Twilight's Training

Twilight squirmed in her seat, struggling to focus on the pages in front of her. Work had come slowly this past month, with frequent “interruptions” to her private chambers becoming the norm. This hadn’t impacted her workflow significantly, as the Princess of Friendship she didn’t have much in the way of royal duties to perform or royal paperwork to oversee. Even when she did, Spike handled most of it, but that just made him all the more suspicious as to why she kept wandering off.

Her friends, too, were growing suspicious. More than once they’d come knocking on her door, politely but insistently, wondering if she was sick, or sad, or otherwise having a problem that they could fix. Rainbow Dash was the only one bold enough to accuse her of what she was actually doing, but the others had to suspect by now. Hell, Pinkie had been dropping some not-so-subtle hints that she would be happy to join in, if Twilight wanted to do more than play by herself.

But none of that would satisfy anymore, leastwise it certainly didn’t seem to. Her date with Flash Sentry had been intense and loving – he’d gotten her to cum twice – but it just wasn’t the same as Celestia. He cared about her, sure, but he didn’t have the skill, technique or sheer size of the Princess. Plus, the fact that she sort of felt like she was cheating on him, even though they both insisted that they were not dating and were just friends (with benefits, as Pinkie would put it) made her dally with Celestia all the more distracting. She wanted to tell him, wanted to admit what she and Celestia had been up to, but she just couldn’t. One, she’d promised, and two, how could he expect to compete with somepony who’d had 1000 years of practice?

Even Mr. Shivers seemed to be less than satisfactory now. Sure, the big black rubber cock provided the filling and depth that she wanted, but warm rubber was hardly a replacement for a loving partner. Flash Sentry was certainly a loving partner, but he couldn’t get the depth and technique that she now knew she needed. Maybe with time she could teach him, but what about now? Every time she failed to scratch her itch, it seemed to just get worse. The old standby of raunchy stories combined with masturbation was barely giving her any relief. She needed to talk to the Princess, and soon, before her lustful desires got any worse.

She couldn’t right now, though, not when Celestia was busy far away with business in the Crystal Empire, when her own studies were languishing in repetition and half-finished essays. Still, she needed a little relief, and if she was going to get through this book without distractions, she’d need to blow off some steam. Then she could finish her book, send Celestia the essay and add a p.m. that she wanted to discuss the implications “in private.” Surely, the Princess was certain to get the hint? Or maybe Twilight needed to be more direct?

Twilight laid down on her bed and slipped her hoof between her legs. No time for Mr. Shivers right now, she’d just need to get rubbing and use her imagination. She closed her eyes and began to move, caressing her clit and slit delicately, moving around gently and touching all her favorite spots. She tried to think back to the way that Celestia had touched her, the way that Celestia had moved inside of her, the way she’d felt that night one month ago.

The thought of being with Celestia set her lust to a full boil, and in moments she was working herself with two hooves, her nipples and sex being caressed wildly and fervently. She whined, arching her back as she thought back to the way that the Princess had worked her sex, the way that massive cock had tasted in her mouth or felt deep inside of her. There had just been so much of it – the immense size, the intense thrusting, the cum dribbling down her thighs. How could she go back to normal masturbation and penetration at this point?

Twilight groaned and continued to work herself, both frustrated and aroused by the thoughts and sensations. Her masturbation, rather than being the welcome relief it had always been before, was now a tantalizing near-sex, something that seemed to just leave her wanting more, rather than feeling fully satisfied. It was half a meal, the first hour of a movie, the first ten chapters in her favorite book. She wanted more, dammit! And just as soon as she was finished here, she was going to write to the Princess and demand it.

“Oh my. I’m not coming too late am I?”

Twilight yelped and crawled up her bed in a panic, banging her head hard against the headboard. She tried to stumble to her feet, but as the front two of them were dripping with juice, she couldn’t find sure footing once she left the bed, and she collapsed in a heap at Celestia’s feet. She whined, wanting to grab the sheets and bury herself in them, or else crawl under the bed and hide. How did Celestia manage to interrupt her at private moments like this? Was she doing this on purpose.

“Really, dear, a Princess like you should know to lock her doors.” Celestia kissed Twilight on the tip of her horn, then grabbed her and pulled her to her feet. “I’m certain your friends wouldn’t think any less of you if they walked in on you, but I’m just as certain that you’re not of a mind to show them. It would be un-Princess-like, at the very least.”

“I swear I locked the door!” Twilight panted, now realizing that, no she hadn’t, since she’d originally intended just to finish the last few arguments on her essay. She hadn’t been thinking, and now the Princess had interrupted her mid-clop for a second time. “I mean, I thought I did.”

“Twilight, you really need to not be embarrassed by these things, not after what we’ve done together.” Celestia brought Twilight in for a quick hug, then kissed her on the cheek. “For goodness sake, I’ve been inside of you at this point. And you look so cute when you masturbate. You scrunch your face up and it turns bright red and you let out these adorable moans…”

Twilight blushed a bit, burying her face in Celestia’s side, but the Princess’s frankness did indeed help her calm down a bit. Yes, she had nothing to fear, it wasn’t like she was up to anything Celestia hadn’t already seen. She wasn’t so much revealing a side of her the Princess was unfamiliar with as physically expressing how much she missed what they had gone through. They were both adults, and it was perfectly okay for them to see one another in that way. Though still, she felt that she wouldn’t manage to be this calm, cool and collected if she walked in on Celestia manipulating her own massive shaft.

“Luna told me that your dreams were somewhat...Frustrated. That it seems the fire I lit inside of you has grown to a raging inferno, and that I need to pour some water on it immediately.” Celestia grinned, nudging herself against Twilight’s flank playfully. “Or in my case, cum. So I finished up what I couldn’t delegate and came as fast as I could. Though I imagine my second cumming will take a bit longer. Care to join me in our special place, Twilight?”

Before she could reply, Twilight found herself once again in Celestia’s secret love chamber, surrounded by strange and exotic furniture lit by low-burning torches. She was in a different part of the room this time, one without a bed. Instead there were other strange structures, all coated with the same stain-proof material, but arranged in bizarre positions and coated with straps and buckles. Leather was everywhere, as were cuffs and collars lined with faux fur. She was reminded of some of the sex furniture she’d read about in books, but she’d never seen such things in the real world. The hairs on the back of her neck stood on end, and as she thought about how she’d be positioned in each of them. The thought of being tied up and helpless while Celestia did whatever she wanted – it started pushing buttons Twilight didn’t even know she had.

Celestia began to run her hoof up and down Twilight’s flank. “I do apologize for allowing it to be so long since our first session. When you get to be my age, time just doesn’t move at the same speed as when you are young. But don’t worry, during the past month I’ve been thinking back to what you were reading when I first found you, and I thought you might be interested in this sort of thing.” Celestia lifted up a thick leather collar, holding it out in front of Twilight. “So what do you think?”

Twilight took deep breaths, staring at the collar. It was fur lined, the buckle secured with a lock. A large golden tag read “TIA’S BITCH” in clear print. It glinted in the light, catching Twilight’s eye. Something deep inside her wanted her to put that on, to give herself over to the pony she’d looked up to for so long. She bit her lip and looked deep into Celestia’s eyes. “...I’d like to try…”

“One thing before we start.” Celestia yanked the collar away, dangling it just out of reach of Twilight’s hooves. “We’re going to need a safeword for you to shout if you get into trouble. How about ‘chimichanga’? No, that’s too long. How about just ‘banana’? If you start to hurt, or you’re getting tired, or if you just need me to stop, start shouting ‘banana’ as loud as you can. Get it?”

“Banana.” Twilight’s eyes were still locked on the collar. “Got it.”

Celestia grabbed a riding crop off the wall and brought it down hard across Twilight’s ass, making her yelp. “That’s yes MA’AM to you, bitch.” She brought the collar around Twilight’s neck and locked it firmly into place. “You only say two things to me, bitch. Yes ma’am and no ma’am. And you’d better answer with the right one, or else we’ll turn that pink rump of yours bright red. Do you understand, bitch?”

“Yes ma’am” Twilight panted, rubbing the collar with her hoof. She had never thought that the feel of fur and leather against her neck would be so exciting. It was snug but not tight, the tag jingling a little as she moved. The smack from the riding crop had hurt much less than she thought, but still, her rump was stinging. It was the good kind of hurt though, the kind that got her juices flowing.

“That’s better.” Celestia pulled several leather items from a nearby table. They glowed with mystical purple jewels, each emitting a mild passive aura. She strapped one across each of Twilight’s wings, locking them into place with golden locks, then slipped the last across her horn. “Bitches don’t need to fly, or use magic, do they, bitch? They just need to do what Princess Celestia tells them.”

“Yes ma’am” Twilight could feel the magic leaching from her horn and wings. None of the appendages withered, but the bindings were tight, draining her of her power. With neither wings to fly nor a horn to cast magic, she felt trapped and vulnerable. She was within Celestia’s power. And somehow, this is how she wanted it. She wanted to open herself up to Celestia, to let this powerful god-horse do whatever she wanted. She bit her lip, looking up at Celestia, her backside quivering with anticipation.

“Head down, bitch, you don’t deserve to look at me.” Celestia brought down the riding crop again, then pushed Twilight’s head to the floor. “Clean my hooves, slut. Kiss them with your lips and lick them clean with your tongue. I want to be able to see my reflection in them before you sit back up again.

Twilight bent down slowly, looking at Celestia’s hooves. They were shod in long black leather boots that ended in an iron horseshoe, as opposed to the gold and jewel-encrusted hoofwear she normally favored. Twilight bent down to kiss them, not sure what to expect in the dim light. As she put her lips to them, she found that they were impeccably polished, and still reeking of leather polish. They were still wet, whatever castle servant had applied the polish had either neglected or been ordered not to finish the brushing. She kissed them a few more times, the bitter taste of polish getting deep in her mouth. But somehow the unpleasant taste just drove her to try more, and soon she was licking the hoof all over, the taste of polish, leather and iron thick across her tongue.

“You didn’t say ‘thank you’, stupid.” Celestia brought the riding crop down hard on Twilight’s ass, leaving red welts as it smacked deep through the purple pony’s fur. “Isn’t it a great honor to kiss your Princess’s feet, to clean them with that worthless tongue of yours?”

Twilight winced harder at being called ‘stupid’ than being smacked on the ass. Somehow the words hurt more than the crop, even though she knew that Celestia couldn’t mean such a thing. It was part of the play, just like having to call her ma’am or keep her head down. But it still stung more than she’d like. She moved off the boot, the shoe polish on her tongue making it hard for her to speak. “Thank you, ma’am.”

Celestia brought the riding crop down again, this time smacking it across Twilight’s shoulder. “I told you, you only say yes ma’am and no ma’am. Or is that too complicated for you to understand?”

“Yes ma’am.” Twilight whined in frustration. It seemed that no matter what she said or did, Celestia was going to bring down the whip. Maybe that was the point? It probably was. She certainly wasn’t hitting Twilight very hard, and Twilight’s sex was still wet and winking. There was so much new stuff all at once, it was hard to figure out what was going on, much less whether or not she liked it.

“There we go. See? You can learn, just like a good little pony. But right now, you’re my bitch, and you’ll act like it.” Celestia took a few steps back, getting on the other side of what looked like a saw-horse, only it was coated in padding and leather straps. “Now be a good little bitch and climb here up on my table.”

Twilight climbed up on it, her tongue hanging out and coated with shoe polish. She tried licking at it, but the stuff was pretty persistent, and she had trouble getting it off, even when she scraped at it with her teeth. Before she realized it, Celestia had locked her in tight, her hooves being tied to the legs of the “table” and her body strapped firmly to it. She could barely move against it, her rear end hanging off the far edge. If she had been exposed and helpless before, there were no words for how she was now!

Celestia moved to Twilight’s backside, giving it another firm blow with the riding crop. “Mmm, this is definitely your good side, bitch.” She dragged the tip of the crop up Twilight’s slit, making the captive pony twitch slightly. “You’re already wet and winking. Does the thought of taking your mistress’s cock deep inside of you arouse you that much? Too bad, my cock isn’t quite ready for your cunt just yet.” She pulled out another strap, attaching it to the base of Twilight’s tail. She forced the appendage back, then locked the strap into one crossing Twilight’s midsection, leaving the poor pony’s tailhole and rear end all the more exposed. “There, now you’re really pretty!”

Twilight squirmed from her captivity, afraid to talk, but unable to move. Instinctively she tried to move her wings or course magic through her horn, but this only made the purple jewels that bound them glow more intensely. She whined, unsure what Celestia would do next, but knowing she wanted the Princess to do it soon.

“If a bitch like you thinks that she deserves to have a Princess’s cock in her worthless cunt, she needs to earn it first. And since you can’t seem to work that tongue of yours on my boots, how about you work it on my holes instead?” She shoved her mare-sex against Twilight’s face, continuing to push until her balls were on Twilight’s chin.

Twilight had eaten pussy before, mostly during her “experimental” phase in college. But she’d never done so at such an angle before, nor had she done so with a she-stallion. Should she kiss and lick the balls too? Did Celestia mean for Twilight to work the asshole? She wasn’t sure, but she dug in gently, doing her best to work Celestia’s slit and clit gently but firmly. She worried a bit about the shoe polish at first, but as Celestia’s shoving got all the more intense, she realized there were more important things to worry about. She moved up and down, her lips and tongue getting a bit tired and raw, but still able to move. Celestia’s sex was wet and winking, dousing Twilight with juice. She must be doing something right, to get it like this, so she kept going, trying her best to remember what Celestia had done to her own sex during their last encounter.

“Mmmm, that’s better, bitch. Keep it going. And don’t forget my balls or my other hole. Let’s see you try to impress me!” She brought down the riding crop again and pushed back, practically sitting on Twilight’s face at this point.

For her part, Twilight struggled to do more, taking long licks up and down Celestia’s backside, licking and kissing and probing at everything presented to her. She would have thought that she’d find Celestia’s backside less appealing, especially her second hole, but as she licked and probed she found herself enjoying the act, albeit more mentally than physically. The Princess had cleaned herself well, but the act alone was repugnant, even though the thought of doing it filled Twilight with disgusted glee. She felt at home with her tongue up Celestia’s ass, closing her eyes and digging in deep. She could hardly believe she was doing this, but the more she did it, the more she wanted. The wrongness of it, the bizarreness of it, and the way that Celestia moaned and pressed down on her muzzle as she did it all the more – it was driving her wild!

“Enough!” Celestia coughed and pulled off suddenly, her sex winking and dripping in Twilight’s face, her balls tightening and jiggling. “You almost had me cumming there, bitch. And there’s a much better place to put the royal seed!” She moved behind Twilight, tapping gently at her pussy, then pulling back. “No, there’s a better hole for this…” She began to lick and kiss at Twilight’s tailhole, gently nibbling it and teasing it with her hoof. She carefully worked it open, giving Twilight time to relax, even as she kept herself going, working her own shaft and keeping it nice and hard. She pulled a dildo off a nearby shelf and then began to work Twilight with it. “How’s that feel, bitch? Are you ready for me now?”

“Yes ma’am…” Twilight groaned, panting as she felt the rubber shaft slide inside her. She’d always shied away from playing with her tailhole, though many of the mares in her books certainly seemed to enjoy ass-play. It was where she pooped, after all, and it was kind of gross, and besides she didn’t want to have to clean up the resulting mess or risk having to explain herself when she was doing so. But it certainly didn’t feel bad, in fact, the way Celestia was doing it felt amazing!

“There, maybe now your hole is loose enough to handle the royal cock!” Celestia lined herself up carefully and began to push in, grunting as her unflared tip probed and pushed the hole. The resistance was strong, but she kept it up, gently applying more and more pressure as she teased Twilight’s hole to give way.

But something wasn’t right. The pleasant fullness and satisfaction that Twilight had been feeling was giving way to pain, and not the slight, pleasure-enhancing pain that the riding crop had been. This was an emergency pain, the sort that told Twilight something was wrong. She began to panic, writhing and kicking at her restraints. But unable to move, she couldn’t get away, couldn’t extract herself from under Celestia. She whined. “No, wait! Stop!” She struggled, then thought back to what the Princess had told her earlier. “Banana! Please, Celestia, I said banana! There’s something wrong!”

Celestia immediately backed off, her erect shaft flopping between her legs as she magically undid Twilight’s restraints. Hurriedly, she moved in front of Twilight, gently placing a hoof under the purple pony’s chin. “What’s wrong, Twilight? Are you okay?”

Twilight whimpered. “I think I broke something back there.” Gently, she climbed down off the sex table, trying to turn around at some angle where she could see her backside. She pawed at it a little with her hoof, trying to get a good look. “It really hurts!”

Celestia moved in and took a look, clucking her tongue. There wasn’t any severe damage, but “I guess I got too enthusiastic. You’ll have to keep your anal virginity for at least another week.” She moved behind Twilight, grinning. “Here, let Mistress kiss it better.” She bent down and kissed Twilight’s tailhole, noting that it wasn’t bleeding too badly, and other than the initial shock and some soreness for the next day or so, she was unharmed. “Lemme get some salve that will help it heal.”

“I’m sorry I had to stop.” Twilight sniffed. She could still feel the wetness between her legs, and even with the pain from her tailhole distracting her, she was still horny. She had been so close, and she needed to go off. If she didn’t, she would no doubt go mad with arousal well in short order. “I just, I didn’t…”

“You did what you were supposed to, Twilight, and if you hadn’t stopped when you did, you might have gotten hurt.” Celestia rubbed a hoof across Twilight’s forehead and then kissed the tip of her horn. “Don’t worry about it. You’re learning, finding out what you like, what you can handle.”

“But I...I still need.” She bit her lip, putting her hoof to the large tag still dangling from her neck. She looked at Celestia, then climbed back up on to the table, putting her hoofs against the now open and loose restraints. “Please mistress, I’m so close!”

Celestia grinned, returning the locks quickly, even strapping the magical bands back around Twilight’s horn and wings. “Such an eager student! Well far be it for your mistress to stop you from learning!” She brought down the riding crop on Twilight’s backside, but lightly this time, more playful than intending to cause harm. She moved behind Twilight and lined herself up with Twilight’s puffed sex, finding it wet and inviting. Still, she moved in slowly, giving Twilight lots of time to adjust. She leaned over Twilight, putting her pressure on Twilight’s back and wings as she slid in slowly. “How do you like that, bitch? You just love having a big fat Princess cock inside your cunt, huh?”

“Yes ma’am!” Twilight whined. The interruption seemed to have only driven her harder, and now that she was suddenly back on that horse – literally –- she wanted to go off even worse than before. Though she was restrained, she tried to push back against Celestia, to get the Princess’s enormous shaft all the deeper inside of her. Her whole body was boiling at a fever pitch, and the release was tantalizingly close. “Please Princess, fuck me harder!”

Celestia brought down the riding crop across Twilight’s cheek, leaving a red mark below the purple pony’s eye. “What did I tell you about talking, bitch?” But Celestia nonetheless kicked up her pace, adjusting her front legs on the sides of the table to get a better angle. She pushed in relentlessly now, almost her entire length pistoning in and out of Twilight’s puffy, dripping sex. The brief delay had driven her orgasm wild as well, and her shaft twitched and throbbed with approaching orgasm. Her tip began to flare, and she drove it home as she let herself unload deep into Twilight.

Twilight whimpered with delight and ecstasy as she felt the Princess cum inside of her. Somehow, this felt even better than the first, and from her restrained and helpless position, she felt the orgasm hit her and begin to rack around inside, tickling her from her hooves to the tip of her horn. Magic fizzled against the restraints even as she tried to kick and buck from where she was held, but the leather dug in firmly, holding Twilight in place. Her own orgasm was wild, her juices mixing with Celestia’s and running messily down her thighs.

Celestia held herself in deep for a few moments, grinning and nipping at Twilight’s ears. She was panting hard, her shaft still throbbing and pumping out a few last parting shots. Rather than pull out, she remained inside, the hot, wet shaft slowly cooling and shrinking inside of Twilight. Carefully, she used her magic to remove or loosen Twilight’s restraints, but she still kept the purple pony pinned beneath her. “Well Twilight, did you enjoy yourself? The literal pain in the ass besides, I mean.”

It took Twilight several minutes to compose herself enough to speak. Before she could, she adjusted herself a little, kissing Celestia here and there and smiling. “It was wonderful, Princess.” She tapped the tag on her collar, blushing. “I think I could really get into this. I...I like being tied up, I guess. And the rough play, it’s...It’ll take some getting use to, but I think I’m really into it.”

“I gathered as much from the way you were screaming and moaning.” Celestia playfully batted Twilight’s ears. “You were like a virgin on prom night with all the noise. Maybe it’s high time I introduce you to ball gags.” Celestia pulled off of Twilight slowly, retrieving a nearby towel and beginning to wipe herself clean. “Is there anything I need to change? Other than the butt sex, I mean. We’ll have to get you on an anal training regimen before I go back in there. I wouldn’t wanna hurt your cutie patootie!”

Twilight bit her lip, afraid to say. She didn’t want to tell Celestia her business, but she had just asked, and the issue had been sitting in the back of her mind the entire time they had been playing. “Can you not call me stupid next time? I’m okay with the dirty talk – it’s a lot of fun, most of the time. I mean, calling my sex a ‘cunt’ is a little rough, but calling me dumb, it kinda…”

Celestia put a hoof over Twilight’s face. “Twilight, I’m fine with that. I only say those things as part of the play, and I’d never want them to hurt your feelings. It’s just a little bit of verbal roughness, to go along with the spanking.” She gave Twilight a hug. “But I know how words can hurt, so of course I’ll be happy to change what I say.” She slipped around back and began wiping Twilight’s backside, cleaning her up as well before planting a kiss on across one of the welt marks. “And keep the collar. I have a feeling you’ll need it again next weekend…”