The first time I got fucked I was a fresh faced fifth grader with a fifteen year old boy. I did it for money too.
My parents divorced when I was thirteen and in eighth grade when I lied my age, said I was fifteen and with a work permit signed by my mom got a job at a fast food place. I barely looked eleven, slow to hit puberty it was my mom's signed work permit and the the managers lust for my younger than twink looks that got me hired.
After a few weeks of his active attention he made his move in the office where he made me change so he could watch. I'd just stepped out of my jeans and stood facing the other way in my underpants. Suddenly he was all over me. He dragged me over to his desk with one hand over my mouth and the other around my waist.
His hand dropped to my underpants cupping my boyishly small cock'n balls. He pushed against my butt and I uncontrollably got an errection. I was so embarrassed and for some reason apologized. He made me suck him and then told me to take off my underpants, I said no. I hadn't developed yet and was still totally smooth and didn't want him to see.
It angered him and he ordered me to bend over his desk. I thought he was gonna spank me instead he ripped the back of my underpants, using spit as lube he painfully fucked me. He told me to take the rest of the night off and he'd punch me out later.
He also told me not to wear any underpants, but I always did because I was too shy not to. He taught me how to suck really good. He really got excited when he found out I was actually thirteen for some reason?
When Mom and Dad separated the neighborhood corner grocery store offered me an after school job for a couple of hours to help my mom out.
It wasn't long before he was helping himself to my thirteen year old fresh and firmly tight boycheeks. Looking back he was fairly thick and I was surprised that my tight little ass could accommodate it. He was well into his fifties with a sick wife and I guess he needed me as a surrogate.
He definitely was tender, waiting a few days in between fucks he taught me to suck. He was very generous with me and my mom, providing groceries and cash too. Having sex with other boys became fun but couldn't compare to a man's love making. So I guess it kind of ruined those tender boy/boy explorations that I was past.
I’m guessing the reward at the end was worth it along with all the other money. I’m not sure if you enjoyed it or not; myself personally - I loved when I was a teenager and had older sugar daddies - the presents were lovely and the sex was amazing