Anal - Breaking in May's ass

Your eyes wander over May's slender form as you circle her, wondering just how to pass the time until her soon to be extra fertile womb is ripe for the taking. With each pass, you watch May's azure eyes stealing nervous glances at you, a mixture of nerves and excitement running through the young heiresses mind, and you continue to let her sweat it out. With each pass, your eyes are drawn to May's perky ass, the sweet heart-shaped perky cheeks that conceal her tight, possibly untouched by another person. Toy's, on the other hand, you were fairly confident May has at least experimented.

You give May a predatory smile. "Show me your toy collection," You say in a commanding growl.

"Yes, mistress," May whimpers scampering over to her bed and sliding out a previously concealed draw out of the frame.

You slowly walk over, watching May tremble with a mixture of fear and excitement as you approach the open draw and peer inside. You see various dildos and vibrators ranging from mundane to exotic in shape, size and material. Admittedly your eye is drawn to some of the toys made of precious metals and materials, some you recognise that can alternate in temperature and hardness and one suspiciously anatomically accurate attachment which you suspect attaches to a Robo pet. However, your eyes hone in on a collection of jewelled plugs of various sizes in a specialised case and, more importantly, a bottle that occupies one of those spaces.

"Looks like we have ourselves a little butt slut," You say with glee, opening up the case and holding up one of the larger plugs as the colour drains from May's face.

"I've only been able to use the smallest one," May replies nervously before rapidly adding. "Mistress,"

"Awwww, is that so?" You reply in a tone of mock disappointment.

"I'm afraid so, Mistress," May replies, sounding almost genuinely apologetic.

"Well, lucky for you, your Mistress is going to teach you," You reply with a wicked grin.

"Teach me?" May asks nervously, her Azure eyes flicking down to your sizable shaft, easily thicker than even the largest butt plug in her collection.

"Oh yes," You reply with a cold smile. "And if you forget to address me by Mistress one more time, May," You add in a warning tone. "I'll skip the lube and give you a pillow to bite down on instead," You conclude.

"I'm sorry, Mistress," May quickly apologises.

"I'm sure you are," You reply with a smile. "Now bend over that desk," You command, gesturing your head towards a large black desk against the wall.

May walks with some hesitation towards the desk; she walks slowly, but even so, her room, while vast, was hardly infinite, and soon she reaches her desk and slowly lies forward, leaving her rear dangerously exposed to you. Grabbing the bottle of lube, you take an equally long a deliberately slow pace, ensuring May has time to appreciate each footstep ringing out. You take a moment to admire the ass you would shortly be breaking in, catching a glimmer of May's tight, pinched butt hole.

Once you've reached May, you rest your thick hard length between her soft asscheeks. You hear a soft gasp from may as she finally gets the full impression of what would soon be going inside of her. You roll your hips back while parting May's cheeks with your fingers, the swollen tip of your cock slipping down and over May's tight puckered ring. You hear May let out a whimper and tease your crown against her ass, smearing her hole with your sticky precum. You even give her a slight fright when you gently tease your length against May's asshole, threatening to penetrate her here and now, without any lube. However, just as the pressure mounts and you feel May's hole start to give under the pressure of your thickness, you slip yourself over the hole.

You hear May soft sigh with relief, although she soon tenses up again when she feels your slippery fingers coat her tight asshole with the lube. You were in a slightly cruel mood, given the topiary she's made you do with your family tree, but you'd been on the receiving end on an overly zealous and impatient partner looking to mine your brown dwarf for all it's worth. Besides, you were here to push May, humiliate her just the way she wanted, if not taking much more than she had bargained.

Slowly you drip more lube onto May's exposed ass, slipping a finger inside her tight channel and gently massaging the inside, giving May the chance to adjust and possibly feel a slither of pleasure before adding a second finger. The process takes a minute, but soon you've got May nice and lubed up. Finally, you take a generous amount of lube and begin to coat your thick throbbing cock. May's near virgin hole might never have taken anything close to a large as your length, but at least now you can be sure it won't cause her any harm.

"There we go, all nice and slippery," You coo softly while you guide your cock towards May's asshole.

"Please, Mistress, be gentle," May pleads.

"Don't worry, I'll start nice and slow," You reply gently before spanking May's ass hard. "But once you're ready, I'm going to ravage this ass," You explain. "And you're going to love every second of it," You growl.

In position and ready to pluck May's anal cherry, you take a moment to glance up and the desk and sky a dormant holo display, which gives you a wicked idea. "I want to watch your face while I do this," You say in a sultry tone. "Get one of your drones to record your face and put in on that holo," You command, slapping May, leaving a red handprint out her soft heart-shaped rear.

"Yes, Mistress," May says with some ****, reaching over the holo screen wakes and then with a few gesture commands, a small silvery drone barely the size of a fingernail floats out before May's face. Soon you have a large projection of May's face before you, large enough for you to make out each microexpression as you tease your thick length into May's well-lubed hole, the muscular ring gently giving way to the dense mass of flesh pressing into it.

"This'll be easier if you relax," You offer, pressing yourself forward; You feel the tight muscles of May's asshole parting wider and wider to begin to accommodate your shaft.

You watch May bite down on her bottom lip and take in a few deep breaths before she relaxes, and your tip effortlessly glides past her puckered ring and sinks into the welcome warmth of May's rear.

"Fuck, that's big," May hisses, her tight ring squeezing the tip of your shaft while you patiently wait for her to regain control of her breathing.

Over the next few minutes, you repeat the process, sliding another half an inch into May's sweet ass, watching her face contort as she struggles to accommodate your thick throbbing shaft in her ass. Then when May finally calms down, you feed another half inch and repeat, until eventually, you find yourself balls deep inside May's ass.

"There, that wasn't so bad, was it?" You say calmly, taking a moment to enjoy the sensation of May's tight ring squeezing the base of your cock.

"No, Mistress," May pants heavily, adjusting to the feeling of having her ass dominated by your thick swollen length.

"I promise you it'll feel good," You coo softly. "It'll hurt a little, but the good kind of hurt," You add, playfully slapping your hand over May's ass, causing her to tense up around you, her ass trying to pull you deeper into her.

You give May a minute before slowly sliding yourself out of her tight ass, enjoying the occasional squeeze from May's ass. Then just as you almost pop free, you press your hips forwards and feed your cock back into May's ass, without pause this time, but still at a gentle pace. You watch May whimper as she struggles to accommodate your cock once more. You continue to ease yourself in and out of May's ass until the soft, pained whimpers turn into soft moans of pleasure.

"You're starting to enjoy this, aren't you?" You ask with a giggle.

May is simply letting out a moan in response as she feels your balls connect with her neglected pussy, which by now was drooling with hunger, which you ignore; for now, you'll have plenty to feed May's pussy once you were certain it was ripe and fertile. So instead, you pick up the pace just enough to prevent May from enjoying things too much. For every minute of adjusting to the new speed in which you glide your thick throbbing length in and out of May's smooth back passage, you allow her one minute to enjoy herself once she's adjusted.

Until finally, 20 minutes after plucking her anal cherry, you were able to give May a decent ass fucking, your weight cum swollen balls colliding into May's dripping clit. With each heavy thrust, you could feel May's arousal showering your sack with her juices while her asshole flexes and squeezes your swollen shaft, almost refusing to let you slide out.

"Mmmm getting nice and juicy for me," You groan as you slam yourself back into May's ass. "Must be driving you crazy with those pills making your pussy ache, **** to breed," You tease, spanking May's ass hard.

"Fuck Mistress, I want it so badly," May pleads.

"I know you do," You coo. "But we're not finished with your butt slut training," You add with a grin, reaching forward and entwining your fingers in May's short black hair and pulling her back. "Watch me make you cum like a slut," You growl, your grip forcing May to watch herself.

With your grip on May's hair, you **** her back to arch as you begin to pound her ass harder and harder, the heiresses mewling with a mixture of pleasure and pain. You thrust harder and harder, drawing May closer and closer to that orgasm that's been slowly building now. Your orgasm has also been brewing the last while nicely, although while you were eagerly looking forward to making May cum from having her ass pounded, you're own cum was being saved. You were happily edging yourself with May's ass to brew up an extra heavy load to unload in her for the first of her many breedings.

You drive yourself in and out of May's ass, pounding her mercilessly while pulling the young heiresses hair. May panting and groaning more than grimacing with the discomfort as your drive her closer and closer to the edge. "Tell me how much you love your Mistress' cock," You growl.

"I love it," May pants, her breathing heavy and laboured.

"What do you love?" You demand while slapping May hard on the ass.

"Mistress' cock," May whines in return.

"Mistress' cock doing what?" You demand, slapping May's sore rear again.

"I love Mistress' cock pounding my ass," May groans, the muscles in her body tensing slightly as her orgasm draws nearer.

"How many cocks have you had up your ass?" You demand.

"Just yours, Mistress," May replies.

"An anal virgin, and in less than an hour, you're a real butt slut aren't you?" You ask, wrapping the fingers of your free hand around May's throat.

"Yes! Mistress," May groans.

"You're about to cum from me pounding your tight ass, aren't you?" You ask.

"Yes, Mistress," May replies, her body shaking slightly as your continue to slam yourself in May, your hips connecting with a heavy slap as they collide with May's perky rear.

"Alright then, cum for me slut, cum on your Mistress' cock," You growl, pulling yourself out of May's ass, admiring how her once virgin ass gapes for a moment before slamming yourself into May in one final primal thrust.

May howls and shudders in your arms, her body feeling limp as she begins to orgasm hard. You feel May's neglected pussy spraying your balls with its juices while May's asshole flexes and tightens around your thick throbbing shaft. You keep May held upright, forcing her to watch the faces she makes as you give her what was likely the first of many anal orgasms of May's life.

Eventually, May comes down from her orgasmic high, her ass finally relinquishing its tight iron grip of your cock, allowing you to ease yourself off and out of May's ass. By your estimate, you still have a couple of minutes before the two powerful fertility pills you **** May to take kick in. So first, you glance down at your glistening cock, sticky with a mixture of residual lube and May's anal secretions. Then you look up at the holo at May's panting face, her soft full lips looking like they could solve two problems and further **** the heiress.

"All right slut, almost time to breed," You growl, rolling May onto her back and resting a hand on her slender flat stomach. "But first, I need to clean up," You add, flashing May a devious smile.

"Mistress?" May asks hesitantly, her breathing still heavy while she catches her breath.

"Open wide," You say, pulling May forward until you're straddling her chest, cock poised right before May's lips.

"Mistress, No," May pleads.

"Open wide," You repeat in a harsher tone. May shakes her head, unwilling to cross this final step, at least not without a little encouragement. "Are you disobeying an order?" You ask in a cold tone.

"No, Mistress," May pleads, although you can tell by the look on her face that this is an act. She knows she'll be sucking your dirty cock soon; she's just giving you a reason to be more forceful with her. Of course, it takes the fun out of it a little for you, but you're fairly sure it'll help you sleep easier at night, knowing you didn't actually **** May to do something she wasn't willing to do.

"I said open up," You growl, thrusting your cock against May's lips and pinching her nose shut with one hand.

May play-acts the struggle for a few seconds before opening her mouth and wrapping her lips around your cock, her tongue gliding alongside the underside of your shaft, giving May the first taste of her own ass. Assuming she didn't sample it from one of the butt plugs from her early anal experimentation. Still, in either case, May isn't dissuaded from greedily sucking your cock, regardless of how tainted by her own taint it was.

You take a few moments to relax and enjoy May's skilful oral ministrations, making a mental note of some of the tricks she employs with her tongue for use in your own repertoire. Although when you catch one of May's fingers slinking its way towards your own ass, then you decide that May's gotten a little too relaxed.

"Did I give you permission to finger my ass?" You ask in a sultry tone. To which May immediately slides the offending digit down and between your dewy pussy lips instead. "Don't recall giving you permission to finger my pussy either," You growl.

May attempts to apologise, her words garbled with your cock in her mouth.

"Well, this can't go unpunished," You muse before smiling evilly at May, "I suggest you relax your throat," You say coldly before shifting your position and forcing a couple more inches of your cock into May's mouth. You hear May cough and sputter around your shaft as your **** yourself down her throat. "I was happy to let you suck away, but now I'm going to make sure all you can taste is your own ass when you breathe," You say as you begin to fuck May's throat.

May coughs and sputters, her eyes watering and going red as you fuck her face. You know to keep this short, not least because you don't want to cause any physical harm to May, but also because you can feel yourself getting close. Your balls churn and writhe against May's chin, so swollen and heavy with potent seed, eager to be let loose in May's fertile womb.

You allow yourself to get right on edge, your cock swelling and throbbing in May's throat and mouth, copious amounts of precum oozing down her throat. Countless numbers of nanites are being absorbed into May's body, all to ensure, whatever high tech birth control she might employ after this fails, just in case she gets cold feet with her own plan. You hold yourself on the edge of climax, cock twitching and throbbing deep inside of May's throat, ready to erupt, before you eventually slide yourself free. Leaving May coughing and sputtering, wiping her tear-stained eyes while she catches her breath.

You step back and marvel at the mess you've made of May's body, her ass still gaping slightly from where you pounded her, her make up running from where tears had filled her eyes while she choked on your dirty cock. Then there was the drooling mess of her juicy pussy, looking oh so inviting, ready for you to pin her down and breed her. Your cock throbs as you lick her lips while wondering where to seal the deal with May's womb.