Dan vs The Trickster

Dan joins a sex wrestling group for the first time and underestimates just how far some opponents will go to fuck his ass

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Reader discretion is advised, this story contain forced sex content which may not be suitable to all readers. This is purely a fictional story and does not portray real events or real persons.

All characters are 18 or older. This story is fiction, created for entertainment only. 


My name is Dan and I live in Melbourne, its a beautiful city but what's even more beautiful is the vibrant LGBT scene for a gay man like me. I have had quite a few hookups and as a versatile, there was never a drought of people who were interested in me. This story is fictitious but I wish it wasn't  

Here are some of the characters who will appear in this story (I'll give them names eventually) and maybe future stories if I continue this series ;)

Dan - 23, 5'8, 6.5 inch cock, Vers, Blonde hair, blue eyes.
Trickster - 32, 6'2, 7 inch cock, Top, Black hair, brown eyes.
Daddy - 43, 6', 5 inch cock, Vers Bottom, brown hair, blue eyes.
Chubby -  30, 6'4, 8 inch cock, Vers top, brown hair, brown eyes.
Gangly - 27, 5'10, 7 inch cock, Top, blonde hair, brown eyes
Twink - 20, 5'6, 5 inch cock, Bottom, black hair, brown eyes


It was my first time ever competing in sex wrestling. I had been interested ever since I found out it was a thing, I used to watch wrestling porn all the time which made me think it was just a fantasy until I found an online community that hosted it in the city I live in. I messaged them asking if I could join, got some details and on the next Saturday, head into the city, eagar but nervous.

I had bought a nice but tight red wrestling singlet, I was kind of afraid it would get ripped during the day so I thought I would take it easy and just sign up for one match to start with but oh boy I wanted to jump right in there. Seeing all these sweaty men in singlets, speedos and sometimes even nothing tackling each other to the floor. Holding each other down while they slowly pushed their cocks into....

I could feel my singlet swelling up already and got excited until I looked around and realised that that was a bunch of older men all staring me down hungrily.

"You got a problem you need fixing boy?" A man laughed while pointing at my crotch

"Nah this little jobber will be cumming all over the mat soon enough, once he's pinned down by a real wrestler" Another man walked towards me and licked his lips.

For context, I was kind of on the smaller side being 23 and only 5'8'' but I was stocky with strong shoulders and was packing 6.5 inches downstairs so these threats didn't really intimidate me.  Although the idea of jobbing made me drool a little, I was a competitive soul and hated losing so I knew I was going to try my all to win every match.

The rules were simple - anything goes during a match but obviously avoid excessive force, no bleeding, no breaking bones, the ref will give you a safeword before the match that you can use for if things get too intense. First to cum loses unless its inside the other person.

I had almost no experience wrestling in general, so I didn't think I was going to be able to hold people all that well but my plan for my first match was just to overpower my opponent and jerk them off, nothing fancy but I needed a win to get my name out there.

I kept watching the match in front of me as this 6'4" chubby 30 year old man was holding a 6' 43 year old daddy in a BACKBREAKER hold with ease, using one hand to hold him steady while the other jacks him off. The daddy was moaning in both agony and pleasure as 6'4 stretched him further. I could tell this match was a total sweep since the Daddy had no clothes on and was practially squirting precum everywhere whilst the Chubby guy had his full singlet on and barely a wet patch near his monster cock. I started daydreaming about what a match with the 6'4 guy would be like when I felt someone grab my hips and start grinding into my ass, pulling my singlet back and exposing my nuts on the side.

"Hey! Whats the deal?" I turned around and exclaimed. Behind me was a gangly 5'10 man in speedos and a clear hard on.

"Oh sorry, thought you had a green armband on" He sneered and adjusted his junk. 

This wrestling community had a special rule, you could acquire green armbands from the front desk and if you were wearing one, it meant you were down to wrestle anyone, anytime which often meant jobbers could be snuck up on and put into a hold before they even realised what was happening. I highly doubt the sneaky man thought I actually had a wristband on and was just looking for an easy target to get his dick wet. I followed him with my eyes as he walked up to another patron who ACTUALLY had a green armband on and was already naked.

This 5'6 twink had just come out of a match and was breathing hard when Gangly came up behind him and put him in a HEADLOCK, lifting him slightly off the ground while thrusting his hips into the crack on the twink who was leaking cum all over Gangly's speedos.

I suddenly wondered how many guys would take the opportunity to jump me if I were actually wearing a green wristband and considering how many of the older hot tops were looking at me, I assumed the answer was many.

I looked back at the ring, still with my nuts hanging out as Chubby had Daddy in an upside down bearhug, pressing Daddy's face into his covered crotch as he sucked Daddy's girthy 5 inch cock. Daddy didn't last long as he exploded into Chubby's mouth and the ref blew the whistle. The match was over but since the next match wasn't for another few minutes while the ref and admins added the score of the match to the leaderboard, Chubby still had Daddy at his mercy for a couple extra minutes.

Chubby decided to punish Daddy by PILEDRIVING him straight into the mat, Daddy laid dazed, still in a stupor since cumming and being dropped on his head. Chubby rolled Daddy over onto his stomach and raised Daddy's legs into a nasty BOSTON CRAB, sitting on Daddys back and stretching Daddy some more. 

Eventually, the ref cleared the two off the mat, Chubby appearing to go take a seat in the bleachers, and Daddy wandering off to the bathroom. 

It was time. My match was up next and I was determined to win, remembering my strat of overpower and jerk, I stepped into the ring and saw my opponent, he was not unlike Chubby, but a bit shorter at 6'2" and not as fat, but the real behemoth was in his crotch area, I couldn't really make out the shaft, but it looked like his balls were double the size of anyone elses I had seen so far. His singlet was already puffed out and sagging due to this, with his shaft falling out a little down his right leg.

"Oh buddy, you got a little accident there" He said pointing at my exposed jewels.

"Ahaha so do you" I replied, staring at his shaft as it started growing more.

"Here let me fix you up" He kneeled down and grabbed hold of my junk, tucking it back inside my singlet before giving it a little kiss and patting it with his hand. 

'Sweet' I thought to myself, this guy seems totally submissive, this might be an easy win after all if he rolls over for me.

"You mind being a good sport and fixing me up too? Don't want to start the match at a disadvantage" He smiled warmly, and my heart melted a little. I should have known he was a Trickster from the beginning but I couldn't help myself, a chance to get close to his crotch plus he did fix me up.

I kneeled down and leaned into his crotch, reaching out to grab his shaft, I didn't even notice him nodding to the ref to start the match. A whistle blew and before I could react, he grabbed my head, pulled his singlet forward and stuffed me inside with his crotch. I was stunned, man musk filled my senses, I scambled my arms out but he took hold of them, both in one hand, his hand felt massive around my wrists whilst the other kept my head steady inside of his singlet.

The Trickster laughed "Fell for the oldest trick in the book, silly jobber, now you can stay there for a little bit while my scent floods your senses, soon you will be begging to bend over for me and bounce on my cock" With that, he stepped forward, tucking my shoulders between his legs in a STANDING HEADSCISSORS, I was truly trapped, his balls and shaft were pressed against my face, he even pushed my head around and I felt the precum start dribbling onto my forehead. Luckily, none of this was enough to make me tap so I knew he would release me eventually but he was right, I was already tempted to just give up and let him plow me with that big fat cock of his and dump his heavy balls into my ass. I needed to get out of this hold....

I had an idea, if I could threaten to make him cum by sucking him off and then dive off his cock as he was going to burst, I would still get the win. A humiliating win but a win all the same, I tilted my head as much as I could and let his shaft fall into my mouth before wrapping my lips around it and sucked as hard as I could.

"Oh ho ho, good boy, learning his place is on my cock already" He patted my head through his singlet, unfortunately, I couldn't really get good head motions since he was still holding my neck hostage in his legs, but I wrapped my arms around him and starting massaging his ass, hoping to accelerate the process.

"I like the idea, make me cum before I can fuck you senseless, here let me help you out" He grabbed both sides of my head and pushed me down further onto his cock, making me deepthroat all 7 inches. My lack of gag reflex was helping me not to panic and choke, which is exactly what he wanted, if I panicked now, he would release from the hold and totally dominate me. But why would the Trickster admit to knowing my plan unless he himself had a plan? 

That's when I felt him stop thrusting for a second, I was confused, kneeling there with 7 inches of cock in my throat, I could feel him slowly patting my head softly through the material of his singlet, it felt kind of... nice. My body relaxed a little as his man musk invaded my senses once more. It felt like an eternity of waiting, as he kept stroking my hair, relaxing me even further.

After a while, I relaxed myself a little too much and, like a tiger jumping on his prey, he snapped forward, bending himself over and wrapping his arms around my waist and lifting me off the ground, I was only suspended in the air for a moment, legs kicking out before he PILEDRIVERED me into the floor, the motion was smooth, as if practiced a hundred times combined with his cock slipping out of my mouth, the influx of air and head trauma dazed me, leaving me stunned on the floor, gasping for air and clutching my head as I groaned in pain.

"Now let's see what my prize looks like" He chuckled to himself as he quickly pounced on me, trapping me on the floor as he pulled down the straps of my singlet, rolling me around with ease to yank it all the way off. Another practiced move I'm sure, he pushed me onto my stomach, exposing my hairless ass to him and the audience.

"Phew, how'd you know I like my twinks perfectly shaved clean?" He grabbed my cheeks roughly and split them apart, I don't know when it happened but he was also naked, rubbing his thick, long shaft up and down my crack, coating my hole in my own spit and saliva. 

I was slowly coming to, becoming less dazed and realising my situation, right now he didn't have me pinned or anything, he was just teasing me but once he was fucking me hard, he could hook my leg or chicken wing me and I wouldn't be able to escape the pounding. I would lose. Now was my only chance, if I pushed myself away from him and scrambled to my feet, the fight would basically reset, I would have suffered intense humiliation but I would be able to win. 

I had to time it perfectly though, if he smelled a plan forming he would stop his teasing and focus on pinning me again, I waited as he used my ass cheeks to jerk himself a little bit, I waited as he slapped me with his heavy sack, I waited as I saw the audience all touching themselves as my humiliation until finally I felt him adjust his cock and press his mushroom head against my hole.

The pressure was almost too good, I nearly threw my hips back onto his cock but I perservered. This was it, when he went to penetrate me, I would push off with my legs and turn this match on its head. I felt him push his hips into me and I braced my right leg and lunge-

SMACK SMACK SMACK

THREE HARD SPANKS crashed into my right cheek and I writhed in pain, clutching my ass, all momentum for my lunge lost as I curled up, trying to protect my poor cheeks from the assault.

"Tsk tsk, and here I was going to go easy on you but trying to outsmart ME? I knew you were just waiting for a moment to reset the match, why do you think I humiliated you for so long? I knew you were just going to take it like a good little boy until I went to fuck you like a proper man and then try and escape" He grabbed my legs as he spoke and dragged me back to him, this time rolling me over onto my back.

"Now I'm going to have to punish you, and treat you like the jobber trash you are" He pushed my knees into my chest, pulled my arms through and swung my legs over his shoulders, exposing my ass to him once more and trapping me in the missionary position like a pretzel. 

It was over, I was out of gas and even if I could fight back, he had me balled up, I was practically a fleshlight to him at this point. I could hear chanting from the audience. FUCK HIS ASS, BREED HIM and BREAK HIM IN HALF were amongst the most common phrases.

"mm, how does that sound my little slut? want your new master to breed you and fill you full of his cum?" This time, he didn't hesitate, all the spit, saliva and sweat in my ass and on his cock was enough for him to force all 7 inches of his beautiful cock into me at once, his balls slapped against my ass as he started jackhammering me. One of his hands grabbed my cock and stroked me.

"There's no such thing as a double victory in this place, but nothing makes me feel more like a king than making my opponent cum his little twink brains out while I pump him full of my load." He wasn't wrong, I couldn't last much longer, his scent, his cock, it was all overloading my senses and I was approaching orgasm rapidly. "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"

He grunted hard as I moaned loudly, my load shooting out of my cock, covering my chest and even some of my face in my own spunk. He slammed into me deep as his dick pulsed, filling me to the brim with his own load. He held me there, cock inside of me for a bit as he scooped up a bit of my own cum and pushed it into my mouth, making me taste myself.

The bell rung as the audience cheered and he slowly extracted himself from me, taking some of his cum with him as I could feel it leak out of my and down my crack. He walked away, leaving me there all bundled up as the ref came over to unfurl me and help me down from the ring. 

I limped my way through the crowd towards the bathroom, everyone taking the chance to to either squeeze my cock, slaps my nuts or give my ass a quick spank. I had been marked as a jobber and it was going to take a lot of effort to regain my image. At some point someone handed me back my singlet, I noticed it had a lot more cum on it than I remember as I finally made it to the bathroom to rinse myself down and push the loads of cum out of my ass.

I put my singlet back on and made my way out of the building, knowing I would be back here next week for more matches and hopefully... to win.


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