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.
