Author's Note

Notice: I'm inexperience at writing clop so... this is practice for my other series Stepping in. Any advice on how to better write would be great. It's probably terrible so read at your own discretion.

Twilight Sparkle (1)

You are anon.

You came to Equestria a few years ago and have taken up residence in a small house by the everfree forest. The warm sunlight from your open window is shining in your face. "Gah, fucking sunbutt and her damn sun..." you mutter as you roll over and pull the blanket over your shoulder. Sleep starts to take you over before you hear three knocks from your front door.

Damn it fluttershy, when will she learn that you don't want to date her. Her daily fetish guess' are irritating you to the point where you can't sleep in past 8 anymore. letting out a long suffering sigh you get up and walk down your hallway to the front door. Opening it as she is about to knock again you see her recoil and give you a sheepish look.

"um... hi anon." fluttershy squeaks out as you lean against your door frame. She looks up your body as she takes in your appearance. Wearing only PJ pants you roll your eyes as you snap your fingers in front of her eyes as she ogles you bare chest.

"Earth to shy, whats your guess today?" you say.

"... uh um... is. is your fetish blue balling?" she says as she reaches her hoof out toward your genitals.

"no shy." you say as you slap her hoof away. "when will you stop with the fetish guessing? I'm not interested." she gives you a dejected look as she looks down and blushes.

"oh. ok... I'll get it right one day." she says as she turns around and walks back down the path to her cottage.

Your day goes the same way it always does. Shit, shower, shave. eat a healthy breakfast that you wish could be changed. The ponies would have a field day if they ever caught you with anything but fish to eat considering almost all the animals have some sort of sapience. finishing your forced healthy breakfast you do the dishes so they don't pile up and get ready for your daily friendship lessons with twilight sparkle.

~~~~

Walking up to the Friendship castle you wave at the guards posted at the front door. They know you by now and never give you trouble seeing as you've been taking the "lessons" with twilight for over a year now. You enter the overly large crystal tree and open the door of the 'Classroom'. "Yo Twi, whats cracka-lackin."

Twilight lets out a sigh and gives you an annoyed look. "Anon, your late again."

Frowning you reply "If you would just set our lessons at a realistic time I wouldn't be late. 7 A.M. is earlier than any school I ever went to." shaking her head she just points to a desk.

"7 A.M. is a perfectly reasonable time to be up and ready to learn." she replies as she takes her place in front of her chalk board.

~~~~

Something is off about twilight today as she goes over her boring lessons. her hair is up in a bun and she is wearing a form fitting black dress that stops just above her hind leg knees. Its almost kinda sexy. ANON what the FUCK are you thinking? sure you have been here over 2 years now but are you seriously thinking about twilight like that? I mean her round ass is jus- Jesus anon quit your shit you'll just have to visit Ms. Rosy Palm later to take care of this problem your having.

Twilight turns around and smacks your table with a ruler. "Anon we're you paying attention?" snapping out of your mind you stare at Twilight who has an angry glare.

"uh... yes?" you say not wanting her to get in one of her moods.

"Then you won't mind a pop quiz will you?" she levitates a paper before you face.

"of course not Twilight. what were we studying again?" you say while trying not to imagine her using that ruler to- Get it together man only a few more hours and you can go home and take care of this problem.

Shaking her head, Twilight scowls at you. "I can't believe you Anon, every day its the same thing. You come here and I try to teach you the importance of friendship and you can't even stay focused for 10 minutes before I catch you off in dream land! You used to be so attentive in the first few months but I just can't get across to you anymore! What will it take to get the lessons across to you Anon tell me how I'm supposed to teach you." she slouches in defeat looking at the ground.

You feel like shit. "Cmon Twi. I can learn its just I'm more of a hands on learner you used to learn your friendship lessons with your friends right? why can't I just go out and hang out with friends and learn that way? It worked for you." you reply petting her behind the ear.

Twilight lets out a soft moan as she pushes into your hand. All the ponies never resist the ear rub. "may... maybe that would work." she says as she pulls away shaking her hair out of the bun and standing up blushing slightly. "Alright then lets go out and do this!" she says enthusiastically pulling the dress off over her head with her magic. While ponies are always naked seeing a pony undress makes your earlier thoughts about Twilight come back in full force.

She turns around to trot off to the door as you watch her tail flick back and forth as you catch an eye full of what makes Twilight a mare. Shivering in delight and rearranging yourself so your half chub isn't noticeable you get up from the too small desk (which twilight refused to change to your size), you stumble your way catching up with Twilight.

~~~~

"Anon." Twilight says looking up at you with hatred in her eyes. "Yes Twilight?" you reply looking down at her with a false smile. "Why in the name of Celestia did you think telling Mrs. Cake she had a 'rockin booty' in front of Mr. Cake was a good way to make friends?" she didn't word it like a question more like a statement.

"Uh you said giving Ponies compliments was a good way to make them like you and that's a compliment where I come from." hiding a smirk you look back up and start walking away from Sugar Cube Corner.

Twilight hovers in front of your face with an angry glare. "You know how to make good first impressions anon why did you have to do that? You know better than to make suggestive comments on married mares, not to mention not doing so on a first impression, Anon." she pokes you in the chest. Rolling your eyes you bat away her hoof.

"Twilight, I know how to make friends I'm friends with lots of ponies. Rainbow Dash and I read Daring do together, Applejack and I grow crops together, Octavia likes to come over and play with me when I play piano. Need I go on?"

Twilight scoffs. "You know what I mean anon you can't just go around antagonizing ponies or no one will want to be your friend anymore!" she says as she tries to keep up with you.

"Twilight. I haven't needed friendship lessons with the ponies for a long time. I know how to be sociable I just like pushing your buttons." you say as you decide to stop in your tracks and look at her in the eye. "You're too cute when you get mad. The only reason I don't do it more is cause you can blast me to the moon and no one would bat an eye cause your a princess. I love the faces you ponies make when you guys get all flustered."

Twilight's wings ruffle and her face blushes deep red. "OOHhhh anon..." she stares at you then drops her head down losing her ability to fight.

"I know you don't need friendship lessons anymore anon... Its just... when you showed signs of not needing my lessons anymore i got... I got scared okay?" she says dejectedly as she turns away. You see a few tears wetting the ground in front of you. Confused you decide to walk around to face her seeing her tears streaming down her cheeks.

"why are you scared Twi? You know your my best friend here in Ponyville." you state kneeling and giving her a hug.

"Once you're done with your lessons you don't need me anymore and then you wont come around anymore, then you'll see me less and less and before you know it you won't come around to see me and I lose you." she blurts out and then cries into your shoulder. Shocked by her outburst you can only smile as you hug her a little closer. You know Twilight by now and once she gets something in her mind its hard to get out.

"Twilight Sparkle, You should know me better than that. I would never abandon a friend. You've helped me far to much to ever repay and I couldn't let our friendship drift like that. Why didn't you say something earlier? we can always find out other things to do together. We could always go out and have lunch together and talk about our days, or have some tea and read a few books together like I do with dash? There are plenty of other things we could do together." you say rubbing the back of her neck and gently stroking down her back to her wings.

"But I like teaching you things, and since you can't learn magic and you already know the magic of friendship what else could I show you?" she replies as she pulls back and you look into those big beautiful purple orbs. Stroking her muzzle and holding it in your hand you reply.

"Anything else your interested in. Teach me about the constellations or something I know your telescope hasn't seen use in a while and I don't know about your worlds stars yet." you say pulling that right out of your ass not even knowing if she has used it recently.

Smiling Twilight's eyes become bigger somehow and she smiles largely. "Really? I didn't know you were interested in Astronomy Anon!" You aren't. "Ohmygosh you should come over tonight! There are so many Constellations going to be visible tonight because of the new moon! There are so many possibilities for learning! Orion will be out in full force and Scorpios will be brilliant because of Taurus-Mph" you silence Twilight with a finger smiling like an idiot. "Show and tell later and since we'll probably be up pretty late we should probably go take a long nap so we can stay up tonight." you reply as Twilight's eyes sparkle at you.

"Its a date!" Twilight says jumping and flying away quickly towards the castle.

Is it a date?

~~~~

You tried to sleep when you got home but you couldn't. Was Twilight serious when she said it was a date? I mean sure she is pretty cute for a pony (Not that you'll every admit it) but you couldn't stop thinking of her in that school teacher outfit she was wearing earlier. She never wore it before and all of this seems kinda out of the blue. Before today you never really looked at Twilight with the idea of being a girlfriend but the more you think about her like that the more you seem to think that you and her would be great together. You're a big goofball and like to poker her admittedly easy buttons and she is a huge nerd just like you. Before you two started the friendship lessons you just kinda hung out together and read in the library before she became the princess of friendship (which didn't really make sense to you but whatever). Then the lessons started and she just became more annoying than anything.

Now that you have stewed here long enough to finally start thinking of ponies as more possible romantic interests the more your mind drifts back to the days where you and Twilight would sit together in silence only to read and be in close proximity to each other. Before you got your own house after Tirek fucked up the library (Luckily you were getting groceries at the time) you did your best to help Twi organize her library and took over making food for your friends.

Rolling over in your bed you look at the single suit Rarity made for you that one time you went to the grand galloping gala. You hated that thing and the gala but you could never throw it away because Rarity worked so hard on it. It was a nice suit, Black slacks dark red coat and a matching tie with her cutie mark in a deep blue that contrasted the red quite nicely. Maybe you should wear it to your 'date' tonight. I mean that's what you do on those right? dress up and show up with wine or something. Maybe flowers. Shit you don't really know the first thing about pony dating customs you thought you'd never want to actually date one so you skipped over those books.

Deciding you should er on the side of caution you decided to just say fuck it and get all dressed up and show up with a nice big bottle of wine from berry, she still owes you from when she pants-ed you in a pinkie party and everyone saw your white boxers with the red hearts all over them. Some ponies still call you lover boy.

~~~~

its almost 9 P.M. and you picked up that bottle of wine and got all dressed up. Some towns ponies were wondering why you were all dressed up but you just said you were going star gazing with a friend. While not false you never told anyone just who you were going with they all smirked and wished you luck though so that's nice.

Walking up to the castle you see the guards with their same stoic expressionless mugs. "yo dudes whats cracka-lackin?" you say as you lean up against the door staring at the guard on the right. Behind you the other guard kicks the door open making you fall on the floor almost dropping the wine. "Hey man this shits expensive." you grumble as you pick yourself up as you dust off your suit turning around to see twilight come around the corner. Her eyes widen in shock as she looks at you up and down and gulps and blushes a deep crimson. While you smile at her you notice she is naked obviously not having dressed up at all. Your smile falters and becomes a frown as your face heats up. She didn't mean a date as you thought she meant.

Turning around in embarrassment you quickly rush off back home. God damn it anon you are so stupid! Why did you think that she meant a real date? No one but Fluttershy is into that inter-species crap and twilight would never be into you like that. You're her best friend not her love interest!

"Anon wait!" you hear Twilight gallop after you but you decide to run quickly back home trying to hold back some tears. Loneliness is all you'll know on the romantic front. Until you eventually give in to fluttershy obviously. But your still a few years from her breaking you down she is just too weird with her constant guess' of your fetishs. Reaching your home you slam your door shut and slide down it sitting on your rear in front of the door.

~~~~

Opening the bottle of wine in the kitchen you decide that you might as well try and forget tonight and pretend it never happened tomorrow as you pour yourself a glass and sip it. You finish the glass in record speed and are about to pour another when you hear three knocks on your front door. God damn it fluttershy a second time today? You're really starting to lose your patience. Stomping over to the front door you rip it open "If your here for another fetish guess you can shove... it..." you drop your glass of wine as you realize its not fluttershy but Twilight in a sparkling purple dress with a shade so deep its almost black at the bottom. Her hair is up in a braid and hanging off to the side while her bangs are swept gently to the right. she's breath taking.

"Tw-Twilight?" you sputter like a retard. "wow." you say blushing just as hard as she is, considering her face is as red as a tomato your blushing pretty damn hard.

"Anon." she says gently as she shuffles back and forth on her hooves. "ca-can I come in?" using her magic she fixes the broken glass on the floor and shoots the wine off the front porch into the bushes before placing the glass back in your hand.

"O-Of course Twi" you say holding the door open watching her trot in and she nervously twirls her dress a bit.

"Do you like it?" she says smiling at you her blush only slightly receding.

"Yeah. I, I thought you meant date tonight like Date date, but I guess i was-Mph" Twilight shushes you with a hoof.

"I didn't but that doesn't mean I don't want it to be one." She says while she looks deep into your eyes. Her purple orbs look hopeful as she removes her hoof. "C-can we make it a real date? I've never been on one." she mumbles out while shuffling her hooves and ruffling her wings.

"Sure Twi. To be honest I. I never really thought about you like that before earlier when you called it a date and the more I thought about it the more I liked the idea. I mean we used to gel so well together before you became a Princess and I miss the days when we would just... you know be together in the same room and do nothing but read and be near each other." you say as you move to the couch and sit down.

Twilight follows you levitating the wine and another glass over to the coffee table setting it down. "I never really thought about you like that till the gala about a year ago anon. I mean seeing you all dressed up and taking an interest in the nobles even though I knew you didn't like them. Standing by me while I dealt with all the snobs and helping me curb some of the more... forward ones. It made me want to... To just..." she pours herself a glass and decides to trot over to the window and teleport her telescope near the window.

You get up and pull the couch closer to the window and sit back down pulling Twilight into a hug from behind she lets out an adorable squeak. "Anon what are you doing?" she cries as she wiggles against you.

"Hugging my Best friend." you say as she calms down a bit. You can't see it but she is frowning. "why didn't you ever tell me?" you said as you start to gently rub her furry chest.

"I didn't want to push you away, I know fluttershy is constantly trying to win you over and you just seemed so against dating a... a pony." she whimpers and lets her head sag and rub against your hand.

"I have to admit before today I couldn't really ever see myself with a pony but. You just... You aren't like any other pony Twilight. You're special to me. You were there for me before anyone else and I'll never forget your kindness." you say kissing her cheek from behind. Her face immediately flushes and she tries to hide it by drinking her whole glass of wine.

"Do you really want to learn about astronomy or were you just trying to be nice?" she says as she regains her composure.

"Honestly? I never cared about all that junk I just like spending time with you Twilight." you say as you hug her closer. "I'm sure you could find some way to make it interesting. I like history more so maybe you can tell me the stories behind the formations?" you say as you pet her mane as she shudders slightly when you rub betwixt her ears.

"O-Of course anon. I love spending time with you too." she says as she leans back farther into your chest.

~~~~

"And that's why Orion's belt had three stars on his belt not four." Twilight says as you look up to the stars.

"Wow Twi I never knew Astronomy was so interesting." You say as you pull away from the telescope and look at Twilight giving her a large smile.

"Hehehehe..." Twilight stifles a laugh as she covers her muzzle with a hoof and looks away.

"What? what are you laughing at?" you say as you give her a frown. She simply levitates a mirror in front of you and you see a black circle around your eye. "oh you're going to get it!" you say as you leap towards her just as she 'eeps!' and teleport's away behind the couch laughing in a full giggle fit. Recovering quickly you vault over the couch and snatch her up before she could teleport and wrap your hand around her horn. "ah ah ah..." you say as she squeaks and then gives a small moan as your hand slips up a bit on her horn.

"Uh did I do something wrong?" you say as you realize just what kind of compromising position your in with be hind legs splayed out and your pelvis up against her and your hand resting on her horn. "horns are... a sensitive..." she mumbles out the last part and you realize just what your doing.

"oh shit I'm sorry Twi I didn't mean t-MMMMpphhhmmmmmm" you start to sputter but she quickly wraps her front hooves around your neck and pulls you into a kiss. letting go of her horn you start to kiss her back as her tongue gently probes your lips. Opening your mouth you let her tongue enter your mouth as your hand quickly finds its place behind her head. Your fingers feel like their running through silk while your tongue fights Twilight's for dominance easily overtaking her inexperience.

Breaking the kiss and pulling up for air you look down into her dreamy half lidded purple orbs. She is smiling softly as she caresses your cheek with a hoof. "I love you." she says as your face burns bright red.

"Uh... I... um." you stutter out and she looks ashamed and teleport's out from under you and beside you.

"sorry! sorry. I just... I've waited so long to say that and I know its probably too soon for you to say it back I just have thought it for so long." she rubs the back of her head as you turn and sit on your carpet looking at her. She is shifting from left to right on her hooves and blushing furiously while finding her telescope particularly interesting right now. "You don't have to say it back I just wanted to let you know and Its just waiting to say it for over a year makes it hard, and when we finally kissed I couldn't help myself i......" she trails off as you gently put your hand under her chin and pull her face to yours.

"I love you too Twilight. I'm sorry it took me so long to realize it." You say as you pull her into another kiss. She moans gently into your mouth as you seek permission to her mouth this time, gently running your tongue over her soft velvety lips. She opens her mouth as you pull her whole body closer before gently picking her up and hold her into your standing form. Holding her by her rump you gently squeeze her round flank.

"Anon~" she croons into your neck while gently biting down on your shoulder. You walk over to the couch before you gently lay her down on it and gently lay on top of her resuming your previous kiss. When you pull away a small string of saliva hangs between your lips and hers and she smiles at you with a big goofy grin.

"Do you want... want to get more comfortable?" she says as she slowly starts pulling at your tux coat with magic. nodding you start pulling her dress up from the bottom pulling it over her head. when you lay eyes on her naked form you realize just how sexy of a mare she is. Her curved flanks her taught and lean barrel. her perfectly shaped legs sculpted by the gods just for you. The tuft of hair on her chest that just slightly longer than the rest of her fur and her sparkling purple eyes. Her braided hair that is just a little messy and has a few strands out of place while she looks at your in nervous anticipation to see your naked form.

You pull the jacket of your tux off and slowly unbutton your dress shirt before pulling it apart bearing your chest and the patch of hair covering it. Her gaze turns lustful as she runs a hoof down your pecks to your happy trail below your belly button. Gently pulling on the clasp that holds your pants then undoing the belt you let your pants drop as you step out of your slacks pulling your socks off with each foot as you kick your pants and socks away leaving your white boxers that have hearts on them. Twilight's blush covers almost her whole head as she looks at the tent in your pants and she rubs your slightly muscular legs (Which you've gotten from all your walks everywhere). "wow anon... You've really taken care of yourself since you've come to ponyville." She says as she pulls you with magic right back on top of her lavender form.

"You're looking better too, don't think I haven't notice your tighter barrel and those beautiful legs of yours." you say as you run your hand up her hind leg, making her shiver in delight.

"Anon~" she sighs as she pulls your face further down back into a passionate kiss. Her tongue pushes against your lips as her hind legs wrap themselves around your waist pulling your barely covered dick right against her sex. Twilight's warm mare juice covers your boxers and makes you even harder.

"I've dream't of this day for so long Anon." Twilight moans into your ear after breaking your kiss.

"Let me make up for time lost then." You whisper in her ear before nipping at it and biting softly down on the tip of her ear. She lets out a moan of delight as her hooves unwrap themselves from your neck and you start kissing your way down her cheek. Stopping at her neck you bit down a bit harder letting your canines push against her soft skin underneath her soft fur.

"Ooohhh Anon~" she croons as she rubs the back of your neck before gently pushing you farther down. Your tongue traces a wavy line down her chest and then stops at her barrel. Using both your hands you gently rub them across the joints of her wings pushing into them and making her moan even harder. You eventually find the points that make her react the most and focus on them as you kiss even farther down her barrel stopping at her teats.

"Anon~ please~" Twilight begs as her pushes you farther down with her front hooves while you chuckle. Letting go with your right hand you bring it down and gently massage her right teat and you suckle at her left nipple. Gently biting it and rolling your tongue around it. Twilight gasps and moans louder "How are you so good at this? I thought you weren't interested in mares..."

"I wasn't, I was interested in A mare." you put an emphases on A and she smiles a big goofy smile and gasps again when you gently lick all the way up her winking marehood.

"I've also had sex with human females before and they seemed to like the same stuff. You know besides the wings and horn I kinda know what I'm doing." you say as you start to prob the entrance of her vagina with your tongue. Groping her teat a bit harder and pushing her wing joint you quickly try to catch her winking clitoris before sighing and bringing your left hand down and around her glorious flank. Running your finger up and down her soaking vulva you gather enough juices to lubricate your finger easily before gently pushing farther in. Twilight lets out a loud moan and arches her back and her clitoris winks out in time for you to latch onto it and give it a strong tug.

"AAAAAHHHHHHHHhhhhhhhhhhhhh~" Twilight cries out in ecstasy, As the muscles in her marehood clamp down on your single digit. Small amounts of fluid drips out around your finger and you let go of her clit to lap up her precious marecum. Once her high from cuming goes down you look up to see Twilight in a state of pure bliss. Kissing your way back up not taking your time in the least. You reach her lips as you kiss her as she tries to focus back on what you were doing.

Pulling your boxers down and kicking them off you line yourself up with Twilight's Soft lips gently rubbing up and down to lubricate yourself. "Anon, please... please take me. Make me your mare." Twilight sighs and kisses your deeply. Her tongue pushes past your lips again and she easily dominates yours while your lost in the feeling of the heat of her pussy lips. Its so warm and slick that you actually slip out of her tight hole twice before she grunts and envelops your dick in magic holds your stead against her entrance.

"Make it quick. Then hold still so I can adjust. I... I'm still a Virgin." Twilight says with slight apprehension and nervousness in her voice.

"Anything for you... My love." you say as she looks into your eyes with pure love. Then hurt as you quickly hilt yourself inside her as she opens her mouth in an 'o' and silently screams. You hold yourself hilted in her tight marehood as it grips your dick like a vice grip. It massages you to the point where you almost cum instantly inside the tight warm walls as they ripple and squeeze around your shaft.

As almost a full minute passes twilight finally nods her head as you take it as a sign to start moving. You pull out gently and slowly as she lets out a loud moan, followed by a gasp as your head is the only thing remaining her soft velvety folds. You can feel them pulling you back in begging you to make her full again. So you gently start pushing back in. One hand holds her right wing pushing softly into a wing joint and the other hand holds her muzzle as you finally hilt yourself again your pubic bone pushed right into hers as your cock twitches inside of her. "Fuck Twilight." you gasp out. "You're so fucking tight." you moan as you pull out again.

"Faster Anon. I need you." Twilight shudders as she can feel your cock twitch deep within her pressing right up against her cervix. You pull yourself out quicker and start fucking her at a steady pace. As your hips meet in there is a nice loud slap that makes you smile. Twilight is yours now. She is your mare and nothing can rip you two apart. So you decide to pick up the pace as she starts to whimper. At first you think you might be hurting her before she cums around you shaft and her pussy grips your harder then ever before and ripples up and down your shaft with her velvet walls. You have to stop yourself mid thrust because you cant push any farther in without hurting her. It almost sends you over the edge and if you had been hilted you probably would have but this gives you an opportunity to make this even better.

After Twilight's orgasm you pull her up before she can regain her senses and pull her onto your lap sitting her upright and facing you. You lower yourself off the couch enough to where you can thrust into her easily and start pushing up into her right against her G-spot. Her cries of ecstasy makes you smirk as you let your left hand wander up a wing while you right hand goes right for her horn. She immediately screams as she has another orgasm from all the stimulation and your fully hilted this time but you push your own orgasm back down as you start to fuck her through hers. With how much marecum there is on your dick it shouldn't hurt her now and you start pounding into her.

After a few minutes you feel your balls tighten up, Twilight had cum two more times and you have to tell her before you blow your load. "Twilight.... I'm... I'm Close." you say as she is riding you.

"please... Cum inside me... Cum inside me and make me your mare." Twilight all but screams as you start pushing yourself to the limit. Your Hips are pistoning in her as fast as you can. You can't take it anymore and the pleasure rushes up your cock.

"I'm cumming!" you groan as the first spurt of your spunk coats her cervix with a thick glob of cum. Spurt after spurt coats the rest of her rippling vagina as Twilight orgasms on your throbbing dick.

Finally after glob after sticky glob of cum is released inside of Twilight she finally falls against your chest her head buried into you. "Oh fuck Twi. That was so good." you gently stroke her mane. Twilight's soft breathing reaches your pounding ears. Your heart rate slows over the next few minutes and you realize that Twilight has actually fallen asleep on you. Chuckling softly you lay back on your couch letting her sleep on top of you as you pull the blanket out from under the coffee table that you keep there for long nights of drinking. Throwing it over you both you gently stroke her back as you let yourself be taken to dream land.

Today was a good day.