Being Mom's Partner 2

Story by draconicon on SoFurry

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#11 of Paying Off Mom

In an effort to get a richer client, Iggy ends up finding one hell of a mistress...

Commissioned by Kacacarrotcake

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Being Mom's Partner

Part 2

For Kacacarrotcake

By Draconicon

Iggy eventually settled on something that might have once been called a suit, but had since been altered to the point of being almost unrecognizable. The whole thing was smooth, black and white, cut to his body to show off his ass a little more than it should, and it pulled in close to the crotch as well, just to show off the hint of a genital slit down there. Normally, the young stingray wouldn't have worn it for anything less than something that demanded formal clothing, but as all his other outfits were rather on the slutty side - and some were downright illegal for most public gatherings - it was his only choice.

He took an Uber this time, riding out from the house to the address his mom gave him. The app only gave him a map view, rather than a proper city view, so he didn't know where they were going. Somewhere downtown, that was all that he had.

Wonder what sort of guy this one is...

The stingray leaned back, one leg crossed over the other as he considered how this was going to go. This was supposed to be something higher class, something a little less obviously slutty. What would that mean for him?

He honestly wasn't sure. Iggy had been on the slut side of things for months now, and it meant that he was more keen to just fall to his knees and start sucking someone off than he was to actually flirt. He wasn't sure that he still knew how to flirt, now that he thought about it. Bluntness had been the better tool for getting a quick buck.

The little black book, though, reminded him of just what kind of thing he needed to be now. His mother hadn't been able to keep things going with the simple sort of easy-sex that she set up for herself, or for him. They needed something bigger, something better. They needed clients with money.

Hopefully, this worked out. Hopefully, he could still learn as he went.

The car came to a sudden halt. Realizing that there were no stoplights in the area, Iggy guessed that they'd reached their destination. He turned -

Then blinked. They were at the edge of a park rather than the usual hotel or restaurant. He looked down at his phone, double-checked that they were at the right place. They were. Trying to puzzle out what the hell he was supposed to do here, Iggy was interrupted by the driver.

"This is the place, right?" the Doberman up front asked.

"Um, yeah, I think so."

"Then you better get out."

"Little rude..."

"Look. You're obviously...working...and I don't need the cops looking at me as an accessory, got it?"

"Okay, okay, fine."

Iggy slipped out the passenger-side door, and no sooner had he closed it than the car drove off. He watched it go, shaking his head as he looked down at his phone again.

"A park...how the heck am I going to find a client in the middle of a park?"

That was the question, and his mother hadn't given him a clear answer. Was he supposed to wait until someone approached him? Was he going to have to recognize someone by their body language, guessing what they wanted from that? He hoped not; he wasn't very good at reading someone that way yet.

He turned on his heel, looking around for someone, anyone that might have been obviously looking for 'company.' There was a dog-walker going around the fountain, and the wooded park had a number of singles and couples that were taking an evening stroll, but nothing that implied someone looking for him.

Mom, is it always this hard?

Not that he could ask her. Iggy sighed, putting his phone in one pocket and pulling the little black notebook out of the other. He didn't quite remove it, just dragged it out so the black and gold showed from his pocket. If nothing else, someone that knew what the notebook meant might see it and approach him.

Guess I can get some air...

Iggy began his walk around the park, taking his time to take in the evening air. He was used to walking around looking for clients at this time of night, but it was different doing it at a public park rather than at one of the colleges or down at the bars. It was...more open, more dangerous, in some ways, but also more civilized.

As he walked around the fountain and headed down one of the wooded paths, a wolf female came around the corner. She met his eyes, then looked past him, and he paid no more attention to her than that.

That was, until she came up beside him and licked his neck. He stiffened, his eyes going wide as she slid behind him with a chuckle.

"So, you're the one that slut sent me, hmm?"

"You...you're the client?" Iggy asked.

"Potential client, boy. Potential."

I didn't expect...oh boy...

It was the first time that he had had a dominant woman interested in him other than his mother. The idea of having someone like this taking control for the night sent shivers down his spine, mostly because he had no idea how she was going to want to be served. The idea of giving her oral wasn't that bad, considering that he'd had plenty of experience with his mom's cocks, but this could get a lot weirder, very quickly.

The way that the wolf woman rubbed her hands down his sides, the way that her fingers dug into his hips, made him guess that she was a lady that preferred a strap-on, but that might be a bad guess. He just stood there, letting her examine him.

"Heh...you like to be touched, kid?"

"Um...some."

"What's the matter? Your mom told me that you had some experience?"

"More, uh, with men than with women."

"Oh-ho-ho. You're an ass boy, then?"

"I've done more of that, yeah. Um...I'm willing to learn, though."

"Cute."

Smack. He barely kept from jumping as she slapped his ass, but he did jerk forward by a few steps. She laughed at that, too.

As he rubbed his ass, he took a second look at her. The wolf woman wore a business-style blouse, a gray jacket over a white shirt, with a hint of a tie showing. Her wide hips were barely restrained by an elegant sort of skirt. Very much high-ranking business exec, and a cougar from hell considering her age.

It was kinda hot. Kinda creepy, too.

She leaned in closer, her gray-furred muzzle pressing against his nose. He didn't take a step back, didn't dare to, and he let her lift his chin with her clawed finger.

"Hmm..."

"Yes, ma'am?" he managed to say, thankfully without a squeak.

"You need better clothes."

"...Pardon?"

"I'm going to do you a favor. And then you're going to do me five of them."

"F-five?"

"I think that's fair. After all, I am going to pay you...and extensively, if you do this well."

"..."

"Come with me. You need to be dressed for this."

Iggy wasn't sure what to think as he was dragged through the park, into a limo, and then out into the brightest, most golden department store that he had ever seen. He felt like he was being pulled through a dream, and he didn't dare react to it in case his stubbornness turned it into a nightmare.

Before he knew it, the stingray had been shoved into a little box of a room, his clothes ripped off - actually ripped, torn, reduced to nothing but threads - and the door slammed shut before he could actually protest. His eyes went wide, one hand covering his crotch, but before he could say anything:

"Stay right there. I'm getting you something proper."

"I...okay."

Iggy reminded himself that he needed to impress this woman, but he was starting to think that there wasn't really a way to impress her without completely going over the lines. She'd left him naked - naked - in the middle of the changing rooms, and now he had to hope that she was actually going to help him here.

Then again, this was a friend of his mom's, so he wasn't sure why he was surprised. They were all a bit nutty.

He was just starting to feel a bit uncomfortable, the sheer strangeness wearing off and some nervousness coming back, when a pair of pants were tossed over. A pair of panties followed, with a shirt after it.

"Try those."

"What -"

"Do what I say, kid. Do what I say, and you'll be rich by the end of the night."

"Yes, ma'am."

This was definitely going further than the last few experiences he'd had. The stingray pulled the clothes down, slowly sliding them on. The panties were actually rather familiar, considering that he'd started wearing those more than boxers lately, but they were higher quality than the stuff that he had at home. They were softer than silk, and they were transparent enough for him to be able to see his cock slit through them. As he pulled them up, they were like gliding hands along his thighs and between his ass cheeks, rubbing them, squeezing them.

It was enough to give him a semi, and he blushed as he saw that in the changing room mirror, too.

"Come on, come on."

Her pushiness made him blush, too. If she was this eager out here, what was she going to be like when they were somewhere private?

Suddenly, he didn't want to know.

The shirt was tighter than the other one had been. Still one that could be buttoned-up, it molded itself to him, pushing at his limited muscles, making his chest stand out a bit more in some places and flattening it in others. It wasn't bad, but after femming it up for so long, it felt weird.

The pants were worse. They were tight, so tight that he could barely pull them on. They weren't leather or fabric, either, but rubber, hot and tight and clenching at his ankles, making it clear that they were going to get him all kinds of sweaty under that. Worse, it was all but painted on, something a little nasty, though not as much as wearing a skirt and letting his cocks hang free might have done.

Understated? What the fuck?!

"Well? You ready?"

"Um...debatably."

"What's that supposed to mean?"

"Is anyone besides you out there?"

"Doesn't matter. Come on out," she said.

"Hey, you're paying for a show for you. For other people -"

"You don't know what I'm paying yet, kid. Now, get out here. This is the big leagues, now."

Annoyingly, she wasn't wrong. Iggy gritted his teeth for a moment, looking down at himself one last time, and sighed.

Might as well get it over with...

He opened the door, and his cheeks immediately went bright red. The wolf woman sat on a chair that had obviously been brought for her, and no less than six of the store attendants were with her. Three vixens, another wolf bitch, and two cats all turned to look at him, and they smiled widely as they looked him up and down. He'd been seen like a piece of meat before, but this really took the cake.

He couldn't stop blushing as he stepped forward, managing to show off his body in a way. As he turned for her as if he'd reached the edge of a catwalk, the wolf executive nodded in approval.

"That's much better. Don't know what your slut-mom was thinking."

"She said to go with something understated," he muttered.

"She - oh, that clever bitch." The other woman laughed. "She wanted you to get some clothes. God, she knew I wouldn't be able to take those things. That fucking bitch..."

"You - she -"

"Well, you look good in those. Come on." The wolf woman handed her card to one of the attendants. "Three sets of that, each a different color combo."

"Yes, ma'am," the vixen said before running off.

"And you." The wolf smiled. "Dance for me."

"Here...in the store?"

"Yep."

"But -"

"Heh, I said dance, kid. You want to earn that paycheck and impress me? Dance."

Knowing that his choice was to do what he was told or leave without any money - and possibly without any clothes - Iggy went with it. He slowly started swaying his hips, making sure to catch the light coming down. He'd done the strip-tease dance a few hundred times in his room, practicing for those nights at the bar and in a few other places. It worked for him, though he wasn't particularly polished.

As he swayed his hips, he could feel his pinned cocks rising against the panties he wore. They were throbbing a bit, getting more and more visible through the rubber pants. The wolf woman grinned wider and wider, pressing her hands together. Her nipples started to show through her top, and he wasn't sure, but he was almost certain that she was starting to get a little wet between the legs, too.

Oh god...oh god...

Iggy was getting horned up, too, his cocks twitching and throbbing. They weren't yet leaking, but he knew that they weren't far from it. Soon, he'd have a very messy sort of crotch space, and due to the rubber pants, it would stay that way until he actually had a chance to take them off.

The way that the wolf woman stared at him, he felt like less a piece of meat to be hunted, and more one already caught and marinading.

They were back in the limo about twenty minutes later. The vixen had taken forever to run the card, and he was sure that had been intentional. His cheeks were as red as they could get as they sat together in the car, the older woman rubbing his thigh.

"Mmm, you did great back there. And you look better, too."

"God, I've never done anything like that."

"Never?"

"Mm-mm," he muttered.

"Well, you did it well. And you're going to do more."

"Mmmph. How much more?"

"Heh. With the amount of whining you do, I'd almost think you were a pup."

"Hey."

"Kid. Did your mom explain anything to you?"

"..."

"Heh, she's letting you learn as you go, huh? Well, I guess she did the same thing. The number of times that she ended up blowing police officers to get out of jail..."

"You knew my mom, I get it."

"Oh, more than that. Had a crush on her."

"You - what?"

"Yeah. Not the same to have you, but hey." She chuckled. "At least I can go back to tell her, 'Hey, I fucked your son.'"

He didn't say anything to that. Really, what could he have said? He wasn't sure. Iggy's head felt fuzzy, funny, and he honestly didn't know how much more of this he could take.

At the same time, he was enjoying it, and there was no hiding that little bit of knowledge. His cocks were hard as could be, and they were twitching regularly as the wolf woman kept rubbing his thigh. She had a way to her that made her both terrifyingly efficient, and yet, very graceful, very feminine. It wasn't like she went super-butch, just...very direct.

"Let me guess. All you know is that this is different from street-walking, yeah?"

"That's...pretty much right," Iggy admitted.

"Then let me give you the highlights. If you get a client, you do what the client says. Point blank."

"Everything?"

"Everything. They tell you to blow them in public, then you better trust them to order it at a safe place. They tell you to get on your knees and pimp yourself out to a cop, then you do it."

His eyes felt like they were bugging out of their sockets at that revelation. He knew that it was going to be more extensive, but this...this was something that was well-beyond extensive. The way that the clients could use him like this -

The wolf woman shrugged, leaning back against her chair as he spluttered. She waited for him to finish, shaking her head in amusement.

"Heh, what did you expect? That you'd get more money for the same work?"

"I - no, but, this is nuts."

"It's what you gotta do to get this kind of money, kid. You're always on-call. You're basically a slave to your clients. But you get more money than any other prostitute ever will. And you get to pick your clients."

"..."

"That means that you better get real good at making quick decisions and knowing who's worth keeping and who's gonna get kicked to the curb, kid," she said, looking down at her nails. "Because the minute that you take someone as a client, they're going to be a hell of a lot harder to get out of that book than to get in it."

"What's the worst that you're going to do to me?" Iggy asked.

"See? That's a good thing to know. Little blunt to ask it that way, though. You'll want to figure out a better, more delicate, flirty way of finding out."

"What's the worst thing that you're going to do to me?" he asked again.

"Oh, you actually wanted to know."

He nodded.

"I'll be making sure that you smell like a slut...I'm going to make sure that you smell like sex all the time." She smiled, nodding at the rubber pants. "And I'm going to make sure that you get to show off that sexy body the way that it deserves to be seen on a regular basis. A good woman needs good accessories, after all."

"That's it?"

"Not kinky enough for you, kid?"

That wasn't the point at all, but he blushed regardless. The idea of being that well-used wasn't that bad, honestly. He could have gotten far worse from someone like this. That said, it was still a lot more than he had been expecting, and that first condition meant that he'd probably have to deal with wearing the rubber pants for at least a day before any time that he spent with her. If there was a sudden call-up, he might be able to get away without it, but if she had something scheduled, it would mean that he needed to start marinating down there well before she actually called him up.

Her hand was back on his thigh, rubbing up and pressing right under where his cocks rested. His breath caught in his throat as the older wolf leaned in, her breasts pressing against his arm.

"So, little slut. What do you think?"

"...What's the offer?"

"Heh, that's another good question. Retainer. $5,000 a month."

"$8,000," he countered.

"You're not that good."

"Yet."

"Yet? You think I'm a teacher?"

"No, but I'm a hard worker. I learn. And I do what I'm told."

"That's the basis of any good employee, kid. You want eight grand a month, you give me a damn good reason why I should pay that."

"Because -"

"And make it a good one, kid, or I'm dropping my offer to $4k."

Iggy bit his cheek. He forgot that he wasn't the one that was in charge here. More to the point, he knew that she was still owed quite a few favors, and had probably paid more for the clothes than most people paid for sex with him on the street. He needed to take a new tack, or he wasn't going to get anything.

And $4k wouldn't be good enough for this. By arguing, he'd lost something worthwhile for something that was just short of being good. Even if she had plenty of contacts for other people that might allow him to build up the little black book, he needed more from her to be sure that it was a good base investment.

He looked down at himself, wracking his brains for something...and then he smiled.

"You can dress me up like mom."

"...What was that, kid?"

"You can make me look like her. You can pretend that you get to fuck your crush."

"Keep talking."

"I'm not that different. I got the family ass. I got both dicks. Sure, I'm not that big in the chest, but that's not that hard if I'm fucking you doggy-style, or if you're looking away from me. I still feel like her."

"..."

"And I can be worth $8k a month for that, right?"

"...Heh. You're getting better at this, kid. Fine. Eight grand for the first month. We'll see if you're worth it for the next month."

"I'm guessing you'll have a contract waiting?"

"What do you think your book is for? Hand it over."

They reached her hotel without much further delay, and as soon as they entered the elevator, Mistress Moxie - whether that was her real name or a fake one that she came up with for the scene, he didn't know - pantsed him. His eyes went wide as she yanked the rubber pants down to his ankles while the door was still closing, his cocks throbbing outwards, the whole lobby of her hotel staring at him for a moment before the doors closed.

"What - mmmph!"

She shoved two fingers over his tongue, keeping him from talking. Her breasts pressed against his back as she stroked her other hand down over his cocks.

"Don't talk now...It's my turn to have some fun."

"Mmmph..."

"You're my slut for the night now, Iggy...Mmm...nah...I'm going to call you by a different name."

She stroked his cocks slowly, pushing them together, forcing him to feel the soft frotting feeling that came from the double-dick masturbation. He groaned against her fingers, pulling his mouth closed, sucking on them slowly. Mistress Moxie pressed herself against him more, nuzzling into his neck.

"Yeah, that's it...taste it, Ailsa..."

His mother's name made him blush. He could feel her all but grinding her pussy against his tail, pulling it between her legs for her own enjoyment. The wolf stroked him hard, painfully hard, almost, with her grip getting tighter and tighter as the seconds went by.

She pulled her hand back, smelling her fingers, sniffing up the musk that clung to them. She moaned under her breath, while his head swam from the strong scent. Being pinned in there meant that it stayed very powerful, very sexual.

"Fuck...you smell like her..."

"Mmmph..."

"I'm going to ride your cocks into oblivion, Ailsa. I'm going to show you what you've been missing all these years..."

There was nothing to do but pant as she kept groping him, teasing him, stroking him. She shoved him forward, bumping his hips with her own, forcing him to fuck her fist. His cocks were already stiff and eager, already hard and dripping.

Mmmph...

The elevator dinged, and she marched him out of the elevator, pausing only to drop down and take the pants that he'd left behind. She threw them over her shoulder, marching him along while jerking him off like mad.

God...damn...

It was a blur as they went from the elevator to her room. He felt them sliding through different corridors, stepping through the hallway to the penthouse, and then into the bedroom. The bedroom, mostly because he was tripped into bed, and the wolf woman followed him down. Moxie loomed over him, grinning widely.

"Mmm, I'm going to rock your world."

"You...yes, Mistress..."

"Say it again, Ailsa."

He cleared his throat, pitching his voice just that little bit higher.

"Yes, Mistress."

"Mmmmph...Oh, Ailsa, you have no idea how long I waited for you to say that..."

She was a freak. A total freak. But that didn't stop her from being sexy as she pulled her skirt off, tossing it to the side as she lowered her panties. He half-expected her to jump him, to slide herself onto his cocks right then and there.

But no. She leaned down first, sniffing at his shafts, dragging her nose up and down the sides. The raw, heavy, hot smell seemed to excite her all the further, leaving her huffing and groaning against his cocks. She dragged her tongue along one, then the other, forcing herself to stop after a few seconds.

"Mmmph...can't lose that smell..."

"Mmmph?"

"I'm going to make you remember me...mark you as mine, Ailsa...You're going to be my dick-bitch for a long time..."

You're fucking insane...

But at the same time, he couldn't deny that there was a sexiness to her obsession. His cocks throbbed for the wolf bitch, and as she slowly dragged herself over them, her pussy pressing against one shaft, then the other, he couldn't help but look forward to what was about to come. He gripped his cocks together for her, rubbing them against her pussy, and Mistress Moxie looked down at him with a wide grin.

"Don't you dare cum."

"Huh?"

"Don't cum until Mistress gives you permission."

"Uh, um, okay..."

"That's 'Okay, Mistress', Ailsa."

"Okay, Mistress."

"Good girl."

He blushed at that, only to be pushed to gasping as the wolf bitch slammed her hips down. In one go, she took the whole thing, leaving him huffing and puffing as she started riding him like a living jackhammer.

"Ah! Ah! Ah!"

His voice went higher, and Mistress Moxie loved it. She rode him harder, pushing him to the limits of his endurance and stamina. He never used his dicks when he was getting fucked by guys; nobody wanted to be penetrated when they hired a whore. This was something entirely different.

"Nnngh...ah...ah..."

"Don't you dare, Ailsa. I'm in charge, tonight. Don't you cum."

Being called by his mom's name was not helping, not in the slightest. His cocks throbbed all the harder between his legs, his eyes rolling back as he felt that pleasure rising, rising, and rising more. He whimpered, curling his toes against the sheets -

"Hey, I told you, don't!"

And just like that, Mistress Moxie had pulled herself off his cocks, gripping them at the base with iron fingers. He gasped, his eyes going wide, his cocks throbbing hard as an orgasm that had been just about to burst free was canceled right then and there. He flopped back, his mouth hanging open, his eyes glazed over.

"Fuck...fuck...fuck..."

"You really are bad at this, aren't you?"

"Never...used my...dicks on the job..."

"What, never?"

"No...females..."

"Or subby males. Jesus..."

Mistress Moxie slapped his cocks, and he yelped, not quite curling up, but coming close before she straddled him again. She looked down at him, shaking her head.

"Alright. We're going to have to try something different, I see."

"Something...different?"

"You always had a smart mouth, Ailsa. Time to put that to use."

That was something he could do. He started to sit up, only for Mistress Moxie to shove him back down. She slid around him, pushing her ass in his face, her pucker right over his lips.

"No. Here."

"Mmmph...yes, Mistress."

"And don't...cum..."

Why he might was answered a second later. She leaned back, pressing her toes to his shaft, and she started jerking him off with her pinched digits HARD. He groaned, squirming against the sheets, but now that she was sitting on his face, there was no escape for him. Forced to lie there with her soles jerking him off and her rounded, musky rump in his face, Iggy was effectively pinned for the duration of the night.

As he put his tongue to work, putting everything that his mom had taught him and his clients had helped perfect to the use of his new client, he realized he had a lot of exercises to do if he wanted to keep Mistress Moxie happy, and if he wanted to keep that $8k a month. That was a lot of money to lose just from dicks that didn't have enough stamina.

Here's hoping mom knows something to help with that...

The End

Summary: In an effort to get a richer client, Iggy ends up finding one hell of a mistress...

Tags: M/F, Femdom, Wolf, Stingray, Series, Prostitution, Vaginal, Double Dicks, Embarrassment, Dressing Up, Musk, Education, Oral, Rimming, Footjob, Pre-cum,