https://ponerpics.org/images/6081753

>"It's not crossdressing!  It's cosplay!!!"
>The young stallion blushes furiously as he shouts at you.
"If you say so, princess."
>He's hardly the strangest pony you've seen at TwiliCon.
>But he is definitely the cutest, and his cosplay definitely does something for Little Anon.
"You pull off the look really well, you know.  I bet you've been covered in mares admiring you all day... and stallions too, for that matter."
>"W-well thanks, I guess.  It w-was really hard to get this cosplay just right!"  He stammers.
>"Most ponies d-don't know as much about Princess Twilight as I do, heh."  He ends with a nervous, somewhat feminine giggle.
"I'm anon, nice to meet you.... ?"
>"Star T-Tracker."
>Weird name for an earth pony.
>You close the gap and begin to gently pat his head.
"Well Star Tracker, I can make a real princess out of you, if you want."
>He blushes a little harder, his pupils shrink down, and he starts visibly sweating as he tries to form a reply.
>"Ehehe, I don't, uh, I mean, erm, you... would?"  You see a glimmer of hope in his eyes.
>You scratch one of his ears, almost causing him to let out a moan, but he stops himself.  Poor guy must be starved of contact.  Or maybe the ear scritchies are just that nice for ponies?
>You lean down and whisper.
"Where are your Royal Quarters, Princess Star?"
>With a gulp, Star Tracker mutters "Uhm, on the third floor, room number... I'll just show you."
>Grinning, you squat down and brace yourself, then pick him up.
>"WhaaaaaaAAGHH!?"
>He's much heavier than he looks, and more plush than you'd expect.  He must have some plump flanks underneath that dress.  W-wew.
>Somehow you manage to flip him over in your arms so he's looking up at you.
>"Uhh, eheheh?"
>He has no words, just embarrassment and anticipation.  And rightly so, as his equipment is now exposed to you and anypony who happens to look.
>And there are plenty who are looking.
>You begin to walk towards the stair well.

>Holy hell, ponies are heavy.
>After carrying one up three flights of stairs you're huffing and puffing.  Maybe you're not as /fit/ as you thought.
>Star Tracker's nerves have apparently lightened a bit from watching you struggle, and he's just chuckling at you now.
>"Now go to the fourth door on the right."
>You follow his directions and use the key he fished out of a hidden pocket to open the door.
>It's a standard room at the Poniott Hotel.  You stride over to the bed and place him down on it, then breathe a sigh of relief.
>"What are we gonna-" You shut his snoot with two fingers before he can complete that stupid quote.
>You lie down next to Star and pull him in to kiss his muzzle.  A gentle one, to start.
>Then you kiss him again, and again.  He quickly starts to get into it.
>Before long, you two are making out like the horny bastards you are.
>You invade his mouth with your tongue and feel up the soft insides of his muzzle.
>He actually tastes quite nice, in a masculine sort of way.
>And smells nice too, he must have put on some perfume with the dress...
>But much as you enjoy it, Star's constant moaning is making you impatient.
>You break away from him.
"Do you want to be a good princess, Star?"
>He excitedly nods at you as the blushing returns.
>You begin to disrobe as you command him "Sit on the floor right here, facing the bed."
>He does so, biting his lip as he waits for you.
>Now that your clothes are off, you sit on the bed in front of him.
>Star looks at your member, now right in front of his snoot, with obvious trepidation, then gulps and place his front hooves on your thighs.
>You gently take the shoes off his hooves and then reach your hand over to rub his ear.
>Reassured, he sticks his tongue out, and drags it along your length, first up to the tip, then back down to your balls.
>The 'Princess' then starts to lick and suck on your sack while his hooves work your shaft.
>Then moves back up and carefully takes the tip into his mouth.
"Unf.  Now, suck on it a little, Princess."
>You see his cheeks deflate a little as he closes his eyes and begins to apply some suction.
>You grunt in satisfaction.  You only have your head in and the velvety softness is already amazing.
"Swirl your tongue around, like a good mare."
>As he does so, he also takes more of your length into his muzzle and bobs on it.
>He's even moaning and grunting as he sucks.  And he's so damn cute the whole time, with the crown and dress on.
>F-fuck.  No way can you last much longer.  You NEED to cum inside this colt.  Preferably in both ends
>Star pulls back off takes a breather.
>"Wow, it's really salty!  I've never, uh, d-done this before.  Not with a real one, anyway."
>Enough chit-chat.  You slap his snout with your cock and put it back in.
>You grab his head with both hands now and begin to thrust into him, deeper and deeper.  He doesn't seem to mind.
>"Glk-glk-mmf-nnnf-nnNNFF-GLK..." are the eloquent sounds coming from your cock-sock, erm, 'Princess'.
>Now you're on the very edge of blasting, but you stop and push him off your dick.
"Open your mouth wide and stick out your tongue for me."
>Star is so lustful now that he does so without hesitation and looks up at you with those big blue eyes.  All you need to do is thrust along his tongue a few final times...
"AAAGGHHH!"
>You shout as cum explodes from your cock, into his mouth and all over his tongue, more and more with each spurt.
>But you pull back and make sure to get plenty all over his snout and the rest of his face.  You even save a few ropes of jizz for his ears.
"Hahh, fuck."
>Now Star is lewdly covered in cum, providing a pleasant contrast to the deep red of his blushing cheeks.
>You didn't even know ponies could blush that hard.  The combination of shame, excitement, and abject horniness must be doing a real number on him.
>You work the last few drops out of your manhood onto his eager, waiting face.
"Now, Star, a good mare swallows~"
>He closes his mouth and gulps down all the cream you gave him.
"Good girl."
>You almost feel spent.
>But there's no way you or Little Anon are going to give up.  Star deserves to made into a REAL princess, pronto.  And the sight before you is impossibly lewd, only a faggot would stop now.
>But you do need a few moments of rest, so you lie back on the bed and motion for Star to get up next to you.

"What was that about never sucking a *real* cock before?"
>"Oh, it's because, um, I sucked a dildo, o-once, as a j-joke of course! hehe."
"You must have gotten lots of practice with that toy, Princess Star Tracker."
>"Uh, maybe?"  He's clearly not sure what you're getting at.
"Have you ever put anything in your ponut, Star?"
>His nerves come back and he stumbles over his words hopelessly.
>"Oh, ahahaha why would, I mean how, who, what kind of colt puts, you know, hahahaha-"
>You kiss the pony to calm him down.  He tastes like cum now.  Gay.
"It's okay, Star.  I won't fuck you silly like a mare in heat if you don't want me to."
>That might be a lie.  With a pony this cute you're not certain you could resist >raping him.  Hopefully it doesn't come to that.
>With a deep breath he starts over.  "Ok, um, I might have ridden the dildo, a f-few times... b-but only because I was imagining that it was Twilight!!"
>Twilight?  With a dick?  You smirk.  Of course, it's always the Twifags.  But even in Equestria, futafags are gay as fuck.
>But now you could feel a resurgence of energy... and of blood to your dick.  Time to give this pony what he deserves.  You get off the bed and pull Star over to the edge and roll him so he's on his back.
>His cute pink-and-blue mottled horse dick is rock hard and dripping with precum.  You realize that he's probably been horny since he first put the dress on, hours and hours ago.  He needs some relief.
>You crouch down and get close and personal with his rump.  It really is quite soft and plump, and feels lovely to grab and knead.
>And his rear, with his tail flowing down and the end of the dress flopped out of the way, is alluring, to say the least.
>You give the bottom of his balls a kiss, then move down to lick his dock hungrily.  The unexpected sensation causes Star to gasp.
>You take the bottle of lube conveniently placed on a nearby end table (presumably Star was going to make use of his dildo while here, but he won't need it anymore), and pour some onto the Princess's succulent ponut.
>You work the lube in with a thumb, while you send your other hand to feel up Star's flanks and legs.  Such a very, very soft pony...
>Taking your thumb out of him, you switch to your index finger, and stick it in all the way, then wriggle it around.
>"Mmm...This feels weird, anon"
>When you can feel he's all lubed up, you slide a second finger in, causing Star to whine and grunt.
>Now a third, and you use them to stretch his ponut wide.
>"Ohhhh, Tw-... er, nnnnf."
>He seems like he'll just be able to fit you, nice and snug.
>You stand up straight and pour a bunch more lube onto your member and then line up with Star's hole.
"Ready for your coronation, Star?"
>He bites his lip, hard, while nodding and making some kind of excited horse noise.
>You grab his legs at the thighs and push your hips forward.  The tip of your dick presses against his ponut, and slowly enters him.
>"Ahhhhh~"
>Star is watching it go in with a look of profound need on his face.  But you're not going to let him have it that easily.
>When the head of your dick is in, you stop and pull back out.
>"Anon...?!"
>You push into him again, going just a bit farther than last time.
"A Princess needs to be patient, you know.  And you should really ask nicely if you want something."
>"A-anon, stop teasing me!  Please?"
"Hmmm... I'm not convinced."
>You need to hear some more desperation in his voice before you give in.
>So you pull back out.
>Star whimpers.
>Slowly, you force your way into him again, deeper, then stop.
"What do you want, Star?  Say it!"
>"I- I want you to fuck me~!  Fuck me!  Please?!"
>Well that does it.  You drag your manhood back out, then put it allllll the way in him, until your balls slap against his dock.
>"Nnnnffff!" Star groans in delight at the feeling of fullness.  "Fuck your p-princess, servant!"
>He's getting feisty.  You decide to just grind against him while balls deep for a moment
>Then you grab him by his barrel and start to pound his ponut, firmly but not too fast.
>The room is filled with the lewd sounds of slapping, smacking, and Star Tracker's grunting.
>With each thrust, a bit more precum leaks out from him, onto the front part of his dress.
>And Star's grunts turn to gasps as you use him.
>But you need more!
>You grab his hind legs again, this time at the fetlocks, and push them down towards his barrel, as you bend over him.
>The change in angle causes Star to start whining in desperation for release.  His face contorts into a cute new face with each thrust.
>His front hooves are stretched at his sides, trying to grasp at the sheets on the bed.
>Reaching one hand up to hold his head, you bend a bit lower and lock him in a wet kiss.  He whines and moans into your mouth the whole time, making you harder than ever as you wreck his colt pussy.
>He wraps his hooves around you and digs them into your back.
>When you break the kiss (a long strand of saliva still hanging between you two), you run your hand through his messy mane and whisper:
"You can cum now, princess~"
>Your timing is perfect.  His eyes glaze over and then he shuts them and grits his teeth.
>"Ahnnnn, nnfff, Yes Twily!  TwiiiiiiiiAAAAAAAGGGGHHHHHHHH!!"  Star Tracker loses all control and screams out Twilight's name along with a stream of horse obscenities.
>You feel his dick throb between the two of you, and then feel the warmth of the ocean of cum that proceeds to pour forth.  Some of it even spurts all the way to Star's face, to mix with the remains of your own earlier layer.
>His insides spasm around you but you try to remain in control long enough to really milk his prostate.
>As his orgasm dies down, you give three last herculean thrusts into him, then release your own torrent of cum.
"FUCK, Star!"
>The rough thrusts force another few spurts from Star's balls even as you drain your own into him.
>You feel your cum drizzling back out, down your balls and legs, and you give the newly-minted Princess a long kiss as your balls finally empty.
>Pulling your dick out, you collapse into bed next to the dazed pony.

>Star's a complete mess: his face, neck, ears, chest, barrel, front legs, hind legs, dock, and tail are all stained with cum now.
>Not to mention the state of the dress.  You hope there's a spell or something to clean cum stains, otherwise his cosplay is completely ruined.
>Oh well, not your problem.  If he cared about that, he should have taken the dress off beforehand.
>"Uuuughhh... Anon," Star begins, "so, does this mean I'm a real princess now?"
>You think for a moment.
"No, not quite.  There's one more thing you need, but you need to get the dress off first."
>He seems concerned that there's more, but he shakily stands so that you can remove the clothing.
>When that's done, you make him lie back down on the bed, then you lie down next to him, and pull him in for cuddles.