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Cindy’s Prom
My slave had been slightly less responsive for the previous few days. Once in a while she gets the blues. Sometimes I think she just isn’t cut out for all the pain, abuse and degradation she gets. Then I think of her perfect tits, begging for a whipping or her pouty lips, ready to part and accept me in her loving mouth once again. I know she’s made to be my personal rape doll.
I had gone into the basement that morning and shared breakfast with my pet. She had trouble eating with the ring gag in her whore mouth but I certainly enjoyed watching her. After she dribbled yogurt all over her tits I didn’t mind cleaning her up. Even with our pleasant meal she was still sulky. Fortunately for her I was in the mood to indulge her rather than give her a more immediate reason to be upset.
That day I was planning to spend some time relaxing with my slave so we made our way to the chair to watch a movie. I picked one of Cindy’s favorites, it’s actually one I took from her apartment when I made her mine. I sat down in the comfortable master’s chair and Cindy did her best to settle onto the hard wooden stool, the ring gag still holding her jaws apart and her best friend nestled inside her.
We both had beverages and I smiled to myself when she dribbled onto her flawless breasts. For once I didn’t take advantage of an excuse to punish the dirty slut. By the end of the movie she was dry, except for her eyes. They were dewy with moisture and she had to constantly blink the tears away, it was unbelievably sexy.
“Come here and present yourself, slave.”
Cindy stepped in front of my chair and cupped both her breasts in her hands for my viewing pleasure.
“Lean forward.”
“Eh ur,”
was her adorable attempt to give the appropriate response. As she brought her head and chest closer to me she continued holding her perfectly hurtable breasts even though the lovely way they hang down slightly made it unnecessary. I reached behind her neck and unlocked the strap holing the gag securely in place.
“Go put that away now, sweetie. Bring back the metal handcuffs. Wash up first, you drooled all over yourself.”
Cindy nodded and turned to her assigned task. I was feeling caring, ready to hold my precious whore and let her release some emotions. I’ve found that Cindy likes to wrap her arms around my neck when she buries her stunning face in my shoulder for a good cry. I love taking that little comfort from her by locking her hands behind her back with cold, unyielding, steel cuffs.
When she returned, carrying the restraints, I had her straddle my legs facing me. Her tight fuck hole would be in position if her upcoming sob session got me worked up and I had to push my hard cock inside her. I took the cuffs in my right hand and grasped her delicate throat with my left, pulling her in for a deep kiss.
As I held her in that passionate embrace I reached around her waist, pulling her wrist back. With plenty of practice I’ve gotten good at securing the heartless bracelets with one hand. Cindy knows her best option is compliance and she was soon without the use of her arms. I drew back and brushed her cheek gently, asking in a sympathetic voice,
“What’s the matter, cupcake? Have you been feeling sad?”
Cindy nodded hesitantly. I looked at her questioningly and eventually she looked down and uttered,
“I, I just miss the way things used to be, and, and then the, the movie reminded me of watching it be-before.”
“Before you came here with me?”
“Mhh hmm.”
I lifted her delightful chin to look into her sorrowful eyes.
“I know it was hard, it must have been a big change for you.”
The poor thing nodded, closing her eyes and trembling in my reassuring arms. When she looked back up to me her lower lip was quivering and I knew she was on the edge of breaking down. That moment, just before the tears start, is one of the most beautiful things in the world. Whether it’s caused by pain, humiliation or just pure anguish I love knowing that I caused my wonderful pet to feel that way. And I love her. It gives me such satisfaction and pleasure to have complete control over my Cindy and to abuse that power so terribly.
That’s when, as she’s about to edge over the line into true misery, I simply can’t resist giving her a mean-spirited shove.
“Going from thinking you’re a normal person to finding out you’re just a gorgeous, soft body to be hurt and a set of holes to be used.”
That did the trick and my toy collapsed onto me, sobbing uncontrollably. I pulled her tight to me, arms around her shaking frame. As I leaned my head against hers I felt the hot tears run down my neck. Brushing her hair softly with one hand I consoled her,
“It’s ok, slut. Sometimes filthy whores need a good cry.”
I hope my little princess remembers this kindness the next time I restrain her, cane her helpless tits raw and then beat her cunt until she screams herself hoarse and I have to force my way into her swollen love hole. I sometimes worry that she doesn’t appreciate all the effort I put into our relationship.
My dejected little plaything had me almost painfully hard and I reached down to guide myself into the warm slit begging me to use it. I started taking small strokes in time to my fingers brushing her long brown hair. Her hips matched the rhythm and we were soon slowly and steadily fucking each other.
I doubt Cindy even realized what she was doing. She was enveloped in her own little world of sadness. Conditioning is an amazing thing. Even at that moment some part of her knew that if she didn’t grind her silky fuck hole down on me the right way there would be a brutal punishment in her near future.
I could have stayed there forever, buried inside my good girl. I held her in my embrace and moved my hand up and down her back, occasionally pressing on her butt plug for a few strokes. For her part she continued shedding tears and slowly bouncing on my cock. She’s just perfect.
All good things must come to an end and eventually Cindy’s breathing slowed and she began to relax. I turned my head and softly kissed her pretty neck. Moving both hands to her steadily rising and falling ass I palmed her shapely cheeks. As I nuzzled her neck I felt the sensations and emotions overload her mind as she gave in to a relief filled orgasm.
I could hear her catch her breath over and over before letting out a gentle “unh” each time, the way my slut does as she climaxes. Finally, the heat radiating from her tits to my chest pushed me over the edge and I joined her in bliss. I swelled slightly more, my body instinctively attempting to get that much deeper into her belly and I sprayed and sprayed my semen inside of her.
After reluctantly lifting her off of me and removing the cuffs I knew we were both ready for a nap. She was tired but managed to follow as I carefully led her by the hand to the door of her house. I picked out a deep blue bra for her and a matching, medium sized ball gag. I placed it in her waiting mouth and locked it behind her neck.
My cock began to stir at the sight of her so exquisitely silenced but we required rest and I needed to prepare the surprise I had in store for cheering her up. After giving her a peck on the forehead I pushed her down to her hands and knees. Cindy crawled into the featureless metal box and I closed the door behind her, sliding the bolt into place ensuring she stayed where she belongs.
I took a quick nap and then went down to prepare for Cindy’s special evening. She missed the way things used to be and I was going to recreate one of those memories for her. Well, with a little added fun, of course.
Around 4:00 I retrieved my slave from her house. After I unlocked her pretty ball gag she dutifully returned it and her bra to their designated places. My cock was hard in anticipation so I made her fetch a pair of clothes pins. After arranging them just right, hanging straight down from their grip on her nipples and holding enough flesh to keep it from being immediately painful but little enough that the pressure would cause the pain to slowly build, I guided my beautiful whore to her knees. She began to suck as she’s been trained, taking me deeper and deeper with each bob of her head until those sexy little noises started escaping while she accepted me into her throat.
This was just an appetizer, I didn’t intend to cum yet so I reluctantly willed myself to withdraw from her talented mouth. I told her to make herself pretty for me and even allowed her the luxury of a full bath without earning it. As she padded away on her bare feet I smiled at the thought of her special treat being tainted by the growing pain in the delicate tips of her breasts. She knows better than to take them off, even in the privacy of the bathroom.
Cindy emerged from the restroom looking and smelling like heaven. It was difficult not to take her immediately but I was patient, it was going to be even better later on. There was a garment bag hanging from a hook on the wall. I handed it to her, explaining,
“This is what you’ll be wearing tonight, dear. What do you think?”
She opened the bag and immediately recognized the contents. Her eyes widened and her jaw even dropped slightly in the cutest little stunned expression. In her hands she was holding her old prom dress, another reminder of her old life I’d thoughtfully included in the collection of things I took from her place.
“Will you be my date tonight, slut?”
Cindy was staring at the dress like it was from another world, which, for my fuck toy, it was. Through her shock she managed to obediently reply,
“Yes, sir.”
I removed the clothes pins and massaged her nipples, squeezing just a little more pain from them before helping her into the dress. It was a deep blue color and it hugged her shapely figure from top of her chest down to just a few inches above her knees.
It was sleeveless and low enough to show her chest beginning to swell underneath but modest enough to hide any cleavage. It fit like a glove but didn’t seem uncomfortably tight anywhere. I was very pleased with her appearance and complimented her,
“That looks fantastic on you. Aren’t you glad I helped you lose those extra pounds? A few weeks ago your tubby ass wouldn’t have fit in that sexy little dress.”
She had been a pound and a half too heavy at her last weigh in but five days of the cum-only diet had whipped her back into shape. Along with several literal whippings during which she screamed her poor heart out and apologized for letting herself become so unattractive.
I lead her over to the vanity and placed a photograph at the edge of the mirror. It showed a proud, excited Cindy ready for the big dance just a couple years ago. She looked so innocent, it’s hard to believe all the filthy, degrading acts she’s now only too eager to perform in exchange for some trifling kindness. It makes me laugh.
I generously allowed my slave to suckle my engorged cock as she valiantly tried not to cry. I slowly dragged in and out of her face hole until eventually a few drops escaped down her flawless cheeks. Wiping her dry with a tissue I explained,
“No more tears, now. It’s time to do your hair and makeup, just like the picture, honey.”
I put on the cheap rental tuxedo I’d picked up earlier. I wanted this to be as authentic as possible for my good girl. I was soon dressed and I sat down to watch a movie while Cindy prepared herself for me. On the screen her beautiful, terrified and penis gag filled face stared forward. Her muffled screams and moans were accentuated by the loud impacts of the leather strap across her outthrust buttocks.
It took her a while to get ready. I was patient as I wanted her just right and it was worth the wait. The hair was difficult as I’m sure she’d had it done professionally the last time but she did a very good job on her own. She stepped into her heels, completing the picture. I lifted her hand, kissed the back of it and lead her through the doorway.
The lights were turned low and there were streamers and a disco ball transforming the punishment room into an enchanting fantasy world just as effectively as any gymnasium ever had been. I used the stereo remote to start some uninspiring dance music from two years prior. Cindy glanced around nervously, no doubt in awe at the magic and romance of the scene. Most of the furniture had been cleared to the sides of the room but her eyes lingered on the school desk standing alone under a soft light.
She knows the desk well. It’s a typical school desk with the chair built into the small writing table in front of it. There are more restraints on her desk than most others but it is still functional and she’s spent many hours at the desk taking long tests in her slutty schoolgirl outfit, her best friend pushed up inside of her.
I usually gave her a week to study, a reading light and textbook thoughtfully left in her house. She’s very clever and scores well. She once aced a test and spent quite a while on her birthday sybian as a result. All her other exams have been imperfect and I’ve been forced to bend her over the front of the desk, lift her cute plaid skirt and thrash her naughty ass with a yardstick as she desperately corrects her mistakes on the seat of the chair.
Once she finally gets it right I leave her strapped down and use her tight cunt. I don’t know if that role play taps into some fantasy of hers or if that position just does it for her but my slave usually cums once or twice while bent over the desk before I pump my semen into her.
She wouldn’t be taking a test or having any orgasms at the desk that night but it would certainly see some use. I placed my arm around her waist, pulled my Cindy close and began to dance with her. She was nervous and stiff but she gradually relaxed in my caring arms. I took the chance to enjoy feeling my slave’s body through much more clothing than she is usually allowed. The dress fit close to her trim figure but slid pleasantly over her skin as my hands glided up and down.
Soon she had her head resting on my shoulder as we swayed slowly. Her hands were curled toghether, arms folded between us as I drew her close. I kissed her neck and brushed a hand over her silky hair while the other cupped her strong, perfectly shaped ass. I would attend to that shortly.
As we danced, lost in our embrace, I’m sure, a certain song came on. It featured heavily in the otherwise random mix I had playing. I whispered,
“This is our special song.”
I took her roughly by the arm and pulled her over to the desk and was able to secure her quickly. I stepped over to the wall and took a long, heavy paddle from a hook. It’s about four inches wide so it spreads the impact out but with the weight behind each stroke it turns poor Cindy’s bottom red in no time.
After the red more beautiful colors continue to bloom but they wouldn’t be seen that evening. I left the dress in place, pulled snug over her bent form. For the duration of the song I beat the hell out of her protruding ass. She thoughtfully added her screams to the music in the air.
When the song ended I put the paddle away and released my whore. She hesitantly stood up, looking away fearfully. I drew her in again and resumed our dance. Soon the special song played again and it was back to the desk for Cindy.
More pain, more dancing, over and over. At the end of each song my date would begin to fidget, anxiously waiting to learn what would play next. Whenever my hand rested on the swell of her cute butt I could feel the heat rising from it, even through the smooth fabric. I could have performed this dance all night, alternating between beating and comforting. I needed relief though and after the couple hours I had planned I was ready to explode.
Our special song played and my special girl was paddled accordingly. Then the song played again and I paddled her some more. The third time was just too much and she broke down, sobbing uncontrollably while I struck her without interruption. Underneath the unchanging dress must have been a mass of bruises and inflamed flesh.
When the music finally stopped my red-eyed, tear-streaked angel was ready for our formal picture. This would make a wonderful addition to Cindy’s scrapbook. Yet another cherished memory for the two of us.
She had a hard time staying upright but I supported as we made our way over to the arch of flowers with the camera and tripod in front of it. I set the camera timer and brought my prom date over to the correct position. I let her lean on the archway and leaned over to grasp her dress. I tore it apart at the convenient seam up the back, just for a few inches near the bottom.
Through the hole I withdrew her plug. I placed it in her hands, wrapping her fingers around the base and lifting her arms in front of her as if she were holding a bouquet. I knew she must be happy to have her best friend in such a meaningful photo.
I bent my legs, aligned myself and hugged Cindy’s torso. As I stood up my cock was pushed into her squeezing asshole. I continued rising until I was standing straight. I was holding my slave up, her feet actually off the floor. I let as much of her weight as possible down on my erection, forcing myself even deeper into the valley between her undoubtedly burning cheeks.
The camera flashed at just the right moment and captured the expressions on our faces for later reminiscing. The look of satisfaction I have in that picture makes it clear I had found my place, fully inside her bottom. This is confirmed by the round shape of her mouth, mid gasp. The wetness of her cheeks makes it clear she was still shedding tears. The only other thing that appears out of place is the plug.
I brought my good girl back to her desk and fastened her down one last time, keeping myself embedded in her warm tush. Once she was secured, still grasping the plug in one hand, I began pounding into her, giving her ass a thorough fucking and slamming my hips and thighs into her soft, pain-filled curves. It wasn’t long before I found myself thrusting desperately, aching to be deeper as I pumped her full of my cum.
My energy spent, took the toy from her and slid it back up her rectum. I unbuckled my slave and she knew well enough what was next. Cindy unenthusiastically moved to her knees and took my slowly softening cock in her mouth. Her makeup was even more attractive smudged and lined. As she sucked, a trace of lipstick was left on my cock. I smiled, knowing that it would be cleaned off along with anything else she had left on me.
The excitement of the evening cut down my usual recovery time and I was treated to another orgasm as she took me down her expert throat. After spraying my seed into both ends of my toy it was time for bed.
As I tucked Cindy in for the night, allowing her the luxury of keeping the dress on in her cold, metal box, I hoped that the enchanted event had cheered her up.
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