Where does pleasure end and pain begin? During the build-up to my session with Steve, that was the question that occupied my mind. The one he’d left me with at the end of our email chat and the beginning of my BDSM story.
We’d begun by discussing limits, preferences, experience and all the practical things that you need to cover off with someone before you step inside a dungeon with a commitment to submit. Steve tends to play in absolute silence—or as close to silence as one can get, at any rate, when you throw in the involuntary noises that people fucking are liable to make and the frequent cracks from whips, paddles and the palm of a dominant’s hand. So we corresponded about the session before it happened: I laid out my hard limits, and Steve took careful note. So far, so much to be expected. But it was the end of our email exchange that really fired up my imagination—I’m sure that was exactly his intention. He is very skilled that way.
Steve’s final email to me began by acknowledging everything I’d said in my last, assuring me that he’d heard what my limits were and wouldn’t push me beyond them. But then he switched tack, and the change of direction took me by pleasant surprise.
“Onto more important matters,” he wrote, “for me the most important matter: pleasure. We’ve talked about your dislikes and your limits and the things you don’t want me to do, and that’s vital. Your consent is paramount, always. But now, let’s look beyond consent and towards desire. Want. Need. In your final email to me, I would like you to lay out a series of desires. Tell me what you want. Tell me what you think about when you’re touching yourself. When we originally arranged this session, what did you hope might happen? Tell me your dirtiest dreams.”
It hit me like a jolt of electricity, zipping straight from the base of my skull down my spine to resonate in a pulsing thud at my clit. My dirtiest dreams. He wanted me to give him guidance on the things that kept me awake at night. The fantasies that had been playing around and around in my head ever since we’d booked a date to use that fabulous dungeon.
Somehow, even just sitting at my laptop in my sweatpants and a loose t-shirt, I felt naked. My nipples hardened against the soft cotton and I crossed then uncrossed my legs.
“Tell me your dirtiest dreams,” Steve had ordered. And I complied very willingly indeed. Two thousand words of compliance, in fact, pouring out the ‘I’d love it if’s and ‘maybe you could’s that had occupied so many of my waking thoughts. “Where does pleasure end and pain begin?” He’d asked in his final paragraph, and so I set my mind to that as well—detailing my yearning ache for that delicious moment when he might pull his hand from my dripping pussy, spasming with ecstasy around those lovely thick fingers, then land a sharp smack on my arse by way of contrast. Pleasure and pain—the latter so much more intense for the wetness on his fingers from my cunt. I barely noticed the time flying by as I laid out ideas—floggings and fingerings and the thought of being restrained while he fucked my mouth—and by the time I was done, not only was it dark outside but there was a growing damp patch on the inside of my knickers.
Where does pleasure end and pain begin? I had re-read my email so many times since I wrote it and squirmed with anticipatory glee as I studied Steve’s reply (a two-word message simply reading ‘good girl’) that by the time we met, I was practically trembling with desire to see where he would take the scene.
As always, I begin by dressing up. By the time I enter the dungeon, you could be forgiven for thinking I am playing the part of the femme fatale in a Bond movie. Stocking-clad legs, dark red lace suspenders, bold dark lipstick and earrings that sparkle under even the dim lights of the play space. Naturally, Steve starts by inspecting me. Walking around me as I stand in front of a piece of heavy wooden equipment, admiring every curve of my body so stunningly presented in that lingerie.
Inspection had been on my original list of requests and he fulfills this desire with aplomb. As he circles around me, tapping the paddle against the palm of his hand, I can feel the blood rushing to the surface of my skin, as if eager for the next part to begin. But Steve isn’t one to be rushed—he takes his time. Building that intensity by stroking me oh-so-gently. Cupping my tits in his palms and running his thumb delicately over my lips as he looks into my eyes. I have so much time while he’s doing this to ponder our discussion from before. Asking myself again that age-old question: where does pleasure end and pain begin?
I breathe faster and deeper as he runs the paddle over my body. Tapping it lightly against the crotch of my knickers (definitely still pleasure, it resonates along with my heartbeat, and I am so so desperate to take these panties off). He still doesn’t smack me, though. I’m almost itching with a need for him to do so, but he wants to take his time. He makes me press my lips against the paddle gently before kissing me himself—deep and intense and powerful. Moving the paddle itself to my tits just to let me know that I might get smacked there if I’m very lucky. I feel so wanton in that moment that I almost groan.
Stashing the paddle in his belt for later, Steve delivers a few light smacks to my bottom. Then a few more to my crotch. He manages to weave these little warning taps so skillfully in between kisses and caresses that I almost don’t notice he is sliding down my knickers and angling me towards the huge wooden stocks that dominate that dungeon. The stocks I am so eager to be locked inside…
Even as he guides me to the right position—kneeling and bent over so my neck rests against the wood and my wrists are clamped tightly either side of it—his movements are dripping with care and kindness. Scooping my hair out of the way with gentle hands. Kissing and touching my lips, my tongue. It’s almost as if I am a delicate doll, being positioned for his amusement but ultimately incredibly valuable. Precious almost.
That sense of being precious carries through to the first whack on my now-naked backside. I know that sounds strange, but this is all part of the pleasure/pain dichotomy: the first smacks that he delivers to my pale skin are unquestionably pleasurable. Just hard enough to register, shaking the flesh of my bottom as he delivers them, but gentle enough that the sensation causes my face to crack into a smile of delight. He kisses the places he’s just hit, but at this level of softness, the smacks themselves are kisses of a kind, anyway. Little brushes of agitation across my flesh.
Now comes even more of what I desire—his thick fingers, wet with spit, massaging the folds of my labia and delving deeper as he works his way towards the centre of my lust. Rubbing gently at the skin that’s exposed now I’m kneeling and vulnerable before burying his face into me and licking more. Sliding his thick, solid big dick from the fly of his trousers and pressing it against me, almost like he’s testing to see if I’ll wriggle towards it and try to persuade him to enter. Vigorous fingers and that tempting cock plus that insistent tongue… it’s enough to almost make me cry out, but I’m a good girl as per the email so I bite my lip and smile and sigh. Steve alternates these delicious treats with the trick of a hard paddle smack, and now I’m beginning to see where the line between pleasure and pain might lie.
In my email about desires, I had asked him to fuck my mouth. So when he moves around to the front of the stocks and that powerful erection bobs into view, I’m sure you can imagine the eager throb of longing that resonates in the pit of my cunt. As he slips the taut head of his prick between my wet lips I begin to tease and suck on it gently, like I’m taking my time. Clearly, far too much time, though, because it doesn’t take long for him to take over—removing yet more control from me as he thrusts it deep into my mouth. Bracing himself by gripping the heavy wooden stocks with both hands, I can hear the chains jangling with the stress of movement as Steve focuses on shoving himself nice and hard into my open throat. His dick is so fat, it stretches my lips wide. Gripping those stocks good and tight, Steve fucks upwards into my wet mouth, and I yawn as wide as I can to accommodate the girth of it.
Pain or pleasure? This one’s pleasure, for sure. Though the wood of the equipment bites into my neck and wrists and the head of his prick hits the back of my throat, the overriding sensation is one of pure pleasure—being used as a hole for his twitching cock, just pure spit and warmth and willingness. Sighing with pleasure, fucking harder into me, he lets out these gorgeous little moans and sighs and gasps. He’s controlled, as always, but I feel a kick of pride as I sense him start to lose a little of that control—not much, just the tiniest bit—as he grabs my hair with one hand, closes his eyes and murmurs, “Yes. Oh yes.”
Perhaps that loss of control is a little too much for him, because the next thing I know, he’s pulling out, letting trails of saliva slide from my lips to the meaty girth of him, breaking and running down my chin as he retreats. Kneeling on the floor, he kisses the hole where his cock has just been, and suddenly I feel precious again. How miraculously swift that switch can be! I am almost giddy with the joy of it. From ‘slutty’ to ‘special’ in mere seconds.
Moving around to the rear of the stocks, where my naked bottom is presented on a glorious show for him, Steve clearly decides that the time has come for a little pleasure of his own. And who am I to deny him? After all, not only did I write ‘restrained and fucked, pretty please’ right there in black and white on my list of desires, but it’s not like I’m going to escape any time soon: my wrists and neck are firmly secured in place, so all that is left for Steve to do is decide from which angle and how hard he will fuck me. He toys with me for a while first, pressing the head of his cock against the ache at the entrance to my cunt, then slightly deeper in my slit until I’m almost melting with a need for him to push it all the way in. When he straddles the spanking bench and slides in, right to the hilt, I can feel it satisfying my pussy more and more with every single inch that slips inside. He gets one knee up on the bench for better purchase, and I moan greedily for as much as he can give. Fucking me with short strokes interspersed with slaps, he rattles those stocks hard enough that I wonder if anybody outside might be able to hear. I love the way his dick feels inside me, and I’m so desperate to be able to fuck back. But I’m chained into immobility, so completely at his mercy, that all I can do is moan and gasp as I accept as much of his big cock as he’s willing to give me, while he smacks and grunts and moans ‘oh yeah’ with a vigour that makes my cunt pulse. Getting more energetic now, ploughing me with even greater force and power, Steve plants both hands on the small of my back to form an arch as he drives downwards, causing my tits to jiggle and the stocks to clank at the sheer force with which he pounds me.
It’s enough to make a girl’s head spin. Even a good girl’s head. And of course we’re still firmly in the land marked ‘pleasure’. I can see the line that represents pain, but it’s still a way away—more whip marks and animal fucking is required before I set even one foot over it. I’m confident that Steve will take me there, though, and as he switches up the position, I can already see that my desire to take as much of his cock as possible will be fulfilled… eventually.
Steve flips me over and puts my wrists in the stocks behind my head. My neck is definitely grateful to be free, though I’m already eager to be trussed up a little more—a need that is fulfilled almost instantly when he locks my ankles tightly into straps which attach to a spreader bar. One or two more deft movements later (he really does know his way around this dungeon), and my legs are hoisted up—splayed open and ready to receive whatever pain or pleasure he decides I deserve.
I do, so I hope it’s both.
Lying on my back, my view impeded by my thighs spread above me, I can’t tell if I’m in for punishment or gratification until the moment when his tongue touches me. The thrill of it zaps through my core just as it did when I first read Steve’s words ‘tell me your dirtiest dreams.’ He begins by tonguing my ass, then slides upwards over my cunt to where that electric sensation resonates in my clit. But I am not subjected to this delight for long, it’s time for a whipping. And gleefully, I relish the sting of the flogger as he swaps out literal licks for licks with those thin leather fronds. Thwack, thwack, thwack, one after the other landed perfectly on the meat of my bottom, making me squirm and sigh. Steve alternates teasing, gentle brushes with more intense, genuinely agonising smacks, and I know now that we’re dancing on that line between good and bad, pleasure and pain, joy and … well. I almost said ‘sorrow,’ but it’s not really, is it? I love the pain—I yearn for it. It’s this which I’ve been hoping we’ll build up to. It just so happens that he’s done it so cleverly I barely notice the point at which we dance over that line and into the darkness.
Alternating between eating me out, whipping me, and finally sliding the thick head of his prick between my eager pussy lips, Steve has me dizzy with need. And he needs now too, I think. I can hear him moaning ‘oh yeah’ as I crane my neck to watch him wet the head of his cock against my dripping cunt.
Oh yeah indeed. I almost gasp ‘please’ but remember my instructions to stay silent if I can—I plead with my eyes instead and he plunges in. Then out again, maddeningly, to tease my clit with the shaft. Then back in again, relieving the ache of desperate want. That is all I can think of right now.
Leaning forward to grab my hair for purchase, Steve gives me the utter brutality I think he knows I’m craving. He fucks me so fervently that my tits hurt when they jiggle, so intense is the power of each thrust. In and out, each stroke punctuated by a rattle from those chains or a thud from the joints in the wood. A gasp from me or from him, I can barely tell which now—my brain is muddled and confused as I lurch closer and closer to the ultimate catharsis.
Steve senses I am almost there, pulling out just before I come so he can bring me to the peak of my climax with his fingers—shoving inside then pulling neatly against my g-spot so that I squeal and clench tightly around him. I feel each wave of my orgasm as if he’s yanking it out of me. One wave after another, being tugged from deep within me by those powerful hands. Over and over again. Shudder after shudder. But there’s no time to rest. Instead, he plunges in again—this time with one hand lightly resting on my throat, reminding me that I am still restrained and his until he’s done with me. Fucking viciously and hard, alternating gripping the spreader bar to yank me down to the base of his cock, and taking swipes at my vulnerable, tender bottom with that lovely leather flogger.
Then, as soon as I think he’s about to come, he changes tack—releasing me from the spreader bar with a gentleness that stands in stark contrast to the aggressive power of his fucking. Softly, he removes the ankle straps and then unlocks my wrists from the stocks. I am back to being that doll again: cherished and adored. Treated with such reverence that I almost forget the wanton slut who was—just two minutes ago—spreadeagled and flogged and fucked while she gasped and moaned with pure need. Now he looks into my eyes as he fucks me. One hand on my throat to remind me that I’m his, but this time it’s mostly his gaze that pins me in place. Until I try to touch myself, that is, when he clearly decides I’ve had too much pleasure for one day and straps my wrists back up and behind me to prevent me from misbehaving further.
Straddling the bench, thrusting in and out of my cunt with determination and power, Steve looks at me like I am a precious treasure, and I stare back at him in turn. I realise by now that I’ve forgotten which parts are meant to be pleasure and which parts are meant to be pain. The cuffs bite my wrists, but I barely notice the thrill of satisfaction in my pussy. My bottom smarts from the whipping earlier, but the pulsing urgency of his thick cock sliding in and out of me cannot fail to distract me from something so inconsequential. Grabbing the stocks, Steve fucks me firmly and steadily, angling himself so that each stroke makes me gasp as it reaches full depth.
When he comes, it’s like he’s shoving the first squirts of spunk right up against the walls of my cunt, and I close my eyes in ecstasy. Pulling out, he allows the final drops to fall on the twitching wet slit of my thoroughly-fucked body before toying with me by sliding in and out a couple more times.
In the aftermath of this all-consuming scene, I run through my list of desires, noting which of those he ticked off and which ones he’s saving for next time. And still, I think, as he releases me reverently from my final bindings, I haven’t been able to pin down the answer to his question. Where exactly does pleasure end and pain begin? Maybe, for me, those two things are one and the same.
The End.
