Joey’s Anal Punishment

I found this lusty little spanking and anal sex story in a file from a spanking story site that doesn’t exist any more. It has some prose in common with stories you can find at ASSTR and similar sites called Sarah’s Anal Punishment and Joey’s Detention, but it’s been heavily edited by parties unknown (for the better, I’d say) and differs substantially from the existing versions of both of those. Our heroine is a reform-school girl who attracts the warden’s lustful ire:

Joey’s Punishment

Joey was marched in to the punishment room kicking and cursing. Fortunately the three assistants were a match for the hardened reform-school girl, but it was very obvious to me that she would need to be strapped down for her discipline.

The three matrons hoisted her over the sturdy leather sofa, and while two of them held Joey in position, the third drew her arms down and strapped her wrists firmly to the base of the heavy sofa legs. A stout belt was pinned around her waist over the sofa, and a third strap secured around her knees.

“In the mood for the cane, Joey? No? Lets see how you feel about it after we remove that skirt you’re wearing!”

My hands trembled slightly as I found the small side clasp and drew the skirt down her trim legs. The elastic tightness of her white knickers strained over the plump fullness of Joey’s rear cheeks, broadened and fattened by her bent posture. She had struggled hard when being strapped down, and her elastic-trimmed panties had ridden up the cheeks of her bottom, laying bare the fat lower curve of her ass cheeks.

I took the tail of Joey’s white blouse and tucked it up under her waist strap. I hooked my thumbs in the waistband of her panties and slowly lowered the material, watching as her ass flesh compressed and then rolled out from under the descending material. I sucked in my breath and felt my heart start to pound in my chest as Joey’s ass was now completely bare to my view.

I pulled my desk chair up behind Joey and sat down right behind her, inspecting this exciting rear view. Joey’s legs trembled slightly as she felt my hand fondle the slight heaviness of her chubby rear orbs. I bounced them up and down lewdly in the palm of my hands, each bottom cheek occupying one of my warm palms, watching as the fat of her rear mounds jiggled with the movement of my hands, smiling at Joey’s soft protest of this indignity as she felt my hands on her bottom cheeks.

“I am going to use a bamboo cane across these pretty bottom cheeks of yours, Joey. I am going to enjoy doing that very much!” I leaned forward and was confronted with the fattish swell of Joey’s broadened buttocks. I gave her a smarting smack on the near cheek of her backside, and then another, causing Joey’s bottom flesh to compress, and Joey to squirm and utter a curse under her breath.

Next I slowly parted Joey’s bottom cheeks, enjoying a long and close inspection of her tightly closed rear hole. Joey gasped and flinched as I touched the pad of my finger to her tight anal rosebud. I ignored her protests and leaned forward, pushing my my whole face into the warm space between her bottom halves.

Joey let out a loud gasp as she felt my warm breath raft across her anal dimple. I didn’t care. I had to have her. I was really quite mad now with desire, my dick rock hard, my mind aflame with lust, my desire to sodomize her overwhelming. Joey turned her head and watched over her shoulder as I unscrewed the lid to the jar of Vaseline.

She watched, wide-eyed, as I scooped the jelly out of the jar and slowly pushed my finger between her bottom cheeks, running my finger up and down between her clenching bottom. Joey’s bare rear cheeks clenched hard as I found her anus and lightly traced circles around the small ridges of her anal bud. She gasped as I started to slowly insert my greasy finger into her bottom ring.

I stood and nosed my hardened cockhead snugly up between Joey’s clenched bottom cheeks. I let it rest there for a moment, feeling the warmth of Joey’s bottom halves compressed against the side of my cockhead. Joey was clenching her legs slightly, pulling against the leather restraints, her rejection of what she knew was coming causing her bottom cheeks to compress against the hardened intruder and sending little tingles of sensation up my spine.

I felt her move, pulling against her restraints as I let my cockhead find the bullseye of her tight anus. Joey gave a small, unladylike grunt and tried to climb the sofa top as I shifted my weight forward and started pressed my rock hard cockhead into her clenching opening.

The tight anal ring finally expanded and I pushed my hard member forward, feeling her anal ring gripping my dickhead like a tight glove. I pushed a little further, feeding more of my cock past her anal ring, exhaling with the warmth and tightness of her bottom’s grip on my dick.

The sensation was to much for me. I had wanted to proceed slowly, to make this girl feel me master her inch-by-agonizing-inch, but the tightness of her bottom and my excitement at having her completely at my mercy proved to be too much.

With a resolute thrust I impaled Joey on my swelling manhood, and at once I pressed my cock to the hilt. I heard Joey’s muffled whinny, watched as her head shook back and forth rapidly, her hips dancing across the top of the sofa in an
effort to dislodge this rude intruder.

I looked in the mirror positioned by Joey’s head, and smiled at her. “Does that feel rather big in there, Joey?”

I pulled back a little and bound forward hard, impaling Joey once again with the full measure of my hard cock. “God, you have a lovely tight bottom, Joey.”

I kept up the prattle as I rocked my hips back and forth, letting a little of my cock withdraw from her, then sending it hard back up inside her.

I pulled back all the way, leaving just the head of my cock in her bottom, then started to rhythmically sodomize her, first an inch, then back out, then two inches, then back out… until I had fed her all seven inches.

“Ever let a boyfriend play with your bottom like this, Joey? No? I bet they wanted to!”

I rode her helpless bottom for almost 15 minutes, pausing from time to time in order to prolong the delightful sensation. I enjoyed the angry little sounds Joey made each time I would would let my cock slide fully up inside her, her hands clenching and pulling against the restraints, her toes extending, pushing those full hips up over the top of the sofa arm. There was no escape for Joey, her bottom fully stuffed with rock-hard cock, her legs and her wrists tied down, and all her struggles just increasing my already-considerable enjoyment.

anal sex punishment for condemned delinquent girl in prison

Joey was squirming all over the sofa top, variously squeezing her anal ring or pushing her backside out hard in an attempt to dislodge the source of her rather-too-full feeling. The sensation was heavenly to me, her movements sending wonderful little electrical jolts of pleasure up and down the entire length of my cock, and making my balls tighten in their sack.

I was quite out of my senses, really, as I felt my cock on the verge of exploding. Then I could not hold back, and I started discharging, hard, my creamy sperm spurting into her warm
fleshy backside. I could feel Joey’s bottom contracting each time a small spurt of sperm was expelled, causing even more wonderful sensations to my cockhead, which in turn caused even more violent eruptions to be spurted up her ass.

After my discharge, I lay over Joey’s back, my head nestled against the side of her neck, my cock still in her, my breathing labored. Joey had grown rather quiet, and she lay still, her head turned to the side and a sweep of her shiny brown hair covering her eyes.

It was a rather curious feeling, I actually had a growing sense of affection for the girl, with her defiant attitude and robust full bottom. At the same time, I knew that I was going to greatly enjoy the whipping I was about to give her.

I was hardly done deflowering her bottom when my member began to rise again. “Are you ready for your discipline now, Joey? Did you think I had forgotten?”

“First you will get a good dozen with the cane all across that plump ass of yours, and then a bare-bottomed reminder to watch your behavior in the future, Joey, with my leather training lash. I am going to teach you manners this afternoon, Joey. I’ve wanted to do this for a long time. I will have obedience from you!”

I picked up the bamboo cane and swished it through the air a few times. Joey turned her pretty round face back and mouthed a silent “please”, her eyes already reddened.

I smiled back at her, my cock now again fully erect and shiny from the lubricant, and clearly visible to the remorseful girl. “Oh, Joey, poor girl, did you think showing me those big brown eyes and a little pleading would be all you needed to do to get you out of your caning? I want to give you a lesson you will remember for quite awhile, dear girl!”

Holding the cane in my right hand, I stood behind and a little to the right of Joey’s upturned and quivering bottom cheeks. I brought the cane tip up even with my left shoulder, the body of the instrument crossing my chest.

I slowly raised my elbow till it was even with my shoulder, slightly cocking my wrist, and letting the small end of the cane extend up and behind me. Then I quickly rocked forward, shifting my weight to my front leg, snapping the cane forward. The cane whooshed as it traveled through the open air, and I brought it up sharply as it made contact with Joey’s bottom.

I had aimed low, and stung Joey not an inch above the flesh crease dividing her chubby white bottom cheeks from her upper thighs. The impact of the cane across joey’s bottom sounded like a pistol shot.

Joey didn’t move for a second, her body stunned, the impact of the cane too much to respond to all at once. Then her head snapped up, and she let out a low long gutteral moan, her pale skinned rear mounds compressing hard and then surging up as she attempted to defuse the smarting impact of the cane.

I let go with another strike, this time aimed across the middle of both her fleshy white bottom cheeks, pushed back high and in perfect position for the strike. A double red line appeared where the cane had struck, and Joey’s head swept from side to side as her hips danced across the top of the leather sofa.

“Tears already, Joey? We’re just getting started now!” I smiled at the now-sobbing girl, bringing the narrow end of the whippy rattan cane up even with my shoulder once again. “It will be a very long detention for you this afternoon, I’m afraid.” Joey’s bottom was now bounding up and down, her fat bottom cheeks thrusting into the air, her contortions pulling her ass cheeks hard apart.

She turned her head and gnawed her lower lip, her hands clenching into desperate fists, her hips shifting and tensing as she waited for the next strike.

I tapped the cane lightly across the crowns of her milky buttocks, enjoying the caning I was giving her, watching her fleshy rear orbs contorting and quivering. Already, I was thinking about pushing my dick again up her punished backside.

I gave her four more quick sharp strikes across the middle of her smooth white ass, watching as the red lines of the cane became visible. “Do you want to be a good girl now, Joey? Do you want to behave for me?”

“Yes! Yes, yes sir! Please… No more!”

I raised my arm and whipped the back of her bare thighs with two more severe strokes. There were wild protests, and Joey’s ass began to do an involuntary dance that would have made a bride blush on her honeymoon night. She squirmed over the leather sofa, her ass cheeks quivering and her hips raising and lowering, giving her a whorish, wanton look of sensual abandon.

I caned her again across the back of her legs, and then without pause gave her two more across the very bottom of her ass cheeks. I waited for a moment, letting the full impact of the cane strokes sink in. I loved the way she looked, her plump white flesh criss-crossed with angry red welts, her thick brown hair matted and shaken across her pretty face, the look of the black leather restraints across the back of her knees, her ass shaking and jiggling from the smarting effect of the punishment.

Then I raised the cane again, and gave poor Joey four or five fiery strokes right across the middle of her twitching squirming ass.

Joey was long past bouncing her rear up and down. She was weeping, low and deep within her chest, her ass doing slow rotations from side to side, one knee jamming behind the other, then releasing as she pushed her hips up over the sofa top again.

I put the cane aside, and sat down in my chair directly behind Joey. Her ass was a mass of fiery angry welts, some red, some starting to turn a deep purple. The back of her pretty thighs showed evidience of at least 6 or 8 cane stripes. To tell the truth, I had lost count, and wasn’t sure the number of strokes I had delivered. Joey’s head had fallen forward, and her body was convulsed with deep sobs, her ass slowly rotating in small circular motions as she wept.

I reached forward and ran my hand across her reddened ass, feeling her flinch at the lightest touch, and felt the heat radiating from her bottom. My cock again was standing straight out, its head purple and engorged, and it took all of my resolve not to sodomize her again right then.

For the first time, I realized that I was truely in the grip of an obssession. Everything about her had me spellbound. That plump, fleshy white ass, her soft brown eyes, those sturdy legs
soft and tanned from the sun, the way she sat at her desk, even that priceless guilty expression she had whenever she was called to my office.

I wanted to possess her, to discipline her further then I had ever gone with one of the girls before, to make her service me with that crass little mouth under my desk in my office. I wanted to lay her across a pillow on my bed at night and leisurely sodomize her before sleep, or to make her straddle me in the bed, her ass pushed back and spread for my touch. I wanted her wearing a collar and on a leash, black leather around her white neck. I wanted to see her crawl across my office carpet like a pet. I wanted to make her lay on my desk with her legs spread, to make her touch herself. I wanted to humble her, I wanted to possess her completely. And not least, I wanted her to resist me, to be stubborn and wild, so that I could master her, and tame her. I wanted to make her her mine, I wanted to own her. I wanted to make her call me Master and Sir, to make her look up at me with those big brown eyes and to plead with me not to discipline her bottom anymore.

I stood and walked around to the oak armoire, and swung open the door. The shelves revealed all that a disciplinarian could have hoped to find.

I reached in and took out the dispenser of liquid soap and a long pencil-shaped glass squirt with a large rubber ball attached to its end.

Filling the squirt with liquid soap, I again pulled up the chair and sat directly behind Joey’s red, upturned ass. I let my fingers trace up and down the inside of Joey’s cheeks, feeling the heat radiating off her welted ass. I watched as her legs tightened against the leather restraints.

“In the mood for some more fun, Joey?”

Joey turned her head and looked back at me, flipping her brown hair across her forehead. Her eyes were still red, but they grew larger with fright upon seeing the glass squirt.

I smiled back at her, and gently intruded the tip of the soapy squirt into Joey’s anus, giving the squirt a little twirl as the the tip first breached her anus.

Joey’s arms pulled against her restraints, protesting this new humiliation she was powerless to stop. I slowly pushed the six-inch length of the glass squirt into Joey’s bottom, continuing until only the rubber bulb remained visible. Her bottom cheeks tensed desperately at the cool depth of the
glass squirt, and she turned her head in dismay and disbelief.

I then began to squeeze the rubber bulb, and I smiled as I watched Joey’s body give an involuntary shiver at the feeling of the cool, soapy slipperiness so deep inside her behind.

I pumped the bulb two or three more times until I was sure all the liquid soap had been pumped up her ass. Her anus went quite small and tight as I withdrew the glass intruder, and she compressed her ass cheeks together in an attempt to avoid disgracing herself.

“Feeling a need to use the restroom, Joey? You’d better not be rude, I give extra stokes for girls who can’t seem to control themselves during their punishment sessions.” I walked around to the front of the sofa, and gently cupped Joey’s chin in the palm of my hand and raised her head. Her face was a mix of confusion and pain, her mouth held tight in an attempt to check the urges now starting to work inside her.

In my other hand I held the single-tailed leather training whip.

“Having trouble containing yourself, Joey?” I smiled at her. “Maybe I have something that will help.” I showed her the fine penis-shaped whip handle, its length about seven inches, its head shaped with an elongated fat sphere, about the size of a plum.

Joey’s face had turned red from the effort to hold her bowels in check. Her eyes were misty and her breath was ragged, coming in small gasps.

“Oh, please don’t, Sir!” Joey’s voice had turned very small, her request dripping with submissiveness, a signal of a new attitude.

“Not so defiant now, Joey? Where’s that aggressive delinquent the matrons brought down here earlier?”

I walked back to my chair and again sat directly behind the fleshy orbs. I coated the rounded plum-shaped end of the whip’s handle, and adjusted the knob against Joey’s vulnerable anus.

“Since I’ll be taking a half-hour break, you get a half-hour of this whip handle up your bottom, Joey. Perhaps it will be a little uncomfortable, but this is something you can remember, next time you wonder if you should be obedient or not.”

Joey flicked her hair back and twisted her face around. This time there was panic, and her large brown eyes were damp with tears.

“I must say, Joey, I feel a certain amount of pride in seeing your new attitude develop so quickly. Still, I also get a rather perverse thrill when I think about buggering your cute bottom with the same whip I am going to use in a little while across those plump ass cheeks of yours.”

I used my fingers to open Joey’s bottom cheeks wider, and with my other hand I steadily pushed against the whip handle I’d positioned against her exposed anus. She was still strapped down, her buttocks fully rounded, her tight anal cleavage pulled wide open. There was a loud shrill mewing from her as the plum-headed whip handle slowly pressed through her anal ring and plunged deeply into her ass.

I grinned, my eyes riveted to the handle of the whip as the full length slid into her ass. My erection was as hard as a steel rod, standing straight out from my lap as I sat not a foot behind her welted and buggered ass.

After inserting the handle all the way up Joey’s bottom, I then spent several minutes rhythmically buggering her with it. At first I used slow shallow strokes, twisting the plum-shaped head just inside her anus, working the tight anal ring and listening to joey’s soft urgent pleas. Then, I started working the whip handle deeper, very slowly thrusting, pushing the whip handle all the way into her bottom, holding it there for a minute, then slowly working it back out, inch by inch, as she clenched and moaned and whimpered.

Joey was stretched harder than she ever could have thought possible, her anal ring stretched wide against the thick whip handle, her insides by now giving off terrible cramping bursts of urgency as the liquid soap started working.

I watched her muscular cheeks writhing and contorting in such a sexually suggestive way, and I wondered if I would be able to wait the whole 30 minutes before I gave her a lesson with the leather pony switch, and before my aching cock could replace that lifeless whip in her hot tight ass. Then I pushed the whip handle all the way in, as quickly as I could, and let go of it. The natural contractions of her anal ring pushed the handle back out, until it got to the plum-shaped whip head, which was considerably larger then the body of the whip. That held fast.

I gave Joey three or four smarting hand spanks across her purple welted ass cheeks, watching her legs contact, and her ass cheeks bounding with each spank.

“I’ll be back in half an hour, Joey. Be ready for the rest of your punishment!”

See Also:

  1. Spank Slaves Spanking Porn » Caning And Buggery commented on January 21st, 2013:

    […] And Buggery: Reform school punishments Three more […]

  2. A Bit Of Bondage Buggery – Bondage Blog commented on January 22nd, 2013:

    […] Joey’s Punishment as seen at Spanking […]

  3. Janet commented on September 10th, 2019:

    I’m sure it does exist:

    Spank me if I am wrong. :)

  4. SpankBoss commented on September 10th, 2019:

    Not gonna, but I think you may in fact be wrong. I see “Joey’s Detention” on that page, which as I noted in the post is one of the two stories that has big chunks of prose in common. I don’t see this exact story or anything titled “Joey’s Punishment”, sorry!

Leave A Comment

Maximum Comment Length: 2500 characters (about five paragraphs)