A Bet’s A Bet

A Bet’s A Bet

“It’s time to wake up now.”
With just those six words, I regained the ability to open my eyes. Regained? I guess that’s not the right word. I’d only just dozed off—nothing more.
“Well, how do you feel?” The hypnotist grinned at me. I didn’t see why he was grinning, though. He was a friend of mine. His name was Kyle and he liked to think he was a master when it came to hypnosis. I guess in a sense he was. I did get into a trance, after all—well, I did if that’s what you call falling asleep from the weight of sheer boredom.
“No different, Ky. You suck at this.” I really didn’t feel any different. At that point I almost considered letting him call off the bet. You see, we had a bet going. He said he could turn me gay without making me less attracted to women—he thought he could make gay sex better than straight sex for me. I thought hypnosis was all bullshit, so I figured what the hell; it’d be an easy hundred dollars if nothing more.
“No different? Well, then, let’s try this... faggot!” Right as he shouted that word, my right hand shot up in the air. I looked at it with what anybody who wasn’t in my situation would consider a hilarious expression.
“What the hell!? How did you do that? Is that—am I stuck like this?” Kyle was clearly enjoying my expression of horror which lasted even after my hand was able to go down again.
“Don’t worry, that trigger only works for my voice. Think of it as your way of telling me just what a faggot—”my hand shot up again“— you are. I hope you’re ready to give me that hundred bucks.” After that little show I considered begging him to let me off the bet right then and there, but a bet’s a bet. They say hypnosis can’t make you do anything you don’t want to do so I managed to convince myself that I could still win it.
“Alright Ky, you made me raise my fuckin’ hand. We’ll see how you’re feeling in a couple weeks when your wallet’s a hundred bucks lighter.” At that point it was time to head home. It was pretty late and I didn’t want to get caught in traffic. I grabbed my jacket and was about to leave the house when Ky walked up to me holding a plain cardboard box.
“Here, take this box with you.”
“What’s in it?
“It’s part of the hypnosis. Don’t open it up until I tell you. ”
“Alright, sure, whatever. A deal’s a deal. I’ll do whatever you ask until next week’s up.”
Box in hand I left his apartment and took the elevator to the first floor. It was raining outside but my car was in the parking garage next door. After I was safely inside it, I got curious about what he’d put in the box. I promised him I wouldn’t open it—and I’m not the type to go back on his word—but I didn’t say I wouldn’t try to puzzle it out some other way. I gave it a shake, and there was a dull thud as whatever was inside of it moved around.
It was longer than it was wide, and made out of some kind of rubber. There were also a couple of other things in there. Some kind of can or something, and a smaller metal object. There might have been some other things in there but I couldn’t think of any way of figuring it out without breaking my promise.
I sighed and set the box aside, then buckled in for a fairly uneventful drive home through the rain. When I got inside my house I checked my cell phone. I’d forgotten that I turned it on silent when I was being “hypnotized” by Kyle, so I turned the ring tone back on and set it aside.
After doing the usual house stuff—cleaning, cooking dinner, watching TV, and what-have-you—I decided to sit down and watch some porn. I got myself comfortable in bed and powered up my computer—it’s set up right next to bed—and navigated to my favorite site, xhamster.com. It was only seconds before I started stroking my cock.
I’m reasonably proud of my cock. It’s six-and-a-half inches—seven on a good day—with a little bit of a curve to the left. At the base I had thick pubic hair which I did little to trim or maintain. I kind of liked the way it made me look. Manly—powerful.
While watching yet another video of some silicone monstrosity taking dicks up her ass like a champ, I noticed something was wrong. I wasn’t really relating to the man doing the pounding. In fact I was kind of fantasizing about what the girl was feeling. Believe me, when you’re straight as an arrow that’s a terrifying realization.
After a few minutes—long enough for my cock to fully deflate—I worked up the courage to test myself. I clicked over to some gay porn, picked at random, and waited for the video to load up. My heart was beating like shoes in a dryer at that point, but I calmed down a bit when the kissing and stripping didn’t do anything to rouse my limp dick.
Needless to say I was pretty damn shocked at what happened when one of the men on the screen pulled the other’s cock out and started sucking. My dick was standing at attention almost instantly and it was the hardest erection I’ve ever had. That was enough for me. I closed out the window and decided to go to sleep. It was an odd feeling, being sexually frustrated and yet disgusted with myself.
I checked my cell phone the next day, after work. Lo and behold, Ky had left me a message.
6:32PM Kyle Anderson: Hypno time. My place. Faggot!
My hand shot up in the air right as I read that—luckily the parking garage was deserted. It took me a few seconds to force my hand back down. And with that a night of masturbation and soul searching had been replaced with a night of hypnotism that I feared would worsen my decline. A bet’s a bet, though. God damnit, I thought.
It was about seven thirty when I reached his apartment. Weirdly enough, I can’t really remember what happened once I got in the door. I only really remember what happened after I got home that night.
My phone vibrated and the screen flashed with a message from Ky.
9:47 Kyle Anderson: Listen up queer, it’s time for you to open the box. There’s a note inside, it will tell you what you need to do.
I’d been damn curious about what was in the box. Finally it was my chance to figure out what was in there. Needless to say my curiosity died—or at least masculinity dictates that I say it did—when I opened it to find a flesh colored dildo—almost exactly the size of my own dick—as well as some lube, a can of womens’ shaving cream with a pink razor, a rainbow colored cock ring and some panties. And the note...


Nick,
I’m glad you finally got to the stage of opening Pandora’s box. Well, that’s what I like to call it at least. If you opened this without me telling you to I’m going to be pretty goddamn pissed and you’re going to be giving me my hundred bucks.
Anyways, it’s time for you to start experiencing what it’s like to be gay. I’m not going to touch your attraction to women; that’s for you to figure out. I am going to give you a little taste of what you’re missing though. Leave the dildo and the panties, those are for another time. I want you to shave your crotch. Balls, ass, everything. I don’t want to see a hair anywhere down there.
You’re also going to wear that cockring from now on. When you have everything groomed and the cockring on, I want you to take a picture of yourself bent over with your ass cheeks spread. Then you’re going to jack off.

-Kyle

When I first read the note, I was incredulous. Did he actually think he was going to make me do that stuff? It was only after my body started moving to carry out the actions prescribed that I got worried. I watched, detached, as I looked up a guide for how to shave my pubes and, after trimming myself as closely as I dared, slathered the sweet-smelling shaving cream on my unmentionables and slowly but surely shaved all the hair away.
When I was done, my crotch was as smooth as the day I was born and the cool, tingly sensation of the shaving cream was almost arousing. I automatically put the cockring on and went into my bedroom. I bent over on my bed in front of my computer, and used the webcam to take several pictures of myself with my ass cheeks spread.
After emailing them to Kyle, I jacked myself off. The ring made my cock bigger than it had ever been before, and thick veins bulged outwards in places where my cock was once smooth. I came in less than two minutes, and sprayed cum all over my chest. Believe me, that was not a fun mess to clean up. After I was done and the post-masturbatory haze had washed over me I was taken by a sense of anger. The game had gone far enough. I’d give Kyle his money but I wasn’t going to risk being turned into some kind of gay fucktoy robot. That was when I saw the email alert flashing on the screen.
After reading what it said I was almost in a state of shock. Kyle said if I didn’t keep going with the hypnosis until the end of the bet he’d send my pictures to everyone I knew. I was stupid enough to include my face in one of them, so I knew I was pretty fucked. He did say that right after the bet was over he’d let me watch him delete them. I suppose the only consolation I could give my past self if I were there is that eventually I would come to love the fucking.
The next couple hypnosis sessions passed with few notable events. Aside from making me keep up on the grooming of my pubic hair, Kyle didn’t tell me what he was doing to me while I was under. He did forbid me from watching porn though. I’d agreed to his terms at the beginning of the bet, and I didn’t want to get humiliated in front of my friends and family, so I did as he asked and avoided porn like the plague.
By the third day my bare cock was aching in its desire for pleasure. The problem was whenever my hormone-flushed brain tried to think of some fantasy, I couldn’t think of much other than gay sex. The gay thoughts did help with my erections though. Whenever I thought of something gay my cock lost any semblance of hardness. I was having some problems with precum though; there were times during those few days where I would go to the bathroom and pull down my pants only to find my ringed cock and balls slick and sticky.
It was on the fourth day that I received an email from Kyle outside of our normal, hypnotic meetings, which I have trouble remembering. I’ve pasted what he sent below.

Hey Nick
It’s time for you to take it to the next level. I’m sure you know by now that manly men have hair on their balls and assholes, because they don’t need to be pretty down there to please their lovers. You can’t have hair on your asshole though. Around men you only care about their cocks, and why would a cock go into your asshole if it’s not pretty? If you wanted to put your dick in something you would find a woman, but you need something hard and thick in your own tight little hole. That’s why you wear the rainbow cockring after all, to make your dick look cute for all the guys. It’s not like they want it to look manly or strong. In fact it makes you uncomfortable when you’re around a man and he sees that your dick is bigger than his. That’s why you can’t get hard whenever you’re looking at a man. You want him to focus on fucking your ass, not your cock. In fact, when you see a man naked your dick goes limp and you get a burning feeling in your ass. The only way to relieve it is to put something in there. If you rub that special spot in there enough, your dick might get just hard enough to let out a stream of precum. It’ll feel amazing, but you’re not going to be fucking any men with that cock, no matter how they might beg you to. Your cock is for women. Your ass is for men. From now on I want you to wear panties, the first pair is in your box. I’ll give you a new pair to wear every time you come for a hypnosis session. I want you to try to masturbate to gay porn tonight, but you can’t touch your ass.
-Kyle
I almost thought it was funny the way he was trying to convince me that his hypnosis was having the effect he wanted it to have on me. If he wanted me to be attracted to men, my dick would be getting hard. I figured I’d humor him—see if I felt any attraction to men at all. After putting on the panties, I loaded up xhamster and picked a video. I made sure it was one about the largest, most powerful looking cock I could find going into someone’s ass.
At first the video had no effect, as I watched the larger man overpower and tie the smaller one up. It was when the large man pulled his penis out, ten glorious inches nested in a bed of dark curly pubic hairs, that I began paying rapt attention. The younger man who was tied in a very compromising position, barely more than a boy to be honest, paid some token pleas for mercy. His soft cock dangled above his own mouth. The pleas came to an end as the large man slowly slid his thick member into the younger’s ass.
At that point I pulled aside the panties and tried to get myself to harden. No matter how harshly or gently I rubbed, though, I couldn’t get myself hard. It felt good, but I knew it wasn’t going to help me cum. To be honest, I looked more like a woman rubbing her clit than a man masturbating to porn. My own ass had a burning feeling in it, and I was desperate for relief, but I couldn’t bring myself to touch it. Several minutes of thrusting and moaning followed, before the most spectacular thing that I’ve ever seen in porn occurred.
The young man’s cock—which had slowly hardened throughout the film—began dripping cum onto his face and into his mouth. The large man kept fucking him as cum slowly poured out of his dick. His moaning had turned to frantic screaming of pleasure at that point. As the waterfall turned to a slow drip, the large man pulled his dick from his fucktoy’s ass and stroked himself a few times. He sprayed his semen all over the young man’s ass and balls, and then went to his knees and forced the young man to lick his softening cock clean of any remaining cum.
It was at about that point that the video ended, and I was left in the terrible state of being incredibly aroused and yet unable to get hard. My ass was burning, practically screaming at me to put something inside of it, but I couldn’t move a muscle to touch it. It took me a couple hours to calm down enough to get some sleep.
I slept in until eleven—thank god for national holidays—and was woken by a phone call. I looked at my cell; it was Kyle.
“How are you feeling? Sleep well?” That cocky, sarcastic voice... I used to like it.
“How well do you think I slept? What are you doing to me?” The words sounded indignant, but my heart wasn’t really in it. I was tired of fighting him and—I truly hated to say it—I was beginning to enjoy the feelings he was causing.
“I’m only doing what I said I’d do. I’m turning you gay. Do you think you can hold out for five more days, Nick?” Truth be told, I’d started doubting that I would win the bet at about the time when he had my body moving against my will.
“We’ll see, Ky.” It was hard to even be confrontational with him. His voice had already changed me so much.
“Yeah, I guess we will see. Faggot!” He hung up on me right as my hand shot up in the air. If I weren’t so sexually frustrated I would have probably done something stupid. As it stood I went about my day until about two o’clock, when he sent me a text message.
2:07 Kyle Anderson: Alright Nick, big day with the hypnosis planned. Get to my place by 3... and bring the dildo.
Redness shot to my face as I remembered the dildo, flesh colored and veiny, which I’d almost completely forgotten about. I wasn’t quite sure what he wanted to make me do with it, but I had my suspicions by that point. I grabbed the cardboard box which contained the dildo, and hopped in my car. It took me about forty five minutes to reach Kyle’s apartment complex, so I was hurrying a bit after I found a parking space in the garage. When I stopped for a moment to think, I couldn’t figure out why I was hurrying to meet the destruction of my sexuality.
As usual I have no memory of several hours after I got in the door of Kyle’s house, but I will tell you that my asshole felt sore afterwards, even though the sexual frustration still remained. However, when I got home that night something amazing happened. I was frustrated yet resigned to a fifth day without cumming when I got a call on my phone. It was Kyle, and if he were with me when he said those words I would have sucked his dick on the spot. He wasn’t, though, so that came later.
“So Nick, you’re going to do a few things for me, but afterwards I’m going to give you a reward.” I was intrigued. Frankly I had no clue what the reward could be.
“What am I going to do for you, Kyle?”
“You’re going to shave yourself. All the body hair, gone. I don’t want anything below your eyebrows. Then you’re going to get your webcam, set it to record, and fuck yourself for me. I loosened you up today while I had you under, but I made sure not to let you cum.”
“Yes master,” I said before catching myself. Master? What the fu—but at that point my body had already begun its automated tasks. An hour later, I felt like I had been reborn. A fully shaved body is a beautiful thing. My skin felt soft, and the air washing over it gave me goosebumps. Simple, everyday things like the rub of my jeans against my panty-clad—although he had been moving me more towards thongs recently—ass were new sources of arousal.
Anyways, enough about the simple pleasures of a smooth body. After I was finished admiring my handiwork in the mirror, I set myself up comfortably on my bed. I was propped up, with my lower back against some pillows and my legs spread wide, giving full view of my asshole and cock. The thong barely covered my balls, in fact they hung out to either side. My asshole was clearly visible, with only the thin string of the thong covering a small part of it.
The feeling of the thong in between your butt cheeks, rubbing your asshole whenever you take a step can only be described as divine... but also incredibly, frustratingly arousing as I would later learn. But that was a problem for a different time.
I lifted the dildo with great reverence, and as I did the ever-present burning sensation in my asshole intensified. While I coated it in lube, I grinned inwardly—I finally had a way to relieve myself. Fantasy upon fantasy swarmed my mind as I pulled my thong aside and the dildo easily entered my asshole. When I felt the rubber balls slap against my butt, I held it there for a while. With the dildo stretching my insides, I tensed and relaxed my ass, reveling in the sensations. After a minute or so, however, that was no longer enough. I had to fuck myself. Slowly at first, and then with greater speed I slammed the dildo into my asshole. Eventually I was fucking myself so hard my hairless balls were bouncing up and down and my soft cock was swinging back and forth.
The orgasm—if that’s what that amazing, transcendent feeling could be called—came upon me in waves, and without notice. I didn’t even realize I was screaming until the climax had passed. Afterward, I laid there for several minutes enjoying the afterglow; my semen had drenched my balls and fallen to coat the base of the dildo that was still impaling my sore asshole.. I reached over to my computer and sent the video to Kyle. I removed the dildo from my ass and put it back in its box, then laid down in bed still covered with my own cum. It wasn’t long before I fell asleep. I’m sure you can imagine how uncomfortable it would be to be woken up in such a position.
...Which is exactly what happened, as I opened my eyes to see Kyle’s own. He grinned that cocky grin of his and told me to get up and take a shower. I automatically did as he commanded, and it wasn’t long before I found myself standing naked in front of him, bare body on display, with only my thong and the rainbow cockring for adornment.
“So, Nick, I think I’ve won the bet right?” At that point I’d be lying if I said he still had a ways to go.
“Yes, you won.” I found my wallet and pulled out a hundred dollar bill. “Here’s the money I owe you.” The old me would have tried to weasel out of it somehow, but I couldn’t fathom trying to trick Kyle.
“Thank you, Nick. I can think of a way for you to earn it back, though.” I thought I knew just what he had in mind. I licked my lips.
“And how would you have me do that?”
He unzipped his jeans and pulled out his already hard dick, which protruded from a thick nest of pubic hair—six inches, the old me would have been proud to know his dick was bigger. But I’m not the old me, and I’m glad that I can’t get hard anymore around men because then my cock would have been visibly bigger than his, and that would be very wrong. In fact, just the thought of my cock being bigger than his was enough to keep me soft.
“Suck it, Nick.” I instantly went to my knees in front of him, and took him into my mouth. I was surprised at how easily I did it, to be honest. I’d never tried deepthroating before, and unless he had been doing a lot more than I knew, just the hypnosis was enough to rid me of any semblance of a troublesome gag reflex.
The slurping went on for several minutes before he made me stop. By that point the burning in my ass had grown almost unbearable. “Let’s go somewhere more comfortable, why don’t we?” He led me to my couch, where he sat and spread his legs to give me easy access to his dick.
“Get back to it,” he said and I instantly resumed sucking his dick. Occasionally I’d pause to toy with the sensitive area under his head, or I would try to hold his dick inside my throat as long as possible, and swallow around him hoping the squeezing would feel good on his cock. That brought tears to my eyes, but I didn’t care. I just wanted his cum. It took several more minutes before he shot down my throat. Imagine my surprise when I felt a steady stream of cum dripping from my own cock, soaking through the thong and pooling on the floor between my knees. After a few moments of basking in the pleasure of it all, I looked up at him with a questioning look.
“Figured that the perfect bottom needs to enjoy more than just getting fucked.” He was clearly enjoying it almost as much as I was. As amazing as my orgasm had been, it was just that: an orgasm. I could have gotten that from fucking a girl. That did nothing for the burning in my asshole, the aching need for something to fill the space. After I spent a minute or so cleaning what little sperm escaped my mouth off of his cock, I felt him shove a couple of twenties into the waistband of my thong.
“Buuut... it’s time for the main course. I’m going to fuck you right here.” He made me turn around and sit on his lap. Before I sat down, he reached around and pulled my thong to the side so that my cock and balls could flop out. I sat slowly, wanting to enjoy every second of the first cock my heretofore virgin ass had received. When I finally felt my smooth balls resting on his rough, hairy sac, I was in heaven. He put his hands under my legs and made me bounce on his dick for a long time. Since he’d just cum it was going to be a while until he was ready to do so again, and I was prepared to enjoy every moment of it.
By the time he was bored of my bouncing, my legs were very tired. When he told me to get up and move to the bed, I did so shakily, and when he told me to bend over and go down on my hands and knees I did so gratefully. He fucked me, hard and deep, for several minutes. When his dick was pushing in, I relaxed my asshole completely. When he pulled out, I tightened on him, trying to make it as pleasurable for him as possible. My prostate was taking a beating and every once in a while some watery cum would shoot from my dick, accompanied by a wave of pleasure.
“Stop, Nick... I want you to look at me. Get on your back.” I was drunk on sexual energy at that point, and I quickly positioned myself on my back, propped up by pillows and with my ass hanging off the bed. He looked at me for a moment, my legs spread and bent at the knee, body hairless, cock limp and ringed, and then bent towards me. The top side of his rock hard dick pressed between my butt cheeks as he kissed me.
“I hope you’re enjoying this as much as I am,” he said as he pulled away to catch his breath. Whenever our lips touched it was like electricity coursing through my body. He kissed me again, more deeply, and our tongues rolled over each other in a carnal ballet. He pulled away and looked me in the eyes. “You know, I’ve always loved you... and I knew you were gay all along.” A small part of the old me was horrified by that, and I pulled him in for another kiss to stop him from continuing. He obliged for a moment, but then pulled away again. “Hypnosis can’t make you do anything you don’t want to do. You wanted this.”
Woah. That was a shocker, let me tell you. I was Nick, straight as an arrow, manly as hell, great cock and what-have-you, completely shaven and lying on my back with my legs curled around another man whose cock was pressing hard against my asshole, with my own dick lying limp. I stared at him for almost two minutes. That’s when he did the last thing I expected. “I’m giving you back your free will. It’s your choice now.”
It took me a moment to think. He’d shown me pleasure unimaginable, taken my free will, turned me into his own personal fucktoy... but then he gave me my freedom back. With that in mind, I knew what I had to do next. “Alright Ky, I’ve made my choice.” I paused, then reached for his dick. “Fuck me.” I guided him into my asshole, and at that point he knew what to do next.
We made slow, sensual love. When he finally came inside my ass, he set off a climax that had been building for what seemed like a liftetime. I felt all the pleasure in the world course through my body as spurt after spurt of sperm left my soft cock. By the time I was done, his own dick rested limp inside my asshole and our bellies were coated in sperm. We fell asleep like that, together.