This May End Badly

"Fucking do what I tell you!" I slide a second finger into her tight anus and clamp my mouth down on her pussy.

"Oh! Oh fuck! OhGOD OHFUCK!! I'm... I'm..."

As her body rips into convulsions, something warm hits my tongue in short bursts, and I let it pool in my mouth as I spread the fingers in her asshole. My cock throbs and feels as though it may burst.

I swallow her emissions, and another finger goes into her sopping cunt to work her g-spot as her orgasm drags on, her moans load enough to wake the neighbors, her body pushing against her restraints. Another burst of squirting fills my mouth, and I swallow. For a moment, I worry the restraints won't hold, but I know my business. When it feels as though she's spent, I slowly remove my fingers from her cunt and anus.

"I do like it when women listen to me," I say. "I may reward you for that."

"Did I... um...? I'm sorry I..."

I rapidly push two fingers into her cunt and pull her upward. "I didn't tell you to apologize! If you try that shit again, I'm going to whip your tits until they're black and blue. Do you fucking hear me?"

Her throat is tight as she says, "Yes."

"What did you say?" I increase the pressure on the anterior wall of her vagina and pinch her nipple with a twist.

She screams and yells, "Yes! Yes! I understand!"

"Good girl," I say, lowering my mouth to her nipple, sucking and kissing the spot I just attacked. Then I drop into her crotch again and lick her clean. Her pussy first, all along her lips, and then her anus.

When I sit back and finally begin rubbing my cock, she asks, "Did you really... like it?"

"Don't ask stupid questions."

"But was it... did it taste good?"

"It tasted like you, and that's exactly what I wanted. Did you like it when I was eating your asshole?"

"Fuck," she breathes, "that's so dirty. Yes, I fucking loved it."

I recall the interview once again...

x x x

"When was the last time you were butt fucked?" I asked.

"Technically? Never. A guy tried once, but it was a disaster. Sometimes I orgasm with something up in there."

"What do you use?"

"My fingertip. Or a little vibrator."

"A cock is a lot bigger than a little vibrator."

"That's why I need your expertise."

I asked her, "Why do you want this?"

"My girlfriend said it was the best orgasm she'd ever had."

"You're going through a lot of trouble for just an orgasm," I said. "You don't know me. You're going to be tied up. Completely helpless. I could do anything to you. Doesn't that scare you?"

"Of course, it does," she said.

"Then why?"

"I've spent my whole adult life doing things that other people wanted me to do," she said. "I'm sick of being pushed around."

"So, you're hiring me to push you around?"

"But this time it's my choice. Plus, it beats playing with myself. What about you? Why do you do it?"

"I'm looking for my soulmate."

"If you don't want to tell me..."

"I'm saving," I said. "I want to get a boat."

"You tie women up and fuck them so that you can buy a boat. Everyone needs a hobby, I guess."

"It's past time to leave this city," I said. "I uh, I lost someone not too long ago."

"Oh. Oh uh. I'm sorry. I didn't know."

"There was a lot of medical debt after, so I had to sell the house. I don't know where I want to be, but I don't want to be here. So yeah. I'm going to buy a boat, and I'm going to sail around until I find a place that feels better."

"That sounds nice," she said. "Maybe you could take me with you."

"So presumptuous," I said with a smile. "What if I'm bad at fucking? A long boat ride sure would be awkward after that."

"I very much doubt I'll have a problem with your fucking, given the recommendation I received."

"I guess we'll find out."

She gasped at that. "You mean you'll do it? You'll take me as a client?"

"How's your schedule next Thursday?"

x x x

I grab my bag and pull out a set of balls on a string and a 20oz bottle of fresh lube, making sure she has a good look at both before I roll her over onto her front. Her head to the side, taking her weight on her breastbone and knees, her ass sits high in the air.

"These balls vibrate," I say. "They'll help you open up and get ready to accept a cock."

"Yes please," she says, her cheek pressed to the mat.

But I can't begin proper prep until I indulge a bit more. I plant my face between her ass cheeks and begin flicking and licking her anus as I would her clit. My hands run the length of her back during my ministrations, along her spine, up and down her sides. I press my tongue into her dirty pucker, and it spreads nicely at the pressure. I can't resist tongue fucking her asshole now, and her gentle sighs at each penetration make my balls hurt.

Uncapping the lube, I squirt it onto her anus which I then massage with circular motions, pushing my fingers inside with every other pass. Already, she's humming with pleasure. I then gently slip the conical tip of the bottle into her asshole and squeeze out a substantial volume. People miss this step, some because it's messy, others don't know better. But it makes all the difference.

I continue to work her anus with my fingers. I'm pushing against her inner sphincter now, simple penetration and circling, and using the fingers of my opposite hand to pet her pussy. Some women are particularly sensitive right after an orgasm, so I'm careful of her clit. She hums pleasantly.

I press a small button on the last and largest of the string of balls, and they all begin to vibrate. The first one I line up with her anus and say, "There are five balls here, each one getting larger. We're going to move them in and out one at a time, and you'll need to help with that."

"Help... help how?"

Her anus swallows the first ball easily, same with the second. The third resists. "Deep breath in, slow breath out. Relax your asshole when you breathe out." The ball enters, a small dribble of lube exiting as her pucker closes around the string. "Did that pinch?"

"A little."

"Now, I want you to push it out."

"Push it out."

I run my hand over her ass cheek and cup the mound of her pussy. She hums as I rub, firm and slow. "Yes, push it out."

"But um... If I..."

"If you what?"

"If I pee..."

"Do you have to pee?"

"I think so."

"Then you pee."

She begins, "But..." I drop my middle finger onto her clit, mushing her outer lips together with the rest of my hand. "Nnnngggg," she moans.

"In my dungeon sessions," I say, "I have seen the floor literally flooded with piss, lube, breast milk. Liberate your body. Let it do what it's going to do."

There are other ways to handle this objection. Shame is a massive turn-on to some people, especially submissives that hire a guy like me. But I've gotten to know this one as my job requires. Playfulness, trust. These are important to her. She'll feel shame anyway, but she needs to be given permission.

"People really pee on the floor?"

"Imagine being tied up for three or four hours at a time, your body going through nonstop stimulation." I circle her clit, and her hips begin to wiggle. "Some people piss into a cup or a bowl."

"Oh my God."

"If you piss, you piss. Abandon your reservations. Enjoy the way it feels."

"But your hand."

"Is already wet. Now push."

"Gawwd."

"Push that ball out of your ass."

A moment passes, and her anus flares revealing more and more of the vibrating silicon until it drops into my open palm, along with a gush of lube. She manages to keep her piss in her bladder. For now. The lube I rub on her ass cheeks, and the ball I place again at the opening.

"In and out. I push it in, you push it out."

"Fuck."

Her anus swallows the ball once more, and then she pushes it out. The flare of her pucker is beginning to look larger as the ball drops into my hand. In and out, in and out, in and out.

Meanwhile, my semi-flaccid cock is oozing precum all over my leg.

"This time don't push," I say. "We're sizing up."

I push the third ball in, and she takes it easily. The fourth ball is substantially larger, and she hisses as it catches on her inner sphincter.

"Breathe."

She does. The ball goes in.

"Push it out."

She whimpers.

I intensify my ministrations upon her clit. "Push. It. Out."

As her pucker flares, I can see she's having a hard time passing this one. But soon enough, the ball exits with a new wave of lube, a jet of warm fluid hitting my palm before dripping onto the mat. Her whimper is long. "Did I just..."

The smell hits. "You peed in my hand." I place two fingers up into her slippery, sodden cunt and I rub her g-spot. She moans with discomfort. "Let the rest out. You'll feel better."

"I... I can't."

I press the fourth ball into her asshole again, and she yelps. "Then push."

Her muscles contract, and the walls of her vagina close over my fingers. This time, all of the balls, their binding string, and a gush of lube falls out and splashes onto the mat. The hissing jet of piss that follows continues, hitting my hand, flooding around her knees and mine, and spilling onto the hardwood floor. She pinches off the stream with a little gasp.

"Push!"

And I rub her clit as her body contracts, her moan of an ecstasy somewhere between shameful misery and liberated bliss, piss hitting my wrist as I rub her to orgasm. Her moans are low and loud, and I watch as the rest of the lube and anal mucus appear, pushed out by the cherry red of her rectum.

She doesn't need the fifth ball. She's ready now.

I don't hesitate, my dick painfully hard within a second. Climbing to my feet, I squat and thrust my cock deep into her asshole, and she takes my entire length to the base.

"Oh fuck," she moans as I thrust. "Oh fuck. Oh fuck. Oh fuuuuuuuck!"

A minute ticks by, two, three as I thrust with long and powerful strokes, and her moaning becomes something between crying and yelling.

I'm not going to be able to hold on for much longer, my cock wrapped in the slippery silk of her rectum, the sound of her sploshing anus, the wails of pleasure from her throat. I'm nearly there.

"Do you want my cum in your nasty asshole?" I grunt.

"Yeeeeeeeessss!" She gasps. "Pleeeeeeeeeease! Fuck me oh fuck my ass! Cum in my aaaaaaaaass!!"

She begins to wail, gasping for air, and I can feel fresh squirt splashing on my ankles.

"You feel that? Feel me cumming in that filthy fuck hole?"

"Yeeeeeeeeeesss!"

The muscles of my taint compress, and I feel spurt after spurt of spunk erupt through my cock, the delicate slippery walls of her rectum milking every last drop from my balls. Waves of pleasure explode through my core, up my spine, sizzling up the back of my neck.

I continue to thrust until she squirts, no words, all moaning and gasping as I know she's cumming again. As her breathing slows, so does my thrusting, the inside of her ass massaging my cock, my pulse dropping, my breath settling. I'm reluctant to pull out of her. Never have I so hated the restraints that prevent me from rolling onto our sides until I soften within her.

But that is not our relationship.

Extracting my still-hard rod from her asshole, a crimson gape remains. "There...," I say. "Stay right there."

"I couldn't move if I wanted to," she says, a smile in her voice even with her face mushed into the floor. "And I don't."

Grabbing her phone, I click a few more photos of her glistening pussy, her ruined, gaping asshole, the mess she made on the mat. I flex my toes in the puddle with a splish. "You hear that? You did that. Aren't you proud?"

"I don't fucking care," she says. "That was amazing."

"Well, I'm proud of my girl," I say, quickly tapping her ass cheek before wiping the sweat from my brow with my forearm. "That's a lot of piss. And squirt. Mostly piss."

"Yeah, I have news for you. If you don't untie me real fucking fast, I'm going to piss again right here."

Chuckling, I say, "Sounds like your problem, not mine."

She's silent and unmoving for a moment. Then fresh, yellow urine dribbles from her urethra and down her inner thighs to join the pool at her knees.

"I was kidding," I say. "I would have untied you."

"I don't fucking care," she says. "You let out the demon. Good luck getting her back in. Hey, didn't you say clean-up was included?"

Starting with the outer knots, I begin to remove her restraints. "That's right. It includes a shower, if you're up for it."

"Um, yeah. Because no offense? You smell like sex and piss."

There's nothing to do but laugh out loud.

When she's free, scooted out of her mess, I advise her to curl up in a ball at the far end of the mat, ass in air.

"Fuck me, that looks good," I say.

"Did I do a good job?" she says, turning her head gingerly.

"Spectacular," I say. "I probably pushed you a little harder than I would in a typical intro session. But you seemed ready for it."

"It felt perfect," she says. "I can't believe that was just an intro."

I kneel beside her and slip three fingers into her asshole, and they enter with almost no resistance. Her hum is easy and light. "Would you be interested in something more intense?"

"Like what?" she says, her eyes widening. "Fisting?"

Lifting a shoulder, I say, "There's a lot more to bondage than taking anal on the floor. Suspension is interesting. If you want more anal, there are insertions and prolapsing. There's breath play, wrapping, electrostim, sounding."

"What's sounding?"

"Steel rods in your pee hole."

"Um... yeah no."

"I have partners I work with sometimes if you're interested in double penetration. Women and men. Your choice." My fingers circle her destroyed outer sphincter and then dip inside to fuck her slowly.

"Is it weird that I only want you?" she says, pushing my fingers out with her core. Her crimson rectum bulges slightly beyond her anus, and a sizable glob of my cum exits and oozes down her pussy. I rub it into her already-wet pubic hair.

My heart beats a bit faster. "If I'm being honest, that would be my preference as well. It's not really an appropriate opinion, though."

Carefully, she pushes herself up to hands and knees and turns toward me. "I love that you... holy shit, are you still hard?" She reaches between my legs and begins stroking my cock. "I love the way you feel in my hand. Do you like it when I serve you?"

"I'm supposed to be serving you. You paid for domination."

"That's over," she says, leaning forward to place a supple kiss on my lips, my cock wet beneath her strokes. "Now, I want to serve you. What can I do for you? What do you want?"

"It doesn't matter what I want. Not really. I'm a whore."

"For tonight, you're my whore. And I want to know how to pleasure you." She dips low and begins to tongue my nipple.

"Fucking hell," I whisper, playing with the stray hairs on the back of her neck.

"Let's have a shower," she says. "Let me wash you."

We climb to our feet and she pulls me by the hand through her house and up the stairs. I watch her bum wiggle as she ascends.

Oh fuck, I almost forgot. "I need to get those nipple rings off you," I say near the top of the stairs.

She turns so that her breasts are in my face. "Would you like to take them off with your mouth?"

Grinning, I say, "That's the absolutely best way."

And so it's my turn to nurse, my mouth closing softly over her cold, purple nipple. Teeth and tongue, I remove the first and place it in her hand. After the second, I remain in place, flicking and licking. I dare not suck after those rings were in place far too long. She holds the back of my head against her breast, moaning sweetly.

"What do you want to do to me?" she asks.

"I want to worship your pussy."

She lifts her leg and places a foot on the banister, her soaking, hairy cunt reeking of the things we did downstairs. I press my nose into her bush and devour her. Slurping at her swollen, meaty lips, my tongue sucking and dancing over her clit, my hands travel up her thighs so that I can slip a finger in her cunt and another in her ass. My other hand jerks the head of my cock.

She breathes through it, blowing air through her lips, bucking her hips toward my face as my tongue enters her and swirls around and around. "Do you want to fuck my pussy?" she asks.

"Yes," I whine. "Oh God yes."

"Do you want to cum in my pussy?"

My words are muffled against her cunt. "More than anything."

She draws me upward once more and kisses me deeply, my lips sodden with the mess of our sexual juices.

"My condoms are downstairs," I say.

"No," she says. "I want you to feel my insides bare."

"That wasn't the agreement."

"Neither was fucking my pussy. I don't want any barriers between us. Unless it's a money thing. I... I can pay more..."

Placing a finger to her lips, wet with her juices, and slip it into her mouth.

"You've more than paid your bill," I say.

"Then I want you to cum in my pussy."

I swallow and nod. Her small hand closes over my large one, and she pulls me up the stairs and toward her room.

Her bathroom is all clean stone and glass and steel save the shower's cedar bench seat. A purple rubber cock is suctioned to the glass. I walk by and give it a flick.

She giggles as it bounces. "Guess I don't need that anymore."

"You think I'm going to be coming over that often?" I ask.

"Until I'm broke or dead," she says, pulling the shower handle and kissing me again. We make-out against the glass, our hands traveling over each other's bodies until the bathroom is hot with steam.

Pulling me into the shower, she grabs a bar of soap and begins to lather my chest and under my arms. The soap feels cold and hard against my body, a complete contrast to the softness of her fingers, to her skin as she slides her body over mine. Maneuvered behind me, she reaches around and soaps my cock, then she proceeds to stroke. She presses my hands to the bench, and soapy fingers press into my asshole. I feel my arousal growing more potent with every stroke, every penetration of her fingers and circle around my prostate, but no matter how amazing this feels, I can't stand not kissing her. So, I turn, and she continues to stroke my cock as we make-out beneath the hot, cleansing waters.

"Sit down," she says, guiding me to the bench seat. Now on her knees, the water cascades through her dark hair and down either side of my thighs as she bobs over my cock. Her mouth is just as silky as her asshole, only her skilled tongue causes my breathing to escalate, my heart to pound.

"Please let me fuck you," I say, lifting her hair out of the way.

"Where do you want to fuck me?" she says.

"I want to fuck your pussy. I want to cum inside you."

She bites her lip and climbs onto my lap. There is no teasing, no preamble. Her pussy envelops my cock as she lowers her body onto me.

Riding slowly, her hips rocking, I can feel my cock go hard as steel, my body tightening in preparation. I reach my hand around to run my fingers the length of her spread cheeks, and I drop a fingertip into her anus. She moans, "Yes. Yes, do that." Some of her tightness has returned, but she's still loose. I could fuck her ass again if I wanted, but I can't remember a pussy feeling so good.

"I can't hold on," I say, leaning forward into her breasts, my mouth finding her nipple. "I'm going to cum fast."

"Do it," she says, riding harder. "Cum inside me."

"Are you going to?" I ask, my fingers pressing up into her bobbing bottom in this oddly pleasant dual penetration.

"I just want to enjoy how you fill me up," she says. "You cum whenever you're ready." And she kisses me, her tongue entering my mouth, mine entering hers.

As her sloppy cunt swallows my cock over and over again, my fingers exploring her dirty hole, and with the heat of the water and the addition of our mouths, I can't seem to think beyond a certainty that I'm going to explode. I begin to moan, my throat tightening.