Stepbrother With Benefits (17 page)

“Uh, sis... I’m pretty sure I’m not the only one here who’s naughty,” he replied, wiggling his thumb as Ellie’s sphincter tightened in protest around the penetrating digit.

“And bad girls need to be punished, right? Or so the theory normally goes...”

Jack snorted. “Yeah, you always were a hard one for mom and dad to figure out how to discipline. You kept thinking up excuses and loopholes they couldn’t easily counter!”

“Mmm, I do think your finger’s in one of those loopholes right now, Jack. Did you know my ass is cherry? Reserved for someone
very
special. I think my big brother will have to teach me a
hard
lesson for all those years of misbehaving and driving everyone nuts... by finally taking what’s always been his.”

Jack stopped thrusting and twisted his thumb a little deeper into Ellie’s bowels. Was she really offering what she seemed to be offering?

“Good god, Ellie; really? That would be amazing...” His voice trailed off wistfully.

“Do I actually need to say that you can do whatever you want with me? I trust you implicitly, Jack, and I’m not shy... you of all people should know that. Besides... I’ve always wanted to know what the big fuss was about anal!”

Without a moment’s hesitation, Jack withdrew from Ellie’s pussy and positioned his cock a couple of inches higher, rubbing the well-lubricated head over the creased star of his sister’s asshole. Centering himself, he pressed forwards... but to his intense disappointment, nothing much happened. Despite the ease of his thumb’s penetration, Ellie’s sphincter had clamped down so tightly on itself, that it was like trying to push against a solid surface.

“Uh, sis, I think you need to relax a bit.” Pushing with more force, Jack abruptly managed to shove his entre glans through the tight ring, but Ellie let off a piercing screech and he quickly backed off.

“Damn it all...” she muttered to herself. “I seriously don’t know how Rachel does this all the time.” Reaching behind her back, Ellie rubbed worriedly at her asshole, testing just how tight she was.

Moving Ellie’s hand aside, Jack spit on his fingers and stroked the clenched orifice, massaging until he could ease first one and then a second digit back inside.

“Eh, it’s really not that bad,” he commented, spreading his fingers and sliding them in and out to help loosen the tense ring of muscle. “You just need to get used to the idea of something going in the opposite direction of normal.”

Looking over her shoulder, Ellie pulled a face. “Eww, bro... like gross imagery there! You aren’t exactly sweet talking me into this.”

“If you don’t want to do it, then we really don’t have to.”

Ellie sighed and turned over, lying sideways on the couch and rubbing determinedly between her buttocks. “No, no, I want to at least give it a shot. I guess I just have a nervous asshole, huh? But now that I think of it, I remember Rachel saying it’s easier for her when she’s on top and in control. Can we maybe try that?”

“Of course. Whatever makes you comfortable.”

Ellie slid over and Jack climbed up on the old couch, reclining on his back and propping his head against the padded armrest. He could feel the cold wetness of the earlier puddle of cum pressing into the small of his back, and idly wondered just how much semen and other mystery juices he’d unknowingly been sleeping on for the past three nights.

Ick!

Straddling Jack’s waist on her knees, Ellie grabbed his throbbing cock and held it vertical, rubbing it back and forth along her slit and coating him with her lubrication. Then, she tilted her pelvis forwards and wedged it between the lower swells of her buttock, right up against the slight depression of her anus, before finally wiggling her hips to lock him in place.

With a determined look on her face, Ellie leaned back and applied pressure. Jack could feel his cock straining against what, to him, once again felt like a completely solid surface – and then he began bending, until suddenly he slipped out altogether.

“Damn it all!” whined Ellie. “I just don’t know if I can do this!”

“Try again... but this time, pretend you’re pushing something out.”

Ellie frowned, flashing that disturbed face at Jack again.

“Trust me, sis. It sounds counterintuitive, but I swear it’ll work!”

Moving him back into place, Ellie closed her eyes and concentrated.

At first, it didn’t seem like anything was going to happen. The pressure kept increasing to the point that Jack thought he was going to slip out again, but then something suddenly loosened – and all at once Ellie slipped several inches downwards.

Gasping loudly, his sister’s eyes sprang open in surprise. “Oh my god – it’s actually going in!” she exclaimed excitedly.

Grimacing slightly, Ellie pushed harder and Jack’s cock sank in slowly and steadily, until hitting a barrier that brought him to a stop just slightly past the halfway mark.

Ellie drew in a shuddering breath and leaned forwards, resting her forearms on Jack’s chest. “Oh wow... that’s uh, really something new there. Just gimmie a sec to get used to this, okay? You can stay hard for now?”

“Sure. You’re so tight, I couldn’t go soft if I wanted to!”

Ellie’s slightly uncomfortable look changed into a proud grin. “Mmm... that’s exactly the sort of thing a girl likes to hear!”

After barely two minutes of waiting, Ellie test-hunched her hips again, only enough to shift her body while her incredibly tight sphincter stayed locked in place. A few hunches later, and the movements grew large enough that she could begin sliding several inches up and down.

“Oooh, that’s actually not half bad,” she whispered, impaling herself a little further with every plunge.

“Uh, same here,” groaned Jack. His hands were wrapped tightly around Ellie’s hips as she moved, fingers squeezing repetitively into her flesh.

All of a sudden Ellie lunged forwards, dragging herself almost completely off before immediately shoving back down. She repeated the same motion several times.

“Hey... I think I’m getting the hang of this!” she commented in a more lively tone, straightening into an upright position so she could ride Jack in a more traditional cowgirl style. Lifting up and down carefully at first, Ellie gradually transitioned into a more general hopping motion as she loosened up, with her full breasts bouncing playfully on her chest.

When it began to feel like extra lubrication might be needed, Ellie stunned Jack by pulling off completely and shoving his cock back inside her sopping wet pussy. A half dozen strokes later, she reversed the process and returned his newly lubricated member to her ass.

“Oh my god, Ellie – that’s so hot!” he groaned.

“Hey... who wants... to waste money... on lube?” she replied between labored breaths.

Growing more confident, Ellie started bouncing faster and harder while rubbing at her clit, gasping and squealing as she forced him to penetrate deeper with every plunge.

And then, quite by accident, Ellie’s knee suddenly slipped off the edge of the cushion. Neither of them was expecting the entire weight of her body to suddenly bear down on Jack’s two-thirds-embedded cock, which strained valiantly for several seconds to hold them apart – until something deep inside Ellie opened, and her ass slammed down flat on his lap.

Tumbling backwards and nearly falling off the end of the couch, Ellie let out a deafeningly loud screech – an otherworldly blend of both pain and pleasure at having the entire length of her brother’s cock abruptly lodge deep in her ass. The sound was apparently more pleasure than pain, because Ellie’s shaky hand came down and grabbed her crotch, where she immediately curled two fingers into the gaping mouth of her pussy.

“Ugh, ugh, ugh,” she grunted, jerking her fingers sharply and repeatedly against the roof of her canal.

Ellie still hadn’t managed to lift her knee back onto the couch, and this worried Jack.

“Hey, you okay there?” he asked, noting with concern that Ellie’s face was turning a rather florescent shade of red.

Ellie abruptly screamed out and leaned backwards, her fingers a blur as they fucked frantically in and out of her pussy and filled the living room with wet squelching noises, all while a fine spray of wet droplets rained down on Jack’s abdomen.

Wait a minute... where was all that wetness coming from?

“Shit, shit, shit,” she wailed as her open palm smashed repeatedly into her clit. “I wanna come so bad, Jack... but it feels really strange!”

“Huh? What’s strange?”

Suddenly shoving her fingers as deep as she could, Ellie’s body stiffened and jerked violently, her bowels clamping down and rippling fiercely around Jack’s embedded cock. Her face twisted into a look of overwhelming agony, jaw pumping open and closed and her eyes becoming glassy and distant.

Ellie stayed locked like this for several seconds, seemingly trapped on the verge of receiving the pleasure she so desperately sought, but either unwilling – or unable – to finish propelling herself over the edge.

“Oooohhh god!” she whined through clenched teeth. “It’s so weird, I don’t know if I can do this!”

Reaching up, Jack tenderly caressed his sister’s side. “Please, Ellie,” he whispered. “You know I love you. Come for me.”

This simple, loving touch proved enough.

“Oh, fuck yes!” she cried out, the pained expression on her face instantly evaporating into a look of utter joy.

Jerking her hips upwards, Ellie’s fingers tugged so hard on the roof of her pussy that her previously miniscule hole gape open obscenely – and from Jack’s vantage point, he could see right inside her glistening canal as the interior walls twitched with the first orgasmic convulsion.

“Fuck, fuck, fuck!” wailed Ellie at the precise moment as an unexpected burst of wetness oozed out around her fingers; a sudden trickle of something hot and clear that burned like molten wax on Jack’s groin.

Shocked, Ellie jerked her hand away – resulting in a huge, pressurized jet of fluid gushing from her pussy at an almost horizontal angle, spraying Jack in the stomach and ricocheting off his skin only to rain down over his head.

Shrieking in total astonishment, Ellie immediately slapped the hand back over her pussy to stop the squirting.

“Oh, no no no! Fuck! I knew something was wrong!” she wailed, biting her lower lip and whining as though in pain.

As Ellie worked to keep the unknown liquid from escaping her body, the teen’s abdominal muscles began to convulse visibly – and when juices began to leak out around her fingers anyways, she howled in despair.

“I’m so sorry, Jack – I just can’t hold it in!” she gasped, finally yanking the hand away and allowing the gushing to resume with even greater volume and force.

Squeezing her eyes closed and moaning “Oh my god!” over and over again, Ellie’s trembling fingers rubbed the swollen bump of her clitoris in rapid circles, her long inner lips buffeting back and forth in the hissing spray from her urethra and flinging droplets in every direction... thoroughly soaking her brother, the couch, and even herself!

A few seconds later, the uncontrollable squirting stopped just as abruptly as it started. And yet, Ellie’s orgasm continued for another half minute – with her vaginal muscles visibly pulsing in the most dramatic fashion. Eventually, her contractions grew weaker and further apart, until she finally collapsed backwards on Jack’s legs and his cock came free of her ass.

Jack’s heart was beating a mile a minute. He’d felt every single moment of that orgasm.

Ellie lay shaking on Jack in an apparent state of shock for some time. Eventually, she looked down her body, propped herself up on an elbow, and trailed a trembling finger through the wetness coating his stomach.

“Oh, Jack... I’m so sorry! I just don’t know why... what the hell
is
all this shit? I’ve never come like that before!”

Already well aware of what had happened, Jack laughed and patted his sister on the thigh. “Sis, please don’t apologize! Because if porn is anything to go by... then you just had something amazing happen. You squirted!”

“Squirted? What the hell? I thought that shit was all fake!”

“Seems like you’re living proof of the opposite! And trust me... it’s damned hot!”

Ellie stared in fascination at her pussy for a moment, and then burst into a fit of giddy giggles.

“I squirted... goddamn! It felt like totally amazing; like nothing I’ve ever felt before!”

“Glad to hear it. It’s not every day you get to learn something completely new about your body, now is it?”

“Especially something so fuckin’
cool!
I mean... I’ve heard about that kinda thing before, but I thought girls just shot water up their pussies or pissed! Oh god, it’s not actually piss, is it? I’ll just die if it is!”

Scooting her butt further down the couch, Ellie bent over and sniffed Jack’s stomach. “Hmm... doesn’t smell like piss...”

Looking into her brother’s eyes as if to check whether what she was about to do was a good idea or not, Ellie stuck out her tongue and cautiously dabbed it in the tiny puddle of juices trapped in his bellybutton. Determining that it wasn’t disagreeable, she sucked up the puddle and smacked her lips, trying to figure out just what it was her body had produced.