. It's like she's discovering your body a whole new way, excited to what she might find.

She breaks away from the kiss to regain her breath, as the two of you are now panting. "You know, I did call top."

Her horn lights up, and a second later you find yourself underneath her like before. She grins at the surprise in your face, using the opportunity to move a wing from your back and wrap it around your member like an oversized hand.

Gasping, she slowly starts to stroke, the smooth, soft feathers touching your shaft in a hundred different ways simultaneously. Your erection strains to get even harder than it is now as she focuses all her attention on it.

"Is this—" she starts, but you don't give her a chance to finish.

"Don't you dare stop."

Her smile widens, the wing pumping faster now, caressing every inch of your wanting shaft in long, deliberate strokes. The precision with which she works is maddening; her inexperience should be crippling her, but she's touching you in all the right ways. The soft texture of the down in her feathers is like a breeze of delicate touches, only intensified by the dexterity with which she wields her primaries and secondaries. Just when you think it can't get better, she tightens her wing's grip, forcing a grunt from your mouth at the sudden new sensation.

Laying your head down on the bed next to Twilight's, you concentrate on her wings, trying not to lose yourself to it but also desperate not to miss a moment of action. You kiss Twilight's neck, letting your hands wander over her curvaceous body, groping her under her slender legs, across her taut belly, near her wings...

That last spot earns a gasp from her, making her free wing spring outwards and the other seize your shaft even tighter. You have to squint to keep your concentration, but you keep massaging under her wing, fondling the spot where it meets her body.

"Oh, g-goodness..."

Her other wing springs out to the side, unable to keep its grip on your member any longer. With your other hand, you give it the same attention as the first wing. Twilight throws her head back, moaning at the touch.

You travel the length of her wings, kneading and rubbing them from base to tip. Twilight's putty in your hands, squirm with pleasure as you work. She regains some of her composure, though, and opens an eye at you.

"D-don't think I'll let you get away t-that easy..."

Her magic ignites, pulling your hands off a moment while she turns around, positioning her mouth at your manhood. As soon as she's in place, she moves your hands right back to where they were.

"Don't you dare stop."

You crack at grin at her using your own words against you but oblige her wishes. She hunkers down on top of you, her leaking marehood lying dangerously close to your face. The moment you think about doing anything, however, your member is enclosed in a cage of heat and pleasure.

"Holy..."

Instinctively, you thrust up into Twilight's mouth, anxious to feel more. Her tongue covers your shaft in tight coils, rubbing against it as she bobs up and down. Your grip on her wings loosens, but her magic grabs your fingers and puts them back to work. You're the one squirming under her now, her long, wet tongue doing wonders to your manhood. You had far underestimated its length, as Twilight can easily encircle your entire shaft in its grasp while her lips move up and down. She then removes it to flick under your head, teasing your frenulum almost like she's making a game of it.

Taking long, painfully slow licks along the sides of your member, she sucks at the head, coaxing out an orgasm, bringing you to the edge with alarming speed.

Intent on not letting her get you first, you remove a hand from her wings and direct your attention to the winking marehood in front of you. Starting with the lips, you draw your fingers across it, breaking Twilight's crippling rhythm on your member. You hear a snort from her as you move faster, teasing at entering, smiling as her sex reacts faster and faster. It's pulsing now, desperate for more and just as Twilight reaches the peak of another bob on your shaft, you slip two fingers inside her.

She moans, almost shrieking as your enter her, her walls clamping down on your fingers like a vice. With the abundant fluid, however, you're able to move in and out without much trouble. You experiment, gauging her reactions for each spot you stimulate. When she's forced to pull her mouth off of you completely to let out a long, deep moan, you know you've found what you're looking for. Each time you dip inside, you hit that spot, sometimes, even holding your fingers in place to rub around it. Your hand and neck are soaked in her arousal, each thrust only bringing out more.

Just as you're sure she's about to cum, she wretches your hand out of her with magic and spins around, bringing you face-to-face with her once more.

"You said you wanted me to f-fuck you, right?" She struggles with the word, but her overwhelming arousal quickly overcomes any trepidation.

"Yeah." Gazing into her eyes, you can see that hunger from before, multiplied a hundredfold.

She slips you inside, face straining as her opening greets its first guest. You say nothing, letting her control the pace, as slow as it may be. When she cringes in pain, you reach out to stop her, but she grabs your arm and shakes her head. It’s difficult to focus on her through the tight passage barraging your member with bliss, but you keep your moans to yourself. After a breather, she swallows more of your length, the intensity on her face growing until she finally decides to withdraw.

Panting, she looks into your eyes, the grimace slowly shifting to a smile.

“I think… I think that’s the worst of it.”

Your brow creases with concern, stroking her mane. “Are you okay?”

“Fine. Yeah, I’m fine. In fact...” She moves herself back to your tip, taking it in without the wince this time. Again, she lowers herself, quicker this time, the pain fading from her face. “Yes… oh, yes.” Taking you in as far as you’ll go, she lets out a long moan, settling for a moment before pulling back. “Now, a p-proper fuck is done... like this!" With no ceremony or pause, she impales herself on you.

You both cry out, throwing your heads back from the explosion of pleasure. Grabbing her head, you crash your lips together in a reckless kiss, one Twilight holds just a violently as you. As you thrust into her, Twilight moves her hips to accommodate, soon finding a good rhythm. Her wings and legs clamp onto you and your arms do the same to her. Every inch of your bodies beg for contact, to be closer, to feel each other in every way.

Twilight pants with each thrust, but that's not enough for her. Her magic comes in to play again, grabbing your member and encasing it in another set of marehood lips, one that thrusts opposite of her other. You cry into the kiss, mind gradually succumbing to the pleasure. Each marehood clamps down on your shaft with incredible tightness as if it was their prey, seeking to pull the orgasm from your body as soon as possible. You redouble your efforts, shifting your angle to hit that g spot Twilight was reacting to earlier. She's forced to break the kiss to cry out, diving her head in-between your head and shoulder.

Unable to withstand her assault any further, you give one last mighty thrust into Twilight, hands finding her wings and squeezing as you release. Twilight finds her own release as well, hugging you tighter than ever before, cum gushing out of her sex just as your seed fills her. Even as you spurt, her hungry walls continue to milk you for every last drop. Only when you're completely drained can you start relaxing, tension draining from your body like water down a drain. Twilight's grip loosens likewise as she nuzzles her head into your neck.

The two of you lie there, panting, soaked in sweat and cum, grinning like fools. You take your dry hand and lay it atop Twilight's head.

"Well, we did it," you say, stroking her mane.

"Did what?"

"Had fun."

"Yeah," she says, cozying herself up against your body, "yeah, we did."