Straight Female / 30
Nobody Ever Found Out.
In our senior year Bryan was still the bunt of all the virgin jokes in high school. He was in my group a friends because we all grew up together. But Bryan was... how can I say it?-- by high school standards-- kinda a tool. He was into books, and grades, had misfitting glasses, was bad at dressing, and was a tubby-chubby. He really suffered drastically with self confidence.
He was a real friend as fair as high school friends go. We loved him, but we also loved having a built in punchline for every joke that cold be told. He belonged to our group but was teased ruthlessly. To our surprise it always took our sh!t and took it well and I think that is what kept in the inner circle.
You know how mean high school kids can be and by senior year he was our token "loser virgin" group member and got ragged on every day not only for being a virgin but not being able to likely change that anytime soon. But the joke was on them, he was not a virgin. I know that because I had secretly taken his V-card during the summer and he never told anyone because I had a boy friend also in our circle of friends. I am not saying i was the hottest girl at school but I was up there and well sought after and a million miles out Bryan range. Nobody would ever suspect he got to fuck me.
Most of our friends were gone on various summer adventures. May family could not afford that and Bryan was always hanging around. One night when no one was home I smoking up in my basement and Bryan I think started to get a contact high because out of no place he blurted out
"Rylee, I have loved you since we were kids. I know you'd never feel the same. I don't expect you too, I actually understand your with Jason, and you deserve someone like him. I just want you to know, before school ends next year, you will always be my first crush."
Maybe I was high, maybe i was horny, because Jason had been gone for weeks. Mostly, I saw the look in his eyes and I knew right then and there I was going to pity fuck him. I took my last hit on the puff and saying nothing, walked over to him and got real fucking close in his space. I loved his confusion and i think he actually trembled in excitement of being that close to me.
I brought my body into his and he felt my tits against his chubby body, i brought me lips as if to kiss him but instead, out of no place I pushing him down hard on my couch and straddled him. And straddling him I pulled off my top show him my tits.
"I have seen you look at these so many times. it makes me so fucking wet when I see you trying and look down my top. Do you like them up close?"
I pushed them in his virgin face and he was in shock but was not dense. He started sucking them and thanking me endlessly. I pulled away....
"Bryan, no one. Do you hear me? No one. No one ever knows this happened. If you want more fucking swear it right now!"
He could barely speak but he swore it and before he knew it I was unbuckling him and pulled out his cock and to my delight, it was like the rest of him it was big and chubby. I had barely stroked it and was about to go down on it and he popped right there and cummed all over himself.
"I am such a fucking loser. FUCK! I hate myself!" he said mortified at losing he chance to fuck me.
I looked up at him with the the sexiest eyes I could muster...
"Bryan your not a fucking loser! We are for how we treat you. I don't ever want to hear you say your a fucking looser again looser don't get this!"
And with that I started licking up his cum... making sure he saw it on my lips and tongue. I made direct eye contact and swallowed gobs of it and giggled with him as i did. I teased him about being his very first cumslut. I played with his cum and the most sex naughty ways I could think of. He was hard in not time, I didn't want him to pop premature again so i completely sucked him off and swallowed again, before riding the hell out of his virgin dick until he was a man.
That summer he was like my sexual student. I taught everything. He loved to eat me out and he spent a whole summer perfecting it. He was so eager and grateful. He was labeled the biggest loser virgin in senior year, but we secretly fucked all year, and my money is on him being the best dick in the whole school.
Bryan found his confidence. He became a lawyer, then a judge, and is not cubby anymore but ripped. By far he is the most successful in our group. I am so proud of him. And he never told anyone. We hooked up on and off, through college. But when he got his own first girlfriend I backed off to let him fly.
He was a real friend as fair as high school friends go. We loved him, but we also loved having a built in punchline for every joke that cold be told. He belonged to our group but was teased ruthlessly. To our surprise it always took our sh!t and took it well and I think that is what kept in the inner circle.
You know how mean high school kids can be and by senior year he was our token "loser virgin" group member and got ragged on every day not only for being a virgin but not being able to likely change that anytime soon. But the joke was on them, he was not a virgin. I know that because I had secretly taken his V-card during the summer and he never told anyone because I had a boy friend also in our circle of friends. I am not saying i was the hottest girl at school but I was up there and well sought after and a million miles out Bryan range. Nobody would ever suspect he got to fuck me.
Most of our friends were gone on various summer adventures. May family could not afford that and Bryan was always hanging around. One night when no one was home I smoking up in my basement and Bryan I think started to get a contact high because out of no place he blurted out
"Rylee, I have loved you since we were kids. I know you'd never feel the same. I don't expect you too, I actually understand your with Jason, and you deserve someone like him. I just want you to know, before school ends next year, you will always be my first crush."
Maybe I was high, maybe i was horny, because Jason had been gone for weeks. Mostly, I saw the look in his eyes and I knew right then and there I was going to pity fuck him. I took my last hit on the puff and saying nothing, walked over to him and got real fucking close in his space. I loved his confusion and i think he actually trembled in excitement of being that close to me.
I brought my body into his and he felt my tits against his chubby body, i brought me lips as if to kiss him but instead, out of no place I pushing him down hard on my couch and straddled him. And straddling him I pulled off my top show him my tits.
"I have seen you look at these so many times. it makes me so fucking wet when I see you trying and look down my top. Do you like them up close?"
I pushed them in his virgin face and he was in shock but was not dense. He started sucking them and thanking me endlessly. I pulled away....
"Bryan, no one. Do you hear me? No one. No one ever knows this happened. If you want more fucking swear it right now!"
He could barely speak but he swore it and before he knew it I was unbuckling him and pulled out his cock and to my delight, it was like the rest of him it was big and chubby. I had barely stroked it and was about to go down on it and he popped right there and cummed all over himself.
"I am such a fucking loser. FUCK! I hate myself!" he said mortified at losing he chance to fuck me.
I looked up at him with the the sexiest eyes I could muster...
"Bryan your not a fucking loser! We are for how we treat you. I don't ever want to hear you say your a fucking looser again looser don't get this!"
And with that I started licking up his cum... making sure he saw it on my lips and tongue. I made direct eye contact and swallowed gobs of it and giggled with him as i did. I teased him about being his very first cumslut. I played with his cum and the most sex naughty ways I could think of. He was hard in not time, I didn't want him to pop premature again so i completely sucked him off and swallowed again, before riding the hell out of his virgin dick until he was a man.
That summer he was like my sexual student. I taught everything. He loved to eat me out and he spent a whole summer perfecting it. He was so eager and grateful. He was labeled the biggest loser virgin in senior year, but we secretly fucked all year, and my money is on him being the best dick in the whole school.
Bryan found his confidence. He became a lawyer, then a judge, and is not cubby anymore but ripped. By far he is the most successful in our group. I am so proud of him. And he never told anyone. We hooked up on and off, through college. But when he got his own first girlfriend I backed off to let him fly.
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