What a Night for a Virgin!

by Oz I was about 13, I went over to my best friend's house for a sleep over. His parents had decided to go away for the weekend and between my parents and his, they thought that we could take care of ourselves! Well, after we got settled in, Jack, his real name, brought out his stash of prono mags and tapes. I had gotten a bunch of my dad's Playboys. We sat on his bed for hours just looking at the pictures and watching each other get hard. After a few hours, Jack asked me if I knew how to jack off. I told him no. Then he offered to show me. He took off his underwear to show me his cock. It was the first time I had seen a real cock in person. He spits in his hand and starts to stroke himself. As he is doing this, I'm getting harder than ever. He then tells me to take my underwear off. I followed his orders. He then grabs my young hard dick. It felt like a flash of lightning had hit me. As he slowly stroked me, I had the most wonderful feeling overcome me. Being rather hairless at the time, the friction is the thing I most remember. I finally came with an incredible volume! As Jack was licking the cum off his hand. He asked me if I would like to try it on his dick. I of course said yes. If timidly grabbed his dick and started to stroke. He had a lot more hair and I remember it felt exciting to stroke him. He started to cum all over the sheets and my hands. Then he ordered me to lick his cum off my hands and his dick. His dick was the most tasteful thing I had ever known! The rest of the night, we spent jackin off to all of the prono tapes and talking about sex. Late that night, Jack reaches over and starts to suck on my dick. I got hard the instant I felt his breath on my dick. He starts to slowly circle the base of dick with his tongue, slowly moving up the shaft. When he reached my head, he quickly took my whole dick in his mouth. Let me tell you, that is one of the most intense sexual feelings I know! He keeps sucking on my dick until I'm about to cum, again! He then stops. Pulls me close and kisses me on the lips! It was incredible. I started to stroke his dick, kissing him on his chest and finally reaching his dick. Not being as experienced as Jack was, I could not do that little trick he did to me, but I slowly took his dick in my mouth as far as I could. I made him come, the taste just kept me sucking harder and harder until Jack had to pull out for the pain! Then with a grin, he turns me around and makes me bend over on the bend. I had no idea what was about to happen until I felt his tongue circling my asshole. It was even better than being blown! Jack then tells me to relax, I feel something up my ass. The pain was incredible, I thought I was going to die. And, he kept pushing it in! After a minute or two the pain went away. The Jack started to slowly pump me, slow at first and then faster. I think I came before he did, I just can't remember. We rested for a few minutes. My ass was real sore. So I decided that I would have to return the favor. I got my self up and started to rub his asshole with my hand. He starts to moan so I figured that I was doing it right. I then thrusted my dick up his ass thinking that he would scream out like I did. He just moaned and ordered me to go faster and deeper. I remember that he came first. I fucked him a bit more until I had the orgasm- it was amazing. I collapsed on top of him. Jack looked at me and started laughing. Come to find out, his brother had been fucking him for a while. But that me dick was bigger and I made him cum a lot more. The rest of the night, we just laid in bed watching pronos and trying to make each cum in different ways. What a night! That was my first and only experience with a man. Even my wife doesn't know about that. Jack and I haven't talked in many years. But every now and then, I think about that night. I'm a happy 28 year straight, married guy who loves women. But every now and then I think about what it would be like to fuck another guy!