Making it Happen

Story by Jeeves on SoFurry

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#17 of Kinktober 2017

A young hyena meets a woman who knows what she wants, and will not rest... or indeed let him rest, until she has achieved her wishes in abundance. <3


This story was written for Day #17 of Kinktober 2017! Today's theme is Anal, and the story was written for Tygacat3891. It contains M/F sexual acts involving consenting adults. :3

Making it Happen

As the elevator rose from the lobby to the twelfth floor, Drew checked his phone one last time to refresh himself with the details of the job ahead. The hyena smiled to himself as he read through the data provided, some about the client herself, some about what she wanted from tonight, more about what she wanted specifically from her selected consort. Him. She sounded fun. He blushed slightly as the elevator halted on the seventh floor, doors opening and revealing his suited, smiling form to the well dressed African wild dog and raccoon standing beyond.

"Going down?"

The wild dog enquired, nodding in understanding as Drew apologetically shook his head. He turned his gaze towards the woman on his arm, looking like he was about to say something to her, but paused as he caught her gaze glancing towards the hyena. The doors were already sliding shut again by this point, but at the same time as the other man noticed his partner staring at the hyena's crotch, so too did Drew. The last thing he saw was the racoon raising her eyebrows and beginning to giggle in amusement, then thankfully he was alone once more, clearing his throat bashfully and replacing his phone in his pocket for the remainder of the ride up. His hands moved to cover his crotch and the slight swelling beginning to show there within his dark slacks. Indeed the client he'd been hired to assist tonight did sound fun, and apparently his body was getting a little ahead of himself in showing how much fun he hoped he'd be sharing with her.

The foyer outside the elevator was thankfully empty as it opened up on the floor to which Drew's instructions told him to proceed, and after a brief, rapid stroll down a long corridor with doors to many suites he arrived at the number listed in his information. The hyena paused outside the door and gave himself a quick once over, touching his hair, smoothing down the fur upon his cheeks, looking his suited form up and down to make sure he was clean and presentable and no longer quite so visibly excited. He was still blushing beneath his furred features, but he hoped that either the client in question wouldn't notice, or that she would find it endearing.

Often when people purposefully requested younger men like him as today's client had, those in their first few years of service to the company and thus normally in their early twenties, they liked the shy, innocent type. Not that Drew was innocent of course, not by any stretch of the imagination considering the six months he already had under his belt working here. Still, he hoped he would be suitable for what the customer had in mind. More than suitable, actually. After all, like the vast majority of folks who worked for the company and ensured its high degree of client satisfaction, there was little more important to him than ensuring that he completed an engagement to the client's most exacting standards.

He took a deep breath to steady those last minute nerves which still always plagued him just before he met a new client, worried that he wouldn't be good enough for them, and knocked upon the door.

"Yes, who is it?"

A confident yet softly spoken voice rang out from within almost immediately, and after clearing his throat, Drew answered.

"My name is Drew, I'm with Yokubo Client Services."

That wasn't the name of the company of course, but it wouldn't do to be calling out the actual reason for his visit in a public space such as this. He heard the voice from within laugh tenderly, and then she called out once more.

"Please come in, Drew. And perhaps you could be a sweetie and put the sign on the door as you do so."

He entered as requested, immediately spotting upon the back of the door an ornate wooden hanger, not one of those cheap paper ones, with a carefully carved Do Not Disturb message engraved on both sides. With a warm chuckle he placed it on the outer handle of the door, and only then closed it behind him. Turning on his heels to face into the room at last, Drew nodded to himself. The suite's layout was familiar, much like others he had visited in the same hotel complex for past client visitations. A small lavatory to his immediate right, the living area ahead, and to the left off of that main space, a large bedroom with the bigger en-suite attached. He stepped forward into the main space of the suite, beautifully decorated, and immediately noted a few items out of place. A single wine glass, three quarters empty, upon the coffee table. Some cushions out of place upon the chairs, all tossed into a heap on one of the seats except for two at one end of the longer couch nearby. And slung over the back of that same couch, draped apparently where it had fallen with little interest taken in keeping it from creasing, a beautiful black satin cocktail gown.

"I'm in the bedroom. You're more than welcome to join me."

The voice was louder now, ringing out clearly through the bedroom door which stood ajar to the left of the room. Drew proceeded towards it, cheeks reddening as he glanced through the gap in the door and saw a pair of long legs with orange and white fur, a few segments of black stripes also visible upon them. He'd known from the information provided that the client was a tigress, so at least he was almost certainly in the right place. Gently he placed a hand on the door handle, pushed the door open, and stepped inside to take his first look at the woman awaiting him.

His eyes widened slightly as she was revealed before him, lying upon her belly on the bed, stretched out diagonally across the King size mattress above its lush, still neatly tucked sheets. He wasn't shocked by the fact that she was an older woman, her bio had been very up front about her fifty three years of age. What surprised Drew, though even as he realised his shock he felt bad for not having even considered this, was just how beautiful she was. It wasn't that she looked young for her age, quite the contrary, she definitely looked like a woman in her early fifties. But with that being said, she was utterly ravishing to behold. Her ass was plump and rounded where it rested exposed before him, tail snaking lazily back and forth above it. Her body was a little rounded and chubby, deliciously smooth in its curves, her furred form lush and vibrant in its colouration. And her face, peering back at him over one shoulder with a warm, seductive smile, was brought alive by not only that teasing grin, but also the depth of her eyes. The age, the maturity that wrinkled around their corners and yet retained a vigour that some might have thought could only fade with the passing of youth, until they met a woman like this.

The tigress rolled over, onto her back, and purred loudly as she spread her legs apart and watched Drew's reaction.

"You said your name was Drew? Is that short for Andrew?"

Drew swallowed thickly as he stared at the tigress' breasts, not the most firm, not without signs of their age, but still plump and rounded just as the rest of her, with undeniably succulent nipples raised upon each peak. He dared not look between her legs, for fear he wouldn't be able to look away again. Instead he met her gaze, feeling all of a sudden like this was his first day on the job all over again, and nodded bashfully.

"It is."

She licked her lips.

"Would you mind if I called you Andrew? I like both, and I'm sure you suit Drew perfectly, but... I have a soft spot for Andrew."

Again he nodded. She giggled, raising a hand and beckoning him forth with a teasing finger.

"Come and join me, Andrew. Take off your clothes. You won't need them, I promise."

The hyena did as he was asked once more, but now with less nervousness, beginning to feel the excitement and delight of a job he now believed was going to be not only physically fun, but immensely enjoyable overall sweep through him. The best jobs were ones where the client was at ease, ones where they were neither so shy they couldn't tell you want they wanted, nor so insistent on getting what they had paid for that they made the whole process mechanical in their need to have it exactly as they had no doubt been picturing in their head since they first thought up whatever fantasy or situation it was they were paying to have fulfilled.

Soon, barely a minute later, the hyena's suit was draped over one of the bedroom's chairs and his bare body was scrambling up onto the bed beside the tigress. She purred louder still as she regarded his erection, seven proud inches of manhood twitching before her gaze. One of her hands fell between her legs, while the other reached out to stroke Drew upon one of his arms as he laid down next to her.

"In the interests of fairness, you can call me Mary-Anne if you want. But, I do prefer Molly like my profile says. I haven't been called Mary-Anne since I was a schoolgirl."

Drew grinned.

"So, what? Five, six years ago?"

The tigress snorted with laughter, playfully tapping the hyena upon the upper arm in a mock-slap.

"If you ask me for my ID, I'm gonna ask for a refund."

Laughing back, the hyena shook his head in a wordless promise not to do so. Instead he shuffled closer to her on the bed, and murmured happily when she in turn scooted nearer to him, wrapping a leg around one of his own and rolling herself over so that she was straddling him. They kissed. It felt good. Natural. Drew moaned as he felt one of the tigress' hands reach between his legs and grope at his cock, and in return he eagerly ran his hands along her flanks and down to grope at her ass. Her eyes widened slightly as he did that, but not with discomfort or displeasure, quite the contrary in fact. They grew heavy soon after, and through their interlocked lips and tongues a deep, rumbling snarl of lust escaped the feline. She released his cock, but even as their lips parted he kept on fondling and squeezing her ass, grinning as she threw back her head and grunted in excitement.

Some clients would have spent half an hour telling Drew why they wanted what they wanted. How they had come to realise that they wanted it, and how long it had taken them to summon up the courage or save up the cash to secure the services of someone like him to get it done for them. Molly was not that kind of client though, and while he would happily have listened to anything she had to say, the hyena was quite honestly glad of that fact. Sure, he was paid to be here for a specific purpose, and yes Molly was effectively his boss for the remainder of the evening and the night beyond. But they didn't need to talk about that. They didn't need to discuss and clarify what the tigress wanted, as that was blatantly obvious.

"Fuck me."

Molly tore herself away from Drew and crawled across the bed, shrieking with laughter as the hyena grabbed her by one ankle and dragged her back towards him, pouncing upon her trembling form and grinding his hard cock against the cheeks of her ass. He kissed her on the back of the neck as she shuddered and writhed in bliss, but let her loose even though he suspected a part of her wouldn't have minded if he had tried to do exactly what she wanted him to even without prior preparation. Sure enough though once she was able to crawl over to the bedside cabinet the tigress revealed a not so small plastic bottle she had obviously purposefully placed there. Drew crawled up to join her at the upper portion of the large bed, and he grinned as she blushed and closed the drawer, something long, slender and metallic sliding out of view. He made a mental note to return to that drawer later, but for now respected the trembling tigress' privacy as she pushed the bottle of water based lubricant into his hands.

Her eyes stared hungrily into his, and she growled those same two words with savage longing as she rolled onto her belly once again.

"Fuck me."

Of course, Drew obeyed. He did so correctly though, not wanting to rush things if that would make the result any less enjoyable for this incredibly eager woman. First he poured a little of the lubricant over two of the fingers on his right hand, grinning as Molly watched him, breath ragged and eyes wide. She purred and moaned hungrily as he shifted position slightly to give his hand the best angle of entry, spreading her legs wide open once more and thrusting her hips up and backward to present him with an even more accessible target. He used his left hand to spread her cheeks apart, and Molly mewled lustfully as he pressed a single finger to her puckered entrance. It slipped in with surprising ease even considering the lubrication, and after less than ten seconds, raising an eyebrow playfully as Molly gasped and moaned and looked back at him, he added the other finger too. Her moans grew louder, but while there was definitely a greater degree of tightness with the second digit added it still didn't take long for Molly's ass to take the whole thing.

Soon Drew's fingers were moving in and out of her, giving Molly a taste of what she'd asked for as he teased his digits against her inner walls and gauged from her reaction what he would do once it was his cock rather than a portion of his hand pressing into her. He blushed as she mewled and hissed in wild elation, her hands clawing at the sheets and pillows beneath her, her face thrown back in ragged, strained cries half the time and buried in the bedding the rest, letting loose even louder snarls and grunts of desire. In the months he'd been working for the company Drew didn't think he'd seen anyone, man or woman, this worked up by anal stimulation alone. And to think that this was only his test, only a tease for what was yet to come.

He threw himself down over Molly's back, and in a calculated, emboldened gesture that walked the line for what was professionally appropriate according to the rules of the company, he whispered to her a question that went beyond the boundaries of the information she had volunteered to him in her profile. Again his cock was rubbing up and down between the cheeks of her ass as he did so, and again he felt her thrashing, grunting, whimpering beneath him with every motion of his throbbing shaft.

"You prepared for me, didn't you? You've been waiting for this... waiting for me for quite a while, haven't you?"

The ease with which his fingers had entered her. The vibrator in her nightstand. It was an easy leap to make, and one that paid off as Drew pulled back and grasped for the bottle of lube once more, drizzling a more liberal quantity over his hand before wrapping it around his cock, then pouring a little more of the cool liquid over the trembling, fluffy cheeks of the tigress' rump. Molly growled once more, and as she turned her head to face Drew once more she trusted him with something she hadn't previously shared on her profile. A fact that didn't change anything about how he felt for her, except perhaps to make him even more glad to be trusted with tonight's task. But one which most definitely informed how he would proceed with things from this point onward.

"I've been waiting f-for this for more than five years. From the day I decided to break out of my shell and start living. Start exploring. Experiencing things rather than the same humdrum life I'd been living for the last forty eight. But... of all the things I've shared with others since then. All the new experiences, the new feelings and places and people, do you know what I've not been able to find?"

Drew shuddered slightly as the tigress ground her now lubricated ass-cheeks up against his glistening, slick shaft. He licked his lips.

"A man who likes your ass the way you want them to? The way I like your ass?"

Molly moaned in obvious delight at that comment, nodding eagerly.

"I've had lovers who'd spank me. Who'd grope me. Who'd talk about taking me back there. B-but... when the time came, they always went to the same spot. Always left me wanting in that way. So, I'm doing what I have to do to get what I want. I'm making it happen for myself."

The hyena grinned toothily, shaking his head as he pulled his hips back just enough to wrap one hand around the base of his cock, guiding it more directly between the slick, lubed up cheeks of the older woman's rear.

"Actually, you're not any-more. You've done your part. What you needed to do. Now, Molly... now it's my turn to make it happen for you. And... I hope you don't mind me saying so, but... god, I'm so fucking glad to have the chance."

He saw the tigress' face flush, her eyes drift downward in bashful joy for the first time since he'd set his own eyes upon her. He saw her mouth open, and though she paused for a moment, Drew knew exactly what she was about to say. What she was about to beg him to do, as she had done twice already.

He growled. He hunched himself down over her, and with his hand only slipping away from his cock once the head was already spreading Molly's pucker and pressing into the suddenly wide-eyed, shaking, desperately grunting tigress, he never gave her the chance to beg him to fuck her that third time. Drew pressed his cock into the tiger's virgin ass, and began to press deep inside of her with tender, reassuring kisses to the back of her neck and shoulders even as her hands and feet drummed at the bedding below, and she began to cry out in shameless, overjoyed elation. He pressed inward slowly, but not too slow knowing that most likely there had been a vibrator just a fraction smaller than his own cock pressed into that same orifice just hours before, judging by how ready she was for his entry. The hyena laid his body out more and more flat against the tigress' own as his shaft drove itself deeper, and as her cries and gasps of pleasure grew all the more strained and giddy as she felt herself being filled with living, throbbing flesh between her buttocks, it was all too easy for Drew to reach a point where he found himself with his hips pressed forward tight to her backside, hilted within her as best he could from their current angle.

There he lay. There the two of them lay together for some time. Occasionally Drew would thrust against the older woman's body while already hilted inside her, just to let her feel his cock flex and strain that fraction of an inch deeper still. Much of the time however even that was unnecessary. Just feeling his hard cock inside her, spreading her open, filling her as she had never been filled before, it was all Molly had ever craved. Every grunt, every gasp and moan she let slip betrayed that fact even before she began to speak between fevered, giddy breaths.

"O-ohh. You're in me. You're fucking me. M-my ass. My... aaahh... so full. I can feel it. Feel you. Oh. Ohh, Andrew. I... I never thought I'd feel this way again. Feeling something, f-feeling sex for the first time in thirty years."

Drew grinned as he nibbled on the back of the tigress' neck. He knew what she meant by that last comment, a new kind of sex. But given the way she'd worded it, he couldn't help but tease.

"The first in thirty years? God, I'm surprised you let me get through the door."

She began to giggle, only for that wonderful sound to crack into a fresh shriek of pleasure as the hyena drew a few inches back from within the tigress' ass and pressed himself rather firmly back in again.

"Aaa-aaaaaahh... oh. Oh, Jesus. How did I not think to try this sooner? T-this feels so... Andrew, please. I know you're trying to let me savour it, a-and... thank you. But..."

Her voice trailed off. She knew just as well as Drew himself that she didn't need to say it. Sure enough the hyena's hips began to pull back once more, then drive back down against her body, only to repeat the motion. He began to thrust more regularly. To rise up onto his forearms and apply greater leverage and force on the lower half of his body. He gave Molly what she wanted, what she had been waiting for. And to the hyena's absolute joy, not to mention his pleasure as her tight but well lubricated, accommodation ass clenched around his cock, she so obviously loved it.

For more than ten minutes they slowly but passionately rutted in that same position, the more experienced and yet in this case virgin woman half fighting to retain control over her senses and relish every moment of the act while a different part of her begged to be set loose and to let the sensations consume her. She wriggled and writhed beneath Andrew's agile younger body, clawing and biting at the sheets, at the pillow she pulled under her head and neck for support. She mewled and moaned while the hyena's hands caressed her plump body, and she finally began to snarl, to roar in shameless and utterly unabashed lust when as Andrew felt himself drawing closer to the point of his own orgasm he tucked his hands down underneath the tigress, inching his way forward until he had the fingers of his left paw nestled tenderly against the curve of her pubis, reaching down until those same digits began to grind and caress at the swollen, already damp and flushed nub of the woman's large, exposed clitoris.

"Nnhnhhh... i-in... Ahahhhh... Andrew! Inside!"

Molly could barely string two words together in her lust stricken state, but as she begged feverishly to the hyena while her body quaked and thrashed beneath his continued thrusts, her desired outcome was crystal clear. He grinned, grunting himself by now as he began to rut against her more rapidly. The lubrication applied to his cock to begin with had long since been replaced by his own pre-cum and the gradual loosening of her muscles through repeated and passionate stimulation, but even now as he picked up speed Andrew was careful not to push too hard, not to take this woman's inexperience for granted. He was trained for this. It was his job to ride that line between his own pleasure and the needs, the desires of his client. And thankfully, on this particular occasion, those two situations deliciously overlapped.

"Cum with me!"

The hyena growled as he drove his hips sharply down against Molly, hilting himself once again within her tight, hot, no longer virgin ass. His fingers ground feverishly against her clit, and to Drew's absolute elation he felt her back arching, her body stiffening beneath him just as the first thick ribbon of his cum lashed out deep into her backside. A strangled scream, muffled by the pillow into which her face was now buried, still echoed out through the bedroom around them, and Drew felt Molly squirming, trembling, bucking and thrashing beneath and around him as he painted her rear's inner depths with hot streaks of seed while the bedding beneath them was dampened by the equally abundant wet heat of the tigress' own absolute bliss.

For some clients, that might have been it. With their goal achieved and their high crested, they might have simply thanked Drew for his services and bid him a goodnight, or worse, without desire and arousal to drive them found themselves guilty, ushering him out with sorrow, even anger for the presumed taboo of paying someone for some form of sexual gratification. To the hyena's glee however, Molly wasn't one of those people. They lay together in the wake of that act, not moving until Drew's cock had softened to the point where he really had no choice but to pull out of the tigress' rump. They embraced. They talked. They cuddled.

And then...

"Harder! Harder!"

Breasts jiggling rather violently, Molly screamed for more as she lay upon her back, staring up at the hyena looming over her with her legs rising up the length of his torso and toes curling either side of his head. His hands gripped her thighs tightly as he pumped feverishly in and out of her, having stopped twice already to re-lubricate his cock and thus ensure he could push them both to a greater, more extreme and potently pleasurable limit than before.

"Gonna cum! O-oh... ohhhh Andrew... I... aahhhhhhhyes... I'm... yes!"

The feeling of his cock driving into her ass, the sound of his thighs clapping against her buttocks loudly and thickly, the tigress' fingers plunging feverishly into her own pussy in time with the male's rough fucking were too much for her to bear. Drew howled in delight as he watched her cum, watched hot juices erupt liberally and in violent, squirting jets from her pussy as she dragged her fingers free with a mindless shriek, clutching at her trembling chest and tweaking fiercely at her flushed, swollen nipples. He kept fucking her hard as she screamed in orgasmic rapture, but kept an eye out for her come-down so that he could slow himself accordingly. Her wild eyes met with his before the hyena could even begin to do so though.

"D-don't stop."

She snarled at him in pure ecstasy, her feet hooking around the back of his head and pulling him forward as her eyes bulged in a frenzied plea.

"Don't stop... m-mhhhh... make me... ah! Ah! Again."

It was hours later before they were done, and even then, done was a relative term.

Both of their bodies were dripping wet, and the walls of the shower cubicle was still steamed up from the recently ceased flow of hot water as the older woman blushed and giggled, spreading her own buttocks apart with soft gasps as Drew knelt behind her, gently applying soothing lotion to her pucker and indeed the cheeks themselves, all rather sore from the unaccustomed amount of use they had faced.

"Ohh... o-oh... that feels nice. Mmh. God, I wish I could say that I wanted more. But, I think if you tried to fuck me again, e-even if... even if you used your tongue again, it'd be too much."

Drew chuckled softly, slightly proving Molly's point as he leaned forward and planted a kiss on one damp, furred cheek of her rear only for the tigress to gasp at how sensitive her posterior had become.

"That's okay. If I've finished what I came here to do for you, so long as you're happy, so am I."

Molly purred deeply, but her eyes were not quite as bright and joyous as normal as she looked back over her shoulder and down at the virile younger man.

"I'm happy. S-so happy, Andrew. I just... I booked you until morning. I wish I could have been able to last for every minute of it."

The hyena remained silent for a few moments, again counting the technical rules of his employers against what made sense in this individual situation. He smiled after a little more consideration.

"Like you said, you did book and pay for me until morning. And, I'd hate for you to be short changed on the refund for the hours we might miss if I left now. Technically speaking, I'm only supposed to do for you what you signed for. It... it could leave me open to liability if I did things to you that weren't down in the contract, or if you did those things to me. But..."

He saw the spark come back into Molly's eyes.

"B-but?"

Drew rose to his feet, running his still slightly glistening, lotion coated hands up the lengths of her legs, her hips, over her wonderful plump belly before turning Molly gently on the spot to face him.

"But, I have been known to bend the rules before. To agree to some more vanilla items than those I was contracted to fulfil... for some of my favourite clients."

Molly mewled softly, happily, and looked down between their bodies to where Drew's cock stood proud and hard, waiting for her response. She beamed. She nodded. She spread her legs, reaching down between them to part the flushed lips of her pussy and graze her own ample clit with her thumb.

The tigress moaned louder, albeit muffled, as Drew stepped closer and kissed her. As he wrapped his arms around her, and for the first time that night felt her free hand guiding his cock not to her ass, but to the opening of her as yet still eager and receptive pussy. She gasped as her tender ass pressed up against the glass wall of the shower along with the rest of her, but that slight discomfort was more than offset by pleasure mere moments later when the hyena began to push himself into her, rising up on the tips of his toes to drive himself deeper into the larger, older woman.

"All night..."

The tigress purred joyously between breaths as she embraced the male and began to rock against him as he humped her, their eyes peering giddily into one another as they made out with deep, languid passion.

"Stay with me, i-in me, all night."

Drew growled and nodded at this wonderful woman, this client with whom he wordlessly prayed he would get to have a second meeting, lest he be forced to risk the ultimate workplace infraction of asking her for her number off the clock.

"I will, Molly. I... ah, I swear."

The hyena murmured to the beautiful tigress, trembling as he felt her hot pussy milking his cock, different, but no less intense and wonderful than feeling her tight, well lubed backside locked around him.

"And who knows. By the time morning comes, i-if... if we're lucky, if we're conscious? Your ass might be ready for one more round."

Together, lips locking once again, the two lovers moaned loudly. The wording of that most recent comment from Drew wasn't lost on either one of them, and though they didn't mention it, it drove them wild as they each wordlessly acknowledged and revelled in its intent.

One more round. One more. Not one last or one final round. One more.

And one of many, many they both hoped would be soon to come.

By Jeeves

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