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Chapter 21 by Genericc616 Genericc616

What sort of tests does your Ruby have in mind?

Your Big Sister set about getting you as horny as possible

Your mind is spinning with a myriad of conflicting feelings about what was about to happen. Excitement at the prospect that Ruby's plan might work, that you might finally feel like you're in full control of yourself again. Fear and anxiety that the plan might backfire and you only prove what you're afraid of, that you can't control yourself. In a short while, you'll find either salvation or damnation at the hands of your Older Sister. Swept up in the maelstrom of your mind cycling back and forth between hopeful and fearful, you find yourself back home with Ruby leading you up the stairs to your room before fully processing what would be happening.

"Alright, first things first, let's get naked," Ruby says finally letting go of your hand and beginning to strip. "That means you too, Sis," Ruby adds with a giggle as she pulls her top off revealing her bra straining to keep your big Sister's sizable tits contained.

"Sure," You reply with a nervous laugh, pulling off your own top.

You try your best to avoid glancing over at Ruby as she sheds more and more of her clothing, knowing it would be a struggle to remove your jeans with a hard-on, although you can't help yourself when your Sister bends down to remove her socks, giving you a great view of her ass.

"Come on, stupid things," You groan, trying to wrestle your legs free from your jeans, while blood rushes to your cock.

"Need a hand?" Ruby asks with a flirty giggle, her eyes very much focusing in on the big bulge in your underwear.

"Not helping," You groan, before finally freeing your foot from their denim prison leaving you just in your bra and thoroughly tented and precum-stained panties.

"Damn, Nice cock, Sis," Ruby adds with another sensual giggle, the comment causing you to blush, although it's not very noticeable as your blood is preoccupied lower down in your body.

Your older sister continues to stare at the district outline of your rapidly swelling length, before continuing to shed the last few of her garments. You focus on unfastening your own bra, trying your best not to get too caught up staring at your Big Sister's body. An extremely difficult task, when Ruby bends over giving you a prime view of her rear, and the large wet patch in her panties. By the time you finally can pull your eyes away from your Sister, both your nipples and cock and fully swollen, much to Ruby's delight.

"Holy shit," Ruby gasps when you finally pull down your panties and she sees the full majestic of your swollen shaft. "I said it was nice before, but Godamn, Amy you're huge," Ruby adds with a huge smile on her face.

"Thanks," You reply nervously, feeling more than a little uncomfortable being not only naked but also rock hard in front of your Older Sis, before really starting any of her 'tests'.

"Can I touch it?" Ruby asks with an impish smile on her face.

"I don't know if that's such a good idea," You reply, swallowing hard as your eyes linger on Ruby's naked form. You can't help but admire her slightly curvy form, her big DD tits, or the strip of short blonde hair in a neatly shaved line above your Older Sister's glistening pussy.

"Oh come on, Sis, It's just my hands," Ruby replies in a sensual tone. "Besides we need to build up that tolerance of yours," Ruby adds with a soft smile while taking several slow steps towards you, her large tits jiggling enticingly with each step.

You try and fail to pull together a cohesive reason why your Older Sister shouldn't do this, instead you nod gingerly and adjust your stance to give Ruby the best access to your big throbbing cock. Ruby smiles at you, before slowly reaching out with one hand, teasing a single finger along your length, your cock twitching to your Siblings touch. Your breath catches in your throat as Ruby begins to wrap her soft hand around your shaft, the swollen mass too big for her to fully wrap her hand around it.

"Fuck, it's even bigger up close," Ruby laughs nervously before smiling. "How does my hand feel?" She adds with a smile that would tell anyone who could see it, that she already knew damn well how good it was making you feel.

"Amazing," You groan as your Big Sister effortlessly slides her hand up and down your shaft, using her fingers to tease across your sensitive swollen tip, using your own oozing precum to lubricate her hand.

"Good, now for the first test, try not to cum," Ruby says softly as she begins to stroke you.

You stand there completely at Ruby's mercy as your Big Sister slowly strokes your cock, driving you wild with each pass of her hand as she alternates her grip, twisting and teasing your cock. While it pales in comparison to the pleasure you felt being balls deep in the other family members you've already used your cock on. There's something about not being the one in control, combined with the expert nature of your Big Sister's handiwork which leaves you paralysed with pleasure.

"How can a hand feel so good," You groan, your toes curling with the pleasure.

"What can I say, I'm good with my hands," Ruby replies with a giggle. "I also might have gotten my fair share of practice with the guys I went out with before my idiot ex-fiance," Ruby adds with a laugh.

"Your hands can't get pregnant I guess," You reply, letting out a loud groan of pleasure as Ruby begins to work her thumb into the sensitive underside of the tip of your throbbing length.

"Nor the mouth," Ruby giggles, her reply making you shiver with excitement.

"Wow," You groan.

"Yeah, you might not have been able to tell, but your Big Sis had a bit of a slut phase in college," Ruby admits with another sexy giggle.

"No way," You reply in disbelief, "You were far too focused on your studies," You add.

"Don't believe me, huh?" Ruby says with a wicked grin on her face. "Well, I guess we can move onto the next phase and you can feel for yourself," Ruby says with a soft laugh.

Before you can respond, Ruby kneels down in one swift blur of movement, opening her mouth wide and taking your thick swollen cock into the hot wet confines of her mouth, her lips pursing tightly around your shaft and she begins to suck. You let out a long groan of pleasure and your Older Sister begins to bob her head back and forth on your cock, slowly taking more and more of your impressive length into her mouth. Your hands clench into fists by your side as your try and process the new waves of pleasure flooding in.

You know you need to resist, to hold back as best you can, a skill which you'd acquired from the numerous times you've had sex with your Cousin, Aunt and Half-Sister over the last few weeks. Although never before have they been quite as thoroughly tested as they were right at this moment. The sensation of your Big Sisters blowjob coupled with her skilful hands still working the base of your shaft is driving you wild. The fact it was Ruby doing this to you and all the complicated feelings that were once buried now dug up to the surface, only heightening the pleasure.

"Holy fuck, what the fuck was wrong with Jack," You groan in pleasure, the thought of any man leaving anyone as skilful as your Older Sister is simply unthinkable right now.

"His loss," Ruby says with a giggle.

"My gain," You groan, leaking a fresh batch of precum into Ruby's mouth.

"This is supposed to be a test you know, you're not supposed to be enjoying it this much," Ruby adds with a soft giggle, giving her mouth a brief break and introducing her other hand to work her saliva into your shaft.

"Oh sure, how about I go down on you and tell you not to enjoy it," You groan back

"Promises, Promises," Ruby replies in a teasing manner before opening her mouth wide to take you into her mouth again.

You glance down and watch your cock disappearing into your Older Sister's mouth, expecting her to stop around the same point and begin to suck again, but to your surprise, she keeps going. Soon you feel pressure around the tip of your cock as Ruby eases you into her throat, the wet warm lips going lower and lower until Ruby almost has her lips pressed against your body. Ruby pulls herself back, taking a moment to steady her breathing before going back in to take you deeper. Until this time you feel your Older Sister's lips pressing into the base of your balls and body.

If you were struggling to keep your composure and keep yourself from cumming before, now it was an all-out war to keep yourself from erupting down Ruby's throat. Especially when she opens her eyes and looks up at you while your cock is down her throat and this is just the beginning. Ruby pulling herself back and sucking your cock like a woman possessed. Alternating between her hot and sloppy blowjob and deepthroating you, all the while her fingers caress and tease your swollen balls, practically trying to tease you into submission.

You howl and groan in pure ecstasy as your Older sister drives you right to the verge of cumming, before easing up on her technique and giving you a moment to regain your composure. You lose count of how many times you find yourself at the very edge of your limit, your cock swollen and twitching dangerously, so eager you pump your thick load down your Sister's throat.

Then almost as if a switch is flicked, Ruby suddenly pulls her mouth off your cock, stands up and steps back. "Well, I'd say you passed the first a second test with flying colours," Ruby says with a giggle, while you stand there panting heavily, your swollen balls aching with how full they feel and how often they were denied a chance to empty.

"I did?" You ask, uncertainly, barely able to keep yourself upright.

"Yeah, although I think we might need to take care of that before we go any further," Ruby replies gesturing towards your thick throbbing cock and swollen sack.

"Right," You reply.

"I think you need a reward for doing so well," Ruby says with a smile, before walking toward you. "How about you jerk that monster for me and cum all over me," Ruby offers with a smile.

"Are you sure?" You ask hesitantly.

"Sure, the first test was about physical self-control, we'll cover mental self-control later," Ruby explains with a grin.

You nod in agreement, not quite able to follow your Older Sister's logic by this point, but equally far too horny and eager to cum to question it. So you wrap your own hand around your shaft and begin to stroke yourself while looking at Ruby's naked body. It doesn't take long for you to work yourself back up to the blissful point of no return.

"I'm close," You grunt, feeling muscles in your body begin to tense.

"Good, now paint your Big Sis' slutty face with that big fat load," Ruby purrs, kneeling down in front of you and closing her eyes.

The sight of your Older Sister before you like this is too much to handle and you find yourself crashing over the edge as you begin to cum hard. Your swollen cock throbbing and pulsing as your thick cum rockets up your shaft, before pausing the dizzying moment before the first heavy pulse launches the first rope of your cum into the air and onto your Sister's face. You let out a long protracted groan as your cock continues to throb and pulse, more and more of your thick cream spattering across Ruby's face until she's almost completely covered in your cum.

By the time you're done, your legs give out and you fall back to the floor panting hard, the last of your cum oozing from your swollen tip. "Oh shit, I think we both might have overdone it," Ruby says with a giggle as she runs her tongue out and gathers up some of your cum from her face. "Although as nice as it tastes, I'm glad I didn't try to swallow it, there'd have been too much," Ruby adds with another giggle as she blindly shuffles around before finding something to wipe her face off with.

You glance over at your Older Sister, watching with interest as you see her use her own clothes to get your cum off. The sight of your own seed soaking your Sister's face makes your cock twitch and blood that had rapidly left once you were done, begins to make the return trip to your cock.

Does Ruby have any more 'tests' in her for the night?

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