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Old 04-11-2012, 12:44 PM   #106
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Awesome story! Its not just that the events are hot, but the way you tell it is fantastic! Can't wait to hear who is dressing up like a sissy slut...
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Old 04-12-2012, 01:32 PM   #107
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Alright.....I know a few days ago I said I'd have next chapter in but life happens sometimes lol. A lot of factors go into writing stories and for some reason I just wasn't in "the mood" the past couple days. I love hearing from you all though and that definitely keeps me going so thank you to everyone who has commented for the positive feedback! I had the day off from work today so I tied myself down and finished a rather long chapter! Hope you enjoy!!!


Miss Jenn smiled as she put the finishing touches on my makeup and stepped back to admire her work. For the past hour, I have been transformed into a sissy slut and wasn’t too thrilled about it. My toes painted a deep shade of red, fitting as it matched the color of my ass after I initially refused for my legs to be shaved. Personally, I have never been a fan of wearing women’s clothing and when Master Simmons demanded my legs to be shaved, I protested. In hindsight, I wish I hadn’t as now I sit with Master Simmons worn underwear in my mouth, smooth legs, and the heat radiating off my ass could be mistaken for a stove top. In addition, I have been fitted with a cb6000 series because “sissy cocks need to be caged”, my nipples clamped underneath a sports bra, a pink thong that’s way too small for me which holds a butt plug in place, and to top it off a face full of makeup. Dan, Master John, and Miss Megan were in the other room preparing dinner as Miss Jenn and Master Simmons admired their work. The moment I heard that I had lost, I was overcome with disbelief, confusion, and pure fear of the evening I was now about to endure.


Miss Jenn placed a pair of 6 inch heels in front of my feet and instructed me to put them on.

“Aw, you look so beautiful slut! Let’s see you walk around a bit. Work that ass and show off your sexy legs!”


After just two steps in high heels I have a newfound respect for all the ladies that wear heels on a regular basis. There was nothing sexy about the way I walked as I basically stumbled back and forth to the amusement of Master Simmons.

“Keep your head up bitch boy, walk proud! Up on your toes and sway your ass back and forth!”


It took me the next twenty minutes or so to get to a level that both of them were satisfied with before Miss Jenn delivered the first of several bone chilling announcements for the evening.

“Master Simmons has asked to take you out for a walk on the trail that leads to the park. I have decided this is a great idea and you will be released into his custody for one hour while the rest of us finish up dinner arrangements here. Since we all want to be there for him pounding your ass, he will not be fucking you during your walk. Other than that, he has full authority. Luckily for you slut, the trail is mostly private property owned by me until you reach the park. Enjoy your walk and be a good girl!”


My reaction to this got me a swift hard slap to the face from Miss Jenn and I bowed my head realizing that I let my emotions get the best of me. I knew that if this is what Miss Jenn wanted then it didn’t matter how I felt about it and I was ready to accept my fate. Miss Jenn provided me with a short skirt to wear over my panties which I appreciated very much. She kissed me on the lips which smeared my lipstick a bit and slapped me on the ass as I was collared, leashed and handed over to Master Simmons at the door.


Master Simmons was wearing a tight tank top showing off his rippling muscles and shorts that showed the bulge in his groin. He had a firm grip on my leash as he led me down the steps and to his car. My walking in heels was still very amateurish and I almost fell as I struggled to keep up. He grabbed a blonde wig from his trunk and placed it on my head to complete my transformation.

“Now, you really look like a slut! A little too muscular for my liking but that sports bra looks so sexy on you with your six pack. If you do as I say, there will be no trouble, but if you choose to pull any of the whining shit you pulled inside I’ll tie you naked to a tree, make a few phone calls to some friends and then leave you there.”


He yanked on my leash and we began our walk to the backyard where the beginning of the trail was waiting. I struggled to keep up for the first 50 yards of the walk due to my obvious inadequacies with high heels. With each tug on the chain I was pulled forward and my body began to ache. He asked several questions about my relationship with Mistress and I actually was becoming more comfortable with him as we continued deeper into the woods. When we reached the middle of the trail I was ordered to take off my skirt which left me in a pink thong and matching sports bra. He roughly worked my body over touching my ass, clamped nipples and ran his hands from my calves to my caged cock. I turned red with embarrassment as I was being felt up and tried to pretend it wasn’t really happening.


“Leave your skirt and take off those heels. We need to get moving and you’ll be faster barefoot. We will grab them on the way back.”


I was actually thankful to ditch the heels and even though the dirt was rough beneath my feet it was much easier to walk at the pace Master wanted. We reached the end of the trail that led into the park relatively quickly and ventured just off the trail into the brush. We were not into the open area of the park but I was freaking out about the potential of being seen! We stayed in the cover of the trees but I was certain the area Master chose to stop was visible to people walking in the park. Master roughly pushed me to my knees in front of him onto several sticks, leaves and dirt. I immediately felt the sting of scrapes as I kept my head down waiting for instructions.

“Take off my shorts with your teeth boy. Hurry up, we are running low on time. Be careful cause I’m not wearing any underwear and if you bite me, I will kick your teeth in!”


Without any other options I latched on to his shorts and maneuvered them down to his ankles. He stepped out of them and grabbed something from the pockets and lifted my head. His rock hard cock was at eye level and I closed my eyes as I knew my fate. Master Simmons took off his shirt revealing his toned, hairless chest. All 11 inches of his cock was staring me in the face as his words sent shudders down my spine.


“I’ve been waiting a long time for this slut. You are gonna take all of my fuckmeat deep down your throat. I’ll start off easy because I know this is your first weekend worshipping real cock. Don’t worry though, by the end of our time here, I will be fucking your throat so hard and deep it will be like you’ve been doing this for years. Now, start by licking the head like a good slut.”


I didn’t dare protest and accepted his cock head into my mouth. He slowly began to thrust as I licked the tip and a few inches entered my mouth. I concentrated on relaxing my throat muscles knowing that I would need to take more than both the previous cocks I had sucked that weekend. Master Simmons reached down and grabbed my leash and yanked it tight forcing more of his cock into my throat. My gag reflex kicked in and the choking sensation took over my body. I fought for air and he pulled out leaving me gasping to catch my breath. I realized now that in his other hand was his cell phone, capturing every humiliating moment so far.

“Smile for the camera bitch!” He said with a laugh, “Aw, looks like your mascara is dripping, don’t cry little slut..this is only the beginning”


He forcefully re-entered my mouth and I knew that my recovery time was over. Grunting, he forced more of his cock inside and filled the back of my throat with his cock head. Again, I gagged and could feel the tears rolling down my cheek as I fought to regain my breath. There was no break this time and as soon as he pulled out he re-entered and thrust his full length into me without a care in the world. His cock slid down my gullet and the sloppiest blowjob was in full effect. There was nothing gentle about the next several minutes as he used my mouth as his own personal pussy and rammed my throat with the intensity of a wild animal. His balls contacting my chin, with each thrust hitting me harder than before as I drifted in and out of consciousness. His moans began to increase and without warning he pulled out and unloaded all over my face. Several loads began dripping from all areas of my face as he made me look into the camera and smile. Some of his cum went into my eye and the sting was unbearable.

His softening dick was inserted into my mouth and I cleaned him without objection as my spirit had been broken. He put his shorts back on, ordered me to my feet and we began the walk back to the house with cum still dripping on my face and chest.


We walked back in silence and at a much faster pace as the high heels were now in my hand instead of on my feet. We arrived back at the house and when the others saw my dripping makeup and the dried cum on my face, they applauded and shouted with glee. I bowed my head and was sent to shower with the instructions to keep the butt plug in my ass and nipple clamps on at all times. As I crawled away to shower, Master Simmons had his cell phone out and was proudly displaying my performance for the others.


I have never felt so dirty in my life as I stood in the shower and tried to wash off the feeling of filth from my time in the woods. My knees seemed to be permanently stained and my feet looked embarrassing with my toes painted. After toweling off, I looked at myself in the mirror with my cock still in captivity and stared at the slave before me. Even after the events that just transpired I was proud to be a slave to my Mistress and hoped she would be just as proud of me.


I returned to the kitchen area naked where Miss Jenn was the only one in sight and she greeted me with a kiss. She always seemed to brighten my mood and right now was no exception. She was in a pair of tight booty shorts and tank top that complimented her tan skin and drove me wild!


“What a lovely performance by a true slut! Master Simmons was pleased with your effort and can’t wait to continue with your punishment. I have a secret to tell you but that will have to wait until morning. Tonight, will most likely be one of your toughest nights as a slave but I know you will do great! The others are downstairs in the dungeon preparing for your evening. Take some time to eat the leftovers and I will come up to get you when we’re ready. Keep making me proud babe, you are doing great!”
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Old 04-12-2012, 02:12 PM   #108
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The story is still hot but man, you are a bad slave. Even on the challenge you won you still needed to be punished. Dan seems much better.
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Old 04-12-2012, 02:25 PM   #109
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True...telling the story from my perspective as I don't know what Dan went through on his side of the challenges. Bad slave seems a bit much but to each their own
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Old 04-12-2012, 02:27 PM   #110
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Nom nom. I love you again
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Old 04-15-2012, 09:22 AM   #111
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Another chapter coming this afternoon!!

Hope you enjoy!
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Old 04-15-2012, 09:39 AM   #112
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wow very good....I would have loved your slave olympics in action so hot.....
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Old 04-15-2012, 09:55 AM   #113
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I can hardly wait.
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Old 04-15-2012, 03:38 PM   #114
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Can't wait for next chapter, please hurry
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Old 04-16-2012, 10:28 AM   #115
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Greetings all....New chapter below...a bit shorter than usual but I got busy at work and whatnot. Am hoping to continue writing this afternoon and upload another as well. Thanks for sticking with me and for all the nice comments! It definitely helps get me in the mood to write!

I sat in silence and ate the leftover meal that was placed before me. Under different circumstances, I would have loved the steak, potatoes and bread sitting on my plate but each bite brought with it the taste of Master Simmons cum that was still lingering in my mouth. Memories of the weekend came flooding back to me as I sat there alone and I felt so dirty reminiscing about sucking and being fucked by real cock for the first time ever. I truly was a slave that would do anything for his Mistress and this weekend proved that. My thoughts were interrupted by Miss Megan as she came upstairs in just a thong and informed me that my presence was requested in the dungeon. Seeing her gorgeous body and full breasts staring at me was all the motivation I needed to get up and begin the walk of shame down to the dungeon to receive my punishment.


I humbly entered the dungeon and immediately fell to my knees and crawled to kneel at Mistress’s feet. This was protocol in her dungeon and the last thing I wanted to do was upset Mistress in front of her friends. Mistress was very proud of her dungeon as she continued to add items to make it a most terrifying place.

Below is a list of the items inside the area:

Two Leather Couches- Used as a viewing/conversation area

60inch Plasma TV secured to wall- Usually with porn or in today’s case- footage of the previous Slave Olympic Events

Several wall displays/equipment holders that include her collection of whips, dildos, butt plugs, rope, gags, floggers, clamps, paddles, etc

Hoist-attached to lifting hook- pulley system

A-Frame
Bondage Table
Queening Stool
Saint Andrew’s Cross
Bed-with bondage capabilities
Sling


Miss Jenn’s face brightened as I knelt at her bare feet and awaited further instructions. I must have missed her entrance earlier when I was in the shower but Master John’s slave girl (Sarah) had arrived and what a beautiful slave she was. She was blonde with a petite build and tanned skin tone. He breasts (34c) were firm with each nipple showcasing a piercing and complimented her toned stomach nicely. Her pussy was completely shaved and another piercing adorned her clitoris. Her shapely legs and feet completed the package and made her one sexy slut.

The scene unfolding before me turned my face a deep shade of red in anger as I realized it could be instead of Dan! Slave Sarah was currently on her knees servicing Dan’s cock with her hands tied behind her back. The way he was throat fucking her made my cock stir in its’ cage as my jealousy raged on. Miss Megan had taken her place behind slave Sarah and was finger fucking her pussy so hard I could hear the slapping as her fingers interacted with the wet and juicy pussy. It was pretty clear that Sarah’s pussy had been used on a regular basis considering the length of Master John’s cock.

Master Simmons and Master John were both on the couch with Miss Jenn enjoying the show in front of them. Both men were wearing leather harnesses with a cock ring attachment and the hardness of their cocks made me extremely nervous for later. I continued to stare at Dan roughly forcing his cock deep into Sarah’s mouth when Miss Jenn smacked me hard in the face with her foot.


“You didn’t earn the opportunity to watch them bitch boi. Make yourself useful and worship my pussy.”


She grabbed my head and buried my face in her pussy. I slowly sucked on her clit as I alternated licking all the places that drove her wild. Within minutes she had a handful of my hair and was forcing my tongue deeper inside her. She began bucking and I knew it was only a matter of time and sure enough, I was greeted with her lovely juices on my face. After making sure she was clean, I turned and saw that now Sarah was in the sling and receiving an incredible fucking from Dan. Only he wasn’t fucking her in the pussy. Her ass was being pounded and again I felt all kinds of emotion knowing that I should be the one balls deep inside of her. I barely had time to catch my breath as my head was grabbed and forced down onto Master John’s cock.


“My turn slut! Let’s cut the bullshit this time. Deepthroat my cock or you might have some trouble breathing. You should be a good little cock sucker by now!”


I made the decision while eating dinner to completely let myself go and try my best no matter how terrible the task was so I dove onto his cock with a vengeance and swallowed him balls deep. I felt all the warning signs of unconsciousness as my eyes bulged and airway was cut off but I continued to work his shaft using my time at the tip to catch my breath before I took all of him again. Master John was enjoying every minute of my newfound sluttiness and enjoyed the panic I felt when I couldn’t breathe. The slurping noises coming from my mouth made me feel like I was a star in the porn business as I tried to concentrate and help him reach orgasm. After several minutes of intense face fucking Master John twitched and sent an explosion of cum into my mouth. He ordered me to keep it all on my tongue and then show him before I swallowed his load. As humiliating as it was to hold his warm cum in my mouth I was relieved to have pleased him and not suffered any punishments in the process. Master Simmons broke the silence as he delivered a chilling announcement.


“Alright, that’s enough pleasure for you right now slave boy. You deserve to be punished for how shitty of a slave you were in the Olympics. When I’m done with you…you are going to be BEGGING me to fuck you senseless. Welcome to Hell!”

He roughly grabbed me and pulled the butt plug from my ass.

“I want your ass to tighten up a bit before you get the fucking of your life. Jenn, let’s get this cock cage off him and get him strapped to the cross. His little clitty cock is about to be introduced to my flogger. Should be one hell of a show”
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Old 04-16-2012, 10:37 AM   #116
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Omg you can't stop there! This isn't fair. I check the site at least a dozen times a day - more when you say you are working on a new chapter. Please don't leave us hanging for long.
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Old 04-16-2012, 02:14 PM   #117
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Omg!, such a hot story which just keeps turning me on more and more, can't wait for more, just makes me so wet, can't help touching myself when i read it
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Old 04-16-2012, 02:30 PM   #118
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Hey fans! With some extra motivation from SarahSarah who helped me get in the mood with her sexyness chatting with me while I wrote, I have completed another chapter. There's a lot of things going on in the story so I'm sorry if I lose any of you when you are reading it but hopefully you enjoy! Plenty of chapters to come! As always....keep commenting or PM me...I love to sign on and see new comments!

Slave Sarah laid in the sling with Dan’s cum oozing from her asshole as I walked by and winked at her to let her know I felt her pain. My cock had been released from its’ cage and was slowly returning to form as Miss Jenn began to strap my limbs to her newest addition to the dungeon, The Saint Andrew’s Cross. I’ve only been strapped to this once and my ass was whipped severely. This time, I was facing out and my heart dropped as I saw Master Simmons grab a fierce looking leather flogger from his bag and snap it with a flick of his wrist. I looked down at Miss Jenn as she locked the final strap on my ankle and rose to meet my gaze. She moved in for a kiss and then pulled back and kicked me right in the balls with a smile.

“Sorry slut, I have no sympathy for you. You failed to win the Olympics and now are to submit to our punishment for you. You look quite sexy all spread on my beautiful cross but there’s something missing. Ah, I know…I’ve got some alligator clamps for those nipples of yours! We’ll have some fun seeing if Master Simmons can force them off with his flogger!”


Miss Jenn went to her wall of devices and grabbed her favorite pair of clamps and returned to the cross. She seductively started licking my nipples and flicking them with her tongue before violently clipping them and laughing as I squealed in pain. She turned to Master Simmons and gave him a long kiss on the lips before pulling a chair over for a front row seat to my misery. Dan had joined us as well and was obediently working Miss Megan’s pussy as she waited for the show to start. Master John was removing Sarah from the sling and already beginning set-up for her next adventure as Master Simmons stepped up with a menacing look on his face.

“What a sweet little slut we have here. Why is your cock hard little slave? Is it because you want daddy’s dick in your ass? You won’t get my cock that easily…you are gonna beg for it but first we have some business to attend to. No one gave you permission to get hard you dumb slut! Let’s see what daddy can do about that.”


Master Simmons started a twisting motion with his wrist and I instantly could tell he was an expert flogger and my eyes bugged out of my head as the first feeling of leather struck me directly on the tip of my cock. I grunted in pain as the next several shots sent me into a rage as I pulled at my bonds and started cursing like a mad man. Miss Jenn immediately grabbed a ball gag and strapped it over my mouth.


“What a dirty mouth you have slave boy! I will make sure we take care of that dirty mouth later on! Back to work, Master Simmons! Make this piggy squeal!!!!!”


After my cock had taken countless shots and was no longer hard I could hear Miss Jenn moaning and telling him to whip the shit out of my nipples. Master Simmons gladly obliged as her began to torment my upper body expertly snapping the cords across my chest. The clamps tightened their grip on my nipples after each painful hit and I fought hard to stay quiet and show how tough I was. Master Simmons was amused by my idea and each strike came with extra emphasis and accuracy. The crisp sounds of the smacks were evidence of his pinpoint accuracy and I began drifting in and out of consciousness which elicited cheers from the gallery. Master Simmons stopped his barrage of strikes and came close to examine his damage.


“Aw, poor slut’s chest is bleeding a little bit. Looks like he isn’t as tough as he thought he was. Well don’t worry bitch boi…I’m just getting warmed up!”


He turned back around and wasted no time on his new target. My balls! I screamed into my ball gag as my cock and balls were violently flogged with increasing intensity as all the members of the gallery watched with delight. Dan was still working Miss Megan’s pussy and Master John had come over to give Miss Jenn a ride and she bounced on his cock while watching her slave boy get the flogging of his life right before her eyes. The final blow caught me square and turned the lights out as my body shut down and the crowd erupted.


It turned out I was only out about 5 minutes as I awoke after Master Simmons smacked me in the face. The ball gag had been removed from my mouth immediately after I lost consciousness and the pain all over my body was unbearable. Master Simmons stared into my dazed eyes and said,

“You ready to beg for my cock in your sluthole now bitch boy?

I swallowed my pride and gave it my best shot….

“Please Sir, I can’t wait for your massive cock to rip me open and pound my insides. A slut like me needs to be pounded in my pussy by a man like you. I wish I had a cock like yours and want it inside me Sir. Please give me your cock!”


“Aw, you are pathetic! You think you deserve my gorgeous cock anywhere near that cum dumpster ass of yours? You couldn’t even beat a limp dicked slave in the Olympics? You aren’t getting my cock this easy. I told you before….this is only the beginning!
Hey Meg, you told me earlier about something you wanted to do with the slut. Let’s get him off the cross and settle him into your idea. I’m gonna take a quick break with Master John and introduce myself to his slave girl Sarah.”

Miss Megan smiled as she came to release me from my current predicament. I saw her eyes travel to the hoist pulley system in the corner of the dungeon and seemed to read her thoughts as she laughed and said,


“Let’s see how much weight your balls can take….hell…maybe I can separate them so far from your cock that you won’t just be dressing like a girly slut, you’ll really be one!”
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Old 04-16-2012, 04:11 PM   #119
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wow so hot thinking of you getting that punishment is hot....
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Old 04-18-2012, 04:13 AM   #120
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Long day at work ahead but then will hopefully be in the mood to write another chapter this evening....

Should be a good one! As always, feel free to leave some love!
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