Slave Olympics
 

Greetings,

I've been a member for awhile now but haven't been very active the past few months since it seems there are a multitude of male "slaves" around here so I figured i would just get lost in the mix. This is my first try at posting a story so bear with me please and have some patience. If it isn't for you then just move along and keep your nasty comments to yourself :D

Some quick "character" background and then I will get on to part 1 of the true story that happened to me about a year ago. I am writing it from memory and when I have time so again....patience would be appreciated!

Justin (me)- masculine on the outside but definitely submissive on the inside. 5'11 athletic build, short brown hair,(pic in avatar) 8 inches cut, served real time Mistress (Jennifer) on weekends.

Mistress Jennifer- 5'7 blonde, 34b breasts, incredibly toned legs, neatly trimmed pussy, strict but caring, playful personality and quite the imagination!

Dan- 6'1 curly blonde hair, skinnier build, 6 inches cut, was serving under Mistress Megan full time as her live in slave

Mistress Megan-5'9 brunette, 36c breasts, long tanned legs, shaved pussy, strong with a mean streak, friends with Mistress Jennifer since high school

That's all for the brief looks, attitudes, etc. Never met Dan or Mistress Megan before that day.

So now that the boring stuff is out of the way I will get onto the Slave Olympics in the next thread! A pretty creative all weekend event where the slaves completed a variety of events in order to prove who was the ultimate slave!

Slave Olympics Part 1
 

Mistress Jennifer had invited me over on friday at 5:00 and I was told to strip as soon as i entered her house which was customary for my visits. I was surprised to see another gorgeous Mistress in a sexy outfit and naked slave as I entered the living room.

" Kneel slave, and wait for instructions," said Miss Jen in her favorite red outfit and I complied without hesitation.

"I want to introduce you to Miss Megan and her slave Dan." Jenn stated. I crawled to Miss Megan and kissed her on each bare foot to show respect. "This weekend we will be holding the slave olympics where the best slave wins and will be rewarded while the loser suffers a fate that was carefully arranged by myself and Miss Megan.

I wasn't sure what to think at this point. I have known Mistress Jennifer and so far our sessions have been solo and definitely private. Now seeing another Mistress/slave couple and video cameras mounted around the room made me a bit anxious. I looked over at Dan and he was turning red as he kneeled in anticipation for what was coming. I don't consider myself bi-sexual but for some reason kneeling and waiting for instructions made my cock grow uncontrollably. I love to be naked but the thought of being naked in front of another Mistress and another naked slave made me extremely horny.

"First event: Face Sit/Ball Hit"
" This event begins with the opposite Mistress sitting with their bare pussy directly over the slaves face while the slave is restrained on his back. It is the slaves responsiblity to force 2 orgasms from the opposing Mistress with just his tongue. Additionally, every 30 seconds the Mistress will deliver a hard smack to the slaves exposed balls. First slave to provide two orgasms to their Mistress will win 1 point. Loser must give blow job to the winning slave and swallow his cum without spilling."

My jaw dropped as I heard the stipulation for this event. I have never sucked another man's cock before and was terrified at the thought of having to suck another slaves cock. I realized that this weekend I would need to bring my best in order to win! Also the thought of licking Mistress Megan's pussy made me extremely excited!

Miss Jenn pulled me aside before the event and told me she had 500 dollars on the line that I would win the olympics.......talk about pressure!!

Sounds good!
Can;t wait to hear more!

Slave Olympics- Part 2
 

The realization of what was happening hit me pretty hard as both Mistresses began to set-up for this event. Both myself and Dan were naked and kneeling as our Mistresses in their robes got the restraints and items ready.

Miss Megan grabbed me and brought me to my area and I was restrained on my back, legs spread wide and arms above head. We were set up so that during the event..the Mistresses would be facing eachother which both Mistresses really appreciated. Miss Megan gave me a quick smile as she was finishing up and bent down to whisper in my ear.

" I'm a very competitive person you little bitch so don't expect this to be easy! If you want to win you better have one hell of a tongue. Oh ya..by the way...we have a little surprise for you......"

Her voice trailed off and she stood back up and went over to the table. She grabbed something but I couldn't see what it was. When she returned, she had something behind her back but she began teasing me with her bare foot. Her red toenails began dancing on my cock which only added to the erection I had. She brought her toes to my mouth and I responded by offering my tongue.

" A little warm-up for that tongue of yours my little slut" she said.

While sucking on her toes, Miss Megan dropped her robe and I saw her naked for the first time. What a gorgeous body and incredible shaved pussy that I would be serving soon!! Then she abruptly knelt down and squeezed my balls in her hand. I saw the item she was hiding was a shoelace.....

"We decided that we should probably tie these little guys up, just so they are nice and tight while being easily exposed to us." "Go ahead Jenn," she motioned across to where Dan was tied. "Make sure you tie his nice and tight...make the little bitch scream!"

Miss Megan and Miss Jenn shared a laugh as Miss Megan knelt and swiftly tied my shaved balls without any problem. My balls have been tied before but this was definitely the tightest as I could already feel them turning purple and the event hadn't started yet. A digital timer was set-up that would automatically countdown from 30....buzz...and then repeat.

Miss Jenn stepped in front of us and I strained my neck to see my beautiful Mistress as she spoke, " Alright, we are about to begin. Remember the first slave to provide 2 orgasms for their Mistress will be declared the winner. Every time you hear the beep, the slave gets a nice smack on the balls with our wooden spoons. If the slave decides to quit, they will be deducted 1 point from their overall score and will be punished however their Mistress deems fit. Loser slave sucks off the winner and swallows every last drop of cum. Let the games begin"

She gave Miss Megan a quick kiss and then winked at me before making her way to Dan. I wonder if he was as nervous as I was for what was about to happen. Miss Megan returned with spoon in hand and grabbed the loose end of the string tied to my balls. She yanked it tight and I let out a yelp as she slowly lowered herself onto my face. Firmly enclosed between her thighs with her incredible pussy juices already beginning to drip on my face she gave the rope a tug, time started and my tongue sprang into action!

Slave Olympics- Part 3
 

I started off furiously with short tongue strokes in hopes of working Miss Megan into a rhythm and hopefully get her to "fuck my face' so to speak. I really didn't want to lose and have to suck a real cock for the first time so I told myself I was willing to do whatever it took to give Miss Megan two amazing orgasms. The first 30 seconds went by fast and I don't think I could have prepared myself for that first beep! I heard a faint beep and then I experienced a jolt of pain that made me instantly yell and my stomach felt ill. Miss Megan had pulled the string tied to my balls at the exact same time she perfectly impacted my balls with her wooden spoon. She shook a little and I could tell she was giggling at my expense.

"You enjoy that slaveboy? Better settle in for a long afternoon cause I'm just getting started!!" Miss Megan cackled and I honestly thought about throwing in the towel right there.

I continued my pace and really tried to focus on my oral training and to clear my mind. The next 10 minutes or so included some of the most intense pain I have ever felt in my life. Each 30 seconds felt like it was 10 seconds and Miss Megan was loving every minute of it. I lost track of how many minutes it had been but apparently smacking my balls every 30 seconds wasn't enough and my nipples became targets when between ball smacks. I knew Miss Megan was getting close as she started bucking and smacking me harder. I was getting deeper with my tongue and thankfully with a loud moan, I had given her the first orgasm!


At this point I have no idea what is going on with Dan and Miss Jenn and I am praying that she is holding out and I am in the lead. I didn’t think it was possible but Miss Megan became even more violent after the first orgasm. She had constant pressure on the string around my balls and she had taken a liking to punishing the tip of my cock and twisting my nipples. Miss Megan was definitely sensitive after her first orgasm and as a good slave I made sure to gently pleasure her toward another. I was pretty sure my balls were swollen and a fine purple color but luckily several minutes passed and I was greeted with the second massive orgasm….I have never been so relieved to have juices squirted on me in my life.

Mistress Megan delivered one final blow to my cock and rose from her position. I was incredibly sweaty and worn out from the event and literally laid there with my eyes closed….thankful that I had completed the task. Mistress Megan released my arms from over my head and I hoped to regain feeling in them before too long. She brought me some water and gave me a kiss.

“Good job little slave boy, hope you can forgive me for the beating. I can get a little feisty sometimes “

I thanked her and just hoped my cock would still work as I fed it to her slave. I finally had the energy to lift my head up and look across at Dan and Miss Jenn. Dan was still tied spread eagle but just like me his arms were free. His balls looked black and blue as well from what I could see. Mistress Jenn looked amazing as her tanned toned body stepped forward and made the announcement

“Well that was fun!! What a battle between two slutty slave boys who BOTH gave their Mistresses two incredible orgasms.”

My heart stopped as she spoke…both of us did it??? I had to have been the fastest!!!!!

“However, one slave completed this faster and the winner is…..

Is anyone enjoying this so far? I know I'm not the greatest writer and it's a little tough since it's from my perspective and I didn't really get to see Dan or anything happening around me in the first challenge. the next challenges i'll be able to give more details...

Hopefully you have liked it so far though!

wow I like it very nice job.....:) please continue

Whew...glad someone is enjoying it lol!!

I thought i was talking to myself for a while and wasn't sure if I should continue!:D

Slave Olympics- Part 4
 

I stole a glance over at Dan while he sat naked, legs still spread like mine, but at least we could sit up instead of craning our necks with hands tied above us. I wanted to see his reaction to the news that both of us had finished. The look on his face told me everything I needed to know and I realized I my fate right as Miss Jenn broke the news….

“The winner of the first event was DAN! He completed the task one full minute prior to Justin and therefore has been awarded 1 point. I must say the way you were beating my slaveboy was the reason I squirted so fast the 2nd time Meg….you bitch ;)”

“Mmm thanks hun!” replied Miss Megan. “I was trying to get him to quit so I could really have some fun with him but it was a win-win! My slave won plus I got two incredible orgasms hehe” Now is the real action where Justin gets himself a nice cock to suck”

Right as that sentence left her lips I saw Dan flash the biggest smile as he realized he would be getting the reward. I on the other hand was not amused knowing that I would be sucking my first real cock. Miss Jenn has invaded my mouth and ass with a strapon but I had never been used by a man during my training. It became more humiliating considering I was about to be fed the cock of another slave. My balls were finally beginning to regain feeling in them which was definitely a glass half full moment.

Mistress Jenn strutted over to Dan and released his feet from their bindings and he was set free.

“Great work slave boy….you have earned it! Take a few minutes to let the blood rush back to your limbs while we get your cockwhore set up for you”

She then reached over with her gorgeous size 7 foot and tapped his cock with her neatly pedicured toes.

“Make sure this cock of yours gets some blood to it too, we expect a great show”

Miss Megan joined to congratulate Dan on his first point and my Mistress walked over to my still spread eagle naked body. I was sitting up and stretching my arms trying to regain some feeling when she pushed me on my back with her foot and pounced on my chest. I could tell she was really enjoying herself and it made me happy even though I had lost the first challenge.

“Are you okay little slut? I must say you did pretty good and I am very pleased with you. Now you are going to suck some cock like a good bitch…and remember if you spill a drop of cum the beating that Meg gave you will be nothing compared to what I have in store for you.”

She laughed as she stuck her big toe in my mouth and ordered me to suck it. I licked it clean and kept sucking until she was satisfied and she called Miss Megan over.

"Let’s get him ready for his cock sucking debut…what did you have in mind for how he should be tied and displayed for this performance Meg?”

Miss Megan grinned and responded with a simple phrase, “ Oh, I think I have something in mind”


---I guess nows a good time for some fan involvement...How do you think I was tied or positioned to suck Dan's cock?

i have to say i usualy dont like reading about male slave stories but i really like this one so keep it up

Amazing story please keep it up is it real?
P

Slave Olympics- Part 5
 

Thanks for the few responses guys!

Glad you have enjoyed so far and yes these events really did happen to me. Some of the conversations/dialouge might not be spot on but I have a pretty vivid memory of this weekend so it is relatively accurate.

Enjoy!

I found myself on the bed with my hands tied firmly to the outside of my knees with my legs raised and ass propped on a pillow. My head was positioned so it hung over the edge of the bed and I knew I was not going to enjoy what was about to happen. The question about why my ass was exposed when my mouth was supposed to be the hole that was being fucked was answered as Miss Jenn entered the room holding a butt plug.

“This should plug his other hole while he is entertaining us as a cocksucker, wouldn’t be a true slut without something up his ass right Meg?”

“My thoughts exactly babe" responded Miss Megan. "Let him lube it up with his mouth so we can get a preview before we bring Dan in to receive his reward.”


As Miss Jenn walked over to me and told me to open wide I actually kind of appreciated the opportunity to get used to my head being upside down and hanging off the bed. It also was a nice consolation that both Mistresses remained naked and they didn’t seem to have any intention of putting clothes back on! She told me to make sure I get the plug nice and wet as it will be the only lube I get before it goes in my ass. Miss Megan made sure to get the video camera nice and close to my face as I went to town on the plug. I felt ridiculous but knew that a raw object going into my ass without lube wasn’t ideal.

“Alright, times up” announced Miss Jenn. “Bring Dan in and let’s get this show going. She grabbed the plug from my mouth and went to the other side of the bed and inserted it in my exposed ass and there was nothing gentle about it. My legs were already pretty tired as I didn’t have much choice to raise them up with my hands tied to them but I had a feeling my sore limbs would be the least of my worries.

Dan entered the room and immediately saw me in my current predicament and it looked like his cock grew to its’ full potential. Miss Megan followed and smacked him on the ass as if to say ‘he’s all yours’. Dan approached with a cheesy grin on his face and with his height it conveniently put his cock in my direct line of vision. He slapped me in the face with his rock hard cock and worked the tip onto my lips as Miss Jenn held the video camera close to get all the action.

“Wait!” shouted Miss Megan. “Here are the rules, Dan you will get 15 minutes to fuck that hole and cum as many times as you wish. If at any moment, it looks like you are not giving us your best effort you will be done. I know you haven’t been allowed to cum in over 2 weeks so I’m sure those balls are filled with plenty of yummy cum! Just remember this isn’t a lovely blowjob from a nice girlfriend…you are to fuck his throat and make that bitch gag!! Your time starts now!”

Dan seemed to be inspired by the pep talk he just received and I immediately was hit in the face with his cock and he ordered me to open up. I opened my lips and took my first real cock into my mouth. He wasted no time thrusting his 7 inch cock deep into my throat. I found out quickly why my Mistress chose this position. With my head hanging over the bed it provided a great angle for Dan to literally ram the length of his shaft down my throat. His balls repeatedly began to hit me in the nose/eyes and I thought I was going to pass out. Mistress has worked with me on my cock sucking skills but I had tears in my eyes as my gag reflex was tested early and often. He started off slow making sure he got his full length into my throat and then back to my lips. He began to pick up the pace due to some encouragement from our Mistresses and reached to grab the tops of my feet so he could really go at my mouth and maintain his balance.


The girls were loving the action and were playing with themselves watching my mouth being raped in front of them. Dan had a great view of the girls and I could feel the intensity pick up as he was getting close to orgasm. He thrusted a little harder and I could feel him start to tense as I tried to prepare myself for the imminent explosion. One final thrust and the back of my throat was hit with an intense amount of cum. This was a new experience for me and I literally thought cum was about to flow out of my nose and I almost puked. It took everything I had to not spill as Dan spasm’d at least 3 times with copious amounts of cum deep into my mouth. The girls wildly applauded as Dan pulled his cock from my mouth and almost fell backwards due to exhaustion.

“Bravo!” yelled Miss Jenn from the head of the bed with camera in one hand and 2 fingers from her other hand deep inside her now dripping wet pussy. My first cock sucking felt like it was straight from a porn movie. The plug in my ass and my still rock hard cock reminded me how slutty I must have looked throughout the entire ordeal. Miss Megan told Dan he had achieved orgasm in just over 7 minutes and could have another go if he could rally. She then quickly excused herself and said she had to go get something real quick. Dan sat down in a chair with the hopes of being able to fuck my mouth again.

Miss Jenn lowered the camera for a second and helped me into the middle of the bed and flipped me over so I was on my knees facing her. She spread her legs wide and nodded which was the order to service her. I bowed my head and greedily lapped at her pussy. She recovered the camera and began filming again.

I was into a great rhythm and had Mistress close to the edge when all of a sudden I felt the bed compress behind me and the plug being removed from my ass with a loud POP. I had no time to react as Miss Jenn pushed my head further into her pussy and I felt two hands on my back and a strapon cock enter my ass.:eek::eek:

damn this is so hot....that must have been some weekend thanks for sharing it....:)

thanks! It was a great weekend and there is plenty more to come since my story is still on friday night


kinda sad there aren't many comments but ohs well :(

dont beat yourself up over comments its still a great story this is on i am following till the end

More please:P love it.

out of town until tomorrow

will write at least one long part tomorrow

possibly two

Slave Olympics
 

I could faintly hear Miss Megan’s voice behind me as she began thrusting her 9 inch strapon into my gaping ass. She grabbed the ropes that were holding my hands to the outside of my knees and began pumping my ass at an incredibly fast pace. I felt like the strapon was entering my guts as Miss Megan made sure to go as deep as possible but I tried hard to focus on the pussy that my face was buried in. Miss Jenn was bucking her hips as my face was being pushed forward and she developed a rhythm that matched Miss Megan’s perfectly. It only took minutes before Miss Jenn let out a loud moan and squirted on my face as she pushed my head down and she lost control of her body.

“MMMMMMM Fuck his ass babe!! Give it to him deep and hard!! Dan, get over here now!” yelled Miss Jenn.

Not surprisingly Dan was able to get rock hard again watching the events unfold before him. I was turned 90 degrees on the bed and Dan’s cock was again staring me in the face.

“Fuck his face while your Mistress takes him from behind slave” yelled Miss Megan as she slapped me on the ass.

Dan inserted his cock into my awaiting mouth and again I felt the uncomfortable feeling of my throat being raped. I felt like I was going to pass out as my ass was being fucked raw and now my throat was stuffed with cock. Miss Jenn recovered quickly from her orgasm and snuck her feet under me and was teasing my rock hard and sensitive cock between her toes. It had been over 2 weeks since I was last allowed to cum and I became extremely excited that my cock was finally getting some attention! Dan began thrusting faster which encouraged Miss Megan to continue her rapid pace as her thighs rammed into my ass cheeks with each deep penetration. Miss Jenn continued stroking my cock with her toes and would tease the tip as my pre-cum was leaking. I could feel myself becoming very close and unfortunately could not ask permission to cum as my mouth was full at the moment. Dan began to moan and tense up and I knew he was about to blow. I prepared myself for my second serving of cum and also for my own explosion. Miss Jenn sensed I was close as well and withdrew her feet from my cock just as I was close to euphoria. My cock twitched in search for her beautiful feet to carry me over the edge as Dan unloaded his warm seed into my mouth.


Miss Megan pulled out of my ass just as Dan came and raised her arms in the air in victory!

“Amazing!!!!!, thanks for the great ride! What a hot ass you have little slave!”

My mind was racing as my cock needed to erupt and was longing to be touched. Miss Jenn smiled at me and said, “Sorry slut, not today”. She began to untie me and gave me a soft kiss on the lips as I fell backwards onto my back in exhaustion with my cock still at attention. Miss Megan reached with her big toe and scraped up some leftover precum that was glistening on my cock.

“Here you go boy, don’t want this to go to waste” she said with a smile as I took her toe in my mouth and sucked it clean.

“A great opening day to our events, slaves!” announced Miss Jenn. “That will end tonight’s festivities so we can relax and prepare for tomorrow. First event in the morning will test your anal capabilities in an event we like to call “Save a horse, ride some dildos”


After the announcement, we had some dinner and enjoyed each other’s company while relaxing after an exhausting yet incredibly fun day!
I went to bed determined to redeem myself after suffering the humiliation of my first cock sucking experience. I wanted to prove that I was the best slave and wanted to wipe the smirk off of Dan's face in a big way.

Great story, keep it cumming :)

I do have some pics/videos from that weekend....still deciding on maybe some type of challenge or contest for people to get the chance to see them if interested....:p

any ideas feel free to comment or pm me :D

I would love to see some pics

great story boi, keep writing

wow awsome Im loving it....

next part coming soon....details first event of Saturday. "Save a Horse, Ride some Dildos"

I'm impressed by how much you remember!

yeah...like I said previously...some of the dialouge is not verbatim but it is close.....the events i remember vividly because I still daydream and remind myself about the fun that was had that weekend...

Finishing up next part and posting on my break at work!

Slave Olympics
 

I woke up next to my beautiful Mistress Jenn and felt blessed to be able to have such a good relationship with her. We can talk for hours about life, sports, etc and she can be fucking me in the ass the next minute without any issue. Miss Jenn had her hand on my abs and moved slowly up to twist my nipples.

“Suck my toes slave” she whispered. “Then work your way up to my warm pussy.”

Mistress loved to have her toes sucked and I enjoyed worshipping them. I spent the next several minutes covering every inch of her feet with my tongue and then working my way up to her quivering pussy. I swirled my tongue and used my fingers to slowly and passionately work Miss Jenn into a toe curling orgasm. She laid back exhausted and sweaty as she ordered me to begin making breakfast while she showered and got ready for the first event.

Dan and myself talked for a little bit as we both made breakfast stark naked for our Mistresses. Dan was still acting a little cocky after face fucking me yesterday and it irritated me a bit. I was definitely hoping to turn the tables and win the next competition! The girls joined us for breakfast in their booty shorts and tank tops. I was hoping they would spend the weekend naked like Dan and I but they both looked beautiful regardless. Both Miss Jenn and Miss Megan excused themselves from the table and told us to do the dishes while they set up for the morning event. Miss Jenn gave me a kiss on the cheek and said, “You better win this one babe….or you’ll be sorry” I got goosebumps as she said it and I believed that if I lost…I would indeed be very sorry!

My cock was already beginning to get hard as we waited for the event to be set up. I tried to guess what it would involve and I was pretty confident in my anal abilities because Miss Jenn loved to strapon fuck me on a regular basis. Dan seemed a bit nervous when I asked him if he’s been fucked before and he said he was still pretty tight but Miss Megan was never gentle on his ass and that he can take a good fucking.

We were summoned into the spacious living area and I was shocked by what I saw…….

another really hot chapter leaves me hanging Im really excited for the next one.....

Trying to get another chapter written tonight!

I will say nothing motivates me more than getting PMs or comments from people enjoying the story...jus sayin...lol

Keep writing. It's really good.

Slave Olympics
 

We walked in and saw both Miss Jenn and Miss Megan topless with thick 8 inch strapons secured to their waists and big smiles on their faces. Just seeing that would have made me nervous but my focus was directed at the 2 rows of 4 chairs where each chair had a suction cupped dildo attached to it. My mind was racing trying to decipher what was going on.

Miss Jenn’s voice broke the trance I was in and all of my questions were soon answered.

“I can tell by your faces that you are curious about your next challenge. I will give you the rules of the event once and only once. If you break the rules during competition you will be punished and also lose a point. You will see two identical "dildo riding courses" with 4 chairs each set up. You will start at chair number 1 and work your way up to chair 4. You also may have noticed that each chair has a nice dildo attached to it. :D

Here are the measurements
Chair One: 4.5 inches Length/ 1.5 inches thick
Chair Two- 6 inches/2 inches thick
Chair Three-Adam and Eve Triple Header Cock- 6.5 Inches/2 inches thick
Chair Four-- 7 inches/ 2.5 inches thick

“You are required to take the entirety of the dildo at each chair before moving on. You must sit on the dildo with it fully inside of your pretty little assholes for 30 seconds in order to be allowed to move on. Miss Megan and I will provide lube to your ass prior to the beginning but you are responsible for the wetness on the dildos. No actual lube is allowed!!! :eek: Meg, tell them what happens after they have finished the 4th chair” Miss Jenn said with a laugh.

“Thanks babe” replied Miss Megan as she came closer and grabbed hold of Dan’s throbbing hard cock. “After you bitch boys finish the chairs, you will have one final challenge in order to be declared the winner. You will then crawl to your Mistress and suck her strapon cock until you can take the entire shaft in your mouth for 5 seconds. Then your Mistress will fuck your ass and you will be stroked until you cum. First slave to cum and lick all of their cum up will be declared the winner!! If you lose, your ass will belong to the winning slave for an award winning fucking”:eek:

“Any questions little sluts?” Miss Jenn asked while gripping her strapon with a huge smile on her face

Loving the story its an amazing thing you guys have I hope your relationship stays strong. Cant wait for the next part hehe.

ohhh my god!!! this just keeps getting better!!!!! I am so excited for the next part :) you are a wonderful writer!!! my fingers are crossed that that smug pig loses :). Well Done :) xx

Slave Olympics
 

Trying to process everything was a chore in itself as I sat kneeling with my cock standing at attention. Hearing that the loser would be assfucked by the winner was all the motivation I needed to bring my best effort to this challenge. I was already irritated that Dan beat me in the previous event and equally annoyed that he stated several times that he was the “alpha slave”. I felt bad for Miss Jenn because I want her to be proud of me and I had failed so far. Strategies were swirling in my mind as I tried to figure out the best way to tackle this challenge in order to beat Dan and even the score.

Miss Jenn and Miss Megan announced that we were about to start and ordered us to the starting line. Miss Jenn brought some lube over and gently inserted two fingers in my asshole. I appreciated her “warming me up” and providing the only lube I was allowed. When she finished, she gave me a kiss on the cheek and whispered in my ear,

“You can do it, just relax your ass and slide down. He ain’t got shit on you!”


With that, she retreated to the side with a stopwatch in hand ready to time the first chair. She knew of my sports background and had a special way of motivating me. Just seeing her incredible body with a strapon dangling from her shapely hips made me want to win for her even more. I didn’t need to hear anything else and was ready to kick Dan’s ass!


Miss Megan gave the countdown and I envisioned myself at the finish line. When she hit 0 I wasted no time getting to the first chair and getting down to business. My ass was still fairly sore from the strapon fucking I received the day before but it also might have been helpful in a way. I grabbed the dildo and positioned myself over it and slowly inserted it into my asshole. I wanted to make sure my legs were wide so my ass would be easier to invade. I have trained with this dildo before and I was confident I could take the 4.5 inches once I got it in. I slowly squatted down and tried to breathe and relax. I could feel the dildo sliding in and then my ass hit the chair and Miss Jenn started the 30 seconds. This is where one of my pregame strategies came into effect. I grabbed my rock hard cock and started stroking at a feverish pace. I figured if I stayed close to edge while on the dildos then I would be quick to cum when Mistress was inside me. The 30 seconds seem to go fast and when Miss Jenn announced time…I had a slight lead over Dan who was still sitting on his first cock.

As I moved to chair 2, I quickly got into position to glide down on the second cock. My ass was still relatively lubed so I wasn’t concerned with getting it in but the extra two inches definitely made it more difficult. I inserted the tip and slowly began riding the dildo, squatting up and down slowly working it further into my ass with each squat. I could feel my stomach starting to ache and the pain was beginning to intensify. I continued to ride it and try to wiggle down and then sat down the final inch which immediately sent tingles up my spine. The time started and I again started jacking my 8 inch cock that was now glistening with pre-cum. I glanced over at Dan and realized he was also fully impaled on the dildo and I knew we were basically in a dead heat. He had not touched his cock and I’m hoping my strategy works out in my favor! I heard Miss Megan release Dan and saw I was seconds behind him. Miss Jenn counted down and within seconds I was off as well.

I got in place for the third dildo and inserted the first head into the entrance of my asshole. I felt the first ridge hit my prostate and without warning……..:confused::confused::eek:

wow amazing story! :DDD

liking it so far everyone?

Loving it :D Keep the chapters cumming...

hot I love the updates......I wish I had been there for that....:)

Slave Olympics
 

My cock violently twitched and I immediately tried to cut it off so I did not cum and become disqualified. I tingled from my spine to my toes and barely avoided shooting my hot cum all over. I realized that maybe being so close to edge was not the best strategy. Miss Jenn was yelling at me to get control of my cock and that she was going to beat the shit out of me if I came without permission. I regained control and knew that I had lost about a minute squatting on the first ridge. I prepared myself for another sharp tingling as I lowered myself past the second ridge. It contacted my prostate and I moaned with pleasure as more precum started oozing from my cockhead. My ass was beginning to feel ripped inside as the lack of lube was taking its toll. My stomach muscles tightened and I tried to relax so I could push past the final ridge and engulf the dildo in my ass. I widened my legs and tried to maintain my balance as a sat down on the final 3 inches of the dildo as my ass smacked against the chair. Pain immediately shot through my body as the dry fucking ripped my insides. Miss Jenn started the countdown and I looked over and saw that Dan had just finished the triple header and had moved on to the 4th dildo.


Now that the dildo was in, I still wanted to make sure my cock was ready to cum so I could make up time on Dan as he was not on edge. When my time was up I quickly dismounted the dildo and got to my knees in front of the 4th chair. I took the final dildo in my mouth and began sucking it with all my strength. I couldn’t take another dry fucking, especially with the largest dildo sitting before me. I gathered up a good amount of spit and lubricated the dildo like a good little slut. Miss Jenn was egging me on from the sidelines which made me even hungrier. Looking back at the video, I definitely looked a little too eager deepthroating this dildo but that’s the competitor in me. Dan had not lubed it up and I could tell he was struggling to sit on it as I could hear him wailing in pain. I saw my opportunity and mounted the dildo as I began to squat and the now wet cockhead entered my asshole. I have taken a dildo this size before but it’s a little different when your Mistress is behind you and fucking you without mercy. I decided to begin by riding it and trying to go an inch or so lower with each squat. This plan seemed to work for the first 5 inches or so.

“Get your ass down on that dildo NOW” Miss Jenn screamed at me. “You can ride my dildo later you stupid slut…slam your ass to the chair!”

With that encouragement I plunged onto the final 3 inches and my ass made a loud SMACK onto the chair. The pain was excruciating as I tried to black out everything around me and not focus on the incredible pain in my stomach and ass. The 30 seconds felt like they were going on forever. My ass needed a break and finally when Miss Jenn called time I was free from the chair. I looked over and noticed Dan still had a few inches remaining and was receiving quite the verbal abuse from Miss Meg so I knew he would be done soon.


I crawled to Miss Jenn who was waiting with strapon in her hand.

“Deepthroat me bitch, stroke your cock while you suck me but don’t you dare cum! Hands go behind your back when you feel like you’re going to cum”

With that she grabbed my head and forced me onto her waiting 8 inch cock.
I tried to relax my throat and get the full cock in for the required 5 seconds so I could move on to the final part. Once the cock made contact with my throat, my gag reflex was so intense that I almost puked. My eyes began to water and Mistress pulled out and slapped me on the face.

“Get your shit together or you are gonna get fucked by Dan….ALL NIGHT LONG! Look, he’s already sucking cock just like you are!”

I looked over and sure enough he was kneeling in front of Miss Megan and she was forcefully raping his mouth. I was determined not to lose and opened my mouth, ready to be face fucked and began jacking my rock hard cock. Miss Jenn entered my mouth slower this time and eased it back and forth. I was making great progress and my cock was ready to blow as I put my hands behind my back, Mistress kicked me with her barefoot in the balls as she thrusted the rest of her cock into my mouth. She started timing and my face turned bright red as I lost all oxygen. I could feel myself getting lightheaded and luckily the 5 seconds passed and she pulled the cock out fast as I coughed and sputtered to catch my breath.

I caught my breath as Mistress asked me what position I wanted to be fucked in. I looked over at Dan and he had finished his task and was being fucked by Miss Megan doggy style with Miss Megan reaching around to stroke him. I knew I didn’t have much time and immediately lay on my back with my legs up so Mistress would have easy access to my already dripping cock. She grabbed my ankles and easily inserted her strapon into my now quite loose boy pussy. She grabbed my cock and started thrusting inside me as she furiously began fast long strokes up my shaft. I laid back and took her pounding while watching her beautiful tits bounce up and down and knew that I was going to cum soon.


Mistress continued to pound my ass as my abs started to clench and at that moment I heard a loud moan coming from the other side of the room…….

Can't wait for the next chapter! I wish they were coming faster.