A gay story: The Greatest Sin in the Book I made the mistake of telling a my friend Mike that I had experimented with anal toys. Next thing I know I’m crouching my naked ass just above his thick, veiny, greased up pickle, wondering whether or not I could actually do it.
It started about a month ago. My name is Patrick, Patty to my friends. Just your average slim, freckled, red headed Irish boy. Straight and Catholic. I’m 18 and it’s my last year before college. Its the priest’s fault. Last month he was preaching on and on about the dangers of homosexuality. He just kept going on and on about the perversions of anal sex and sodomy. The assistant priest had to put his hands on his shoulders to calm him down. He was red faced and screaming up there. It was like he was obsessed with it, and now so was I.
The greatest sin in the book, the priest called it. Worse than murder, worse than stealing, worse than genocide. You didn’t get any more evil than a sodomite. But how could that be? As your average catholic school kid I had done just about everything except straight sex, I could grind with my lab partner Stacy until the crotch wore out on my jeans, but the idea of actually fucking her was a one-way trip to hell. Pre-marital sex was the evilest thing I could think of, I would say a hail mary after each time I jacked off thinking about it, I used to be obsessed with that. And now I find out there is something worse? It didn’t make sense.
At first I was just trying to picture it, just to understand what it even was. Ok, I get why I guy would want to stick his willy up someone’s bottom, any bottom (as a good catholic boy I was taught never to swear or be vulgar). There are all kinds of perverts. I had a cousin who would carve a hole in a water melon and stick his mickey in there. I know this because he carved two holes in one and asked me to do it with him, some boys are just sick.
But why would a guy want a doodle up his own fanny? I went to online and found ad after ad on site after site of guys begging for other guys to put their pickles up their bottoms. To do something so gross, that’s so bad for you (according to the priest), you must be getting something out of it. The filter on my computer blocked all the gross porn-o websites, thank God, but that also meant I couldn’t actually see how a boy could enjoy that. That same sick cousin once paid me ten bucks lick his underwear, he wasn’t in it, but it was still gross. These guys in the ads weren’t even asking for money. Could it possibly feel…. good to have a hog inside of your rear?
This question bothered me day in and day out. It was all I could think about. I started to understand why that priest was so angry, but I still couldn’t figure out why someone would even want to do something so perverted.
I decided I had to do an experiment, just so I could get this sodomy business out of my head. First I went to the “bad,” high-school across town posing as a student. I just snuck in line behind the other students through the metal detector. Inside the school I found the legendary bowl full of condoms all the kids at my school used to whisper about, I could hardly believe it was real. It was in the nurses office, just sitting there like it was no big deal. When I took a couple, the nurse just looked up at me bored, then back down to her book. She didn’t even try to stop me, what kind of Gomorrah was this place?
I went back home and searched around the house for something that might work, when I found my mothers broom I knew I was in business. I cleaned it first, unrolled the condom over the top of the handle (being a good catholic boy with no sex education this took several tries).
I was scared, I half expected the devil to walk into my room and scream “Gotcha!.” Standing, I placed the tip of this wooden rod at the base of my hole, and sat downward. My heart was pumping. It hurt going in, but after the top popped in the rest just slid inside me pretty easily. I felt something, it was weird, kind of good maybe, but it wasn’t the greatest sin in the book by any means. I couldn’t imagine people risking their very souls over homo-sexuality if this was as good as it gets.
I needed to take it a step farther. I bought a vibrator online with my parent’s credit card, it would be billed as “City E-Lectrics” so hopefully they would never noticed. I tried whacking my noodle with the vibrator up me, it felt good, but it still wasn’t quite enough.
Before these days I barely ever relieved my self, you know, sexually? Now I had to go into the church bathroom after every sermon this priest gave, as sodomy was all he seemed concerned about. Phrases like, “Hell fire and damnation of the worst variety exist for the boy who tempts other men into placing their manhoods inside of him!” I got this weird feeling up my bottom when the priest shouted, and no matter how hard I tried I couldn’t soothe it.
The vibrator was nice but I felt guilty after each time so I threw it out, in the neighbors trash can of course. It wasn’t getting me where I wanted anyway, I was looking up “thrusting sex machines” (in the 1000s of dollars) when I decided I should just pray harder, and let myself fall into God’s hands. As it turns out the Lord our God had plans for me indeed.
Like I said I’m a good catholic boy, but idle hands are the devils playpen and on one extremely boring day me and my buddy Mike jimmied open the special cabinet in the school chapel and stole some communion wine. Don’t judge me too harshly, I felt pretty bad doing it. Mike is 19, making him the older one, so he shouldn’t of led me astray.
We where getting buzzed in Mikes parent’s room, we found his dad’s playboys under the bed and were flipping through them. A sister at school once told us picturing a naked lady sometimes happens on accident, so it was not a sin as long as you didn’t picture her for more then ten seconds. So we timed our selves looking at the naked pics for eight seconds, then stopping, then looking again for 8, and so on.
Drunkenly Mike decided we should confess our sins to each other in case we died before tomorrow’s mass. I agreed, I mean you never know. It turns out Mike was guilty about spanking off his hot dog almost all the time. As much as twice a day sometimes, can you believe it?! I was feeling pretty guilty about playing around with the whole greatest sin thing, and stealing my parent’s credit card to buy that vibrating willy. So drunk as a skunk, I told him about it. He got quiet for a while, and we went back to our playboy time game. I felt like a pervert, he’s not a priest, I shouldn’t have confessed to him.
“You know Patty, it probably didn’t work because your fake willies, the broom handle and the vibrator, aren’t anything like what a real willy looks like. Like this, for example.”
Mike was so drunk he stumbled as he stood up. Then he just undid his fly and pushed his pants down and there was his hard lollipop, about 6 inches growing into seven. Veiny and uncut, with a brownish foreskin over the pink head. It was like it was coming at me, enticing me to sin. Like the snake did to Eve, this snake was coming at me.
“Mike, put that thing away! Its sinful, it’s perverted to have it out!”
“But Patty, how can you resist sin if you don’t even know what sin feels like? I bet if you took my penis up you butt, just once, you’d never feel the need to do it again. Then you can just confess to the priest tomorrow and you’ll be forgiven. And for me it will be just like jacking off only better.”
I can’t believe he said “penis!” The devil was truly in this room. He said cause he wasn’t even touching his thing himself it wasn’t even a sin for him, and I could just confess. He was right, at least that ‘s what I thought in my drunken state.
“Ok, Mike. we’re both straight so…. I guess its just two dudes helping each other out. But don’t blow your fireman inside me, that would make it a real sin. This is just a practice sin, to see what it’s like.”
“Exactly, a practice sin.”
Mike was so horned up he just laid down right there on the floor. He grabbed some lube from his parents sock drawer (a nice married couple with lube? Perverts!) and greased up his fat pickle. He laid back and closed his eyes while I shyly took my pants off. This was starting to feel like a bad idea.
I greased between my own smooth white cheeks, crouched my booty about half an inch above his hard snake. He started breathing hard, I could feel the warmth of his rod bellow my hole.
This is crazy! And I was just about to tell Mike that, stand up and leave when I heard the priests voice in the back of my head. “The greatest sin in the greatest book ever written! Pity on all you sinners who do not repent, for it is the devil himself that you will find inside the rapture of sodomy!” My knees started to weaken and his floppy foreskin brushed against my hole. I quietly said a prayer to myself.
“Lord give me chastity, just not today.”
Then I lowered myself onto it. It hurt!
“Oh god Mike you’re so thick! Oh dear, I just blasphemed!”
“The is the best feeling ever!” Mike yelled back, thank God his parent’s weren’t home and his grandma was deaf. I lowered my self slowly down onto is cock, the first inch went in very slowly, then my foot slipped, I lost my balance and his whole bone went up my hole in a second, oh god did that hurt, deep inside me like nothing I’d ever felt before! We both screamed so loud his deaf grandmother called out to us.
“Are you boys watching a scary movie in there?”
A bead of sweat dripped off my chin, onto my cock then fell to my balls, and dripped onto Mike’s balls.
Mike could barely talk, neither could I. But I knew she’d come in here if he didn’t say something, so I just just looked back at Mike and mouthed “talk.” He spoke, his voice shaking, trying to control his breathing. Trying not to sound like he was sodomizing his school friend. With each word he spoke I felt his bone twitch inside of me.
“No… granny… go… back… to sleep!”
His meat wiggles against my prostate.
“Don’t watch scary movies, its a sin!”
Some pre-cum drips down my cock.
“I know granny, oh god, ugh, please go back… to sleep.”
“Don’t take the lords name in vain.”
With that she shut up, thanks to her distraction I forgot about the pain up my bottom.
“Ugh, this feels weird.” My dick was inflating like an air mattress. My own uncut meat getting bigger then I’d ever seen it. It was so hard it hurt.
“Oh Patty, this is great. Try bouncing on it.”
He thrust his hips up forcing me to bounce on it. It still hurt but less so now. I pushed myself all the way up his shaft until just the head was inside me, oh god this feels weird, then I very slowly slid back down to his balls. I did this a couple of times and it was starting to feel really good. Better than touching myself. His hard cock (oh God, how can I even think that word) going inside of me then out on me, soon he was humping in time with me. It hurt, he was going too fast but I couldn’t stop him. I needed it!
We got so intense it was like the priest was speaking through us.
“Take it you sinner! Take this cock and burn in hell!”
“Give it to me, devil! Give me that cock so I can burn in hell!”
I looked down at my cock as all the pressure in me built up and I shot the biggest load of my life right onto my own face, plastering me. The salty/sweet cum dripped into my mouth and I was too dazed to stop from swallowing it.
With one more thrust Mike forced another squirt out of my cock as he shot his own seed up my ass.
“Whoops!”
“Mike!”
“Sorry dude!” He said as gush after gush of hot semen filled me up, thrusting with each explosion. “Won’t happen next time.”
What did he mean, “next time?” When we came off our high we both got really embarrassed. I stood up and his wet shrinking willy flopped out of my hole. As catholic guilt washed over both of us I got dressed and left without even taking a shower. Walking home some of his seed would drip out from me and down my leg to my shoes and onto the sidewalk. I hope no one noticed.
As it would turn out the priest wouldn’t be available to take my confession until the next week, and oh the sins I collected by then!