A Clockwork Green Ch. 05- Transgender & Crossdressers

"So the guys in blue..."

"Hav-er-SHAM!! YEEES!!"

I frown and stare down at the... the knoll? Field. Whatever it's called. Clearly, one of the guys in blue just did something awesome because Charlotte is going bananas, but I can't figure out what. I never seem to know where to look. Every time the crowd erupts, I'm watching the other ball and nothing spectacular is happening.

"Haversham is your team?"

"Yes." She doesn't look at me, though I can hear the irritation in her voice. "And they're not just my team... they're my boys."

A huge crowd to my right explodes in cheer, but Charlotte is nonplussed. I try to look down to see what the commotion was about, but the ball is being reset and I can't tell who scored or where.

"And those guys who just yelled, they're..."

"Wickits fans! Look at their colors!" None of the four teams on the field have the dark green and red combo that crowd is wearing. When I look back at her she frowns, frustration written all over her face. "Those assholes are wearing the home colors, but the team is in their away colors to-COME THE FUCK ON, REF!! Shit! SHIIIIIIIT! What the hell is that cheap-ass shit call?! That wasn't hoarding!"

"'Ey! Pipe down over there, you Haver-lovin'-"

"FUCK YOU, YOU LITTLE BITCH!! Just because YOUR boys are down five points..."

I frown back and forth, gently tugging at Charlotte's surcoat. "Char, come on. It's only a game-"

Charlotte rounds on me, and I flinch involuntarily. "Only a game? ONLY A GAME?! This is BOARDS, little girl! It AIN'T just a GAME. It's THE game!" I've never seen Charlotte act so aggressively... with such masculinity. Even when she was Tony.

***

"Nooooo," Charlotte says, feebly trying to keep her cup away from the bartender. "Already drunk..."

"C'moooon," I say. "Look how little there is left in the bottle! That isn't worth saving!"

"Yoooou!" She points vaguely in my direction. "You drink it."

"Awww, don't be like that. So Haverford los-"

"Havershaaaaaam..."

"Haversham lost, but it's not the end of the world. Besides, I couldn't. I'm already waaay too drunk."

"You don't... don't look drunk," Charlotte says, blearily.

"Oh yeah. Trashed." I wobble on my stool and smile lazily. "See?" Charlotte nods and stops trying to play keep away with her cup. The tender fills it again with a dubious look. "Don't worry buddy. I'm gonna make sure she gets home ok."

***

"HaverSHAAAM! HaverSHAAAAAM!! Go Knights o'the... Hey, why are we gooin' through the... park?"

"Shortcut," I say, keeping a hand on her elbow as we pass through the wrought iron gate.

She fumbles her words for a few seconds and, having forgotten her place, starts the fight song over for about the tenth time tonight. "O' there is a team from HaverSHAM! Those men so great and proud..."

Gas lamps light the way down the concrete walk, but after rounding the a few corners, I lead Charlotte off the path and through the low grass.

"...drink in times of championshi...Mackenzie, I doooon't think this is a shortcuuuuut. We live oooover-"

"Of course it is, Cherry. Trust me." She giggles a little every time I use her pet name, and that distraction is enough to override her superior sense of direction.

We pass underneath a few trees and enter a clearing. A small pond sits still, with the heaviest of the fog settled above it. The Moon is barely visible as a hazy silver cloud. Charlotte takes a few steps forward to steady herself against a park bench and stargazes. "It's beauuuuutiful out here, Sweetness."

"It certainly is," I respond, running a hand up her thigh. Charlotte gasps as my fingers pass underneath her skirt, but just as she tries to turn around, I give her a light push between the shoulderblades. She would have tumbled over the bench entirely if not for my hand steadying her leg.

"WhooooooOOooOa, Mackenzie, what are you-" Charlotte cuts off in another gasp as I slide her skirt up over her waist. "What... What... What..." Charlotte's hands search for purchase on the bench seat, but the light layer of dew is enough to foil her inebriated attempts.

"I got to thinking," I say, as my hand runs farther and farther up her thigh, teasing her lips through the thin cloth. Her cheeks flush with embarrassment at being exposed, but she doesn't cry out. I rip her panties apart in the middle and she groans drunkenly. My fingers rub up and down her slit, leaving the realm of silence behind as she instinctively begins to grind against my fingers despite her protests. "First of all, you owe me, Cherry. That was four hours of my life in that deafening arena." Charlotte flushes a deep red. "Secondly, I thought this might be an appropriate setting to try something a little more public than a changing room, or an empty balcony."

"Mackenzie, this is too exposed! I couldn't! P-p-please!" Her words ring hollow even as she says them, and her final 'please' takes on a completely different tone as two of my fingers enter her pussy.

She lifts her head and tries to look around. The light fog has reduced the nearest houses to regularly spaced lights, but the fact that they are visible at all is shows how close they are. How easily they could see us. See me. Bear witness. It's intoxicating. I withdraw my fingers, but a hand on the small of her back keeps her bent over. I kick at her left foot, knocking it free from the ground, and Charlotte settles just a little lower, in a slightly wider stance. I slide my wet fingers in and out of her lips for another second before pulling them back and delivering a cupped-hand slap to her cunt. Her whole body jolts, and she gasps as I push three fingers back into her pussy, far less gracefully than they had entered the first time.

"Mackenzie! Please! We're going to get caught!"

"Isn't that what makes it fun?" She groans as I yank my fingers out again and drag my thumb over her clit. My hard-earned calluses ensure it's more of a rub than a caress, but she whimpers all the same. "Plus, don't you think you deserve to be caught? To be punished?"

'Yes," Charlotte says hesitantly. Another slap directly over her fuckhole, louder by an order of magnitude now that she's sloppy wet. "Yes! Punish me!" I jam the angry head of my prick up against her asshole, and she lets out another choked cry. "Yes!"

"Louder."

"Yes," Charlotte cries, although not half as hard as the cry she follows with as I enter her as forcefully, and as quickly, as I ever have. Her echoes have echoes. She frantically looks left and right. I grab one of her hands, and bend it back behind her. The twist keeps her bent forward, keeps her in place. In more ways than one. I bite my lip and grin. I grab a fistful of her jacket for leverage. Slowly, I push her forward until her thighs touch the wood of the bench, my fat prick nearly retreating entirely from her, but a strong jerk pulls her back and fills her again. A short cry escapes her lips before she manages to clamp down and quiet herself

"I can keep going slow like this, Cherry," I growl, "but that's not what you want, is it?"

"No," she said, louder than I would have thought. "Use me!" Another sharp jerk, taking her from tip to hip with a sharp cry. "Yes! Fuck me!"

"Louder."

"Fuck me like you mean it!" Her eyes pinch shut. "YES," she cries. My thrusts gain in intensity, forcing air out of her diaphragm with a strangled exclamation attached to each push. "YES, YES, YES, YES!"

I roughly jerk her up to a 45º angle, and push her against the bench. Now each thrust of that swollen cock of mine impacts heavily on her prostate, and she's lost the ability to make words with her sounds. I can't stop myself from muttering "fuck, fuck, fuck" under my breath.

Charlotte's formless cries rise higher and higher in pitch, and just when I think the peak of her orgasm is coming, I switch my rhythm entirely. Instead of a deep thrust from end to end, I begin a vaguely cyclical thrust, keeping that angry cockhead pressed hard against her prostate. Over her shoulder, I see thick ropes of cum burst forth and sail through the air before splashing into the pond, the ripples finally breaking the stillness.

Charlotte's knees go weak and buckle, but I pull her backwards and keep her upright, partly with my hands and partly with my fabulous fleshpole.

"Don't think this makes us even yet," I whisper.

***

Charlotte pulls down the hem of her skirt for fourth time in as many blocks as we walk. Her cheeks look like they might never lose their heat, and she anxiously looks over her shoulder again. All the while she wears nervous smile and licks her lips.

"Don't worry, Cherry. No one is following us."

"Are you ssssure?" Her heavy buzz hasn't subsided in the least.

"Of course I'm...Oh wait!" Suddenly, I grab her elbow and drag her roughly into an alley. Charlotte nearly rolls her ankle as she stumbles behind me.

"Did... did you hear someone?" Charlotte peeks her head to the side, fearfully glancing a hair down the street. I carefully drop down my pants and slip right behind her.

"On your knees." Charlotte spins almost too quickly. I grab her shoulders to steady her, and then gently lower her the rest of the way. My heavy tool hangs thick in front of her. "Time to finish the job," I say.

She stares goggle-eyed. I don't think she realized that I didn't finish in the park. Her hand tightens around the base as one of my hands tightens in her hair. Nothing beats that first lick; hesitant, tentative, and dripping with saliva. The fresh taste of her used asshole puts weight in her eyelids. She bathes my head, and it swells in fits and spurts. Her fingertips are pushed farther and farther away from each other as I approach critical mass. I lift it up, pull her in closer, and let it rest against her forehead. I wrap my other hand around my sack, force them down, and she opens her mouth wide like a good little girl. My hand clenches in her curls, and I push both balls in. Her cheeks swell, mirroring the widening of her eyes, but her tongue...

By the Gods, her tongue...

I unfold my hand, and she greedily sucks the remainder of my sack into her mouth. My cock obscures half her face, but the half I can see is more than enough. I pull her closer, practically smashing her face into my crotch. A drop of precum falls onto her forehead above her right eye, and I can't stop myself from giggling. Her tongue rolls and swirls, pressing them gently against the roof of her mouth. My head, my real head, wants to float away. It's exquisite...

Her eyes close, and she loses herself in the worship. One of her hands is holding her skirt up to her stomach while the other strokes her own cock lovingly. I bite my lip, watching her take care of herself so tenderly.

I'm in no hurry, so I let her continue her gentle ministrations. She switches back and forth, lavishing attention on one jewel at a time. My fingers find their own way around my engorged shaft, and the slightest bit of squeezing brings another drop of precum peeking out the tip. I drop this one above her left eye. Charlotte is unaware, lost in the love she's making with my scrotum. Another stroke, another drip... and I delicately paint a smile just above her eyebrows.

Wet slurping sounds echo in the alley as she sucks air noisily around my boys, and I can't take the buildup anymore. I need her mouth. Nothing else will do. I push her head back roughly. She releases my balls reluctantly, with a sharp sucking sound. Her mouth, hanging open. Her eyes, heavy lidded. I practically whimper as she slowly raises them to me.

"Fuck my face, Sweetness," she gasps. "Use me like a toy."

The swollen tip of my cock slips between her lips, there to stay for a few minutes. My fingers clench so tightly in her hair, I wonder if I've ever actually made a fist before. I redefine fist as I drag her mouth down my flesh road. Her lips stretch tight over the knot at the end, causing her eyes to flutter, but once past she finds my gaze again. Her head rocks up and back, flexing at the shoulders while I guide her. My feet take root on the pavement; I am a monolith. I am firm, and unmoving. I am hard.

I push her out to the head, and she blows deep breaths through flared nostrils. A few seconds respite, and back down again, farther this time. My head pushes into the narrow spaces in the back of her mouth, threatening her throat. Closer each time. So close. Each time. I shove down on her head, and she hunches, and the path into her throat becomes a possibility.

Her eyes clamp shut when I finally pull in. She tries to open them again on the trip back, but I pull her throat around my head again. Harder. Harder. She stretches, molding to fit me. To suit my needs. Her nose brushes the tiny chevron of orange pubic hair, and I cannot resist groaning. No pushing back, just pushing in now. She squawks, fighting for air, but there is no resistance to my guidance. Her moist lips slide the last half of an inch, and I relent.

"<gasp> YES <gasp>," she cries, her face a deeper shade of red than even her pet namesake. "Use me!" She fights for, and gets her breath back, faster than I had anticipated, but I will not stand in the way of her pleasuring me. Not tonight. I pull her past the knot, pulling inwards until I feel the pinch. My fingers flex and regrip, and this time, I pin her in place. The last two inches, the tightest two inches, the first two inches of her throat, I fuck. Her eyes leak tears in a near constant stream as I ravage her suckhole. My face twists almost angrily, eyes boring into her skull, but her only response is a sloppy, drooling "<glalp><glalp><glalp><glalp>"

"You need that, don't you?"