The Limits of Imagination Ch. 06

You recovered yet? ;)

Barely. Still a little tender!

You'll be fine it's only been a few hours

Easy for you to say.

You weren't carrying around half a kg from your ballsack for 3 hours...

And you didn't have something spontaneously

vibrating inside your pussy in a public park...

Fair enough.

Anyway, I've got an idea if you're up for it

I'm not sure about your ideas at the moment...

This one's more of an...equal opportunities idea.

We both benefit so to speak

Alright, let's hear it then.

...

...

...

Let's buy each other butt plugs...

😳

As in you buy me one and I buy you one?

Exactly

Alright, I'm in.

Great! Get it delivered before the weekend. I'll come over

around 4 on Saturday and we can play

Sounds like a plan.See you Saturday!

By the way...I've never had anything up there before...

I'll take that into consideration ;)

***

"So, really this time, who gets to go first?" Jack asked.

"Why don't we flip a coin?" Elle suggested.

"You got one on you?"

"In my bag on the dressing table."

She stepped out of the dress gathered around her ankles and retrieved a coin from her purse, returning to sit cross legged on the bed in front of Jack.

She'd arrived at Jack's house a few minutes after four. After a strangely formal greeting and a few minutes of awkward conversation in the kitchen, during which neither of them brought up the true subject of their meeting, Jack suggested they go up to his bedroom. Once there, Elle brought up the question of how they were going to proceed. Unable to decide, they'd settled for at least getting naked, which felt like a logical step forward.

Now, sitting down on the bed beside him, she balanced the coin on her finger and thumb.

"You call it," she said before sending it spinning upwards with a crisp ping.

"Tails!" he cried as it reached its apex and landed on the bed beside them.

"Tails it is, you first!"

Jack's heart was beating rapidly as he moved to the centre of the bed where Elle had placed two pillows, one on top of the other.

"Get on your knees and lay your chest over these," she said, patting the pillows.

Jack followed her instructions, placing his knees below his pelvis and laying down across the pillows, his head turned to the right where he could just about see the top of his backside in the mirror above the dressing table.

"Spread your knees apart a little."

He felt exposed as he slid his knees across the smooth sheet, conscious of his dangling balls and semi-hard dick.

"Now, pull your cheeks apart and hold them there."

Jack's heart rate increased again at those words. He lifted his hands slowly to his backside, his chest sinking further into the pillows as he did so. Closing his eyes he placed his hands on his cheeks and pulled them apart, exposing his asshole to the world.

Standing at the foot of the bed, Elle took in the sight of Jack spreading himself open before her. The tip of his cock was just visible below his low-hanging balls, a delicate strand of pre-ejaculate extending down to the white sheet, betraying his arousal. It was the first time she'd seen him from this perspective. She noticed a vertical seam of skin delineated the middle of his sack and extending up between his legs where it terminated at the knot of his anus.

Moving closer, she traced a finger lightly through the dark hairs surrounding his sphincter, marvelling at their softness. Jack's hole reacted instantly to the proximity of her finger, contracting visibly. Elle traced her finger down along the seam of skin and over his testicles. Closing her hand around the warm orbs, she gave them a gentle squeeze before running her finger back upwards along his sensitive skin, pausing right atop his hole. She could feel it contracting beneath the pad of her finger.

"You ready for this?" she asked when his sphincter eventually settled.

"Mmm hmmm," Jack moaned quickly before he could change his mind.

Removing her finger, Elle opened the box containing the plug she'd bought. Inside, lying on a bed of faux-velvet fabric, was a glass plug, roughly the shape of the spade from a deck of cards. Lifting it out, she wrapped her fingers around the widest section. The tip of her middle finger just managed to touch her thumb. She'd been surprised by its size when it arrived two days earlier. She thought she'd estimated the size quite well when she ordered it, going for something reasonable for an anal virgin. Now, holding it in her palm and glancing over at Jack's tight hole, she wasn't so sure.

Laying the plug back down, she lifted the small bottle of lube that lay beside it. The cap popped open with a satisfying click and she squirted a glob onto the tip of her index finger.

"Oooohooohooh that's cold!" Jack gasped when she returned the finger to his backside. He managed to resist pulling away though as Elle slowly smeared the clear, viscous gel over his hole. Lifting her finger off slightly, she squeezed another large drop of lube directly onto the centre of his ring, watching as it slowly slid down towards his balls. As it trickled down to the top of his sack, she scooped it back up to his anus and rubbed it over the creases of skin around the tiny hole. Satisfied that he was sufficiently lubricated, she pressed the tip of her index finger gently, but steadily, against his hole. Catching him unawares, it sank straight in to the second knuckle.

"Mmmmm," Jack moaned sharply at the sudden intrusion, arching his back and pressing his chest into the pillows. When he relaxed again, Elle pushed her finger in the rest of the way. She held it there for a few seconds for him to get used to it before slowly withdrawing all the way back out. Scooping up some of the lube dripping down towards his balls, she smoothly slid all the way back in. She repeated this process a few times until all of the lube that was previously on the outside of his asshole had been pushed inside him, coating his insides.

Picking up the bottle again, she squirted more of the thick fluid onto his slick hole and swiftly fed it into him with her finger. When she withdrew her index finger again, she lined her middle finger up alongside and, without skipping a beat, pressed both digits in to the hilt. Jack emitted a whimper as he felt his hole, only just used to a single penetrating finger, suddenly stretched an additional finger's width. Elle held both fingers deeply embedded inside him and felt his hole trying vainly to close around them. Jack's now rock hard cock throbbed in time with each contraction, spikes of pleasure expanding through his groin from somewhere inside his ass. As she slowly withdrew her fingers, he felt them graze firmly over some mysterious origin point inside him, sending a glorious wave of sensation through his body. He could feel it in his toes.

For the next few minutes Elle continued working her fingers in and out of Jack's slick hole, twisting them around, curling them forwards and spreading them apart, attempting to prepare him for the thickness of the plug. When she no longer felt the ring of muscles contracting around her two fingers, she decided he was ready.

Picking up the plug, she coated it in the residual lube covering her fingers before squirting a large fresh dollop out of the bottle onto the tip. Before it could slip down off the cool glass, she placed the point against Jack's sphincter, which had swiftly clamped shut with the removal of her fingers.

Jack flinched at the sudden coolness. He felt an emptiness in his chest as his nerves, which had calmed as he grew used to Elle's fingers, returned to high voltage. As the tip penetrated him slowly he was struck by how different it felt to her finger, more solid, unyielding. He was overcome by an urge to grab his dig, but he didn't dare remove his hands from his backside. He forced himself to ignore the temptation, focussing instead on his hole as it was slowly violated.

Elle twisted the plug back and forth as it slowly sank deeper, watching as his sphincter stretched around the steadily increasing diameter. When it was about halfway in, opening him to roughly the width of her two fingers, she stopped and held the plug in place, giving him a brief chance to rest and savour the sensation. Jack whimpered when she resumed and the plug began to stretch his anus further than it had ever been before. It began to sting slightly, like the Chinese burns his brother had given him on his wrist when he was little.

"Nearly there," said Elle.

There was about a centimetre more to go before the largest diameter of the plug would reach his hole and she found she had to apply increasingly significant pressure as his sphincter muscles fought hard the incursion.

"Relax Jack," she instructed, when the she found she couldn't press it any further, "push out like you're on the toilet."

How's pretending I'm taking a shit going to help?! Jack thought, grimacing against the unrelenting pressure against his anus, desperate to clamp itself to its usual sealed state. He tried to relax the muscle, but couldn't. It seemed to no longer be under his control. Taking a deep breath, he stopped trying to ease the grip of his sphincter and instead bore down as if he were trying to expel, rather than give access to, the thick plug.

"Nnnnngggg," Jack grunted when the plug shifted suddenly and the thickest section popped through his ring. Immediately, his hole clamped down, pulling the plug the rest of the way in until he could feel the round base held firmly against his ass. A surge of pleasure quickly overwhelmed the sharp stinging pain of his hole stretching to its limits. He closed his eyes tight as his hole constricted repeatedly and uncontrollably around the narrow stem, pulling the plug further into him and rubbing the bulbous mass against his prostate, swollen with arousal. He could feel spurts of precum pulsing out of his cock into the sheets with each constriction. Realising he'd let go of his backside, he quickly released the sheets from his balled fists and reached back to separate his cheeks once again.

The slippery plug was yanked from Elle's grasp by Jack's closing sphincter. When he recovered from the initial shock and pulled his cheeks apart again she grasped the end and slowly withdrew the plug, holding it still when his hole was stretched around the thickest section. When she let go, she marvelled at the way it swiftly reseated itself against his sphincter. She also noticed the thick pearl of precum that oozed from his cock head onto the sheets below. She repeated the action, enjoying the noises he made as his hole was stretched again and again around the thickest section only to suck it smoothly back inside when she let go.

"How's that?" she asked, releasing the plug at last and tapping her finger firmly against the plug so that they could both hear her fingernail against the solid glass.

Taking a gamble that he could release his cheeks, Jack replied, "It's good actually."

Lifted himself off of his chest so that he was kneeling upright, he reaching back between his legs, he ran his finger over the plug, the soft touch of his fingers magnified through the glass and into his stretched anus, which clamped down involuntarily, pressing the plug firmly against his prostate.

"Really good actually," he gasped. "Your turn now?"

"Where do you want me?" Elle asked as Jack slid gingerly off the bed.

"On your back," he answered, retrieving a shoebox sized parcel from the drawer beneath the bed. He set it down on the sheets beside Elle as she moved into position. "Perfect," he said when she settled down, "now put this on."

Something landed softly on her stomach. Picking it up she recognised the blindfold she'd made him wear the week before. Grinning, she slipped the strap over her head and pulled the smooth pads down over her eyes.

The mattress sagged as Jack moved across it towards her. She felt his warm hands slip beneath both of her knees and lift them up off the mattress. Her breath caught in her chest as he swiftly spread her legs and pressed her knees back towards her head until her bum began to lift off the mattress.

"Hold yourself like that with your hands behind your knees," he instructed, just when she felt she could fold no more. She could feel the cool air on her exposed pussy and asshole as she slid her hands behind her knees and took up the weight of her legs. In this position, she realised, Jack was free to do whatever he wanted between her legs.

Leaning over to grab the box, Jack felt the plug in his hole shift, sending a stab of pleasure through his groin to the very tip of his dick. He quickly opened the box and withdrew a small, black plug from within. Made of what he assumed was some kind of rubber, it looked just like any other butt plug he'd seen before, tapering from a small rounded tip up to a slightly wider, but still rather thin, girth before narrowing sharply to a short stem that ended in a wide round base. Extending out from the base, however, was a short length of black tube ending in a squeeze bulb that reminded Jack of the cuff doctors use to measure blood pressure. Picking up the bottle of lube from the bedside table, he returned to Elle and settled into position between her obscenely spread legs.

As he took in the sight of her naked holes, his mind's eye filled with the memory of plunging his tongue into the depths of her anus and of his hard cock sliding slowly into her ass. Leaning forwards, he planted a kiss on her sphincter and, before it could clamp tightly in reaction, pierced into her with his tongue. He was rewarded with a sharp intake of breath at the top of the bed.

Sitting back up after tonguing her hole for a few more seconds, he squirted a healthy dose of slimy lubricant over the small plug and positioned it against her hole, shining with his saliva. In a single, smooth motion he slid the plug all the way inside her, registering only the slightest resistance as the slightly thinker portion passed through her ring.

Elle was caught unawares by the plug's entry, expecting at least some sort of warmup in addition to the brief tonguing she'd received. Now that she felt the wide base of the plug resting against her anus, she felt slightly underwhelmed. Clearly Jack had gone the opposite route to her and bought a very small plug. She squeezed her muscles around the plug, trying to see if she could coax some sort of pleasure from the slim invader, which was pulling and shifting slightly as Jack toyed with it.

Lifting the bulb off the bed, Jack pulled the tubing taut and tugged gently on it, watching as the plug began to pull out of Elle's anus. He released the tension before it popped out entirely and reached forward to gently push it back inside her. Settling the tennis ball sized bulb comfortably in his palm, he wrapped his fingers around the smooth rubber and squeezed it tightly, sending the air inside down along the hollow tubing and into the plug. He heard the hiss of air passing through a valve as the bulb quickly re-inflated. When it was full again he gave it another sharp squeeze.

Elle nearly let go of her knees. Did it just get bigger?! she thought in confusion as she felt the plug shift and heard a soft hissing come from somewhere down the bed. When the sound stopped the plug shifted again and this time she definitely felt it grow, only a fraction, but enough to increase the pressure against her sphincter and confirm her suspicions.

Jack pumped the bulb three more times in quick succession, expanding the plug until the stem, which he could just see emerging from her now stretched ring, was roughly as big around as his rapidly stiffening cock. This of course meant that the part of the plug inside her was substantially larger. When he had tested the plug out earlier in the week he had managed to inflate it to the size of a party balloon. He wondered how big it was inside her right now.

Where earlier the plug had slid easily out of her ass, when he now pulled on the base he felt strong resistance and could see the tight ring of muscle being pulled outwards, unable to stretch around the bulbous plug on the other side. Holding the plug in place, stretching her anus wide, he gave the bulb two more squeezes, watching as her ring stretched visibly around the expanding rubber. Pulling hard on the base of the plug, he confirmed that there was no way it was coming out without releasing the air inside first. He unscrewed the tubing from the base, locking the air inside with no way to escape without the release valve on the pump.

Elle was breathless. Her ass felt completely full and her anus was stretched so far it was unable to clamp down even a fraction, though that didn't stop it from trying. Over and over again the strained muscle attempted to close itself, fighting furiously against being held so wide open. Remembering her advice to Jack, she bore down, trying to push the plug out, but it wouldn't budge a millimetre.

How big is this thing? she thought, panic rising.

She felt no pain, even in her stretched anus, only an incredible fullness. She gasped when Jack pulled hard on the base, feeling her asshole pulling outwards, unable to stretch any further around the ballooned plug inside her. She couldn't imagine what it must look like.

"Well, that's not going anywhere," Jack said, tugging the plug sharply a couple of times as if to demonstrate.

"What now?" Elle asked breathlessly, still holding her legs.

"Now I'm going to fuck you. Hard."

Jack let go of the base of the plug buried in Elle's ass. With the tube disconnected, there was no way for the air he pumped inside to escape. It was stuck inside her until he released her. The thought thrilled him.

He shuffled closer between her legs, positioning the tip of his cock against the slightly open folds of her pussy, his stiff shaft just barely hiding her plug from view. The plug in his own ass declared its presence to him with every twitch of his cock as his anus clamped reflexively down on the unyielding glass stem.

Unable to restrain himself any longer, Jack pressed forward, enveloping himself in the warm, slick folds of Elle's cunt. As he slid into her, he quickly felt his cock press into, and slide over, the bulbous plug inside her ass. The effect turned the already tight grip of her vagina into a vice, clamping tighter him than he'd ever experienced before.

Elle too felt his cock making contact with the enormous plug; felt the thin, nerve-filled wall of sensitive flesh separating her cunt from her anus sandwiched between his head and the rubber balloon. She moaned as he slid into and eventually bottomed-out inside her and again as he withdrew all the way out, maddeningly slowly.

"Fuck you're tight," Jack gasped, before sliding back in to the hilt.

It was all Elle could manage to whimper, "Mmm hmm," as every nerve in her body came alight. His cock pressing into and dragging along the back of her vagina, pushing against the huge plug, was like a match striking aflame.

Jack knew this was going to be a short fuck. His spasming sphincter clenching the plug against his swollen prostate, the impossibly tight grip of Elle's cunt and the erotic knowledge that he could feel the plug in Elle's ass against his cock were working together to bring him to a rapid climax. He managed to drive deep into Elle just three more times before he tipped over the edge.

The sensation began in his toes, which curled tightly. Next he felt something akin to a tickle growing in his prostate, at the mercy of the plug pressing repeatedly into it, and radiate outwards into his balls, which retracted as close to his body as they could go, nearly disappearing inside him altogether. It was at this point that he gave up attempting to fuck any longer, accepting that the rubicon had been crossed, and pressed himself as deep into Elle as he could get, instinctively trying to bury his imminent load as close to the centre of her being as possible. Leaving his balls, the sensation travelled up into his groin, back through his now spasming prostate and along his pulsating shaft. When it reach the tip, he exploded.