Date Night

 "Are you waiting on someone?"

He looked up from his drink.  Immediately at eye-level he was presented with the most impressive cleavage he had ever seen, a pair of large gravity-defying breasts under a black silk dress, hard nipples straining against the fabric.  The v-neck plunged just lower than was fashionable, showing a brief glimpse of a red lace bra just beneath.

Staring longer than was technically polite, he dragged his gaze up to the very full lips that spoke the words, cherry red lipstick shining like hard candy. With a final burst of willpower, he eventually reached the ice-blue eyes and delicate features framed by long blonde hair. A single eyebrow arched wryly in amusement.  The lips formed words again, while he reeled from the beauty before him. "Does your mouth work too, or just your eyes?"

His mouth, at the mention, was suddenly very dry. He took a sip of whisky and attempted to string together a sentence.  "Um, yes. I mean, no. I mean, the seat is free if you'd like to join me."

"If you need more time to think about your answer I can come back later." A grin creeped across her lips as she rested a hand on a thick hip, emphasizing the contrast to the slim waist just above, in a gesture somewhere between amusement and impatience. "No," he replied, "I'm sure you can join me.  Sorry, I was just... distracted. Let me get you a drink." He raised a finger with a nod to the bartender.

She smiled in earnest this time, "that would be a good start." She sat delicately on the stool next to him, crossing her flawless, tan legs ending in a pair of black leather knee-high boots, chunky heels adding to her apparent height. As she folded her legs, the mini-dress slid up slightly, revealing the tops of nude stockings with black backseams. A red garter, matched to the hint of bra he'd caught earlier, escaped from the edge of her dress like the beginning of a promise not yet spoken.

He opened his mouth, "Hi, I'm - " is as far as he got before she lay a delicate hand on his arm, nails in a bright red lacquer matching her lips and lingerie. The bartender had silently approached and was looking meaningfully at the blonde, momentarily as stunned as John had been by her stunning elfin beauty. "Whisky, the same as him." She turned back to John, "I'm sorry, you were saying something..."

"...ah, yes, um, I'm, uh... John," he finally got out.

"Well then, I guess I'm Jane," she replied warmly, "It's a pleasure to make your acquaintance, John."  She smiled again, "Do you... come here often?"

He matched her smile with one of his own, "yes, you could say that. There aren't too many cozy bars on this side of town, and it's a quiet place to pass the time." The rattle of ice hitting a glass punctuated his statement for him. "I like to be able to hear myself think."

She absently raised a hand to her chest. "And what are you thinking about so hard this evening?" she asked, just a hint of mocking innocence slipping into the question. "Most people don't come to bars to think." His eyes followed her hand as it idly stroked one perfectly-sculpted breast.

The heat from the whisky and her closeness started to thaw his brain, "I was just thinking that I really should find some company, it's so boring drinking alone."

"Well, perhaps I can be of assistance."

They chatted for a while, numerous entendres dripping from every sentence as they jousted. After half an hour of verbal foreplay, Jane again laid a hand on his arm and looked him in the eye, "I'm going to slip to the restroom, why don't you settle the check while I freshen up? Then we can get out of here."  She said it as a statement, not a question, and John simply nodded.  She got up and turned away, wiggling her curvaceous ass and hips with every step in a swaying walk, the clicking of her boots on the stone floor in sultry rhythm of the music playing quietly in the background. He slid his card over to the bartender, making a check-mark in the air, and quickly resolved the balance due.

He'd barely finished signing his name before he heard the staccato clicking announcing her return. He watched her close the distance between them, each step setting her impressive bosom to bounce with such ferociousness that he was sure her dress at any moment would give up its vain attempt to keep her covered. By some miracle the fabric held until she made it back to the bar, and she leaned against his arm, her ample breasts squeezed against him. "Are you ready to -" he began, but she pressed a single, manicured finger to her mouth in a gesture of silence. She must have reapplied her lipstick, he thought, as her lips appeared even more brightly red, glossy, and - could it be - larger, almost swollen.

He took her arm gently, and they strode to the door. As soon as he opened the door, a sleek black car slid up to accept them into its leather embrace. She pressed against him, taking his large hand in hers and sliding it to her nylon-wrapped leg.  He caressed her thick, exposed thigh, fingers tracing upwards to outline the edge of her garter.  She made quiet appreciative noises, almost a purr, before reciprocating in placing a hand on the very-noticeable bulge growing in his pants. She paused, looking him deliberately in the eye with that same raised-eyebrow of amusement for just a moment, than leaned her head against his neck while her hand massaged him through the thin fabric.

Only a few minutes passed before the car rolled to a stop in front of a generic-looking brownstone building.  She slipped out, and leading him by the hand to the door.  Keys quickly filled the locks, and he barely remembered to close the door behind them before he wrapped her in an embrace, kissing those her plump lips.

As she gently opened her mouth, he was surprised to discover this tip of his tongue pressed against an unnaturally-smooth interior, the faint taste of rubber cutting through the memory of his whisky. Now it was his turn to fix her with a raised eyebrow and a smile, "I see you made some changes in the bathroom."  He slipped a thumb into her mouth, probing the latex sheath between her lips, pressing against her concealed tongue. She sucked gently on the finger and moaned through the rubber in response.

After a few moments, she pushed him away gently while hooking one finger in his belt. Leading him by this handle, she lured him towards a bedroom in the back of the flat.  With a flick of her wrist she managed to undo his buckle and pull the belt out of its loops in one fluid motion, casting it onto the satin sheets of the waiting bed. She moved one hand to her neck, moving her long blonde locks out of the way to indicate the long zipper which had so valiantly kept her dress together so far. He kissed gently on the exposed skin just under her ear, while slowly working the zipper down her back and past her thick ass.

She turned to face him and slipped off the silk dress, letting it drop to the floor. In doing so, she revealed her lace bra, a balconette which appeared to be several sizes too small. It just barely wrapped around the bottom of her incredible tits, leaving a gap between them and a pair of large hard nipples poking out over the top edge of the cups. A red lace g-string completed the ensemble, worn overtop of her garterbelt in the classic style.

Slipping his hands around her waist, he pulled her close as he lowered his head to kiss gently at her incredible bust, running his tongue down her cleavage. She reached a hand behind her to unfasten the clasp of the bra, as he peeled it off of her impressive breasts. Surprisingly, they didn't drop even an inch - they appeared to almost spring up higher without the tight lacy constraint. He moved his attention fully to one nipple, circling it with his tongue while sucking gently, then moving to the other.

Wrapping one hand into the hair on the back of his head, she nudged him backwards, the back of his knees pressing against the soft bed. She quickly unbuttoned his shirt, revealing his muscular physique. As he shrugged out of the sleeves, she set to work on his pants, unzipping them quickly and yanking them down to his ankles. His boxer briefs soon followed them, releasing his massive cock.  She pushed him down, sitting on the bed as she dropped to her knees in front of him, wrapping her perfect breasts around his huge member and began stroking up and down. After a few moments, she enveloped his cock in the tight sleeve in her mouth.

She worked her machinations on his manhood through the constrictive rubber, his breath coming faster and harder with every stroke.  He ran his fingers through her hair, soon grabbing a fistful before she could take him too far.  As she quickly released his cock, her lips and the attached sheath pulled away from her face, staying suck to his member. "Oops," she chirped. Her artifice revealed, she quickly peeled she sleeve off the tip of his rod, as he pulled her to her feet.  Her massive tits smothered his face as he slipped down her panties, revealing a neatly-trimmed blonde thatch sitting atop an overly-large clit and pair of thick lips outlining her pussy.  As she turned around again, she bent over fully and spread her cheeks showing yet another surprise - a ruby-red jewel sitting at the end of a metal buttplug set deep into her ass.

Not giving in to the obvious suggestion just yet, he pulled her down onto his manhood, eliciting a deep moan from somewhere primal deep inside of her. Though her opening was already dripping, it was an incredibly tight squeeze as she levered herself onto his lap - to both of them that it seemed an eternity before his whole cock slipped all the way in.  She began to rotate her hips as he clutched tightly to her hips, garterbelt sliding under his fingers as he strained to keep himself under control. He slid his hands up to cup her incredible breasts from behind, his large palms dwarfed by their massive size. John squeezed harder, tighter, pressing his fingers deeper with each thrust. Jane, meanwhile, took her clit between her fingers, massaging intensely. Pressing hard on the top with a "click," a quiet buzzing filled the room, as John felt the distinctive vibrations transmitted to the base of his cock. This had the desired effect on Jane, and she soon arched her back and leaned into him, moaning as she climaxed hard, the walls of her pussy clamping tightly onto his cock in waves of pulsations.

As her breathing slowed, she slid off and kneeled on the bed next to him. She grabbed the base of his still-hard cock and purred, "still not done?  Well, since we've already done away with some of the illusion... you're really going to want to feel this!"  She dug her nails under the base of his testicles, peeling back a well-disguised seam.  As she gently removed his real balls from their encasement, she peeled the thick, flesh-colored silicone sleeve, revealing his less-impressive but still average cock underneath, glistening with precum and lube. She slipped to her hands and knees, and reached one hand to the top of her butt plug, slipping it free with a very wet, and very unnatural-sounding, *plop*.

He kneeled behind her and lined up his very real cock with her newly-vacant hole. With some effort he was able to slide in past her very tight outer ring, and discovered her anus to be ribbed and textured inside, just like a sex toy. Surprised, it was now his turn to gasp suddenly - eliciting a giggle from Jane, "I knew you'd like this!"  The extra friction was too much to bear after the previous entertainment, and after barely a dozen strokes he exploded into her ass, groaning loudly. He collapsed onto the bed next to her and looked up into the incredibly-blue eyes.

"Mmm, that was nice," she cooed, "shall we say goodbye to John and Jane?" As she pulled away her blonde wig, revealing a very bald head underneath, he grinned and nodded, reaching just under his chiseled jaw as she worked her nails at the base of her neck.

"One."

"Two."

"Three!" they chimed in unison, each pulling away their false visages with a loud sucking noise.  Her mask shed, her average features and long brown hair emerged from under the thick silicone. Meanwhile, "John" was actually quite boyish in appearance – not young, but still with the slim features that come before middle-age sets in. "Hello Cassie," he said. "Hello, Jack," she replied, grinning.

She climbed to the edge of the bed and unzipped her boots, revealing her feet squeezed into ballet posture at a seemingly-impossible angle, the toes of the boot false padding to hide the extreme nature of her footwear which added a full eight inches to her height. "Phew, I am glad to be out of those things finally!" she said with a smile.  "Oh, you know you love it!" he retorted cheekily.  "Yes, I do, but I also am glad to have them off at the end of the night - I'm still getting used to walking en-pointe all evening!"

"Maybe next time I can be Jane," he chuckled as he peeled off his chest muscles like a t-shirt, dropping the artificial skin onto the bed, "though I can't possibly fit into the boots."

"You just want to be able to keep your hands on these tits all night," she responded, shaking her shoulders and setting them to jiggling to punctuate the statement.  She cupped one breast with both hands, and began tugging it away from her chest. It stretched and deformed until it emitted a slight ripping sound as the adhesive gradually released its grip, and she repeated the process on the other side. A pair of small yet perky real breasts emerged from underneath, each tipped with a delicate pink nipple many times smaller than the artificial silicone pair that capped the tits she now held in her hands.  She tossed them at him and laughed, "here you go!"

"Ow, those are *heavy*," he groaned.

"Wait 'til you try wearing them for a whole night!" she squeaked out between giggles.

She unfastened the straps and her garterbelt soon joined the pile of lingerie on the floor, before slipping down each stocking in turn.  Standing, she plucked at the top of her hip, and began to peel off the large pieces of thick skin-colored padding that wrapped down her thigh and along the cheek of her ass, dropping the pounds of silicone to the bed with a thump. Once again she repeated the process with the opposite side, her incredible curves slowly pulling away with that same tearing sound to reveal nearly-boyish, but still quite feminine, smooth hips. Meanwhile, Jack slipped down what appeared to be a pair of silicone, crotchless biker shorts, taking his own muscular thighs and firm ass with them. "I never get tired of watching that part," he quipped.

"Just watching?" She smirked at him, "what do you think of my new 'upgrades'?" She thrust her mound right in front of his face and gently patted her full lips below, which were glistening with lube.

He leaned forward and ran his finger along the edge, "Very impressive, I didn't think I was going to fit, this new sleeve is so tight inside you!"

"You almost didn't! I didn't expect you'd be wearing your biggest cock sheath as well! You definitely wouldn't fit in my new ass with that thing."

He smiled and slipped his finger into his mouth, "Wait, is this strawberry lube?"

"Yup, next time you should give me a lick before you get so excited."

She then peeled away the thin blonde strip of hair crowning her pussy, carefully laying the merkin on the bed so as not to let it stick to itself, and revealing her completely hairless mons. Placing one delicate foot on the bed, she then grabbed hold carefully of her swolen labia and pulled gently. As the artificial lips pulled away from the real ones beneath, her anus also began to peel back, and two long, thick, slightly-rigid tubes slowly slid out of her pussy and ass, the undulating ribs on the outside making a squelching, sucking sound and elicited a soft grunt from her with every new wave. She held up the device for him to get a closer look, "see, ribbed on both sides, for his *and* her pleasure!"

"It definitely was pleasurable, I love it when you become a living sex toy!" He gestured to the massive cock sleeve he had been wearing earlier, "do you think I should pick up something less realistic for next time as well?"

She grinned wickedly, "That might be a lot of fun."

Setting the double sheath down, she plucked at a black rubber nub sitting on top of her real clit, where it had filled out the small pouch between the top of the lips, and which wrapped down into her slit.  She slowly slipped the vibrator from inside of her, and laid it on top of the pile.

Jack smiled, "Next time you should give me the remote for it before we go out!"

Cassie grinned back, "Oh I remember what happened the last time we did that, you left me in a puddle of my own cum at that restaurant! That is *so* not fair, at least until we get you something to match."

"It's a deal."

Cassie slipped into the bathroom, briefly rinsing off and then removed her colored contact lenses, revealing her brown eyes beneath.  Jack, meanwhile, removed the caps from his teeth, replacing the perfect smile with his slightly more awkward toothy grin.  They then collapsed in bed together, and fell into a deep, and well-earned sleep.