by Ava Sinclair
“What’s that supposed to mean?” I’ve never used this kind of tone, but I’m pissed at him.
If Mr. M. is mad, he doesn’t show it.
“It doesn’t mean anything other than I need to step up my game if another man got you that wet just by taking you to dinner.” He pauses. “So. What was he really like?”
I pull the screen level and flop down on the bed, deciding to be honest. “Handsome,” I say. “In fact, he is the first man I’ve met who’s as attractive as you are. Tall, and in a tailored suit.”
“No fair,” Mr. M. chuckles. “He’s starting a chain of clothiers, right?” He tents his fingers under his chin. “Maybe I should buy him out.”
Now I smile despite myself. “You’re jealous?”
“No.” He sighs. “Well, maybe a little, at least until I remind myself that if you’re wet, he’s probably back in his penthouse jerking off while he’s thinking about you.”
“Don’t say that,” I scold. “He’s a client.”
“And you’re a hot lawyer. And attraction doesn’t abide the parameters we place on it. It is what it is.” He nods in my direction. “You broke position without asking,” he says. “So now you’ll be punished.”
“That’s going to take some doing, given that you’re hundreds of miles away,” comes my cheeky reply.
“I have my ways,” he says. “Open your package.”
I’ve almost forgotten, and take it from the bedside table. I have to sit back, and Mr. M. is watching me as I open the box. Inside is a heavy glass dildo that’s almost beautiful. It’s round on the top, the shaft ridged, growing wider before ending in a flanged base.
“You like it?” Mr. M. asks.
“Yes,” I say. I recognize the manufacturer as Ann Summers, a British sex toy company I discovered when I was working abroad. I’m touched that Mr. M. remembers my mentioning them, and I’m about to thank him, but he speaks again.
“Put it in the freezer,” he says.
“What?”
“You have a mini fridge in your room. Put it in the freezer. And hurry. There’s something else in the box.”
I rise from the bed and do as he tells me. Then I go back to the bed. I only see tissue paper in the box, which I remove. And now the dildo isn’t the only thing feeling a chill. In the box is a short, thick strap with a handle on the end. I look at the computer questioningly.
“Pick up the strap and turn your ass to the computer,” he says. “I’m going to count out the licks, and you’re going to spank yourself while I watch.”
My mouth goes dry. “Why?” I ask.
He leans forward. His eyes are smoldering. My heart glitches in my chest and my panties are wet all over again. “Because I can,” he says. “Now bare that ass.”
My right cheek is pressed against the king-sized mattress as I peel my panties down to mid-thigh. In my mind’s eye, I imagine the scene as Mr. M. sees it, my bottom filling the screen.
“Pick up the strap,” he orders.
I obey, feeling silly. Even when I was a neophyte sexual submissive, I never succumbed to the temptation to self-spank. It seemed silly, and I couldn’t imagine any sexual or disciplinary benefit, but when he orders me to smack my ass, I obey. There’s a soft leathery splat as the length of it descends on my left buttock with a mild sting.
“No.” His voice makes me jump in a way the first blow didn’t. “Hard, Sloane. You’d better feel the next one, understand?”
I raise the strap higher, rotating my torso a bit as I raise my arm. I steel myself as I do as he says and am surprised to find it hurts, that I’ve hurt myself. I drop the strap and reach back to feel the ridges of a welt forming on my buttock. I look back at him and feel tears prickling at the corner of my eyes.
“That hurt!” I say accusingly.
“It was supposed to,” he replies. “Do it again.”
“I have to sit for a meeting tomorrow.”
He’s unmoved. “Do. It. Again.”
I lift the strap. My hand is shaking. I know if I deliver a lackluster blow he’ll just make me repeat it. I squeeze my eyes shut and press my lips together as I bring the strap down. This blow intersects the first and catches both buttocks. I issue a little scream and bring the strap to the mattress beside me, my hand gripping the handle as I wag my injured bottom back and forth.
“Mr. M.…” There’s a plea in my voice. “I won’t break position again. I won’t…”
“Again, Sloane.”
I consider refusing. This is worse than when he spanks me. I’m helpless then, but now I’m having to do it to myself on his command. I’m terrified to pick up the strap, but I do. This one lands in the same spot as the second, which is agonizing. Somewhere in my mind, logic tells me to vary the location of the blow. I’m sobbing. I look back and see him watching. He’s leaning forward, his gaze intent on my bottom. He’s punishing me from another time zone, and suddenly the knowledge of that, the knowledge that he’s exercising this control from there sends a surge of sexual excitement through my body.
“Spread your legs,” he orders, “and aim the next blow down the crack of your ass.” I respond with a stricken little moan, my hand shaking as I raise the strap, my knuckles white around the handle, knowing where the tip of the strap will fall. I don’t want to do it. But I want to do it. I’ve crossed that threshold now where pain and pleasure are swirling together, where doing his will infuses me with a delicious, languid thrill, even as the pain makes my legs shake.
I bring the strap down, having lost count of how many licks it’s been—seven? eight? The tip of it catches my labia, and a stab of delicious agony blooms from my labia through my core. I wail into the bedcovers, wagging my bottom from side to side. Through the haze of pain, I hear his voice commanding me to pick up the strap, to continue with the self-punishment that doesn’t feel like self-punishment. At his command, my hand has become his, and my reaction to the correction is the same as it would be if I were over his knee.
Two more. Two more crisscrossing blows and it is done. My ass is a hot welted mess. I know because he tells me this, and tells me he’s gotten some nice screenshots.
“Sloane. Sloane!” I hear him sternly call my name and raise my head from where my face is pushed into the bedding. I look around. The computer screen is hazy through my tear-filled eyes.
“Yes?” I ask.
“Go to the freezer and get the toy.”
The dildo. I’d forgotten. I stand. My legs are wobbly and my bottom is throbbing like a heartbeat. The dildo is the only thing in the small upper compartment of the fridge. It’s chilled quickly. I take it back to the bed. Does he really expect me to put this cold thing in my pussy?
“Back in position,” he says.
I comply.
“Now, put the tip of your toy in your pussy, just far enough to lubricate it. I know you’re wet. I can see it. It’s on your thighs. Your pussy is so swollen, so pretty. I’m going crazy imagining the smell of you. If I were there, I’d eat you for an hour.”
My pussy clenches at his words. I wish he was here.
“But I’m not with you,” he says. “You’ll have to continue without me, so slip that cold dildo in your pussy long enough to get it nice and lubed.”
Obeying this command makes me jolt. The heavy dildo feels like smooth ice sliding into my pussy. I can’t decide if I like it, but don’t really have time, because now Mr. M. is commanding me to stick the lubed dildo in my ass, to slide the cold head into my anus.
What am I expecting? Not this. The cold of the dildo’s head stings the sensitive skin of my asshole. It’s like a little burn that goes numb as I press. The numbness makes it easier to push it inside. It’s a good thing I take yoga; it allows me to reach through my legs and manipulate the dildo. I hear Mr. M. saying things like, “Mmmm, that’s it. Oh, yeah, baby.” And damn… I’m hot and cold now. I’m wriggling as I obey his words. I’m in a trancelike subspace, feeding on his approval and pleasure, buoyed by it. I’m awash in sensation
—the pulsing sting of my bottom, the cold bite of the dildo as it slides in and out of my ass, the clenching of my pussy. I don’t ask permission to use my other hand to stroke my clit, but Mr. M. doesn’t seem to mind. In fact, he’s urging me to come, telling me he wants to see, telling me how turned on he is.
My orgasm makes up for all of it. It makes up for the self-strapping that proved I can’t escape punishment should Mr. M. wants to give it. It makes up for the stark invasion of the dildo, which hurts so good in my ass. It almost makes up for Mr. M. not being in the room, although in truth there’s nothing like his fingers when it’s down to it.
When the last waves ripple over me, I remove the dildo and put it aside. I roll onto my back, looking at Mr. M. through my spread legs. He’s smiling at me.
“My girl,” he said. “My remarkable girl. Good luck tomorrow.”
Chapter Eight
Her name is Camille, and physically, she’s just my type. Where I am lean and hard, she’s soft. I wouldn’t call her heavy. She’s plush and curvy with pale skin and hair a shade of red that I’m sure isn’t natural. It’s cut in an old-fashioned bob and the dress she wears is kind of retro, too. It’s pink with white polka dots. Her shoes are pink and low-heeled, with little white bows on the back. Cute.
Mr. M. said he’d invited a guest over for dinner, and when I arrive late to find her sitting in the living room making small talk, I’m surprised. I’d expected a business associate, not a woman who looks me up and down from underneath impossibly long false eyelashes.
“Hi,” she says, standing up. She extends her hand and I take it as she introduces herself.
“Camille is a prostitute,” Mr. M. says, and I’m left speechless by this sudden disclosure. I glance back at her, taking in her curves and her pin-up prettiness. I’m wondering if she’s for me. Mr. M. has said sharing would be part of our dynamic, and I wouldn’t mind sharing him with her, or his sharing her with me, or the two of them sharing me. In fact, I’m getting kind of turned on by the notion when he tells me the real reason she’s here.
“I’ve hired her to teach you how to do what she does,” he says.
Now I laugh. “Um, Mr. M.… I already know how to do what she does.”
“I’m not talking about how to have sex,” he says. “I’m talking about how to be a professional.”
I look over at her, wondering whether the frankness offends her, but the edge of her pretty mouth is curved up in a smirk.
“I told you, didn’t I, that there are times I’d expect you to be my whore?”
Oh, yes, I remember. I agreed to it. We’d talked about it, about my letting go of my buttoned-up persona and being his dirty girl, his filthy little slut. And I’d been waiting for one of my daily underwear selections to include ripped fishnet stockings and crotchless panties along with orders to meet him at some seedy hotel on the outskirts of town.
I look over at him. “And Camille is going to teach me… what, exactly?”
“Accuracy,” he says, picking up my hand and giving it a kiss. “If you’re going to play the whore, I want to be convinced.” He looks at his watch. “Well, I’ll leave you two to your lesson. I told Kevin I’d play racquetball tonight.” He winks at me. “I’ll text you later.”
I watch him leave, not knowing what to say. When I turn back to Camille, she’s walking around, taking in the spacious apartment.
“Nice digs,” she says.
“Yes,” I agree.
“So what’s he do?” She trails a finger over the back of the sofa. “Your boyfriend, I mean.”
“He’s rich,” I say. “That’s what he does, being rich.”
“Must be nice.” Her voice is high and pretty. “What about you?” she asks. “You work?”
“I don’t like to talk about myself,” I say. And that’s true. Mr. M. is lucky. He can do whatever he likes. He doesn’t answer to anyone. I have the firm to think of. I have to be careful.
“That’s cool,” she says, and drops it.
“You’re really a prostitute?” I ask.
“Yep,” she says, and plants herself in a chair, testing it for comfort.
“I’m sorry about what he said… calling you a whore, I mean.”
She giggles. “First rule of being a prostitute, honey, is that you have to have a thick skin. If a man pays me enough, he can call me anything he wants. And he can do anything he wants.” She arches an eyebrow. “As long as it’s safe.”
I take the chair across from her. I like this woman.
“So what’s the weirdest thing you’ve ever done?” I’m intrigued, Mr. M. is out, and she’s being paid by the hour. I can ask her whatever I like, and it makes me happy that she’s making money answering my questions.
Camille sits back and crosses her legs. I can see that she’s wearing thigh-high stockings; when the hem of her dress rides up, I can see the top of one. Sexy.
“Let’s see,” she says. “I had this one guy who wanted to lie in a kiddie pool full of Jell-O while I read Goodnight Moon to him until he came.”
“You’re kidding?” I can feel my eyes widen.
She crosses her heart. “Swear to god.
“Sure, most guys want the suck-and-fuck, the things their wives used to do, but won’t anymore. But for a lot of these guys, it’s not just about sex. It’s about validation. They want to be told how big their cocks are, and I do, even if they’re barely four inches hard. Or they’re jilted, or divorced, and want to make me the image of every woman who rejected them. Those are the worst. Those are the ones who pin me against the wall and anger fuck me, although half of them lose it before finishing.”
She falls silent, and I stare at her, mesmerized and impressed. I want to tell Camille that she’s awfully well-spoken for a whore, and she seems to read my mind.
“I never foresaw this would be my life when I got my English degree from NYU,” she says, and a more complete image emerges. “Employment is hard to find. But everyone wants a blowjob.”
“How did you…”
“Start?” Camille smirks. “Well, I didn’t go to college for this. But I didn’t go to college to end up working part time tutoring surly teenagers in English, but that’s the only job I could get. So I started supplementing my income at a gentleman’s club.” She makes air quotes with her fingers as she says ‘gentleman’s’ and rolls her eyes. I can’t help but smile at her sarcasm.
“The money wasn’t bad,” she continues, “but some of the girls told me it could be even better if I were nice to certain clients. We were allowed to give lap dances, and one night while I was grinding this guy’s crotch through his Dockers, he whispers to me he’ll pay extra if I let him finger me. And the rent was due, sooo…” She sighs. “One thing leads to another, and the next thing you know, I’m Camille, the Working Girl.”
“Is Camille your real name?”
“Oh, I don’t like to talk about myself.” She grins as she repeats my words back to me and I feel ashamed, pressing her for information when I wouldn’t even tell her what I do for a living.
She stands up. “But enough about me, anyway. Your man is paying me bank to give you whore lessons, so let’s get started.”
“Is it dangerous?” I still have questions, and am pleased when her face softens a bit and she sighs.
“Not if you’re careful. I don’t do drugs. I don’t have a pimp, but most higher-end girls don’t. The Internet allows us to screen our clients. I have my regulars and that makes it safe.”
This gives me pause. “Is he one of your… regulars?”
“Your beau?” Camille laughs at this. “No, honey. One of his friends is, but I didn’t ask who. I’m discreet.” She holds out her hand. “Now come here.”
I walk over and take her hand. It’s soft and warm and I feel a twinge of sullen regret that Mr. M. isn’t allowing me to sleep with her. She’s so pretty, and I don’t care that she’s a working girl.
“I assume your man wants the whore fantasy?”
I demur at this.
“He wants more than a fantasy. He wants me to assume the character.”
“Ah… well, then the first rule of being in my line of work is that you don’t get attached. So you’ll need to be artful in your skill, but keep your mind aloof. Keep your reserve.”
I nod, refraining from offering the truth, which is that I’m already keeping that reserve, and that despite what she thinks, I don’t consider myself his girlfriend.
“Your job is to give pleasure.” She looks me up and down. “I’m thinking you’re already good at that. But if you don’t detach a little during this, it’s going to feel like any other fuck with his girlfriend.”
It seems backwards, but I kind of get where she’s coming from. I wonder if Mr. M. has ever been with a prostitute. I can’t imagine him paying for it.
“Safety is important,” she says. She reaches for a clutch bag on the sofa table and opens it to reveal an array of condoms. “I’m clean,” she says. “I have documentation to prove it. I’m tested for everything. But I don’t pry into the lives of my clients, not even my regulars. I don’t assume there aren’t other women, even other girls like me. Condoms are non-negotiable. If he doesn’t cover, we don’t fuck.”
I’ve never used a condom with Mr. M. We have both been tested for STDs by mutual agreement and are clean as two kinky whistles. I try to imagine demanding Mr. M. put on a rubber and almost laugh.
“What about oral sex?” I ask.
“Same thing,” she said.
“You blow him over the condom?”
“If you know what you’re doing, it can be better than doing it on the bare.”
This seems unlikely to me.
“What if they want to go down on you?”
“If they don’t have a festering mouth sore, I let them,” she says. “And one of my clients? That’s all he wants. I call him Marathon Man because he’ll literally stay down there for an hour.” She rolls her eyes. “He’s like a friendly Labrador retriever—all enthusiasm and no art. To date I’ve faked about three dozen orgasms with his head between my legs. If he’s wise to me, he’s not said.” She paused. “Sweet old guy, that one.”