Dan vs The Daddy
(plus a bonus spitroast)
Below is characters who appear in this story (I named them!) and brief descriptions of them. Let me know if there are any body types or characters you want to see!
- Dan - 23, 5'8, 6.5 inch cock, Vers, Blonde hair, blue eyes.
- The Trickster(Nick) - 32, 6'2, 7 inch cock, Top, Black hair, brown eyes.
- The Daddy(John) - 43, 6', 5 inch cock, Vers Bottom, brown hair, blue eyes.
- Chubby(Michael) - 30, 6'4, 8 inch cock, Vers top, brown hair, brown eyes.
- Gangly(Leon) - 27, 5'10, 7 inch cock, Top, blonde hair, brown eyes
- Twink(Benny) - 20, 5'6, 5 inch cock, Bottom, black hair, brown eyes
- The Trapper(Derek) - 31, 6'1, 6.5 inch cock, Vers top, Dirty blonde hair, blue eyes
The second week approached and I had still not lived down my humiliation, I felt the ache in my hole all day after I got pounded by The Trickster, I knew I wouldn't vs him again in a while unless we set up our own match. I wanted to beat him more than anything but I knew he would probably win again so I had to work my way up and keep fighting in the weekly rounds.
When I checked my fixture on Wednesday, I saw I was up against 'John' and judging by his picture and match history, I realized he was The Daddy I saw getting obliterated last week. Yes! This was perfect, watching him last week, I could tell he was sort of like me, had a fighting spirit but once he was getting dominated, he enjoyed himself too much.
If I could get him into a state of ecstasy, I could win the match and begin my climb of the leaderboard. I didn't get to see him much in action so I had no idea what his specialty was, maybe if I went to the matches early on Saturday, I would get to see him fight someone else first or I could ask around for advice if anyone would give it to me...
"Next time I see you in this place, I want you wearing a green wristband, so I can re-arrange your insides whenever I feel like it, otherwise I'm dragging you into a ring and embarrasing you even further" I remembered the Tricksters words and shuddered, its not like he could actually make me wear a green wristband, they still interested me but I didn't want to exhaust myself before my actual match by actually wearing one.
Saturday rolled around and I was back in my washed singlet, and I was 2 hours early for my match so I could to some recon, unfortunately, The Daddy hadn't arrived yet so I couldn't watch him fight but there was a couple of other fights going on. The Gangly guy I saw last week was fighting against someone I hadn't seen before, an older 6'1 man with a rock hard cock.
What was more surprising was the fact that Gangly had a ball gag in his mouth and handcuffs hanging off one of his wrists. After watching for a bit, I realised that everytime he went to fix his predicament, the older guy would lunge forward holding a small rope. So he was a Trapper then, someone who brought tools with him to lock up his opponent before dominating them.
I checked the board next to the ring, looks like their names were Leon and Derek, with Derek being Mr Trapper's name. Derek and Leon were both still clothed, with Derek in a full singlet but Leon in just his usual speedos. Around Dereks waist was a belt which is where he kept his tools, it weighed him down and gave the opponent something to grab but clearly the pros outweighed the cons when he finally managed to get Leon to misstep, hip throwing to the floor and locking the other handcuff behind him, trapping Leon's arms behind his back. Derek wasted no time in using his rope to tie Leon's legs together, completely immobilizing him.
Derek was the clear winner but unlike most of the heels in the league, didn't have an ego or showmanship, as he nonchalantly pulled his cock out of his singlet and swiftly yanked Leon's speedos down, only enough to expose his hole. Plucking a small bottle of lube off his toolbelt, Derek applied a generous amount to his cock and Leon's pucker before plunging his cock into Leon, wasting no time in picking up speed and railing poor Leon.
Derek fucked him for a couple minutes until he groaned softly, filling Leon's guts with his cum. Leon panted heavily through the ball gag, curses being muttered but unintelligible as Derek drew his cock out of Leon, spilling a little bit of cum before pulling Leons speedos back up his legs, covering his good work and began untangling Leon as the ref blew the whistle.
Without another pause, Derek left the ring and walked over to the showers while Leon was still struggling to walk with cum leaking out of his undies, also heading in the direction of the showers. I decided to walk over and see if either of them could help me with my investigations.
Derek was in one of the shower cubicles, all open of course and Leon was nowhere to be found, probably around the corner near the lockers so I approached Derek whose naked body was proudly on display underneath the shower, warm water rinsing away the sweat from his gorgeous body. He was actually quite hairy, with a nice bush on his cock, a real grizzly bear, which matched his demeanor when he practically snarled at me-
"Enjoying the show twink?" His hands moved down his body and gave his long cock a couple strokes as he licked his lips while speaking down to me. I had just witnessed how dangerous this man could be, if I wasn't careful, I would probably end up hogtied and blindfolded in this very bathroom... it was tempting but I needed to know about my upcoming opponent.
“So I was actually wondering, I’m up against John and I could use a few pointers since the last time I wrestled, I didn’t do so well plus it would be nice to know what strategies he uses ahead of time since I haven’t gotten to see him wrestle much” I spoke quickly, trying to gauge if I was heading in the right direction by watching his reactions, to my dismay, he kept stoic the whole time.
“Yeah you definitely could use some tips, I saw your match against Nick, it was brutal but I ain’t just going to out John to you, he’s a good friend and part of me wants to see your cute bubble butt getting drilled into the mat again.” The compliments cut like a knife, he just saw me as a jobber, a piece of meat that the tough guys could throw around the mat.
He stepped out of the shower and walked past me towards the bench-
“Unless...”
He reached his hands out and fondled me, one hand cupping my bulge, the other caressing and squeezing my ass.
“If you can pleasure me, I could be convinced to tell you what to watch out for, give you a fighting chance” He finished his sentence by slipping his hand into my singlet and massaging my hole with his fingers.
It was a tough decision, sucking off this handsome man plus getting info would be heaven but if he doesn’t tell me anything and someone was to find us in here, it would be a lose/lose. This decision was crucial but Derek apparently wasn’t about to let me take my time making it as 2 of his fingers pressed into my hole as he roughly jerked me off through my singlet as well.
“Running out of patience here...” He whispered in my ear as he began to fingerblast me, scissoring my hole open.
“Alright, I’ll do it” I spurted out before I could even negotiate better terms. Idiot.
“Great! Crawl on over here then.” He retracted his hands and briskly walked over to the bench, sitting down and spreading his domineering legs in front of me. His cock was standing up straight, drawing me in. I walked over and knelt between his legs, taking his thick shaft in my hands and admiring it.
“Oh, Nick mentioned you got no gag reflex so I hope you dont mind cutting to the chase” He grabbed my head abruptly and forced me all the way down his cock, it was about the same size as mine but slightly girthier, my nose was pressed into his hairy bush and my hands naturally went and cradled his balls, tugging on them as I sucked him deep.
Somehow he smelled and tasted amazing, sometimes he would hold my head down just so I was forced to smell his musk and it was delightful, exactly what a man should smell like. He wasn't gentle but he wasn't rough either, guiding my head up and down his shaft. I palmed my own bulge, aching to cum but sucking this guy off well had to take first priority.
Every now and then he would pull slightly on my singlet, making it ride up my crack, exposing my cheeks and giving me a slight wedgie, it just made me want him to cum down my throat even more and taste his delicious semen.
"You are doing a mighty fine job there, making me feel real good." He moaned out, pushing my head down onto his cock and holding it there again. "I hope you don't mind if we get some company"
I didn't really process what he said until I felt someone kneel behind me and massage my asscheeks roughly, spreading them apart and a cock filling the gap, rubbing up and down on my hole.
"and here I thought you didn't want me to plow you yesterday, now you offering yourself up for me? So thoughtful" I recognised Leon's voice from yesterday, I was a bit annoyed that he was the one behind me about to fuck my ass but I was in man-heaven, sandwiched between these two that I couldn't even pretend to resist. I started grinding my ass on Leon's cock while bobbing up and down on Derek.
Leon pulled my singlet to the side, and pushed his head against my hole, I could feel his cock was already lubed up thank god, the lube helping him as he stretched inside me. This was the monster I could grinding against me yesterday. Finally his head pushed inside me with a pop, and he wasted no time in fully sheathing his 7 inch cock fully into me. I could feel his stubbly pubes against my ass as he gave me a second to adjust.
Derek started thrusting into my mouth again, reminding me of the other cock I had buried into me, he was moaning loudly so I knew he was near his climax. If I could finish him off, I might be able to escape before Leon came deep in my guts then I could wash the lube out of me. I was worried that having a lubed up hole would make it easier for Daddy to take advantage of me in the ring.
Leon started moving hips back and forth, drawing his cock out of me before slamming it back, unlike Derek who was smooth and sweet, this was a domination for Leon, he was telling me exactly what he thought of me with every thrust.
Derek's hands released my head and I could feel him making gestures to Leon, communicating something he didn't want me to see. I found out why soon enough when Leon snaked his arms under mine, wrapping around my neck and quickly lifting me off of Derek's cock, trapping me in a KNEELING FULL NELSON HEADLOCK while he kept pounding into me. The sudden lack of intrusion meant I could breathe properly for a second, but only a second as Derek stood up and shoved his hard cock back into my mouth.
I wonder if they knew about my plan to escape, as now I had no hope, trapped in this position, Leon pushing my mouth onto Derek, alternating with his thrusts, basically seesawing me on their cocks. My arms flailed about helplessly as Leon put the headlock on tighter, bending me into him even more. Derek started to speak-
"I think you did great, my little twink friend, so I'll help you out. John's specialty is holds, he will fold you up like a preztel if you let him grapple you. He is also fond of spanking, living up to his title as The Daddy, don't let him bend you over his knee otherwise you won't be able to sit down for a couple days. If that happens tho, just let me know and you can sit on my lap instead" He ended his sentence with a chuckle and slowly drew his cock out of my mouth. He stood in front of me, jacking himself off as I realised he didn't intend to finish inside me.
"W-wait, no....don't" I sputted out "I won't have time to clean it off" I pleaded with Derek but it was too late, he moaned and leaned his head back as his cock spewed out white ropes, his load covering my face and body. It was massive and thick, I could feel the ropes succumb to gravity as they left streaks down my singlet, which seemed to be his main focus. He wanted to mark me before I stepped in the ring and I was trapped in this headlock so I had to let it happen as well.
He walked off and left me in the hands of Leon, who had not stopped fucking me during that entire exchange, that's when I started hearing applause and cheering from the crowd. Shit! My match was about to happen and here I was getting railed in the bathroom, if they came looking for me, my reputation would sink even further.
Even though it would be embarrasing, I had to channel my inner bottom and work Leon's cock until he came, and fast. I started bouncing up and down as he thrust into me, forcing him even deeper as I moaned his name.
"Leon... fuck, fuck me harder... breed me.." I breathed out and I could feel it working, his thrusts became sloppier and faster.
"Call me sir and beg for my cum" He replied, panting hard.
"Cum inside me, please sir" I forced myself to say these words, knowing I needed to get to the ring as soon as possible. Luckily, the 'sir' pushed him over the edge as he slammed inside me and held it there, I could feel his cock pulsing as he filled me up, his sweet load leaking out of me.
He drew his cock out of me, but before I could run off, he made sure to adjust my singlet and then wedgie it slightly so it covered my hole and prevented the cum from leaking out. He then finally released me and gave my ass a smack as I scampered off towards the ring. I knew I looked like a mess but with the knowledge I had gained, I believed that I could beat Daddy wholeheartedly.
I jumped up into the ring as the ref and John turned to look at me, John laughing as the ref looked perplexed. The cum streaking down my singlet did me no favours in looking tough.
"I didn't realise they let cumrags compete, son" John couldn't stop himself as he laughed at me, making my cheeks burn red. It was bad enough in the bathroom but standing out here now in front of him and the crowd, the humiliation was really starting to set in.
The ref called us over and gave us our safeword before retreating to the corner and signalling us to get ready. We moved into the middle, I knew he was going to go for a grapple at the start and try to put me in a hold but I was ready thanks to my efforts with Derek.
We squared off, I could feel the cum still slowly seeping out of my ass but tried to ignore it and focus on the match, these first few seconds were going to be crutial. The ref blew the whistle and John immediately lunged for me but I anticipated it, sidestepping and bringing my knee up into his sternum with a BANG!
He doubled over and coughed while I quickly stepped in behind him, wrapping my arms around his waist and lifting him into a REVERSE BEAR HUG. I squeezed as hard as I could to really get the wind out of him. Unfortunately I couldn't get his arms in the hug so he was able to try and pry my arms off him, he struggled and I could feel my grip loosening so I did what any sane man would do and SUPLEXED him into the mat.
I watched him start to roll over so I scrambled quickly and dived ontop of him, pushing him down to his stomach, kicking his legs out and putting my weight on him so he couldn't move.
My crotch was perfectly nestled into his ass, our singlets the only thing seperately my meat from his juicy rear. I started to grind into him, reminding him of my plans to fuck him soon... but not yet.
I climbed over him and sat on his butt, reaching my hands down and cupping his chin, pulling hard to lock him in a CAMEL CLUTCH. He groaned as his back stretched out.
"I'm gonna stretch you until you break old man and then I'm going to fuck you until you cum on yourself" I pulled hard as I emphasised the cum part, he moaned as I felt his butt tense beneath me. "I can feel you quivering in anticipation, can't wait for me to make your singlet look like mine? Like your buddy Derek did?"
"Derek? What are you talking about?" He groaned out, arms flailing as he tried to keep himself upright.
"It cost me a load on my face and a load up my ass, but your friend ratted you out and gave me an advantage just so he could see me humiliate you" I chuckled out as I applied the clutch harder. I knew this wasn't how I was going to win but I needed to weaken him as much as possible. Unluckily for me, he wasn't weak enough for what happened next.
"That BASTARD, I'm gonna ruin him later but first I have to deal with YOU" He roared out as he bucked wildly and started shaking himself around, my grip wasn't strong enough as he shook me off, we both climbed back to our feet, resetting the match pretty much but this time, Daddy was angry.
"COME HERE" he yelled and lunged for me once again, instead of sidestepping, I tried to backpedal away from him, but he managed to catch my wrist and yank it towards him, throwing me off balance. His next move was to wrap a hand under my shoulder, the other reaching down to my nuts as he squeezed them tight and LIFTED ME across his chest . The death grip on my balls hurt like hell as I tried to oriente myself again.
He followed it up with a BACKBREAKER, slamming me down onto his knee but instead of letting me drop to the floor, he held me there, one hand keeping me steady on my chest and the other still gripping my bulge.
Any move I made just caused him to grip tighter and start twisting my sack around, making me buck my hips into his hand. My back was starting to kill me as well, this was a dangerous position to be in. I needed to turn the match back around quickly.
Unbeknowst to me, all the thrashing and ballbusting had caused my singlet to shift, allowing some of the cum still inside me to drip out onto the mat. John looked down at it and exclaimed "you have been such a naughty boy, time for Daddy to teach you a lesson about what happens to sneaky boys who get fucked before Daddy can fuck them"
I dreaded hearing those words, knowing what was to come next, I tried my best to struggle but he grabbed one of my hands, flipped me over on his knee and twisted it behind my back, chicken winging me as I was now bent over his knee on my stomach, my ass pointed straight up in the air towards his other waiting hand.
SMACK SMACK SMACK SMACK SMACK SMACK
6 strikes landed on my ass, spread across both cheeks evenly as I writhed to try and escape my punishment. His spanks were even harder than the Trickster's and he wasn't even doing it as a way to win. He just wanted my ass to be pure red and raw by the time he was done with me.
SMACK SMACK SMACK SMACK SMACK SMACK
The blows started to speed up as my ass got redder and redder.
SMACK SMACK SMACK SMACK SMACK SMACK.
He took a pause after the 18th smack to reach inside my singlet and pull my hard cock out, stroking it a bit as it dripped precum onto the floor. He also adjusted his own bulge, pulling his cock out before going back to my ass.
SMACK SMACK SMACK SMACK SMACK SMACK SMACK SMACK SMACK SMACK SMACK SMACK
12 spanks rained down as each one shot a little bit more pre out from my shaft, I was begging him at this point to stop, it felt like my ass was burning but his thick hands just reached down and stroked me some more, I could feel myself getting close to orgasm but at this point, I just wanted the punishment to stop.
He let my arm go for a second, and my hope rose just to fall as I realised he was repositoning us into an even worse spot for me. He picked up my legs and threw them around his waist, pushing me stomach down and pointed my face towards the floor before wrapping his legs around my body. I was now splayed across his lap, my ass still up in the air but our cocks now frotting against each other.
SMACK SMACK SMACK SMACK
He began his assault again, spanking me like I was his misbehaving child except this time he took a finger and shoved it into my hole, fingering me while he ruined my cheeks.
SMACK SMACK SMACK SMACK
This went on for another 10 spanks before he added another finger, then another 10 and another finger. I was worried he wasn't going to stop until he was fisting me but lucky for me, he stopped at 3 fingers, pumping them in and out of me rapidly.
SMACK SMACK SMACK SMACK
At this point I think my ass was going numb, and I think he could tell cause I wasn't reacting as much to the spanks. He reached his spanking hand down and started stroking my cock again while he stretched my ass with his fingers. It didn't take long before I felt my cock swell up and I burst all over my singlet again, staining it even further. The bell rung signifying the end of the match and another loss for me was added to the scoreboard.
I thought my punishment was finally over but Daddy untangled us and dragged me over to the edge of the ring, swinging my legs out so I was bent over the edge, exposing my ass to the waiting audience as he knelt in front of me and slid his cock into my mouth, thrusting into me like a useless cocksleeve.
"Free spanks for anyone who wants 'em!" He shouted into the crowd and various audience members walked up to take their turns abusing my butt, some even "missing" and hitting my dick and balls instead. I endured the pain as I sucked on John's cock as I felt it swell before pumping his sweet juice down my throat.
After using my throat, he helped me down from the ring and supported me as I limped towards the bathroom, even though he was the main cause of my pain and suffering, it felt nice to be helped out for once.
Derek was right though, I don't think I could sit down for a week...
I hope you all enjoyed the story, please comment below if there are any characters you would like to see duke it out or even just fuck each other! I also write any kink so don't be afraid to request specifics! Have a great day!
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