Getting To Know You
By RandyKneeling.
That’s when the unlikely couple came in. Their physical appearance was notable in itself. She was tall and athletic, not unlike a blonde version of myself. Her heels elevated her several inches over his slender frame. But what resonated with me was their demeanor. She was commanding, and he was deferential. As they made their way to a table, I could only see her well; her larger frame eclipsed him.
Once they were seated, the man faced in my general direction. I recognized him as a fellow employee from a different office department. We had never spoken, and I didn’t know his name, but I walked past his desk at least twice daily on my way in and out of the building.
When the waitress came to take their drink orders, the woman spoke for both. That’s when I knew what they were. Regardless of how formally they identified themselves, there was no mistaking it—she was a Domme, and he was her sub. It takes one to know one, and while we had never met, I certainly knew her.
I was grateful for the large plant between us, which allowed me to lean to one side and steal glances at my choosing. My view of her was from slightly behind, allowing me to discern her demeanor while avoiding her peripheral view.
I could also see her shapely stockinged calf below the hem of her dress. Her legs were crossed, and she casually bounced the top one. The sunlight streaming through the window periodically flashed off something at her ankle. I surmised it was an anklet, but I was too far away to see a chain. I saw the thing catching the light—a small key.
So, her boy was locked. How lovely! I looked forward to the next time I saw him at work now that I knew the secret he had in his pants. Ten-to-one, it’s encased in some pretty little panties, I mused.
My lunch partner’s arrival forced me to reduce my prurient surveillance of the couple drastically. I focused on the remaining details of our contract while simultaneously talking up the rush hour traffic he was bound to hit on his way to the airport. It wasn’t a lie, but I did exaggerate a bit, wanting to send him on his way as soon as possible.
When my deal was settled, I volunteered to cover the tab but told him I wanted to stay and finish my drink. I bade him blue skies and settled in to catch up with my new friends. Up to this point, I had only been able to discern that they were engaged in a fairly emotional discussion.
Now, I saw things at their table had progressed, but in a different way. Their discussion was animated, and he was distraught. He stayed longer than necessary when he dropped a napkin and bent down to retrieve it. I leaned forward in time to see him kissing her foot. By the time he came back up, he was crying openly. I felt an instant pang in my heart for both of them. Him for his obvious anguish and her for the embarrassment of the public scene her boy was making. I wondered if he was one of those subs overly prone to emotional outbursts.
I knew I was mistaken when he handed her the anklet chain. She took the key off it, kept the chain, and handed it back to him. There could be only two reasons for that. Normally, it would be so he could release himself, but his misery precluded that explanation. The alternative was that she no longer wanted to hold his key, that she no longer wanted to be his Domme. This was a breakup—one not mutually agreed upon.
I flashed back to my first sub and the haphazard way we had both stumbled into our respective roles. How vulnerable he had been, how ineptly I had asserted my authority, not knowing any better, and how sadly it had ended. I wanted something better for them.
It had been over a year since I had enjoyed having a dedicated sub, something more difficult to find than might be imagined. Beta males who court the lifestyle can make for a fun diversion, but most lack the devotion I require. They need to center their life around the adoration of a woman. In most cases, better to put them on the cocks they need to suck and leave them to revel in their feelings of inferiority.
A long-term, Domme/sub relationship is far more special and rare. Now, I could snatch up a sub who knew what he wanted and was already trained. The opportunity was simply too promising to pass up. I settled my tab and hurried back to the office, intent on getting there before my quarry.
Stopping by his vacant cubicle, I quickly scanned his workspace while pretending to jot a note to him. His computer monitor held several Post-it notes, including one addressed to him. Just his first name — Don — but it was all the clue I needed. Returning to my desk, it was simple to pull up the organizational roster for his department. Sure enough, there was only one Don – Donald Armstrong. I sent an E-mail to his corporate account using a personal account that didn’t reveal my name. He would learn that soon enough if he proved worthy. I sent it after hours so he would have a night to let his new situation sink in before he saw it. The letter read,
* * *
Hello Don,
We haven’t met, but I know you’re struggling. You don’t know me, but I understand and am in a position to help. You’ve lost someone very important to you. I can fill the hole she left, provided we are compatible.
You still need to use your key, don’t you? I know it was tempting, but it didn’t feel right, did it? Unlocking is a special reward; you don’t feel you deserve a reward. If I need to correct that, please don’t hesitate to reply. I wish you all the best and hope you find another Domme who will give you what you need.
But if I’m right, could you RSVP to this invitation for a private interview at 6245 Riverside Drive this Saturday at 1 p.m., and bring your key?
Mistress Jacqueline
* * *
His reply was time-stamped at 9:36 AM the next day. Given that he probably went through several rewrites, I judged he had made his decision in less than an hour. It was perfect: not too hasty, but not prolonged agonizing either. I read it a second time, hoping for further insight.
* * *
Mistress Jacqueline,
How do you know? How could you know? I was convinced my mistress must have told you, but she swears not, and I believe her. So, I am left to reply without knowing. But you do know. And you are right — I haven’t used my key for exactly the reason you stated. It’s like you’re in my head. It’s scary, yet somehow comforting.
I feel compelled to trust you and the fates that brought me to your attention. Please don’t worry, I will arrive at the specified time, for I am nothing if not a person of my word.
* * *
Interesting, I thought. The more common form of that phrase would be “a man of my word.” A woman might naturally use the more generic formulation, but I couldn’t help thinking a more conscious process occurred in this case. Interesting, but perhaps not surprising.
Promptly at 1 p.m. that Saturday, my doorbell rang, and I watched through the ring camera as he fussed with his hair in the reflection of the sidelight glass. Out of nowhere, I was struck with an analogy in which I was the spider, and he was the fly. The only difference is that flies don’t volunteer to enter the web. I opened the door and saw a mix of recognition and confusion as he struggled to place me.
“Mistress Jacqueline?”
“Yes, Don; welcome to my home. Please come in and have a seat.”
We made ourselves comfortable in the living room. I got him to give me a brief background on his situation. I was relieved to learn the breakup was not related to any failure on his part. His Domme had moved out of state to pursue a career opportunity. He wasn’t financially dependent on her; he was simply emotionally bereft. So far, he was checking all the boxes. He wasted no time revealing what was on his mind.
“I can’t stop thinking about it… about how you knew. Please tell me.”
“I realized you would ask me, and I’ve considered the options. I will let you know if you want to, but first I want to share my thinking. I acknowledge the value of telling the truth, but where is the virtue in telling every child that Santa isn’t real? I don’t have all the answers, and I may only sometimes be the right person to provide the ones I have. Sometimes, imagination can provide welcome comfort. Let me ask you, curiosity aside, is it really important that you know?”
He was turning it over, and I was pleased to see genuine deliberation.
“I thought it was important, but I also see wisdom in your words. Perhaps, for now, it’s enough to know you will tell me if I ask again.”
“I promise. And I, too, am a person of my word.”
Was it my message that made him smile or my highlighting of his phrasing? Playing with an unfamiliar body is always fun, but my greatest pleasure is derived from exploring the largest sex organs.
“Tell me, Don, how long had your previous relationship been exclusively Domme/sub?”
“Uh, I guess around… six months?”
“And was this mistress your first?”
“Yes, Ma’am.”
He looked down as he spoke. Initially, I attributed it to a normal submissive posture, but I realized his gaze was predominantly directed at my feet.
“Donald, do you have a foot fetish?”
“No, Ma’am, I’m sorry. Was I making you uncomfortable?”
“Not at all. I simply thought you might be a little fixated on my feet. It’s not uncommon for subs to have a thing for feet.”
“It’s nothing sexual, but I always enjoyed serving at the feet of my mistress. It’s the symbolic nature of it, more than anything. A desire to be beneath you.”
“Would you be more comfortable sitting on the floor?”
“If I could be at your feet? Yes, I would like that, Ma’am.”
“Then, by all means, make yourself comfortable.”
He slid off the couch and sat cross-legged, facing me. I purposely did not offer to remove my shoes, wanting to observe his ability to control his urges. He seemed content with the subservient position, more at ease.
“How long have you been in chastity?”
“It started off and on, the first month; it’s only been permanent for the last two.”
“When was the last time you had an orgasm?”
“Two weeks, Ma’am. Of course, it was ruined.”
“When was your last full-on, pleasurable ejaculation?”
“I… I need to remember. Maybe a month?”
His mistress had done a fine job with the chastity training. To so quickly become accustomed to his orgasms being ruined – to the point where he didn’t even track the days since his last full one, was impressive.
“What ground rules did you have with your mistress?”
“Ground rules? We didn’t have any.”
“Nonsense, of course you did. For instance, you don’t want your employer to find out.”
“No, of course not. I see. Okay, I don’t want anyone in my life to find out. Not friends, and certainly not family.”
“Well, I agree that employer and family are out of bounds. I’ll have to meet your friends before I can agree to that part.”
He looked concerned and hesitant but did not object, and I pressed on.
“How far did your mistress push you?”
“Well, I couldn’t orgasm without permission, of course. She determined how I dressed, what I ate, who I could… ”
“No – no — no, not the boring stuff. Tell me some of the most challenging things she had you do.”
“Uh… well, one time… we were at the beach, and she took my bathing suit off when we were in the ocean, and she threw it into deep water and then held onto me while it drifted away. I had to make my way back to the car naked. It was very embarrassing.”
“I’ll bet. What else?”
“Another time, she had me lick her just after she peed. She hadn’t wiped herself.”
His shame was evident as he reflected on the incident.
“Has she forced you to eat cum?”
“Just mine. Every time.”
“What’s been up your ass?”
“N-nothing, Ma’am.”
“Which of the things you mentioned get you the most aroused?”
“I guess eating my cum, at least at first. But I’m used to that now. I kinda like it.”
His blush was touching. The next tidbit was offered confidentially, akin to a confession.
“I still get excited when I think about how she made me lick her dirty pussy.”
“Interesting choice of words, Don. Not precise, but revealing.”
Pissy pussy would have been more precise. The intel that the thought still aroused him was a gold mine for me. The fact that he used the word “dirty” was downright delicious.
“I’m satisfied that you are worthy of my time. You lack experience in only one critical area.”
I reached into an end table drawer and produced a small butt plug and some lube.
“Please insert this in your anus for me.”
I could see his surprise, followed by his internal struggle. Although it was delicious to witness, I didn’t want to see him fall short due to runaway emotions.
“Go ahead, right here. Drop your pants and underwear, and lube the plug and your hole. Do it NOW!”
Raising my voice was the biggest hurdle in the test, and he cleared it with plenty to spare – his pants were around his ankles in a flash. I was pleased to see he was indeed wearing panties — a lacy little number that perfectly showcased his chastity cage. He wiggled out of them to reveal a snug-fitting cage of stainless steel.
When he had the plug slick and had applied a dollop of lube to his butthole, he looked up at me, pulled a cheek, and lined up the tip.
“It will be easier if you squat.”
He followed my advice and lowered himself to the floor. Then, to his credit, he inserted the plug with only the slightest hesitation, completely understandable for a virgin. His face was priceless, eyes wide, darting, suggestive of the ping-ponging thoughts no doubt firing through his brain.
“You will wear that for a while, then we’ll play some. In the meantime, is there anything else you want to ask me? After today, aspects of my life separate from you will be off-limits for discussion. Do you understand?”
“Yes, Ma’am.”
“So, is there anything you would like to know? Perhaps to alleviate any anxiety you might be feeling?
“Ma’am… there is one thing I’d like to know, but I’m afraid it might be impertinent of me. It’s more than just asking for information.”
“Don’t worry, you have my permission; now out with it.”
“Could I… lick you, Ma’am?”
“Ha ha ha ha ha! Oh, my dear boy, you most certainly can!”
I pulled off my panties and handed them to him as I moved into a reclining section of the sofa. He pressed his face into my panties and inhaled deeply as I raised my legs and allowed my skirt to slide up my thighs. He dropped to the floor between my legs, and I placed my feet on his shoulders.
His approach was respectful, as I had hoped. In truth, I was fine with his talents. Every woman has her preferences and rhythms; I was confident he would learn mine. Enthusiasm was the only thing I required that could not be taught, and he had already shown that. Anything he needed more stamina would come with practice.
I was pleasantly surprised by his various techniques and the frequency with which he could flick his tongue. He was becoming quite enthusiastic, but I decided it might be better in the long run if I left him with the feeling that he needed to try harder next time.
“That was perfect, darling, but we can save the big finish for another day. Your butthole should be stretched enough to proceed.”
“Please Mistress, may I be allowed to continue, just this once?”
“Why?”
“Because I need to make you orgasm. I need to know if I’ll be able to give you the ultimate pleasure I can provide. And I want to…”
“What? What else do you want?”
“I want to see you orgasm. Not… not because it will arouse me, although it will. I need to know that I can be happy in this relationship, which is only possible if I can make you happy. I need to experience your happiness. To know I can bring it about and to be sure it will be… enough for me.”
“I think it’s lovely that you need to see me come! And I appreciate your self-awareness and your ability to express yourself so eloquently. It will be easier for me to come if I empty my bladder first. Step out of those pants, lose the shirt, and follow me.”
I proceeded to the bathroom, my applicant in tow. I gathered my dress to my waist and sat on the toilet, motioning to the floor before me.
“Kneel and watch.”
I used both hands to spread my labia and placed each index finger on either side of my pee hole. I watched him as he watched me let go of my stream. It shot out tight and strong, splashing at the waterline. With subtle movements of my fingers, I varied the sound as my stream shot into deeper water, then onto bare porcelain. I adored the fascination in his eyes, which were locked onto my urethra.
“You like to watch me pee, don’t you, Donny?”
His eyes shot up to mine, wordlessly revealing that’s what she called me! He answered my question with a nod and tore his eyes away to resume his fascination with my stream. I took his hand, extended a finger, and lowered it into my stream. My golden nectar covered the digit, bathing it until I ran dry. Then I lifted his wet finger and watched a drop form at the tip.
“Do you want a taste?”
“Yes, Mistress, please.”
“Ask nicely.”
“Please, Mistress, please let me taste your pee! I want to suck your pee off my finger! Please!”
“Very well… good boy.”
Hearing those two magic words produced a delightful shiver. He sucked his finger long after it was clean, gazing into my eyes the whole time.
“Now you will service me the same way you will every time I pee in your presence. Lick my pussy clean, boy.”
I let him move in on his own and savor my taste at his own pace, only grabbing his head once I felt clean. Then I ground into him, forgetting that I had turned his previous boundary into his new normal. And he hadn’t even balked!
His face filled the space between my thighs, and my legs hugged him, sealing in the aroma rising from the toilet bowl. A bowl full of my rank piss, which I forced him to inhale.
“Breathe deep while you lick me, Donny. You’re going to get very familiar with that smell. You’re going to learn to love it because it came from me. And because it makes me happy when you do it.”
His muffled “Yes, Mistress” echoed in the bowl. I couldn’t help but chuckle as he obediently lapped away. I had envisioned retiring to the bedroom to let him get me off, but when I saw how much he was enjoying this, I saw no reason to deny him more of it. Admittedly, I also recognized the powerful association I was burning into his subby brain. He would always remember the first time he made me come, and now an inseparable part of that memory would be the smell of my piss. I resisted the urge to push his head deeper into the bowl. There was just so much to look forward to!
I could feel my orgasm building, spurred on by my nasty thoughts. He began flicking my clit with the tip of his tongue, and he did it so fast it almost felt like a low-frequency vibrator on my hardened nub. I ground into him and surrendered to the waves as they began to wash over me. It wasn’t a monumental orgasm, but it was entirely satisfying. Even as it peaked, I had the presence of mind to release his head, allowing him the visual he had worked so hard to achieve.
When it was over, and I opened my eyes, he gazed upon my face like the devoted supplicant he was. I smiled down at him, and he mirrored my sentiment, his emotions already tethered to my own.
“Mistress Jacqueline, I have only one remaining request. Would you please do me the honor of holding my key?”
It was a beautiful moment of surrender, and I knew I would eventually accept his offer. I also knew it needed to be on my terms. I couldn’t have him thinking he had somehow convinced me that he was deciding things here. Becoming his keyholder needed to be my decision, made at a time of my choosing, a privilege I bestowed upon him.
“I’m pleased with your offer but still need to finish evaluating your worthiness. Go kneel before the bathtub and place your arms inside it.”
I stood up, smoothed my skirt, and followed him to the tub. When he was in the instructed position, I turned around and straddled his back, facing his butt. I brought enough weight down on his back to pin him onto the ledge of the tub without crushing his ribs. Then I grabbed the plug and pulled it halfway out, stopping when the widest part was stretching the tight sphincter of his asshole. I glanced over my shoulder to watch his face as I slowly sawed it back and forth, using that widest half-inch to open him up. I saw his expression transform from worry to relaxation, then to pleasure, as I slowly fucked him with the plug.
“Talk to me, Donny. Tell me how this feels.”
“Oh, Mistress! Wonderful! Amazing! I had no idea!”
“You mean you had no idea that your asshole could be the source of such pleasure? No idea it could feel so good to get fucked in the ass?”
“Yes, Mistress! Yes!”
“This is just the beginning. You’re going to take my strap-on, Donny. You’re going to take every inch of it while it stretches out that tight little boy-hole of yours. And when I give it to you often enough — when you start to feel comfortable with it – you’ll graduate to a bigger one. This is going to become sex for you, Donny. It won’t be the only way I let you come, but it will become your favorite. Do you know why?”
“B – b – because it feels so good?”
“Partly, yes. But why else, Donny?”
I could see him thinking, worrying he might say the wrong thing. Then it came to him.
“Because it will make you happy!”
“There you go, Donny-boy! Yes, because it will make me happy. And when it’s my strap-on, it will also make me feel good. Which is why you’re going to experience that today. I’m going to fuck you in the ass, Donny. I’m going to teach you to love my strap-on. Before long, you will beg me to fuck your ass.”
I showed him where I kept the enema bulb that would now be his and, given his inexperience, verbally instructed him on the thorough cleaning I expected him to administer. Leaving him to his task, I retired to the bedroom to throw down a protective covering on the bed and position various items for our play.
Stepping into my strap-on harness, I affixed the dildo I thought of as my cherry popper. Only slightly thicker than the plug he’d already taken, his end was 6″ and smooth. Barely more than the 5″ on my side, but a good start for my little butthole virgin.
I had fairly worked up with anticipation when he appeared, looking somewhat frightened when he saw the phallus I now sported.
“Time to unlock you, Donny. You will be required not to touch your penis unless I expressly allow it. If that will be a problem for you, I can handcuff you.”
“No, Mistress, it won’t be a problem. A challenge, but one I am happy to meet for you.”
I stepped to him and cooed in his ear,
“Donny, darling, you should be careful saying things like that. I could be in danger of losing a piece of my heart to you. You honestly want to deny yourself for me, don’t you?”
“Yes, Mistress, I do. It’s another thing I can offer you if it pleases you.”
“It pleases me very much, my dear. Now unlock yourself, and let’s have a look at your little penis.”
Free of its prison, his shriveled dick appeared as a stack of plump wrinkles barely an inch long. We watched it grow in silence for a few moments, each of us enjoying the blossoming. When all the wrinkles stretched out, it was 3″ of thin dick, and I could see there wasn’t much more.
“Very nice. Just the kind of diminutive little dick that makes for a good submissive boy. It’s like I always say: those who can, fuck. Those who can’t, serve.”
“Yes, Ma’am.”
Now, get on all fours on the bed.”
I guided him back to the foot of the bed, where he was kneeling at the edge, straddling the corner.
“This is my favorite position to fuck my boys in, remember it. It will be the position I want you to take today as soon as I let you off your back.”
With that, I grabbed his shoulders and guided him up on his knees, turned him to face me, and roughly pushed him over. He fell predictably near the center of the bed, and I hopped on him in a flash. Moving quickly, I placed his feet on my shoulders, grabbed a pillow, and shoved it under his butt.
“I know the flushing you gave yourself also resulted in an empty bladder, so I want you not to worry about relaxing, even if you feel the urge to pee. If you do pee, it’s no big deal. It won’t be much, and you’re on a pad. With luck, it may be semen, and then you can show me how you eat it.”
I might have gotten a little carried away with that last bit. Caught up in playing with him, I had stroked his libido, and his dick instantly stiffened in response. It certainly didn’t take much, which was promising. He had 2 weeks of pent-up spunk; I just had to keep things under control until I could get to his prostate.
I lubed the dildo, then laid a dollop on his hole. I caressed it, rimmed it, then slipped a finger in and out a fraction at a time, pushing more lube ahead of me on each foray. My eyes were locked on his the whole time. It was the sole reason for this position. Seeing those first moments, each precious, never to come again. He started to bliss out and close his eyes.
“No, no, sweet boy; look into my eyes. You can focus on how good your hole feels, but remember who’s making it feel good. Show me that ecstasy, I want to see your gratitude. Look deep into the eyes of the woman making your hole the center of your universe. Understand what’s happening. You’re more vulnerable than you’ve ever been in your life. I could take your hole right now, but I’m not going to, not yet. I want you to give it to me. Open it up for me, let me in.”
My first finger was sliding free, and I worked a second in alongside it. He began to moan, and a drop of precum formed on the tip of his dick. I captured it on my fingertip and fed it to him.
“I can see you like this; go ahead – enjoy it. But understand, this is more than just me making you feel good. This is my finger fucking you. Your asshole doesn’t just feel good. I’m making it feel good by pushing my fingers into it. I’m loosening up your boy hole for my stiff rod. I’m about to make you my bitch. Are you ready to be my bitch, Donny?”
“Yes, Mistress! Yes! Please give it to me. Make me your bitch. Do it, please!”
I slipped my fingers out and quickly replaced them with the tip of my dildo, catching his gape before it closed. Then I let him feel the pressure, my hardness knocking at the door, wanting in. I could have easily pushed through the remaining resistance and forced my way in, but watching him crave every next inch was just too much fun.
“Take it in, boy. Take my girl’s cock. Open your boy pussy for me.”
I was halfway in when I heard his first whimper. I nearly cried at the beauty of that sound. So feminine, so submissive, so helpless! It further fueled my power over him. I pushed in firmly and held it there, watching him as he whimpered and quivered on my pole. I stroked his stomach, avoiding his now flaccid penis as it lay helpless over his swollen balls.
“Good boy, Donny! You took it all. Took it like a good little bitch. Now open your mouth.”
I gathered the saliva in my mouth and opened it over him, drooling into his mouth as I gazed into his eyes. He received my offering willingly, desperate to please me however he could. I began sawing slowly in and out, letting him feel the length of my shaft in his rectum.
“Now you’re gonna get fucked like a little bitch.”
He was moaning on each outstroke and whimpering each time I buried it deep in him.
“That’s it, bitch. Take it all, nice and deep. Give it up for your mistress.”
My pace increased until I was fucking him fast, pounding into him, his little package bouncing wildly with each thrust. When he looked overwhelmed, I slowed down and then pulled out.
“Time to assume the position, Donny. Let’s see if mistress can make you come.”
I helped lift his legs off my shoulders, and he rolled, then scooted back to the foot of the bed and stuck his ass over the corner. I got off the bed and stood over him, adding more lube to my now-warm dildo. His pucker was winking open and closed, ready and eager to be fucked again.
I reached under the bed and retrieved the black ceramic dinner plate I kept for such occasions. I placed it on the bed between his legs and lined up for my assault.
“Very good, all fours is the position; but for just a moment, I want you face down, ass up. Grab your cheeks and spread ’em. Yes… that’s it. Open that hole for me so I can give it as you need it. Like a bitch.”
I grabbed his hips in my hands and pulled him onto my phallus. He let out a long, low moan that hardened my clit. Not only was my dildo insert pressing against the upper wall of my cunt, but the stiff front of the harness also mashed against my clit as I bottomed out in him. I fully expected to come before he did.
“Your turn to make yourself feel good, Donny. Rock back and forth on it. Fuck yourself with it, Donny.”
He raised himself onto all fours and began moving as I caressed his butt cheeks and dragged my nails lightly down his back.
“Good boy, take it deep. Be my little cock sleeve. Show me the way you like it. How you liked to get fucked in the ass.”
His breathing was strong but with a ragged edge like his vocal cords were shivering along with the rest of him.
“You have no idea how good your ass looks right now, Donny. Filled with my tool, stretched wide to accommodate its girth, your legs splayed open so wantonly. Donny, you’ve become a slut! You’re my little ass-slut!”
His moans became so loud I thought he might just come under his own steam, but he seemed to plateau. He looked desperate and confused at the same time.
“I… I, I can’t get there. It feels so good, but I need to touch myself. Please, Mistress, may I be allowed to touch my dick?”
“You think this has anything to do with your orgasm? That impertinent request just earned you a discipline spanking when we’re through here. Care to escalate things any further?”
“No, Mistress. Please forgive me, I forgot myself.”
He immediately stopped thrusting into me but held the length of my shaft inside.
“But I don’t see fear in your eyes, as expected. Is that shame I see? Are you ashamed to be spanked?”
“No, Mistress. I’ve never been spanked, so I have no special feelings about it. I’m ashamed because I allowed my needs to override your expressed desire. I failed you.”
“You continue to warm my heart, subby. Yes, it was a failure, but a minor one. At least you only begged rather than touched without asking. I shudder to think of the punishment that would bring about.
And it is appropriate that you suffer some negative emotion over your brash outburst. That the emotion is shame is perfect – shame is the essence of what is naturally purged by a good hard spanking. As much as you will suffer while it’s happening, I believe you will love what you experience in the aftermath.”
“In that case, Mistress, I look forward to it.”
“Ha ha ha, excellent! Now, let’s get back in the saddle. Show me again the way you like my phallus to violate your hole.”
Like a good-ass slut, he fell back into sub-space quickly. With all the talk of shame, I suppose his mind hadn’t ever wandered far. He began to long-stroke himself, pulling completely off my girl’s cock every time he rocked away from me. As he rocked back onto me, his hole stayed wide open and recaptured its former invader, once again welcomed and embraced warmly.
“You’re doing a wonderful job; you just need to learn more about your body. Would you like me to help you with that, subby?”
“Please, Mistress; any way you can help!”
He probably expected me to take him in hand; no doubt he’d explode like a fire hose. That’s not at all what I had in mind. I ordered him to stop, then centered the plate below his dangling member. I pushed into him at a downward angle, the tip of my dildo gently probing for his magic walnut. When his groan took on a deeper, more guttural tone, I knew I had found it.
“There it is. Feel that, Donny? Take note where I am now — I’m stroking your new best friend.”
I took a few passes up one side, then the other, gaging his reaction to get a better sense of its location. I ground my hips in place when I knew I was centered on it. The hard tip of the dildo directly massaged his p-spot, and clear fluid began to dribble from his dick. I kept grinding and watched as the dribble became milky, then a sustained stream of thicker cum flowed helplessly from his little penis, spending itself onto the black plate. I laughed as his breath escaped in a long whimper.
“You did it, baby boy! You came from Mistress’s cock! Such a good little boy, Donny!”
I reached out and stroked his head, praising and telling him how happy he had made me. Knowing nothing was more important to him, I slid the plate before his face.
“Show me how you eat your cum, little boy. Such a big puddle from a little dick that wasn’t even touched! Taste what mistress milked from you, sweet boy.”
He lapped away gratefully, openly relishing the experience. I held still inside him until the plate was clean, allowing him undistracted enjoyment of his treat. Then I resumed the long, slow stroking I knew his hole still craved. Each time I bottomed out, I did so with a firm press and grind; because that’s what my clit craved. When I wasn’t stroking him, I stayed deep and pounded into him forcefully. He was moaning constantly now, only the change in volume revealing his degree of desperation.
“Who owns this ass, boy?”
“You do, Mistress.”
“That’s right, and I’m fucking it. I’m fucking you good, subby, and you’re taking it like a bitch. Like my bitch! I love the look on your face as you take my cock. Right — up — your — ass. Such a pretty little ass slut!
You’re about to get two treats back-to-back, Donny. You’re going to get to see me come again — I’m gonna come all over the little dick that’s inside me. And that’s how I make your second treat. You get to taste my cummy pussy on that little dick.”
“Oh my God, Mistress! Please! Please, I would love that!”
I was on the edge and saw no reason not to just charge over it. I pounded him through the duration of my orgasm, and he stayed with me the whole way. When I pulled out of him, he fell on his stomach as I unstrapped the harness and stepped out. I walked to where his face hung at the edge of the bed and rubbed the tip of the little dick over his lips, avoiding his attempts to capture it in his mouth.
“This little guy is very close to your size, right? Not enough to impress a woman, but at least something to squeeze on while I got off. Here it is, fresh out of my pussy and covered in my cum. Something your little guy will never experience.”
I pushed the slimy little dick into his mouth and let him go at it. He sucked greedily on the rubber dick, blissing out over the taste of my cum. When his ravenous sucking became contented suckling, I reluctantly brought him back to earth.
“It’s time,” I said. I think you need to be atone for the impertinence you demonstrated earlier. You earned yourself a discipline spanking, which you will now receive. Let’s start by locking that little troublemaker back up. You can use that key and then hang onto it.
Here’s how this is going to go. I’m going to warm your bottom; then I’m going to proceed to spank you with a purpose. Any play-acting reactions from you will be ignored. If I believe you truly desire it to end, it will. But I want you to endure the pain because it will give me pleasure to see.
Just to let you know, if you enjoy the experience, your reactions may feed my enthusiasm. In which case, I may exceed your capacity to endure. That will be your responsibility to decide.”
I sat on the edge of the bed and indicated for him to lay across my lap, and he meekly complied. I stroked his buttocks, then rained down upon him a rapid-fire series of spanks on his bare ass. It jiggled most satisfyingly, slowly turning pink from my continual assault. When my hand began to sting, I reached under the bed for one of my slippers. While establishing a good grip, I stroked his heated buns and gave him time to register the moment.
“What you feel right now is the tender sensitivity and heat of a maintenance spanking. You will become accustomed to this feeling, even appreciating how it reinforces our bond. Good subs deserve such loving attention. Only bad subs get what happens next.”
I forcedly brought down the slipper, and a howl escaped his lips. The second blow to the other side, then another to each in turn.
“The next time you’re lucky enough to get used to my happiness – WHACK! – you damn well better remember that your happiness has nothing to do with it!” – WHACK – WHACK – WHACK!
“Y-Yes, Mistress,” he whimpered.
“If I ever – WHACK! – let you come – WHACK! – while I’m pleasuring myself – WHACK! – it will only be because it makes me happy to see it. – WHACK – WHACK – WHACK! It won’t be because you want it! – WHACK – WHACK – WHACK – WHACK – WHACK! UNDERSTAND?”
“Yes, Mistress! I’m sorry, Mistress! I promise it won’t ever happen again!”
The words were common, even trite; but they were delivered with such conviction that I almost believed him. More importantly, the unrestrained bawling and blubbering that accompanied them was as genuine as gratifying.
“It better not ever happen again. Discipline is not something I look forward to providing, but it’s part of my commitment to you. I will do whatever it takes to help you be my devoted submissive.”
“So will I, Mistress.”
“In that case, Donny, I accept your key.”
The End.
*This story has been edited by AI to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Even with the limited editing done here, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech. This story has been previously published on other free sites and is now public domain, which is why we can publish it here.