A Challenge from Within

Story by Jeeves on SoFurry

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A new dildo, and a long, luxurious evening spent preparing to take it for the first time. For Samantha, there probably isn't a better way to end the day.


This story was written for HandofBlades as part of my Patreon Request Days for May. It contains masturbation involving a consenting adult lady. :3

A Challenge From Within

Samantha shuddered happily a she fell limp upon the couch, blushing and moaning as the thick dildo slipped free from her pussy, dripping with the residual juices of her orgasmic ecstasy. The tigress raised her head as best she could, looking down over her heaving breasts and feeling her face growing all the more rosy beneath its fur as she saw the sizeable trail of wet spots from the force of her climactic ejaculations.

Normally, this would be the end of such an evening. Lying on the couch spent, gentle music playing, a half empty bottle of wine close by and several toys all used and dripping wet resting upon the glass coffee table. Normally now she'd throw on her robe or just stay naked depending on the temperature, laze around watching some TV and continuing to drink, before finally either wandering up to bed or simply taking a nap right here until she awoke naturally and made her way upstairs only then. But today was special. Today was a day of new challenges. New extremes. And of course, a new dildo.

Whimpering bashfully even as she reached out for the toy in question, leaning forward to grab it not from the coffee table but where she'd left it even closer by, resting upon the couch with her, Samantha drew it up to her crotch. She nibbled on her bottom lip as she rubbed its girth between her damp lips, marking it with her juices for the first time. Even just looking at it now, a part of her wanted to call this whole thing off. After all, she had nothing to prove. She wasn't some size queen who had to find a bigger toy when her former biggest was no longer a challenge. She could be perfectly satisfied with what she had.

And yet...

"O-oh..."

The tigress groaned as she watched that replica dragon cock rub up and down her pussy, the hand holding it by its base unable to even wrap itself the whole way around the girth of the shaft. It was obscene how big this was, and it was incredible how it made her feel. So small, despite the fact that she stood close to seven feet tall. So unprepared, despite the fact she'd spent the past three hours working herself loose enough to even attempt this feat. And so very horny, despite the fact that she had cum no less than four times just getting herself loose enough to even attempt taking it.

Once again reaching down into the couch cushions surrounding and supporting her where she lay, the tigress soon emerged with a small bottle in her hand. She may have been soaking wet from her past experiences, but when it came to trying a new toy on for size there was no such thing as too much lube. She doused the toy in the slippery liquid substance, ensuring that the entirety of its head was glistening and that thick rivulets of the lube were trickling all the way down its length before she even considered moving on. And even when she did so, she took everything from that point onward purposefully and exceptionally slow and steady.

Moaning happily, for maybe ten minutes or perhaps even a little longer Samantha spent time rubbing the toy's head between her lips. Occasionally she would push forward ever so slightly, grazing the opening of her depths with the very tip of its tip, but nothing more. It was more about getting her body used to its proximity than anything, letting herself loosen up mentally as much as physically to the idea of that monstrous cock fitting inside her pussy. It felt like it was working though, and by the time those ten minutes had passed Samantha had upgraded her chances of taking even a fraction of that toy's length inside herself from not a chance in hell to extremely unlikely.

After that, she paused. She didn't try to do anything with the toy, leaving it leaning rather deliciously against her crotch as she reached over to the coffee table and plucked her wine glass from its surface. She took a few more sips, savoured the rich flavour of the deep ruby liquid, and then purposefully set it back down with a happy sigh.

Several times she repeated this method. A little teasing to get her body more worked up and ready, then some wine, then a little more time dedicated to her and the toy growing better acquainted. This continued until another glass of wine was gone and re-filled, and that glass in turn had been emptied by about half. By that point Samantha was shaking with anticipation, her body ablaze with arousal as if it hadn't already been treated to multiple orgasms that evening. At last, she was ready. Or at least, she was ready to start in earnest.

"Mmh... o-ohh god... fuck..."

It started slow. So very slow. Samantha eased the tip of the cock against herself, rubbing and turning it over and over in her hands to find the best angle of attack. She could feel the slickness of the lubed up cock certainly helping, but it didn't make it any smaller. It didn't stop it from stretching her wider and wider before she had even gotten anything actually inside. The tigress panted, mewled, shuddered and squirmed as she fought to grant herself what it was she most desperately desired in that moment. Fulfilment in the most physical, literal sense. She rocked her hips. She lifted them up off the couch, tilting the toy upward at a slight angle to see if that would make even the slightest bit of difference even as she feared that her body was at its limits, and that she would not be able to get it inside.

Then, all of a sudden, her eyes bulged.

She felt something let go. Not with pain. Not with any sort of real discomfort at all. But, as she tried out that odd new angle with the toy pointing up from beneath where her pussy now hovered, she felt some last remnant of tension let itself loose from within her body, and the head of the dragon cock disappeared into her pussy with a hot, thick slurp.

She dropped urgently back to the couch as a strangled cry escaped her, and her body clamped down hard around the toy. Or rather, it tried to. It tried, but was incapable of doing so quite simply because her body was already stretched to capacity, thus there was no space for it to contract and clamp any further. This didn't make sense though, not to her muscles. Not to her instinctive urge to convulse and squeeze around objects placed inside of her pussy's depths. Thus, it tried again. And again.

Samantha grunted. Gasped. She whimpered and writhed upon the spot as her body seemed to lose control. She wasn't even trying to push the toy in any deeper yet. She wasn't moving it at all, just holding it perfectly in place. Yet with her body doing what it was doing, entirely outside of her own control, the result was inevitable.

The tigress panted. She clawed at the back of the couch with her free hand, and stared down over her once more heaving chest in stunned wonder as her own body gleefully rebelled against her.

With a shriek, followed by a deep and rumbling roar, she came. She came, and of course as she did so the thick, almighty dragon cock only a couple of inches deep inside her was launched out by the fierce squeezing and potent, copious squirting of her pussy. It flew across the couch as the tigress kicked, writhed and yowled in sweet ecstasy, the drumming of her juices against the fabric following in its wake. It was still and silent long before Samantha could bring her body back under control though, twitching and whimpering more than half a minute after that devastatingly intense orgasm at the behest of only a fraction of that cock had begun. And even then, as she found herself spent once more, merely looking down at that lubed up, glistening and now also arousal stained cock was enough to make her tremble and writhe anew.

"O-ohh... god..."

She blushed. She whimpered, and with one trembling hand she reached out from the couch towards the coffee table, and towards the wine glass upon it.

Samantha wasn't ready to consider herself beaten yet. She wasn't ready to end her first night's attempt with two or three inches being the most she'd been able to achieve. But if indeed she was going to achieve more than that, she'd need two things.

First, the tigress would need to take a few moments to compose herself. To let her body recover, and her pussy to stop flexing and quivering as though it was going to start her cumming all over again at any moment just thinking about the toy.

And secondly, she was going to need more wine.

By Jeeves

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