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Fifty Bucks

Categories Fiction, Anal, First Time, Gay

Author: Steve_Black

Published: 02 March 2018

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“Shit, it’s really come down now. We’re snowed in for sure.”

I’m listening to my roommate moaning again about the snow storm that struck last night that is expected to last for at least two more days.

“Hey Cory, relax man. As long as we can get to the student union we won’t starve.”

He turned to look at me with obvious disgust on his face.

“It’s not food I need, it’s my girl friends ass that I need and with this storm there is no way her roommate will leave giving us the chance for a fuck.”

I’ve heard him saying that now since morning and it’s at the least the tenth time at that.

“It won’t kill you.”

“It’ll feel like it though.”

I’m probably as ticked about the storm as he is as I’d had plans to do some hiking in the woods at the edge of town but there is no way so I’m stuck here just like he is. The hours dragged by for him while I manage to keep busy studying.

Getting to dinner was a challenge as the storm had increased. We are bundled up against the cold. Getting to the student union took twice as long as normal and of course the line was long but all you can do is wait it out an hope they don’t run low on food.

We finally did get a half decent meal that we had seconds and thirds probably more out of boredom than hunger. Then before we left the student union we shopped for as much junk food as we could then headed back to our room where we got out of the bulky clothes. The TV was turned on and surfed the channels until we came across an old war movie starring the duke. We settled in to watch a movie we’ve each seen at least a dozen times but what the hell else is there to do. When the movie ended Cory started in with his whining again about needed to fuck something or he’d go nuts.

“Don’t look at me. If you’re so horny, go in the bathroom and jack off.”

“You just don’t understand man, I need to fuck something.”

With that said I saw him looking at me in a way that I didn’t like.

“No Cory; just forget it dude.”

He got up and went to his dresser where he picked up his wallet opening it he took some money out.

“I’ve got fifty bucks man; it’s all yours if you’ll just let me…” He didn’t finish what he was begging for and I stared at him. Well, it was more like I was staring at the money. I’m flat broke waiting for money from my parents that I had begged them to send.

“Fifty bucks, it’s all yours.”

“And you’ll never tell anyone?”

“My lips will be sealed tight.”

I hesitated several minutes going back and forth over doing it or not but that cash won out over my fear of any pain.

“Give me the money and there are rules.”

“Sure man, anything you say.”

I took the cash from him jamming it in the right front pocket of my jeans.

“Rule one: if it hurts to much the deal is off and you get your money back. Rule two: if I tell you to pull out and you don’t get it out fast enough you lose your money. Rule three: don’t forget rules one and two. Got it?”

“Yeah, I got it. No sweat.”

Still not that sure about this I stood up and went to my dresser searching for anything to use as lubricant. No way he’ll put that monster in my ass without it. After rummaging around a bit I came across a tube of suntan lotion. Sure don’t need it with a major snowstorm outside.

“You’ll put this on your cock before you even try to push it in. That’s rule number four.”

He grabbed the tube and kept staring at me. I figured there was no way to delay this any longer. I pulled my shirt off, leaned over and took my socks off. Shoes were off as soon as we entered the room. When I stood up again I was shocked to see him already naked and his cock is rock hard pointing right at me. Seeing the size of it again I had second thoughts about this but the money in my pocket is saying to take my clothes off and get it done so I opened my jeans then pushed them and my underwear off. Then I realized I have no idea how this is going to be done.

“Alright Cory, how is this going to happen?”

“Dude, all you have to do is lay on your stomach and I do everything else.”

“Okay but your bed, not mine.”

“Sure man, that’s cool.”

He followed me like a puppy to his bed where I laid down like he said. I watched over my shoulder as he squirted the suntan lotion into his right hand then smeared it all over his cock. Then he got on the bed straddling me his hand still on his cock. He leaned down and as I turned my head away I felt that monster press against my asshole. It felt like he was trying to shove it in with much more force than is required but I stopped that fast.

“Cory, slow down. Take it easy man, easy.”

“Yeah right; sorry.”

After that he did ease up quite a bit but he was still pushing with his cock. It felt like my asshole is being stretched and stretched. I figure that when it stretches wide enough his cock will slide in and that’s just about how it worked out. When I was certain I couldn’t be stretched anymore and was just about to tell him to forget it he slipped inside me. I knew I had to force myself to relax or this would be a major disaster. Maybe that’s what saved me but so far the only thing I’m feeling is pressure as he eased deeper than more.

“Is it all the way in?” I asked.

"About half.”

“Oh shit.” I silently moaned.

He pushed and pushed easing more and more cock in my ass. I kept forcing myself to relax as much as I can but still expecting pain at anytime. When I felt his groin pressing against my butt cheeks I couldn’t believe it. I didn’t need to ask if I have it all as it’s rather obvious that I do.

Once he got the all the way in he stopped moving maybe letting me adjust to having a battering ram inside my ass. At least that’s what it feels like.

“What did you say?” I asked.

“Just want to know if I’m hurting you?”

“It’s okay for now Cory but just take it real easy. Don’t start pounding it in me.”

“Yeah, right dude.”

That’s when he pulled back a few inches then slowly pushed back in. After a few more strokes I felt myself relaxing even more with the realization that there is no pain. Maybe my further relaxation helped more because it now feels like he’s sliding much easier inside me. He’s now taking very long slow strokes pulling all the way back until just his cock-head is still in my ass then pushing all the way back in. He kept stroking and stroking like that. Now of course I want him to cum and get this over with but then the strangest thing happened. He shifted a bit, who knows why, and it feels like he’s rubbing against something and that something is feeling very very good. The more he continues stroking the better the feeling gets. I actually feel like I’m going to cum and I’m dumbfounded with that realization. I never expected it to feel good. Not in my wildest thoughts about this did think that I would enjoy it.

Now he’s speeding up and that is just making me feel even better. It feels so fantastic, so awesome that I put knuckle in my mouth to bite down on to keep me from moaning in pleasure of what his cock is doing to me. Now he’s really fucking me fast and hard pounding in me doing exactly what I told him not to do but I made no effort to stop him. There is no way I want what he’s doing to me to end. Now he’s varying his speed and depth of his thrusts driving me insane with pleasure. Then it started but it was like no cum I’ve ever had before. There was no throbbing of my cock. It felt more like someone had turned on a faucet. I’m aware cum is pouring out of me but unlike the cum I’m familiar with; a cum that is over in a few spurts, this cum just keeps going and going. It’s all I can do not to cry out with the pleasure I’m having all being caused by Cory’s monster cock fucking my ass.

Even though I have no awareness of the passage of time it has to have lasted for at least two minutes so far with no indication it’s going to end. That’s when Cory rammed his cock high up in my ass and I felt him cumming and oh my god my cum somehow got even better. I can feel Cory’s cock throbbing over and over in my ass. I can feel his cum shooting up inside me. Four, five, six times he cums before it was over for him and with the end of his thrusting my cum slowly, very slowly came to an end. Neither of us said a word as he collapsed on my back, his weight feeling very good to me right now. I can hear him as slowly gets control of his breathing.

“Oh god dude, did I ever need that. Whew, what a fuck.”

“Cory, can you reach my pants?”

“Your pants? Do you want to get dressed now?”

“Just get my pants.”

I felt him moving on top of me and I feared he’d pull out in his struggle to stretch enough to reach them.

“Uh, uh. Just a bit more. There, got ‘em.”

I was able to fumble with my pants enough to reach into the right front pocket and pull out the fifty bucks.

“Here Cory.”

“You’re giving it back? I don’t understand.”

“You’ll need the money so you can pay to fuck me again.”

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