Jenny's Journey

"Now, pet, are you ready to see what tonight has in store for you?"

I am seated at James's dining room table, working on my third glass of red wine and trying to force myself to eat a bit more of the delicious salmon and lemon risotto he has prepared for us. We've spent the last two hours having a fairly regular second date: he asked about my day, I asked about his, we shared a few funny childhood stories and a few painful ones. Other than the intense butterflies fluttering around my stomach, and the jolt I felt when he placed his hand in the small of my back to lead me into his house, there is little evidence that this is anything other than the early stages of a normal relationship.

Well, almost. There are a few hints that this is not a normal second date, though they are concealed from view beneath my clothes. A few hours ago, James had called me at work.

"Are you alone?" he had growled huskily when I answered.

"No," I said, glancing furtively over my cubical divider.

"I suggest you find someplace private. I'll give you 30 seconds."

I jolted out of my seat, drawing a few inquisitive looks as I overcorrected and, with unconvincing nonchalance, walked out of the office. How many seconds had passed? Ten? Twenty? Could I make it to the bathroom down the hall before he reached thirty? Only if I ran, which would draw unwanted attention from the private offices on the way. Instead, I ducked into the tiny supply closet next to our office and shut the door, just as James said, "Time's up. Where are you?"

"A supply closet," I whispered.

"Good girl. Now, let's get you prepared for our date tonight. Take off your panties."

I wordlessly complied, hiking up my tight black pencil skirt and pulling off my pretty lace panties, chosen especially for our date. "Done."

"Done what?" His voice was hard, and I realized that I'd messed up.

"I'm sorry, Sir. I've taken off my panties, Master." I was whispering as quietly as I could, but I silently prayed that no one walked by or, God forbid, needed a package of staples or a piece of letterhead. The closet door didn't lock.

"You'll be punished for that later," he said, and I felt a familiar aching in my pussy. "How long has it been since you've cum?"

"A week, Sir," I said, recalling our incredible first date, blushing at the memory of my naked body, humping his black leather shoe.

"Good. Have you been touching yourself without cumming?"

"No, Sir. I don't know if I can touch myself without cumming."

He moaned slightly, and I thrilled at the effect my submission was having on him. "Alright slut," he said, his voice thicker and deeper than before, "we'll have to work on your control. Let's make sure you're good and aroused first. Are there any binder clips in this supply closet of yours?"

My heart pounded in my chest as I spotted exactly what he was asking for—small, medium, and large butterfly clips in a box in front of me. In a small, terrified voice I replied, "Yes, Sir. Three sizes."

"Choose the smallest," he said, and I could hear him undoing his belt buckle. "Pull your tits out of our bra and attach a clip to each nipple."

I had seen this coming, but my heart still sank at the idea of causing myself the pain I knew I was about to endure. "Yes, Master," I said. "May I set the phone down while I do this?"

"Set the phone on the shelf, and put your mouth as close to it as possible. I want to hear your reaction as you attach the clips." I could tell that his breath was quickening, and I imagined him wrapping his hand around his bulging cock, beginning to stroke it as he listened to me. The image made me both hornier and braver, and I quickly set the phone on a shelf just below shoulder level, unbuttoned my shirt, and pulled my right breast out of my bra cup. As instructed, I bent slightly, lowering my head so that my mouth was only inches from the phone, my shallow, nervous breaths echoing in my ears, fogging up my phone screen. My hands shook as I pinched my nipple in preparation, and I couldn't suppress a yelp as I closed the first clip painfully onto my nipple. I clamped my hand over my mouth to muffle the sound, but I could hear his quiet "fuck yes" on the other end of the line, the quickening sounds of his hand on his cock. The pain was more intense than the nipple clamps had been, and I had to take a few shaky deep breaths to prepare to inflict the same trauma on my other breast. Again, I couldn't fully suppress a whimper as the clip closed, and I steadied myself on the photocopier for a moment before putting the phone back to my ear.

"I've done as you asked, Master," I whispered.

"Good girl," James said hoarsely, and I realized with intense satisfaction that my second whimper has put him over the edge. "Now, I know you don't have much time before people come looking for you. So I'll be quick. Do you know what edging is?"

"Yes, Sir. It means getting close to cumming, but stopping just in time." I knew this because I had been educating myself on BDSM all week, consuming videos and blog posts every spare moment of my days since meeting James.

"That's right. Now I want you to try it. I don't think it will take you long, if you're as horny as you say you are. Tell me when you start, and when you have to stop. And don't you dare cum."

"Yes, Sir. I'm starting now," I said, running a finger along my wet labia to my swollen clit. As James has predicted, even though I was getting increasingly worried about getting caught, I was on the edge in mere minutes. I could feel my orgasm suddenly building in my stomach, its warmth rushing through my entire body, and I reluctantly but abruptly removed my hands, panting as the feeling subsided. "I stopped, Sir," I said, though I'm sure he could tell by my breathing. "I didn't cum."

"Good girl," James said, his voice crisp and commanding again. "We'll stop for now, before your office mates get suspicious. You can remove the clips. You might want to cover your mouth when you do."

The intensity of the pain as the blood rushed back into my abused nipples was greater than anything I'd experienced with James before, and I danced around the small closet foolishly, hand clamped over my mouth, tears pricking my eyes, until finally the feeling subsided.

James waited until he heard my breathing return to something like normal, then said matter-of-factly: "Put your tits back in your shirt. Fix your clothes. Lick your fingers clean. And you'll have to find a way to hide those panties on your way back to your desk - I expect to find a nice bare pussy under your skirt tonight."

"Yes, Master," I said, but he had already hung up. I hastily fixed my clothes and my hair, licked my fingers as instructed, the taste of my salty juices making me feel owned in a way I hadn't before, almost pushing me over the edge. I balled my panties into my hand and walked swiftly back to my desk, wondering if the smell of sex that hung around me was as powerful as I felt it was. No one looked at me when I reentered the office, but I felt everyone's eyes on me nonetheless—my cheeks flushed with humiliation, but my pussy dripped with arousal.

So here I sit, thinking about the panties waded up in my purse, and the slick wetness creeping down my thighs. I'm shifting in my seat, crossing and uncrossing my legs but finding both positions uncomfortably foreign. Even all these hours later, my nipples are hard beneath my bra, aching from both the binder clips and from my need to feel his mouth on them. And just when I start thinking that this date won't be like the first, just as I start in on a third glass of wine to calm my nerves, he pulls the rug out from under me.

"Now, pet, are you ready to see what tonight has in store for you?"

My breath catches, and I stare at him over my wine glass. He is watching me with that intense hunger that makes me weak, and I nod eagerly. "Yes, Sir."

"Come with me," he says, holding out his hand. I take it.

James leads me to his bedroom. It is the bedroom of a successful single man: all dark greys and browns, big windows hidden behind dark drapes, soft lighting from sporadic lamps. On the large bed in the center of the room, there is a black leather trunk. I regard it with interest, and James smiles at my curiosity.

"Last week with the birth of your submission. Now it's time to do a bit more exploring," James tells me as we move towards the mysterious box. "I have quite a large collection of items that can help us do that." As he speaks, he unlatches the trunk and eases the top open. "I suspect that after last week, you were curious about what might come next. Maybe you were thinking about your desire in a new way. Maybe you had particular fantasies. I want to talk to you about them—" my eyes fly to him in a panic - tell him my fantasies? - "—but we're not there yet," he says with a smile, and I relax slightly. Why can I beg him to lick my pussy, or hump his shoe, or edge for him in a supply closet, but I can't tell him what I've been dreaming about for the past week? It surprises me, but James seems unperturbed. "Tonight, I just want you to choose five objects out of this chest. Things that you'd like to experience. Things that you've thought about this week. We might not get to them all tonight, but we will get to some. Pick any five items you like, and lay them on the bed. I'm going to leave you for a few minutes to make your choice. Take your time. Do you understand?"

I nod. "Yes Sir."

"Good." He stands, kisses my head with real tenderness, and leaves the room, closing the door behind him. I'm left alone with the box.

I begin my exploration tentatively, taking out one object at a time and setting it on the bed beside me. Three dildos. Handcuffs. A butt plug. I turn the latter over in my hands, wondering whether I could take it into me, but the thought makes me queasy and I hastily set it aside and continue sifting through the contents of the trunk. Candles. Soft, red cotton ropes. I pause at the ropes, recalling images I had seen online of women with arms bound behind their backs, or bent over the back of a chair, unable to move no matter how much they struggled. My pulse quickens, and I set the rope apart from the other items, the first of my selections.

Nipple clamps. A ball gag. I want to be able to use my safe word, and my nipples still ache from the binder clip treatment earlier. A riding crop. The cool leather warms as I run my hands over it, and I imagine it leaving small red splotches on my pale skin. I quickly set it aside with the rope.

When James returns, I've added the remaining three items to the pile: a wooden hairbrush; a leash and collar; a small, silver vibe. James smirks at my items. "I see that last week's spanking made a real impression," he says, picking up the hairbrush, and I blush scarlet, looking at the floor. "That's good. I promised you a punishment earlier, and you've selected some perfect tools for me." His long fingers run over the rope, then the collar. "I'm delighted by your choices, pet. You've done well." He leans in abruptly, kissing me so passionately that I cry out before melting into his arms, spreading my legs to allow his groping hand under my skirt. He runs a finger down my sopping slit, but to my disappointment, he retreats as quickly as he began. "No panties. Good girl. And not lacking for arousal." He holds his wet finger out to me, and I realize he expects me to lick it clean. I comply, taking my juices into my mouth as our eyes lock. "I think we're ready to get started," he says. "Take off your clothes."

I hastily unbutton my blouse, wriggle out of my skirt, unhook my bra. He waits until my clothes pool on the floor beneath me, then leads me to the bed. "Position one, on your knees on the bed," he says, moving the trunk and beginning to unwind the rope with his back to me. I hesitate. What was position one again? I get onto my knees in the middle of the bed, spreading them as far apart as I can, but I can't remember what to do with my hands. Right before he turns back to me, I interlace my fingers behind my head, but I can tell by his expression I've guessed wrong.

"You can't even remember two positions from one week to the next, slut?" he barks, painfully grabbing a clump of my hair.

"I'm sorry Sir!" I whimper, ashamed. He lets go of my hair and steps away from me, and I feel his absence more acutely than I felt the pain he inflicted. There is a long pause. "Let's see if you've remembered anything at all. Position two."

I almost trip over myself as I rearrange my body on the bed. This one comes a bit easier - I remember it is like child's pose in yoga, with my cheek on the bed and my arms stretched out ahead of me, knees spread wide and ass in the air. I push my legs farther apart than is comfortable, arch my back so that my pussy is on full display. I am desperate to please him.

I stay like this for what feels like forever in the silence, until his soft touch on my back makes me jump. "That's right. You've remembered this one well."

"Thank you, Master," I say, my voice muffled by the duvet.

"In position one, you grasp your elbows, not your head, and throw back your shoulders to show off those tits for me." He is tracing his fingers gently along my back, and I am shivering at his touch, my body alive with desire for him. "A good sub can remember her positions from one meeting to the next. I'm disappointed that you're not taking this as seriously as I thought." Tears unexpectedly prick my eyes.

"I'm sorry, Sir," I say sincerely.

"You'll have to show me that you are truly sorry. That you have learned your lesson." I flinch as I feel the cool wood of the hairbrush I had chosen against my ass cheek. I steel myself for impact, but it doesn't come. Instead, James puts his face close to my ear and whispers, "You chose this brush so that I could spank you with it, but I don't even think you have earned painful contact from me yet. So you're going to spank yourself with this. You're going to spank your ass until it is red and on fire, until I think you've learned that I expect you to remember what I've taught you here. You're going to spank that ass to show me that you're sorry, to show me that you're serious. Do you understand me, slut?"

"Yes, Sir," I whimper, but my stomach feels like it has dropped out of my body, and my hand shakes as I pick up the brush, feeling its weight and regretting choosing it as one of my selections. Am I really ready to be spanked with an object like this? James has stepped away, and I feel so self-conscious now that he has removed his hand from my back, watching me alone on the bed.

As I begin to raise the hairbrush, James interrupts me. "As much as I would like to see you spanked in this position, I care more about your ability to spank yourself soundly, and that will be more difficult like this. You can get up on your knees and balance yourself against the headboard.

"Thank you, Sir," I say, repositioning myself. He's right - I can position the hairbrush much easier like this, and as a bonus, I am not so on display. Still, the discomfort of being watched so intently while I hurt myself on command remains. I rub the back on the brush over my right ass cheek in preparation.

"Count aloud," James says. "Ten on each ass cheek to start."

"Yes, Master." I raise the brush, hesitate just slightly, and then bring it down hard on my ass cheek. "ONE." The sound is louder, and the sting more immediate and intense than James's spanking had been last week. When I raise the brush over my left cheek, the memory of the first blow makes my second involuntarily lighter. "Two."

"I don't think so," James scoffs.

I suck in a deep breath and redo the second stroke, so hard I gasp out, "TWO."

"That's better," James says from the corner of the room.

I grip the headboard with my sweaty hand, trying to summon my resolve. This will be easier if I do it quickly, I think. I raise the brush over my right cheek again. "THREE. FOUR. FIVE. SIX. SEVEN. EIGHT. NINE. TEN!" Panting, I pause for a moment, feeling a creeping sting all over my ass.

"Did I say you could stop?" James asks.

"ELEVEN. TWELEVE. THIRTEEN. FOURTEEN." My voice is faltering; each number comes out as a whimper. "FIFTEEN. SIXTEEN. SEVENTEEN. EIGHTEEN. NINETEEN. TWENTY!" I drop the brush and reach back to rub my burning ass, but James barks, "No," so I place both hands on the headboard to steady myself.

James is silent as I catch my breath, but as soon as I begin to breath normally again, he says, "Again. Thirty more."

I steal a look at him, but his face is hard in the shadows. I pick up the brush and begin again, pushing through the burning pain in my ass, the ache in my arm as I swing the hairbrush again and again. By thirty, my ass is on fire. I picture red splotches covering my white skin, purple bruises just below the surface. At the end, I grip the headboard again with both hands, awaiting instructions.

"You're doing well," says James. "I see how penitent you are. But submission is not simply about punishing wrongdoing. It is about belonging to your Master, and allowing him to push you beyond what you think you are capable of. And while I see that you are sorry, I want to see you suffer a little more. And because I want it, and for no other reason, you will do it. Fifty more." My head snaps up and I stare in disbelief at him. I can see his eyes glinting sadistically. He walks slowly towards me until our faces our inches apart. "Fifty more, for your Master."

With him this close to me, I can almost feel the erotic charge in the air. Our eyes lock, and I feel a rush of almost animalistic desire, every nerve in my body straining to be consumed by him, while his eyes tell me he is just as intent on devouring me. Without breaking eye contact, I raise the brush and bring it down hard on my sensitive ass. "One," I breathe, my eyes still boring into his. By the time I get to ten, sweat is glistening on my skin and James is unbuckling his belt, unzipping his pants, pulling his shirt over his head. Twenty - I am yelping after each slap before I can force out the number. James is kneeling on the bed beside me, so close I can feel the heat radiating from his body. Thirty - my head is swimming, and the pain is no longer localizable, but covering my entire backside like an angry fire. I see James stroking his cock out of the corner of my eye, but our eyes remain locked on each other. Forty - I am on the edge of tears, and James takes my face in his hands, turning me so that my free hand is on his bare shoulder, so I look at him dead on. "Harder," he whispers, and I obey: forty-one, forty-two, forty-three. "Harder," he commands, and somehow I can, even as my body screams no: forty-four, forty-five, forty-six, forty-seven. "Good girl. Harder," he says, and I worry that I might cum right there, at his words, as I scream out my last three numbers. He can barely wait for fifty - the moment I've said it, he pushes me onto the bed, and his naked body is on top of me, his hands squeezing my breasts, his mouth hungrily pressed to mine. The pain of my abused ass rubbing against the bed is immediately overshadowed by the euphoria of James's shaft sliding into my needy, aching pussy. He slams into me again and again; I am on the edge in minutes.

"May I cum Sir?" I somehow remember to ask, though I'm not sure I can resist if he says no.

"Cum for me you perfect little slut," James growls, and I explode without hesitation, wave upon wave of my orgasm crashing over me, my fingernails scratching his back and my legs wrapping around his waist, trying to pull him even farther inside of me. My convulsions around his cock push him over the edge, and we lie spent in each other's arms as the tremors slowly subside.

When we've finally recovered, James pushes the hair out of my eyes and laughs. "You are...stupendous," he says softly.