A Royal Lesson

by Fimbulvinter

Rating: mature
Tags: Romance, Sex, Princess Celestia, Alternate Universe, Human, Twilight Sparkle, Original Character, My Little Pony: Friendship is Magic
Length: 14973

Princess Celestia calls Twilight to Canterlot to give her a private lesson. Contains Twilestia with a twist

One day, Twilight Sparkle receives a mystery letter from the princess, summoning her to Canterlot.

The letter promises that she is going to be taught something that Celestia has neglected to teach her before. Curious and eager to obey anything the princess wanted, Twilight heads directly for Canterlot.

Arriving, Twilight finds that the lesson Celestia plans to teach her is one she had never expected.

Notes: 1st person. Characters are fully Humanized. Additional content tags include - Straight M/F, Light Lesbianism, Cum Swallowing,

This is a companion story to 'A Summer Day on the Farm.' It is not directly related, but is set within the same universe. You all requested a sequel, but this is what you get instead. I think that it has the goods, but that is for you to decide.

Now dedicated to Julia Gillard, who has just been deposed as Prime Minister of Australia to the very guy she backstabbed to get the job three years ago - Kevin Rudd.
Sorry, Julia. Consider this a small compensation for your loss.

Published 2013-06-26 16:00:03 UTC
Last updated 2013-06-30 07:18:40 UTC

Chapter 1

It was a bright and clear morning as I stepped off of the train and onto Canterlot station. A quick nod to the station conductor; he had recognized me and waved, so it was only courteous to give him some kind of wave back. Looking around the station, I headed off towards my destination – Canterlot Castle.

Canterlot Castle was a reasonable walk through the densely packed streets of Canterlot town, though I was in no great hurry to get there. The train had arrived a good fifteen minutes ahead of schedule, and my appointment with the princess was still an hour after that. This left me with a fair amount of empty time, but I knew just where to go to spend it.

Moving through some of the back streets, I worked my way quickly towards my favourite coffee shop in the entire town, Doughnut Joe’s. Joe was a master of his craft, blessed with skills that could only be acquired by a combination of natural talent and years of experience. If you needed a specialty confection baked, or even just looking for something different, then you went to Joe’s. Most residents didn’t even bother calling it Doughnut anymore, one would simply say that they were going to Joe’s, and that was all that was needed by way of explanation.

Weaving through the alleys of Canterlot, it wasn’t long before I came to Joe’s door. A converted corner café, Joe’s doughnut and coffee shop consisted mostly of booths and a few tables set up by large windows. The smell of freshly fried dough and various types of sugar wafted out from a pair of well placed vents in the walls. Joe was no stranger to aggressive advertising, and he had correctly reckoned that letting people smell his goods would help to bring them in through his doors. From the number of people that I could see sitting inside his shop, he had clearly been right.

As I caught scent of the delicious pastries, my stomach gave a sudden growl and I realised just how hungry I was. I hadn’t bothered to eat this morning, as Spike had woken me up, shouting that he had gotten a letter from Princess Celestia saying that she wanted to talk to me in person and that I should get on the next train. When you get a letter like that, the thought of mere breakfast tends to fall by the wayside.

Figuring that I had enough time to snag a bun and cup of coffee, I made my way into Joe’s, silently deciding on exactly what it was that I would get. A light jingling sound from above the door caught my attention. Joe had set a bell next to the door since the last time I had been in here. It certainly caught his attention and Joe looked up and caught sight of me, his face splitting in a wide grin.

“Twilight Sparkle,” he called out in a deep, husky voice. I had always liked the sound of his voice. It was not quite gruff, but hinted at a strong male presence. Far deeper than my brothers, here was a man who had lived through some tough times and made it out the other end. “Fancy seeing you here. I haven’t seen you since that desert competition. Hows life been treating ya?”

“Oh, pretty good, Joe, just the usual. Study, research, learning about friendship,” I said back, sitting down on one of the empty stools up near the front of the shop where I could take a look at what was on offer. There was a jam berliner that looked divine.

“Business as usual then,” he said with a smile. “You just in town for the day?”

“I think so,” I replied. I wasn’t quite sure how long I was going to be here, to be honest. The princess’s letter hadn’t been very specific about what she actually wanted to speak to me about, just that it was important.

Joe seemed to notice something. “Oh, where are my manners? What’ll it be, miss Sparkle?” he seemed a little embarrassed that he had forgotten to ask me right away if I wanted anything.

“A cup of Chai blend, the Zebracan stuff if you have it please, oh and that jam ball berliner as well. How much is that?” I asked, reaching into my purse to grab some bits.

Joe shook his head, “put that away. You know your money’s no good here; not since you helped me get first prize.” He reached in under the counter and grabbed the jam ball with a pair of tongs before sprinkling a little confectioners sugar over it and passed it over to me. “One Chai coming right up,” he said before turning to work his drinks machine. It was nice to watch him work. They say that it is a joy to behold a master at work in their chosen field, and watching Joe was no different. He handled the cups and hot water with ease, mixing in the exact amounts of ingredients for each drink without the need for measuring; he knew exactly how much was needed through instinct alone.

Within a few moments, he had finished up making my drink and he brought over the steaming beverage. His expression darkened slightly when he saw me go for my purse again. “I mean that, Twilight. You have been a loyal customer here for as long as I can remember. This ones on the house.”

I took a heavy inhale of the steam wafting from the top of the cup, relishing the spicy mixture. It smelled delicious, but it was just a little bit too hot to drink right away. Still, I supposed, that was the way that coffees and teas should be served; it helped to lengthen the moment out, allowing one to savour the taste for longer. Looking back to Joe, I gave him a true smile. “Thanks, Joe.”

Joe leaned forward and gave me a quick, playful tussle of my hair. Joe was one of only a handful of people in Canterlot whom I could really call a friend. His late night coffees had steered me through more than one emergency cram session. “Don’t mention it kid,” he laughed slightly before turning serious, “I mean that, don’t mention it. Don’t want word getting around that I’m giving out freebies, else everyone would be wanting some.”

Joe gave me one last smile and returned to his duties behind the counter. Several other people had walked in and were eying a pair of kitchener buns with eager looks. I saw Joe move over to serve them and I turned my attention to the bun before me. Taking a quick bite out of it, I felt the molten jam leak out onto my tongue. It was heavenly, so sweet with just the right about of fruit bits still lingering to give it a little bit of consistency. It was clear that Joe had just made this particular one this morning.

Putting the bun back down onto its plate, I reached into my bag and pulled out the letter that the princess had sent me. It wasn’t a particularly big letter, not much more than a few lines, really. But in those few lines, Celestia had managed to pose up some significant questions. Idly tapping a spoon against my cup of Chai, I read through the letter one more time, trying to find some hidden meaning or clue as to what it was all about.

To my faithful student.

It has recently come to my attention that I have made a grievous error in regards to your education. There is something that I was reluctant to teach while you were still so young, but have also neglected to teach you now that you have reached adulthood. While I am confident that you may have learned much of what I have missed out on your own, I must endeavour to ensure that this oversight is correct as soon as possible. Please make your way to Canterlot on the next available train. I have made space in my schedule to see you at 11.00 am.

If you are unable to meet with me today, please have Spike send a reply at your earliest convenience. Otherwise, I will await your arrival at the castle.

Your eternal friend and mentor
Princess Celestia Alicorna.

I scanned the letter again, hoping to find something that I had missed, but there was nothing to find; just some vague references to something that Celestia hadn’t taught me because she thought that I was too young at first. That covered a lot of topics, but I couldn’t find any gaps in my education that could really fit in well with what she had just told me.

Shrugging, I put the letter back in my bag and picked up my Chai. It had cooled slightly and I took a quick sip, letting the hot spice and cinnamon flavours fill my mouth. Zebraca growers had recently developed several new blends that were becoming very popular with the upper classes of Canterlot society, and if this cup was any indication, it was a reputation that was well deserved. I grimaced a second later though; the drink was still too hot for me, and I nearly spat it back out. I swallowed it though, and the hot liquid left a warm trail all the way down to my stomach.

Waving a hard towards my face to cool me, I put the cup back down and returned to working on the jam ball. The cool feeling of the jam, felt soothing against my throat, and I decided to just wait for a little longer before trying the scalding drink again. Instead, I turned around and decided to take a look at the people in the café, in case I knew anyone there.

There were plenty of people sitting down or walking past the windows; a café is a good place to just sit and watch the world go by. A taller man in a waistcoat and top hat walked past, followed by an equally tall woman, very fair haired and glowing with beauty as she carried several filled shopping bags, each one bulging with clothes. It was a noble I had met a few times, Sir Fancy Pants, or something like that. We had met at court a couple of times, but had never been formally introduced until we had crashed his garden party last year. I could remember him not having any idea who I was, even when I introduced myself as the princess’s student. His wife, or was it his girlfriend had though, and she had given me a sly wink afterwards. I could almost remember her name; it was Fleur something.

She must have seen or felt me staring as, just as she was about to round the corner, she turned to look into Joe’s and she locked eyes with me. She gave me a short smile before she vanished out of sight. I watched her go, and I decided that I was really going to have to make an effort to get to know those two. It was expected of me, being the student of Equestria’s monarch, and I had received more than one dinner invitation over the course of my life. I had to figure that the princess had some kind of plan for me; my little sabbatical in Ponyville couldn’t last forever after all. Eventually I would have to return here and take my place at court.

A light ding from the corner of the shop caught my attention and pulled me out of my reverie; a grandfather clock had just struck 10:30. I hadn’t realised just how late it was getting, and it would take me a goog fifteen minutes to reach the castle from here. I hastily stuffed the remainder of the jam ball into my mouth, and followed it up with the Chai, which had thankfully cooled down enough that I could scull it down. It was a pity to waste such a good drink, but I didn’t have the time right now. Maybe I could stop for another one on the way back and enjoy it properly.

With a quick nod to Joe, I got up from my seat and turned to dash for the exit. It would take a brisk jog to get to the Castle with enough time to make it look like I wasn’t running late, but I knew Canterlot like only someone who had been born there could. My brother and I had spent many years chasing each other through the side streets and alleys and I knew all of the best shortcuts, even if it meant going through some lest than reputable areas. I wasn’t worried about that though, I knew how to defend myself and I carried a whistle and can of pepper spay in my bag. More than one would be rapist or kidnapper had received a swift blow to his family pride, followed by a macing.

After about ten minutes of not-quite-jogging, not-quite-walking, I reached the main plaza of Canterlot. This was where most of the markets and vendors would set up on the days when the markets were open, and it afforded me a great view of both the castle rising up above the city, perched as it was on the side of the mountain, and out over all of western Equestria. I knew that on a clear day, I could just make out the wide green fields that were Applejack’s apple farm and maybe see the top of the Ponyville town hall. Today however, there was a light fog covering much of the lower regions, and Ponyville was blanketed behind that. Canterlot was high up enough that it was unaffected by most fogs, though it wasn’t immune to things like rain or wind.

Slowing to a normal walking pace, I checked my clothes to make sure that I was presentable and marched on towards the main entrance of the castle. Several guards, resplendent in their golden armour nodded to me as I passed the main gate; almost all of the guards that had been assigned to the palace either knew who I was by name, or recognised my face. One of them held up a hand to block my way though. I didn’t recognise this guard, so he must have been a new recruit who felt that he had to enforce every rule by the book.

“Stop, citizen. None may pass by here without identification and an appointment,” he called out a little louder than was necessary, clearly hoping to impress someone with his adherence to the rules.

I shrugged and pulled out my I.D. It had been years since I had been carded, and I counted myself lucky that I had bothered to bring it at all, though if I had been rejected I could have easily just gone to another entrance and found one of the guards who knew me. The guard looked at my photo and back to me again several times, clearly trying to find some kind of impostor or fake. He must have been a greenhorn who was hoping to make a big break on his first posting.

Behind him, another guard, one whom I knew well enough to be on a first name basis with walked out of the main guard house, an annoyed expression on his face. He marched over to the recruit guard and grabbed the I.D. out of his hand before passing it back over to me. He addressed the younger guard, “Hot Flame, what do you think you are doing?”

The guard, Hot Flame, replied with what I assumed to be the exact words of the training manual that Shining Armour showed me once, “All visitors must have their identities confirmed by a member of the royal guard prior to entry into the royal palace, Sir.”

“Well not this one. Don’t you know who this is, kid. That’s Twilight Sparkle, the princess’s most trusted student and protégé, and she has an appointment.” He turned to me with an apologetic look on his face, “Sorry about that, Twi. You just go on in; I’ve got to deal with this new blood out here. I reckon that a couple lashes ought to set him straight.”

I was horrified to hear that he was considering corporal punishment. “No, don’t do that; he was just following proper procedure after all.”

The senior guard laughed at my comment. “Jeez, Twilight. It’s just a joke. The princess has outlawed whippings for nearly twenty years, except in cases of high treason, and I don’t think that this quite qualifies.”

I relaxed, relieved that Hot Flame wasn’t going to be hurt. Hot Flame also looked relieved, and he gave me a sheepish ‘sorry ma’am,” before returning to his post by the gate. With a quick wave to the pair of them, I set off for the actual palace. It was nearly eleven, and I didn’t want the princess to think that I was going to be tardy.

I made my way up the stairs, heading for the throne room when the princess’s chamberlain, a pretty woman called Raven pulled me aside. I new Raven fairly well, though we had never socialised before; she had been Celestia’s personal assistant and chamberlain for as long as I could remember. Rather than send me into the audience room as I normally would have, she directed me to head towards Celestia’s bedroom, indicating that the princess would meet me there.

“She told me to tell you that you are to have a private audience with her, and that she will meet you in her quarters. She is just finishing up a meeting with Ambassador Gryphon and should be with you shortly,” Raven said before returning to her desk to deal with a mountain of paperwork that had arrived that morning.

I nodded and headed deeper into the depths of the castle. This wasn’t the first time that the princess had asked me to come to her bedchambers, so it didn’t seem particularly odd to be going there. I knew the way like the back of my hand and it wouldn’t take me more than a minute or two to get there. On the way, I passed several maids and stewards, many of which gave me a smile or a nod. A guard by the name of Constant Vigil was stationed outside of Celestia’s bedroom, and he stood aside to let me in without a single word. Clearly he had been informed to expect my arrival. I had always liked Vigil; he was a gruff, no nonsense guard when he was on duty, but there was a softer side to him when he wasn’t on the clock. I had heard through the grapevine that he had recently gone through a bitter divorce to a woman who had apparently only been after an introduction to Canterlot high society. She had wanted to rub shoulders with the elite of the elite, not realising that they didn’t want to rub back. When it had become clear that she wasn’t going to get what she wanted out of their marriage, she had filed for divorce and taken nearly everything.

I thought that it was a pity that Vigil had gone through that. He was kind and handsome; any girl should consider themselves lucky to land a man like him. He had watched out for me a couple of times, when my brother hadn’t been available.

He gave me a smile, but didn’t say anything. I returned the smile and he opened the door to Celestia’s bedroom, allowing me to enter without a fuss. As soon as I had entered, he closed the door again, and I had to assume that he had turned to face out again, a silent sentinel to bar access to everybody who didn’t have a reason to be there.

Pushing thoughts of Vigil out of my mind, I looked around the room for the princess. Princess Celestia’s rooms were opulent in the extreme. The floor plan was larger than some houses, and everything was dripping in luxury. The covers on the bed were pure silk, imported from across the seas; the floor was tiled in exquisite marble. A massive pair of windows filled one entire wall, allowing sunlight to stream in. they were arranged as such that Celestia would wake up every morning drenched in sunlight, which she said rejuvenated her in ways that simple sleep couldn’t.

I looked over all of her luxury before noting one significant thing – That Princess Celestia was not present. “Princess,” I hesitantly called out, “Are you in here?” It was possible that she hadn’t finished up her meeting with Gryphon. The old man did love to hear himself speak.

There was a small bang from inside the bathroom, and a second later, Princess Celestia’s head popped out from around the door. “Twilight!” she called out, smiling broadly, “I wasn’t expecting you for another few minutes, I’m just finishing getting ready. Take a seat and have a drink. I shouldn’t be more than another minute or so.”

I did as the princess bade me, walking over to her well stocked private bar and picking out something for myself. It was a little early for me to be drinking, but I shrugged; it had to be five o’clock somewhere after all. The princess had long since stopped forbidding me to drink, and I quickly made a gin with tonic for myself, and set about creating a banana daiquiri for Celestia; she loved bananas and anything that could be made from bananas.

I was about to take the drinks over the couch in the centre of the room to wait for the princess to finish up with whatever she was doing when she walked in herself. If I hadn’t already had the drinks on a flat surface, I was sure that I would have dropped them right then. Celestia looked gorgeous. Her hair had been carefully styled so that it cascaded down her back, each of her multiple colours a perfect line. As she passed through a beam of sunlight, her head shone with prismatic perfection. Aside from her hair however, it was her outfit that caught my attention, or rather, her lack of an outfit.

Celestia was wearing what could generously be called lingerie, and ungenerously be called nothing at all. While technically she wasn’t actually revealing anything, her costume left nothing to the imagination. Thin silks wrapped around her upper body, coming together to cover her ample D-cup breasts, though much of her cleavage was still showing to those who cared to look. Similarly thin material formed a set of panties. A metal collar was attached to her throat, with copper and brass chains connecting it to a similar ring adorning her waist. While she was not nude, the entire ensemble was clearly designed to highlight the fact that she may as well have been, save for a few square inches of fabric. The amount of skin on display was almost obscene, and I instantly averted my eyes from looking at her.

Celestia noticed my reaction and she paused, seeming to notice exactly what it was that she was wearing. From the corner of my eye I saw her smile and keep on walking towards me. A hand reached out to pat me on the shoulder, and I turned to look my mentor square in the eye, trying hard not to let my gaze drop down south.

The princess smiled at me and took the drink I had prepared for her from my hand. She took a quick sip and motioned for me to have a seat. I moved almost robotically, trying hard not to look at my teacher’s body; a difficult prospect given how much of it was on display at that very second. Despite being nearly fifty, Celestia didn’t look a day over thirty, and had retained a very slim hourglass physique. Long slender limbs matched her waist perfectly.

She gave me a genuine smile before following me to the couch and sitting down opposite me. Once we were both seated, she spoke, “Twilight, I’m sorry. I should have mentioned this,” she indicated her attire, “but I had just finished up a meeting with Ambassador Gryphon, and you know the old man – perverted as they come. Show him a little flesh and he will agree to anything. I may have gone overboard today, but we were talking about trade agreements and I had something I wanted to push through. Needless to say, I got it.”

I didn’t say anything; I was still trying to avoid looking directly at her.

Celestia hmmed at that, “Twilight, you can look if you want. This is going to be a very awkward lesson if you can’t even look at me.”

The mention of a lesson cleared my mind and I turned back to face Celestia. She smiled at me and leaned back in her couch. Now that I was looking, I could see that she had a fine layer of defined muscle on her chest and stomach, not enough to call a six-pack, but plenty to show that she took exercising seriously. My own body was nowhere near as toned as hers was. I’ll admit to being a little on the chunky side at times, but I certainly wasn’t fat.

“So what is this about, princess?” I asked once I felt I was sure I could speak without tripping over myself. “You mentioned something that you never taught me before.” I could feel myself growing excited at the prospect of learning some long forgotten secrets or lore.

“Yes, I suppose I did,” Celestia said absently, idly playing with the straw to her daiquiri. “Twilight, how much would you say you know about sex?”

The question caught me off guard. I hadn’t been expecting something like that. If this was what the princess had wanted to teach me, she had forgotten that she had already taught me about this. She even had the surgeon general of Canterlot teach me about reproduction when I started my monthly cycle.

“Uhh, I suppose I know a lot about it,” I said, not quite sure what she wanted to hear. “I know all about males and females having coitus to procreate, and about how a woman has to go through her monthly reproductive cycle once she reaches puberty.”

Celestia raised a hand to forestall my going into lecture mode, and I fell silent. She shook her head a little, “No, I don’t mean about reproduction. I still have your fifty page essay on the female reproductive system somewhere. I know that you know that. I’m asking what you know about sex, the act of making love, being intimate with another.”

“Well, I suppose I’ve read about a couple of positions before, but I’ve never had another person or the desire to try them out. It was purely an academic investigation.”

Celestia sighed briefly, “See, this is what I meant when I said I had neglected your education; you don’t see it as anything other than something to be studied. Twilight, how old are you?”

That was an odd question; the princess knew exactly how old I was. “I’m twenty one, your highness.”

“Have you ever had a boyfriend?”

I had to shake my head at that. I had never had a boy I thought of in that way. Spike was the closest boy in my life, but he was my adoptive little brother and I didn’t think of him like that.

“How about a girlfriend? I won’t judge you if you have.”

Once again, I shook my head. Me having a girlfriend? I wasn’t interested in girls like that.

Celestia put her drink down on the table, dragging a coaster under it as she did so. “Last question then. Have you ever masturbated?”

“Princess!” I exclaimed. This was getting just a little too personal now and I could feel my cheeks begin to blush.

“Answer the question, Twilight. I promise you I am going somewhere with this.” Celestia was insistent.

“I’ve never… masturbated,” I finally said. Even the word felt dirty in my mouth.

Celestia sighed, “And that is the problem, Twilight. I’ve spent so many years teaching you about everything I know, but I never taught you to understand your own body. You are twenty one and you still have never experienced the pleasure of sexual congress, or even of your own hand. I’ve seen the reports, Twilight; girls younger than you are not only having sex, some are even mothers now.” She lifted her drink up again and drained whatever was left in it. I glanced at my own drink, nearly untouched and took a quick gulp.

Celestia gave me a level stare, “This is what I called you here for, Twilight. I am going to teach you about the wonders and pleasures of your own body. It was my fault that you never found out before; I was too focused on your education that I never saw you develop as a woman, so it falls to me to teach you now. I promise you that when you leave here tonight, you will be a whole new woman.”

I wasn’t sure I liked where this was going. Was Celestia really telling me that she was about to make me have sex with someone, or to force me to masturbate in front of her. I wasn’t a total prude, I knew of the pleasures of sex; that orgasm was supposed to feel incredible. I just hadn’t ever found the right person with which to try, and trying it with myself had seemed so… dirty, that I had never bothered.

Celestia reached up and fiddled with something behind her back. A moment later, she undid the collar around her neck and the few strips of cloth covering her breasts fell away, revealing her massive mammaries to my eyes. “Today, you are going to learn about your body,” she said as she got to her feet. Her breasts swung freely as she moved, drawing my attention. I wasn’t sure if I should be looking, but I couldn’t look away.

Celestia caught me looking. She delicately licked her lips, and ran one of her hands down the cleft of her breasts. “It’s alright, Twilight. The female form is beautiful. You can look if you want; even touch.” She moved over to me and picked up my hand before placing it over her right breast. I could feel her nipple hardening under my palm. “Squeeze it,” Celestia commanded, “feel how soft it is.”

My hand curled around her breast almost instinctively. Celestia’s flesh was soft and smooth. It felt odd to be touching her there, but not unpleasant. Timidly, I brought my other hand up and cupped her other breast. Celestia moaned softly as I began to squeeze her breasts. “Hmm, that’s right, Twilight. Fondle my bosom. Feel how soft they are.”

They were very soft, and squeezing them felt strangely right. I could feel my own nipples begin to strain against my shirt, pressing forward to leave an imprint against my bra. Celestia noticed and raised her hands around mine. Slowly, she began to undo the buttons that held my shirt in place; each button coming free with a pop until only one remained. It strained, clearly unable to take the strain. I knew that my breasts weren’t the largest; both Rarity and Fluttershy had larger breasts than I did, but they weren’t tiny either. I liked to think that they were well proportioned for my body, but I had also never really given them much though; they had always just kind of been there.

With one last snap, the final button came free and the princess slowly opened my shirt, revealing my nearly bare chest. Smirking at me, she traced under the curve of my breasts, sliding her finger along where the bra met my skin. I shuddered as I felt her fingers sliding up against me; it was the first time in my adult life that I had been touched there by a non medical professional, and they had certainly never touched me like this. Celestia’s fingers were soft and delicate. They seemed to know just how to tease me and left tingles behind them. I was sure that Celestia could see goosebumps forming in the wake of her fingers.

The feel of Celestia’s fingers caused me to redouble my efforts on her own breasts. Both of her nipples had hardened to full length, and I was massaging them with some force now. Every few strokes, I would tweak her nipples or push her breasts together. It seemed the natural thing to do and every time that I did, she would sigh or moan slightly, indicating that I was doing a good job.

Focused as I was on my mentor’s body, I didn’t notice her hands slide around my back until I felt her grab the clasp that was holding my bra on. With a deft motion, she unhooked it, and my bra came free. I tried to cover myself, but Celestia’s hands caught mine and pulled them down by my side. Holding my hands there, she slowly reached in and grabbed the bra between her teeth, pausing for a second to lick my newly exposed skin.

“Eeekk,” I started when I felt her tongue touch my breasts. Celestia giggled and pulled the bra away, fully exposing my body to her eyes.

“Twilight, you are beautiful. You should be proud of your body,” she said as she looked me up and down. I blushed at her words, burning and even fiercer red than before; I had been complimented before, but never like this. Celestia motioned to my shirt; I was still wearing it and it hung loosely around my arms. “Take that off, Twilight. Let me see the rest of you.”

I did as she bade me, and removed my shirt and flung it over to the side of the room. Celestia quickly followed with my bra. Soon I was sitting on her couch, wearing nothing but my skirt and socks. As I moved around however, I became aware of a tingling feeling between my legs. It felt warm and slightly damp. Celestia must have seen it too, as she reached in and spread my legs open. She wasn’t forceful, and I was sure that if I had resisted she would have stopped. I didn’t though, and soon she was looking at my panties. I unhitched my skirt and slid it off to reveal that there was a large and rapidly expanding wet patch on my panties. My hands instantly went to cover it, but once again, Celestia stopped me.

“You need not be embarrassed, my faithful student. This is a natural part of your sexual drive. If anything, I would be offended if you hadn’t begun to moisten by now,” Celestia purred. She leaned back on her side of the couch to reveal that she had a matching damp spot on her own panties. “This indicates that your body is ready for sex.” She paused for a moment, before leaning over to a small box on her table. “Speaking of which, I think that we are missing a vital participant for this lesson.”

Celestia pushed down on a button on the box before leaning in close to it. “Constant Vigil, a matter has arisen that requires your attention. Would you please step into my chambers?” She shut off the box and reclined into the couch, letting her legs spread open before pulling me over to join her.

A few seconds later, the door to Celestia’s bedroom opened and Constant Vigil walked in, looking around for anything that was out of place. His gaze came to rest on us, and in a moment he realised that he was looking at two half naked women who had clearly been enjoying each others company moments before. As he locked eyes with us, time seemed to freeze.

None of us spoke, or even moved. We all just either stood or sat there, looking at each other. I wasn’t sure what was going on, or what Celestia had planned for this guard.

A moment later, time sped up again, and in the silence of Celestia’s private chambers, we could all hear the soft ‘ding’ coming from the lower half of Constant Vigil’s armour. At the sound, he turned away. “Ma’am, you are not decent. I will come back later.”

Behind me, Celestia’s voice rang out soft but firm, “Nonsense, Guard Captain. This is the matter for which I have called you. I have chosen to give my student a practical lesson in the pleasures of sex, and I require the aid of a virile stallion of a man in order to give her the necessary instruction. I would consider it a personal favour if you would provide such instruction. A moment later she added coyly, “who knows, you may even enjoy it.”

Vigil’s face turned back to us. His gaze swept over our bodies, and I could tell that he was considering the potential implications of what was being asked of him. In the end though, he made the decision with the brain in his pants. Swiftly he nodded and walked over to where we were standing. I noticed that he was walked slightly bow legged, and I could take a guess as to what the ding noise earlier had been.

Once he reached us, Celestia extended a hand and slid it up the seat of his pants, lingering a moment when she reached the bulge visible between his legs. Vigil grunted for a moment, but he didn’t move away.

Celestia grinned at him, clearly pleased with what she saw. “Captain Vigil, you may disrobe and join us at your leisure.”

His decision made, Vigil needed no further motivation, and in moments his armour clattered to the ground, leaving him clad in little than an undershirt and pants. I could easily make out his toned body, and highly prominent bulge poking out from between his legs. Just looking at it, I could feel the wetness between my legs increase.

Celestia seemed pleased with him as well. I could hear her breathing deepen as she looked at the bulge in his pants. Wasting no time, she reached out and grabbed the waist band of his pants and pulled them to the ground. The pants snagged on something for a moment, and then suddenly, Constant Vigil’s penis came bobbing into view. He was already fully erect and he appeared to be leaking clear fluid from the tip. I felt a little intimidated at the size of it; I would barely be able to close my hand around it.

Beside me, Celestia leaned forward and whispered into my ear, “Just watch for now, Twilight. You will get your chance later on.” That was fine with me, as I wasn’t sure what to do with Vigil’s impressive length at the moment anyway.

Celestia guided me onto the floor next to Vigil, where I would have a clear view of what was to come. Once I was comfortably seated, Celestia looked up at Vigil and gave him a sincere smile. “Equestria appreciates your devotion to duty, Captain Vigil. I think it is time that I show you a little of that appreciation.” With that, she lifted up Vigil’s penis and gave the underside a long slow lick all the way to the tip.

Vigil tensed up as Celestia’s tongue dragged up to his crown, and once she reached the tip, she opened her mouth wide and engulfed Vigil’s length. I could only watch as my mentor took her guard’s hard length into her mouth and keep on going. With one smooth motion, she had swallowed nearly half of his penis, and I could see her throat open up to accommodate more.

Vigil groaned as he felt Celestia start sucking on his penis; he clearly was enjoying it. Soon the princess had reached the root of Vigil’s shaft; her lips were touching the bottom on his penis and her head was pressed up against his navel. I could make out a deep bulge in Celestia’s throat and could only guess as to how far down she had swallowed him, and with apparently no effort. She had clearly done this before.

I had heard about people performing this kind of sex act with a partner before; fellatio and cunnilingus I remembered they were called, but I had never expected that it would be the princess who would show them to me. I felt dirty watching them, and, to my shame, more than a little turned on. It wasn’t that I didn’t like the idea of sex; it was more that I had just never found the right person to try it with.

After a few seconds, Celestia pulled back off of Vigil and released her grip on his length until only the very tip remained inside of her mouth. I could see that his shaft was now quite slick with her saliva. Taking a moment to inhale a lungs worth of air, the princess began to smoothly bob her head over Vigil’s penis, engulfing it to about half way before pulling back again until only a little remained in her mouth. Her breasts wiggled about as she thrust her head down on his shaft. I could see that one of her hands had moved its way down her body, and I followed it with my eyes to see that she had pulled her panties to one side and was rubbing two fingers against her own glistening vagina.

At that sight, I felt my own vagina give a powerful twitch, expelling a few drops of lubrication. Timidly I brought up one of my own fingers and pulled my own panties to one side, exposing myself and touched a digit against my own labial lips.

A sudden jolt of pleasure ran through my body as soon as I touched myself. With a start, I pulled my hand away and nearly slammed my legs together out of pure reflex.

Celestia saw the motion and turned to look at me. She could see my finger moistened with my own juice, and my panties pulled over to the side and she could guess what I had just been trying out. She let Vigil fall out of her mouth and turned to face me. Vigil’s helmet was flushed a deep purple and he appeared to be twitching every few seconds.

With a kind smile, the sort of which Celestia had always given me when I had done something wrong, Celestia leaned over to me and gently pulled my legs apart again. “Don’t be embarrassed, Twilight. What you just felt is natural and a wonderful thing. It may seem odd the first time, but you will grow to love it in time.” With a gentle hand, she picked up my fingers and placed them over my lips again. She didn’t rub it for me, and she quickly returned to servicing Vigil once I was in place again. “Now, where were we?” she asked the guard. “Oh, Right!” she answered her own question, gripping his slick shaft in one hand and wrapping her lips around the head once again. Watching them, I could see Vigil’s face contort as Celestia resumed sucking him off. It didn’t look like he was in pain though, going on the massive grin on his face.

Timidly I tried touching myself again; this time I was ready for the jolt that accompanied it. Rubbing my fingers against my outer lips felt odd, but there was also an undertone of pleasurable tingling behind it. My fingers quickly became coated in my own juices and the skimmed over my flesh smoothly; almost as if they had a will of their own. While that was happening, my other hand was exploring others areas of my body, running itself over my breasts and sliding down my stomach. Occasionally I would pause to tweak a nipple or grab a handful of my breasts and squeeze. All the while, there was a pressure building in my loins; a pressure that I had never quite felt before. It almost felt like I had to pee, but that wasn’t it.

As I kept rubbing myself, the pressure continued to build. Slowly my movements became more erratic, and jerkier, until with a sudden cry, I brushed a finger against my clitoral hood and the dam holding back the pressure burst and it came flooding out. Bright sparks danced behind my eyes and I felt myself lock up.

My body moved without my control, twitching and pulsing as wave upon wave of searing pleasure burning its way through me. I could feel my vaginal muscles spasm and contract; the hand that I had been stroking myself with was instantly covered in my arousal. My other hand had grabbed a hold of my left breast and had pushed it hard against my body. I screamed; a high piercing cry that I was sure could be heard throughout the castle.

Just when I was sure that it would never stop and I was going to be stuck like this forever, I felt my body relax. Slowly my limbs went limp and my body stopped twitching. I fell back onto the floor of Celestia’s chambers, utterly drained of all energy, but strangely content. I felt warm, even on the cold stone of the floor.

As I lay there, a shadow passed over me and I looked up to see the princess kneeling above me. She held out a hand and I lifted one trembling arm to meet hers. She quickly grasped it and pulled me back up to a sitting position, one of my hands landing in a puddle of what I realised had to be my own orgasmic fluids; there was more on the ground that I had though could have been possibly produced, and my thighs were coated in it. Constant Vigil was still standing stock still over near the couch. I could make out that he was still at full attention in more ways that one.

“Did you enjoy that?” she asked me once I had my breath back. I could only nod at her. My throat had become very dry for some reason. “That was your first orgasm, Twilight. It is something that you have been missing for a very long time.” She turned her attention back to Vigil, who was looking down at us with some concern. He now looked like he was in some discomfort, but he held his hands behind his back, refusing to relieve himself.

“Now I think it is time that I help our guest out with his rather hard problem.” Celestia said with a wink to me. In one motion she waddled back over to were Vigil was standing and once again took his member into her mouth. This time it was different though. Where before it had been slow smooth strokes, this time Celestia’s motions were quick and jerking. She moved with no grace but pumped her head over the tip of Vigil’s penis while stroking the lower half with both of her hands.

Vigil’s face was a mix of pleasure and pain, and in a sudden surprise move, I saw one of Celestia’s hands let go of his penis and snake around to his back side. Half a second later, Vigil gave a sudden cry of surprise and I saw his length twitch hard in Celestia’s hand and mouth.

Celestia instantly released Vigil from her grip and grabbed the empty glass that had held her drink. She held it up to the tip of Vigil’s penis, and a moment later, a gush of white goo burst forth from his tip, landing in the glass and filling the bottom of it quickly. The first gush was quickly followed by a second, and then a third. Creamy white liquid continued to flow into the cup. I knew what it was that Celestia was collecting; I had learned basic anatomy when I was seven. Semen pooled in the glass until eventually, Vigil’s penis began to deflate and the spurts stopped, leaving a few last drips to dribble out of his tip.

Celestia gripped Vigil’s member and gently squeezed it, pulling out a few last drops and filling the glass to about a third full. Once she was sure that she had all she was going to get, Celestia released Vigil, and the guard fell back onto the couch, clearly spent. With a grin to me, Celestia raised the glass to her lips and quickly swallowed several mouthfuls of Vigil’s sperm. I couldn’t believe what I had just watched.

“Princess? What are you doing?” I asked. I had no idea that she would do such a thing. “Are you…swallowing his semen?”

Celestia lowered the glass, leaving another mouthful or so still collecting at the bottom. With a quick wipe of her tongue, she licked off a few flecks that had remained on her lips before answering me. “Yes I am, Twilight. I am swallowing his semen, gulping his jizz, drinking his cum if you want to use the common parlance. You see, there are three main reasons that I just did that. First, cum is high in protein and iron, as well as other minerals while also being very low in fat, making it a very good nutritional supplement. Second,” she paused for a moment to dip a finger into the collected jizz before rubbing it into her breasts, “It is as good, if not better than most of the current skin creams. How do you think I have maintained my youthful complexion?”

I had to admit that I didn’t know. I had always just assumed that she took good care of herself.

“Thirdly,” she continued, her grin darkening slightly, “I just really like the taste.” With that she upended the glass and swallowed the remainder of Vigil’s seed with obvious satisfaction. I couldn’t take my eyes off of her and what she was doing. Next to me however, Vigil’s shaft began to rise up again; clearly he had been aroused by the sight of the princess enjoying his cum.

Celestia saw him begin to rise up again, and she put her glass back on the table before slinking forwards with a cat like expression on her face. Reaching Vigil, she gently stroked his member, aiding in returning him to full hardness. Constant Vigil twitched under her touch, evidence of how much pleasure he was receiving from her attention. Once he was near full hardness again, Celestia leaned forward and took him into her mouth again, bobbing her head and sucking hard. The elicited a number of moans from Vigil, who looked like he was in heaven right then.

Before he could reach orgasm again, Celestia pulled off of Vigil and turned to give me a smile. I could see small beads of his semen on her tongue and swallowed them gratefully before licking Vigil clean. Once she was done, Celestia got up and pulled Vigil to his feet by his rock hard length. Vigil obeyed without a word.

“My dear Vigil, we have been neglecting the third member of this party,” Celestia said, turning to me, “How about we let her get a taste of your sweet pride?”

Vigil nodded once and guided by Celestia, he came to rest directly before me. His throbbing penis bounced with every step, and soon he was standing right before me, close enough that I could easily reach out and touch it.

I turned to look at the princess who motioned for me to grasp Vigil with my hand.

With a trembling forearm, and a pit of butterflies in my stomach, I reached out and grabbed hold of Vigil’s penis, encircling it with my hands and feeling its throbbing hardness for the first time.

Author's Note

You all asked for it - When are you doing a sequel to 'A Summer day on the farm?'
The short answer is that I am not. That story is done.

But that doesn't mean that other stories won't be told.

This is going to be a shorter story - only two chapters long and is meant to be how I see Twilight in my headcanon - Lots of potential, and great theoretical knowledge, but little practical experience. This translates over to the world of sex with her knowing the biology of sex, and having a basic idea about what it means but not having any idea about the actual practical aspects of it.

Who better to teach her than with a little bit of the ever popular Twilestia?

Chapter 2

I had never seen a penis this close before; not a real one at least. I had seen pictures of them in textbooks, but they couldn’t prepare you for the reality of the thing. Vigil’s penis bobbed and swayed freely before me, its thick veiny texture and bulbous purple head almost hypnotic. I wasn’t sure if I should reach out and grab it or run screaming from the room. In the end, it was Celestia who made the choice for me. Her hand came up and wrapped around mine, lifting my hand up so that I grasped Vigil’s penis. It was warm and throbbing in my hand; I would later swear that I could make out Vigil’s heartbeat through it.

Celestia guided my hand along Vigil’s shaft, slowly stroking it from the base up to just below the tip. Dribbles of sticky pre-cum coated my hand when I reached the tip. Vigil moaned and my hand moved along his shaft, so I assumed that I was doing something right.

“That’s right, Twilight. Slow and steady. Not too much force or pressure,” Celestia said as she moved my hand along Vigil’s penis. “Remember that the glands are very sensitive, so you have to take care when giving a hand job. Coat your fingers in his lube to reduce friction.”

Once she felt that I had gotten a smooth motion down, Celestia released her grip on my hand, leaving me to try and stroke Vigil on my own. Getting a firm grasp on him, I began sliding both hands along his shaft. Vigil was moaning and smiling absently, which I took as a sign that I was doing something right. Slowly, I began to increase the pace of my stroking; it felt like the right thing to do, and neither Vigil nor Celestia made any motion to stop me.

While I was giving Vigil a hand job, I took note of what seemed to please him. He appeared to like it when I brushed against the tip of his penis with my fingers, or if I brought a hand down to touch his hanging sac. I tried adding in the things he appeared to like more often and within a minute or two, I had my hand pumping up and down his shaft with ease, occasionally pausing to fondle his ball sac. A tart smell had permeated the entire room, one that I was sure was a mixture of all our arousals.

Soon, I could feel his penis twitching in my hands, and his pre-cum was dribbling out freely. Vigil looked like he did when Celestia had caused him to ejaculate, so I tensed up and waited for him to shoot out another load of his semen onto my hands.

A moment before it could happen though, Celestia pulled me off of Vigil’s length. He twitched hard, but nothing came out of his tip. He looked down at Celestia, clearly in discomfort at being denied his release.

“Soon, Vigil,” Celestia said, apologetically. “I don’t want you finishing up before it’s time. There is still much that Twilight needs to learn before we are done and I can’t have my teaching aide tire out just yet.”

Eventually, Vigil came back from the edge and he began to calm down. I could see his penis begin to shrink before my eyes. At which point Celestia quickly motioned for me to resume my stroking of it. I complied and grasped Vigil’s penis again. At once, he began to rise up again until he was once again at full mast.

Once he was ready to go again, Celestia came over to me, and put her hand up on my back. “It’s time for your next lesson, Twilight,” she said, slowly pushing me closer to Vigil, until the tip of his penis was just an inch away from my face. I could make out every vein on his shaft. “Having learned about giving a hand job, it is now time that you learned how to properly perform fellatio, though most people simply refer to it as giving a blow job, or giving head.”

I turned to look at the princess, unsure of what I should be doing. With a hand she indicated Vigil’s penis. “Remember what I did before? Open your mouth and swallow Vigil’s cock. Trust me, he will like it. You mouth is warm and wet, and that is two things that the nerves in a penis can distinguish very well. Suck on him and massage his length with your tongue. Just be careful not to scrape your teeth over him or bite down; those things can cause a large amount of pain if you are not careful.”

Hesitantly, I opened my mouth and leaned forwards over Vigil. A moment later, I felt him touch the edges of my lips as I closed my mouth around him. It was weird, having something like that half sticking out of my mouth; it felt slightly like trying to eat a whole carrot at once, and there was an urge to bite down and chew, but I remembered what the princess had just said. Instead I focused on using my tongue to swirl around the underside of Vigil’s cock, as the princess had just called it. The moment I touched the underside of his cock, I felt a drop of something very tart and strong touch my tongue. I realised that it must have been Vigil’s clear pre-cum that I was tasting. It didn’t taste bad, but it wasn’t going to be on my list of favourite things to eat any time soon.

A hand grabbed the back of my head and slowly, it began to pull me closer to Vigil’s abdomen. More of his thick cock began to fill my mouth until at nearly halfway, I felt him touch against the back of my throat. I convulsed and nearly began choking and the hand instantly let go. I quickly let Vigil slip from my mouth, drawing in several deep breaths and coughing hard. Vigil just waited patiently, while Celestia pulled me in close and stroked the hair out of my eyes.

“Don’t try to force it yet, Twilight,” she said calmly. I know you saw me take all of Vigil in one go, but you don’t have my experience yet. Just go as far as you feel you are comfortable with.”

Eventually, I stopped coughing and spluttering and managed to resume normal breathing. Once I was calm again, Celestia put my hand over Vigil once again. He had softened slightly during the break. She motioned for me to start sucking on him again. I did so, making sure this time to only take the head into my mouth. As soon as I did so, I could feel him spring back to like and harden within my mouth. The tart taste of his pre-cum filled my tongue again and I started to lightly suck on his tip once more.

Very slowly, I began to bob my head as Celestia had done, allowing fractionally more of Vigil to fill my mouth with each stroke. Soon I felt that I had hit my limit with about a third of his cock filling my mouth.

“Very good, Twilight. I always knew you were a quick study,” Celestia praised me as I continued giving Vigil head. Over time, my strokes became smoother and faster until I had reached a reasonable speed; blowing my cheeks out and swallowing him on the down stroke, and then sucking hard on the up stroke. Each pass teased out a little more of Vigil’s pre-cum onto my tongue and I had to admit that I was starting to enjoy the flavour. It was salty and now that I was used to it, it wasn’t as overpowering as I had first thought.

I could hear Vigil moaning nearly non-stop now and Celestia was whispering a constant stream of praise into my ear. I barely noticed any of it though, as like Celestia had, one of my hands had reached in between my legs and was stroking away at my clit with fervour. If this was what masturbation always felt like, then I was sorry that I had waited so long to try it out.

Vigil suddenly tensed up and I could feel his sac contract several times. “Twilight, I’m going to pop,” he groaned. I wasn’t quite sure what he meant by that and he didn’t elaborate. A second later, both of his hands grabbed the back of my head and he thrust deeply into my mouth.

“EEAAAGGGGHHH,” he moaned before I felt his penis twitch in my mouth. A moment later, I felt something warm hit the back of my throat, followed by another. It was warm and salty, with a consistency of half set jelly. It took a moment before I realised what it was; Vigil had just ejaculated in my mouth. I wanted to pull back and spit it all out, but Vigil had me held fast. With his dick nearly touching the back of my mouth, I only had one option if I didn’t want to choke. With a small shudder, I swallowed the seed down into my belly, feeling its slimy texture running down my throat and into my stomach.

Vigil’s hands fell away as he lost himself to his pleasure, and I took the opportunity to remove him from my mouth. His cock was still spewing cum and several spurts covered my face and breasts. Quick as a flash, Celestia latched her mouth onto Vigil’s tip and she eagerly swallowed the remainder of his seed.

I sat on the ground, stunned and now covered in semen. Some of it was still lingering in my mouth, and I swished it around a little. It was warm and had a strong salty aftertaste. It was like Vigil’s pre-cum, only stronger. I wasn’t sure if I liked it or not; it was so alien to my tastebuds that I had no point of reference at all.

Before me, Celestia finished sucking out the last of Vigil’s sperm from his penis, and with a hunger that I had never seen before in her eyes, she turned to me. In a moment, she had pushed me to the ground and straddled me with an agility that I had not know she possessed. Before I could try and push her off, Celestia leaned forward and began licking the cum from my breasts. As her tongue dragged its way over my nipples, I decided that I didn’t actually want her off of me and my hands came up to try and pull her in closer.

Celestia seemed to know what I wanted, and she quickly changed tact and started sucking on my erect nipples as a baby would. If felt so good that I nearly came right then. A small part of my brain appreciated the situation as I dry nursed my mentor and princess of the land. Celestia’s tongue swirled around my areolas in much the same way as I had to Vigil’s penis a few moments before.

Not breaking her contact with me, Celestia dragged one of her hands down my body, lightly brushing against my stomach and circling my other breast. I shivered at her touch and pulled her even harder against my body. Her hand came to a rest just above my clit, her fingers lightly brushing against my hyper sensitive lips. In one deft motion, she hooked her finger under my soaking panties and pulled them free from my body until they were down around my ankles. With a flick of my legs, they joined the pile of my clothes in the corner, leaving me clad in only a pair of socks.

Celestia quickly moved her hand back to my body and I felt her fingers gently probe the very tip of my opening. She didn’t force them in, though I was so wet that she could have had no problem. Instead, she detached from my nipple and turned to look at me.

“May I?” she asked, pausing her licking and sucking so that I could concentrate.

“YES!” I screamed. I had never inserted anything into my vagina before, but right now, I wanted the princess’ fingers in me more badly than I had wanted anything before. With a flick, I spread my legs apart, allowing Celestia as much access to my body as she could possibly want.

“I love you, Twilight,” Celestia said before she plunged a finger into my soaking hole.

Pure pleasure lit up my brain as Celestia’s finger parted my lips and entered my body. There was a slight stinging feeling, but that was quickly overtaken as my second orgasm of my life rippled through me. I could feel my vagina clamp down on Celestia’s finger, gripping it as if I never wanted to let her go and I was dimly away that Celestia had returned to sucking on my nipple. I had no idea what Vigil was doing, but I didn’t care. Right now, I wouldn’t’ have cared if Shining Armour was watching me; all that mattered was this feeling and making it last as long as I could.

Celestia plunged her finger deeply into my body, each thrust matched by a gentle ‘schlick.’ The feeling of something moving inside me was bizarre and unlike anything I had ever felt before. There was some pain, but it also just felt so good.

“Oh, Twilight. You are so tight; I love it,” Celestia purred next to me. Her finger was touching the inner me while her other hand caressed the outer me. It was intense, but I was loving every moment. I didn’t want the moment to end, but eventually, Celestia pulled her finger from within me and held it up to the sunlight streaming in through her window. I could see that it glistened with my juices and Celestia brought it up to he mouth, extending her tongue out and liking up the length of her digit; tasting my juices. She licked her lips, “Mmm, you are so very sweet, Twilight.”

I propped myself up on my elbows and looked over to her. “I never thought that it could feel so good having something inside me.”

Celestia smiled excitedly, “Well get ready as there is something that feels even better than my finger in your pussy. Are you willing to try it? This one is your choice, Twilight.”

At that point, I was willing to try just about anything. Everything we had done so far had felt amazing and I wanted more. Some primal desire I had never know I carried had been awakened. “I want it, princess.”

Celestia nodded sagely, “Very well. Vigil,” she turned to her royal guard who had been sitting on the couch and stroking himself to our lesbian session. He looked up at his name and stood to attention again. His proud member bounced around as he scrambled to his feet.

Celestia nodded to me. “Vigil, your last task in this lesson is this: Make love to my student. Show her the pleasures of intercourse and take her from being a girl and remake her into a woman. I trust this task to you in my stead, as I lack the proper, shall we say, equipment to properly perform myself.”

Vigil eagerly agreed to Celestia’s proposal, “I would be honoured to perform this task, your highness.” He turned to face me, getting down on his knees next to me. I reached out a hand and started gently stroking his penis; it seemed like the right thing to do and it was just hanging there.

“Twilight,” he said, pulling me up off my back, “Do you want this? As willing as I am to do this with you, I will only do it if you say yes. The princess was right; this has to be your choice.”

This was it. I knew what was about to come next. Some of the best teachers in all of Equestria had taught me the facts of life, and I knew that Constant Vigil was asking my permission to penetrate me. I could end this right now; I was sure that Vigil would respect my word. All I had to do was say,

“Yes,” I replied firmly. I gave his shaft and extra stroke with my hand and was pleased to see that he seemed to be ready to go again. I knew that some men could only last a short time or needed lengthy breaks to recover. Vigil seemed to have plenty of stamina.

In one motion, Vigil scooped me up in his powerful arms and carried me over to the couch. Celestia had moved over to one side and was openly playing with herself as we sat down on the soiled seats. The cushions were damp with the fruits of our arousal but I didn’t mind; I knew that at least some of it was mine.

Vigil sat down on the couch and picked me up before setting me down on his lap. He turned me to face him and I could feel his penis wedged in between us. It was warm and hard on my belly and I could feel his balls tickling against the underside of my legs.

“Are you ready?” he asked and I gave him a sharp nod to signal that I was.

Grabbing me by my hips, he lifted me until I was nearly squatting over him. From this position, I could feel the tip of his cock line up perfectly with my vaginal tunnel. The tip of his cock brushed against my clit and I felt a thrill run through me again. My body knew exactly what was going to come next and it responded by upping the amount of lube being secreted from within.

Very slowly, he pulled me down and I felt his penis split my lips apart and slowly begin to push its way inside me.

I bit my lip as Vigil’s cock pressed into me. I could feel my lips parting and opening as he sank within me body. It was like Celestia’s finger, but far thicker; he left me feeling full, like I had eaten a big meal. With a sudden ‘pop’, Vigil’s head fully entered me and my eyes bugged out as he slid in several inches of his thick meat. There was a sudden surge of pain as my body had to stretch out to accommodate the new invader.

As quickly as he had begun, Vigil suddenly came to a stop when he hit a fleshy barrier within my vagina. I could feel him prodding against it; it was a different kind of pressure. Tinges of pain throbbed each time he touched against it, and suddenly I was unsure if I wanted this to continue. I knew that this next part was going to hurt; it was a cosmic injustice that a woman’s first time had to be tainted like this, but that men didn’t have to suffer.

Vigil held himself perfectly still within me, allowing me to adjust to the first half of his length. He probed against the barrier a few times, but he didn’t press forward enough to break it. Instead he slid his hands all over my body, rubbing my breasts and encircling my hips. His hands felt great and they distracted me from the occasional thrum of pain from my lower body.

After a few moments, Vigil lifted me up and withdrew his penis until only the tip remained inside me. “Are you ready, Twilight?” he asked, “This is going to hurt the first time. Say the word and I will stop this right now.”

“No,” I mumbled. Even just having his crown inside me felt incredible. I knew that it would hurt, but I wanted to feel his entire length within me. My body was begging for the relief that only having his cock in me could provide.

“Then I shall leave it up to you,” he replied and secured his hands around my waist. “Go as fast or as slow as you need.”

I looked over to the princess. She had one hand cupping her breasts while the other had two fingers inserted deeply into her vagina and pumping furiously. She was moaning lightly as she did and didn’t appear to be aware of me looking; both her eyes were closed and her face was turned to catch the sunlight streaming in through the window. She was lost in her own little world of pleasure. This moment was going to just be between the two of us.

Slowly, I lowered myself back around Vigil, relishing the feeling of his penis moving back inside me. It stimulated my body and filled me up. I could feel my vagina stretching out to accommodate him and soon he was pressed up against my hymen again. I lightly pushed down again, testing the resistance of the barrier but not pushing past it. Under me, Vigil kept a hold of my waist, but his eyes had rolled back into his head. He was clearly enjoying this as much as I was.

Gritting my teeth, I pulled back, allowing the shaft to nearly slip out of me. That caught Vigil’s attention and he focused back on me. I looked him right in the eye. This was going to be my first time, and I wanted to remember it forever.

“Ready,” I said before slamming my hips down and sinking as quickly as I could down onto Vigil’s waiting shaft. In a moment he hit my hymen and tore right through it, shredding the flesh apart and piercing his way deeper into my body than anything had ever gone before.

I screamed from the pain; it was like someone had just knifed me in the gut. Every instinct in my body yelled at me to roll off of Vigil and have him slide out from me. Tears began to well in my eyes and looking down, I could see a few drops of blood seeping out along side my leaking juice. I tried to rise up, to expel the intruder in my flesh, but Vigil held me fast with his hands, holding me still and quivering on his prick. I tried to struggle against him, but he was too strong and I couldn’t move.

“Don’t move,” he commanded me, “It will only hurt for a second. If you try to move not, it will hurt more. You body just needs time to relax and acclimatise itself to me. If a minute or so it will not hurt anymore.”

His words calmed me and I tried to think of the lesson I had learned about this when I was still in school. Now that my hymen had been broken, it would never hurt like this again and my body would soon stretch out to accommodate Vigil’s member.

We both waited there, our genitals mashed together with him sheathed within me up to the hilt. With a tentative movement, Vigil learned forwards and pressed his mouth against mine. It was a slow and tender kiss and I returned it, leaning forwards as well until my breasts were pressed up against his chest. The feeling of his skin on my nipples was electric; nearly as good as when Celestia had been suckling on them. We remained there, lips locked and pressed up against each other for I don’t know how long. The passage of time meant nothing right then; all that mattered was me and Vigil and this moment.

Eventually it occurred to me that I no longer felt any pain. All I could feel from my genitals was a sense of fullness and some radiating heat. My body had adjusted to containing Vigil and was now ready to let him begin thrusting. Experimentally, I tried squeezing my vaginal muscles, contracting hard around his shaft. Vigil gasped and moaned as I began to rise up on him.

It felt odd, the sensation of him withdrawing from me. It felt as though some kind of pressure was being released from me as I rose up. Soon only the very tip of his penis was holding on within me and I could see his shaft making a connection between our bodies. His shaft was shiny with my juices and slick to my touch. With a single stroke, I sank back down, revelling in the feeling of being filled once again. This time there was no pain; only an overwhelming feeling of pleasure. As soon as I bottomed out, I began rising up again, letting my body’s instincts take over. Thousands of years of instinct drove me forward and I began to rut myself silly on Constant Vigil’s hard cock.

“Oh, Twilight,” Vigil breathed, “You’re so tight.” He had his eyes screwed shut as if he was trying to blot out all other sensations than those emanating from his penis.

“And you feel so good,” I replied. A moment later, I cringed at how corny I sounded. I was right though; he did feel good. There was something primal about having Vigil deep within me.

Soon I started to pick up a smooth pace; bouncing on his cock with ease. I was so slick from my previous two orgasms that Vigil moved with little resistance within me, despite my being so tight. With every downstroke, I could feel him pushing my vaginal walls apart and prodding me deeply. With every upthrust, I could clench down as hard as I could, pinning him so that he would have to strain to move. The heat from his loins was nearly burning, but I didn’t care; he just felt incredible.

We remained like that, me bouncing on his hard shaft for some time. He seemed content to sit on the couch while I did the work, and I didn’t mind that as long as I got to continue this incredible feeling.

Suddenly, both of Vigil’s hands shot up and he grabbed me and flipped us over. I wasn’t expecting it, but I ended up flat on my back, pressed in hard against the cushions of the couch. Vigil was now on his feet and leaning over me. Gathering me up in his arms, he thrust forward harder that I had ever thought he could do. Instantly I felt him penetrate deeper than I had ever felt him go, and he thumped hard against my cervix. My vagina gave a hard twitch at the feeling.

Now with all the leverage he needed, Vigil began working his hips hard, thrusting back and forth like a piston. He was being a little bit rough with me, but I didn’t mind. In this new position, his thrusts were now pushing up against new places within me; I was mewling like a little cat every time he pushed into me. Out of instinct, I wrapped me legs around him, trying to hold him close to me.

After one particularly savage thrust, he touched something deep in me, and that was it. My body burst into its third orgasm; this one far more powerful than the previous two. My legs locked hard together, squeezing Vigil into me and shoving his penis as deep as it could possibly go. My vaginal walls were rippling constantly; trying to milk his cock for all that they were worth, while my juices spilled out around Vigil’s shaft and soaked into the couch. Instantly, my hands went to my breasts and squeezed them hard, and I think that my hearing faded for a moment; drowned out by a ringing in my ears. For a moment, I’m pretty sure that I may have blacked out.

Slowly, as my senses came back, I realised that Vigil was building up steam with his thrusts. Each one was slightly faster and more powerful than the last. With a sudden cry, he gave one last thrust and held himself deeply within me. A second later, I felt his cock twitch hard. I couldn’t sense it, but I was sure that he was unloading a fresh wave of sperm deeply into my womb.

I counted five twitches before Vigil slumped onto the couch next between me and Celestia. His cock slipped out of me and instantly a thin trail of gooey white sperm leaked out, dribbling down to join the assortment of bodily fluids already staining the couch. Vigil looked exhausted; a sheen of sweat covered much of his body and he was panting heavily. There was no question that he was done for the day.

Celestia, noticing that Vigil was finished, leaned over and once again began to clean his cock of our juices. Despite her skill, he didn’t show any sign of returning to readiness; he was done.

Idly, I stroked myself while watching them. Any discomfort I had felt at seeing Celestia naked or watching her perform sexual acts on another had vanished some time during the day. Now it was just something that I realised that she had kept from me until she thought that I was ready. When she saw that my fingers were coated in Vigil’s sticky cum, she reached over and started licking them clean as well, before diving in and giving me a long lick from the base of my slit all the way up to my clit. It felt great, but I was just as exhausted as Vigil and I couldn’t get the energy to rise up to return the favour.

As Celestia lay sprawled across Vigil, licking my vagina clean of cum, I felt more tired than I had felt in a long time; like I had just spent several days up in a study frenzy and was just about ready to drop.

Trying in vain to stifle a yawn, I blinked a few times before my eyelids closed for good. My last sight was of Celestia looking right up at me, her tongue pushed halfway into my slit and a load of semen in her mouth.

The next thing I was aware of was a hand shaking me gently on my shoulder. I rolled over to one side and blinked several time, allowing my eyes to focus. I was lying in Celestia’s bed, snuggled up under the covers. Judging by the deepening orange of the light streaming in through the window, it was now late afternoon; I must have slept for several hours. Shifting over in the bed, I noticed a sharp ache from my stomach and legs. A moment later, I realised that it wasn’t an ache in my stomach; my body was sore after all the new experiences that I had just had. I had been prodded in areas that I didn’t know existed and now they were protesting the abuse.

The hand rocked me again, and I looked up to see Princess Celestia standing over me. At some point she had changed into a long flowing robe that covered her from neck to just above her feet. Looking down I could see that she was barefoot and her creamy white skin nearly matched the colour of her robe.

Seeing that I was awake, she stopped shaking me and stepped back to give me the space to get up. “Up you get, Twilight,” she said gently, sounding just like she did when she caught me asleep when I had stayed up all night to study. “You need to get ready to go; the last train going through Ponyville will be leaving in a little over an hour.”

I pulled the covers of her bed off of me and slid out onto the ground. Someone; likely Celestia herself had dressed me in a robe similar to the one that she was wearing. It felt light and very clean. My legs and stomach protested the shifting and I groaned as I got up, putting a hand to my gut as I stood. Celestia smiled knowingly at me and extended a hand to help me up.

“How do you feel?” she asked me.

“Sore,” I muttered. “But, I feel good. Relaxed and strangely content,” I added in after.

“Don’t worry, Twilight. It may take a day or two, but you will feel better quickly, and you won’t have to worry about it again. Your body will handle the stresses of sex better the next time,” she said, giving me a crooked smile.

“What about Vigil? What’s happened to him?” I asked. I couldn’t see him in the room.

“Don’t worry about Constant Vigil. He had returned to his home for some much needed rest. I know about what happened with him and his wife; it was the reason that I asked he be posted as my door guard today. He deserved this treat and I knew that he would be kind to you. And you needn’t worry about getting pregnant from him; after the birth of his last child many years ago, he chose to be snipped.”

That hadn’t even reached my mind yet, but I was glad that Celestia had told me. I wasn’t ready for a baby just yet; not now that I had just discovered sex.

I walked over to the pile of my clothes that we had thrown to the floor. They had clearly been cleaned and arranged while I was asleep; they looked sparkling clean and not a trace of any smell could be found. I gathered them up and prepared to get changed. Given what had happened earlier, I figured that there was no need to go into another room and quickly stripped out of the robe. Celestia walked over and rubbed my shoulders as I slipped on my panties and hitched up my skirt again.

“Twilight, now that you have learned about sex, I would like you to continue your research when you return to Ponyville,” she said before picking up my bra. She fiddled with it for a moment before slipping it on around my chest.

“But I don’t know anyone I could ask to ‘do it’ with me,” I protested. Sure there were plenty of attractive guys in Ponyville, but none that I was close enough with to trust with something like this.

“Don’t worry about that, Twilight. Your friends will be able to help you. In fact, I know that your dressmaker friend, Rarity is planning to try her hand at playing matchmaker with you.”

I gasped at that. I had no idea that Rarity was planning anything. She had always seemed so busy with her own love life; planning just how to catch the eye of some royal. “How do you know that, Princess?”

“Because I asked her,” Celestia said simply. “When she came to stay at the castle just before your birthday a couple of years back we talked at great length. She expressed her concerns over you, that you never seemed to notice when a suitor approached you or ever went out looking for companionship. That was really what made me realise how badly I had failed you. Speak with her when you return; I didn’t tell her exactly what I had planned for today, but she knows that today was going to be special for you.”

With that, Celestia finished hitching up my bra and passed me my shirt. I put it on and began buttoning it up, realising that I still had to get to the train station before the last engine left for the night. As I turned to leave Celestia’s chambers, she put a hand out to stop me one more time.

“Oh, and Twilight; I expect you back here at the same time next month for a follow up exam. You can show me what you have learned, and if you pass,” Celestia paused for dramatic effect, a playful expression passing through her eyes, “I may even let you taste the royal pussy.”

That was all the motivation I needed, thoughts of Celestia licking mine still fresh in my mind. I would go back to Ponyville and ask for my friends help and next month I would return to show Celestia all that I had learned.

With one last nod to Celestia, I slipped on my shoes and headed for the door.

“Don’t worry, Princess. I won’t let you down. I’ve never failed an assignment yet!” I said heading out the door, visions of the coming month floating through my head. Applejack’s brother had always been nice to me. Maybe Rarity could help me arrange something.

I emerged into the late afternoon sun of Canterlot, no longer a timid girl responding to a summons from her teacher.

Now, I was a woman.

Author's Note

And here is chapter 2.

I hope you enjoyed this story about Twilestia that doesn't actually feature much Twilestia

There will be at least one sequel to this story at some point.