Twilight's Harem Havoc: Twilight's First Lesson into The Butt Stuff
#4 of Twilight's Harem Havoc
Twilight's Harem is going well so far, but now its time for Starlight and Trixie to teach her about the butt stuff.
Twilight had to admit, she was beyond embarrassed to realize pretty much everyone had seen that little scene with her, Applejack, and Rainbow Dash. Yet, even so, there was something thrilling about it. Something that made her feel desired. If all her friends were going to be spying on her like that then she must be attractive. For Celestia's sake, even Trixie was watching.
Of course, there was now a rule set in place to avoid having sex in the lounge room as much as possible. Not that it was strictly against the rules but seeing as how it affected almost everyone, it was probably best to avoid it. Looking around as she sat in her bathrobe on the newly cleaned couch she realized most of her friends had left to do their own thing. At this point it was just Starlight and Trixie in here. Trixie was wearing a bathrobe, one that was purple with gold trim. Starlight was wearing a pair of blue jeans and a tanktop that was just tight enough to reveal she did not have a bra beneath it.
Twilight did her best not to stare. After all she'd done today she was sure there had to be a limit to her lust eventually. Speaking of which she was lactating the last time she had sex, yet thankfully she had Applejack and Rainbow Dash help her with that issue. Now she was pretty sure she was safe... pretty sure but still confused as to how that actually happened.
Twilight wanted some answers and it felt like Starlight might have some. "Hey, Starlight. Do you know why I'd start lactating all of a sudden?"
Starlight nodded. "It is in part due to you being an alicorn. You see I was speaking with Cadance about a fair few things when researching for our harem, one of the things I learned was that she lactates when she gets overstimulated sometimes. Even before she got pregnant. For an alicorn it seems that hormone levels can go crazy and it will produce milk. Another reason could be that well... you know how every alicorn seems to represent some kind of theme with their god-like powers?"
Twilight nodded. "Yes, the hormone thing makes sense but what would my godly powers have to do with anything."
"What if you were the alicorn of lust? Cadance is love, Celestia is the sun, you know when she's not being lust herself, and Luna is the moon, again when she's not being lust herself."
Twilight stared at her. "Are you suggesting that me, Celestia, and Luna are all the alicorns of lust in secret?"
"Scratch that, all four of you are," Starlight laughed. "Honestly, kinky alicorns is far from the worst possible thing."
Twilight scratched at her chin in thought for a moment. "I suppose that much is certainly true. I think I could enjoy some kinky alicorns myself."
Trixie giggled. "As could Trixie."
Twilight glanced at her. For a moment she forgot that Trixie was here. In fact, Twilight had screwed every member of her harem so far, every member except for Trixie and Starlight. Twilight grabbed at her seat. "Trixie, are you really excited to be here?"
Trixie stared at her. "Trixie loves it here, Trixie loves you. The Great and Sexually Active Trixie, desire you in the most depraved of ways and wishes nothing more than to be intimate with you post-haste, but she will wait until you deem her worthy of your attention... it has to happen eventually... right?"
The last word Trixie said came out meek, and the look in Trixie's eyes looked a little scared or hurt. It was a vulnerable state that Twilight had so rarely seen Trixie in. One part of her, a part Twilight really hated wanted to take this opportunity to hurt Trixie. To break her heart and watch her cry. Yet she shoved that part away, she'd already done that once, and ever since she'd felt guilty about it, especially since Trixie had proven she was a good pony, a truly good pony willing to sacrifice it all to help out. Twilight hated that part of herself, but there was another part of her, one that wanted to take Trixie then and there and who cares if everyone saw it.
Twilight offered a smile to Trixie. "You know, I've been with almost everypony so far, I wouldn't mind if the next one I'm with is the two of you."
The smile Trixie gave her was such an honest one that it made Twilight's heart skip a beat. "Trixie knew you were the right choice."
Starlight clapped her hands together. "Alright, well I guess we have the rest of today's agenda settled."
Twilight looked at her. "What do you mean?"
"Though I'm not going to directly participate yet, I am interested in helping you further your sexual education, Twilight. Trixie would very much enjoy being your study buddy as well."
Trixie grinned. "Trixie will be your study butt."
Twilight raised an eyebrow. "Study butt?"
Starlight laughed. "From what I've heard you seem to have picked up a certain interest and Trixie is more than willing to help you practice your newfound fascination with rear ends. Tell me, what is the largest thing you've put in your ass, Twilight?"
Twilight's yees widened. "I have never put anything in there!"
Starlight tapped her fingers together. "Okay, guess we start at level one and work our way up."
"L-level one? Wait, Starlight, what are you planning?"
Starlight shook her head. "Once we actually start you must call me Miss Starlight. You will be my student and I will be your teacher. Is this understood?"
Twilight nodded. Somehow the idea of Starlight playing the role of teacher was even sexier than she could think, yet she did have a small request. "Starlight... could I ask a favor?"
Starlight nodded. "Ahem, if you ask correctly you can."
"Miss Starlight, can I ask a favor?"
"Anything to help my precious student feel more secure and safe."
"Could you wear a pair of glasses and tie your hair in a bun?"
Starlight laughed. "Is that all? Okay then." Her horn lit up and Twilight watched as Starlight's mane tied itself into a bun and a pair of square-rimmed glasses appeared on her muzzle. "There, all ready?"
Twilight nodded. "Yes, Miss Starlight."
Starlight looked over to Trixie. "How about you, Trixie?"
Trixie nodded. "Trixie is ready too, Miss Starlight."
Starlight clapped her hands together. "I'm so glad. You might both earn a gold star sticker if you keep up the good behavior."
Starlight picked up her cup of coffee and took a drink. "Now any questions from the class?"
Twilight shook her head. "None yet, Miss Starlight."
Trixie grinned. "Trixie has one, Miss Starlight."
Starlight smiled at her. "Go ahead."
Trixie was grinning. "When can we start? And where do we start? And what are we doing?"
Starlight rolled her eyes. "That is technically three questions but I can see you're excited to learn. I do love it when my students are happy about furthering their education. First, we can start right away if you two would prefer, second we will start in Twilight's room, I've already set up everything there. Third, we are going to do some practice with toys, as well as having an introduction to anal. From what Pinkie says, Twilight here is interested in that."
Twilight swallowed. "Miss Starlight... it doesn't hurt does it?"
Starlight smiled. "Only if you do it wrong, and trust me I am a kind loving teacher, I'd never hurt my students."
Spike stood at the open doorway. "You know what, I don't think I wanted to know about Twilight trying anal... at least I hope I didn't. Oh god, I think I might have wanted to know that."
Twilight glared at him. "I will entertain you later, Spike, I am being a student right now. Go be the adult you are and have sex with Rarity or something."
Spike opened his mouth, stopped, and then shook his head. "I'm going to take that as permission to borrow your harem.... okay cool, hopefully, Rarity or Pinkie is here."
Starlight called out. "Neither of them are here, but Fluttershy is, and I hear she likes her dragons young."
Spike's eyes widened. "Fluttershy would... with me? But she's like super hot and shy."
Starlight rolled her eyes. "Go ask her yourself, I'm sure she'll make you feel good. Otherwise, you can join our anal lesson, trust me, anal feels good for men too."
Spike turned around. "I'm going to go ask Fluttershy to uh, sex with me or something. You can keep your butt plugs to yourself."
Twilight watched him leave and then looked at Starlight. "What's a butt plug?"
Starlight giggled. "Oh, Twilight. That's not until lesson two."
Twilight stood up. "I'm actually really excited now, can we, you know... do the thing, Miss Starlight?"
Starlight downed the rest of her coffee and stood up. "Yes, yes we can. Oh, question, have you gone number two today, Twilight?"
Twilight wasn't exactly comfortable with answering that question, but she figured it was probably important given what hole they would be exploring. "N-not yet. I hardly even went pee."
Starlight shook her head. "I'm going to give you an enema and we'll have to wait until you clean out your system before we really start. I mean, I don't mind either way, but Trixie's nose is a bit more sensitive than mine and you might feel embarrassed if you smell yourself."
Twilight shivered. The idea of what was being implied was more than enough for her to want to accept the enema. Of course, what she did not expect was for Starlight to drag her to the restroom and personally give her the enema. Nor for Starlight to stay there during the process watching with almost judgmental eyes. Trixie wasn't looking too much more pleased with the scenario herself but at least she looked more ashamed or embarrassed. Once that humiliating event was done and Starlight double, tripple and even quadruple checked to make sure Twilight was thoroughly clean down there, going so far as to smell and lick, why in Celestia's Equestria did she lick? Starlight declared, "You have done very well, Twilight, you might just get an A+ if you keep up the good work."
Twilight's eyes widened. "A+!" okay, she changed her mind, going potty in front of Starlight was worth it if she got an A+.
They next made their way to Twilight's bedroom where Twilight saw a few water bottles on the floor near the bed as well as an assortment of plastic toys, half of which Twilight couldn't recognize and a bottle of lube. Starlight smiled as she instructed the two of them to strip completely. Well, Twilight had already been in a more embarrassing spot so stripping was nothing compared to her earlier torment.
Starlight instructed Trixie to lay herself on the edge of the bed on the opposite side of the toys. Making sure to stick her rear and legs over the bed for easy access. Starlight proceeded to take a black cloth and wrap it around the base of Trixie's tail keeping the hair out of the way and making it easier to Twilight to see the perfect shape of Trixie's ass. Twilight swallowed as she stared at it. Her body was growing hot again and she couldn't do much other than imagining all the things he was going to get to do with Trixie, as well as just how willing Trixie was to do them all with Twilight.
Starlight moved behind Twilight and wrapped her hands around Twilight's waist pulling her close against her. Twilight gasped, "MIss Starlight!"
Starlight leaned up to Twilight's ear and put her lips to it giving it a gentle nibble. "Now we're going to start the lesson, first we show you how it works, and then we go to practice."
Twilight swallowed. She was really doing this wasn't she? She was going to have things in her butt now... and somehow despite the idea of it being a little scary, with Starlight's promise that it wouldn't hurt, that it would indeed feel good, she was one hundred percent down to try it. After all, Pinkie had so enjoyed just a single finger in that hole, what would Twilight get to enjoy? Her mind was already beginning to fog over yet this was still a lesson plan and she had to fight with her mind to stay alert so she could fully grasp every part of the lesson.
Starlight walked Twilight forward and then knelt her down right in front of Trixie's rear. "Now, Twilight, be a good girl and spread open Trixie's butt cheeks for me would you?"
Twilight reached out with her hands and firmly cupped each one of those soft bubbly cheeks. For a moment she hesitated but slowly spread it open to reveal not only Trixie's pink pucker, but also her marehood already winking at her and drooling against her leg. Twilight could smell it now, the scent of fresh meadow flowers mixed in with something a little more acrid, a smokey scent that made Twilgihts' head spin a little. She had to focus Starlight was teaching her something and she needed that A+.
Starlight let go of Twilight from behind and walked over to the bed where she reached over and grabbed the bottle of lube. After opening the top she began pouring a large amount of it over Trixie's open rear. Trixie gasped as the fluid landed on her. Starlight explained, "When it comes to anal some ponies can do without any lube, or just some saliva, but for the most part if you want to avoid any pain or other consequences lube is required. After all this hole is only meant for one-way transit and we're kind of breaking that rule of nature for anal sex."
Starlight began massaging the lube into Trixie's rear putting the majority of her focus on Trixie's pucker. The soft noises of pleasure Trixie made were so attractive, so alluring. Twilight wasn't sure it was actually okay to be listening to this. Yet here she was, staring at Trixie's most intimate areas, open, exposed, and being massaged by a hand that clearly loved Trixie in a deep and intimate level. It almost felt like Twilight was intruding on something by being here, but they both wanted her here, so she'd do her best to make them happy.
Starlight's finger slipped inside that hole and Trixie gasped once more. Starlight pushed her finger in deep and it slid in with little resistance. With slow gentle motions Starlight moved her finger in and out of Trixie's rear. The cavity pulling with the finger as it pulled out as if trying to greedily suck the finger back in. Starlight then slid a second finger in and Twilight gasped this time seeing two whole fingers go into that hole. Trixie was making soft noises with each push and pull. Starlight explained, "We've been training her a lot here. She can handle three whole fingers now. I'm hoping to get to four soon, but I'm hesitant to do any more. You can cause damage if you go too big and I'd prefer not to hurt my lovely little magician."
Starlight slid her fingers out and nodded for Twilight to try. Just Twilight was about to slide a finger in Starlight's voice came out gently. "Actually, try this." a small toy, perhaps no larger than a marker was given to Twilight. It had bumpy ridges along the side and Twilight didn't have to be a genius to figure out what to do with it.
Twilight pressed the tip against Trixie's hole and pushed in letting it slide in. The way her anus swallowed each bump over and over was almost magical in itself. Twilight nearly slid the entire thing in before stopping and pulling it back out bump by bump. Trixie was groaning with the motion of each bump. Starlight was smiling. "Good job, Twilight."
Several minutes went by as Twilight worked the toy in and out, steadily moving it faster and with greater ease. Trixie's marehood was sopping wet at this point and it was clear she wanted more, she was surely close to the edge now but just before Twilight could suggest moving forward Starlight grabbed the toy in the middle and pulled the rest of it out of Trixie. With Trixie's cheeks spread open her anal cavity actually stayed open for a moment before it closed with the toy removed letting Twilight see inside of Trixie.
Starlight then patted the bed next to Trixie. "Your turn to go on the bed now, Twilight."
Twilight took much the same position as Trixie and looked over to see Trixie's sweat-covered face as she smiled. "Hi."
Trixie replied. "Hi."
Starlight spoke. "Now open your butt cheeks, Twilight."
Twilight placed a hand on either side of her rear and spread her cheeks open for Starlight's sake. Starlight took the time to wrap a similar cloth around Twilight's tail to keep it out of the way. Once that was done she began pouring the lube over Twilight's anus and Twilight gasped,it was cold. Really cold. It wasn't until Starlight began rubbing the lube in that it began getting warm, hot even. Twilight's entire body was tense, she saw how easily and without warning Trixie had a finger shoved in there, she was a little worried about what it would be like on herself.
Starlight spoke gently. "Relax, Twilight. if you don't relax the muscles it's harder. Good girl.... now are you ready?"
Twilight was about to reply when she felt something slip inside her rear. It hurt a little but the deeper it went the more she felt something odd. She felt good. There was a finger in her ass and from the way Starlight's hand pressed against her skin she was sure it was all the way down to the base. How could something like this feel so good? The walls of her rear entrance were spread open for that finger. Then the finger began sliding back out and Twilight loosed a tiny moan as she felt her body reacting to it. The finger slid almost all the way out before stopping. There it stood, just the tip of it inside her, waiting, unmoving, Twilight wanted more. She needed it back inside her.
Twilights' voice came out small, and weak. "Teacher, Miss Starlight."
"Yes, Twilight, my faithful student?"
"Please put your finger back inside."
Twilight was rewarded with the finger sliding back into its new home. The friendly visitor slid itself in and out of her rear, moving steadily faster with each motion. Twilight felt it, her nethers were burning for attention too but she was here to learn, she wanted that A+. She was pretty sure she wanted it more than an orgasm. Each time the speed increased there was a small burning pain but it was quickly replaced by pleasure. Twilight wanted more fingers inside her, but she could only try and stay quiet. Moaning every now and then if the finger got particularly deep.
Starlight pulled her finger all the way out. "Good, you seem ready for lesson one to really begin. I'm going to use the same toy you used on Trixie." Twilight wondered if Starlight had even cleaned it first, or if she even cared enough to wait for it to be cleaned. There was silence for a moment. "Also we're still having sex, so you two can still kiss each other and touch too."
Twilight felt the tip of that toy push against her backdoor. She tried to relax so it could slide in with greater ease. Each bump was like a fresh wave of pleasure and she could feel the bumps moving inside of her. By Celestia's solar heat, this was amazing. Twilight didn't think it could get any better as her body was burning from the passion already. She was close to a climax and she'd only had a toy in her ass. Trixie's lips moved over to Twilight's and they kissed. Twilight could taste it on her tongue, the smokey flavor, the wildflowers. The hot tongue in her mouth was the final key to unlocking her puzzle as Twilight's body jerked and she groaned as her brain fogged over and she relaxed deeply onto the bed.
Trixie giggled. "Orgasm from your butt, feels good doesn't it?"
Twilight's leg twitched and the toy was slid out of her. Starlight kissed Twilight's butt and stood up. "Good girl. I think you both deserve an A+ for this."
Twilight closed her eyes and relaxed there. She was done. So much sex in one day, she couldn't possibly see anything else being this good again. Until she realized this was literally day two of her owning a harem. There were going to be many, many more days like it, and she was going to learn a lot more.
Starlight's hand slapped Twilight's ass cheek just hard enough to make her open her eyes. Starlight laughed. "Think you get to go to sleep yet? Trixie hasn't even been satisfied yet you selfish slut."
Twilight looked back at her. Something in her heart shattered and she felt it as her entire body tensed up. "Am I r-really a slut?"
Starlight met Twilight's eyes and her face paled. "No, it was just dirty talk. I didn't mean it."
Twilight sniffled. "Then why did you call me a slut?"
Starlight reached out and stroked Twilight's cheek. "Shhh. I didn't mean it. Some ponies like to be called bad names in sex. I won't do it again."
Trixie cooed. "Aww, Twilight's so fragile after coitus. Trixie will keep that in mind."
Twilight looked at her. "Why?"
Trixie leaned forward and kissed Twilgith gently. "So that I make sure I never hurt you, not you my love."
Twilight began kissing Trixie back as she watched Starlight take off her back to reveal a strap-on. She positioned it at Trixie's backside and paused. "Trixie, what hole would you like me to take today?"
Trixie purred. "Since it's my first time with Twilight, I'd like you to fill my mommy hole."
"Vaginal it is then." Starlight said as she slid herself into Trixie.
Trixie moaned as Starlight pressed herself deep into Trixie. Twilight leaned forward and continued kissing Trixie as Starlight began thrusting her hips sliding her toy in and out of Trixie. Blue fingers wrapped around Twilight's lavender fingers. Their tongues met and even with Trixie moaning through it all they kept kissing as Starlight moved faster still. Soon the sounds of her flesh slapping into Trixie's rear was so loud it drowned out the sounds of Twilight and Trixie's kiss. It wasn't long before Trixie had to pull away, her eyes were firmly on Twilgihts as her face screwed up and she hissed.
Trixie's body went straight as a board, her eyes nearly popping out of her head and her hand's death grip on Twilight's so tight Twilight feared she might lose her hand. Starlight pressed herself deep and tight against Trixie's body, leaning forward over her and wrapping her arms around Trixie, and kissing the side of her face. Trixie stayed like that, tense and rigid for several long moments before her body began relaxing. Trixie's hand relaxed against Twilight's and she smiled. "I love the two of you so much."
Starlight kept kissing Trixie's cheek. "I love the two of you too."
Twilight closed her eyes this time for real. "I love you girls."
She felt Starlight's lips press against her cheek and relaxed further still. Twilight was content to lay there and go to sleep. So long as nopony called her any names again. That was positively horrible, how could any pony like that? Was she going to have to do that to her friends? To Starlight? She wasn't sure she had it in her to be so cruel. But if they really wanted it she would give it to them. Her love for them had no bounds after all.
***
Celestia was sitting in the royal dining room enjoying a significant portion of cake while Luna handled the other half. She was positive that things were going very well down in Ponyville and their harem was being trained very well, specifically Twilight was being trained very well. By the time they got there to use the harem, she was certain they'd be well prepared for them.
Luna chuckled to herself. "I just realized we forgot to tell Twilight a few important things."
Celestia smiled. "Like how she's going to start lactating as her sexual prowess comes into play."
Luna rolled her eyes. "You still lactate, your lactating right now dear sister."
Celestia looked down. There were a few damp spots on her dress where her nipples were. "Well... guess I'm excited."
Luna smiled. "No, I meant that she might be capable of impregnating her friends with enough sex."
Celestia laughed. "They can use contraceptive spells... I made sure that Starlight knew to use those. Even so, I would not doubt if a year from now we have a parade of pregnant ponies on our hands."
Luna grinned. "Pregnant mares can be better than others sometimes."
Celestia licked her lips. "Of this, we can surely agree on."