> Principal Celestia's Guide to Anal Sex
>  by Omega Dracomancer
> --------------------------------------------------------------------------

> Chapter 1
> --------------------------------------------------------------------------

"Hello! My name is Celestia and today I would like to tell you about anal sex. No..."

"Hello! I am Principal Celestia and today I would like to teach you about anal sex. No, that's not right either. Maybe if I..."

"Hello! I am Principal Celestia and today I would like to teach you how to have anal sex the right way. Better. Maybe..."

"Hello! I am Principal Celestia and today I would like to teach you how anal sex can be fun and enjoyable for both partners. Hmm..."

She sighed. After four takes of just the introduction line, Celestia quickly realized just how daunting this video could really be. Still, she pressed onwards. After all, this wasn't for her. This was for her wonderful, often misinformed students. Thankfully, video editing was far easier than it had been in the past.

"I know many of you..." She cleared her throat. "I know that many of you have been engaging in sexual activity in the building. Some of you have chosen to go the extra mile and engage in the exciting new world of anal play. I'm here to teach you some helpful tips when it comes to anal penetration." She grumbled, noticing herself stutter during the last sentence. "So close!"

"I thought it went well."

"Thank you, Luna."

"I also think this is quite foolish."

"You've mentioned, Luna. Once more, though. That was a longer section. Maybe I should do it in two takes."

"Perhaps you should prepare a script, like I've said."

"I don't know if it would feel as natural."

"Very well. The camera is still rolling, sister."

"Oh! Yes, I'm sorry. Where was I... Hmm... Right. I've got it now." She took in a deep breath. "I know that many of you have been engaging in sexual activity while in the building or at home. Some of you have chosen to go the extra mile and are exploring the exciting new world of anal stimulation. I'm here to teach you some helpful tips when it comes to anal penetration. How was that?"

"Perfect, like you."

"Oh shush."

Luna merely smirked.

"Alright, next line. Above all else, anal sex is not something to be rushed. Many of you are still inexperienced in this regard. If done improperly, anal sex between inexperienced partners can lead to a very unpleasant sensation for both parties, but especially for the reciever. Thankfully, if done right, there are ways to mitigate any unpleasantness."

"That went a bit better."

"Thank you, Luna. I'm still a little nervous about this."

"I can tell. You're not often one to be nervous, sister."

"That's kind of you to say. I think I just need to keep going and see how it turns out."

Luna nodded. 

"Now, an important step to enjoyable penetration is to practice. I will be going through a number of methods to do so in a moment. Before I start, keep in mind that this can be a long, slow process. You can't expect it to be something you can do in simply one night. It is not always an easy task to prepare yourself for anal. I will now demonstrate a few of these methods. Please excuse me for one moment."

Celestia stood and reached to her pants. She unbuttoned and unzipped them, then pushed them down her long legs. She did the same to her panties, stepping out of her clothing. She picked up her pants and straightened them, then set them aside. She then stepped forward, out of view of the camera.

"Time for the fun already, sister?" Luna asked.

"Oh, come on, it's not like that."

"Isn't it, though?"

Celestia gave her a sly smile. "Well, I might be looking forward to this."

"Color me surprised." Luna was somewhat amused by her sister's antics.

"It's hard to stay calm knowing what I'm going to do. I'm starting to get wet, too. This isn't supposed to be sexy, it's supposed to be educational."

"It's better if the teacher is interested in her subject, don't you think?"

"Yes, very true!"

"Besides... I think if it's you, it's hard not to be sexy."

Celestia rolled her eyes.

"Are you leaving your top on, sister?" Luna asked.

"Maybe. Do you think I should?"

"You'll be more comfortable naked."

"Good idea." She reached down and pulled her shirt off, placing it out of the way. She turned around and said, "Could you?"

"Of course." She took care of her sister's bra, unhooking it and placing it onto her discarded shirt. She reached around and grabbed a handful of her round breasts with each hand.

Celestia took in a gasp. "Slow down, sister. You'll get to play with them all you want later."

She chuckled, letting go. "Alright. Later."

"Where did you put my toys?" Celestia asked, turning to her.

"If you climax before the demonstration is over, we may have to record another take."

"I'll be fine, sister."

"Are you sure? You know how sensitive your ass is."

She looked away. "I'll endure."

She chuckled again. "If you say so, sister. I picked out the ones you wanted and put them into your nightstand."

"Thank you, Luna." she said with a smile, pecking her sister's lips.

Celestia opened the drawer. Inside were three sex toys and a bottle of lubrication. She pulled them out one by one, examining them. A short, thin plug, a smooth plastic viberator, and a rubber dildo of medium size with a suction cup for mounting. She placed these onto the bed and sat down.

"Do you think I should do it like this or from behind while I'm standing?" she asked.

"From behind. Your butt will be at a better angle."

"Right." She changed position and looked back at the camera. "Alright, I'm starting. Am I in view?"

"Everything seems fine here."

She took a breath, then smiled for the camera. "Most people find that their fingers will provide the ideal starting point for anal play." She reached back and began teasing her backdoor. "The easiest way to prepare yourself is to begin with light touching. While you're masturbating, try reaching a bit further and explore a bit."

Even though it was supposed to be a demonstration, she found herself giving in almost immediately to the pleasure. She let out a soft moan as she rubbed her backdoor. It took a few moments to realize she was going too far. Putting herself on display turned her on. Still, she was determined to continue.

"It may take a while, but once you feel you are comfortable, try inserting a finger. For this part, it's important to go slow. You don't need to force it inside. Calm yourself. Relax. Take deep breaths. Then..." She let out another soft moan as her finger slid inside without any effort. Her back arched downwards by instinct. Her finger slid deep inside, her hole twitching around it. She blinked, once more realizing that she had gone too far. "D-Don't expect to push it all in at once, but once you do, play around a bit. Move your finger in and out, keeping a slow, steady rhythm, like so..."

Her legs tensed as she began fingering herself. It didn't need to be a long demonstration, but it helped to make her point. Though difficult to hide her enjoyment, she managed to keep her moans to herself.

"It may take a while to get used to this new feeling. That's completely normal. In fact, it took me a number of weeks before I was comfortable with anal masturbation. Mmm... Don't be disheartened if it isn't entirely pleasurable the first time. Just keep it up and eventually your backdoor will want just as much love as the front. I know mine does." She sighed. "Cut that last part out."

"I will, sister. I will."

"Thank you. After you've spent a while toying around with your finger, naturally the next step up is to use more fingers. For this, I find it's easier to reach between your legs than to reach around your hips."

She pulled her finger from her bottom and moved her hand between her legs, reaching up so she could continue masturbating for the camera. Just like before, it took no effort to push her fingers inside. Her experience was beginning to show itself. She let out another moan as they slid deep inside and her wrist brushed her wet slit.

"I find the middle and ring finger to be the best for this exercise. After the first finger, the feeling will start getting more intense. It will only get stronger from here."

She moaned as she began moving her fingers, but after this first noise, she was able to quiet herself. She knew she wouldn't be able to hide her voice for much longer.

After a while, she finally stopped, pulling her fingers from her hole. She took in a deep breath, then stood up straight, turning around. She smiled at the camera. "After two fingers, there are many different paths you can take. Using more fingers is always an option, but you could also move on to toys. I have a few here I will be demonstrating later. After you find yourself enjoying anal play, the possibilities are endless. Personally, I find having my partner continue with their fingers to be the most fun after doing it yourself." She raised her hand and beckoned her with a finger. "Luna, if you will..."

"Oh, you want me to join you this time? What happened to enduring?"

"It won't be like last time, Luna."

"Not if I have anything to say about it." said Luna, stepping forward.

A look of concern covered Celestia's face. "Um... P-Perhaps you could be gentle with me."

"No backpedaling. Turn around for the camera, sister."

Luna noticed a smile on Celestia's reddening face as she turned, placing her hands onto the bed. "R-Remember, you're the one doing the editing for this, Luna."

"I'm aware." Luna replied, placing her hand onto her sister's plump rear. Celestia moaned softly as she squeezed, burying her fingers into her skin.

Celestia's backside was in full view of the camera. The two sisters gazed at each other as Luna grabbed her bottom, pulling her hips and spreading her cheeks.

"Well, sister?" said Luna.

"Right. P-Participating in anal play with your partner is notably more difficult than doing it on your own. Though everyone will experience it differently, ultimately, the methods to prepare will be the same. Once again, we will continue using our fingers. S-Sister?"

With Celestia in position, Luna glanced back at the camera, lifting her hand and inserting a finger into her mouth, coating it in her saliva. She lowered it to her sister's sensitive backdoor. Celestia moaned softly as she began massaging her ring. It wasn't long before her finger dipped inside her hole. Celestia knew it immediately to be her sister's middle finger. It pushed in deep, causing her to moan once more.

"Ohh... I love when you finger my tight ass." Celestia moaned, gazing upwards at her.

"I think I might have to cut that out."

Celestia chuckled. "Yes, I think that's a good idea. I'll try to keep it down."

"Stay still, sister. It's hard to keep a rhythm if you keep shifting around like that."

"Sorry. I'll try."

Luna did as Celestia did to herself, slowly sliding her finger into and out of her hole. Unfortunately for Celestia, it felt worlds better than when she did it herself. It was a struggle to hide the pleasure from the camera. Her hands gripped the blanket below her.

"C-Communication is key between partners. Be sure to let your partner know if they are being too rough. Or perhaps not rough enough." She chuckled. "Just like when doing it yourself, you may have them add another finger."

Following her words, Luna added a second finger to his movements. Celestia moaned as the feeling became more intense. The movements were still slow, but it gave her a consistent pleasure. She always loved when Luna played with her ass. She almost didn't want her to stop.

Celestia allowed her to continue for longer than she probably should have. As the pleasure began to build, she caught herself. "Th-That's enough for the finger demonstration. I think it's time to move on to the toys."

Realizing that she had pushed her sister rather far, Luna pulled her fingers away, leaving Celestia almost desperate for a release. 

Celestia stood up, turning to her sister, meeting her eyes. "Thank you, Luna."

She smiled. "Of course."

With this, she returned to his position behind the camera. 

Celestia stood up straight for the camera. "Are you ready?"

Luna checked between the picture on the camera and her sister's body. There was no issue. Celestia's skin was simply glistening with sweat, caused by her poor endurance. "Go ahead."

Celestia took in a breath to calm her racing heart. Letting her sister play with her little hole like that was almost too much. "After you have experienced anal play with fingers, the next possible step could be using sex toys. These include, but are not limited to, plugs, dildoes, and viberators. I have three toys here that I will be demonstrating. Additionally, I will begin introducing lubrication into these exercises. Lubrication for anything larger or more exotic than just a few fingers can ensure safe and enjoyable anal play. Allow me to show you a method of applying lubrication. Fear not, it's very easy."

Celestia retrieved the bottle of lubrication from the bed. Facing the camera, she opened the bottle and poured some onto her two fingers. She set the bottle aside and retrieved her smaller plug to coat it. She smiled at the camera, letting the audience know that she was already done.

Satisfied with the coating of her toy, she turned and bent over the bed, then began prodding the toy against her hole.

"Now, when you go to insert anything into your butt, relaxing your body is an important thing to remember. I know the excitement can make it quite difficult. Even with my experience, my heart has been racing since I started. I find that deep breaths are enough to calm me, but any method to calm yourself will do. If you find you can't relax, you must not force it in. Take a break or try continuing with your fingers. Now, I'll take a deep breath and..."

She took in her breath and let it out slowly. As she let it out, she pushed her plug inside. Her breath turned into a moan. 

"Mmm... Yeah... How do I look, Luna?"

"Like you're enjoying yourself."

"I am..."

"I'm sure it will be fine, sister."

"Right."

She reached back with both hands and grabbed her hips, spreading them for the camera. "I feel so wet."

"You look it."

Celestia chuckled. "Cut that part out."

"Yes, yes."

She let go of her bottom and moved a hand between her legs. "After your toy has been inserted, feel free to continue." She slid two fingers into her wet slit. Her body shuddered as she began masturbating. "You may feel a bit more sensitive during masturbation or love making with a toy in your butt. You could even leave it in and go about your day." She chuckled before pulling her fingers out and grabbing the plug. "If you're looking for a little more, try masturbating with your toy."

Celestia pulled the plug out and slid it back in, moaning softly. She kept it up for a short while before finally pulling it out. She placed it onto the bed and retrieved her viberator.

"Just like your pussy, your ass will love vibrations." she said, reaching back and turning on her toy. She moaned as she pushed it in, the buzzing becoming muffled inside her body. She began moving it, her hips gyrating to the pleasure. "Be sure not to lose yourself when using a toy with no end. You could end up pushing it in too deep and losing it. I felt so embarrassed asking my sister to get it for me. It didn't help that I came when she was pulling it out." She giggled.

She took a deep breath, steeling her will to pull out the toy. Her hole was left tingling from the vibrations. Her hips shuddered in protest. Her insides begged for more. 

She stood, picking up her dildo and the lube. "Now, I will continue the demonstration using a standard dildo." She turned to the camera, toy flopping in her hand. "I'm sure many of you are familiar with one of these. Luna, would you follow me?"

"Don't worry, I've got it."

Luna moved the camera closer as Celestia found a place for her toy on the wall. Once it was set up, she poured some lubrication onto her hand and applied it to the toy, stroking the rubber on the wall.

"It may take some experimenting to find the best position for you, but once you've found it, do your best to continue your training." she said, turning around, "Make sure to get this, sister."

"It's hard to get a good angle. What if I moved to your front?"

"You wouldn't be able to see it go in."

"It won't be entirely necessary to see it."

"I suppose. Alright, from the front. It will make it easier to talk into the camera. I'm getting close, though. I don't think it's very professional that I'm dripping down my legs."

"Don't worry about it, sister."

"Oh, you're just enjoying the show."

"Perhaps. This is a bit more fun than I thought it would be. Maybe you could try with another toy as well. The fun-"

"Stop."

"-will be doubled!" Luna said with a laugh.

Celestia grumbled. "You're a terrible sister." 

"I love you too, sister."

Celestia smiled. "Ready?"

"Ready."

Celestia took in a breath. "Once again, after you're in position, begin easing the toy into your body."

She reached back and grabbed the slippery toy, aiming it to her hole. As she pushed her hips back, she let go, placing both her hands onto her thighs. A moan escaped her lips as she took it to its base.

"Ahh... A-Again, don't expect to take it all on the first try. It's not... It's not always an easy task. Relax. Go slow. Mmm... Have a little fun with it."

She began humping her toy. More pleasured moans escaped her lips. It was getting much harder to stay quiet. Soon, she moved her hands. One moved between her legs, fingers sliding inside. The other grabbed one of her round breasts, squeezing. She moaned again.

Celestia's sizable breasts bounced with every thrust. Her long hair did the same, waving back and forth as she moved. Her eyes were beginning to drift upwards, something Luna knew meant that she was getting close. Her insides gripped the toy tightly, even with the lubricant she applied. It pushed in deep each time she hilted it. The pleasure grew more and more intense.

"Now, I am actually quite sensitive when it comes to my butt." she said, "I find it very easy to achieve an orgasm through anal play and anal penetration. You may not... mmm... You may not feel the same way. Don't be... d-discouraged. It's a new experience. As with all new experiences, all you may need is simply a little more time. After a little practice, your ass will just beg to be played with. I hope you... mmf... I hope you found my little lesson to be helpful. This has been P-Principal Celestia's Guide to Anal Sex. Have a... Ahh... Have a wonderful day!" She smiled for the camera and raised her hand to wave it goodbye. After waiting a few moments, she gave off a cry, the pleasure inside finally becoming too much for her to handle.

Though Celestia assumed her sister would turn off the camera, she did not. As the pleasure flowed through her body, Luna recorded every twitch and shake of her body. Every moan and sigh she gave off would be saved for future use.

As her climax reached its crescendo, lust dripped down Celestia's legs. Her hips refused to stop humping the toy as her fingers dipped inside over and over.

With the pleasure starting to fade, Celestia allowed her body to rest. She pulled away from her toy, her insides feeling empty as it exited her body. "Ahh... Fuck."

"We may have to redo that last part." said Luna.

"Huh?" Celestia slowly raised her head to look at her sister.

"It was good, but I think you rushed to the ending because you couldn't keep it up."

"I can't help that I'm sensitive!"

"I know, sister. I'm not blaming you."

"Well, I'm not doing another take right now. I need some rest."

Luna chuckled. "I don't mind, sister. But you were clearly lost in the moment too many times. If you want to remain educational, it may be beneficial to re-record the last section."

"You might be right. Tomorrow."

"Of course, sister."

"Were... Were you recording that last part?"

Luna smirked.

"I can't believe you. Thank you, Luna."

"It was my pleasure, sister."

"No, it was mine." She gave off a laugh. "I love you, Luna."

"I love you too, Celestia."