Your Principal, Mr. Latimer

The window rolls down to reveal the wide, bald head of your Principal, Mr. Latimer, nicknamed "Kingpin" both for his appearance and his attitude. You pray he doesn't recognize you.

"You look lost, little girl. Would you like a 'ride'?" He leers at you, his eyes practically drooling over your exposed flesh. You decide your best bet is to give him what he wants and lean into his torrid teen fantasy.

"Thanks, mister. It's awful spooky around here. I got kicked out of home and I am trying to earn some money for a hotel room for the night. Maybe we could help each other out?" You lean over his passenger window as you lay out your pitch in a sultry sing-song tone. You notice him checking out your flat chest and puffy pink nipples as he peeks under your bra, and he hangs on every word from your shiny, red lips.

"I...I think we can arrange something. I'm always glad to help a child in need." He opens the door for you and you slide in, realizing for the first time how imposing a figure he cuts. The kids call him "kingpin" because his wide, stocky figure and bald head, but whether it's fat or muscle, it would be enough to crush you like a bug if he wanted. You wonder why that thought makes your clitty throb, and you push your tutu down so he doesn't get a peek. He starts driving, seemingly very familiar with the neighborhood. He eventually pulls into an abandoned lot and turns off the engine. He puts his hand on your thigh, perilously close to your clitty. "So...how much help do you need? And how much help can you offer in return?"

You want to shoot for the moon and ask for $1000, but you remember what you're wearing and where he picked you up. You decided you are going to have to play the numbers game. "Well, mister, if you were really helpful and gave me $100 I could help you with anything your big heart desires. Or for $50, I could suck the cum out of your cock so hard it will make your eyes cross." You place your hand on his crotch and feel his cock swell, not as long as Daddy's but it feels so fat your jaw is already aching. You start stroking it and planting soft kisses on "kingpin's" stubbly chin, hoping to close the deal.

"Nnngg Fine, but you better be willing to work for this!" He slips a hundred dollar bill in your bra and pulls your mouth into his. His lips crush painfully against yours and his slug like tongue practically chokes you. You just suck on it like you would his cock, sliding your tongue slickly across it and relaxing your throat to let him fuck it.

You moan whorishly and he grunts appreciatively. His hand slides over to your bare ass and squeezes it painfully. His fat finger finds your lubed hole and starts exploring you. You whimper around his tongue before breaking the kiss and freeing his cock. "Please, mister, please can I suck it?"

"I...uhm...yes...please do." You smile as you see how flustered you have him. You can tell "kingpin" is used to paying for it and used to jaded whores faking **** out moans of pleasure, but he actually believes you are a horny little slut that would suck his cock for free if you didn't have to make some money. Probably because you really ARE a horny little slut and you are bobbing on his cock like it was your **** of choice, like you'd pay him to let you suck it. Luckily for you, he doesn't know how true that is. "Whoa...slow down. I want to get at that sweet ass of yours. And from the way I feel it squeezing down on my fingers, I know I'm not the only one!"

You pull off his cock with a PLOP and chirp "Yessir, Principal Latimer." The moment the words are out of your mouth, you realize your mistake. Unfortunately, so does he. He turns on the overhead light and pulls your face close. You see a look of recognition that turns to disgust. He reaches underneath your tattered tutu and grabs your tiny clit, it throbs in his heavy hand, seemingly oblivious to the danger you're in.

"I know you! You're that wimpy little brat always trying to get my star athletes in trouble. No school spirit...and a sissy runaway to boot. Why I have half a mind to..." your tremble before him, your eyes go wet, and before you know it, he has you pinned to the passenger door, collapsing on top of you, kissing you harder and hungrier than when he thought you were jailbait. "You should have SLURP told me who you were! I would have KISS paid more!" You yelp softly into his mouth and gasp for air as his weight threatens to crush you. He finally breaks the kiss before breaking every bone in your body.

"Need more room...outside...on the hood...going to fuck you so hard...show you how I deal with slutty sissy snitches." He's breathing hard and ranting. As scared as you are of being seen by someone, you're much more terrified of his raw strength and lustful rage. You scamper out of the car and lie back on the hood. You want him to see how scared you are, how humiliated you are to be discovered and exposed, and how much it turns you on.

"Please, Kingpin, show me who's boss...punish me..." you lift your legs over your head so he can see your plump, parted cheeks...your glistening, puckering hole...your hard drooling clit...and your flushed, feminine face...visibly aching with need. He is practically hyperventilating as he tosses your legs over his shoulder and pushes his xxl wide cockhead against your cunt.

"Gonna show you...PANT...show you what naughty PANT sissy sluts get! Show you PANT all!" Principal Latimer clearly has unresolved anger issues, but right you are only too glad to let him take them out on your tight pussy. Your Daddy is wide and so big, but this fat boy prick is filling you so full you feel like it's the first time again. Tears well up in your eyes and you feel the heat building up inside you. The hurt making the inevitable sissygasm seem all the sweeter.

"Oh Prinicpal...PANT I...I...respect your authortiteeeEEEEeEeee!" You are panting too now, not to mention painting your stomach with sticky sissy squirts. The rush of endorphins and adrenaline drown out the pain and the serotonin flooding you following your sissygasm makes you feel surprisingly romantic towards your pent up principal. You run your hands up his torso, surprised to find despite his frame, he is almost solid muscle underneath a layer of soft cushion. You find yourself pulling him on top of you, breathlessly kissing him as he pounds another savage sissygasm out of you.

"Learn NNH your NNG lesson!" He grunts and thrusts and his cock swells impossibly wider before filling your heated hungry hole with his creamy cum. You can practically feel it sizzle as he softens inside you and you slowly, dreamily kiss him as if you didn't think he was a lame loser...and with his tongue in your mouth and cock in your cunt, he actually feels like a winner. Finally he composes himself.

"Well...that was better than expected. I am at a loss for words. Since when did my laziest, whiniest student become the hardest working, horniest whore I ever fucked?" You give him a sanitized version of events that still leave you as a cock hungry sissy needing to earn another $900, but don't out you as an incestuous Daddy and sissy Mommy fucker. When he hears how much you need, you are surprised to hear him offer help.

"That's a pretty penny. You won't earn that on this block. Honestly I normally don't pay anything near that, but I could smell a hunger on you I just had to taste. But I could call some fellow faculty members with similar proclivities. You could earn the rest easily there. Or I could drop you uptown where the clients are more high dollar, but you would stand out like a sore asshole."

You weigh your options. Fucking the principal had been humiliating, degrading, and hotter than you had ever imagined it could be. More of that might be fun, but you increase the risk of exposing your sissy secret with every faculty member you fuck. On the other hand, maybe you could find a Richard Gere to make you his Pretty Sissy, or at least fuck you on top of a nicer car. Still, you would be a lot more conspicuous there...