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I Wouldn't Bet On It
"Fuck, fuck, damn, fuck! How is that even possible?" I groaned. "How does that fucktard get reelected?"
I finally had to turn off the TV. I felt sick watching the headline scrolling across the bottom of the screen, announcing that a multiply indicted, and convicted, criminal was just elected president for the second time!
What will the next four years look like? How bad will it have to get before I seriously consider moving to Canada? Will there be any room left in Canada?
My fellow Americans once again proudly failed to live up to their potential. What it would mean for the country scared me, but it was the next day before I remembered the one thing that should have been scaring me the most. The bet.
A little history.
I met my best friend Steven when we were juniors in high school. We hit it off right from the start. We had a mutual love of books and movies, and a twisted sense of humor. Even when one or both of us had girlfriends, we still always hung out together, on double dates or as an oblivious third wheel. That might explain why we never had girlfriends for very long.
There came a point where I was still dating and Steven was always the plus one. I didn't think much about it until one day when we had been hanging out, drinking, and he admitted that he was gay.
I remember responding with a grunted, "Hngh? I never would've guessed."
"You're not freaked out?" He asked.
"I guess not..." I answered, giving it some thought. "It doesn't really change anything."
"Oh. Cool. I was worried you might not want to be friends anymore."
I guess I understood why he had been worried. I'm pretty sure not everyone would have reacted the way I did. I just didn't see how it affected me and why it should stop us from hanging out.
"How did you think I'd react?" I asked.
Steven shrugged. "I imagined one of two options. The most likely was that you would lose your shit and kick me out."
"Sorry to disappoint you," I chuckled. "What was the other option."
He gave me a side-eye and grinned. "You might have confessed that you were also gay and secretly in love with me."
I laughed out loud. "Oh really?"
"Yeah, but I would have had to tell you that you aren't my type. Probably break your heart."
"You liar," I accused. "I am totally your type."
"You'd like to think so." He shrugged and smiled. "I guess we'll never know."
We left it there for the next couple years, though, typical for our friendship, one of us was always baiting the other one. He'd get in a funk about something, and I'd tell him that all he needed was the love of a good woman. And if my sex life was not going well, which was now more often than not, he would make offers like, "I could always rail you!" or "I bet you'd get laid more if you switched teams."
It was always good natured and goofy, but I'll admit there were a few times, when my balls were a darker shade of blue, that I wondered what it might be like. Still, there was no way anything would ever happen without some other motivating trigger. It just happened that the upcoming election provided the it.
"I've got bad news for you. That shat stain is going to win again," Steven grunted, while we were driving to get some dinner.
"Say what?" I asked, not sure what he was talking about.
The radio was on the news and Steven pointed out the talking heads were all certain that the democrats had a lock on the election.
"I think they're wrong," he said. "I think he's going to win."
"You want that grifter back in the white house?"
He scoffed. "Fuck no! I just think it's going to happen. People are that fucking stupid."
"I wouldn't bet on it," I argued.
"You said that the first time," he reminded me.
"Well, yeah," I agreed, "but now everyone saw how bad he fucked it up."
He shook his head. "Most of them already forgot, and a lot of them were too young back then to even know how bad he was."
"Well, I don't believe it will happen," I grunted.
"It will. I'm even willing to bet on it."
"You're loss. Okay, it's a bet," I agreed.
He shook his head again. "No... we need some real stakes."
"Fine. One hundred bucks," and then remembering my financial situation, "Or maybe just fifty.
"I don't want your fucking money. "
"Okay... then what do you want?"
He only thought about it for moment. "I really want to test whether you are straight."
"And how the fuck do you plan to do that?"
"If I'm right... you... need to let me blow you."
I laughed. "I got bad news for you," I told him. "I don't need to be gay to let some dude give me a blowjob. I just need to be able to turn out the lights."
"Fine. Be like that." He sighed. I thought that meant we were done but I was wrong. "Okay... If you lose... then we fuck."
"Whoa! I don't think so!"
"I thought you were sure you'll win?"
"I am," I agreed, still caught a bit off guard by his proposal. "But if I win, that's not really something I want. I'm not even sure I could get it up."
"You won't need to if I fuck you."
"Hah! Not likely."
"Then... if I win, we can flip a coin? Heads, I give you a blow job. Tails, I get to fuck you, and I'm fine with either."
"But what am I supposed to get when I win?"
"If you win... I... still fuck you, and you get the satisfaction of confirming that you are my type. Just think of how embarrassed I'll be?"
I laughed. "Nice try. It needs to be something that you don't want."
"Hmmm..." I think Steven was surprised I was still even considering the bet. "How about... if you win we trade cars?"
Steven was a computer nerd even back in high school, and that carried over into his career. By the time we were old enough to legally buy booze, Steven was already making close to six figures working on computer security for a variety of companies. One of his first purchases was 1968 Ford Mustang, which was my dream car. The only reason he bought it was because he knew it would make me envious.
Unlike Steven, I did not have any marketable skills, and I barely made enough to buy my very practical ten year old Hyundai. It get me back and forth to work.
"You aren't serious!"
"As a heart attack," he confirmed. "But that means you have to be serious too."
I knew what that meant. How confident was I that I would be right? Apparently, pretty damn confident. We even shook on it.
After getting over the initial shock of the election and about the same time I remembered the bet, the doorbell rang.
Hi Steven," I greeted him as I opened the door.
"How are you holding up?" He asked.
"I feel like someone killed my puppy." I answered. "It's like a hard hit to the gut."
"Yeah, for sure," he agreed. then getting right to the point, "But... speaking of a hit to the gut... we had a bet."
"Shit... yeah... I know... I just... I need you to give me some time to work up to that."
"If it had gone the other way, I was ready to make the car swap. I even brought the title."
"Well, yeah..." I grunted. "But to be totally honest... I really wasn't thinking I might lose."
He scolded me. "Are you trying to get out of it?"
"No! No..." I answered. "I just think... I may need to be drunk... or at least not totally depressed."
"There is nothing better for depression than good sex." he offered.
I challenged. "It may be good for you, but I'm pretty sure this will just make it worse for me."
"You want to bet on that?"
That made me chuckle. "No! I think I'm done betting... Maybe forever."
"You may still get lucky. We flip a coin and you might get a nice blowjob... or... I get up in that tasty ass."
"Tasty huh?"
I have to admit, I wasn't completely opposed to letting my buddy try blowing me. There were already a couple times when I was between girls that I had considered asking him if he might be willing and lately I was in a real slump with girls. I knew I could use the release. The alternative to that was a lot less welcome, but it was a coin flip, and I had to be due some good karma. "Fine, but I may need to turn out the lights when you blow me."
"If it's heads, I'll turn out the lights." He agreed. "If it's tails, I'm bringing in a spotlight."
"Whatever," I snarled, still feeling like I was due some good luck.
"Do you want to flip, or me?"
"I'll flip," I said, wanting what little control was left in this situation.
He pulled a few quarters from his pocket and I chose one. Then, after taking a deep breath, I flipped it up in the air and let it drop to the ground...
"We'll go slow," he quickly assured me. "And I promise I won't really go to town on your ass... unless you ask me to."
"Do we really have to do this now?" I asked.
"You know what will happen if we put it off."
I nodded. He was right. If enough time passed, I would have tried to laugh it off, but I also know I had already been looking at accessories for the Mustang. I had fully intended to collect if I won and I know he would have followed through. I owed him this.
"Do I need anything... for..."
"Nope, I've got everything we need right here," and he patted the small backpack he had slung over one shoulder. "This first part is going to seem weird, but it is for the best. I promise."
"Okay..." I questioned.
"Strip down and I'll explain as we go."
Reluctantly, I started peeling off clothing. To my surprise and confusion, Steven was making no effort to join me in that. He was still fully clothed and pulling stuff out of the bag.
Once I was naked, I just stood there, feeling really stupid. "Now what?"
He held up one of those bulb shaped nasal syringes.
"What's that for?" I asked, but I already had vague idea.
"First, we should clean up the playground," he told me. "This is mostly for you, since it's your first time. It's not usually bad, but sometimes shit does happen," he said with a wink. "We may not need this, but if we do, I promise you will appreciate it. Nothing messes up good sex quicker than churning mud."
I immediately had a mental image of what he was talking about, and I knew he was right. I wanted no part of that. Getting fucked was going to be bad enough.
"How do I use it?"
"I can help you with the syringe, but I'll leave you alone for the part that comes after that."
"Yeah... okay," I agreed.
Steven then sat on the toilet seat and patted his lap. "Get down here for your spanking young man!"
I felt my cheeks, both sets, warm with my blush, but I did what he asked and laid belly down across his legs. Thankfully, he was still clothed. If he was naked like me, and I had to stretch out, skin-on-skin, I am not sure I could have done it.
Steven didn't spank me, but he did give my ass cheek a soft pat with the flat of his hand. Then his hand rested on my buttocks and traveled the curve, almost caressing it. I shivered, and I couldn't decide if it was because I hated it or... something else. It was a bit of both.
His hand left me, and I saw he was putting some lubricant on the syringe. Then, when his hand returned, one lubed finger went straight to my pucker and eased inside.
"Ungh," I groaned.
"Don't be a baby," he scolded. "That didn't hurt."
He was right. It didn't hurt, but it was still concerning. This was private space, my fortress of poopitude, and all my alarms were flashing and blaring with an intruder alert. That said, His finger in my butt was more interesting than it was uncomfortable and I even felt a brief sense of loss when he pulled it out. Then it was immediately replaced with the slim stem of the bulb.
He had already filled the syringe with warm soapy water and as he squeezed it, I felt a rush of fluid flowing into my ass. It was going the wrong way and that was a new sensation for me. Luckily, the bulb didn't hold much liquid, so there wasn't an overflow risk, but I immediately felt a strong urge to go. Steven made me stay in place and hold it for a few seconds longer than I thought necessary.
"Okay," he finally accepted, pulling the syringe from my ass. "Get up and I'll leave you to it."
I gingerly stood, clenching my ass, but not really at risk of having an accident, though the need was becoming increasingly urgent. Steven walked out, closing the door behind him, and I lifted the toilet lid and plopped down on the seat. A second or two later, with immense relief, I let loose the flood.
Once it was out of me, I sat for a minute. Partly to make sure I was done, but also to put off what I knew was my very real fate. I finally stood and flushed the toilet and I was relieved to notice that it wasn't very messy. Steven had said it probably wouldn't be bad and it wasn't. I guess if we ever did it again, this butt flush stage might not be needed, but then... we would never do it again. I was confidant of that.
As I came out of the bathroom, I announced, "My pipes are clean!" And then came to an abrupt halt, when I saw Steven was waiting for me, buck naked.
I tried to remember if I had ever seen him naked before. We didn't share a PE class in school, and neither one of us went to a gym, so there was never really an opportunity. If there had been, I might not have made the bet.
"Holy fuck... You don't seriously think you're sticking that up my ass, do you?"
My best friend was only half hard and his pecker was already as big as mine would get at full erection. He wasn't like Johnny Wadd huge, but he was generously endowed, and I had a very virgin, and very reluctant, ass on the line.
"Thanks!" he crowed, clearly hearing a compliment and ignoring the concern in my statement.
"I'm serious," I told him. "I don't know how the hell you expect me to take that... especially on my first try."
"Isn't that sweet," he said, confusing me even more. "You're already thinking about doing it again."
I could see by his grin, that he was kidding.
He continued. "Second time, third time, or after a dozen times... it might get easier, but I promise you can do this even on the first try. We just have to go slow and not force it."
"I'm feeling pretty much forced already," I accused.
"You didn't have to accept the bet." He reminded me and then went back to business. "So, how did it go in the bathroom?"
"It went... and it wasn't too bad... I am still glad we did it."
"Cool," he agreed. "I do want it to be good for you."
"We'll see about that," I offered. "I'm doing it... but I'm not looking forward to it."
"Not even a little? You're not even a little bit curious?"
I shrugged. "Only a very little bit. Mostly I just hope I survive it."
"That's a bit melodramatic, but good enough." He accepted.
I turned to head for the bedroom, but he stopped me.
"Let's stay out here." Then answering my questioning look, "It gives us more options and it's also neutral territory. You need to be able to relax and I have a feeling that won't happen in bed."
I shrugged again. I guess it didn't matter to me. At least this way I wouldn't have to remake the bed later. Besides, as I started to think about it, I had some good furniture for screwing, a big overstuffed chair, a cozy sofa, and even the floor had a thick carpet, so we would at least be comfortable.
"Where do you want me?" I asked, resigned to my fate.
A quick scan of the space and he pointed to the rug. "We can start by just spooning. Get you used to the body contact. Then we can play it by ear."
"Okay..." I grunted and lay down on my side, facing away from my friend.
As he settled in behind me, I at first flinched at the touch, but then I relaxed and let it happen. I had been in this position many times with women, but always in Stevens spot. Having a warm body pressed against my backside was new to me and oddly pleasant. That is, until I felt the light bump of something soft yet solid, pressing between my buttocks. He wasn't trying to enter me, yet, but I could tell that he had already lubed his cock and it slid easily between my buttocks.
"You feel really nice," he said, echoing what I was thinking, but unwilling to say.
"Do I... do I need to do anything?"
"Mmm... no. Just relax," he said. "There's no hurry."
So, we laid like that, pressed together with his hardening shaft gliding lightly across my pucker but never actually threatening it, and my own, surprisingly, hardening shaft begging for some attention.
Steven found it and his fingers wrapped around my cock, gently stroking it.
"Well... I guess you're ready."
Then, still holding my dick, he shifted his hips so his own cock nestled firmly against the pucker of my ass hole. I started to clench, but he didn't actually push against me. He just held there with his knob in position, but not trying to push in. I took a deep, trembling breath as the broad, velvety tip of his cock pressed gently against my anus. My eyes were squeezed shut, my mind racing with fear, curiosity — while my body was a canvas of goosebumps, and my heart was thumping in my ears.
As much as I had complained about, and even feared, letting this happen, there was no question that this was a very sexual experience and my own cock betrayed me by being as hard as ever while having no purpose, as I anticipated being on the receiving end for the first time.
I felt a strange flutter in the muscle of my sphincter, and I suddenly realized that it was slowly loosening and wrapping around the crown of his cock, opening up and letting him in. It happened before I even had time to panic and tighten up again.
His cock knob slipped inside, and then my ass clamped like a vice around the neck of his shaft, but he had already stopped moving, not going any deeper while I adjusted to this change.
"Are you doing okay?" He asked.
His question refocused me and I became aware that my breathing was too fast and too shallow. So, I brought it back under control, drawing in a couple long, deep, raggedy breaths and consciously slowed my breathing.
"Yeah... I think so..."
"Does it hurt?"
Funny. I hadn't even paid attention to that when he slipped inside me.
"Um... no... Not really," I answered honestly. "I mean... I feel like I need to take a massive dump, but... it doesn't hurt."
"Good job, Scout," he praised. "Way to handle it."
We stayed like that for a while and I took the pause to test my ass, to see if I had any muscle strength left back there. Apparently I did.
"If you don't stop doing that I may not last till I get all the way in."
It hadn't occurred to me that he could feel what I was doing.
"I don't think my shitter is supposed to stretch this much. I just wanted to make sure you didn't break it... Besides, I thought the whole point was to get you off." I offered.
He grunted. "Maybe that's your whole point, but I plan to have some fun in the process."
"It's always about you," I sighed, surprisingly resigned and even relaxed enough to joke with him. "Okay... big boy... you better sex me up, stud."
"Please shut up," he laughed. That's the worst pillow talk I ever heard. You're making me lose my boner."
"Well, if you lost it, I'm pretty sure I found it," I answered, and even pressed against him, taking in a bit more of his shaft and discovering something important. "Oh god! That... that almost made me shoot."
He nuzzled against my back and whispered into my ear. "Welcome to the wonders of the male body. Most men never get to discover that."
"Does it feel like that for all guys?"
"Nah. I mean, most guys will feel stimulation, and even enjoy it, but not everyone reacts like you are.
"Lucky me..." I sighed.
"No... Lucky me," he countered. "I wasn't sure how you would react. Are you okay with me trying to make it happen again?"
The answer should have been obvious, but I was actually afraid of what would happen if I did cum. This was all new to me, and usually, after I came, I just wanted a long nap. If I finished before he was done, would I have to make him stop? Could I hold out long enough to let him to finish?" Luckily, I think Steven already understood my hesitation.
"It'll be okay. Don't worry about anything," he reassured me. "If we get to a point where you need me to stop, I will. But you need to at least let me get this show started."
Yeah... okay."
I expected him to push deeper, but instead he pulled back slowly, until just the head was inside me. Then he pushed back in, just as slowly, hitting and then passing that joy spot. I had the same, near orgasmic, experience, but it passed again without incident and I realized that it was just part of the experience and not yet the trigger for the real thing.
This was going to be something else that was new. I had always enjoyed sex, but it was just an enjoyable buildup to the final prize. This was the first time I had ever felt anything this intense right from the very beginning and if I was going to feel like that the whole time, I'm not sure how my rapidly pounding heart would be able to handle it. I guess I was going to find out. I could do nothing but whimper and clench the carpet pile, my body struggling to understand the unfamiliar girth that stretched me wider than I ever thought possible.
Steven kept pushing until I felt his groin press firmly against my buttocks. I had all of it... but I only a moment to appreciate that, because he pulled back out again, repeating the process and building up speed until he was fucking me for real. His hips were rocking in a steady rhythm, and the friction was exquisite. It was as if he'd been made to fit me perfectly
I couldn't help but focus on the feeling of his cock. It was stretching me open in a way I'd never felt before, a mix of pain and pleasure, a strange blend that sent shivers down my spine and had me biting my bottom lip to keep from crying out. He was lighting up nerves I didn't even know I had.
It was still intense, but not as intense as that initial shock of sensation had been. This was not at all what I had expected, or feared. As Steven's cock slid through me, I quickly realized that this was the best sex I had ever experienced. I might feel differently later, but for now I couldn't even imagine going back to the way it was before. I needed my best friend to fuck me, every day, maybe more than once a day, and if this could happen I would die happy.
It had become clear to Steven that I was no longer a reluctant participant. I was taking it and even hunching back against him, as he humped into me. He decided to change things up a bit, and he pushed against me, forcing me to roll to my stomach with him lying atop me. Now he had all the leverage he needed to sledge hammer my ass with his fat baby-maker. This was now my new favorite position, and I gleefully took every pounding blow, spreading my legs to give him deeper access.
"How... ungh... how did... ungh... you know?"
He slowed, giving me a moment to catch my breath and he asked, "How did I know what?"
He was still slithering through my bowels, but at least for now, not knocking me breathless.
"How did you know... oh god... that I would like it... this much?"
He chuckled close to my ear. "I didn't," he admitted. "Shit, I was half afraid it would end our friendship."
"But you did it anyway," I accused.
He paused and I suddenly knew that this had not been an easy choice for him. "It would have been devastating if that happened... and I would have spent the rest of my life trying to make it up to you... but... I had to know."
"Know what?"
He took a long deep breath. "If we could be a good fit... you know... together like this."
"No shit?"
"Yeah... no shit."
"You picked a hell of a way to test our friendship."
"I know."
"You really are one lucky bastard." I said, letting him know he had made the right choice.
"Maybe we both are," he answered, as he began to fuck me again. "You would have never known."
"Yeah... ugh... I think we both are..."
I let him punch fuck me against the floor for the longest time, and realized that he still showed no sign of finishing any time soon.
"Wait," I stopped him. "Let me up."
"Oh... um... okay," he mumbled, clearly concerned , but doing as I asked. "are you okay?"
My body felt the effects of having been beaten between the floor and my buddy's solid body and I took a few seconds to stretch out my limbs and get my joints moving again. Then, as Steven watched with nervous curiosity, I moved to the couch and sat back with my ass perched on the edge of the seat.
"Okay," I groaned. "Back to work," and as Steven enthusiastically took his place between my legs, I confessed, "I want to see what's happening."
As he took position, I had to admit that he had a really nice cock. He was a good-looking, well built guy, so that wasn't really a big surprise. That I now desperately wanted to feel it inside me again, was the real shocker.
Even the short time he had been out of me, was long enough for my ass to question whether this pudgy probe was supposed to be there. Luckily my earlier experience was enough to convince me that my ass was just being bitchy and it only needed to be reminded. Accepting that there might be at least some reentry pain, I pulled Steven toward me, forcing his cock through the temperamental ring of muscle.
I was delighted to discover that when he pressed against me, my sphincter instantly recognized the intruder and let it in without complaint. Being able to wrap my lags around my friend as he plunged into me, made this my new favorite position. In all honesty, it seemed like my favorite position was whatever position I was in at any given time.
However, from this position I was able to look down and see his cock shaft every time he pulled back, and knowing where it was going was the sexiest thing I had ever seen. Knowing that fat shank was getting ready to fill me, almost made me shoot off, so I had to look up again. Only, then I saw the look on my best friend's face, and the obvious pleasure he felt had almost the same effect on me.
With women, I always hoped it was pleasurable for them, but I was never sure. With Steven it was obvious, and I committed myself to letting him know it was the same for me.
"I can't believe we never did this before," I groaned. "What took you so long?"
He smiled. "There was an obnoxious straight dude who kept cock-blocking me."
"Huh... That dude was an fucking idiot."
"Absolutely," Steven agreed. "He probably still is... but he's the best piece of ass I've had in a long time."
I nodded. "I am the best piece of ass you will ever have."
"You will be if you ever shut up long enough to let me do my job."
He had been fucking me slowly the whole time we were joking with each other, sort of testing the waters, but now I needed to make it clear what I wanted.
"My lips are now sealed."
Steven decided to go for it, and I had to gasp as he rocked his hips, driving through my guts, full length and full speed. All my close calls with almost cumming finally met their match. He was fucking me to orgasm, mine and his.
Now that I was giving in to it, it took no time at all, and there was nothing I could do to stop it. I was building up a head of steam that had my entire body pulled tightly into an arc that lifted my ass and gave Steven a clear shot at my hole.
That didn't stop him from shifting his hips, making his cock hit me from changing angles that all seemed to have their own particular merit.
"Oh fuck!" I gasped. "I'm going to cum..."
Steven looked even more determined, and he held my firmly ass in his hands, holding me in place as he drove it home for a landing.
To my surprise, he still came first, his jackhammer pattern suddenly faltering. Then he plunged deep and held there as I felt the first pulse of his orgasm. I immediately fired off with my own, scattershot, covering my chest with a massive load.
Steven pulled back and then took a couple more pounding drives into me before coming to a full stop again, ball deep, and still shooting.
This all lasted probably no more than five or ten seconds, but it felt like slow-motion that lasted for ages. What I felt when he came inside me, and the body shaking force of my own orgasm would definitely linger in my mind for a long time.
Steven, who had looked strong throughout, finally seemed drained, and he dropped against me, completely ignoring the gooey mess that now bonding our torsos like Elmer's glue.
"Fuck..." Steven eventually mumbled. "I never guessed it would be like that."
"I laughed. "Wait a minute... You're the gay guy and I know I'm not your first. You had to know what it was like."
"Yeah," he agreed, "I fucked before... but not with you. That was... something else."
"Cool," I sighed.
"Please tell me it was good for you too." He was practically begging.
"Did you miss seeing me shoot off? You may notice that there's a sticky mess here."
"Yeah, I noticed," he chuckled, shifting enough to make my cum crackle as he pulled away from me. But dude's cumming is like dudes eating. They will do it even when it isn't always the tastiest meal."
"Fine, I'll admit it," I told him. "That was a surprisingly tasty meal."
"So... would you ever want to... eat at this establishment again?"
"God, you're a dork," I laughed. "Yes, we are definitely fucking again. I won't say you turned me gay... but you got me hooked. We are absolutely doing that again... maybe many, many times."
"Well, we'll have to see about that." He said, catching me off guard. then looking down at me with a smile. "I still haven't decided if you're my type."