My Initiation Into Sex

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An 18 year old gets curious.
1.6k words
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When I was 18, my dick was getting hard every 15 minutes, and I was spending a lot of time jacking off. One day while in the woods with the other guys in the gang, Roy walked off to take a piss. I went along as I had to pee also. As we stood and pissed, my dick started getting hard as we watched each other piss. I was sure I noticed his getting hard also.

Roy was 2 years older and uncut, and had to skin back his dick to pee, which fascinated me since I am circumcised. Impulsively, I suddenly reached out and took hold of his cock and held it while he finished. As he finished, I could feel it getting hard, so I started to move my hand back and forth. Roy offered no resistance, so I kept moving my hand until it was completely hard. Until this moment, I had never touched another dick. I liked the feel. It was quickly hard and full length, I estimated about 7 inches. The head was so much bigger than the shaft. I was so fascinated with the foreskin.

I don’t remember how long it took, but it was rather quickly, he began to shoot his load. The cock in my hand was pulsing and jumping and I kept jacking it off. Seemed like he shot a pint of the white stuff. When he was done shooting, he wiped his dick with his hand and put it back in his pants. Never said a word. Just walked off.

Two days later, I was home alone and jacking off so I called Roy and told him to come over. No reason was offered, so he came over in about 5 minutes. We went to my room and was playing with some of my things when I reached out and grabbed his crotch. I could feel his cock and balls through his jeans, and he did not resist. I proceeded to unzip his jeans and pull his now stiffening cock out. I was fascinated by the way the skin covered the head and how it pulled back to reveal the red crown.

The more I jacked his cock, the harder it got. Impulsively, I dropped to my knees and took his cock into my mouth. Kinda salty, but I liked the taste. Never having done this before, I only moved my mouth up and down on it, keeping my tongue out of the way.

As I moved my mouth, more and more saliva built up and I had to swallow, and that is when my tongue came in contact with the head. What a taste sensation that was, because he was oozing pre-cum. I liked that taste also.

By now, I had freed my on cock, and was busy jacking off. We are both the same size in length, but his head was 2 times bigger than mine.

Next thing I know, I am feeling his cock head swell up and the first pulse of orgasm. I didn’t know what to do, but I didn’t think I wanted that in my mouth so I pulled back just as the first shot hit me on the chin. Then another and another, finally after about 5 big shots on my face and chest, it was just kind of dribbleing out. I put it back in my mouth and cleaned it up. Wasn’t bad, kind of salty and a little bitter, but I could live with the taste. When I finished cleaning his cock off, he took hold of mine and jacked me off until I shot my load. He didn’t clean me up as I had done, but he seemed to enjoy the experience.

Once we settled down, we talked about what had just happened and swore each other to secrecy. I told him I loved the taste of his cock and even the cum. From that day on we would get together every chance we had and I would give him a blow job and he would jack me off.

One day when we were exploring this new found sex game, Roy had me turn around and we got into a 69 position. By now we had shed all of our clothes and no longer just did it through the fly of our jeans. As I was sucking his cock, he started to play with my asshole. First a finger lightly touching it, then he tried to insert the finger. Since there was no moisture, it didn’t feel very good as it went in, but I liked the sensation once he had it all the way in to the knuckle.

As I sucked his cock, he told me to stop and got above me while I was still on all fours. He leaned over and spit on my asshole and then put his finger back in. Next thing I know he had 2 fingers in there, then 3. Soon he was moving his fingers in and out, and I was loving it, but felt like I had to have a bowel movement. So I went to the bathroom and moved my bowls. When I came back, after I had washed my ass real good, he spit on my asshole again and resumed the fingering of my rosebud. I was really loving the feeling, and silently hoping he would decide to shove his cock in there.

Next thing I know, he spit on his cock and replaced his fingers with his cock. As the head went past the sphincter, I experienced pain as I had never known in my life. He just held real still because I was screaming to TAKE IT OUT! TAKE IT OUT! In a minute of so, the pain subsided, and his cock was still inside my ass. Just the head, but still there. I tried to adjust to it, but it felt like I had to go to the bathroom again. I told him that, but he started to push his cock deeper instead of pulling it out. Slowly, he inched it forward until I felt his belly against my ass cheeks. Now I really felt full. We just stayed that way for a minute or so and then I pushed back against him as though trying to get more of his cock into me.

Next he started to back out, slowly, just as it had gone in. When he had it all the way out, except for the head, he spit on his shaft again and started to push it back in with the added lubrication. IT FELT SO DAMN GOOD!

Soon he was fucking me so hard and so deep, and I am squeeling like a pig, it felt so good. Next thing I know, he is dumping his load in my ass. I can feel every vein in his cock and the head is expanding and pulsing and I can feel the cum hitting the walls of my intestines. Nothing in my life ever felt better than this. When Roy stopped pumping me full of cum, his cock softened, and he removed it. When the head popped out, I shot my load all over the bed. I think that felt better than any of the getting fucked part.

What a day. I had tasted cum, and I had been fucked until I could hardly stand. And I loved every bit of it. In fact, I could hardly wait for our next session.

To my surprise, it wasn’t over yet. Danny, also 2 years older was outside my window and unnoticed by either of us. He simply let himself in the back door and when he appeared by the bed it nearly scared us both to death.

CAUGHT, was our only thought. To my surprise, he simply pulled his cock out of his pants and it was 10 inches long, and half again the girth of Roy’s cock. Most of all, the head looked like a purple plum.

First he shoved it into my mouth and I sucked and sucked. His pre-cum was as plentiful as my cum when I shoot. It just ran in a steady stream into my mouth and I swallowed as fast as I could. I was really sweet tasting. Then he pulled it out of my mouth, got behind me and started shoving it up my ass. Talk about hurt… Roy was nothing compared to this. Since my ass was already loose from the fucking I had just had, and full of cum, it went in relatively easy, but the pain was blinding. He didn’t wait, he just started fucking me.

Long, deep, slow strokes. In a minute of two, I was pushing back to meet his thrusts. He fucked me and fucked me and fucked me some more. Roy in the meantime was getting hard again watching so he went and washed his cock off and came back and shoved it into my mouth. Now I was getting fucked from both ends. A rhythm was quickly established, and I was in heaven. Roy soon shot his load in my mouth and I was swallowing as fast as I could, but lost some.

Meanwhile, Danny was still fucking me with those loooong slow strokes. Gawd! Could anything feel better than this? After about 20 minutes, Danny began to quicken the pace and I felt that plum swell up and spit the cum so far and so deep in my bowels. When he finally stopped cumming, he pulled it out and I unloaded another load on the bed without anyone touching my cock. Seems that the removal of the big head is better than any part of the fucking.

When we recovered and rested, he said he was going to tell his brother Johnny. Now I was worried, because I didn’t understand why. Then he told me he and Johnny fuck all the time, and Johnny has a bigger cock than his.

I was now afraid I would be ripped apart with anything bigger than Danny, but after what I just experienced, I was willing to give it a try. But that is another story.

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3 Comments
TeenTopTeenTopalmost 5 years ago
"It felt so damn good"

18 is far too late to get curious, but the initiation by an older boy is accurately described as the most natural way to gay sex. Getting fucked from both ends on the first occasion must be an amazing experience.

gaypenisgaypenisover 6 years ago
sex

I loved your story it was so hot got my damn penis so hard while I was reading this story that I had to start masturbating

AnonymousAnonymousalmost 17 years ago
Mad3 me cum!!

thiz story waz good which by da way made me jack off all da way!! good story n hell yea it feels really good to do a big cock i know from personal experience!! R u gay cuz i am well if u r hit me up 702911 i live in vegas!!

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