Blackmailing a Genderbent Old Rival and Mind-Breaking Her

I had the worst fucking luck with jobs. First job, my boss had been a sexual harasser - and a guy, at that. Second job, my boss blamed me for stealing from the till (which I didn't do). Third job, one of my coworkers was Reese.

Back in high school, Reese had been my perpetual bully. A jock type who got to do whatever he wanted because the school wanted to maintain their precious handball team. Even now that he was part of "the team," he was a total jackass to me all the time, calling me twerp, telling embarrassing stories from high school to the other guys, all kinds of shit like that. It honestly made me seriously consider quitting.

Two months into the horrible experience, though, I stumbled on Reese in the office bathroom - he hadn't locked the door. Or perhaps I should say, she hadn't locked the door. Because Reese was sporting a very hefty chest now, changing out breast wrappings to hide the new bust. On instinct, I took out my phone and started snapping pictures. Reese noticed me, but she was a deer in the headlights, gazing brainlessly at my phone with panic on her face. "Wh-wh-what are you doing here, twerp?" Her voice had lost some of its affected grit, now feminine and girlish because of her shock.

I don't know how I acted as fast as I did. I knew Reese had a pretty hot girlfriend (he wouldn't shut the fuck up about her and show us all her pictures), and I knew she hadn't always been a girl. In my head, I processed it in the second or two it took her to complain about my presence, and for me to take plenty of photos of her bare breasts. "I'll send these pictures to your girlfriend and all our coworkers, if you don't do what I want."

She hesitated just a moment, hand against her breasts, covering her nipples. She looked like she wanted to eviscerate me, but after a few long seconds, she spoke up. "Fine," she said. "What do you want?"

I hadn't actually planned for this moment, so I blurted out the first thing that came to mind. "I want you to dress in a maid uniform and cat ears." She frowned, and that made a feeling of sadism and revenge surge inside me. It was just some petty thing to make fun of her, get back at her a little bit for all she'd done back in high school, and she was resisting right now? Fuck her. "For a whole week. You take the week off work, work as a maid around my house, and I get to fuck you whenever I want," I said, just adding more and more shit on to teach her a lesson.

When she still seemed hesitant, I opened my mouth, fully planning to add something more to the pile. "I'll do it, I'll do it," she said, hurriedly, raising her hands up defensively, not wanting to get more punishment. It gave me a nice look at her tits.

"Good. Tell the boss you need the week off. I'll see you at my place." Her expression wasn't happy, but she nodded in acquiescence.

* * *

I honestly expected Reese to come to her senses and reject the deal I'd offered her, but no, she showed up at my place shortly after work got off, even got dressed in the maid outfit with the cute cat ears that I'd bought on my own way home. She was busty now - a real beauty, with short, dark hair and brilliant violet eyes, and a nice tan from all her long love of sports.

"When the week's up, that's it," she said, quietly wringing her gloved hands against the hem of her maid uniform. "You have to delete the pictures you took, and never bring this up, ever."

"Of course," I agreed, smiling at her. I knew Reese was a moron, but I never would have thought he was ignorant enough not to realize what was about to happen. I was going to fuck her until she fell in love with me - did she really not know that's how girls' sexuality worked? I mean, yeah, high school had taught us abstinence only, but she clearly had no idea that by the week's end, she'd be purring and begging for my cock. You'd think she would have picked it up somewhere, but, nope. My good luck, I guess. "Let's get started," I said, unbuttoning and unzipping my pants, just standing right in front of her as my hard cock popped out.

She flushed with embarrassment, staring at it. Her hand went to her mouth, almost chewing on her thumb as she held her fist there. It was a pretty sexy sight, the way her eyes seemed to zone in on my dick. She still wasn't sucking my dick, though, so I just put my hand on the top of her head and pushed her down.

She descended to her knees, and I slapped my dick up against her cheek without saying a single word, just enjoying seeing the slight smear of precum against her cheek. Her nose wrinkled at my scent, but she didn't actually complain - no, instead, she wound up sniffing at it again, as if surprised that it smelled nice. I swished it up across her features, rubbing her nose right into the crook of it, enjoying the look of her with her face practically buried in my groin, her breaths tickling my balls. She didn't fight back in the least, just let me do that to her.

I started rubbing my dick all along her face, getting extremely aroused to the sight of my old bully submissively taking it, letting my cocksweat splatter against her cheeks, my precum smear against her bare skin. I pressed my tip up against her nose, and she just let out a soft sigh, delighting in the scent of my thick precum as it thoroughly lodged itself in her brain.

Fuck. I'd heard guys whose gender got flipped had a hard time dealing with the way more intense libido of girls, but I really hadn't expected for her to be quite so eager. "Open up," I said, smacking my dick against her pretty lips, and obediently, her mouth opened wide, letting me just slide my length right in there. I could feel her tongue rub against the underside, flat and wet; extra saliva dribbled out past her lower lip, splashing onto her full tits as I sawed my way deep inside her. Her throat was an inviting, warm, wet hole, soon wrapped tight around my dick as I ground her nose right into my pubes.

Sexy as it was to see her respond this way to her new position in life, I did still harbor an urge for revenge, and seeing her brainlessly accepting my dick wasn't going to fully satisfy that. "Look at you now," I said, gripping the back of her head to hold her in place, my other hand reaching down for her tit. "You used to be the tough guy back in high school, the jock who got away with everything, but now you're just happily sucking on my cock, isn't that right?"

Her brain restarted to those words, a scowl forming on her features, but I held her down, choking her on my dick as she let out muffled noises around my dick. I couldn't make out any words, but I could tell she was pissed, so I squeezed her tit a little bit tighter. "You make a really sexy girl, with these big fat tits. It's like a tomboy born to be a slut, which, I guess you kind of are, aren't you? Just a cocksucking little maid, reborn to sexually serve your new master." All the while, I kept on choking her, enjoying as fury and impotent rage - accompanied, here and there, by spasmodic slaps of her hands against my thighs - slowly dwindled.

The throat's an erogenous zone for girls, after all, and my throbbing, pulsing dick was constantly rubbing against it, no doubt driving her wild as her nostrils flared and she was made to accept every single bit of her new treatment. Arousal was the first thing to replace it, her hips absently grinding against the air, little bucks of pleasure as wet sounds emanated from her throat. Her hands came to grip and squeeze my thighs instead of slapping at them, and soon enough, she came, spasming in ecstasy, eyes rolling up in pleasure as her whole body twitched like that.

Sexy as it was, the even sexier thing was watching her pass out, partway through said orgasm, not having quite realized she was being choked by my cock because of the brain-melting waves of pleasure. I pulled out of her mouth, let her collapse onto her back, and pushed up her maid uniform's skirt. I obviously hadn't included any panties, and fortunately, Reese had understood the implications of that fact, and was bottomless. She was shaved down there - I wondered if she'd shaved back when she was a boy? - and I just slammed my cock inside her, making her gurgle and spasm as she woke up. I could feel the resistance as I tore past her hymen, her eyeballs rolling around in their sockets, seeming to be unable to focus or identify much of anything at all.

"You used to call me gay, but look at you now, Reese. You're choking on your own spit like a horny bimbo while I fuck you," I told her, gripping her hips as I fucked away with relentless force, just pounding her right into the floor then and there. "You make a really cute girly-girl, you should grow your hair out," I told her, making her sputter, her cheeks burning with humiliation. "Huh? You don't like the thought of happily bouncing on Master's cock wearing nothing but a smile, your hair grown out, having become my little sex maid? That's strange, your cunt doesn't seem to agree with your brain on that point," I told her, pinching her clit as I said it, sending her over the edge and making her spasm and jerk in wild-eyed pleasure.

My hand slid around her throat, a tentative thing, just a reminder of who was in charge as I slipped beneath the cloth neckline of her dress. There was a plenty big tit window, and I decided to show my appreciation for it, leaning down to kiss at those breasts, grabbing the base with my teeth and yanking it down until I could see her dark areolas, her perky nipples straining up at the air. My free hand gently caressed her tit, while my cock slammed inside her again and again.

"You, little, twerp," Reese managed to get out, still holding onto her pride. It made my cock throb inside her. "I bet - b-b-bet, you think you're, so f-fucking, tough," she managed to dribble out. "You're, you can only, get, laid with, blackmail," she continued, swallowing some of the saliva that had built up in her mouth.

I pulled my mouth out of her bosom, smirking down at her as I kept going at her wet cunt. "If you hate it so much, how come your legs are wrapped around my hips?" I asked her, enjoying the look of shock, horror, surprise, and humiliation, as she realized that was exactly what she was doing. "But yes, we did just take each other's virginities, isn't it sweet? Isn't it so much better to be my personal sex maid, than my constant, asshole, work rival?"

As obvious as it was that she hated it, she couldn't really do much other than take my verbal abuse, though, because she came again, and I started choking her, fingers constricting around her throat to block her airways. Her eyes rolled up, and her legs locked even tighter around my waist, seemingly begging me to unload inside her needy, formerly-virginal cunt. I just enjoyed the sensation of her insides trying to wring an orgasm out of me, the tight muscles wrapping and massaging my whole length, making me quietly groan as all the feelings washed over me.

When she came down from her orgasm, I released my grip on her throat, hands instead grabbing both her tits and playing with them roughly as she desperately gasped for air, eyes wide. "You make such a perfect sex maid," I told her. "I really like your cat ears, too, they make me want to pet you an treat you nice. Too bad I remember what a prick you are," I added, with a nasty grin.

She didn't respond; my roughness with her tits was sending her into a fit of pleasure, as was my furious pace inside her cunt. The most she could get out was little gurgles, the occasional scarcely-coherent word: a "nuh" or a "muh," a "cock" or a "more," all mixing together in a delightful little noisy cacophony that accompanied the use of my new sexual outlet.

I came inside her, of course. A thick splatter of cum, sprayed right into that needy, freshly-made, just-for-me womb. This was a tight virgin's cunt, one that was pleading to be impregnated, and I was going to do exactly that. "You'll make a really hot mom," I told her, as I finished coming. Her eyes widened, and I could tell she was probably about to start trying to escape, so I decided to lie to her. "Oh, don't worry, I'm just teasing. I took the male pill before you came over, obviously."

It was a complete lie, but she accepted it, sagging down against the floor and letting me keep using her. I came inside her a good six times - and she had produced a thick puddle of lemon-lime scented juices from all her constant orgasms, by the time I pulled out of her, admiring the mess of a body that was laid out on the ground beneath me, skin still slick with sweat.

"Whew. That was exhausting," I told her, taking in a deep breath and then exhaling a moment later. "I'm going to bed. Since there's only the one bed, you're coming with me, Reese," I told her, taking hold of her wrist. She was out of it enough that she stumbled as she came to her feet, staggered as she walked after me, but didn't resist in the least, as I curled up behind her, wrapping my arms around her waist.

I didn't bother pulling up my pants, so she could feel my cock harden and soften again and again over the course of the night.

* * *

I made her suck me off that morning, enjoying the way she glared up at me. I gave her plenty of mean comments to keep up that furious furrowing of the brow, her nose crinkled in anger as I stated how great of a cocksucker she was, as I asked if she'd done it before, as I suggested she was a natural because, really, she was born to do this, wasn't she? If you thought about it, the only reason she even had a mouth was so that one day she could wind up in between my legs, the target of my long hatred, now relieved in her tight throat.

She didn't spit it out when I came all over the inside of her mouth, splattering her palate and tongue alike with a thick, sticky load of my cum. She just swilled and swallowed it like a good girl. I patted her head. "That was good. You're behaving well."

"Twerp, don't get weird about this," she half-snarled. "I just know you want me to swallow because unlike you, I'm not a virgin, and my actual girlfriend knows to swallow every last drop of my cum. Because I taught her to."

"Of course, of course," I said, heading into the shower and getting dressed. "Unlike you, I have a job besides sucking and fucking, so I'm going to just head out to work. You can clean up the house, you're dressed for it. Oh - wash up that outfit, it reeks of sweat and cum for some reason."

She scowled at me, but I could hear her sniff her clothes as I left her alone in the house. I was pretty damn sure she'd behave herself, and even as I kept getting hard at work - thinking of her pretty lips, her full tits, her nice scrumptious ass - I managed to wait, holding back until our working hours were done.

The moment I was back home, though, I was relieving all that pent up desire. I found her in the living room, chomping on some crackers as she watched television. She was, at least, in costume. I just grabbed the crackers from her and stuck my dick right in her face, slapping her cheeks with it as she tried to shift her head to get back to watching TV. "Hey, hey, you're a cocksucking whore now," I told her, with a smear of my precum against her nose. "You only get to watch TV when I don't want to use your mouth and throat for my personal pleasure." I gripped the back of her head, and she acquiesced to my control, letting me drag her down onto my cock, her throat swelling to accommodate my girth as I ground her cute little nose into my pubes.

"Ah, you really do look so great like that," I told her, as her cheeks swelled. I started to saw back and forth, rubbing my dick all over her palate and tongue, and I could hear the TV still playing. "You like sucking dick more than eating, don't you? That's why instead of eating those crackers, your pretty little lips are wrapped around my dick." I smiled cruelly down at her, sadism satiated by being able to treat her like this. I held her in my groin and sat down, and she actually seemed happy at that - she could watch the dumb action movie she was watching this way, even as her mouth, tongue, lips, and throat were all used as my personal masturbation aides.

It felt great, just conquering my old bully like this. Not what I would have thought my ultimate revenge against the guy would have been, but I certainly wasn't complaining. When I came, I made sure to do it in her mouth. "Just keep it there," I ordered. "You can watch this crap as long as it's still in your mouth. When you swallow, you're getting on your knees and slurping my dick down."

She managed to hold it in her mouth for a good five minutes before the saliva and cum finally started overflowing - rather than swallow, though, she let it dribble out over her chin and splatter onto her tits. I decided to let her get away with that, since she was just doing her best to follow her new master's commands, and stuck her in my lap to ride on my cock as her movie played.

I didn't pay any attention to it, though. By the time I was through with her, she wasn't able to pay attention to it either, just drooling and coming and spasming in my lap like the perfect little fuckslave she was becoming.

* * *

It was the fifth day of her new life as my personal sex maid that she finally broke. Oh, don't get me wrong, I groped her tits, fucked her mouth, and slammed into her cunt plenty. She took it all with a glare, seemingly counting down the days until she was finally free of this, never once realizing that the truth was, she'd never actually be free of this. I'd gotten home from work, made her lie down on her back on the bed, and pulled down her maid uniform so I could stick my dick in between her tits.

Seeing those gloved fingers pressing into the supple flesh of her tits while she glared hatefully up at me with violet eyes, scowling faintly, her lips pursed in restrained fury, was a hell of an erotic sight. Even better, though, was when she came in that position for the first time - no small thanks to my tweaking and teasing her nipples - and the dam finally burst, her mind melting mirroring the way that her juices spilled out onto the bed.

She sputtered as it hit her, her eyes widening in shock. Her lips opened wide, a perfect little o-shape, complete with white teeth and a sexy little tongue that slid out past her lips as her brain restarted. It flicked against the tip of my dick, beginning to hungrily lap at it, her fingers getting more forceful as she ground those fat tits of hers into my cock, the cute little mole pressing against my bare skin. I smiled down at her wickedly, running my fingers through her hair. "Look at you, Reese. You're happy now, aren't you? Being my personal sexual serving maid is so much nicer than antagonizing me, isn't it?"

"Yes, Master," she said, using the term for the first time the whole week. Seeing her bright smile as she said the word, the flush to her cheeks being of arousal and girlish embarrassment rather than impotent fury and humiliation - well, I sprayed a thick load all over her pretty face. She just closed her eyes and opened her mouth wide, tongue stretching out to accept every last droplet of semen as it was deposited into her waiting mouth. Some of it, naturally, smeared across her cheeks, splattered along her eyelids, blocked off her nostrils. As she breathed in that position, the cum bubbled.

I reached down to run my fingers lovingly through her hair, smiling down at her. All that fury had melted away, squirted out of her cunt along with her lemon-lime juices, and she held her tits tight around my dick, her lips twisting into a giddy smile now that I'd finished coming. There was a happiness to her features that had previously been missing, a genuine enjoyment of her new position in life.

Seeing her like that meant I was still hard. I slid down her body, grasping her thighs and spreading her legs wide before thrusting my cock right into her wet sex. She squealed in ecstasy, jerking and thrashing beneath me. It was a hell of a sight, and the moment that her orgasm was finished, her hands went to her face, collecting all the semen she could, hungrily feeding it into her mouth as I thrust into her again and again, taking full advantage of the tight cunt that was currently wrapped around my dick and happy to be used by me.

I reached down for her hair, enjoying its silky soft feel as I ran my fingers through it, the strands faintly brushing against my bare skin, earning a delighted smile from being pet. Seeing her like this, so utterly debased and yet happily submissive - even though she still looked like her old self, to some extent, it was hard to think of revenge. She wanted me to fuck her, to dominate her, she wanted this so very clearly and obviously, all it made me want to do was satisfy those desires.

She started to speak, her voice a little stuttery from the force of my cock slamming into her cunt again and again. "Ah, fuck me, fuck me, Master!" "Thank you, Master!" "I love you, Master!" "I love your cock, Master!" Each phrase was full of so much desperate energy, as if the only thing she wanted to do was to manage to verbalize her feelings in the moment, and only just barely managed to, over the distraction of my cock in her constantly quivering cunt which was just drooling all over the place, lemon-lime juices sloshing about on the bed as her tits bounced.

I leaned down to kiss her. It was a heat of the moment thing, the first time I'd kissed her the whole time that she'd been here. She moaned in pleasure into my mouth, fingers grasping at my back, clawing at my bare body. Her legs locked around my hips, grinding me deep inside her, seeming to plead for me to unload in her sopping wet cunt. I decided to do exactly that, and she moaned in delight into my mouth as she felt my thick load splatter its way all over the inside of her waiting sex, as she felt my body do its level best to impregnate her.

I popped my lips off hers to that thought, leering down at her body, still dressed up in the maid uniform. She'd been washing it every day while I was out, so it was only moderately a mess, ruined by her juices and my cum from this particular sex session that had begun pretty much the moment that I got home from work and had yet to abate. "I lied about being on the pill," I told her, hand gently brushing along her stomach. She just smiled warmly at that. "I'm going to knock you up, Reese."

"Thank you, Master! Being your sex maid is so much better than my job. Should I keep going back to work?" She asked, voice sweet as silk as she did it, offering implicitly to gladly become my live-in sex maid, or else to keep earning money. "Any money I make is yours, of course, Master! Oh, and I can help you get my girlfriend too, if you want her," she continued.

It was too much, really. I just started fucking her again, shutting her up as my fingers began to dig into her tits. I loomed over her, admiring the way her eyes rolled up, her body thrashing from side to side. Her mouth sprayed spittle all around, some of it splashing back down onto her face, or onto the bed, as I fucked into her. She looked gorgeous like this, so sexy and delicious. I leaned down over her, nibbling at the exposed flesh of her neck, making her squirm and while. "Bite me, Master! Make me your woma~an," she squealed out, before coming all over again, grinding my cock inside her. Her fingers frantically ran across my bare skin, no doubt leaving little pink lines as she scraped here and there.

"I'll make you happy," I told her, the words seeming to come from nowhere, but felt so true as I whispered them in her ear. "I'll make you so fucking happy, living a life pleasuring me," I told her, and she could only drunkenly nod in the throes of her orgasm. I kissed the soft flesh of her cheek. "It's so much better than antagonizing me, isn't it? Aren't you sorry you ever called me twerp?"

Her eyes widened, genuine fear and sorrow appearing on her face, as she was suddenly reminded of how she'd been treating me in the past. "Yes, Master! I'm so sorry! Insulting you was wrong, punish me however you like," she said. The words came out in a rush, her breasts pressing up against my palms as if she was encouraging me to just maul her tits as part of her punishment.

Instead, I kissed her. I was even somewhat soft in the kiss, my tongue gently slithering into her mouth, teasing her palate. She squirmed and then came, jerking and bucking beneath me all over again, all that fear washing away from the simple reality of my cock in her cunt. I broke off the kiss and smiled down at her. "You don't have to feel sorry, Reese. After all, if you hadn't called me a twerp, I would never have made you my woman, and you'd be much less happy, wouldn't you be?" She could only nod drunkenly. "I'd be less happy too, never getting to see these sexy breasts and this gorgeous, feminine body, that all belongs to me, doesn't it?" She nodded again, faster this time. "If I told you to ghost your girlfriend, you'd do it for me, right?"

"Yesh, Mashter," she slurred out, drool running down her cheek as she spoke.

"What about your family?"

"Fuhk muh famillyyyy!" She squealed out the last word, thrashing as another intense orgasm ran through her body. Her eyes rolled up, her cunt gripped and squeezed and worked to wring me out, and I let go inside her all over again, kissing her hard on the lips as I did, my tongue forcibly invading her mouth, slithering all about, against her palate and tongue alike. She just moaned, her whole body vibrating with pleasure in that moment.

I pulled out of her, letting the thick trail of cum follow my cock as it exited her cunt, before falling onto my back. She just lay there, seemingly dead to the world, until I spoke. "Clean my cock," I ordered, and immediately she was crawling around, a drunken mess as she stumbled over to get in between my legs, her mouth opening wide to just suck my whole cock up. I gently pet her. "That's a good girl," I said, my voice soothing and sweet. She immediately came, her hips bucking at the air, a fresh spray of her lemon-lime juices hitting the bed beneath her as she slurped and gobbled on my dick. "You came fast from that," I noted, with a smirk.

She popped off my cock then, moving in such a way that her tits were immediately wrapped around it, to never let up on her constant cock-worship. She wore a bright smile, and explained the reason for her orgasm thusly: "That was the first time you called me a good girl, Master!" She eclaimed, before letting her breasts leave my dick and her mouth swoop back down.

"I'm sure I'll have lots of opportunities to call you it in the future, too," I told her, giving her a pat on the head, leaning back, and just enjoying myself for the rest of the evening.