I could have slotted this into anal, BDSM, or romance. It’s all three of those things. Trigger warnings: anal, some bondage, heavy degradation/humiliation, consensual non-consent, maledom (fem-sub). It starts off romantic and then changes into something…quite different. I’m not a fan of stories involving rape nor M/f in which the f doesn’t enjoy it, so I’ve written about consent and pleasure in ways I find hot. It’s also quite romantic.

“How discrete can you be, Rachel? Or maybe I should preface that statement: do you want to engage with me in a manner that would call for discretion?”

I suppose that’s a strange question to ask. But in this case, it’s necessary. You see, I’m a summer associate working at a firm in the city, and my boss-mentor is asking me that question.

The question isn’t out of left field because our attraction had been building for a while. I noticed it as soon as we met, when he was one of the panel members on my final interview for this job. The attraction grew to a full-fledged crush over the past seven weeks of working closely with him, as I learned that he is brilliant and kind. I knew it wasn’t one-sided either, because you could have cut the chemistry between us with a knife. Like this afternoon, in the office, we were looking over a document together, sitting side-by-side, and by page three, I noticed that the space between us had shrunk. I could feel his warmth, smelled his clean freshness, and I could definitely pick up the faintest bit of something that made me think he was a little turned on. All of which made me breathe harder. We made eye contact, and he smiled before he moved away a few inches.

Then he said “Hey Rachel, I’d like to talk to you outside of work tonight. Let’s grab an adult beverage, if you don’t have plans?” I had tickets to a talk, actually, but I said yes because I wanted to hang out with him more.

And here we are, in an old-fashioned, darkened bar in North Beach. He leans back, spreads his arms, and studies my face. His oxfords are impeccably tamed to a professional polish. The premature lines around his dark eyes crinkle when he smiles or frowns. His smile, the expression on his face, the ease with which he takes up space, all of it suggested charm, humor, strength, confidence, and a sharp, observant mind. All qualities that make him an excellent lawyer. He looks almost too perfectly the part of the mid-thirties lawyer on the rise, with those tamed dark curls.

Even his name is great: Ezra Kaplan. Ezra means help or helper, and I’m grateful to have his mentorship.. Ezra is also only four years older than me but…just…you know, if only he wasn’t my boss.

“Are you asking me for something, Mr, Kaplan?” I drop my voice, hoping it's a seductive purr. I’m not sure it is working, because I’m barely thirty, still a student, unsure of myself.“Well, I’m not asking, because I’m your boss for the summer. I was hoping you’d ask.”

“Mr. Kaplan, that’s not my usual style. As for discretion -” I lean toward him “ - yes, I think discretion is called for. I don’t want anyone to think I slept my way into a job.” I want so badly to appear sophisticated and worldly to this man, but being forward isn’t my usual style.

"Boldly presumptuous of you to cut to the chase and get to sleeping together. I was, very innocently I might add, hoping you’d like to go on a formal date. As for becoming my lover -” He looks into my eyes, then his eyes sweep over me head to toe “ - let’s see if you can earn that position.”

My face feels very warm, and only partially in embarrassment. He wants something, and it’s not the draft of a contract on his desk tomorrow morning. So why the tease?

Then I thought of a clever come back.“Oh, no? Then perhaps we should call it a night? Maybe we can have a Shabbat dinner later?”

“I wouldn’t go that far. Let’s get out of here?”

It’s so late that the fog has cleared. Clear nights like this are colder than the ones where the usual blanket of fog covers this city by the ocean, but you still can’t see the stars because of the light pollution. I shiver in my wool peacoat. Ezra offers me his, which I don’t accept. I ball my hands into fists and shove them into my pockets. I turn my shoulders inward, closing myself off from him, to make this awkward conversation easier to bear.

He grabs my attention when he puts his arms around me, then pulls me in. I look at him, and smile. He smiles back, before lowering his head and his lips touch mine. My body reacts, separate from my conscious will, and my body urgently pushes against his. It’s better than anything I’ve fantasized or dreamed. I’ve never been kissed so thoroughly, felt such intense chemistry with someone before.

That kiss shifted something between us. I’m looking at him in a different light, and I want him. I don’t know if I’ve ever felt such an urgent need to have someone fill me up.“I want to do things no man has ever done to you, to make you feel like no one has before,” he murmurs. “Let me take you home and show you what I mean.”

“What does that mean?”

“Exactly what I’m saying. Don’t play naive.” He’s still speaking softly, and the huskiness of his voice betrays his arousal. But I want this too. There’s something so fucking hot about a man you’re already attracted to taking charge, showing just how badly he wants you.“You said things no one else has done to me. I want to know what those things are.”

“I’d rather show you. And I’d rather not discuss what I’d like to do with you on a public sidewalk” He smiles, a mysterious half-smile that gives away nothing. “I won’t hurt you. Do you trust me, Rachel?”

I don’t doubt his promises of giving me pleasure and not hurting me, but I wonder how wise it is to agree to something without knowing the terms of the contract. But the thought of him taking control is also so sexy. What the hell, I think, as my hormones and lizard brain drowning out logic, why not just go for it? We’re both adults, I only have a few weeks of his mentorship and then nearly a year away from the office. Maybe it’s madness, absolute insanity to do this, but I really want to.

“Yes, please, yes.” He smiles again, conquesting, triumphant. He looks genuinely happy in the dim light, and I’m happy I made him happy. He runs a hand through his waves, shakes them loose, and kisses me again.

I want to keep making him smile in that way. And I realize, all at once, the most obvious thing: I really do like him.And he’s kissing me rapturously and rapaciously, and I am thinking about something altogether different. I laugh. “It might be more fun to continue this in your bed instead of a cold sidewalk.”

“I’ll be the one telling you what to do.”

“Yes, sir,” I say, lightly, while laughing.He looks at me like he’s starving, and I’m not just a snack but a whole meal. “Thank you.”We somehow survived the drive to his place without tearing each other’s clothes off.

But once we get there, everything changes. We take off our coats and shoes, then Ezra closes and locks the door behind me. He grabs me from behind immediately, one arm around my waist and the other twined in my hair. He pulls my hair, lightly, then just hard enough that gasp, momentarily breathless. My brain goes blank. It feels…possessive and controlling, there’s something violent in it.

“You’re such a horny whore, aren’t you? I had no intention of bringing you home tonight. But you’re just such a desperate slut. Now here you are, and I’m going to give you what you fucking deserve.”Then, everything snaps back into color and feeling. The energy he’s giving off is almost pitch black. Maybe the darkest power I’ve ever felt from a man, and he’s practically shimmering with it. Oh god, oh god, please, please don’t let him hurt me.

“What are you doing?”

Whatever the hell he’s up to, I don’t want it. It’s going to be terrible. I could feel how terrible in the way his hold tightened when I shifted against him. I squirmed, but his hold tightened. There was also his growing excitement, the hard length of it pushing against my ass. It scares me, how he can be so calm, how even in a state of high lust and excitement he maintained this control. I need to get away, I need to run, I need - I scream in fear, and his grip in my hair tightens. I writhe against his hold. I try to kick him, but he’s behind me. He easily outsmarts me, moving his leg away with a calm, almost feline grace and casualness. I’m so stupid, so pathetically helpless, as I thrash against his hold, whimpering in fear and moaning with arousal. I’m no match for him.He knows his power and my helplessness so well that it makes him chuckle in amusement at my frantic and helpless attempts to get away. “Oh, go right ahead, pretend you aren’t a fucking slut that wants her boss’s cock in all three of those holes. Pretend you can fight me off. Pretend like you don’t want it this way,” he purrs in the most evil tone. I mean, though, I do want it.

He pushes the length of cock against me again, as if making sure I can feel what he’s going to fill me with. I try to throw my weight against him. He chuckles, low, amused, and I swear his cock is like a rock. I shudder as I realize how he got harder when I fight back and by my frantic helplessness. I’m his prey, and he’s playing with me.

But. But, I’m getting high on the fear. I’ve always liked things that scare me, like roller coasters when I was a teenager, or something like a horror story. When I read a horror story, I’d be surprised to realize how wet I was getting. Or when I got a second piercing in my left ear, I was horny that I got home and got myself off to the fear and pain I felt when getting it. And then fantasized about more fear and pain for the rest of that week. Add to that the similarity to it that echoes the rest of my life: challenges thrill, arouse, and intrigue me in different ways.

With this type of sex, new to me in reality but I fantasize about it a lot, it’s something about the roller coaster of emotions, excitement shifting to fear shifting to relief that you can handle the fear and pain which then shifts back to excitement - it’s so arousing - he’s like that, with the arousal factor especially amped up times ten.

He pulls me upward by my hair, so I’m standing on my tiptoes, squealing in pain as my hair is tugged and I’m lifted so I’m struggling to stand. His voice drops to a menacing, condescending whisper “I can smell your wet needy pussy. I know it deserves a thorough fucking. That ass, though, I might start off with it. I’ve wanted to bend you over and take you so many times. Imagine getting fucked in both of those holes, like the little whore you are.”

Hell. No. I was not going to let him fuck me in the ass. Absolutely, positively not.

“No, you’re not going to do that to me. I’ve never done that, and I’m not about to start tonight. You let me go, NOW.”

Oh god, I shouldn’t have told him that. He pushes the hard length of his excitement and amusement harder against me. Oh no, please, no, no…I scream again. I hope his dick rots off and he goes deaf from me screaming in his ears.

“Oh, Rachel! Have you never had your ass fucked?”

Maybe my mind is going to break. “No! And I’m going to keep screaming so that all your fucking neighbors hear, and then I’m going to march myself into your boss’s office tomorrow and - “

“Oh, I’m sure my neighbors have heard enough. And then what, Rachel? Tell my boss that you promised me you’d be discrete because you didn’t want to ruin your career? You voluntarily came home with me. You know you want it. I can smell how desperately you want it. I bet if I touched your pussy - ” His voice is so amused and calm that it’s like he’s talking about the fucking weather. It’s evil, that voice compared to what he’s saying, the casualness with which he maintains absolute fucking control.

“No, don’t do that! Fuck you! Let me go, asshole!”He chuckles. “Oh, don’t worry, we are definitely fucking tonight. Don’t worry boo, I like it rough too. I’m not mad at you.” He grins. “Even though you are being a very bad girl, you’re still getting my cock tonight.” His hand is still in a stronghold in my hair while he fiddles with the button on my pants, undoing the zipper, tugging them past my waist and ass easily.“No! Stop! I don’t want to! You’re a monster, a demon! You’re awful, horrible. You let me go!” In response, he lifts me off the ground by my hair, and I yelp.

“Awww, it’s so cute, the way you’re pretending you don’t want it. I’m really enjoying this game of hard to get that you’re playing.” His other arm is around my hips, and I’m trying to aim so I can kick high and get him on his goddamned balls. He’s got a good ten inches and 70 or 80 pounds on me, and so, he easily swings me so that I’m cradled like a baby in his arms and he can carry me. His wavy hair is loose and wild. He’s the cat here, I think frantically. He’s like a black lion, and I’m the prey he’s taunting and teasing. Then, he lowers his head a little, sniffing me. “Mmmm, delicious. Naughty girl, I don’t even need to touch you, I can see that you got your panties wet all the way through.”

“Stop! I don’t want to! I’m scared of you, and I’m so scared you’re going to hurt me, please just stop, please don’t hurt me, please -” With that, I burst into tears. And he’s so calm and controlled, which makes me cry even harder.

He drops me onto his bed, covering the length of my body with his. His wavy hair falls over his face, framing it like a black mane, and it makes him more achingly beautiful to me. He’s pushing his hard length against my soaking wet pussy, and it’s so warm, so close. I don’t want to, but I arch my hips toward him like a woman possessed.

“Shush. I know how you need this, how badly you crave submitting to me. You’re a desperately needy little slut, and you need to be forced, hurt, and pleasured. I promise I won’t force upon you anything you can’t handle. Trust me. You’re so beautiful and brilliant, and I like you so much. If you really want to stop: I’ll slide my hand into yours sometimes, and I want you to squeeze it back. If you don’t squeeze, I’ll stop, so I’ll never really rape you or force anything on you. I promised I won’t hurt you. You want this, don’t you? You trust me?” Even this, the power he gets from reassuring and calming me, keeps his cock hard.

I moan, and his cock is pressed between my legs. I’m caught, the perfect prey because I want him to devour me. He pushes one hand between my legs, touching my uncomfortably wet panties. My body acts before I can think, and I’m thoughtlessly opening for him. It’s madness, isn’t it? My nerves all feel like they’re on fire. I’m agreeing to have anal sex - which I’ve never had - and god knows what else with my fucking boss. I must be fucking out of mind, insane, because I say -

“Yes, Sir.” I know that calling him that is acquiescence.

“Hmm, I like that. Someone likes being called a whore and the thought of both of her holes getting fucked.”

“No, no! You can fuck me the normal way. You. Are. Not. Fucking. My Ass.” He slips his hand into mine. I squeeze back, consenting.

He pulls out a switchblade knife from a side drawer. My heart leaps up into my throat in fear. I try to reach for his hand, to signal no, but he moves away. His face is so calm, with only his eyes wide to express - oh, god, his eyes scare me a lot. They’re practically glowing. I know he’s going to take a lot from me to satisfy that lust, and I know it will be satisfied tonight. I can only read his lust through his eyes and his cock. The rest of him, his playful smile, the veins of arms crossing in gorgeous patterns over them as he crosses them over his chest to pull off his shirt, convey a sort of calm power, the kind that’s stronger and more frightening in its quiet calm. His arms are almost too much, too beautiful, for me to bear. His posture is so straight and perfect, the rest of him maintains the same perfect control he has in the office. Damn him for being so fucking attractive to me while also being such an ass.

He flips open the knife, points it toward me. “Strip.”I obey without thinking. Heart thumping and fingers trembling, I get off his bed, then take off my sweater. His glaze is so intense that I’m more scared of him than ever. Maybe he could burn me with his eyes alone. I’m so much smaller than him. His eyes linger on my swelling, heaving chest, taking it in, clad in black silk. Then my small belly, hips flaring out, legs soft and firm with some muscle, and I pull off my socks. I hesitate. He fiddles with the knife, reminding me of its presence. As if I’d forget. I slowly pull down my bra straps, then the cups. My breasts are round, nipples shrunken because they are so hard they almost ache. Slowly, I pull down my black silk panties. I look down, noticing how soaked I am, seeing one sticky strand of wetness as I pull them off. He’s holding his phone and the knife.

“Fuck you!” I say after he clicks a quick photo of me, naked with his bed behind me.

He covers the space between us in a single bound, and pushes me back on the bed. He pushes my legs apart, so I’m naked and exposed and he can see how humiliatingly soaked my pussy is. Another click.

“Oh, Rachel, look,” he says, showing me that photo as casually as he’d show me a vacation photo. “Look at how your pussy lips look so puffy and soft, and look at how you’re fucking dripping on my bed. It’s fucking cute, your pussy is adorable.”

Such a patronizing jerk. I glare at him. Then sigh. I don’t have much of a choice, do I? “Please just - stop. If you let me go, I won’t tell anyone. Please don’t show those photos to anyone. Please. I’ll be a good girl and - please.”

He gets on top of me again. I push against him with my hands, but he just grabs my hands and pushes them away. “What’s the point, Rachel? As if you could fight me and win.” I stare at him with tears of helpless rage in my eyes. Rage and fear of those photos.

It’s humiliating how easily he parts the secret lips and his fingers slide right into that slippery hole. I screech again, and buckle against his hand. He finds that soft ridged part, and rubs it. I scream again, but this time it’s because an orgasm tears through me like wildfire. “Such a fucking slut for me,” he whispers in my ear as my muscles contract around his fingers.I must be a slut, I must be everything he tells me, to be forced the way he was forcing me and to be dripping and cumming for him. To be getting off on his degradation and humiliation the way I just did. I was so desperate and aching for whatever else he wanted to do to me. And he - he - I mean, I don’t know what you call someone who enjoys my fear and degradation, enjoys having me damn him to hell while knowing that he had so much power and control in the game we are playing. It seems to me something beyond domination, but I don’t know. All I know of this type of play is what I’ve read on the internet. I thought it sounded pretty hot, but it’s even better than it sounded. His slut, his plaything, I think, I sink into that feeling, weak and relaxed.

While I’m still trembling, he cruelly pinches my clit. Hard. I - it’s like - I’ve never felt that way before. It’s - my entire brain goes empty and blank, and this wave of extreme heightened feeling floors me. I gasp, then laugh. I sound like a maniac, even to myself. It’s just so - was so amazing. Oh my god, in the best way possible. It’s the thing that breaks me, that makes me his personal whore in a way I’d never wanted to belong to anyone else. I’d never felt so perfectly in sync and attuned to anyone. How could I feel this way so soon, after only knowing him for a few months and with this being the first time we hooked up?He squeezes my hand, and I squeeze back, hard.“Did you like that?”

“Yes, Ezra…” That feels wrong. “Mr. Kaplan, sir… yes, I did.”

“Ah, you can orgasm from me pinching your clit? Don’t you fucking move, needy little slut,” he says, picking up the knife again and laying the blade flat against my cheek. I lay back, quivering with the afterthrobs of the orgasm and shivering in fear. I’m too far gone then to notice that he carefully keeps the sharp edge away from contact with my skin. He vanishes for a moment, and returns with - something like six leather cuffs and dramatically pulls back a curtain to reveal - an entire wooden x-cross. Who casually has an entire cross sitting in their bedroom behind a fucking curtain? He - this - he does really know what he’s doing, and he must really love it if he owns that. Dear god, what had I gotten myself into?

“Please don’t,” I whisper. He ignores me. “Please, please, don’t put me on that thing, I don’t, I - what are you going to do to me?”

“You need some discipline, my little burgeoning submissive. Now, be a good fucking slut and learn to take what I give you.”He tames his dark wavy hair, pushing it away from his face, then caresses my face with the blade of his pocket knife. I go still in fear, like I can’t breathe. The cuffs go on my wrists, ankles, and thighs, and he secures me to the cross, facing away from him. It’s so, I don’t know how to explain it, but it makes me so happy and excited. Like sort of giddy and giggly. Which is nuts, because I’m also tied up and he has a knife, and he wants to fuck my tight, virginal ass.

I hear his flogger slicing air before it lands on the center of my ass cheeks. A hot searing pain spreads across me. I startle, and shake in my restraints. He comes around, facing me, and slips his hand into mine, and I squeeze back. And again. I shake, and my scream turns to laughter, a short terse laugh that winds me as a third blow lands. He stops, and I hear something behind me. “That was just to help bring blood to the surface of your skin, for this…” A click, loops - oh god, he’s taking his belt off. Then I hear the soft rustling of fabric. I hear him slide the leather strap through his hand before he uses it to strike me. It hurts just as much, though less of a sting, but more humiliating. Tears tremble against my closed eyelids, then spill over. One, two, three, in exactly the same spots as before. Such intention, in the precise placement and each blow being exactly the same level of impact. Four and five. I yelp and cry out. I’m more scared of him now than ever, because he’s so perfectly in control of himself with his belt. How, even, when he’s hard and horny?“You’re so mean.” I say through some combination of tears and breathless laughter.He’s paused to listen to me. He comes around, cradles my face. “Oh, does it hurt?”

“Yes! It hurts a lot! Please stop!!”

“I do like hearing you beg and curse me to hell. You’re so shy and controlled, I love bringing you down to this.” And he’s normally very reserved, professional, and an ideal mentor. Maybe he’s just mentoring me in something new. I’m his captive, and he’s tormenting me for his pleasure. All of my senses are heightened. Another perfect stripe with his belt. And another. I hear his feet as he turns behind me with his almost cat-like gracefulness, the belt singing through the air before it lands that second blow. He’s playful, and there’s so much joy in his movement. Every stripe follows a pattern, from the top of my ass down and back again, each blow landing perfectly. How was that level of precision and accuracy possible, especially when he was so aroused? How could he be that disciplined, that controlled? It’s so incredible that I know how safe I am with him, with the level of care he was giving me. The thought makes me smile, and he caresses my ass. He goes just a little harder. I cry out, and the weirdest, lovely feeling comes over me. It’s like I’m floating, maybe flying. I laugh, a sort of spacy giddy giggle. He keeps going. How does he know what my limit is so well, how does he know to hover right over it? I want to laugh. Maybe I’m going crazy. But I don’t feel crazy. It’s so good, it’s amazing, it feels so intimate, to see him like that and let him see me like this, to reveal our darkest, most forbidden desires to one another. I want more of it. It’s better than just plain sex.

“Please, can you be gentle? I’ve never done this before.” I whisper.

“Hm, twenty belt strikes. I’m glad to have introduced you to this.” He dismounts me from the cross, then gathers me up in his arms again, and kisses me deeply. “And Rachel, I am being gentle.” It’s very sweet, but I can feel his excitement. Oh, no. No, I know what he wants, no, no…Then I’m face-down, ass-up on his bed, and he’s straddling me while cuffing my wrists to his bed. I try to push up, but he cuffs my thighs and ankles. Okay, maybe it’ll be okay. Please don’t touch my -He’s spreading my ass, and I can’t stop him. He’s rubbing me with what must be lube.I can’t bear this. Everything felt so lovely and floaty and surreal, and now we’re back to everything being almost too much and he’s being an awful demon. Wait - do I really think he was being lovely when he was beating me with a belt? I howl, in no small part because I realize how I’m bending to his control. It was bad to want to be controlled, hurt, and degraded. And how desperately I wanted him to be pleased with me. Oh, no…

“No, no, everything was so floaty before, and now I can’t, I’ve never done that before, and I can’t start with that. Please no….”

“It’s called subspace, Rachel, and I have so much more to teach you. Please no, what?”

“Don’t do that, please don’t.”

“Oh, but what am I doing? Use your words.”

He’s such a condescending ass! A hot flood of shame fills me, and drips from my pussy and probably on his sheets. “Please don’t touch my asshole.” I whisper, teeth gritted.

“Now why would I stop, when we’re enjoying it so much?” It’s so fucking good. It’s a weird good, like, his finger shouldn’t be there, it feels so unnatural, and dear god, it’s so good, so taboo, so forbidden, which just makes it better.

When he pauses, I try to push up. He pulls my head up by my hair. It hurts, and I screech in pain.“You were very clearly enjoying taking my finger in your tight little asshole. Look at your pussy. I can fucking see what a wet, slimy mess it is.” My eyes go wide as another rush of wetness pulse through me. I want this so desperately that it’s embarrassing, and yet, I don’t want this at all. I’m horny for it, but I’m so, so scared of it. And what if I can’t handle it? What if it’s too much, will he despise me if it is? I want so badly to please him, and I want so much just to get away from him so that I don’t displease him, so that I don’t get hurt.

“Please, please, what if I can’t, what if it’s too much, what if - ”

“Shhh, I’m the one in control here. I want to break you until you’re my adorable little fucktoy, my personal whore.”I shiver at the thought of breaking, breaking me, molding me to be his personal whore. Then he’s pushing something cool and slippery into me…it’s heavy, cold…glass…it hurts deliciously.“What - what is that?”

“It’s a glass plug. Have you ever been plugged before, Rachel?” Then, it gets wider, it’s too much, I can’t take it, it’s too big for me, no, no, I clench my hands.

"No, stop! It hurts, please stop! Nooooooo.”

“Shhh, it’s all the way inside you now. You took it just fine. If you relax, it’ll hurt less.” I shudder, trying not to sob. It’s too much, altogether too much, I’ve never been put on a cross, or tied up, or hit with a belt, or had a plug in my ass and he’s somehow done all of this to me in a span of no time.Then I feel his hand, warm and comforting, slip into mine, and I squeeze back. He gently climbs on top of me, and wraps his arm around me, so that we’re both on all fours.

“I know it would be more sexy if I kept going in the same vein, but I want to make sure you’re okay with, you know, what’s next. But even if you want to stop now, this was worth the risk. You’ve made me very happy, little girl.”

I sniffle. These tears are a different kind, and I feel - I don’t know - a feeling of happiness and care that will linger after this night is over. “It’s so hot that you checked in and asked. I - I’m enjoying this, it’s really good. Thank you.”

“What a gift, Rachel. You’re sure you want to give it to me?“

"Yes. Would you like me to beg you to - fuck my ass, Mr. Kaplan?”

“Oh, you just did. Such a needy slut.”

“No, I didn’t. I - “

“Too late. Your tiny, tight little asshole is going to take my cock. How do you think that’s going to feel, if it was so hard to take a little fucking plug?”

“No, no! Fuck you, no, stop!” He gently pulls the plug out, rubs me with more lube, tears the wrapper of a condom. “You’re - no, no!”

“I’m what?”

“You’re a monster, you’re awful, you’re the worst! I hope your dick falls off!”

“Oh, do you? But baby, how would I fuck that needy pussy and ass and mouth then? Mmm, how does it feel to know you’re about to get the ass fucking you just asked for, the one you’ve probably fantasized about, my little anal whore?”

He’s practically purring. His cock is between the halves of my ass, gently pushing at the small opening there. Panic sets in. Oh my god, he was right, how much would his cock hurt if I could barely take a plug? No, I can’t do this, it’s going to be too much, I can’t handle it, it’ll - no.

“No, no, no! Stop, no, please, no, stop, no…”

Very slowly, the head of his cock inside of me eases into me. I can’t bear it, it feels like it’ll rip me in two, it’s too much, he’s too big, I can’t, it hurts so badly. “No, god, please, no, you’re too big.” He slides in and out a bit, more lube. I’m nearly sobbing, I can’t stand this, maybe my asshole is just too small, then another little push, and I swear I’ll never be the same.I shudder, hard. The thickest part of the head of his cock is inside that tight, barely yielding ring of muscle at the entrance of my ass, and the worst is over. He’s slowly pushing into me, in and out, inching deeper with each thrust. And then, it starts to feel good. I mean, really good, that pleasure tempered by a bit of searing pain. I’m barely aware of that I’m moaning, gripping his sheets with my fists, helpless under him, as he fucks that tight little hole. That pain makes me feel more alive to the pleasure, more sensitive, and his cock feels so fucking exquisite, so perfect, and I hear him groaning a bit in time with my moans, our bodies entwined and locked together…

“Do you like this?” I put my face down in his pillow, moaning. He grabs my hair, “I asked you a fucking question.”

“Yes, Sir, yes, I like it.”

“Tell me what you like.”

“I - I like you fucking my tight little asshole.” I say it, then I screech, face down into his pillow, forced to name my degradation and shame, and naming the desperate pleasure I’m taking from it to please him. With that, I tip over, the muscles of my tight sphincter tightening on my cock, and my empty pussy clenching, and I’m moaning in pleasure.He groans above me. “Did you just fucking cum on my cock in that little ass, sweetheart?”

“Yes, Sir,” I quiver weakly, as he speeds up, and reaches down, pinching my achingly wet clit.“Yeah, you like that? You like having a thick, hard railing your tight little hole? You took my cane on your ass and cock in your ass before I fucked your throat or pussy, before I ate you out. God, you’re the most desperate, cock-hungry whore. So fucking easy. Such a damn slut for my cock.“ He pinches my clit.

And it’s so exquisite, so fucking amazing, and I’m hit with another one of those mind-melting orgasms, and I put my face into his pillow so I don’t break his eardrums as I squeal in ecstasy, and I hear the triumph in his low laughter, his little growls of pleasure as I tighten around him, my pleasure feeding into his pleasure, in a loop of reciprocal pleasure that’s better than anything, both of us in sync and entwined. I’m moaning and squealing again, and he’s going hard and fast and his breath is ragged and hard, and he is pulsing inside me, so hard he feels like a rock inside, violent spasms as jerked, repeatedly, deep inside me, and god, his cock is so fucking good and I screech as tighten as he explodes…And he lays on top of me for a moment before withdrawing his cock, then he releases my cuffs, and pulls me into a stronghold in his arms. I lay spent in his arms, a bit overwhelmed, happy though everything feels a bit surreal. I suppose I could move, but I still feel as if I’m under his restraints. My mind is still shackled.

I feel an ecstatic calm, a little giddy, a tiny bit anxious. Did he enjoy that? Did I please him? I moan into his chest.“Everything okay?” He grips a fistful of my hair, using that hold to move my head so he can see my face. Ever the hunter playing with his prey, the dom with all the control.

“Yes, it’s good. Was that okay for you, Mr. Kaplan?”

“More than okay. You’re a very good girl, and you’ve given me so much tonight.”

“I have a great teacher.”

“I do mean what I said earlier, Rachel. I do really ‘like you’. And the sex was totally your fault, horny little slut.” He lightens on emotional charge of his words, then changes the subject very quickly. Still, my heart lightens, the anxiety dissipating. He must want more of me.

“My fault? You forced yourself on me!”

“Oh, did I? I seem to recall someone asking me if she could beg for my cock in her ass.”

“What, I - no. I begged you to stop.”

“Yes, you did that too. It was very sexy.”

“Sexy? What?” I playfully, lightly pummel his chest. He catches my fist, and pulls it to his chest. The way he’s looking at me makes me feel precious and beautiful.

“Hmm, I’m delighted to mentor you in this new way. God, finally. I kept wondering, does she, you know.”

“I’m delighted you’re mentoring me, too. How are you so perfect?”

“Am I, Rachel? Not a monster, mean, a demon? Or am I those things, too?”

“You’re right, I like both sides.” Shyness hits me again, and I bury my face in his chest so he can’t see. He tilts my chin up, so I face him again and he can kiss me again. Then he gets up, taking the plug and used condom with him. I snuggle into his bed.

“May I ask you a question, Mr, Kaplan?” I hope that’s the right way of doing things.

“Good girl. Sometimes I won’t allow you questions. You may ask this time.” My heart lightens again. There will be other times.

“How did you know that I’d like this?”

“I thought you were probably a sub the first time I met you. You looked at me in this way that was scared but excited. You’re easy to read. You’re shy and anxious, though you cover it well, especially when in the flow of work. And when you flirt with me, Rachel, you do it in a way that’s very submissive, you build anticipation and mystery in ways that give me power and control. ”

“What if -"

He knows what I’m going to ask. “We’re both supposed to be logical, but from the moment I first saw you, I wanted you to be mine. I knew you were something special. Through the last few months and tonight, I think we work well together. I also thought the best way to have you and to earn your respect was like this. I know it was a short session, and there’s so much more I want to introduce you to. May I take you out on a real date?”

“Yes, but you already knew.”

“I suspected.” His answer isn’t in words, and all the sweeter for it.