Chapter 2 - Tutor's Pet

I can’t say things became perfect after we started actively dating, but I can assure you, we did clean ourselves up a bit when we did. Our house is no longer the pig sty it used to be, a little motivation from threat of eviction will do that for you.
 
As well, my brother started to really value his job, and that change in attitude didn’t go unnoticed, he soon got promoted from ‘store slave’ to ‘company slave’ and would now work as head manager of the store. We happily celebrated the occasion with a maid costume, some fluffy cat ears, a soft and very satisfying ‘tail’, that led into some butt fun at my expense, too symbolize the fact that he would be doing the butt-fucking from now on.
 
Anal for the first time was absolutely heavenly for me, but my coworkers definitely knew what happened from the way I walked the next morning. On that note, I finally opened up at work and made some new friends, I figured they’d be ‘normies’, so when we had a two hour long discussion about this obscure, random-ass, yaoi manga we all happened to read in high school, I knew I was in good company.
 
Now that Oliver was the manager, he makes a dime an hour instead of a penny. A dime well used to buy a better fan, It was one of those blade-less air multiplier ones. We said our final goodbyes to our old, well-loved, box fan, as we gave it to the older couple that lived downstairs and needed it more; rest easy, my windy warrior, you were a true soldier, who stuck it out in a losing battle. Tears aside, that new fan was put to great use pretty much immediately too, as we needed it to cool down from all the fucking we were doing.
 
We kinda went a bit crazy after our first time. Every position, everyday, for hours on end, I was getting absolutely railed, just banged out, by my little brother’s fat cock and, god damn, I was loving every moment of it. As soon as the other got home, clothes were off, and we were ready for a long night of bed breaking and moan making. We actually had to buy a new, quieter, memory foam mattress from all the noise complaints we were getting.
 
If you’re wondering if the topic of incest ever came up. No, it did not, and no, I don’t know why. We weren’t exactly subtle about our relationship; I’d dare say, ‘irresponsibly’ so. I figured that, maybe our neighbors were just too busy with their own lives to care about what a couple of mid 20s nerds were doing in their private space, so long as it doesn’t bother them, have at it. Maybe they just wanted to avoid having that ‘talk’ all together and didn’t confront us for the sake of keeping their own sanity. The answer escaped me, I could only speculate, but either way it made our lives easier, and if we can live in peace with our ‘less than wholesome’ family dynamic, than hell yeah, I’ll spend some extra money on a better, comfier mattress, and buy a couple of sound absorbing foam panels to stick around the room, if it makes our sex quieter the next time my brother is fucking my brains out than, it’s well worth the price to be more considerate to our neighbors, who are kindly looking the other way when it comes to our relationship; It’s a good trade, I think.
 
I must admit though, despite how great it felt to have his, just truly, magnificent cock buried in all three of my holes, I was hoping that my dick could get wet, and explore a cave other than the throat it was accustomed too.
 
I had come to realize that I was a bottom, absolutely, but not exclusively one. I had heard the cry of the ‘beast’ that resided in my brain, and it was a war-cry demanding topping action! It desired to fuck, and that ‘ape brain’ of mine would not be satisfied til I did.
 
So, after a good month and some change of saving and planning, I had completed my prep work, and on one, average, Saturday morning, when we were in each others arms, cuddling under a cozy blanket, on our bed, in the blue gaze of a tiny laptop that rested on the table in front of us, watching some late 90s anime, he was trying to show me ‘Outlaw Star’ I think, I finally popped the question.
 
“So… uh… When can I finally fuck your ass?” I felt we were at a point in our relationship where dancing around ‘the metaphorical bush of embarrassing topics’ was no longer necessary.
 
He didn’t look my way, but he gave an audible hum before he took me for a loop with “Damn, I thought you’d never… whenever you want, duh. I’ve been waiting, waaaaay, to long for you to lay this offer on the table.” His, rather rude, answer struck me. His eyes were glued to the screen, which told me that he wasn’t, repulsed by the request, and his nonchalant response told me that we were on the same page… I s-suppose?… But I must admit, I was shocked at how quick and thoughtless the answer was...
 
Well not really, after some thinking, I wasn’t really shocked that he agreed to it. Our relationship isn’t much of a ‘giver/receiver’ type, much more of a ‘taker/supplier’ one.
 
Still, I had to at least feign surprise and with a “Huh...Really?” I had to know “Why didn’t you just bring it up to me before, then?”
 
He took a moment and turned away from me, with a face that was clearly embarrassed, and red enough to glow. All he could mutter in response was “Cause… well… I’m a little nervous…”
 
My face perked up at the reaction, he was always just so, god damn, cute when he was genuine! I hugged him, hard enough for him to heave, and assured him it would be okay.
 
“You’re too sweet for your own good, sometimes, you know.” I kissed him on the forehead and got up from the bed. I found a disposable enema that I had stashed away in my ‘not-so secret’ box of ‘girl stuff’ and threw it at Oliver.
 
“I know you know what that’s for, but do you know how to use it?” I questioned him with a ‘no stupid questions’ tone, but I was quick to learn it wasn't needed.
 
He looked down at it intensely, apprehension in his throat, and gulped out “I can guess…” His blush brightened, as he held the bottle in a shaky grip. There was no easing this uneasiness, but I attempted.
 
“I promise you, your fear is unwarranted, it’s not that bad.” I put a hand on his shoulder in an effort to calm him down.
 
He looked up at me and back down at the bottle, lips dry with concern, and sweat down his brow “I guess I can trust the expert, then...”
 
“I absolutely can assure you that it’s not... that... bad...."I paused for emphasis "but you won’t change you mind till you use it, so go use it, and then go take a shower.” I then clapped my hand together in excitement, as if I were to make a grand announcement, and smiled Ollie’s way “After you’re fresh and clean, the real fun can commence!” but Oliver’s face had not changed from his grimace and I knew, whatever he anticipated was not worth fighting him on.
 

 
I’ll spare the gory details, but know it was rough. Seeing Oliver, as he walked dead eyed out of the bathroom, was a sight I couldn’t help but laugh at, his despondent look, as he went to grab his towel for the shower, would’ve certainly been the highlight of my day, if I didn’t know what was in stored.
 
He turned to me with his face to the dirt and spiritlessly said “I’m sorry, if I knew that this is what it felt like to prepare, I wouldn’t ask for anal.” He was slumped over with a slack jaw and a dull mind, I guess his first enema drained his soul with everything else.
 
I tried to cover my giggle with my hand, out of courtesy, but I couldn’t help but tease him just a bit. “You big baby. You’re over exaggerating, once you get used to it, it honestly feels kinda good to be, you know... 'empty'... I guess!”
 
I tried to be cheery, to raise his spirits, but the monotone “Doubt it…” that was all he could quip with, told me he just need to shower off his grief.
 
Still I reminded him “Remember, the reward is well worth the preparation.” and I gave him a wink and smile to reassure him, but I could see no change in his mood.
 
“Yeah… Let’s hope…” He started for the bathroom, but was distracted by the two wrapped objects that lay on the bed. “What’s in those boxes, anyways.” he asked, as he pointed to two gift boxes I had prepared for this day.
 
“A surprise! One that you’ll see when you finish your shower.” I did little finger wiggles towards him. My excitement to see my plan unfold made me feel extra energized today, and I wanted to share it with Oliver; just enough to get him out of this, honestly unnecessary, funk.
 
“...alright I guess. I’ll try not to keep you waiting then.” He gave me a faint smile before returning to the shower, dragging himself into the bathroom with the little willpower he’d retained.
 
I would’ve loved to offer him some ‘assistance’ in there, the thought of a sexual ‘pregame’, before the real horny event started tempted me, but my grand scheme for today was far from complete, and I needed to make sure everything was perfect. Thoughts of groping his soft ass, under warm beads, that steamed an arousing heat will not distract me. I will stay focused, but damn, the allure was strong; Pray tell me, great Goddess, ‘Hermaphroditus’, Why do you give your hardest challenges to those with the weakest wills? But I stayed the course.
 
“Don’t worry Ollie! Take as long as you need!” I yelled at him from outside the bathroom, as I then waited for the shower to turn on. I wanted to make sure he wouldn’t walk out early and ruin his surprise, but I got quite annoyed at how long he made me wait, kinda brought that on myself, not gonna lie. Little bro had to find the perfect, ‘city pop’ playlist, I guess, couldn’t just pick one of the thousands available on Youtube; what did they just not have that right 'shower' feel? I sighed, and continued to the next step when the water began to run; everyday is a good day when phones exist to cure impatience.
 
The coast clear, I placed a small pocket mirror on the table in front of me and sat cross legged, before I pulled out my high school make-up kit and applied it’s contents, for the first time, in a long time. I was worried I’d make myself look like a clown, but that fear was unfounded, as it was a lot easier than I thought it’d be; guess the muscle memory never left.
 
I was going for a cute, pinkish, e-girl look, the type I saw Oliver simp over on twitch, every now and again; there's no jealousy, they could never compete. I had watched a couple of tutorials online and practiced what I learned, I applied pink eye shadow with shiny lip gloss to match and gave myself a rosy blush, adding the extra detail of faux freckles that I dotted on my cheeks. The hard part was the eyebrows and mascara, I flinched a couple of times with the brush so close to my eyes, but eventually, I was able to give myself that cute flourish that I knew he’d appreciate; I even added a little heart under my right eye as an adorable, little detail. I brushed my hair so, that my usual shaggy curls were nice and curvy, I had let my hair grow out to my shoulders. It had a nice bounce and volume to it, and with a cute little ribbon-shaped hair clip to complete the piece, and keep my bangs out my eyes, I was done.
 
I’m usually the self-deprecating type, so when I saw my finished work reflecting back at me, I was surprisingly pleased. I took pride in my appearance, and told myself that I’d have to do this more often. It’s actually kinda fun to doll up, but remembering that this case is a hand me down from my cousin reminded me that I’ve never actually bought make-up before; the stuff was far too expensive for my budget, and I'm not dipping into the figure fund to look pretty. I’ll have to get back in touch with, Isabelle, sometime, maybe I can get some tips… if she doesn’t find out about the incest stuff, I guess.
 
I was taken out of my self-admiration, and was reminded of my goal when the sound of running water could no longer be heard. I sprung into action, and leapt for the smaller box, tearing it open to retrieve the reward inside. There was still work to be done, and I had barely anytime left. I know he’ll love his first surprise, so I can’t fuck this up.
 

 
It didn’t take him to long to step out of the bathroom, but I was granted far more time than I needed. I can’t be to mad though, from the ‘swishing’ sounds and gargling, I guessed he decided to brush his teeth, which was odd considering it was almost 2PM now, but the thoughtfulness will not go unappreciated, as the time allotted gave me ample room to be detailed oriented with the surprise.
 
With due time, the door had finally slid open, his foot jutted out to make contact with the main room’s carpet, and he stepped out, pushing up his glasses to say “Heh, kept you waiting, huh?” The fact that I was fighting myself to not smile, goofy, at this moron’s unfunny, reference one-liner, is more than enough information to tell you how are relationship is going, I think.
 
A towel covered his waist as he walked out, still dripping just a bit from his shower, his lovely, pudgy, frame glistened with straggling droplets that glided down his rosy skin. He ran a hand through his soaking chestnut hair, to slick it back out of his eyes, and revealed circular frames, opaque from the shower’s steam. Even with my locks grown out, his hair was still longer than mine, reaching just at the base of his neck; hell if he didn’t have to cut it for his promotion, it’d probably roll down his back by now. Still, his wet mane reminded me of how attractive I thought he was.
 
My face burned a hot red, and I drooled looking at him. My adorable younger brother was a stud, the type you’d could imagine as a life guard who just climbed out the pool in full splendor... well… that is, if that life guard drank nothing but ‘Mountain Dew’ and ‘Red Bulls’ and couldn’t read a book unless you put it no more than 5 inches from his face, but I digress. He was SO handsome, and I could ‘squee’ like a school girl just by looking at him, but I kept my composure, and as his glasses began to defog, and he could get a better look at me, my excitement for his reaction began to boil over.
 
He looked me up and down and took a brief pause before he stabbed me with “...what the fuck are you wearing?” His face was blank and nonreactive. This was absolutely against my plan, but I figured I just had to sell the display, maybe the surprise was too... ‘surprising’? So, I answered his apathetic question with enthusiasm.
 
I struck a pose and gave a peace sign. “I’m dressed as a school girl! One that’s going to take you on a wild anal rodeo!” I changed my pose to one that emphasized my cleavage. I pressed my breast together in an effort to highlight my chest for him, blowing a kiss his way in order to seduce him with my womanly charms, but the look on his face told me he was less than impressed.
 
I had gone through the effort to find a school girl outfit for him, it was more of the western kind with a bit of eastern influence; as described by the website I bought it from. I wore a cream colored short-sleeved sweater, with indigo accents on the hem, collar, and sleeves which came down just before my elbows; a lovely, blue, string ribbon topping the piece as it hung, loosely, around my neck. The skirt I wore was plaid made up of navy blue squares and white and black lines, it came down to my thick thighs and was met by a small valley of pink skin, that was enveloped by black knee socks that ran down to the carpet below.
 
Point is, I paid a pretty penny for this cosplay, and to be met with not more than a blank… “Okay, but why are you wearing that.” Was, far, more than a little agitating, but I didn’t let that break my cool.
 
With a seductive voice, I reached to caress his cock, and whispered in his ear “Cause I’m going to be teaching you today” blowing cool air into it, for added effect.
 
But, besides a slight blush, and the feel of his stiffening erection, his attitude had not changed “Shouldn’t you be dressed as a teacher then like, what are you my tutor?” He swatted my hand away and put his hands at his waist, as he judged with a glare that reflected from his specs.
 
I was more than a little ticked now, but was not deterred. I cleared my throat “Teacher’s aren’t as cute as their adorable students!” I responded holding back my anger with a smile that was forced to remain upon my face.
 
But was only met with a sneering “I beg to differ.” As he crossed his arm and turned his nose up. “A mature sunflower will always be more gorgeous than the youthful green sprout it came from.” Did he, fucking, just make that up on the spot!
 
I boiled over and fizzled out, I groaned, clenched my teeth, and gave one last halfhearted attempt to get him in my corner. I put my finger to my cheeks and stood with my weight on one leg “Just think of me as your ‘senpai’!” I struck another pose, a hand on the hip, and pointed another peace sign his direction, but this pose was lacking the enthusiasm of the last few. I wanted to pretend that my mood wouldn’t be broken, but it was cracking at the base.
 
Still he wasn’t even just a little bit aroused, and stared me right in the face, and had the nerve to say “I think… yeah, I think I’ll think of you as annoying, instead.” A smug grin crept across his face. He was clearly satisfied at the insta-mood-killer he just scored against me.
 
But, I sure as fuck wasn’t. All that planning…. all that time…. I spent soooooo much money...
 
So I pouted, defeated, and told him to “Just… just fucking open the other box... er… fucking... whatever… WHATEVER!... fucking… uh…” I had lost my fight. I had lost my will.
 
I had lost, all my hard work, the thought I put into this, the effort I had to go through to find these clothes and dig up this make-up box, just for my vibe to be killed by my own brother… It’s always the people you trust most...
 
Yet, he seemed to not care, his eyes now glowing at the idea of opening a present, and with a smug
 
“With pleasure, sis.” He sauntered over to the larger, unopened gift-box, and ripped it apart, savagely and far more eager than he was to see me be ‘pretty’; I’m not mad… I’m not upset… the rain can’t keep me down.
 
As I coped, I figured, considering his non-reaction to my cosplay, he’d care little about what was inside, but my brother wasn’t so easily predictable today.
 
“Oh shit, this is cool! It’s like a Hogwartz uniform, but not lame!” He held up the matching cosplay with bright eyes, and without even prompting him he was already in it, how the fuck did he get dressed so quickly? I had only looked away for a second and he was already mostly done.
 
“Well, this is pleasant!” I said with a smile returning to my face “I’m glad, and surprised, you didn’t hate it considering how you reacted to seeing me in the same attire.”
 
“Nah, this shit’s cool. I look dapper and shit. I feel like I could wear this out for fun too!” He was grinning ear-to-ear, as he put his belt on, and I thought about it for a second, and came to the conclusion, that that wasn’t a good idea, and he probably shouldn’t wear this in public, he’d look far too, preppy, and not at all like the gentlemen he thought he was, but I didn’t have the heart to tell him; I couldn’t crush joy that pure.
 
My brother was very handsome in his uniform. It was much the same as mine, he wore a sleeveless cream sweater, with an indigo long sleeves underneath, his pants were the same type of plaid as my skirt, a tan belt popping out against the navy blue, and his socks were the same black, but only came up to his ankles. I’d say, we looked cute in our matching display, a proper couple, well we would if only he could stop struggling with that neck tie, that is.
 
“Hey Chloe, could you help me with this? I’ve never been good at tying ties.” I saw him create some of the most ‘unique’ knots in his fruitless attempts to put it on, and I knew it would be 'big sister’s' job to help him.
 
So I sighed, “Silly Oliver, what would you do without me.” and helped him with his tie, and with a good tug to finish his outfit, I couldn’t help but admire my brother when he actually dressed nice, his full-moon specs gave him an intelligent air, and his long hair made him seem laid back and warm, almost scholarly even; if he could grow facial hair, I might confuse him for a professor, but I knew this dumb ass too well to know he could never teach. I smirked to myself in my head, if we could 'tie-the-knot', I’d look forward to more moments like this.
 
“You know bro, you look quite ‘fetching’ like this. You should try to dress formal more often.” I smiled at him, getting another visual ‘up-and-down’. I’m so fortunate that he’s my brother.
 
“Ah, thanks sis! I’m glad you bought this for me, It’s a great gift!” He gave me a warm smile, as he stared into my eyes. I wrapped my arms around him and held him close, enjoying his warmth, but pouting as I remembered what happened just before.
 
“I just wish you felt the same about how I dressed…” I put my head in his chest and sighed, let down that I couldn't see him flustered by my effort.
 
He looked down at me and laughed “Oh! Oh no! I think you’re fucking hot, sis. When I stepped out, I was bricked up, for sure, but I can’t help wanting to annoy you sometimes, so I played it off to see your adorable pouting face, sorry if I made you feel bad. I love the effort you put into this, you look stunning and great.” He gave me a hug back, but the love was not returned; I was livid.
 
I’m not going to lie, I wanted to kill him, I wanted to wring his neck with that stupid tie, but I relaxed, it felt nice to know I’m still, so very, attractive to him, and sometimes I almost forget he’s still my impish, idiot, brother. So, I settled with a threat, instead of active and immediate violence.
 
“You know, we can just skip the foreplay, and I can go raw with no lube, right? I might be smaller than you, but you know, I’m certainly not 'small''". I tapped his noise playfully and the tone of my voice was of the same attitude. I might’ve even fooled someone into thinking it was just me, joking around, but my brother knew me, and he knew this smile, so he knew better, than to, ever, try this stunt again, lest our next session be practical application of CBT.
 
He sweated and hoped to alleviate the tension with a “But, then you’d miss the foreplay, t-that’s your favorite part, r-right?” He rubbed my back, and gave an awkward laugh as he tried to dissuade me from being rough with him. Thankfully for him, I’m a merciful elder sister, and will collect my debt later, so I hugged him snugly, and exhaled relieved, letting him ease up, knowing he was safe to live another day.
 
“Hmm, I guess... I guess you know me to well. You’re right, I don’t want to miss out on foreplay. I want to get you nice and prepared for your exam. How about we refresh on some previous material.” I pulled him down by the tie, and we shared a kiss. Our tongues explored two caves they were well familiar with. It was a practiced dance, and before it was over, I sucked on his tongue, and squeezed his ass when we broke apart, getting a quality moan that satisfied me enough to move forward.
 
“You know what, you gave me a great idea earlier. Yes, I think I will be your tutor, and you will be my special, little ‘kouhai’, who is very much in need of an extra thorough session. So lay, back and get comfortable on our bed. Senpai’s gonna guide you through this lesson. Just be aware the material covered will be a little ‘hard’ going in.” I put a hand on his chest and gently pushed him onto the bed.
 
He blushed and made a goofy face, that made it clear I was on the right track, and shyly, he requested “Please do senpai.” and I sighed relieved, knowing that I got his confirmation that he was willing to role play; I’m glad he was open to try new things, it was more fun for both of us that way.
 
“Okay, before we get to the main material I have to prep you. I can’t go in raw with new information, I want you to enjoy yourself, and if I did drop this assignment on you without prior guidance, the course ahead would be far to difficult, and you’d want to drop out from undue pressure. So I got some teaching aides to help you ease into harder tasks.”
 
Oliver blinked up at me, quizzically, and murmured “Di-Did you practice this before hand?” I ignored this question, it wasn’t relevant to the course.
 
I reached into the gift box, where my brother’s uniform had been stored, and reached for the bottom where I had hidden a couple of extra tools that will help us through this exercise.
 
I pulled out some lube and an ‘anal training kit’ —basically butt-plugs of increasing sizes— and asked him if he’d prefer my finger or the kit.
 
Considering how his eyes lit up seeing the toys, I wasn’t surprised when he said he prefer my dexterity over the plug, so I tossed aside the package, and placed the bottle of lube beside him on the bed; the toys will see their use another day, on who? I can’t be certain.
 
“Well then, let’s get these pants off you then. They only hinder further learning.” I unbuckled his belt, and grabbed his zipper with my teeth, a defined ‘bzzt’, loudly highlighted itself as I pulled it down, like a pen dropping on a tiled floor during a test. I pulled his pants down with his boxers, and saw his cock spring forward, flinging just a small dollop of his precum onto my chin. I wanted to suck it right there, but not losing sight of my task, I settled for cleaning up his head, and getting a solid lick on his frenulum, before returning my focus to his removing his trousers.
 
I’d thought I could get his jeans off myself, but I started to struggle, as I hit his feet and had to awkwardly ask for help, kinda killing the sexy, educational, vibe I was going for. “Uh… could you like just... kick a little bit?”
 
“Oh, sure… no prob.” He gave me the assistance needed, but couldn’t help himself for a smart observation at our scenario “Funny, how we put on these clothes just to take them off. It’s kinda unnecessary isn’t it to dress up for sex if you think about...”
 
“Stop talking, its part of the fun, stop killing the mood.” I gave him a death stare that got him to suck in his lips, like he’d just tasted a lemon.
 
“Sorry sorry... it’s who I am. I’ll try to just go with the flow. I’m loving every moment so far.” I appreciate the compliance from him; I didn’t need any more distractions.
 
“Thank you, Ollie. Good kohai!~” I saw his hard-on spring up when he heard me, It beckoned for me like a finger that curled. Damn this bottom energy, if I wasn’t so committed to topping today, I’d relent to it’s tease.
 
But proceeding forth, I poured some lube onto my digit, and rubbed his it into his entrance, being thorough to make sure it was nice and coated, so that his first time was a smooth experience; he gets on my nerves sometimes, but I’d never knowingly hurt him.
 
I lube up my index a bit more and tell him to, “Take a deep breath in and relax”, as I begin to insert my pointer into his ring, provoking the cutest mewl from him.
 
I slowly press my finger inside him until I can’t go further, and I let him know the next step is to basically “poke around until I feel like I can, comfortably, insert a second finger.”. I was met with an innocent nod as he lay back down with my prods. I hear his slow breathes as his cock strains with every thrust, and I observe his twitches and moans as I work the digit in. I blush intensely at his enjoyment, and wonder what he could possibly be thinking right now; probably about the dick he’s about to take, but that’s obvious.
 
I let him know the second digit is coming, and add my middle finger to the mix. I hear him blow out air at it’s entrance, and breathe a bit harder as I continue my work.
 
“Does it feel good?” I ask him out of curiosity.
 
A stuttering groan of “I-it fe-els -a-amazing” is uttered as he returns to focusing on his breathing.
 
I feel comfortable to continue forward and curl my finger inside of him, causing him to throw his head back with an audible moan.
 
“Oh” I curl my finger again, getting a similar reaction, and I giggle at my discovery “I think I found your prostate!” I do it a couple more times holding back my laugh, and stop when I see his balls clench just before he’s about to cum, so I freeze instantly.
 
“Oh oh! Not yet Ollie. Your senior still needs to get her cock in you. You can’t cum until I get my feel.” I’ve stopped moving, but kept my fingers inside him, the warmth around them feels nice. I can’t wait to warm my dick inside; the anticipation has me straining, as I think about it.
 
“Ollie you gotta tell me what it feels like to have your prostate played with. Futanari don’t have one, so I’ve always been curious.” His attempted burbles to answer my question, tell me I’m not going to get a coherent response anytime soon. So I spread my fingers apart inside him, just to make sure he’s really been opened up, and remove them with one last shudder from my little brother; I considered adding a third, but I’d honestly be giving myself to much credit if I did; sizeable, but not that big.
 
I get up and pull down my sodden panties, my cock drooling for it’s next course, eager to pounce. It lifts my skirt and hides under its brush, a one-eyed beast with it’s eye on it’s prey. I get between his calves that fall over the edge of the bed, and lift his legs over his head, feeling my shaft probe at his entry. His pre leaks down his belly and soaks into his sweater; not to go off-topic, but that’s shit's going to be a bitch to clean later.
 
“You can back out now. 2I’m not forcing anything upon you.” I give him one final chance to turn around before my worm bores his hole, but he is not deterred.
 
“I want to feel it senpai… I want you to teach me what it means to be a good kohai.” He looks up at me with a hazy expression, not eager, but curious, not necessarily lustful, but certainly wanton.
 
I’m glad he stayed committed to the bit, cause it gave me that extra push to thrust in, getting a girly moan from both of us. I started to cycle my hips in and out of him, being deliberate and slow not to hurt him, but I guess even that was still to much for him, as he softly begged me to pull out, after a couple of dozen successive pumps, and without hesitation, I did, slowly leaving his exit, letting him catch his breath as he softly gasped for air.
 
We were both breathing heavily in exhaustion, and I saw that tears had rolled down his eyes from what I assumed was pain. I couldn’t feel anything but emotional, and quickly apologized for the perceived injury that I might’ve caused him.
He gasped deeply before managing an airy cry of “I’m sorry, I’m sorry... it was just to much at first… let me… just let me…” I interrupted his pleas and kissed him softly.
 
“It’s okay if your not ready, don’t apologize. If you want to try again some other time we can, and if you don’t want to, we don’t have too.” I kissed his tears away, and felt bad. I tried hard to make sure this wouldn’t happen, but I still failed to make it easy. I was heartbroken, a bad senpai, and a bad older sister.
 
But, he grabbed my hand and kissed it. “You can insert it again, Chloe” His expression was one that was gentle and certain, but I had to confirm.
 
“Are you sure? It seemed like it was a bit much for you.” I looked at him with serious concern, I wanted this to go smoothly for the both of us, I didn’t want him to feel like he needed to do this for me.
 
“You just had to break the seal, I think... I'm sure now it’ll feel much better for both of us.” A glowing smile melted my heart. I gave him a more intense kiss, and placed my plug at his outlet.
 
I stared at him waiting for his go ahead, and he gave me a gentle nod of approval. So I thrust into him, and was relieved to hear a “God, yes!” from my intrusion, instead of another plea to stop. I started up the motions again, rolling my hips inside of him, creating wet slapping sounds as our bodies collided together. I used his legs as anchorage, as I started to pick up the pace. His insides were amazing, the heat of his oven, and it’s tightness, felt unreal around my cock. As I pierced his maw with my spear, I groaned into every thrust.
 
For his first time he took my dick quite well. His moans were that of a bard’s song, encouraging me with the motivation to keep going. His sweater became drenched with pre and sweat, his leaking cock flung clear droplets down onto his wardrobe, some even hitting his face; If he was more lucid he might’ve been mad, but he was clearly seeing stars in space.
 
I decided to break the duet of our moans and insert some dirty talk in the mix “Fuck, you like that don’t you? Tutor’s cock teaching you anal for the first time. Do you think you can handle harder material or you ready to bow out now?” My groans were guttural and animalistic, I was starting to think with my cock over my head.
 
My horny fire was fueled by Oliver’s begging request for me to go “Harder! Please I want you to go harder! I’m ready for you to go harder! Please! Pleaseeee!” At this point his voice had raised an octave. His usual 'manly' baritone was now that of a 'girly' falsetto. If he was still in pain, he’d been enjoying it to much to want to stop. I grinned, my brother had a demand, and I love to please.
 
“Alright, then wish granted.” I pulled out and directed him to get on all fours, making a spinning motion with my finger to tell him to face away from me.
 
He did as told and whimpered out a “You know, this position is a little more embarrassing when your actually doing it.” His flush face spoke essays, as he crawled to give me space on the bed.
 
“Don’t be embarrassed Ollie, you look cute. Perfect for your tutor to really demonstrate what ‘harder’ really means.” I got a handful of his soft cheeks, as I shuffled behind him. I heard him audibly swallow his anxiety, as I pumped my dick between his ass crack. I gave his cheek a firm tap with my rod, before I pushed into his pink star; I can see why he does it so often, it just felt right.
 
I heard him groan, and treated it as if it were a gun going off before a race, starting with a rabbit-like pace, much quicker than I had started with before. Almost instantly, his arms couldn’t support the weight that was being pounded into him, and his face fell into the mattress, causing his moans to be muffled, as I tried to ram him into the bed.
 
“God damn Ollie, if I didn’t love your dick so much, I’d never bottom again. Seeing you quiver under my thrusts has got me going fucking WILD!” I grabbed his hips and slammed into him, colliding with thundering echoes as my crotch met his cheeks. I could feel his prostate over my dick. The slight bump felt good with the texture of his insides, and compelled me to try and dig further into his rear. I was a mindless ape at this point, letting instinct guide me, and I was enjoying every bit of it.
 
I was, quite literally, drooling over his ass, and it’s soft, plumpness beckoned me to take my due. So, I slapped it red, without altering my pace, getting the wildest moan from him, as he pulled his head up out of from the plush bunk. It enthralled me, so I spanked, him again, and again, and again, until his hide was raw and red from my assault.
 
“Please, MoRe! Please, pleaSe, Pleease, Plesae!” He was a tornado of emotions, and a tsunami of desperation, and I wanted to make him worse.
 
I grabbed him by his hair and pulled him back to me so that he was now standing up on his knees, and I thrust up into him. “Hey Ollie, my cute kohai, answer me this…” I could hardly breathe between my pumps “… what does it mean… hah… when a doll like you…. Likes to get fucked rough… in their tight little boyhole?” His cock bounced up with my thrust. The weight of his ‘5 ft 10’, ‘195 lbs’ ass was ignored with my overwhelming lust; 5ft 2 in and 160 lbs and I’m still a monster, I was fueled by adrenaline, but acknowledge that I wouldn’t be able to do this if I wasn’t extremely horny.
 
He knew the answer, but struggled to say it as he spasmed over my shaft, so I slowed my pace for him, and attacked him with deliberate and heavy thrusts, so I could get him to jolt out a strained reply “It..t… means... I’m a s-slut!” I smirked, I was pleased, but not satisfied.
 
I stopped all motion, causing him to whimper in disappointment. He look down at me with puppy dog eyes, as if to ask ‘why’ I stopped, but I wasn’t going to let the role play end right there. I got all dolled up in this sexy, ‘e-girl’ make-up, dressed in this cute ‘school-girl’ outfit, and didn’t even take it off when I started to get hot and intense inside his ass, I mean, I'm sweating over this ass, literally. I committed to the bit, so I’m going to commit to the bit. If I were to just stop there and cum, well that would be a waste, wouldn’t it. So, in an upbeat tone I smiled at him.
 
“That’s correct, Oliver, but you didn’t say that with much enthusiasm. How is your tutor supposed to know that you will pass your test if you don’t answer her confidently?” I started to caress his skin. “So, try again and this time”, and I took a pause to thrust into him again, getting a solid grunt from us both, as his cock leaked like a faucet onto the sheets, “Make sure you say it with a lot of enthusiasm, or else we won’t get to end this session with a nice climax!” My eyes smiled with devious innocence, as I looked up at him, I held him close, I groped his chest and stomach, and played with his nipples.
 
He worked up his nerve, and gave me what I wanted. “A person who likes to be fucked in the ass raw and rough by their older sister” I interrupted him by churning his insides with my cock, getting a soft “fuck” from him, before I told him to “continue” with a smile in my eyes.
 
He breathed and did just that “a-and beg for more when she stops is mostly certainly a ‘slut’.” His breath was ragged, and he continued. “Senpai, I’m your bottom, slut, bitch! So, please let’s end this lesson and reach our climax together.” He didn’t look into my eyes, but I knew he was pleading with his face, as he stared up to the ceiling, with untamed hair over his vision.
 
Oh absolutely this is what I wanted, in fact, he gave me more than what I asked for, oh-so much more! Oliver is honestly such a sweetheart! Fulfilling his older sister's most degenerate desires! So, without further hesitation, let's finish the act and just fill that stomach of his.
 
“That correct, I’m glad you cooperated, your such a good kohai, you really learned a lot today.” I stroked his leg and rewarded him by massaging his cock, collecting some strands of precum in my hand, and tasting and savoring the nectar that I found, oh-so, sweet. “A is for anal, after all, and I think you’ve earned that grade with a plus, for sure.”
 
And I tossed him down, off of my thighs, onto the bed. He was prone on the mattress, and I pounced on top of him, and pierced his rear, as I held him down with my weight. Immediately, I hit my stride, and had no intention of stopping again. I’m so thankful we bought a new mattress, because with how hard I was spiking down into him, it would certainly get us another noise complaint, as I tried my best to hammer my brother through our bed.
 
It wasn’t much longer until we were both on our edge, and with one last, ample thrust, I grabbed and pulled his hair back, and bit my lip, coating his inside with my pearly seed, as he ruined our sheets with a painted portrait of our love. He didn’t moan, it was more like a guttural howl, before he collapsed onto the mattress from pure exhaustion.
 
I filled his gut with my jizz, pumping a few more ropes into him, before I pulled out, my climax beginning to fall. We were connected by stray strands of seed on my exit, a sight I had wished, I had captured on my phone, because I’d surely get off to it later, but alas and ‘all good things’, and our stringy, white cum bond was severed, when I fell down on top of my bro’s beautiful back.
 
I cuddled into his warm sweater and patted his head. “You did so good for me, lil bro…” I kissed his recovering face, messy hair covering his eyes and glasses, as he softly breathed in his euphoria.
 
It’s kinda embarrassing to mention this, but I licked at his cheek like a dog and bit it softly. I admit it’s a bit odd to do, but it’s because I love him that I do it, and selfishly, it’s my way of marking him as mine. Even in this frazzled state he’s the light of my life, and I’d never give that up for anything.
 
But, after giving him sometime to recover, I eventually ask him “So, how’d you like it your first time?” Eager in my curiosity to his experience, but also to see how well I performed.
 
All he could pant was “Amazing… it was heavenly and awesome!” before he turned to me and snuggled up into my blouse. I held his head close to my bosom, and ran a finger through his soft, curls; hopefully I didn’t damage anything, I'd gone a bit more berserk then I intended, too.
 
I looked down at him, and cooed “You know, I could get used to being on top for you more often, after that experience.”
 
He hugged me closer and whispered “Please do…” into my chest, tickling me a bit with his voice.
 
I giggled and pulled him up into a kiss, before resuming our snuggling.
 

 
We rested together for a warm ‘half-hour’, before he broke our silence by hesitantly asking “So...Um… am I a good boy, sis?
 
I squished his cheeks and spoke to him, in much the same tone as a doting dog owner would “Absolutely, your my precious, precious, little brother.”
 
He laughed softly and asked me another question “...c-could you say it…uh could you say it again?”
 
...Say what?… I asked puzzled?
 
...say that I’m a good kohai...
 
I looked directly into his wavering, hazel eyes, and with a motherly tone I whispered. “Oliver, your the best kohai.” Which made his face a beautiful shade of pink, as I felt his member start to peak back up in interest, gently poking at my soft sleeper, in hopes to wake her up.
 
Then it dawned on me. ‘oh fuck, were both bottoms!’
 
“Hey, hey mister don’t expect me to top all the time, now. I still need that fat dick inside me. You can’t just turncoat like that.” I sat up on my side and pointed at him, accusatorially. I am not an exclusive top, quite the opposite really, and I wouldn’t let him make me one.
 
“Don’t know if I can, sis. I think you made me see a new light, You might be ‘giving’ from now on and I will happily receive.” He sat up with me, a grin crossed on his face, as he adjusted his frames with a flashing gleam.
 
I’m not going to let this day backfire on me! It was supposed to be perfect for him, but it wasn't supposed to be this perfect!
 
“You can only bottom if you beat me in a game of rock, paper, scissors!” I had him pressed now, he knows I never lose at ‘RPS’, I know him too well. He’s a flowchart of rock first, into scissors second, and I can always tell when he tries to mix it up. I expected him to blindly accept the challenge, like he usually does, but he played it smart and met me with an even dumber response.
 
“How does that make sense? Do bottom’s look like winners? The winner should top! That’s how the Romans would decide! That’s how the vikings would decide! It’s only right!” What utter nonsense was he spewing?!?
 
“The winner shouldn’t be punished for winning, dumb ass! That defeats the point of winning!” I raise my hands in disbelief, before crossing them in agitation.
 
“Alright then, 1 v 1 me for bottom then. Game of choice is 'Street Fighter 3 TS'. Winner gets to decide their position from now on.” He crossed his arms and stared intensely toward me, but I would not accept his terms.
 
“I don’t play ‘boomer’ fighting games, nimrod. You know that! How about you see me in ‘Melty’ or ‘Skullgirls’!” I’d accept a duel with the sticks, but only for a game I know.
 
“I’m out of practice for both, so I refuse, but that doesn’t matter, anyways. You should be top because you’re better at it! You’re far more suited to play the role of ‘ass-pounder’ than I’d ever be.” He tries to appeal to my ego, but I won’t be flattered.
 
“Thank you, I’m glad you enjoyed it, but I beg to differ, by virtue of you having the bigger dick, you should top. That’s the rules, that’s how it’s always been! It’s tradition.” I counter with logical reasoning, I’d hope he didn’t have a retort, but of course, I was met again with opposition.
 
“Oh yeah, well I think tradition is shitty reasoning, peer pressure from dead idiots, I’ll pass on that, sis. Also aren’t you the one who believes that dumb rules should not be respected. Well I think, dick discrimination should not be respected. ‘I have to top, because I’ve the bigger cock?’ appeals to outdated penis-roles that society expects of us. They should be abolished and ignored, in favor of allowing those with gifts such as mine to enjoy the backseat for once.” He puts a hand over his chest like he just made the most coherent and well comprehensive thesis on why people of his massive endowments should be allowed to sub; What a joke.
 
What can I say, I’m fucking baffled, I was flash banged by this dimwit’s stupidity. “I can’t believe I’m in love with a moron… and did you not just appeal to tradition to get out of rock, paper, scissors?!?” I stutter out still trying to process… anything! anything at all of what's happening here.
 
“And I can’t believe I’m in love with someone who would so OPEN and BRAZENLY discriminate against those who were born with larger packages. I didn’t choose to have a big dick, a big dick chose me. We live in the verdant country of ‘Virgin Fields’, sis, a land where men are free to choose their own destiny! My destiny, I hear you ask? To take incestuous, futanari dick on the daily, regardless of the marvelous donger I’ve been given.” I heard the cry of an eagle over head, his stupidity was warping reality.
 
I was getting steamed, so I just let lose the bulls, and started an unintelligible shouting match that was stalemated, but perpetuated between us two; no real common ground was found among our words.
 
I guess, we were still siblings at the end of the day. So, after some more yelling, and a brief wrestling fit, that I struggled to win, with all my might, but no avail. We agreed that he gets to bottom every 'odd' day, and I get to every 'even'. An agreement that ultimately gives me the short end of the stick, but... not really cause, I mean, getting to nut in his ass really isn’t that bad, it’s really a no-lose scenario.
 
We’ll it’s a shame either way, because in our sibling quarrel, I forgot about his last surprise, the most expensive one that lay at the bottom of the larger box. Damn, I guess that ring shall see some use some other day. I'll try to make it special.