I called J and asked her to drinks at a favorite bar of mine, a good local place modeled after a speakeasy with a great bourbon selection. The bar is down a flight of stairs and marked only by a red light, and during the week it’s very quiet so I knew we wouldn’t be bothered. I picked her up and told her that if we were going to continue the way we had that we needed to talk about limits and boundaries, and also that this was not going to start a romantic relationship between us, at least not yet. She agreed that she wasn’t looking for something romantic, and while she was interested in kink she had never had someone take it this seriously before, and that left her very intrigued. I remarked something about that being amateur, and how that would make me uncomfortable, but arriving at the bar we sat down, ordered drinks and began to talk. Our past conversations had led me to assume she was into a lot of things, and she didn’t disappoint. She loved being told what to do and how to dress, liked to be on her knees and serve, and she also talked a lot about forced orgasms but had never experienced one. As far as sex, she went on at length about how much she liked anal and also how she didn’t get enough opportunities to introduce toys into the bedroom. She was curious about being told to service other people if they were clean and I trusted them, and had a particular affinity for threesomes and exhibitionism. She said that her only experience with spankings were the kind she got when she was being fucked from behind, and she was very interested in corporal punishment, but asked that I work her into that slowly. J showed me her Tumblr while we were there, and her likes were filled with shapely girls whose bottoms and legs had be covered in aesthetically pleasing welts and bruises. I was happy to oblige in all the things I could, and I asked her if she wanted to start with the punishment she spoke of after the night we left her place for the first time. Her enthusiastic yes gave me the green light to implement an idea that I had often mused about after seeing a version of it in a porn once, but with my own little twist.
Arriving back at her place, I told her to strip down and wait for me on her knees. I went back out to my car to retrieve a folding chair I had previously cut a small hole into, some rope, two different canes, my hitachi, and two pairs of leather restraints. Taking my gear back in I found her waiting by the door as instructed, and I instantly had myself wanting to scrap the whole thing and just take her right there. Recovering, I set up the chair next to the counter we had first made out on and laid out the gear while she watched, wide-eyed. Returning to inspect my newfound plaything, the only thing left on her was a hair tie that I used to tie her hair back in while she waited obediently (almost like she’d done this before haha). I found she was very neatly shaven except for a small patch above her clitoris, not my particular preference but I could remedy that later. I bent down to kiss her, and tested her cunt ever so gently with the tip of my middle finger. She inhaled and cooed softly, and as I withdrew my fingertip out trailed a silver stream of wetness attached to it. I drew my cum-laced finger to her mouth and beckoned her open, and she sucked it clean with a smile. “Good girl.” I said, giving her a kiss on the cheek. “Now get up and come with me.”
I led her over to a bookshelf she had in the living room that I spied on my previous visits, and found a multitude of genres on its shelves. There were art books and poetry, a few textbooks, novels, some manga, and in the corner of the bottom shelf a small book that just said “classics”. I could’ve picked any for this project, but I wanted this to hurt and be both fun and frustrating. I took that classics compendium and thumbed through it until “Socrates” stuck out to me and I handed it to her. “Keep my place and bring that over here.” I commanded
“Ok!” She exclaimed
SMACK
I struck her lightly on the cheek and took her chin so that her eyes met mine.
“You sat kneeling like a perfect angel while I prepared and then touched you. You and I both know you’ve got more than an idea of how this goes, and you know that you don’t answer me like that.”
A subtle grin took hold of her face and she responded with “I’m sorry Sir, I won’t forget again.”
I laughed softly and then quipped “brat” with a smirk to which she smiled larger and giggled.
I took her hand and led her to the folding chair, and made her kneel so she could watch and get the idea of what she’d be in for. I slipped a condom over the head of the hitachi wand, and using the rope I tied a noose around the wand’s neck and secured it underneath the chair so that just the head stuck out above the seat. I plugged it in, and then restrained J’s small wrists and ankles with the leather cuffs. I had her sit in the chair backwards so that her breasts were against the back of the chair and secured her wrists to a hole there at the top. I made her arch her back so that her cunt was lined up with the hitachi, and the resistance from the rope gave enough so that it pressed back, parting her labia. Finally I fastened her ankles to the eyelets on the chair legs to hold her into position. The view of her exposed ass and puckered little asshole was exquisite. The head of the wand was already wet from her anticipating what was about to happen, and I was thrilled to see how much she was enjoying this before I let her in on the catch.
“I’m going to have you read for me, little brat.” I said calmly close to J’s ear, placing the book open in her restrained hands. “Every time you stutter or mispronounce a word I’m going to strike you with my cane, do you understand?”
“Yes sir.” She said, nodding and still smiling.
“Also J, you are not allowed to cum here in this chair during this task. When we entered into this arrangement you signed your orgasms over to me, is that clear? Only I decide when you get to cum now.”
“Sir, what happens if I cum?” She said, half bratty but also quietly concerned.
“I understand you’ve never done this before J so I’m going to go easy and work you up to controlling it more, and if you disobey me and lose control I’ll even let you pick what happens to you, but just this once, ok?”
“Do I have to choose now?” She asked me.
“No, because I don’t want you planning for it. I want you to genuinely try to control yourself. You told me to punish you after all.”
“Yes sir, I’ll try best for you!”
With a last “good girl” I started the wand on low and J let out a yelp, clearly not expecting the force of it. She had confided in me that she had used a hitachi before, but perhaps it had been a long while. The wand reverberated against her pink little cunt and J stared to moan and writhe in her predicament. “Read slut!” I barked at her and slapped her bottom with my palm, not overly hard but enough to get my point across. A pink hand print began to form on her left cheek as she slowly uttered the first words from the text with a surprising eloquence. I picked up my medium cane and watched her pussy twitch and her ass buck as she tried to maintain composure while finding a more comfortable position to lessen the vibration torturing her. It took her about 15 seconds to figure out that there wasn’t one and that she was going to have to learn to control herself while I watched in sadistic pleasure. Another 30 seconds saw her moans grow louder and she strayed from her lines.
SWISHHH
My strike made contact with her upper left ass cheek and J cried out but recovered quickly enough not to warrant another. That familiar red welt I had she had showed me on her phone just an hour ago started to form, and I wondered if she’d be pleased later when she saw how they decorated her supple little bottom.
J’s stuttering over another minute awarded her red “X’s” across both sides, and her moans told me she was struggling to maintain herself. I struck her a fifth time and turned the wand off.
“I’ll give you a minute break, open your mouth.”
The familiar slutty grin crossed her face as I unzipped and placed my throbbing cock onto the pad of her outstretched tongue.
“Suck brat!” I commanded, and J’s restrained hands began to work along with the expert tongue that I had missed since our first encounter. I began to fuck her face lightly before pulling out and returning the wand to its low settling. J was very excited, and moaned louder than the first time, clearly being more and more aroused by how she was being used. Again she started to read, but this time in a quiet, shaky voice.
I struck her again and said “louder!”
She picked up her volume and pace, making more and more mistakes earning her another 3 or so lashes.
As she built again I shut the wand off for another break, but this time she complained.
“Please Sir, I want it!”
“And you will, slut. I’ll see to it” I retorted, stuffing myself back into her mouth rand obbing her of a reply.
The streams of saliva started to come out as I fucked her mouth more roughly, only now realizing how worked up I was. I had focused my attention on making sure the scene went as planned, and while I was enjoying myself I had forgotten that I get to play too. After feeling myself begin to build I withdrew and gathered her strings of spit in my hand and rubbed them onto her face.
“What a mess you’ve made, slut. Disgusting.”
I turned the wand on again and struck her once for good measure, and from the half pained-half orgasmic squeal she made I knew she wouldn’t last long now.
“Sir I’m getting close, please let me cum!” She moaned out in a shaky voice.
“No, read. You know I’m not going to let you.”
J only got half a sentence in before asking again, more desperately this time. I denied her again, and swatted her for stopping to ask again.
“Ask me again before you finish that paragraph and I’ll give you ten!” I growled in her ear, but the fear that I meant to instill had the complete opposite effect.
“I’m gonna cum. I’m gonna cum! Sir please let me cum I can’t hold it!” She cried to me.
Any reply or consent I could’ve given wouldn’t have mattered as J came hard with sharp, loud squeals. Her legs shook and her ankles buckled, held in place only by the restraints around them as she continued to moan through her release.
“Didn’t I warn you, slut? Did I tell you that you weren’t allowed to cum during your task?” I barked at her while she was struggling to get off the vibrator. Her clit must have been extraordinarily sensitive after that hard of an orgasm.
“Sir I’m sorry, I’m so sorry!!” J got out in a panic.
I didn’t care to hear any of it. This was a punishment (albeit a playful one) and she broke the rules.
I took hold of the wand underneath her and pressed into her cunt and she screamed loudly and tried to wiggle herself away. The wand was wet all the way down the handle from her arousal and I had a bit of trouble maintaining the force I needed to continue to torment her.
“PLEASE TAKE IT OFF SIR PLEASE!” J begged me, writhing erratically as I forced it harder against her mound.
“No!” I spat back. “You’re going to tell me exactly how I’m going to punish you for breaking my rules.”
I gave her a few moments to squeal and mull over and her legs begin to shake again.
“Well!? How am I going to punish you slut?”
Her response made me pause and stare off in amazement.
Between her moans she caught her breath and gasped out “Whip me, beat me, FuCK ME HowEver you want But IF YOU DONT STOP…OHHH GOD….I’m gONna squIRt! I’M GONNA SQUIRT!” J moaned out in broken words.
My reaction was totally automatic and immediate. Holding the wand up against her I flipped the switch on to high and held it their against her.
The response from her was stunning and the first time I’d witnessed anything like it.
“OOHHHHHHH MY GGOD!” J wretched out as she released her cum onto the chair in a waterfall that ran from the seat and down the hole onto my hand. It was a warm and an incredibly sexy sensation as her cum ran over me and onto the floor with an audible splatter, as if someone had tipped a glass over onto the tile. Her asshole was gaping open and then closing again as her body involuntarily forced the liquid from her, and her swollen cunt was contracting along with it.
J was visibly spent and still moaning hard when I shut the vibrator off and unshackled her and helped her up from the soaked chair, bending her against the granite countertop.
“That was…incredible J.” I spoke softly to her with genuine admiration. “I’ve never seen anything like that, that was so sexy!”
“Thank you Sir, I don’t get to cum like that very often” she smiled back at me. “I’m glad you like the mess I’ve made.”
A split second thought entered my head about cleaning all this up later, but quickly disappeared when J said “will you please fuck me now? You’ve only had the pleasure of my mouth Sir, I have two more holes for you to use.”
My mind suddenly turned to my own growing need to cum, and I quickly tore my clothes off. I was rock hard and pulsing, J was admiring it while peering back behind her. She was running her hand over her soaked slit and down her legs where her cum had left wet, silky streaks on her thighs. Her eyes were telling me how much she needed it inside her, she had played such a long game to get here and it was finally about to pay off. The anticipation must have been killing her more than it was me as I greedily grabbed ahold of her perfect ass and teased her by moving my cock over the top of her slit.
“Please fu..” J didn’t even get to finish as I entered her, the foreplay had relaxed her and I felt myself go farther in than I had wanted, and as I retreated she tightened up, almost trapping me in her silky, wet little cunt. I pushed forward again as she moaned for me, and this time I went almost to her cervix. I don’t typically go as deep in early stages but a primal urge had come over me, and I’ll I could think of was greedily burying myself in her. J began to move her hips up and down to tease me as fucked her deep, and then I felt her fingers on either side of my cock. She was spreading herself open for me, and the sensation was incredible, but just after she began to fuck me back. I knew I wasn’t going last much longer here like this, especially with J’s moans driving me crazy, so I pulled out.
“I want your ass brat.” I said as I stepped back to gaze on her, stroking myself.
J giggled and smiled at me with that intoxicating slutty smile. She knew I was close, she could probably feel me pulsing inside her. She put her hands on her ass and spread herself apart for me, welcoming me in.
“You could’ve just cum in my pussy, you know it’s safe i told you I was on the pill. Cum wherever you want, just please let me have it inside Sir.”
The thought hadn’t even occurred to me. I had always pulled out or worn a condom. It drove me wild thinking about cumming in her at all, much less in her ass.
I ran my hand over her pussy and lubricated myself, and placed my head at her entrance. Her ass was surprisingly welcoming as I pushed forward slowly, and I got about three inches in before she winced in her moans. I pulled back and then went again, and found my rhythm. She had her hand on her pussy as I fucked her, rubbing another out of herself. I got rougher and went harder as she started to shudder.
“Can I cum Sir?” J cooed out.
I barely got out a “yes” before she collapsed under it, her ass dipped sharply when her knees buckled a little and her ass tightened up. That was just the sensation I needed. As J moaned through her orgasm I buried myself all the way inside her, which made her buck and arch her back. Deep inside I emptied myself into her, struggling to stay standing and gripping her ass tightly from the power of it. That amazing warmth washed over me and I slowly began to pull out. The amount of cum inside her must have been amazing because as I finished pulling out my semen followed me and began to barely drip out. I collapsed over her back and stroked her skin, kissing her softly. She recovered too and took me by the hand upstairs to shower off. We made out the whole time and washed each other, and then I went down to pick up the kitchen and clean up.
I slept in her bed that night, the first of many. She even woke me up half way through the night to go again, which was another amazing first for me.
This began a long standing routine that would last just over a year. We started doing everything together, including going out looking for other partners to take home. Keep that in the back of your mind for my next entry, which I hope will be soon.
I hope you enjoyed my reminiscence! ~KN