My first Time_(101)


The first time it I had sex with another was when I was in middle school.

One day while I was at my friend Mark’s house, only his brother Jacob(20 at the time with a 8in penis), him and I were at the house his parents had gone out of town and would be back the next night. We played video games for a while then he asked me if I wanted to play truth or dare, I said ok.

We played for about 8 or 10 min doing silly boy things and messing around. Then one turn when i said dare he told me “I dare you to take off your shorts and show me your underwear”, I was a bit surprised at his request but did so, so I wouldnt lose. It was his turn and he chose dare and I told him “Okay, I dare you to take all you clothes even your underwear” for a moment I thought he wouldn’t do it but to my surprise he did he took off all his clothes.

I was amazed by his body and even more by his cock and stared at it for a bit, guess he noticed, because when I chose dare again he told me “I dare you to take your clothes off all the way too and I double dare you to touch my penis”. I took off the rest of my clothes quickly, then slowly went toward him and placed my hand on his penis marveling at it. I then told him “Okay now touch my penis too” he did and he slowly started to rub it up and down. I felt so good from it, so I started doing the same to him so he too could feel good. I looked at his wennie while we were rubbing each other making each other feel good.

We continued this for few minutes. He then asked me if I wanted to try something that he had seen on the internet seen he said I said yes. He told me to lay on his bed and I said okay. He then got on top of me and put his penis by my mouth and put his mouth by my penis. He told me to open my mouth and suck his penis, I take it in my mouth and begin to suck it slowly at first like sucking on a popsicle. As gaziantep swinger I start sucking he starts too, starts bobbing his head up and down on my penis making me feel good, as I make him feel good.

We’re so caught up in sucking each other, that we don’t notice his older brother watching us sucking each other. He’s at the door only in his underwear stroking himself slowly and steadily. We stop after he lets out a deliberate moan from seeing us sucking each other, we are shocked and scared afraid he will tell on us. But at the same time im staring at his rock hard cock. He notices and tells us “Ok Mark you boys have two options, 1.I tell our parents and your friends parents or 2. I put my dick in your friend’s little ass.” Mark then tells me worried “Derek if our parents find out we’ll be in alot of trouble. Then they won’t let us see each other anymore, just let him put it in your butt. He’s done it to me a few times before it doesnt hurt that much after a while.”

I look at Jacob and say “Okay I guess I’ll do the second option, but you promise it wont hurt Jacob?”, “I promise it won’t hurt that much, wait here so I can get a condom” he says. I ask Mark “Mark what’s a condom?”, he replies “Its something you put on your weiner to have sex with so he can put it in your butt”. Jacob comes back with a condom and lotion(more than likely lube but I thought it was lotion at the time) he tells me to lay on the bed while he puts the condom on. He holds my legs wide and says “What a cute little rosebud you have Derek, I’m going to enjoy taking it from you”!

Jacob then put his mouth next to my butt and starts to rimming my hole it tingles but feels good, my little penis starts geting hard. He sees my hard on and starts to lick my hole faster and harder I saw start to feel tingly as he licks my rosebud. He finishes and start to rub the lube on my hole, he does this till his finger slides into my butt. I wince as his finger enters me unexpectedly, he keeps it in for a little bit and pulls it out and starts massaging again but with two fingers this time. He repeats his action as he did the first time and pulls his fingers out of my bum.

Jacob then tells me “Okay Derek, get ready I’m going to pop your cherry now. Just breath slowly and dont move ill do the moving kay.”. “Okay Jacob, do you promise it wont hurt?” I say one more time, ” Yes, I told you it wont hurt that much Derek” Mark says for him as he’s sitting next to us on the bed rubbing himself slowly. Jacob grabs the lube and lubes the condom up once more before aiming it towards my hole. He places it next my bum and slowly starts to push it in, it hurts alot almost burning

Jacob tells me to breath and relax.

The head of his penis is pushing into me and slowly start going inside my bum. He pushes a little more till finally it slides in feeling like fire. Jacob stay still for a bit allowing me to get used to his girth. He then push a bit more sliding 4 more inches of his penis inside of me. He pushes till the rest of his 8in penis slides into me with ease, once more he stays still and telling me to breath and relax.

The pain from his dick being in my bum starts to fade and the good tingling sensation comes again. Jacob starts to pull in and out of me slowly at first but then gradually going faster eventually making a clapping noise with our bare skin. As he’s deflowering me Mark is stroking his hard on a bit faster as well, he then gets an idea and tells me ” Hey Derek suck my penis while my brother is inside you!”

I’m in such pleasure that I take his penis in my mouth without a second thought once again. Mark and suck each other as Jacob fucks me in my little hole building my pleasure and sending me into extesy. After 2 min Jacob pulls out and says “Forget the condom, I’m going to bareback and breed your sweet hole Derek!”

Jacob enters my hole in one thrust giving me that tingling sensation and making me feel good. He rams my bum with his long hard cock and makes me feel it in my belly. Jacob rams me and gets me close to what I didnt now at the time was an orgasm. The tingling sensation starts building up and I stop sucking Mark and say “Jacob stop I feel like Im going to pee” but he replies that it’s okay to not worry.

I continue to suck Mark as the sensation builds up even more eventually Jacob’s cock rams me once more and I start to cum in Mark’s mouth, my bum tightens sending Jacob to a heavy orgam as be ram into me once more and cums deep inside of me filling me with his hot sperm. Almost the same time I suck on Marks penis hard and he orgasms into my mouth his cock sending ropes of cum into my throat, tasting sweet and salty at the same time. We stop and stay still for a little while Jacob pulls his now flaccid penis out of my bum and lays next to me and Mark. “Derek”, he says ” You’re the best piece of ass I’ve ever had little buddy, I hope you liked it”.

“I really liked it Jacob can we do it again.” I reply weary. “Sure but later little buddy, im kinda tired lets sleep for now” he says as he starts to fall asleep. “That was awesome Mark I didnt know boys could do that to each other”, ” Yeah, that was awesome Derek but, remember we cant tell anyone or we’ll all get in a lot of trouble” he says. “Ok I won’t.” I reply. As Jacob’s cum starts to slowly trail out of my bum Mark and I fall asleep holding each other as Jacob reaches over to hug us both and fall asleep.

Well thats the story of the first time I has sex and sucked another boys penis, I remember it very well because I still had sex with Mark and Jacob up until last June when they moved away. Hope you liked it.

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