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The Cum Hole Contest


rduckv

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I have lived a very fortunate life. I came into enough money to live more than comfortably and decided I wanted to live in a fantasy so to speak. So I moved to a new town, got a big place, and got me a few house boys. I knew what kind I wanted, or at least I thought I did. After many interviews I found 3 that were very much to my liking. Luke is a short built blonde firecracker. He’s got a great laugh and a seriously kinky side. He loves to cook so he’s the butler, cook, and personal trainer. Next was Gabe. I usually don’t like the younger thinner set but he was too sweet and willing to do ANYTHING for the job and for me so I took him on as the cleaning boy. Finally there is Jake. Jake surprised me, I usually don’t find guys taller than me attractive and me being 6’2” I don’t run into them a lot anyway. But Jake is 6’4” and has the shoulders and chest of a god so he was hired. He is my gardener, driver, and mechanic. Each is special in my eye in a different way. I can’t forget the first time I bred each one of them. But those are stories for another day.

Today I wanted to write about our latest contest I had with them. First you have to understand I LOVE cum, anyway I can get it, the feel, the taste, just everything about it. I knew it was going to be a rough week at work so I designed a contest for them. I gave them one weekend, from fri night till sun morning to bring me the best hole they could. I didn’t care who fucked them or how many. Whoever brought me the best cum sloppy, sweet tasting, warm, worn hole the way they all know I like it, would win. I promised the winner a good bonus and a small trip just the two of us and sent them on their way. I knew each of them had at least one fuck buddy besides me but wasn’t sure how far they would go. I just knew I love sloppy seconds and was hoping they would surprise me. And they did. I swear I didn’t see much of any of them that weekend. Fri night I had a work dinner and came home and no one was there. I later got a text asking me to join them at a club we sometimes go to. I decided to stay in though. Each of the boys has a room that has access into the house and to the outside so they can come and go as they please. I had a few drinks and went to bed. I figured if any wanted a judging that night they would wake me up. The next morning I woke up and started toward the kitchen. That’s when I heard Gabe getting plowed upstairs, and noticed Luke was walking like he was freshly fucked making breakfast. He always looks hot in the morning, he was standing there in a red tank top showing off all the definition of his chest and arms. I could just make out those rosy nipples that taste so good. The cotton gray pajama pants that hung over his ass just reminded me of those sweet globes and that perfect winking hole I have seen, kissed, and felt the inside of so many times. I asked him “How are you doing this morning? You’re looking a little bow legged.”

“I’m fine, just trying to keep it ready for ya.”

“Oh, is it ready to be judged?” I said as I felt myself harden in my pants so excited at the idea.

“Not yet.  I have two more who are supposed to be stopping by this morning.  Maybe then you can judge it” Luke said

I groaned and rubbed myself.

Smiling, he laughed and asked “Would you like a taste, just a preview?”

“You know I would.”

“Promise it won’t influence your vote?  We all promised to play fair on this one and don’t want to be caught cheating,” asked with a smirk.

I raised my hand like a boy scout and said “I promise if one of their holes is better I will choose them. Now can I have a taste?”

He stuck his hand that wasn’t holding the spatula for the eggs and bacon into his pajama pants for a moment and it came back glistening. Looking like snail slime all over his middle finger. He put it to my mouth. I kept my lips closed for a min so I could smell his ass juice and cum on the finger. I tasted it like it was a fine delicacy. It was sweet and tangy.  My mouth followed his finger as he attempted to withdraw himself from my mouth.  In fact, I was off my stool and grabbed his waist to prevent his departure.  Not to be outdone, before he could stop me.  He pushed us together so I couldn’t get his pants down, turned his head and kissed me. Then said “You are always welcome to my hole, you know that, but you have a contest going on and that wouldn’t be fair”

I acquiesced and returned to the breakfast bar to await my breakfast. At that moment I heard Gabe’s infamous howl meaning he had been jizzed in and set over the edge himself. We both laughed.

“Well he seems to be in the spirit of it” Luke said

“Of course. Are you worried?”

“Not really, I know I am your ideal type, as long as I can get a lot of good cum in my hole I’ll win”

“Oh a bit cocky are we? Don’t rest on your laurels. You always have to watch out for the underdog”

“I’m not being cocky, just confident, besides I have an ace up my sleeve I’m not sharing”

“How exciting. Have we seen or heard from Jake yet?”

“We all went to the club together last night. We kind of split up as the night wore on. I think he may have gone to the bathhouse.”

“You have an ace to beat bathhouse used hole?” I laughed

“We’ll just have to see won’t we, besides I’m not sure that is where he went, and you know a guy his size is always being begged to be the top in the bathhouse.”

“Well he is good at that too.”

“Hey, I am too but that’s not the contest. Don’t go changing the rules now.”

“No worries about that. I’m looking far to forward to 3 sloppy, tasty holes far too much.”

“Good, because I’m making you more than breakfast lol” Luke said as he slide the food in front of me and wiggled his ass at me. “Now if you don’t mind, I have some more mixing and batter making to do before my dish is ready to be served.” And with that off he walked, still with just a bit of the stagger of being freshly fucked. It took everything I had not to tackle him and take that ass. I know what that ass feels like, and how much sweeter it is cum filled. However I resisted. I sat there eating my breakfast hard as a steel girder. When I had finished my omelet I heard Gabe bounding down the stairs to his room. He was wearing a pair of running shorts and no shirt. His body is always a little distracting, He’s got the forever tan Latino beautiful skin. He has the most delicious brown nipples that beg to be tortured and oh how does he love it.

“Good morning, David”, Gabe said.

“Good morning, boy. Is your friend gone?”

Gabe blushed and said “Yes, I sent him on his way, he had donated to my cause and I was through with him. “

“Your vacation cause?” I said laughing

“Yes, I don’t want to be left behind” He said sheepishly

“You do know we are coming back” I said giggling

“Oh I do, but to have to do without you and your cock would make me so sad” he says as he grabs my cock through my pajama pants. “So has either of the other boys turned in their homework yet?”

“No, I think they are both still working on it.”

“Is there any extra credit if I turn it in early?”

“Not neccesarly”

“But it’s not gonna hurt me to turn it in early” he says as he bends over the counter next to me.

“No, it might help your cause seeing as your brother was in here turning me on making me breakfast, I could really use the chance to get off.”

“Good cause the fresh load I have in my ass is begging to be worked in.”He says as he pulls down his shorts. “I even added my own loads to the hole.”

I stood and walked over to him, savoring the sight of his round ass. It is almost hairless expect for the crack. As I got closer I felt myself smiling seeing the cleft of his ass sitting there, begging for it. “So how long have you been working on this hole?” I asked as a felt the globes of his ass.

“All night sir, I wanted to get it as full and sloppy as possible for you, I was going to go even longer but I’ve come upon a dry spell this morning and wanted to get it to you while it was fresh.”

“Well you do know how I like it Gabe” As I parted his cheeks I saw just a hint of shine at the top of his crack. I started to follow it down with my eyes, noticing the mix of cum, sweat, saliva, and ass juice blended together in his crack, covered with the finest of hairs. I was hard as a rock. It took everything I had not to just drive home in one swift motion. But I remembered I was supposed to be judging this and wanted to get all the aspects of this fine specimen. I leaned forward and sniffed it and felt a drop of precum leak out of myself. Running my tongue down around his ass he started to squirm. As I got closer and closer the taste got stronger and stronger. I finally made it to his winking hole and felt the heat coming off his fresh fucked hole. I dove in. He kept squeezing his hole to make sure to keep it in but was moaning so loud from my tongue assault. I am humming in his ass eating his ass like I am a ravenous animal given his favorite dish. Licking, tonguing, chewing, and sucking on that hole for all I was worth, but I could only get a little cum out, he was a skilled boy keeping it in there. Finally I couldn’t take it any longer and stood up to drive my meat into that perfect hole. As I stood up Gabe asked me “So how was the taste?” I laughed a bit.

“You want judged on the different parts?”

“I like to know how I am doing.”

“I give it a 7. Perfect taste, Nice and fresh”

“Why only a 7?” He says as he is wiggling his ass on my cock.

“Because though I can tell that the hole is cum filled, I can always have more cum” As I am thrusting in his crack. Feeling my dick rub his hole over and over. He keeps trying to get it in but I am enjoying his slimed crack.

“Come on daddy, my hole feels great and it needs you in it.” At that I knew I was going in on the next stroke, and I did, all the way to the hilt in one stroke. He cried out nice and loud just like I like. I left it in at full dept and felt his hole squirm and stretch as it adjusted to yet another cock in the warm cum cavern. I heard the front door open as he screamed, and then proceeded to thank me and my cock. I saw jake walk in, he looked rough, he was a little dirty and his clothes looked worn. He smiled at me and winked as I was balls deep in Gabe.

“I’ll get to you next, Jake.”

“Oh I’m not ready yet, Sir”

“Sir?”

“It’s been a long night of service to get ready for you. But I am not done yet.”

“Got it, your brother wanted extra credit for turning in early.”

“Did he get some?”

“No extra credit, but he is defiantly fresh and going to get it good” at which point Gabe couldn’t handle it any longer and started trying to move all over my cock. But with his jammed between me buried deep and the counter he couldn’t do much but milk my cock in his ass, moan, and groan. Jake laughed and turned to walk away and I noticed his jeans had a hole ripped in the ass and his pants were soaked around that hole. Between Gabe squirming on my cock and the sight of that I felt my dick get even more ridged. I almost blew right there but I knew I wasn’t done. I gave his hole 5 good deep slams and pulled out and dove for that hole before it all leaked out. And was I ever rewareded. I got my face planted in his ass just in time to catch cum running leaking out of his hole. Swallowing and sucking I gathered all the cum I could from that hole. He just kept up his growling and started his pleading to be breed. I stood up and drove back in. I knew I wasn’t going to last long. I was way too turned on but was determined to give him a good ride and did. I started thrusting on him and he just got dirty in his talk. He was begging for cum, calling me every name in the book.

“My cum channel needs you daddy. Make me yours, load me up. You own this hole no claim it. I wanna feel your morning load coating my ass. I wanna keep it in me forever. Own my ass, tear it up so no one else can use it but you. Deeper, harder, just own it.” After all that talk spewing out of his mouth I just started smacking his ass to feel that muscle squeeze me tight. And when I was finally close enough I bent over his back and grabbed his nips. He needed pain and I needed to feel his ass get as tight as possible. I pinched hard. I tried to rip those bastards off and felt his ass tighten up from the pain just causing him more pain. He cried out. He went rigid which sent me over the edge. I kept thrusting right past his protesting ass and enjoyed the ride. He was screaming in a mix of pain and pleasure. That was it I grunted load and dumped a load in my little houseboy. It felt like it went on for ever. I just kept shooting steam after stream of cum into his ass. And I hadn’t let go of his nips. I had held on for dear life as I jizzed his hole. He let out a scream. This boy always has had jizzjoy. That was that I thought.

“Did you jizz the counter Gabe?” I said as I released his nips. He sighed.

“No sir, I know better.”

“Good boy, damn nice hole” I said as I slipped out of his hole

“Thanks Daddy.”

“Now get me a sharpie” I smacked his ass to tighten the hole “And keep that cum in” He reached over the counter and produced a sharpie out of the drawer there. I took the black marker and wrote an 8 on his ass.

“Of course, nothing makes me happier. How did I do?”

“You did great as always and I scored your hole too”

“And?”

“I wrote it on there at the time of deposit so as not to be skewed. If you wanna find out what it is find a mirror” I said laughing. “Oh and no pants till tomorrow morning and only a jockstrap if you need underwear. I’m going to want to taste that ass later again.”

“Got it, Thanks”

To be continued

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  • 9 months later...

Part 2

 

“But no sitting on the good furniture.”

“Rim chair or hard wood floors only huh?”

“You know the drill boy”

His smile said all I needed to know.  No matter which boy I took with me the other two would have fun without me and be happily waiting here when I get back, bent over the counter if I wanted.  He started to walk away before I cleared my throat.  He turned around.  I stood there looking at him.

“Oh sorry, daddy.  I got too excited about my score.” He said as he got down on his knees and cleaned off my cock with his mouth.

“Good boy”

I heard a door close down the hall and knew one of the boys was increasing their load count and hole stretching.   I decided to take a shower and get ready for the day.  I had a few things I wanted to go out get for my trip.  While I was in there Gabe came in to see if I needed company.  I told him no, I wanted his hole to stay the cummy mess it was and if he did shower I would downgrade his score.  He pouted and left.  Then Luke came in to see if I wanted company.  I told him only if he was turning in his ass for judging.  He told me no, he was still waiting on a few more scheduled deliveries.  He did tempt me more though by rubbing his ass on the glass of the shower.  It was a red hot, slimy mess.  It looked delicious in that ass crack of small blonde hairs.  I told him if he didn’t stop I would take his ass and it would be judged now.  He left after that.  Of course I couldn’t resist licking the glass.  His ass juice mixed with all that cum sent a shudder through my body.  He is the biggest tease but unlike the usual tease he will do anything I tell him to or even things I want before I tell him.  I kept waiting for Jake to walk in.  All the boys know I love playing in the shower and I almost always have at least one of them in there with me.  But Jake never came in.  I got out and toweled off.  I then went down stairs to read the paper.  I was going to take one of the boys to the store with me but they were all occupied or indecent to take out at that point.  As I was reading two big black men walked out of jakes room.  My jaw dropped.  They were both naked.  They were both at least 6’6” and hung.  The one on the left was hanging longer, but the one on the right was very thick.  They both were still semi hard. 

The one on the right asked “Are you David?”

I said “Yes”

They handed me a card and an unopened rose.

The one on the left said “And he said something about a shower boy?”

I hollered for Gabe.  He came down from his room. I said “Your brother said you were a shower boy for these guys.  So clean their dicks, then grab their clothes, and then take them to the shower.”

Gabe had the biggest shit eating grin and said “Yes sir.”

As Gabe got down to clean their dicks I told the guys “Think of him as a guest towel.  He is pretty, he is there to be used, but down ruin it because you are a guest.”  They both nodded.  I then turned to my card and rose.  I opened the card.  It said “My ass is no longer just a rose bud.  These boys have added their spunk as the final ingredient for your feast to enjoy.  I wanted you to see what just destroyed my hole.  I now await your judging of my hole.”  My cock leapt to attention.  Gabe was getting to much into giving head and not just cleaning.  I smacked his ass.  He spit out the thick cock in his mouth.  I grabbed his nipples and stood him up by them.  I then grabbed his balls so I had his full attention.  “What was your second direction?”

He looked at the ground and said, “Gather their clothes.”

“Then go, Sorry boys.  If you want there is a gang shower in the bathroom down at the end of this hall.”

As Gabe came back from Jakes room I told him to stop.  He wouldn’t look me in the eye.  All I said to him was cage.  I then went to Jakes room.  When I walked in it smelled like sex.  First thing I noticed was he had left his pants on but he was restrained wrist and ankles spread eagle on the bed face down.  He was blind folded and still in his dirty ripped clothes.  On his back was a pair of scissors with a red satin bow on it.  My first thought was this boy knows me too well, a mixture of romance and kink.  And I noticed no gag so I asked “So, how is the hole?”

He responded “Properly prepared.”

I growled at him.  I reached over to feel his pucker through the hole in his jeans.  My finger slide in without any pressure.  His ass felt full.  I could feel my finger pushing back and forth through the sludge of spunk in his ass.   I was drooling.  My dick jumped.  And he moaned.  I pulled out my finger and tasted it.  It had a sharp but sweet taste.  But it was so thick.  I moaned like it was the best vintage of wine I had ever tasted.  “Your hole is so loose and full”

“I posted my photos and ad on craigslist that I would be at the bath house taking all loads.  I did pretty well.  And I knew I had the boys lined up for this morning.  I wanted to show you how good my hole really can be.  Now it’s ready for you sir, please taste, use, and score my hole”

“Happily.” I said as I grabbed the scissors.  First I cut waistband of the pants just to see that wonderful set of ass cheeks.  At the top of his ass I noticed the end of red mark.  I then started cutting his shirt up the back and found red marks all over his back.  I have to say the sight turned me on.  The thought of this big 6’2” broad shouldered man being abused and whipped just went straight to my dick.  I said “Did you take some abuse?”

“I had them lock me into a fuck bench at the bath house.  One of the guys figured out when he lashed my back my hole would tighten up.  I had told them not to let me out till 8am this morning no matter what so they left me and some of the other guys got off on my screams and moans and hole tightening.  I’m sorry if the marks displease you.”

“No boy, they don’t displease me.  But I would have loved to have seen or at least heard it.”

“If you press play on my mp3 player on the night stand you can hear me moan through the lashes.  I had it recorded with my phone.”

“Damn boy you really did wanna win this” I said as I reached over and hit play.  As soon as I did I heard the belt hit his back. The scream that turned into a moan was too much for me.  I stood up and stripped. I then opened the ass of the jeans so nothing would get in the way of his hole.  I snipped the remains of his boxer briefs and pulled them out and off of him.  He whined when this happened because I’m sure it rubbed his dick.  I wanted to get deep.  I then got up on the bed and started rubbing my cock along his crack.  The slime of cum was everywhere.  I then pulled back and continued listening to his sloppy fucking on the recording and the whipping of his back.  I lined myself up and waiting for a loud scream.  When one finally came about 20 seconds later I plunged full length into that hole.  I felt the cum gush around my dick and onto my balls.  Jake just moaned and smiled.  I swirled my dick in that hole.  I traced the scissors on his back.  I cut the rest of the shirt off and noticed chains laying by either side of his chest.  I knew they would be connected to his nipples.  This boy was seeking torture today. “damn boy nipple clamps too.  You really wanna be hurt today.”

“My hole is wrecked, and I know you love that but I wanted you to be able to make it a little tight if you wanted too.  So I gave you some options.”

I reached down and grabbed both chains.  When I pulled, true to form his hole clenched as best as it could on my dick.  He also screamed.  The scream probably made me harder than the hole did though.  I was already hard a rock and stirring cum in a great hole, so no complaints.  I then pulled out and dove face first into that hairless big ass.  I was over taken with the taste.  As I sucked on the hole he pushed some cum out for me to taste.  It was fantastic.  Ass juice and cum filled my mouth and I swallowed a wonderful load.  As I was gobbling his ass full of cum I noticed another chain in his pants.  I felt around and found it was connected to a choke collar on his balls. I pulled on it hard and felt his ass ring try to close on my tongue that was digging for more cum.  I also felt his scream rattle through his body, quickly turning to a moan and shutter I could feel in his ass.

“Please load my hole sir, enjoy, abuse, and overflow my hole”

I put my thumb in his hole and then pushed in my dick with it.  He squirmed in the perfect way, almost wanting to fight the restraints but then relaxed into it.  I kept fucking him and then pulled his nipple chains.  I felt his hole start to spasm.  I knew he was cumming so I reached down and pulled his ball chain.  His back arched and hollered in ways I never knew he could.  That threw me over the edge and added my slime to the deepest part of his ass I could get too.

Spent and happy I rolled off him.  I called for Gabe to bring me a sharpie. 

“How did I do sir?”

“Very well, you know me too well”

“Is there anything I could have done to make it better for you?”

“God I don’t know”

Gabe showed up sharpie in hand and I could see the cock cage inside of his jock strap.

“Are the boys gone?” I ask

“Yes daddy” Gabe says.

“Okay, I want details later.  First I must grade this hole.”

I write 9 on the small of his back, covering some of the lash marks.

“Plug that hole.  I’ll wanna taste it again later.”

“Yes sir”

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  • 2 years later...
  • 4 weeks later...

Part 3

“So jakes hole was a 9? He did better than me?” Gabe asks with a pout. “What was better about it?”

“He added some romance, kink, and two very larger black cock loads delivered deep. Plus a full night of bathhouse abuse on his hole meant it was super loose. Not only didn’t he turn away any loads he had no control of how fast they came at and in him.”

“Okay daddy, I’m sorry I disappointed you.”

“Gabe you didn’t disappoint me in the slightest, you just have lots left to learn.  Your cute and you can score a lot of cock that way.  But there is more to a fuck than just the cum and jizzjoy you enjoy. Learn from your brother.”

“Am I allowed to be unrestrained yet David?” Asks Jake

“Hmmm…yes, Gabe help me release him.” I say as we both release his d rings.

“Now Jake put the restraints on Gabe.  Tie him up in his room, and post an add for him on craigslist.  You watch the door for him, don’t need anything serious happening to him.  But get him fucked by the crazy and aggressive.  Make sure they bust his balls too while he is in the cock cage.”

Gabe looked a little scared.  “For how long?”

“I haven’t decided yet.  I won’t make you do it if you don’t want to but if you want to be a better cum hole this is the way.”  He then put his wrists out to have the restraints put on.  Jake put them on him.

“Now go to your room and I will be there shortly to truss you up.” Jake said as Gabe left, “So what all do you want for him?” He said to me

“Biggest cocks you can find that show no mercy.  Hell, get him fucked with a pierced cock if you find one willing.”

“Can I fuck him?” Jake asked as he finally slides the butt plug into his cream filled ass before anymore jizz can leak out.

“As much as you would like, but you are responsible for him.  He doesn’t get to say anything about when or how much fucking he gets. He may only ask to stop when there is a break in the line to fuck him.”

“Got it. Safe word?”

“Only the ultimate safe word gets him free now that he has agreed to this, I quit David”

“Okay then”, he said as he turned to walk away.  Before he could though I stopped him, and kissed him good.  Put his hand on my cock and then he remembered.  He then cleaned my cock for me.  “Anything else you need before I go deal with Gabe?”

“Yes, use the computer in here to put the ad up and bend over.  I wanna lick around the plug.”

Jake smiled and moved to his computer.  “Is this for extra credit?”

“No, I just want to taste a little more.”

Jake bent over at his desk rather than sit down so I could lick around his hole and the large black plug holding the river of cum in his ass.  I smiled, appreciating the sight before me and knowing he happily made and gave me this hole.  I saw a small line of cum down his right thigh that had leaked down earlier and went for it with my tongue.  I licked it and followed it up to his ass.  Enjoying his moans and squirms as I did.  When I got to the plug I was licking all around.  Trying to find any possible leaks around the plug.  Jabbing my tongue on the edges of his hole to see if there were any cum droplets there for me to enjoy.  I found a few and savored them.  When I finally felt his ass was clear of any more flavored pockets of spermy deliciousness I smacked his balls once and then his ass.

“Are you done with Gabe’s ad?” I asked

“Yes, Sir”

“Good, take your laptop to respond to messages to his room, makes sure he is restrained and prop his outside door open.  I need to run to the store to get a few things for the trip.   I was hoping to take one of you with me but it looks like you guys are both not store ready.”

“Sorry, Sir”

“No sorry about it Jake, I would rather have you at home marinating in cum than just along for the ride to the store.”

“Okay, Thank you David”

With that he bowed to me and then turned around and bent over so I could smack his ass before he left. God, I love that guy.  He knows how to play into my kinks, and gets so much enjoyment out of it.

So, I went to the store, I had thought Luke would try to find or stop me but I didn’t see him.  I texted him to make sure he wouldn’t need judging for at least an hour and he said he wouldn’t so I went.  As I was leaving I saw a few guys arriving and assumed they were for Gabe.  One was a large linebacker looking guy, and the other looked like a biker.  I smiled knowing people thought my house was a whore house.  Living in a heavily touristy town has its advantages.  Between the 3 of them at least one of my boys would be willing to take anyone’s loads. I ended up at the store longer than I had intended but I had been distracted by a handsome sales clerk that wanted to flirt.  His name was Josh according to his name tag, and he was wearing some very tight black dress pants and a tight stretchy red button down. He stood about 5’11’, tight waist, decent chest, a shelf of a butt, and nice shoulders.

I asked him “Do you flirt with all the guys that come in here?”

HE said, “No only the gay ones with money.”

I laughed at him and said “I already had a houseful of guys that I am sure are more dedicated to meeting my every want and need than you ever could be.”

He frowned and said “You can have me right now in the dressing room.

 So I threw the questions that usually stops these pretty gold digging boys, “Okay, first I have to ask, when was the last time you were fucked?”

“Last night”

“Did he cum in you?”

“What? Well kind of, we were safe.  He came in the condom as it was in my ass.”

“Do you have the condom with you?”

“Um, no.  It might be in the back trashcan tied off still.”

“If you had it and you would let me shove my raw cock up your ass on the cum from that condom I would take you up on that offer.”

“That’s…..weird…..and kind of gross, Sir” He said as he made a grimace.  I looked at his pants though and saw the start of a chub.

“Your dick thinks otherwise, so are you gonna go look for thata cock juice from last night or just start preparing for my next visit.”

He was blushing but excited by the idea I could tell.  “Um, I’m not sure I can find it tonight Sir.”

“Are you going to ask me again another time then?”

“Well…..I…..Mean….i always play safe. So maybe I’m not the boy for you.”

At this point I saw his coworker walking over to see if I needed any help.  I whispered in the boys ear. “Go find the condom, dig to the bottom of that trash can if you have to.  Open it up and put it all in your ass......tonight. Then come back on the floor and enjoy the feeling of your squishy ass.  And next time know what to offer to the man you are trying to seduce.”  With that I licked his ear and started to leave the store.  I watched him as I left and saw him head towards the fitting room.  As I headed to my car half hard because I now knew I just created the start of another cum slut I got a text message.  I looked down at my phone to see it was from Luke.

“What time are you going to be home sir, my ass can be ready anytime in the next hour or so.”

“Headed home now I replied.”

 

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  • 3 weeks later...

  I was super excited to see what Luke had prepared for me.  I knew it was going to be good but I can’t say I wasn’t hoping it would surpass the other boys because that would just make it the best thing ever for me, and though I cared about and loved all these boys di for me, this was my fantasy playing out. I was half hard already from the sales clerk trying to tempt me and me knowing he would be a hungry cumslut the next time I came to the store. But knowing Luke had prepared a cum sloppy feast that he thought would win him this contest had me speeding faster than I probably should have. About halfway there my phone started ringing. I looked down and it was Jake. So I answered it.
“Whats up Jake? Are you keeping your fingers out of your hole for me?” I said as I pushed the send button. As soon as I started to listen I heard the unmistakable sounds of sex in the background.
“Yes david, my plug is firmly in place. I haven’t touched it, and I am wearing the tight vinyl shorts to catch anything that might leak out.”
“And this is why I keep you slutty boys around.”
“Thank you sir”
“Is there a reason you called Jake?” As I hear this I hear a scream in the background.
“Yeah, the ad has produced some really rough fuckers, He just had a trucker with a PA fuck hell out of him and he has been crying for about 15 minutes.”
“Did the trucker cum in him?”
“Yeah, three times”
“Has Gabe asked to stop?”
“No, but he is sore, I can tell”
“Do we know the guy plowing him now?”
“It’s Jesse from the gas station.”
“oh good, he will rough him up good and leave one huge load in that hole. Do me a favor put Gabe on the phone, Jesse won’t mind. Actually get behind him and slide a finger or two in with Jesse’s dick after you give Gabe the phone. I wanna hear them go in.”
“Yes Sir” I hear some shuffling and the constant twacking of skin as I know Gabe is getting plowed. And then I hear some sniffles and whines as the phone gets to Gabes ear.
“Jake was concerned about you Gabe, he said you were crying. Are you wanting to stop?”
“NO sir, I don’t want to quit you david. This body makes you happy. This dripping hole keeps you happy. I wanna do everything to keep you happy.” I can hear his tears, the uncomfortable whine in his voice, and the pain of every deep thrust he is taking.
“Well I don’t want to ruin your hole. I just want it well used, cum filled, and maybe leaking a little jizz.”
“I know sir, that is what I am….oh fuck!” he yelled and then gasped.
“oh yeah I told Jake to add a few fingers and make sure u were stretching properly. Do u want him to stop?”
Through more tears and whining I heard Gabe say, “No, sir. I wanna make u happy.”
“Well your noises are keeping me hard to go fuck your brother Luke. So I am very happy right now.”
“Thank you sir.” I hear Jesse's growl starting in the background.
“oh you are about to get a massive load shot up that well worn ass. Now I need u to bear down hard on that massive dick and do ur best to keep all that cum in.”
“Yes, sir.” He says in a whine. “Fuck it hurts a LOT sir.”
“It’s almost over Gabe, try to swallow his dick with your ass and make him feel good like u would for me.” I can hear Jesse's growl getting louder. And then a howl and I know he is erupting into my boy. The dick super swelling in Gabe to deliver the flood that is Jesse's load makes Gabe gasp in more pain as the spunk paints the already cummy walls that are now Gabe’s guts. “Good boy Gabe, now clean his dick and swallow his after sex piss. If u can manage not to spill a drop u can stop taking any more cocks past what is already waiting for u. And give the phone back to Jake.”
“Yes sir.” Gabe groans into the phone. As the last grunts of Jesse's mind numbing orgasm passes the phone is handed over. All I can think is how much Jesse loves fucking destroyed hole almost as much as I do, but he likes destroying them more than I do.
And then I hear Jake on the line, “Yes David?”
“Is there anyone waiting for Gabes hole?”
“Not at the moment, we had hit a bit of a dry spell, I was gonna long dick him myself till I find someone.”
“I made a deal with him, if he can drink all of Jesse’s after sex piss without missing any he can stop.”
“Shit david, Luke can barely do that and he is practically a piss vacuum.”
“I know, but hopefully Gabe is motivated. Either way get the large green plug ready for him. If he succeeds plug him up, leather speedo and set him next to the pool. If he fails, long dick him till u find around 3 more. Then plug and pool. I'm almost home but Luke is waiting for me.”
“Got it boss"
 

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Fuck this is so good! At that point, how can any bottom get enough? And on the one hand, drinking the piss from that rough stud sounds awesome, but then he doesn't get any more dick for a while. On the other hand, if he doesn't succeed he gets more dick from Jake and then a large plug in his ass. Part of me wants him to fail just so Jake can long-dick him.

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  • 1 month later...

I had to hang up the phone at that moment.  I knew if I kept listening I would go to gabe’s room instead of Luke’s and I was already hard as a rock. I needed some more cum sloppy hole. When I got home I saw several cars in the front, recognized Jesse’s truck, but not the others. I pulled into the garage and started heading into the house.  There was still the smell of cum in the house. I assumed from Jake but was hoping it was all my boy’s sweaty, musky, cum soaked sheets, holes and lives.  I headed toward Luke’s room.  As I walked in I saw him in all of his glory.  Short blonde boy with the perky little ass.  Blonde body hair, Short blonde hair on top.  I was staring at his perky ass as he kneeled on the bed. he was jacking off into a wine glass as he faced away from me.  There was already a good amount of a creamy white milky substance filling the glass about a fourth of the way.  As I entered he started to shoot his load into the glass.  He always shoots large milky loads that taste great.  As it hits the the glass I notice he is trying desperately to hold all the cum in his hole in but his orgasm is causing his hole to pulse and want to squirt cum out.  I dive for it and start licking his hole.  His body is shaking from his orgasm.  I’m lapping at all the cum I can find around his hole.  After 5 or 6 good squirts out of his dick and ass the shaking calms a bit and he pulls the ass away from my lips and hands me the wine glass.

“I wanted to have this sitting on my back while I was laid out when you walked in so you could pour it on top of my ass. I’m sorry David.” I smiled as I took the glass and instead of pouring it on his ass I poured the cum cream straight into my mouth.  Savored the funk, the tang, and the joy this boy has brought me. I pushed it into every corner of my mouth so the flavor would stay and then I kissed him.  I forced my whole body against him.  I fell on top of him and felt his massive pecs, and nipples I love to chew on till they bleed with my hands and started tugging on them hard.  I then felt him reaching away from me toward his nightstand.  He had was looked like a small insulated lunch box over there.  “I have something else for you sir.” 

“Oh?” I said, as I let him free a bit to go to the box.  He rolled over under me and grabed at the box.  He opened it and handed me a shot glass full of frozen cum. “You made a devil’s dick?”

“I had to do anything I could think of.  The cold helps keep me tight when you fuck too.”

“How many loads have you had?”

“I lost count Sir, I started out at the bar and got a few of my regulars to give me a few in the bathroom, and had them pass my name around to anyone that would think they wanted to fuck me. That got me up to like 10. Oh fuck” He said as pushed me fingers into his well fucked hole. “I also sent a message to one of my friends at a frat on campus.  He knows…mmmmmhhhhh….how I love cum.  So I told him to gather as much as he could.  He said they were having a party that….fuck….night.” I was digging in his hold hard, enjoying how warm and sloppy it was.  I knew when I added the devils dick he would tighten and I would want to fuck hard and fast so I wanted to hear his whole story first. “So he challenged all the older brothers to see who could fuck the most, girls or guys he didn’t care but they had to bring a tied off condom to prove it.  Then he sent all the pledges….Oh shit that is stretching it a lot david……um…..he sent all the pledges to the basement with a economy pack of condoms and said they weren’t allowed at the party till they filled all of them up with loads.  He said it was so the older guys could get laid, not the pledges.  Oh fuck David please take my hole.  You own it.”

“I will when I’m ready Luke.  You are telling me a story.  I know 4 fingers feels big in your hole boy, but I’m just playing in it. “

“Well I kept getting fucked.  I had all kinds of regulars.  Only down side is a lot of them wanted to piss in me too.”

“Did you let them?”

“One at the bar did before I could stop him.”

“Awww, poor baby” I said as I punched on his prostate.  He was squirming and moaning.

“I had to drink a lot of piss to keep them from piss fucking me.”

“That makes me happy”

“Thank you sir.  I found a few large dicks to fuck me this late last night and had be waiting on the frat boy…..oh god…. condoms. My friend made me go pick them up about 5 this morning.  He fucked me really hard…..harder….. and gave my hole as a reward to winner of the fuck contest.  He then poured probably 30 of the condoms in my…..fuck…… hole and set me home with the rest.  I then had to drink all of his piss….shit when you spread your fingers out in me it makes me wanna scream….  He had drank a lot of beer.  I was belching piss breath and leaking cum out my hole as I was trying to leave, but he rang out the walk of shame bell and told the pledges to catch me out side.  They did.  None of them wanted to fuck me but they all pissed on me and and I swallowed as much as I could.”

“You are such a hot little slut Luke”

“I do it all for you david.” I couldn’t take it any longer and slide the devils dick into his hole through the palm of my hand with my fingers still in his hole.  He actually screamed then.  His whole body tensed around my hand.  I pushed the devils dick right against his prostate.  He was hard again at that.

“So I was tasting frat cum this morning?”

“Yes sir” He said through gritted teeth.

“Nice, You should have mention” I said as stretched my fingers in his hole yet again.  He whined.

“I wanted to play fair sir” He said as he squirmed.

“And you did.” I couldn’t take it any longer.  I took my hand out of his ass and started licking my fingers as I stared at his gapped cum shine covered hole.  Stuck in all that fine blonde ass hair.  I slapped his ass for all I was worth with the hand that wasn’t in my mouth.  He winced and tried to close his hole, which he did but as he relaxed so did his hole.  That was it.  I lined up my cock and shoved it in.  I hit the devils dick on my way in and it felt exhilarating but also calmed my orgasm a bit.  Luke just grunted.  I was going to enjoy this.  “So no leather, vinyl, or kicking stuff like jake tried?”

“I know those only work if you are in the mood for them.  I hoped a perfect blonde cum leaking hole and what I hoped would be an endless supply of cum would put me over edge.”

“Your hole is delicious, and a walking orgasm to look at. Now we just have to see how it fucks in this condition.”

“Well I ….hope….sir.” I started sawing on his ass, enjoying the slime coving my dick and watching it froth in this beautiful hole.  Feeling my dick warming and melting the devils dick.  I started smacking his ass to feel his hole tighten on my dick for quick flashes.  Then I leaned forward over my boy and reached for his nipples.  I grabbed onto the biggest and best nipple I had ever seen on a blonde boy and tugged as if my life depended on it.  He screamed and his hole finally tightened enough for me to truly fuck and not just play around in.  Every time I would pull he would scream but it would turn into a moan.  I was in heaven and knew I could go for a while if I slowed down or just plant my seed I wanted to so bad since the moment I tasted his hole at breakfast.  I started picking up speed when luke lunged back impaling himself on my dick and wouldn’t let me get up to speed to unload in him.

“I’m not ready to be judged yet.”  He reached into his nightstand drawer and pulled out a small sports bottle full of what looked like creamy lube. He pushed me on my back and started to ride my cock.  I could feel the cum sliding out of his ass and down my balls and taint.  It was so hot.  He then turned the sports bottle over and started squirting it into my mouth. It was more cum.  He was trying to drowned me in it it seemed.  I was swallowing as fast as I could and he was riding for all he was worth.  Here I was staring at a hot blondes chest as I try to rip off his nipples as he is riding my cock and feeding me cum. It took no time.  I heard the bottle give a squelch telling me it was almost empty and that was it.  I started to flood his guts. I came so hard in his hole that breathing and swallowing wasn’t possible.  My choking and sputtering and feeling me cum in his hole seemed to throw him over the cliff again.  I felt him spasming on my cock as his cock tried to shoot what little juice it had left in it on my chest. My face was a cummy mess from trying to breath and swallow and my balls, ass, and legs were sitting in a puddle of Lukes ass mess and I couldn’t be happier. Fuck was all I could think.

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  • 4 weeks later...
  • 1 year later...

I let go of Luke’s glorious, sorry, and right now very red nipples finally and he collapsed down on my chest, not removing my cock from his ass at all. I laid there in what felt like ecstasy for several minutes feeling drips of cum run down my cheeks, balls, taint, and chest. I felt like I had just taken a bath in man seed and I couldn’t be happier. Luke was panting his little heart out on my chest. I think he was scared to move. 
He finally asked, “How was it?”
“Better than I expected, but like the other boys, I wont tell you, I will score u on your lower back and you guys can go compare scores and see who is going on the weekend getaway.”
“That’s fair, but please don’t make me move yet. Ur dick is the only thing holding any cum in my ass right now, and I don’t have the energy to squeeze to hold it in till u can plug it.”
I giggled, and groaned in enjoyment of that fact. “Ur still leaking down my balls"
“I know, but without u in there it would be running out, not just leaking"
“So I should just piss it out?” I said jokingly.
“Its your hole, david, you can do as u want with it, but you had me make it this cum sloppy, I don’t think that is what u want for it just yet.”
“No, I wanna taste all 3 holes together, later, so let’s get u up and plugged" and with that I found his nipples again and pinched and pulled with all my might. And as expected his hole spasmed shut, spitting my softing dick out. He cried out in pain and tried to pull away from me, but I had a good hold on him and rolled him over on his back. He relaxed into the pain eventually, so I let go, sending another chill thru him. I pulled his legs up and grabbed the widest but shortest plug I could quickly find in his nightstand drawer and shoved the orange plug into his hole. It was quite a thick one he obviously wasn’t used to wearing. It also had a loop on it to attach a leash if one wanted. I managed to get it pushed into his hole with a bit of a squelch. I then licked around the plug to clean him up a bit. He was moaning and groaning quite a bit. And I could tell the plug was a little uncomfortable but he said nothing about it. I left him like that for a moment to go grab a sharpie. On my way to my office I saw jake waddling towards the patio, black plug still in place. It made me smile, and almost chase him but I knew I had to deal with Luke first. So retrieved the sharpie and a damp towel to clean myself up a bit. Returning I saw Luke struggling to be comfortable, he was using his fingers to collect, clean, and eat any cum he could find on his body, all while trying to deal with the large plug in his ass. It made me smile and so happy. I told him to roll onto his stomach. He did. And I wrote his score on his back. I started to attach the leash to his plug and he stopped me, which was unusual. 
“Don’t attach the leash back there, I’m afraid u will pull it out my accident and waste the sloppy mess we have created for you. Just use the strong nipple clamps and attach the leash to those if u want a leash.” Luke both loved and very much hated pain in his nipples, so if he was volunteering them up it meant he really cared about his hole staying the stretched cum dump it was. I however loved the faces his nips caused him as well, so of course I attached the clamps and walked him to the patio.

There laying face down on a lounger was gabe in a black leather speedo, obviously exhausted with a sharpie 8 on his back. Next to him was Jake sitting up playing on his phone, with one leg pulled up probably to make it more comfortable to sit, in his vinyl shorts. Every tug on the leash got me a gasp till we got to the patio table just across from the lounge chairs.. Luke looked nervous, I knew because he thought I was gonna make him sit. I almost wanted to make him Just to see his faces but I didn’t. I wanted to see all my trophies lined up. I called gabe and jake over. Turned them around and savored each hole. First was Jake’s. I pulled his shorts down, and they were sweaty, but not much leaked cum, I pulled his plug, sucked quickly like a lollypop and then dove for his hole, it was still a little loose, and good and sticky. Tasted wonderful bent over that table. When I looked up,  I saw gabe making out with luke, but jake had Luke’s leash tugging on his nips while I was eating the hole. I was a little worried about gabe’s tongue with luke nips taking that much torture. But gave didn’t seem to care. When I felt like I couldn’t find anymore large globs of cum or flavor on jake I pulled back and moved over to gabe’s hole. As I pulled gabe’s speedo down I told luke to start fucking jake. He moved across and tried, jake was gonna be fucked but because he had Luke’s leash it was gonna be on Jake’s terms. I loved it. Gabes hole still looked a mess with that big green plug squirming in the hole. He was moaning a lot and I could tell a little jealous that jake was getting fucked. But I also knew Gabe was actually sore. I pulled on the plug and gabe shouted quite loudly at first. I reached between his legs and found his junk in the cock cage I had ordered him in earlier and it made me hard. I squeezed and pinched at his cock in the cage and he squirmed even more. Finally I gripped his balls way to tight with one hand as I yanked his plug out with the other. He screamed, and then sighed in relief. His hole dropped cum. I attacjed it with full force as I devoured his swollen ass lips and drank down all the cum and ass juice I could find. It was like heaven. When he finally started to relax into it I told jake to start fucking gabe again while luke was fucking him. Gave stayed laid across the table as Jake moved behind him, the whole time pulling Luke along with the leash to keep Luke’s dick in Jake’s ass. I just sat back as they made this train, enjoying all the flavors on my tongue and knowing it was gonna be a glorious trip.
 

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