The Bet

by Caliban

8 Apr 2020 21457 readers Score 9.1 (463 votes) PDF Mobi ePub Txt


At school, I was on the wrestling squad. I was stocky and well-built. Apart from wrestling, I also dabbled in martial arts and boxing. The latter was not my forte and didn’t come to me naturally, because my foot and hand speed were never quite up to scratch. But when it came to grappling, I was able to hold my own.

I was also not the greatest student and settled for a trade after leaving high school. I chose the electrical route. Two years after finishing school, I had completed my trade and I got a job with a wonderful man named Frankie. He was a real champ and I loved working for him.

Sexually, I was straight. My love life, however, wasn’t exactly stellar at this time. I always seemed to attract needy girls and after a short while their oppressive clinging got on my tits.

Naturally, like most guys, I had participated in circle jerks with my buddies as a teenager, but that’s where it ended. On one occasion, one of the newcomers to our group even offered to blow us. I went with the flow and actually, it wasn’t too bad, in fact, it was very memorable. The ‘newbie’ was a formidable cock sucker! I wasn’t homophobic and had always believed in the old saying; ‘live and let live.’

In the industrial complex where Frankie’s business was located, we had a gym. The gym was well organized and had all the equipment one needed. It was a rough all-male establishment that mainly focussed on MMA. Many of the guys at the gym participated in the amateur fighting and once a month, we had our own in-house tournament, which was a great deal of fun.

The guys were all tough and a smell of male odour always permeated the gym. They were mostly a nice bunch of guys, except for one individual whom I really didn’t care for. He was known as Fast Hands Freddy.

Freddy was a paramedic. He was lanky and ugly and a real show-off. He was one of those guys with a huge cock who loved parading around the locker room and shower area, showing off his pride and joy. In all fairness, he did have the biggest uncut cock I had ever seen.

The thing that really irked me about Freddy was that he always referred to me as Rosie. My actual name was Ross. I wasn’t the only one that had to endure his ribbing and he always had an array of girl’s names, for all the younger guys at the gym.

Annoying Freddy constantly fiddled with his crotch, whether clothed or naked. At any mention by one of the guys at the gym citing a previous evening’s sexual encounter, Freddy would flap his dick about and brag, “Yes, but what would your girlfriend have thought about this?”

Our monthly tournaments were always held on a Friday evening, and Dec, the gym owner, always took it upon himself to arrange all the contests.

On a Monday prior to the next tournament, Dec asked me if I was ready for my first fight. Figuring, what the hell, I answered, “Sure.”

The list of match-ups was then always posted on the notice board, on Tuesdays.

After arriving at the gym on Tuesday my eyes scanned the list and I would be in the last fight. My heart then sank when I saw my opponent’s name; Freddy.

Later in the locker-room, Freddy stood before me and asked, “Are you ready for your butt kicking on Friday, Rosie?”

I then dismissively walked passed him before replying, “Whatever.”

The following evening, I again had to endure his taunting and again, I simply ignored him.

On Thursday evening, I arrived at the gym late due to a major job that I had to complete that day. By the time I was busy on my circuit the only three people left at the gym where Freddy, Dec, and myself. I then heard and saw Dec ask Freddy if he would lock up the place, before tossing the keys to him and saying, “Leave the keys in the usual place.”

Upon entering the locker-room later, I saw Freddy in his birthday suit, as usual. As I sat on the bench he then stood before me.

“You’re going down tomorrow, Rosie,” he said with a smirk on his face.

“Well, what if I beat you?” I countered.

“No chance!” he stated emphatically, before continuing, “But, why don’t we take a bet on the outcome?”

“I don’t bet Freddy, I earn too little money as it is,” I replied.

“It doesn’t have to be for money,” Freddy answered, nonchalantly shrugging.

“Actually, I’d rather not,” I retorted, with contempt.

Freddy then began making the clucking sound of a chicken, before asking, “Don’t have any self-belief, Rosie?”

“Yes, I do!” I shot back, in an irritated tone.

Again the squawking began, getting louder and louder.

“Okay, fuck, I take a bet with you,” I exasperatedly replied.

“Cool,” he said, before calculatingly resuming, “If I win, I’ll get to fuck your arse, and if you win you can fuck my arse.”

His disgusting wager was totally beyond my comprehension. After observing him disbelievingly for a moment, I replied, “That won’t work for me because I really don’t want to fuck you, and besides, I’m not fucking gay!”

“Well, what do you drink?” Freddy asked as if my comment had completely bypassed him.

“Whiskey, why do you ask?” I replied frowning.

“Well, if you beat me I’ll buy you a bottle of whiskey,” he suggested.

“Okay, so whiskey it is, the winner gets a bottle of whiskey from the loser,” I concluded, hoping that the matter had now been put to bed.

“Oh, no… buddy, you’ll get the whiskey… but I still get to fuck you if I win,” he replied, with an impish look on his face.

I just stared at him in total disbelief.

Nonchalantly, he then resumed, “If you have self-belief, then the bet must be meaningful.”

“Then I’d rather miss out on this bet,” I responded, trying to dismiss the matter entirely.

The squawking from Freddy now escalated to a manic level. I was really becoming annoyed and irrational, and before I could think properly my mouth trumped my brain.

“Alright,” I shouted, “I’ll take your fucking bet!”

Freddy then extended his right hand, with a self-satisfied look on his face.

After I got home, I assured myself that the bet was simply a humiliation ploy by Freddy. After all, with all his revelations about fucking and eating pussy, I placated myself with the fact that he wouldn’t follow through and simply humiliate me by telling the other guys about the ridiculous bet.

The following evening, the fights went according to schedule and there were one or two really great contests. At around ten p.m. our fight was announced.

The first round was even, despite a few solid body blows that I took from him. Round two followed the same pattern and I was amazed by Freddy’s grappling skills. With thirty seconds to go in round two, however, I got a solid blow to my right eye that stunned me somewhat, but when the second blow connected with my chin, I went down like a sack of potatoes.

All I could remember after that was waking up in the locker room. I had been placed on a towel on a narrow slatted bench. The world around me then faded once more.

When I next awoke I was naked, and Freddie was seated behind my head rubbing my eye.

After fully opening my eyes, I heard him say, “Relax, Rosie, you’re going to have a bit of a shiner tomorrow, but this cream is incredible and in a day or two you will be as pretty as you always were.”

Freddy’s massaging now moved to my jaw, where he had also solidly connected me.

“It’s really okay, Freddy,” I stated, “I’m actually feeling fine.” But he was having none of it and kept pushing my head down. “I’m really okay,” I again repeated.

With a stern look on his face, he said “Everyone has left and I have locked the front door, and switched the lights off in the gym. So, just relax.”

“I’m really fine,” I retorted once more.

“Are you forgetting about our bet, Ross?” he asked, using my proper name for the very first time.

“Freddy, I knew that you were kidding… Okay, so I’ll buy you two bottles of whiskey tomorrow,” I nervously replied.

“I don’t want a case of fucking whiskey,” he snapped, “I want your arse.” And for the first time, I actually began to believe that the bet may’ve been serious.

“Please, Freddy,” I implored, “Please… I really don’t want to be fucked by you or anyone. Please, just give me a break.” I begged.

“Are you a man of your word…?” he asked. After a sustained silence, he then bellowed, “Are you a fuckin’ man of your word? …You lost the bet, now take the fuckin’ shame!”

I was still feeling very woozy and weak and knew that I would not be able to stand up to him.

“Pleaaaase,” I begged.

Getting up, Freddy moved around me, before turning my body onto my stomach.

“No Freddy, please,” was all I could manage say, still very dazed at this point. Ignoring me, he pushed my legs forward on either side of the bench and wedged himself in behind me.

“Relax, boy, the more you resist, the worse it will be,” he commanded.

Expecting the worst to follow with him seated behind me, I was surprised when he began massaging my back. Pushing his thumbs up the middle of my back, he opened his hands to draw his fingers slowly downward. As he continued doing this over and over, it actually began to feel awesome. But, as my hopes started to rise I felt one, then two fingers begin to caress my butt cheeks.

“I have wanted this arse from the first time I saw it,” Freddy lustfully uttered. “Now, I’m going to fuck it,” he concluded in a growl.

As my body stiffened in protest, I felt an almighty slap on my arse. “I want you to enjoy this Ross. The more you fight me, the more it will hurt,” he proclaimed, spreading my cheeks.

Next, I felt his fat pole begin to move between my arse-crack. As he slid his knob to and fro, I felt a moistness begin to develop. With his hands firmly securing my back, his massive knob started nudging my arse lips, demanding entry.

“Nooo… pleaaaase,” was all I could manage.

Freddy, however, was determined to claim his prize acting like a sea otter that had just come across a beautiful pink starfish. As his dick delved ever deeper, my pleas were trumped by his groans of satisfaction.

“You are just as tight as I had hoped,” he hornily grunted.

“Ooooh,” he then exclaimed lustfully as my manhole succumbed completely to his infiltration. “This pussy of yours is even better than I had dreamed about.”

What astonished me was that after a very short spell of discomfort my cock went rock hard, and his dick was stimulating me in a way that I had never imagined was possible.

Oh fuck,’ I disbelievingly thought, ‘why is this turning me on?

When he lifted my torso upward encasing my body, as his right hand took hold of my rigid dick I was overcome with shame as he sniggered.

With his arms around me, I was pawed before Freddy’s thrusting began in earnest. On and on he pounded into me for the next twenty minutes, growling with pleasure as he licked and kissed my neck, while his right hand continued to tug on my dick. I felt like I was in a trance as I totally became subjugated by him.

“Does this feel good Ross?” he asked still sniggering. But I did not answer.

“Oh fuck, I’m getting close,” I cried out soon after, in a state of delirious ecstasy.

Freddy then immediately let go of my cock and after pushing me down flat on my stomach, he pushed his arms under my shoulders and cupped the back of my head in his two hands. As my arms flopped about in the air beside me, he asked, “Tell me how much you love my knob in your arse?” I again didn’t answer.

“I’ll keep fucking until you show some passion, Ross… and I can go on all night,” Freddy growled.

As he kept banging into me I still remained silent.

As he now really began to thump my arse, I was so overcome with ecstasy I eventually, I yelped, “Okay, I love your cock… but I really need to cum now… pleaaase, Freddy,” I begged, overwhelmed by horniness.

Freddy immediately released my head and after he lifted my torso, we continued as before. Not long after, I finally shot the greatest load of my life.

Next, my body was pushed down before Freddy went ballistic as he slammed my hole frenziedly. I was also totally amazed that my knob remained rock-hard as he flooded my backside with spunk.

After we dressed quietly afterward, as we were about to leave the locker-room, he pushed me up against the wall and fervently began kissing me. I tried to fight him off I kept protesting that I wasn’t a faggot. But finally, with me still being woozy, I simply capitulated to his ardour.

When we got to the parking area, Freddy had a strangely affectionate look in his eyes. “Please come home with me tonight. I know the bets over, but I really need to monitor that you are really okay,” he literally begged me.

With my mind racing, I was totally confuse and didn’t know how to respond. Freddy again then repeated, “Please, Ross.” I simply nodded yes.

After we exited the gym he told me that we could collect my pick-up the following morning.

Driving home, my mind kept spinning.

What the fuck am I doing?’ I thought, and to my amazement I was again rock-hard by the time we reached Freddy’s home.

Within a minute after our arrival we were in his bedroom, before Freddy began feverishly undressing us. Little did I realize at this point, that a sex manic had now taken complete control of me.

An hour later I passed out from sheer exhaustion. Goodness knows if he continued to use my body after that. When I awoke the following morning, however, I was flat on my stomach and having the hell humped out of me once again.

That day, I was overcome by remorse as I pondered, ‘For Fuck sake, I had sex with a man and I actually enjoyed it.

The following week I avoided the gym. It was a week of strife me. I couldn’t fathom why I had enjoyed sex with another man. It was like Pandora’s Box had been opened and I definitely felt uneasy with the outcome. Each night I tossed and turned in my bed, thinking about Freddy. It was as if a spell had been cast over me and I was unable to break free of my mental incarceration.

On Friday, Dec popped in at Frankie’s place to see if I was okay. I assured him I was fine and would be back in the gym, that evening.

Arriving at the gym later, I was relieved to find that Freddy wasn’t there. By the time I finished my circuit most people had left. I wanted to spend some time in the steam room and offered to lockup for Dec. After everyone had left, I locked the front door and switched off the lights.

I entered the steam room and relaxed. Ten minutes later I almost shat myself when the steam room door opened and I saw Freddy.

“What the fuck?” I asked. “How did you get in?”

“Dec gave me my own set of keys this week,” he answered, before continuing, “We need to talk Ross.”

“Freddy, I lost the bet and took the punishment. Nothing more needs to be said. Fuck it, I’m straight,” I fervidly stated.

“Bull shit! You loved me fucking you,” Freddy countered.

“No, I didn’t,” I shot back.

“That’s not what your cock was telling me, Ross,” he challenged.

I sat dumbfounded. I then got up, announcing that it was time for me to be on my way. Freddy blocked my path as his hands clamped onto my arms.

“Did you dream about my knob this week?” he asked.

“No,” I hastily retorted.

Moving his hand down, Freddy gripped hold of my erect dick. “Your cock isn’t a liar like you are,” he said sniggering.

Pushing my body against the wall, his lips began searching for my mouth. I swayed my head to and fro but as his grip intensified, as my mouth was conquered. As we kissed he rubbed his fat pole into my body.

Turning my body he pushed my torso downward. As I leaned forward with my hands on the built-in seat, I felt a prodding at my arse lips. Freddy’s entry was slow but firm.

Why does this guy have such control over me?’ I thought, ‘but, fuck, it feels so great.

As Freddy’s unhurried thrusting got underway, I was again feeling the sexual gratification I had experienced the week before. All former restraint I had melted and I began groaning like a sex-starved slut.

“Talk to me baby, tell daddy how good this feels,” Freddy grunted.

“Aaaaah, yes, fuck me, fuck me,” I intoned over and over again.

A short while later, Freddy pulled my torso up, before again turning my body and pushing me to my knees. “Time to taste your daddy’s spunk,” he announced.

I began tugging on Freddy’s knob and as he got close, he slapped my hand away and pushed his dick into my mouth. The eruption was hectic, as he sprayed all over my face, before returning to my mouth. I cannot say the taste of his spunk was my favourite taste, but I was so horny that I swallowed it like a starving man.

Pulling my body up afterward, Freddy lapped the residue off my face.

“You’re coming home with me,” he announced, before commanding, “ Now let’s get going.”

After rushing to the bedroom after our arrival, we were soon rewriting the Karma Sutra. On this occasion, however, my participation was far more animated. For the next couple of hours, there was not a sexual position that was left untried. Having gotten over my man-love apprehension, our level of affection continued to evolve and escalate.

The following morning when I announced that I needed to be on my way, Freddy smiled, informing me that he would only allow me leave the following evening.

My ringmaster had spoken, and I knew that from now on I would be his full-time bitch.

by Caliban

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