Guilty Pleasure

by Karrakaz

Initiatives and Immeasureables

Previous Chapter

The guest room Twilight mentioned is little more than a closet that has had a bed crammed into it. It is so small in fact that if I were to stand up with enough force, I might well poke a hole in the ceiling.

Twilight, upon realising that teensy detail was, of course, immediately flustered and said she’d take the guest room in my stead. With equal certainty I told her it would be fine. “It’s not as though I’ll use it for anything but sleep.” I said in my infinite wisdom.

How ironic then that sleep is the one thing that won’t come to me. Tossing is okay. Turning works just fine. It’s just sleep that refuses to cooperate, limiting me to other nocturnal activities. Wiling away the hours thinking about the life I would have with Twilight sounds appealing, but I’m afraid it would quickly drive me up a wall with desire, which is something I can ill afford right now. Residing in a library, the alternative is obvious. I might not be a bookworm in the way that Twilight is; devouring books wholesale with a seemingly insatiable appetite for knowledge, but I have been a fan of both romance and adventure novels since the early days of the printing press.

Trying to come out of the closet doesn’t go as smoothly as I would like. Perhaps it would have been prudent to start with a source of light, but before it occurred to me that my problems are in part due to my unfamiliarity with my surroundings, the space above my head has already become more cheese than ceiling.

A brief pause to correct my illumination situation, I make my way over to the library proper without any particular idea of what I’m looking for. Perhaps something old by Trotstoy? The idea, upon having had it, seems rather unappealing. I want something lighthearted and mayhap even funny.

There was that ribald little collection my nobles were all raving about a mere few centuries ago... Cantermarey’s Tales, that was it. Quite scandalous in its time, though rather tame compared to what is considered as much in this day and age.

I find the book quickly enough. It’s been misshelved in history, but then, I expected that. While many of the stories were inspired by events at the time, with very few exceptions it’s all nonsense. I settle into a nice, comfy bean bag (Twilight’s prefered reading spot I suspect) and open the dusty tome.

When next I become aware of my surroundings, the book is on the floor, the sun is shining and judging by the muted, but undoubtedly good natured murmurs, Twilight is in the kitchen. I guess I must have dozed off at some point. A stiff neck and painful wing joints further clarify that I haven’t moved all night. I stretch with a long-suffering groan and twist my neck this way and that, trying to limber up just a little.

Scant are the times I’ve heard Twilight sing, and on the few occasions that I did it was more a mumbling along while others sang happy birthday. Even so, I knew she has a good voice for singing. I just didn’t know quite how much I liked the sound of it, until now.

“—n’t stop me now! I’m having such a good time, I’m having a ball!” She hums the rest of what is certainly an upbeat melody when she steps through the doorjamb into the library proper. She stops dead and smiles at me brightly. “Good morrrning, Prrrincess~” she exclaims, rolling the R’s like she were a purring cat. Or mayhap a pirate? “Sleep well?”

Twilight’s entrance is accompanied by a sweet subtle scent that makes my mouth water, and I cannot help but wonder what she was doing in the kitchen. The Twilight I knew as my student didn’t know how to cook. By design as she said it ‘took too much time that was better spent studying’, but then, back when she was my student I would never have expected to see her with a pair of wings either. Her happiness, though, is nothing if not infectious, and I present her with a smile of my own. “Splendidly, though I wouldn’t recommend sleeping in a beanbag chair.”

Twilight nods knowingly. “Murder on the neck.”

“That song is—”

Her smile widens. “Catchy, isn’t it? It’s been stuck in my head for weeks.”

I nod. “Very much so. I have never heard anything like it. Where did you..?”

“I heard it while I was researching those four-dimensional magicks.” She replies with no small measure of enthusiasm. “And apparently it was written by a queen!” Her horn lights up and from the kitchen a procession of plates and cutlery fly out into the library, followed swiftly by a pile of pancakes. (The fluffy kind, my favorite) She holds them in front of me letting the aroma permeate the room, and making me smack my lips in anticipation. “Pancakes?”

“Yes. Please.”

Rather than putting a pancake or perhaps two pancakes on my plate as was my expectation, she simply puts the entire stack in front of me without so much as a second glance. The pouring the of syrup is next, and her application is more than generous, but just when I think my luck couldn’t get any better, she tops the whole pyramid of tasty delight off with a big scoop of whipped cream. A more decadent treat hasn’t been seen since the cows celebrated their emancipation, and I can’t wait to dig in.

“I’ve made my decision.” Twilight declares before I have but picked up my fork.

For an instant, I cannot decide if the delicacy, or its creator deserves my attention more. The dilemma is swiftly resolved when I remember that I should have enough mental faculties to eat and listen at the same time. So, with fork on its way to food, I turn an attentive ear to Twilight. “That’s a more swift resolution than I’m used to from you,” I tell her only half jokingly.

Twilight nods with a gravitas that’s almost comedic. “I realised that if it’s true that you love me, and this is in fact not a dream, which I’m ninety-five percent sure of, then I’d be an idiot not to reciprocate. Especially since it’s been something I’ve dreamed of for so long.”

“And if it does turn out to be a dream?” I ask despite myself. There’s no reason to cast doubt now that Twilight seems to have made up her mind, but my ever illogical curiosity won’t take no for an answer.

“Then, I am going to make Luna wish she had stayed on the moon.” A simple statement, with chilling implications. Twilight has grown in the time she was away from the castle, as I knew she would. Although I can’t say that I’m entirely happy with it. There was always a kindhearted sort of naivete to her while she lived with me. An optimistic view of the world, which the world seems to have knocked out of her.

“Lucky then, that it isn’t.” I say, quickly taking a bite afterwards to avoid saying more problematic things. The pancakes are, perhaps, not as good as I had imagined them to be. But then, for that to be the case Twilight would have had to gain several lifetimes worth of experience in a matter of years. As it is, they are merely delicious, and the first bite is quickly followed by a second, and then a thirtieth, with all of the intervening ones supposedly going unrecorded because I’m too preoccupied actually enjoying my meal.

Upon returning to my senses, such as they are, I find an empty library. That is to say, a library with no Twilight in sight, though the sounds of rushing water give some inkling as to her next course of action. Maybe she’s made plans for the both of us to go out on a date? The thought is scary and exhilarating all at once. I should probably take a shower as well. Not to mention needing to find something to wear. The dress that hid the wine stain was lost somewhere between my talk with Luna and waking up in Twilight’s bed. And to my knowledge, Twilight, however well prepared she may be, doesn’t have anything in my size.

Then again, knowing Twilight, she’s probably enlisted the aid of Rarity and a dress will appear moment before I’ll need it. That mare truly does work miracles at times. Perhaps I should reconsider my stance on employing national heroes.

“Twilight?”

“Be right down!”

While waiting for Twilight to do just that, I simply sit back and enjoy the ambience, comparing the oak and Ponyville to the sounds of home. Most notable by absence are the noises and murmurs of other ponies. In Canterlot no matter where you go, there are always others around. Not so here. Most of the noises in Twilight’s abode come from nature herself. The soft rustling of the leaves, the wind which seems to picking up pace... “Perhaps today isn’t really the right time to go out, Twilight,” I say, more to myself than actually to her.

“I didn’t intend to. Celestia,” comes the reply from the stairs. Startling in and of itself, but that surprise is negligible compared to what I see when I look up. Twilight is standing on the stairs , clad in a skirt and blazer combination that, at one point or another, was the school uniform for fillies at the school for gifted unicorns. The surprising part is that it’s at least three sizes too small, and hugging her curves like a drowning stallion holds on to driftwood. “So...” she asks, after striking a pose that emphasises her sexuality even further. “Think you’ve got room left for dessert?”

I merely look at her, mouth agape. What in the world am I supposed to say to that? If it weren’t for the excellent meal and her general coherence, I would have sworn she was drunk.

The moment can’t have lasted a minute before her composure cracks and she bursts out laughing. “Sorry! I knew it was terrible, but I just wanted to see if I could say it with a straight face.” She hops down the rest of the stairs, while I inconspicuously rearrange my wings and tail both.

Twilight wouldn’t be Twilight, however, if she didn’t see through my attempts at modesty. “You actually like it?” she asks, surprised.

I do can do little more than nod. “Yes. I know I haven’t told you in so many words but...” a brief pause to swallow the saliva gathering in my mouth is in order. “I think you’re an incredibly sexy mare, Twilight.”

“I’m actually not,” she counters almost immediately. “I mean, I’m not bad looking but in comparison Fluttershy for example? She could be... has been, a model! I can’t help but feel a little plain compared to that, even with the new additions—” she glances at the wing at her side meaningfully. “I don’t really know all that much about what ponies consider to be sexy but I’ve always had this student-teacher fixation and...” She clamps her mouth shut, blushing furiously. “I’m just going to stop talking now.”

So help me I cannot help but laugh at Twilight and the position she’s put herself in. She looks at me, a blushing purple bundle of embarrassment, but eventually she begins laughing too. It turns into a laughter cascade where, when one is on the verge of petering out, their laughter is rekindled by the laughter of the other until both of us are gasping for air.

“Goodness!” I say as I heave in a great gust of air, still feeling stray giggles that threaten to bubble up to the surface. “It’s a good thing Luna took over the sun for today, I feel lightheaded enough that I’d likely crash it into the ocean!”

Twilight weakly lets out another giggle, followed by a groan. “No more! It’s starting to hurt.”

“Are you sure that’s not from squeezing into that outfit?” I ask her with a single eyebrow raised, all the while trying to suppress the urge to burst out laughing once more. “I remember it was form fitting even when you went to school in it.”

“Hey! It still fits fine... mostly. The skirt is a little short, though...”

“Don’t think I didn’t notice.”

She uses her magic to tug on the hem of the skirt, only drawing more attention to the lack of cloth. I could suggest roughly a dozen means to do so magically, and I’m convinced Twilight has more spells for it than even that. The fact that neither of us mentions such is probably the most clear indication of Twilight’s intent, and my understanding of that intent. Slowly, almost gently, I unfurl my wings, relieving some of the pressure on the muscles in my back, and letting Twilight know that I’m eagerly awaiting what comes next.

“So,” I tell her softly. “Knowing you as well as I do, I’m sure you planned out the entire day for us. So what happens next?”

“Next...” She mumbles while walking towards me, all traces of giddiness replaced by a nervous intensity that is so intrinsically ‘Twilight’ that I cannot help but smile. Of course, just when I think that I’ve figured her out, she does something that catches me completely off guard. “Teacher,” she begins, her voice a full octave higher than usual. “I know you said there would be no do-overs, but I really, really, really need to get a good grade to pass the year.” She spins around and raises her tail while looking over her shoulder. Letting me know that firstly: she’s not wearing the underwear portion of the uniform, and secondly, the roleplay turns her on as much as it does me, if not more. “Are you sure there isn’t anything I can do to change your mind?” She asks, letting her voice quiver just enough to make it seem inviting.

Dumbstruck, it takes me a moment to mentally shift gears. I cannot figure out which of the two is the more unbelievable occurrence. Twilight of all ponies propositioning me as her teacher, or the idea of Twilight getting a failing grade in the first place. It all seems so very surreal.

“Teacher?” She asks again, apparently worried about my prolonged silence.

“Don’t... don’t think that I’ll give you a passing grade, simply because you have a nice ass, Miss Sparkle,” I say in my most authoritative tone of voice, while pondering the strangeness of it all. “As with anything, you’ll have to work for it, and show me that you understand the subject matter.”

Twilight jumps and spins around in mid-air as though she was waiting for me to say exactly that. “I’ll do anything, Princ— teacher!” She says enthusiastically, adding a wink. “Anything you want.”

Unlike Twilight, who seems to have the moment planned out to a tee, I’m still lost in uncertainty. Calm down, Celestia. Deep breaths. What would you do in a normal situation? I wouldn’t have said what I just said, for one. The last time this happened I turned the student away with a stern reprimand, which is what makes it all the stranger. Okay, okay... focus on something else. What would you want Twilight to do, if you could ask her to do anything?

“I think we should... redo your oral exams.” I say at length. Oral— or, kissing, colloquially seems like a safe enough thing to start with.

Unfortunately (fortunately?), however, Twilight’s interpretation of the word seems to be somewhat different from my own. She looks at me with wild excitement in her eyes and a grin that wouldn’t be out of place on a predatory creature.

I realize my error fairly quickly as she begins stalking me, her eyes directed at flank, rather than my muzzle. “Well, all right, but I’ll need to clear the table to have enough space for my exam...” she says in a coquettish voice that is more a purr than anything. “I hope that’s okay?”

“Wait, I didn’t mean—”

“Where are you going?” she asks when I backpedal out of her reach, upending the stool I was seated on. It almost sounds like a growl while she stalks after me.

“I meant kissing, Twilight!” I reply through a nervous laugh. The overwhelming performance she put on last time was wonderful, but I would very much like to be able to reciprocate this time.

She stops, stands upright, and goes: “Oh... I... I knew that.” Now that she’s standing up straight, the similarities with a predator have faded quickly and my heart slows a beat. Other parts of me aren’t as willing to simply give up, however. Strange, I never would have thought that I, of all ponies, would find excitement in being prey to somepony.

I lick my lips to wet them, and cautiously approach Twilight. “N-now,” I tell her, ignoring the quaver in my voice while leaning in. “Before we review how much you remember, allow me to show you how a proper oral exam is performed.” And with that, I kiss her.

With my emotions scrambled the way they are, I know for a fact that my kiss isn’t anything like it should be. It’s too fast, too shallow, and over too quickly to be sensual or exciting. It’s nice enough for what it is, but from the look on Twilight’s face, she was hoping for more. Hell, I was hoping for more. But it makes one thing crystal clear. Either I seize the initiative, or Twilight’s going to marehandle me again. Fortunately, she’s put me in a favorable position, as being the teacher to her student role. I need only play my part right. The part of a lecherous teacher who will put her student in compromising positions in exchange for a passing grade.

I can do this.

I can do this.

“Ahem,” I clear my throat audibly before giving Twilight the sternest look I can muster. “That was even worse than what you showed on the exam, Miss Sparkle.”

“B-but I thought you said you were going to—”

“Ah, ah, ah.” I interrupt her, holding up a hoof. “I will tolerate no backtalk from a filly with an F on her report card.” I shoo her away with a hoof and walk back to the table, taking my seat back before saying: “Now, I want you to try again, and this time, watch your teeth, use your tongue, and slow down.”

“Y-yes, Teacher.” Twilight replies, cowed. She steps forward to stand in front of me, closing her eyes and puckering her lips.

“Now, Miss Sparkle, how are you going to improve if you cannot gauge your partner’s reaction?” I tell her in a somewhat gentler tone, before leaning forward and kissing her again. Her eyes open and gaze half-lidded into my own. Much better, not that she’ll glean much with a dazed expression like that, but then, it’s called role-play for a reason. Besides, there will be many more chances to teach her everything she needs to know.

I linger in the kiss for longer than needed, and shorter than I would like. Even going so far as feeling a little regretful that I ended it when it is over. It seems that, for Twilight, is was more than long enough, as she gasps for air the moment we separate. My concern flares, but is immediately squashed when she treats me to a most brilliant smile. “Was that... hufff... was that better?” she asks in between deep breaths.

There’s a strange and yet comfortable juxtaposition in seeing the Twilight I’ve known for most of her life in the situation we are currently in. It dispels much of the awkwardness that still held in my mind, making room for more lecherous thoughts. I give her a half-lidded smile for a change. “Much better, Twi-Miss Sparkle.”

She glows under my praise, and I need to withhold her from immediately going for the next attempt at perfecting her kissing technique. The pout that follows is almost enough to make me reconsider, but it luckily doesn’t last long. “What’s next?”

“A quiz,” I reply decisively. “It will be multiple choice, and getting the answer right could earn you a lot of points.”

Twilight sits up straight and nods attentively.

“Tell me, which erogenous zone of a mare is most often neglected or outright forgotten during down and dirty rrrrutting?” I let the Rs roll on my tongue and delight in the expression Twilight makes at hearing me be so vulgar. “The wings, the tail, the flank, the teats, or the ears?” I continue without missing a beat can feel my ears burn with an imagined shame. Talking about sex in such vulgar terms has been a taboo for the last three hundred or so years, and I’ve been a willing, or at least apathetic participant. Until now. Unless I actually let it stop me, the taboo will only serve to heighten the excitement.

“Well,” Twilight begins reasoning aloud as she is wont to do. “I don’t think that...”

For the third time in as many minutes I silence her with a hoof. “This is not that kind of Oral exam, Miss Sparkle. You may give me your answer while simultaneously showing how to properly lavish attention upon the body part in question.” I say while getting up from my seat, and walking over to the center of the room. Spreading my legs slightly and hiking my tail out of the way (not that it needs much encouragement) gives her all the access she could need. Putting myself on display like this, even if it’s only for Twilight feels wrong, not to mention the thought that ponies could come into the library at any point and see their Princess on display like a mare in heat. Simply imagining being caught like this is enough to give me a miniscule orgasm. I’m not sure if Twilight has noticed my shudder, but I’ll have to remember to clean up after the fact, a pool of mare cum this big leaves nasty stains on wood.

Had I asked her this question when she was sixteen, I’m completely sure she would have gone for my wings, right answer or no. So obsessed was she with the sky at the time, that she cajoled some of the guards into taking her flying more than once. This was after she tried to convince me that flying was paramount to her education, and when that didn’t work, that she had some rare disease that only spending a day at high altitudes could cure. The guards fell for it, even if I didn’t, and she spent weeks in the air believing I wouldn’t notice. During her studies on wings and how to possible magically manifest them, she of course found out about their more sexual characteristics as well, and in horny teenage-naivete tried some of the things she learned out on me. I reprimanded her then, but I’m not entirely sure I would do so now.

The right answer to my question are the ears. In the hooves of a skilled lover, they alone are enough to drive a mare to orgasm. In combination with other zones one’s partner has access to... well, let's just say that I have firsthoof experience on what it feels like to spend an entire day as a puddle of pure bliss. Skilled lover are the operative words there, however, otherwise the question would be pointless. Many ponies don’t know enough to give proper attention to the ears, and more simply hope for the best if they do remember to do something with them.

Note to self: Teach Twilight everything I know about sex.

Twilight’s area of expertise evidently does not extend to small but interesting facts about lovemaking, or kama-trivia, as I like to call it. At first it seems that she’s chosen for my flanks where she spends some time praising the sun with her lips. But she doesn’t stop there and quickly lowers herself to suck on something more intimate.

For all of the experiences that I’ve had in my long life, bearing a foal was not one of them. Not for lack of trying, mind, especially when I was much, much, younger. But it simply never seemed to take. At first I bemoaned my bad luck, then questioned the virility of stallions, and finally wondered if I might somehow be the problem. All too subtly did not having any foals of my own became just another matter of fact, and that feeling of something missing in my life faded into the background noise of everyday life. Now, however, with Twilight sucking on my teats with greedy insistence, that feeling grips me again, and I find myself wondering (briefly) where we might find a spell to satisfy that urge, or as a last resort, a donor.

“Miss Sparkle, I uuhhhngghh.” Just as I try to relay to Twilight that her choice isn’t the correct one, she sneaks in a lick up to my clit, effectively cutting me off. She doesn’t stop there, either, working her way from being in between my legs to behind me so she can better get at my slick cunt. “Hmmmm, very good,” I murmur despite myself.

The next thing I know, something warm and surprisingly solid pokes at the entrance to my vagina. I suck in a breath and quickly look back to see what else Twilight has in mind. She looks at me with a nervous-yet-cocky smile and asks: “Teacher, can I use props for my demonstration?”

In her magic hangs a fleshy looking dildo. One bigger than I’ve ever seen, though granted, I haven’t come across very many. It was without a doubt bought with me in mind, as I seriously doubt Twilight could fit even half of the monster herself. Where she bought it, or where she kept it up till now are questions that will have to go unanswered. I’m worried that after so much time, the stimulation, the feeling being filled by something... somepony, will push me over the edge within seconds.

“Actually, no, you may not.” I tell her, while strategically moving my behind away from the turgid tool in Twilight’s magic, lest my resistance falter and I simply let her do as she will. “In fact,” I continue, snatching the dong with my own magic. “I think it’s about time for the demonstration to come to an end. You put forth an admirable performance, especially in your care for your partner, but your answer was, put plainly: wrong.”

Try though she might, Twilight has a hard time painting a downcast expression on her face; the whole effect undone by a happy glow that permeates every fiber of her being. “Then...?”

“I will instruct you, so stand up straight.”

She arches her back a little, like a soldier standing at attention. It might have even been impressive were it not for her tail which droops over her horn. “Yes, ma’am.”

I circle her once. Twice. Sauntering around her while taking in my lover’s features. The sight of her makes me lick my lips. Her vaginal lips are puffy, there’s rivulets of her excitement running down her left leg, and her wings strain at the joints to stay in place. Love button winks at me, and I can’t help myself, leaning in to get a taste of her liquid love. It tastes bittersweet, and is overflowing in its abundance. I lick my lips again and move on kissing up her flank and move to stand over her while I kiss the tip of each of her ears.

“Pay attention now, Miss Sparkle. I don’t want you to miss this,” I whisper into her ears as though she were an observer before running my tongue over the outer edge of her left ear which immediately flicks away. I catch it with my teeth and bite on it lightly while bringing Twilight’s own dildo into position behind her needy sex.

She trembles ever so slightly; nervous now that I have the reins. I place a gentle kiss on the top of her head and nibble on her ear again. “I have to admit to being curious, Miss Sparkle,” I say breathily. “What made you go for my teats over my ears?”

“I—” she gasps as I clamp down lightly at the fuzzy tip of her right ear. “I’ve spent most of my teenaged years following along behind you, and I saw them all the time. I just thought it would be so nice to suckle them—”

I chuckle in appreciation. “Whereas my ears were too high up to admire?”

“Y-yes,” she replies with a soft laugh. “I don’t know... I guess I just didn’t think you were being serious...”

“Deadly,” reply with a purr giving her horn a sudden lick which makes her moan. “Twilight, there’s enough material for many, many more lessons.” I punctuate the sentence by pressing the flat head of the dildo against her entrance, while simultaneously resting some of my not inconsiderable weight on her back. The effect is similar to how a stallion would come to support himself on a mare’s back during frantic rutting and the response is electric. Twilight lets out a long drawn out groan and her lower lips convulse once before letting the faux penis slip inside. She moans again and again, loudly and needily, and I briefly wonder if anypony outside might have heard her, but the thought has come and gone before any serious consideration is given. If me being caught exposed turned me on, this is several times better still. “And trust me,” I continue with my half-remembered sentence. “I intend to mold you into a very capable lover indeed.” Seeing Twilight quiver and feeling her moans and convulsions through the part where my stomach touches her back triggers another micro-climax which I ride out in silence while slowly pushing the dildo further in. I run out of Twilight a long way before running out of dildo. The medial ring hasn’t even reached her pussy, but I slowly begin to drag it out of her while paying special attention to her ears.

“I...” she gasps. “Celestia...” Her front legs quiver and give out, putting her in a face down ass up position. Though I suspect her behind is only being supported by the foot length of faux stallion flesh inside of her, rather than her own hind legs.

“However,” I say in between somewhat laboured breaths. “I think I’ll... save that for later.” After another incoherent moan from Twilight I lean forward and whisper huskily into her ear, “For now, I think I’ll pay back all of the sexual tension you’ve caused me.”

No more words need be said, and so I busy my lips with the task of finding the weak spots in Twilight’s ears while pumping the dildo in and out of her pussy in a steady, if irregular rhythm. I should honestly pay more attention to her wings, but I blame being rusty at love-making and focus on bringing her to a thrilling climax with just the body parts I’m focused on.

It’s beautiful.

Correction. She’s beautiful. Sensing that she’s close to climax through the convulsive way her inner muscles try to hold on to the dildo, I flip her over onto her back and kiss her while driving the faux-meat as far as it’ll go. Her eyes are pool of pure lust and love and she fairly screams into my mouth while her wings beat uselessly against the floorboards and her femcum shoots out around the dildo. Twilight, it seems, is a messy little mare.

“Princess...” She murmurs in her state of ecstasy followed by a low groan when I softly lick the tip of her horn. While too much stimulation can cause pain just after a climax, especially one as world shattering as the one Twilight just had; subtle and creative lovemaking can bring anypony to a second, third, even fourth peak in a fraction of the time. Essentially, I am going to drown her in a sea of bliss for as long as my, admittedly rusty, skills will allow.

Which is where the ears come in. Using tongue, teeth, and magic alike, I massage the outer shell of Twilights ears while also giving a modicum of attention to her wing-joints with my hooves. The key is to avoid major erogenous zones, and focus on the minor ones. Even then, it doesn’t take more than a minute before Twilight is gasping and moaning like a mare in heat once more.

“Ohhh stars, Princess... I’m gonna cum again.”

“Try and fight it, Twilight.”

She shudders, gasps, and gulps in a deep breath, holding it as though that will make the pleasure subside. Maybe it does... I can’t recall ever having tried. I do my bit to prolong her pleasure by subtly slowing my ministrations a little more, but to no avail. A few moments later, another helping of her femcum stains the floorboards, and she collapses, unconscious.

Perhaps I was a little over eager. She isn’t as experienced, and lacks the stamina of my former lovers. For the time being, at any rate. A self deprecating snort escapes me before I curl myself around her. I should be cleaning her up and putting her to bed after all that, but there isn’t any rush. And I do so like cuddling.


“Princess?”

Upon opening my eyes, I’m greeted by the sight of the library, and, more importantly, Twilight’s face sticking out from between the plumage of my wings. I must have dozed off at some point. “Welcome back, Twilight,” I tell her with a smile which she returns with gusto. “How do you feel?”

“Great!” She chirps, right before stifling a yawn. “A little exhausted, maybe, but I’d anticipated that much given my inexperience.” After a little bit of wriggling, she hops out of my encirclement and traipses into the kitchen, returning a few moments later with what looks to be a platter filled with slices of cake. “These are ‘power cakes’. According to ‘Healthy Nutritionals, Grassroots Cuisine’ they’re supposed to help recover your energy after strenuous activity.” She blushes and aims a furtive smile at me. “And I think that what we just did counts as strenuous, at the very least.”

With a chuckle I take one of the cakes and take a big bite out of it. The taste leaves something to be desired. Kind of makes me wonder why I neglected to taste Twilight in earnest. With a smile and furtive glance in Twilight’s direction as she munches on her own cake, I consider simply asking her.

“Princess?”

“Yes, Twilight?”

“I was wondering... I mean... Can I...” She takes a deep breath, stuffs another slice of cake into her mouth, and sighs. “I bought that thing for you... Or maybe... I guess I pretended it was you a few times.”

“Pretended it was...” I laugh at the idea. It seems so silly, but obviously Twilight didn’t think of it that way so I push away my mirth and put on a mask of seriousness. “Like I was using it? Or some sort of spell? Or?”

“All of the above?” she replies with a wry smile. “Point is, I wanted to... can I repay what you’ve just given me?”

“It’s okay to say it, Twilight.”

“I want to rut you with that cock until you cum. And then I want to keep rutting you until you scream yourself hoarse with my name on your lips, or till you pass out.”

A shock of unadulterated need flashes through me like lightning and I smile coyly at Twilight. “Well then...” She goes red in the face to the degree that my excitement is muddled with a small hint of worry that she’ll get an ulcer. “Twilight, calm down.” I lean over the table and clasp her face with my hooves. “Breathe!”

Finally she breathes out and back in, finding a spot on the floor that doesn’t judge and focusing on that. “Sorry,” she mutters under her breath.

“Twilight... I like. No... I love your candid response.” I take a deep breath of my own to keep myself in check and treat her to a coy smile. “So much in fact that I want you to do just that.”

She swallows heavily and nods before sprinting up the stairs back to her bedroom. It’s somewhat bemusing I must admit. I hadn’t expected that of all things would scare her off. Certainly not after what she’d just said, but the actual reason dawns on me when she returns with a rather intricate harness tied around her hindquarters. Attaching the dildo to the harness is, apparently, even more difficult, and takes her almost five minutes during which I can only sit and stare, wondering what it is going to feel like.

Seeing Twilight wobble around with a dong bigger than her foreleg after she manages to affix it to the harness is more amusing than I would have thought. So much so that a snort escapes me despite my best efforts.

“Princess,” she whines petulantly. “It’s not supposed to be funny.”

“Sorry, Twilight. It just looks so disproportionate.” I clear my throat and set myself in a prime rutting position. My body moreso than my mind remembers what that’s supposed to look like. Front Legs bent, hind legs straight; face close to the ground for support later on, and ass in the air for ease of access. It is the most incredibly lewd pose I know of and showing myself to Twilight like this turns me on even more, making me shiver in anticipation.

The anticipation of a weight settling on my back doesn’t arrive. In its stead comes come pushing, squishing and otherwise handling of my backside, followed by Twilight mumbling to herself. For the briefest of moments, I am seized by a fit of frustration. Even a stallion with only half a brain would know what to do when a mare displays herself to him like this. It’s instinctual. Evolutionary. But then I remember that Twilight is not a stallion. She's a mare who has just had her first (second) sexual experience. No matter how capable and enticing she has shown herself to be while inebriated, this is something she is probably going to need some extra help with.

Guiding Twilight in the specifics of inserting stallionhood A into marehood B shouldn’t be impossible but she preempts my instruction by seconds.

“Princess?” she begins timidly. “Could you... please lie down on your side? You’re too big and I can’t get this thing...”

Any frustration that remained is wiped away and replaced by a sense of shame. So preoccupied with getting myself what I wanted that I neglected to think about the actual physical differences, not to mention thinking less of Twilight for not jumping like a stallion would.

With a dull ‘thwump’ I let my ass hit the floor, shifting to look back at her. Twilight lines up the dildo with my swollen vaginal lips with mathematical precision before smiling at me nervously. “I’m going to start now...”

I smile to put her at ease and nod, suppressing a gasp when the tip of that thing finally slips past my outer lips. You never know how much you’ve missed something until you have gone without for over a millennium. Feeling emotionally and physically connected to a pony on this level is better than a climax itself (not that that is very far off). Being on my side works out much better for the both of us. While there’s something uniquely exhilarating about the feeling of a strong muscular stallion on your back as he fucks you silly, being able to see Twilight’s contraption penetrate me at the same time as I feel it against my inner walls has a thrill all its own. Having easy access to kisses and nuzzles is merely a bonus.

It takes a full three minutes before Twilight’s hips bump against my own. A full three minutes of excruciatingly slow pleasure and penetration that, coming from another, I would have labeled as teasing. From Twilight, it’s because she’s careful, maybe even scared. I don’t tell her to stop, or speed up, or much of anything at all, really. Just watching her watch our bonding (and sometimes sneaking in a peek myself) is all I could ever wish for at this particular moment.

“Wow...” she says with an awed expression after she can go no further.

“What is it, Twilight?”

“I...” Looking at me bashfully, she motions at the subtle distention of my belly. “I didn’t think I would get to use it like this when I first bought it, and I never expected even you would be able to take all of it. It’s so big.”

“Twilight? Are you calling me fat?” I ask her jokingly.

She shakes her head. “Of course not.”

“Then please, don’t stop fucking me?” I pout for added effect. A little incongruous with our current activity, but pleasure dies down if not fed, and this really is starting to feel like teasing.

Twilight obliges. Happily. Her movements, though a little jerky and unpracticed, make the dildo rub against my inner walls in all the right ways. It helps that the thing is as big as it is. I’ll never understand how they managed to come up with a size that fills me so thoroughly, but right now, I don’t care. The following minutes are shared by frequent, if short, kisses; Twilight’s laboured breathing while she works the faux meat into me again and again; and my moans of ecstasy. All too suddenly, I reach my peak and scream at the top of my lungs, beyond caring if anypony hears.

For a while all of my experience is reduced to a white expanse of bliss with pleasurable tremors that spread throughout. When I return to being capable of interpreting anything but my own pleasure, I find Twilight collapsed on top of me, panting and heaving like she’s just had a climax that was at least twice as wonderful as my own. And for a few moments thereafter, all either of us do is breathe heavily and smile tired smiles at one another.

“Twilight...” I begin, trying to emphasise what and how much I love about her and cramming it all into a sentence. In the end, all I can come up with is, “I love you.”

“I love you, too.” She replies with a tired smile. The smile dissipates after a moment and is replaced by a more serious expression. “Did you mean it?”

A bead of sweat drips off of the end of my nose as my brain struggles to produce words my tongue to express. Restarting one’s brain can be rather slow after such things. “Mean... what?”

“Just now... you said that you wanted my babies.”

My mouth hangs open in surprise, probably ashamed of its traitorous utterances while my mind was flooded with endorphins. Sluggishly, I try to think of some excuse while my mouth begins muttering about how it’s not possible anyway. “Is that why you...?” I manage before giving up once again, my eyes imploring her to fill in the blanks.

Twilight blushes. “You said that and I just... I couldn’t help myself. It felt so... naughty? Sexual?” She shrugs helplessly before donning her serious expression once more. “I’m going to find a spell, or a potion, or an artifact, or what-have-you to make that happen.”

“Twilight...” I treat her to a weak smile. “I’ve been around for a while, and I don’t think I’ve ever seen or heard about anything like that even existing.”

“And if it doesn’t exist,” she continues full of passion, ignoring me completely. “I’ll make one.”

I laugh despite myself, knowing that if anypony could make the impossible possible, it’s Twilight. “I believe you. If anypony can do it...” The rest needn’t be stated, so after another kiss on her forehead, I move to get up.

“Where are you going?” Twilight asks while struggling with the contraption still attached to her waist.

“I feel the need to take a shower.” Finally back in gear, my brain is already busy filling itself with the possibilities of Twilight making good on her promise. Looking over my shoulder and giving Twilight my sauciest of smiles, I add, “And I would like you to join me for it. If I’m going to be stuck here for two weeks, I want to spend most, if not all of that time making love to you.” Twilight’s little gasp goes ignored, though not unnoticed, and when she fails to open the clasps for the strap-on, I use magic to do it for her. Following it up by lifting her bodily into the air and close enough for me to kiss. “You, my guilty little pleasure, are going to have a brand new lesson plan. And then when you know everything I do about pleasure, we are going to find out whatever else there is.”

She squees softly and tries her best to kiss me on the nose. It’s a struggle because I turn it into one, dodging her and floating her just beyond kissing range for a small prank, which ends when she turns that adorable pout of hers on me.

I may still not sleep a whole lot in the coming weeks, months, or years; but at the very least, I won’t be alone when I don’t.


Author's Note

This story has been a long time coming, but it wouldn't have been as good as it is right now without the marvelous people that helped me make it so.

Thanks to Steel Resolve for helping me brainstorm, getting me over those pesky writer's blocks, and being a good friend in general.
Thanks to BluePaladin and TheGreatEater for providing feedback and for making sure that the entire thing is in any way readable. Thanks to Nova Quill for the cover art. And of course, thanks to you people for taking the time to read the thing. All of you are awesome and amazing.