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Booking an Interview

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Booking an Interview
-by Drace Domino

As the elevator doors slid closed, Cookie Booker turned her head to face the young woman that had made a last-second dive to join her. Underneath the critical and piercing gaze of the sophisticated older woman the already on-edge Black Sheep tensed, one hand tightening around the handle of the toolbox while the other slipped into her pocket. She had been trained so well by the V.I.L.E. teachers that escaping wasn’t going to be much of an issue, yet being face to face with a woman she had studied since she was a child was still an unnerving experience. She had lobbed dozens of water balloons at Cookie and the cleaners over the years, yet never had she been within more than a few feet of her. Now, as the elevator music played and they began to slowly descend, Black Sheep found herself fidgeting in discomfort as the much older woman observed her.

“ how are you, ma’am?” Black Sheep murmured, shuffling her feet back and forth and doing her best to focus on the task at hand. Within Cookie’s crip was the encrypted hard drive she was after - the real prize of her planned escape from the Isle of V.I.L.E. If she could just distract Cookie long enough to make the switch with her toolbox, she could get to a ship and make a break for it. She was so close to being free, so close to being away from this horrible place, so close close to a woman that towered over her, and now moved a slow hand toward the elevator controls.

Cookie Booker said nothing as she revealed a tiny disc within her palm and pressed it to the elevator’s face. There was a sudden spark of electricity and then an intense humming sound, and Black Sheep found herself having to brace her knees as the elevator came to a sudden and complete stop. Cookie remained silent as she turned towards the young thief and allowed a slender brow to arch from behind the lenses of her sophisticated glasses, only speaking once the elevator remained completely still and the music came to a halt.

“A little espionage trick, dear.” She idly gestured towards the disc she had pressed to the elevator control panel, which hummed softly and remained firmly locked into place. “The security camera is looping and the elevator has stopped. It’s just the two of us now, young lady, and you can stop pretending.”

Black Sheep’s eyes opened a bit wider, and she took a half-step back until her heels hit the wall of the elevator. She hadn’t tucked any weapons into her jumpsuit save for the toolbox gripped tight in her fist, but she was nearly ready to swing it as Cookie Booker confronted her. She had already taken Mime Bomb out of the picture to make her escape a smooth one, and if Cookie thought she’d go easy on her because of her age, she couldn’t of been more wrong. As it turned out, Black Sheep didn’t even have a chance to swing before Cookie continued, pulling the hard drive forward and dangling it before the young woman’s face.

“I was wondering when you’d realize these petty criminals are holding you back, dear.” She offered, her sharp features framed by gray and white hair sculpted into a perfect form around her head. As she spoke the beauty mark against her cheek rose and fell as a point of focus, and her crimson lips played a knowing smile as she regarded the younger woman. Her tone was teasing yet far from hostile, the voice of a woman that knew better than Black Sheep not because of her age, but because of her experiences. “Let me were planning to bait and switch for this before making a break for the docks? Bold, Black Sheep, even for you. I’m impressed.”

For the first time since stepping onto the elevator, Black Sheep allowed her guard to drop and a relaxed breath to escape her throat. She could feel her muscles untense as Cookie held the hard drive out, and a small smile even formed at the corner of her lips. Maybe this old career criminal wasn’t the hard case she had always pegged her to be - maybe all those years of throwing water balloons and giggling as she ran had built a soft spot in Cookie’s heart for her. Black Sheep cautioned one more glance at the espionage tool rerouting the elevator’s power before turning back to the older woman, stretching a hand out to reach for the hard drive.

“Whew, you scared me!” She admitted with a blush moving across her cheeks. “Ms. Booker, I don’t know why you’re helping me, but thank you so muc--”

She realized, as Cookie pulled the hard drive just away from her grasp, that this assistance wasn’t going to be free. She was a business woman, after all, and as Black Sheep’s fingers passed through open air the older woman’s beauty mark lifted along with her grin. She narrowed her eyes in a sinister fashion as she made a vague gesture to her spy device, and when her voice slipped forward again it was mysterious, alluring, and almost desperately self-serving.

“I’ll let you make the switch. Even tie me up in a closet somewhere to make it seem believable and give you a head start.” It was a generous offer, but her recompense wasn’t up for negotiation. “My device should last twenty more minutes. If you want my’re going to make fifteen of them memorable.”

The way the words dripped from her tongue and the predatory fashion in which she gazed up and down the eighteen year old’s figure said it all. A slow lick of Cookie’s tongue across her lips made it quite clear she had designs on the young thief - designs that she finally had an opportunity to act upon. And though Black Sheep found herself squirming underneath Cookie’s gaze, although the V.I.L.E. account was easily thirty years her senior, not for a second did she think of refusing.

The toolbox clattered to the floor, and Black Sheep’s hands moved up to pinch the zipper of her suit and begin pulling it down. As the inches upon inches of tanned teenage flesh became exposed, she took a half-step forward before dropping down to her knees right there in the center of the elevator. There was no hesitation, not a trace of pause in her acceptance of the offer. Merely a hot young thief ready to whore herself out for her freedom and a playful smile forming a confident whisper.

“I’ll give you all twenty, and you can owe me one.”


The taste of mature pussy landed on Black Sheep’s tongue - the first one she ever had. With Cookie’s stylish pants now bunched around her ankles the younger woman was free to press hands to the outsides of her thighs, leaning forward and nestling her face neatly below the career criminal’s slit. Her nose was pressed against the sensitive hood of the older woman and Black Sheep didn’t hesitate to enjoy the aroma, drawing in long, deep, satisfied breaths as she explored something altogether new. It seemed like even though she was escaping from V.I.L.E. island that very evening, there was one more lesson she had to last lock that she needed to learn the skills to pick. Thankfully, it seemed like Cookie Booker had a much more patient regard than most of the other teachers.

“That’s it. Lovely work, young lady.” Cookie gave a groan of pleasure as she lowered a hand to Black Sheep’s head, letting her fingers thread through the locks of cocoa hair and twist into a gentle grip. She didn’t usher her hips forward any harder than she thought the younger woman would be able to handle, and allowed her to learn her way around a pussy with that warm, wiggling tongue. “Slip out of your outfit while you work. You must present a woman a show while you service her, you know.”

“...yes, ma’am.” Black Sheep murmured with a smile tugging at the corners of her lips, and she did exactly as she was told. She slithered the rest of the way out of her uniform, peeling the top away from her shoulders and casting it aside, and then working her way free of the tight fitting pants that had been hugging her curves. Before long Black Sheep was kneeling there in the elevator wearing nothing but her boots and a blush that ran from her cheeks to her chest, and all the while she remained hard at work on the prize before her. Once she was bare Black Sheep took Cookie’s words to heart and endeavored to give her the requested show, palms moving across a pair of perky teenage breasts before gliding down her slender stomach and to her own slit. As she made it a point to emphasize how she rolled her hips forward into her own touch Black Sheep locked her lips around Cookie’s hood, curling her tongue and giving a sudden series of flicks to keep the older woman at the height of her pleasure.

She was a fast learner, and not even the demure expression of the V.I.L.E. accountant could hide how impressed she was. Through the lenses of her red-framed glasses and looking perfectly poised and pleased, Cookie savored the sight of that young face nestled between her thighs and working so very, very hard. To think, that unruly little brat that had harassed her for years could be not only one of V.I.L.E.’s most talented agents, but an eager slice of pleasure that was free to be enjoyed. Cookie gave a soft moan as she rolled her hips from side to side, letting Black Sheep’s tongue past across her pussy in a laced pattern. With her grip on the girl’s hair intensifying she finally pushed her hips forward and shoved Black Sheep’s head down, effectively pressing her hood against the center of the girl’s forehead and then slooooowly dragging down, slathering her in the dense, scented nectar of a mature woman driven to hunger.

“ very, very lovely.” The words dripped from Cookie’s tongue like honey, and she cast a brief glance towards her spy device that kept them in perfect privacy. They had nearly spent a quarter of their time together, and the older woman already knew that it wasn’t going to be nearly enough. To properly exhaust the fun she could have with a girl like this, there likely wasn’t enough elevators on the entirety of the Isle of V.I.L.E. With that thought in mind, Cookie turned her gaze to Black Sheep and spoke in a voice that was low and scandalous, though playful as the girl’s tongue returned to pepper her folds with affection. “When you make your grand escape, dear, you should stop by the communication office where I left my coat and hat. Take them with you - it might afford you a disguise while you get away.”

“T-Thank you, ma’am.” Black Sheep was almost endlessly respectful, kneeling there naked and subservient to the mature woman that had so shamelessly taken advantage of her situation. She had a single hand pressed against her teenage pussy and was rocking back and forth into that soft touch, and she continued to whisper even as she turned her head from side to side to offer kisses to Cookie’s pale, goosebumped thighs. “I appreciate your help.”

“It’s not charity, dear. It’s an interview.” Cookie remarked in coy fashion, and moved both hands to slink behind Black Sheep’s head. Slowly, she started to lift a leg until she was able to hitch her foot to the handrail that sat waist-high in the elevator, and once she did it gave her the leverage to loom all the harder over the younger woman. By this point the face-wide grinds of her slit across Black Sheep were the norm - even if it didn’t bring her the same level of profound stimulation as the girl’s tongue, there was something viscerally enjoyable about slathering her in the mature essence of an older woman’s aroused pussy. Black Sheep would still be tasting her when she was on her escape boat, and that knowledge made Cookie writhe with delight. “In one of the pockets of my jacket you’ll find my extra phone. I trust you’ll use it to get in touch with me when you’ve landed in your new life. I can be...quite generous and accommodating to young women looking to start a career for themselves.”

Black Sheep was smiling all the wider now, and she eagerly nodded in a fashion that coated her all the more heavily in the other woman’s scent. With that agreement on the table the younger woman slid her hands up behind Cookie’s thighs and sunk them into the surprisingly firm rump she possessed, one hand sporting a set of fingers that were glistening in her own nectar. From there, Black Sheep focused on her task and carrying out her end of the bargain, her tongue weaving hungrily back and forth and her lips pursing and kissing at every sensitive bit of flesh offered to her. She was determined to satisfy every last desire that Cookie had - of all the tests she had faced at the Isle of V.I.L.E., she never would have imagined her most important one would be a pop pussy quiz in an elevator.

Black Sheep was good at everything she tried, and eating out an older woman was no exception. As Cookie loomed a leg over her and continued a slow grind across the teenager’s face, it didn’t take long before she felt her heart beginning to race and pleasure dancing across what felt like every last part of her. She sported goosebumps across her arms and a blush over her cheeks that she made sure to hide from the student - leaning her head back and staring up at the elevator to disguise the bliss she wore. After all, she didn’t want Black Sheep to think she was too good, otherwise she’d never be motivated to get better! What Cookie couldn’t hide was the impending climax that was rushing through her, and she revealed the joy through the fierce grip she held on Black Sheep’s hair and the spasming gasps of air that escaped her throat. She whimpered, she unleashed a muffled moan, and when her pleasure could finally grow no higher she struck a moment of glorious, desperate release.

Black Sheep’s eyes went wide as she sensed it, and her tongue eased itself just underneath Cookie’s folds, her nose taking on the task of rubbing back and forth across her sensitive, shivering hood. She was smart enough to know just how sensitive things could be in the seconds after release and so her contact was kept delicate and tender - once more looking at the prize before her as another lock that had been expertly picked by a skilled touch. As Cookie’s climax shook through her and Black Sheep was treated to the dense scent and nectar of woman thirty years her senior, the young thief savored it. The sounds, the smells, the heat, the tense grip in her was no surprise her hands had moved right back to her pussy some time ago, and her fingers were hard at work.

It was a shame they wouldn’t have time for much else - Black Sheep already knew it was going to be a hell of a frustrating escape until she managed to get on the boat and stuff a hand down the front of her pants.

“...y-yes, young lady, that was magnificent.” The calm voice of the older woman finally spoke, and Cookie lowered her leg once more to resume her dignified stance. She didn’t draw her pants back up because it was hardly her duty to do so - she waited patiently as the naked Black Sheep grasped her garment by the waistband and pulled it back into place. Once she was dressed once more Cookie guided Black Sheep up to her feet, and she took the time to give the naked teenager a once-over with a thoughtful, pleased eye.

Every inch of Black Sheep’s tanned skin was a delight, and one that Cookie would take profound pleasure in exploring at a more suitable time. For the moment, though, she pressed herself close and loomed over Black Sheep like a shadow, letting one hand slip slowly down between the moist, excited nethers of the younger woman. With one hand eased to the back of Black Sheep’s neck, Cookie gazed down at her with that look of superiority past her glasses - though unlike the teachers of V.I.L.E., it was a superiority that Black Sheep found herself more than happy to submit to. A skilled, masterful touch found its way between the younger woman’s thighs, and as Black Sheep audibly gasped from a single digit tracing the folds of her pussy, Cookie whispered in soft, teasing, but deeply appreciative words.

“I will be intensely disappointed if I don’t hear from you.” She cooed, refusing to insert that slender digit no matter how much joy it would bring Black Sheep in that moment. “I believe our professional relationship could prove...quite satisfactory for us both.”

“Y...Y-Yes, m-ma’a--” Black Sheep’s voice was cut off by the sound of the elevator music beginning once more, a clear sign that things were about to resume standard procedure. Before the elevator could begin moving and the security cameras retained their usual feed, Black Sheep pressed away from the smirking Cookie and struggled to get dressed in rapid fashion. The older woman merely held a fist around the encrypted hard drive the girl had sought and watched her stumble - spending quite a bit of time enjoying the sight of that tanned, tight, teenage ass as she bent over to swing back into her pants. Before the elevator finally began to move once more Cookie offered one last bit of advice to the girl - and seamlessly moved to stand in the exact same position she was in before her spy device gave them that moment of privacy.

“Have a care for how you tie me up for our little ploy, dear.” She advised, her crimson lips broadening to a confident smile. “I assure you, the next time we meet, I’ll be the one controlling the rope.”

Black Sheep gulped, stood up straight beside the older woman, and took a deep and intense breath - one laced with a scent she’d be enjoying for hours.

“Y-Yes, ma’am.”

The End.