Take it (up the ass) like a man!

It's just another in a day full of perverse paradoxes, but it seems like the manliest option is to get fucked up the ass by your biggest while dressed like a sissy slut. You can feel your brain straining to the point of snapping as you try to process the path to becoming Maddie's master and all the twisted turns you've taken so far as well as what you have to face next. Sure, it sounds pretty gay and girly to crossdress and take cock, but if the alternative is losing a slutty sex **** willing to fulfill your deepest, darkest fantasies, it would be gayer to not get fucked. "Alright, I'll do whatever it takes to make you my ****, but be ready for me to take out everything you put me through on your ass, slut!"

"Eeeeeeeee! Thank SLURP you! KISS Thank you! Thank SUCK you! I promise MMPH you WHIMPER won't regret it!" Maddie slides off your lap, leaving you straining in your panties and more determined than ever to prove your manliness. You follow Maddie to Brad's front door and wait on tenter hooks as she knocks loud and fast like she's here on a warrant check. Brad makes it to the door and his expression goes from annoyed, to intrigued, to disappointed. You are used to being jealous of his athletic build and aggressively handsome features, but now there's a certain curiosity added as well. You find yourself wondering if he is a better kisser than Officer Daddy, or how his cock compares, but you stop yourself short of checking out his package.

"Fuuuuuuck, Maggie! When you texted that you were bringing a virgin that's somehow sluttier than you, I thought it would be some hot college chick from one of your advanced learning classes! If I'm going to give you up as a ****, I'd think you could offer me a better trade. I mean, technically, little Elliot is a virgin. Sigh...oh well, come on in and we'll find out how slutty he is." Brad gives you an almost friendly smile as gou step inside in a daze, trying to figure out which part of his spiel pissed you off the most. Maybe it's his assumption that you are here to offer up your ass, and the fact that he's right only makes it more infuriating. Maybe it's the way he treats Maddie like she's property, and the fact that you want to do the same only makes it more maddening. If you had to pick just one, it would have to be that he doesn't even know his ****'s name!

"So, my **** says that you want to be her Master, and that you are willing to do, and I quote, 'absolutely anything, and I mean that in the most literal sense possible'. Me, I don't see it as a fair trade. I happen to like my ****, even if she is a little mouthy, is a little small for my tastes, and is way too fucking weird. Oh well, let's see what we're working with." Brad sits in an easy chair and motions for you to strip. You want to correct the misunderstanding that you are trading places with Maddie, but you find it hard to speak up with your heart pounding so hard in your head. This is the asshole that dubbed you all of your worst nicknames, and now he'll think he's been proven right. Still, you don't see any other option, so you begin to pull your shirt off.

"Stop stop stop! Christ, you really are a virgin. You are supposed to be seducing me, right? Do it slower. Make a show of it." Brad sighs and you blush, torn between wanting to impress him and telling him to get fucked. Maddie gives you an encouraging wink and blows you a kiss, and you imagine what she would do. You begin to sway slowly running your hands up and down your body and offering glimpses of your smooth stomach as you lift your shirt. You continue moving to an internal rythym you didn't even know you possessed, showing more and more skin as you sway, until you reveal your pink satin bra and the tops of your puffy nipples peeking out. "Ha! Called it!"

You feel yourself burning up...with rage at Brad taunting you for the countless time, shame at him being right...if only technically, and something growing in your belly that you'd rather not focus on. Instead, you use the heat to fuel your dance, slowly teasing your pants down to give quick looks at your creamy hips and pretty pink panties. You kick off your shoes and lift your leg high to slide off your socks, and Brad raises an eyebrow, apparently as surprised as you are by your flexibility. You turn with a flourish and drop to your knees to show off your ample ass, arching, bouncing, and twerking. You see Brad readjust himself out of the corner of your eye as you slither up serpentine out of your jeans and stand before him, blushing and boned and beaming with perverse pride.

"See? Ella is way sluttier than I was before I got my cherry popped and, not gonna lie, has a better ass too. The little cutie came from sucking her first cock! Imagine how in love she'll be with the first man that fucks the cum out of her. She'll never want to leave you." Maddie's words hit hard, but she softens them by stripping down to her skivvies. walking behind you, and sliding her small, supple hands all over your body and sucking on your nape and neck. Your gears are grinding as you realize that she is offering you as a permanent trade to earn her own freedom, but your ass is grinding against her groping grip making it hard to think straight. Maybe this is the best she can do against a brutish bully like Brad. Maybe it would be worth being his **** from time to time if you get to have Maddie when he's busy with his countless conquests.

"You know, for a so called sex ****, you sure do ask a lot of favors. Fuck it. Get her warmed up for me and we'll see if she's a keeper." Brad stays seated and sighs as if he's bored stiff, but judging by the bulge in his jeans, he's stiff but not bored. You turn to Maddie, searching her eyes for a clue to her conflicting stories. You want to believe that she wants you as badly as she says, but it's getting harder and harder to believe the more she emasculates and embarrasses you. Then she lowers her lashes and looks up at you with unbridled lust that just can't be fucked. She tilts her head slightly and pulls you into a passionate kiss that you trust more than Brad's lies.

You kiss her back, hungry and hard until hurts, lapping up her whimpers off her tongue and biting her bottom lip until it bleeds. Maddie moans into your mouth and slides her silk covered, sopping slit against your pantied prick. You have never felt so turned on...so sexy. In a twisted way, you've never felt more confident either. You have a stunning, smol sexpot ready to cum all over you, eagerly pushing her perky tits against your chest and pert ass into your hungry hands and surrendering sweetly to your lips and tongue. You feel her go limp and yielding and you sink down with her to the floor, a tangle of tongues and limbs writhing wetly entwined around each other. Whatever other deals and dares are going on behind your back, this feels real...this feels like love.

"Damn, girls, now you've got me wet!" Brad chuckles and you break the kiss reluctantly to see him naked, looking like a Greek god and lubing up his hard, footlong monster. You feel a moment of panic, but Maddie pulls you into another kiss and presses her moist mound up against your achingly hard cock. You lose yourself in her, ignoring Brad and doing your damndest to make Maddie melt into a puddle below you. She seems to have the same mission, groping your ass, kneading your doughy cheeks and sliding them up and down, sending sizzling sparks from your asshole up your spine. You are getting almost eager to feel something fill the growing, growling hunger inside you.

"Try not to fall too hard for me, Ella. I've got a lot of sluts to keep busy and I can't stand when they get clingy." Brad slides between your legs and lifts your ass up, and you are just about to tell him you will never fall for an asshole like him, but then he presses his fat prick into your tight hole and you lose your train of thought.

"WaiMMPH SHLLP SUCK MMM" You have second thoughts as he enters you. It feels like he's trying to fit a beer can inside you, stretching and searing with no thought to your comfort. The pain is indescribable, both physically and emotionally. You have hated Brad for almost all your life. His cruelty has done more to shape you than anyone's kindness. Lesser bullies took his talking points and aped his tactics, hangers on mocked you mercilessly and left you lonely and with low self esteem, even other losers ostracised you for fear of drawing a target on their back. He made you the weak, wanting wimp that was such easy prey to get turned on and turned out by a submissive siren. And now he's reshaping you literally, forcing his impossibly proportioned prick inside your ass until you can feel his balls pushing against yours.

Maddie is doing her damndest to distract you with what certainly feels like genuine affection and arousal, but suddenly you grow suspect. How would you recognize a forgery, having never felt the real thing? Maybe your dweeby degenerate has been playing you all along? If so, what can you do about it now? Should you just let events take their course, even if they are heading for a trainwreck? Or should you try to find a way to fight back, no matter how futile?