Betting to Evolve

Another cock entered me.

I was blindfolded. Tied face down to the bed. I couldn't turn my head at all so I was breathing into the sheets. Every breath I took was damp with vapor from my lungs and sweat.

He wasn't like the last guy or the guy before. This one was slow, patient as his prick went in. Thick but short. I felt his ample belly on my butt before his crotch hit my ass.

"God, he feels so good." The gruff voice said. His pubes were an assault to the now-tender flesh of my asshole. His stomach smeared the other cumshots around my buttcheeks.

Was he the fifth, or was there another guy who went twice?

A laugh from somewhere to my right, "Yeah, he feels awesome. He loves taking cock." That voice was somewhat effeminate.

"And it's his first bareback gangbang. Don't forget that." I DID know that voice.

--------------------------------

Six months ago I was grilling burgers on my patio. My wife was sitting with her feet up on the unlit fire pit. It was a beautiful day, the kids were over at their friends' houses. Nothing was an issue at all.

My brother-in-law was sitting in another chair by my wife. Her brother Terry. Nice guy.

"What I'm saying here is that I can absolutely shoot a bullseye, dead on, with whatever you want me to. Up to a hundred yards." He was bragging, he did a lot of that.

"Bullshit." I said. I was a good shot, but there's no way Terry was a better shot than me.

He looked at me with a raised eyebrow, "Care to make a wager on that?" He had a look on his face that was...a bit off.

With the confidence that always screws a guy, "Sure. Are we going against each other or just the target?"

"How about both. A different wager for both. I can deadeye a target, and beat you at it." He chuffed.

I laughed, "You've got a deal. What're we betting?"

He looked at my wife, "If I win one, you buy me a bottle of Johnny Walker Blue. If you win one, same deal." I nodded, "If you win both I will come over and paint all those rooms Kim wants painted." I nodded on that one, good lord I didn't want to.

"And if I win both, I fuck you in the ass." He said. I just laughed a bit too hard. Terry was full-on gay. I had always taken him for a fuck-ee, not a fuck-er.

The look on his face still had that wry grin, "Can you believe that shit?" I asked Kim.

"If you're confident, there's no issue. If you lose? Well, you can see why I don't like it that much." She was buzzing hard off margaritas.

"You're joking, right?" I said, openly to both of them.

Kim shrugged. Terry grinned wider, "Dude, you're confident there's no issue, right? You don't have to worry at all."

The next Saturday we were at the gun range. Terry took hold of my pistol and had a professional grip and stance, "How far out are we going here?" I decided to make it hard on him.

"How about 30 yards? Think you can handle that?" I knew I could get it in the center circle no problem.

I ran the target out, "OK, I'll give you one practice shot, then you've got to dead-center it."

He glanced at me, "Same applies to you." He looked far too confident for my liking.

His first shot went low and to the left. I scoffed. The second went so close to the center you'd have to measure it with a caliper. "There you go. Think you can get that with two shots?"

I didn't. I missed the center green circle by a half inch in two directions. "How about this? You get two more shots. If you can get them in the circle, we'll call it a draw."

My next shot went just barely to the right of his, well in the target. I was relieved. The second went wide at least five inches.

"Bad luck there buddy." He said, that wide, wide grin on his face.

I was panicking. Kim had said the next day that I'd made a deal. If I lost the bet, I better get to training my butt.

"Double or nothing on the rifle range." I said, grasping.

He laughed, "So you're telling me if I outshoot you with one of your rifles, I get to fuck you twice?" I nodded. There was absolutely no way he could bullseye that target with my rifle.

We walked down the long rows until we got to the rifle range. "So, how far are we going with this one?" He smiled like a predator.

I thought quickly. What had I practiced? Could I repeat it? Could I do it again? "250 yards" I said.

"Hmm. How about you go first on this one?" He said, "Same applies, two shots, deal?" I nodded.

When things calmed down and the range master said cease fire, I walked the target out to the 250 point. Then I made my way back, confident now.

The buzzer went off and I leaned across the bench. I checked the scope, checked it again, squeezed the trigger.

My first shot went through the target an inch from the center. My second went only a hair further away. No way could he beat that one. I was calm again.

He took the rifle and leaned. He stood again. "I'm going to wait for the next cease, OK?" Ha! I had him!

Several minutes went by and when he had the opportunity he walked out to the target. I saw him lean down, look hard at the paper. I just grinned like an idiot.

Until he took the target off the mount and walked it back to the 300 marker.

"No fucking way." I said under my breath.

He walked all the way back to the stall, "That's gonna make it more fair." The buzzer went off.

His fingers fiddled with the bolt, rotated the gun a couple times, lifting and checking its balance. Then he took position, "I get two shots, right? Two shots that have to beat both of yours?" I gave him an affirmative answer.

He took a view through the scope, looked along the gun, looked back through the scope and squeezed while I looked through the spotter.

His first shot was impossible. There was no goddam way. He'd put it millimeters from the dead center. Impossibly close. How the actual fuck? "First one looks good. Let's try this second one."

He didn't look through the scope. He looked along the barrel. He took a deep breath and squeezed.

The second shot was halfway between his first one and my first. No. Fucking. Way.

"Well, that looks like I've got two times at your ass." He laughed.

I looked at him dead on, "You're joking right?"

"Oh, there's no joking here. I plan on feeling your insides, Greg." He continued to laugh.

I thought desperately, "OK, how about this...double or nothing with a bow." I wasn't as good with a bow as a gun, but I wasn't bad.

He laughed even harder, "Oh no, we did double or nothing, this is TRIPLE or nothing."

The next afternoon I watched as he put four arrows directly in the center of a target at 55 yards. I'd missed the fucking thing by a foot on my third arrow.

"Oh Kimmy. I'm going to fuck your husband up the ass SIX times...can you believe that?" He was almost falling over laughing.

"I think it was bullshit you didn't tell him you were in the olympics tryouts." she said in her casual manner. "Just don't blow out his ass."

That night we were in bed and I looked to her, "I mean, do you think he's going to go through with it?"

"What do you think?" she asked.

I shrugged, "I don't know what's going on in his head." I said in answer.

She looked straight at me, "One thing to remember about Terry. He says he's going to do something? He does that thing. That's how he's been his whole life."

"Well jesus! I mean, your brother fucking me?" I looked at her like she was an alien.

"Well he's not going to fuck ME." she laughed. This was funny to her.

**************

Saturday afternoon I was sitting in his beautifully furnished apartment in the center of the downtown area of our city.

Terry was dressed in an oversized t-shirt and sweatshorts. We sat across from each other on his stylish, low couches. We were chatting about anything in the world other than why I was there.

I was starting to think maybe he'd just let it slide when he stood suddenly, a definite bulge...and not a small one...in his shorts. "Well, I suppose we ought to do this first one. Hell, I might even have the second one in me today." He chuckled.

"Are you sure you want to go through with this? I mean, I'm your sister's husband for god's sake." I felt like I was pleading.

He shrugged, "Well, I'm not going to fuck HER."

I should probably mention a couple things. I'm a pretty good looking guy. I'm built well, touch under six foot, greying hair but it's cut well. I go to the gym three times a week. I'm doing good at 42.

Terry is about 5'6". He's rail thin but it looks decent on him. He's got kinda long sandy blonde hair, down to his shoulders.

I'm not bad looking, but he's fucking gorgeous. Like model level. He's built utterly fucking perfect. Like it makes you ill to be around him.

So we walked to the bedroom. One of the longest walks I've ever taken.

No sooner did we get in the door of his huge, bay window bedroom than he stripped. Completely.

I like to think I've got a pretty average dick. One drunk night a girlfriend of mine in college measured it at just under seven inches, and thick as most guys in pornos.

Terry almost made me feel inadequate. He had me by at least an inch and a half, maybe two, with girth just a little narrower. It was shaped like a wedge, smaller at the tip but widening as you went towards his body. He was uncircumcised and had a small bit of excess skin closing your access to his glans.

He was shaved. His balls below were as impressive as his cock, veined and heavy.

"Uh... this is definitely not gonna work." I mean, I'd resigned myself over the past week to having to do something, but there was no way that monstrous thing was getting up my butt.

He just smiled, this time in a calm, friendly way. "Greg, this isn't the first time I've done this. In just a little bit I'll be balls deep inside you. Just trust that I know what I mean."

The term 'balls deep' made me cringe. What the fuck was I doing here? This was fucking crazy. I'm a straight man, straight men don't get buttfucked.

I sighed, still dressed. "What...do I do?"

"Go ahead and take your clothes off. We'll go from there." He walked to the bedside table and pulled out a pump bottle of something.

Stripping, I stood there away from the windows and waited for further instructions. "Jesus Greg. That's a great dick man. We might have a day where we switch positions." Nothing could be further from my mind.

He had me lay down on my side on his spacious bed facing towards the other side. Then he had me raise my left leg, the upper one, until he was satisfied.

"Ok. What we're gonna do here is use a couple fingers to get things started. Just relax and let the lube do it's job." I don't know how I was supposed to relax. I was nude, my ass hanging out towards a very, very gay man. Holy shit.

I felt the cool gel hit my crack and hole and instinctively twitched. "You keep doing that and this is going to hurt. We don't want that, so just cool down." A second later I felt one of his fingers rub back and forth over my sphincter, just putting pressure on it, not inserting.

Then the funny thing happened. He started to push in just the tiniest bit. I felt this invisible line between my ass and cock like a guitar string. He pulled back, pressed again and it hit me once more.

I felt my prick go hard. Not just hard but out of hand hard. Like hard like a teenager. What the fuck was going on?

He worked that finger until it was completely in and I felt his knuckle against me. "You're doing just fine, but calm down." I nodded. The issue was that I wasn't breathing fast because I was nervous, it was because of that connection.

Every time a knuckle would pass into me, widening and narrowing, I would feel it. An electricity that generated on every bit of my ring and shoot down through my taint, flashing to my balls, driving up the spongy area under my shaft and hitting my cock head.

Then, his fifth time pressing that finger in I felt him touch it. I was already reeling from another wave when his finger tapped against my prostate.

That link between everything, already at eleven, cracked into me like a thunderbolt. It was like someone cut my body in half from my head down to my groin and moved against every bare nerve.

I couldn't help myself as an 'uhhhhnn' came from somewhere inside me. "It's alright, you're doing great." He didn't know the half of it. I was riding a high that I hadn't realized existed.

The very next time he went towards me I felt a second slick finger accompany the first. I felt them spread me open further and instead of getting those nerves get further away it felt like my body had built new ones that only existed to give me pleasure.

It was like a cloud. A thick fog between my rational brain and whatever was going on in the thunderstorm of my senses. Every press of those two fingers and I lost all capacity to think.

"You're doing real good, Greg. I think we can go ahead and move on towards the main event." He removed the digits from me and I came back slightly closer to the planet.

The bed shifted as I felt him come up, then his smooth knee against my leg. Movement I couldn't see and a hardness flopped on my lower cheek close to my crack.

His voice was a little off now, a little less 'professional'. "Ok, it should be fine for a few beginning presses, but as you feel things get a bit more tight, bear down like you're going to the bathroom. It.. It will be counter intuitive but it will help ease that."

Briefly, the presence went away from me and a second later I felt a lubed hand against my left, upper cheek. It pressed my crack open, baring my asshole.

It was...to call it life changing doesn't do it justice. It WAS life changing. I wouldn't ever be the same after it.

Split seconds after I felt his head touch my body, my sexual urges said to me in a voice I swear I heard, "Well, now we're fucked." Another voice answered, "Not just yet, but really soon."

He pushed the head inside in almost one push and I gasped. I couldn't get air in fast enough. My body had just given over to 'Let it Happen' and it couldn't cope with what was going on.

"You're doing damn well." He was moving back and forth at a slow pace, pressing inside me a fraction of an inch each time. At first there was a way I could hold onto things.

By the time he'd gotten enough inside me I finally had to bear down, I knew that I was going to cum at some point. It was just a matter of time.

Through the straight intensity, I thought 'I'm not gay. Why is this so...' and then I'd think about it and lose my train of thought.

It was like an orchestra where each one of my nerve endings was an instrument. They were all working in tandem to make a symphony.

When I realized his groin had hit my ass cheek I tried to bring myself back. My breathing calmed down. I took stock of things and tried to be rational, analytical.

Terry was inside me, completely. I felt his balls against my lower ass cheek. I could feel the size of him against my insides. My brain briefly went to the idea of how he was stretching me but I had to shut that down or I wouldn't be able to think at all.

What the hell was going on? Again, the conscious, normal, everyday part of my brain was going through emotions like a machine gun. Desperation, panic, anxiety, denial and more.

Then he started withdrawing and all of the rational thoughts I had went somewhere as that intense pleasure came back racing through me in every direction now.

The motion of his flesh against mine was like a massage I'd never known I needed somewhere I didn't know I could feel with nerves that had never been used.

I couldn't tell how much he'd pulled out but his press back in raised the stakes again.

How much more of this could I take? You can't just keep getting pleasure, right? At some point it has to give.

As he began a leisurely pace in and out, I hit a plateau. My imagination saw me walking on the top of an uneven surface thousands of feet off the stability of the ground. I'd walk into a slight dip and the sensation would be almost real, walk to a slight rise and I couldn't see straight. All of this while my pleasure was in the sky.

I kept gasping, "It's all good, Greg. You're doing great." He said in a voice I could barely hear through the rushing sound of my blood in my ears, somehow moving this feeling around my body with my circulatory system.

"Got to be honest." He followed, "I was just gonna get you up here, get inside you and call it a day. I think...I think I'm gonna have to cum though. You're...it's like you're different. Like there's something more than just me taking your ass for your first time." His breath was going slow but purposefully, calming.

I tried to speak, "You...got...to you got...do...what you think is...right...to do." I sounded like an idiot. I couldn't speak alongside everything that my brain was dealing with.

My body reacted. I pushed back against him.

"What was THAT?" He asked with either real or mock surprise. My ears weren't clear enough to tell.

I huffed. I was so close to coming. I could feel it right there. "I just...I nee...want to get...this over with..."

The second he picked up his pace my gate was sealed. Everything had been so completely overloaded that adding in a quick pace left me unable to cope.

My prick began erupting, spewing against my leg in hot splashes with more pressure, more force than I'd felt in years. It was made all the more impressive due to how even this sensation made what was happening in my ass that much more intense.

"Uhhhnnn" was the noise that came out of me. I couldn't believe I'd made a noise.

Then the next strange thing happened. See, in the course of my life I've had a long recharge period between sessions. When Kim and I were in our young fuck-all-the-time years, I could get it back up in ten minutes. Nowadays I pretty much needed a nap.

30 seconds had gone by since I'd blown jizz all over the duvet and my leg and I was still hard. Still stimulated and still in intense pleasure.

Had this been my 'thing' all along? I mean, I loved every second of Kim and me naked together, and I'd had truly astonishing times with her. But never like this. Never this...express route to my pleasure centers.

Somewhere I realized I'd been pushing back at him, keeping time with his thrusts, feeling his sack roll against my butt. It must have been working.

"Ah...ah...I'm...Greg, I'm gonna cum." I just grunted something unheard in reply, "I'm...not...not gonna pull out."

A split second of hilarity in my brain. I got buttfucked, I came from it, and now I'm gonna have my first creampie. If I wasn't so sideways from everything, I'd have laughed.

"Uh...uh...uh...uh..." he repeated, more breathing out than speaking, "oh...uh...gonna...fuck...TAKE! IT!"

He pressed in harder than he had yet and I felt him...thickening. Again, it seemed like as I opened up, new pleasure centers formed between the previous ones.

They appeared and vanished as he unloaded into my colon. It was a blinding excitement and the ache of loss, all within seconds of each other.

Finally he finished. He moved himself in and out a few more movements before slowly removing himself. It was like I'd had something necessary removed, like an organ that I needed to survive...something vital...was gone.

"So uh...did you start getting into it there sat the end, Greg? Kinda started working for it a little bit." I didn't look but I could hear a grin in his voice.

"...I just wanted you to get it over with. Thought if I did that it would work." Seemed like a good excuse.

"Uh huh." His voice was doubtful and full of some superiority, "then how come you came all over my bed five minutes ago?"

Jesus...5 minutes? It had felt like no time at all. Like 30 seconds ago.

I couldn't think of a single answer. The fact I'd come up with the previous lie was a miracle. My head was still swimming, still longing.