First Time Analized

Ah, that first time...

I was only 12 back then. I'd been fooling around with two friends from school. Let's call 'em Elmer and Fred.
We'd mutually ********** in the bathrooms at school, standing at the urinals, pulling our hands back the moment we heard someone touching the door.
Fred had the biggest **** of us three, but for some reason I was more into Elmer. I loved jacking him off. I'd take hold of the base of his penis, and pull the loose skin up and down in my grip. And he did that wonderful thing where he'd take hold of my nutsack just below my penis and above my balls, then squeeze. It would hurt and feel good in a weird, pleasant combination.
It was gym class when he took my *** the first time. We scrambled off to the bathroom, and got in a stall. We pulled our shorts down and started rubbing, squeezing, and pumping each other's *****. As he was rubbing our ***** together and I was fumbling with his nutsack, I pulled my **** out of his hand and turned around. I got on my knees on the toilet seat, so nobody would notice two pairs of feet, leaning on the tank. "Hey, let's try it in my ***!" I said.
- "You sure?"
- "Yeah, why not?"
- "We could get AIDS I think." (that was as much as we knew back then, haha)
- "Man it's only once.. come on!"

Elmer pulled a cheek aside as I parted the other, and he put his **** against my rosebud.
We didn't have any lubrication that day, so it hurt like ****. He didn't actually "****" me in the usual sense of the word. He just got his head across my sphincter, then came all over my *******. I remember the moment he got into me I asked him, "Man it kinda hurts - how does it feel for you?" and he said, "Just like wanking, but multiplied times infinity!"

We cleaned my *** with toilet paper, then Elmer jacked me off. Needless to say, it was one of my most memorable ejaculations!

I've loved having things up my *** ever since then. The thicker, the deeper, the better!
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2 Responses May 9, 2012

I have been having butt hole poked since 5 yrs. I offend if it hurt girls so much when they get their cherry pop that they bleed why do they still want more. I remember a girl I pop her cherry she bleed the first time and the second time too. But some how I can relate to that now. I can remember many times my butt sore for two or three days and the pain as the head is push in. Some times I fell like saying No it hurts too much. But I bare the pain to please my partner.. Funny after fifteen minutes of pounding it's all good and after I feel the hot *** inside the pain was worth it and I'm ready for more with a sore and numb butt

Great story. It's funny how even when we're so young we know we want something in our ***.