Another First Time

It seems to be tradition that your first story you write is about your first experience with another guy. So, in light of that, here it goes. I know that I have always been attracted to both boys and girls when I was young. I found boys to be more challenging, though. This happened while I was a sophomore in high school. I was 15. Chuck was 16 and we met in the high school music program. Chuck was shorter than I was, at 5’9”. He was also very skinny, but not bone thin. He still looked healthy. I, too, was very thin. We were opposite in looks. I’m olive complexion and he’s very fair. I have black hair, he has blond. We hit it off pretty good, even though, our personalities were quite opposite. I first got to know him at a birthday party and from there on out, we were quite inseparable. One weekend, Chuck asked if I wanted to stay the night over at his house, then I could help him with his paper route in the morning and then go around the neighborhood and collect the monthly bill. Of course I jumped at the chance to spend the night in his room. He had his driver’s license so he picked me and we cruised around. After trying to pick up girls, like we could, we went to a drive-up at Jack (off) in the Box. He had some cash between his legs next to his crotch. I got some money out to give him, so I put it with the other cash and rubbed my hands all over his crotch. After a slight moan out of him, he shouted “you Fag!”, I said :”yeah, so are you!” That night, he got a sleeping bag out for me to sleep on his floor. He had a twin bed. We stripped to our underwear (whitie tighties) and went to bed. He woke me up at 4 to do the paper route. I said no way, I’m sleeping. He told me to get in his bed while he was gone. I gladly jumped into his warm bed. When he got back, he stripped back down to his underwear and jumped in bed with me. He snuggled right up to me and was rubbing his dick against my ass. I reached around to stroke him. I felt his dick through his cotton briefs. He didn’t want me to jerk him. He said to me: “Let me put it in” I was a little freaked out about this. I never have had a dick up my ass before. I said “no” I rolled over to face him, hoping to get a mutual jack session going. Then he rolled over and pulled down his underwear. He wanted me to put my dick inside of him. I thought I could use this opportunity to touch him. But he still had himself covered with the front of his briefs. Being disappointed, I rubbed my dick against his ass. I was too afraid to go inside. He moved his hips back and forth to meet my gyrations. I moved in a little closer so my chest was covered by his back and my mouth was near his ear. I was moaning and saying, “can you feel it” A couple of weeks later, we were at my house studying for a biology final. Every organism was an orgasm to him. I knew he was horny and thought I had another chance. I took him back to my bedroom. I had a queen-size waterbed. We laid down on it with our feet hanging over the side. We each in turn unzipped our pants, but we didn’t take them down. Just our bone hard dicks under our briefs. He reached over to touch mine and commented on how large it was. I, then, reached over and touched his. He was bigger than me. The moment was so hot, two horny teenagers wanting to get it on. We hadn’t done much more, when my parents came home. We quickly composed ourselves and went back to “studying.” My parents soon left again, almost as if they knew what was going on. They hardly ever leave later in the evening. Chuck and I returned to feeling each other through our jeans and underwear. This time we managed to get our pants down to our knees. We both just laid there and slowly stroked each other, asking each other how it felt. I don’t know who was enjoying it more. I loved being stroked by him, while returning the favor. There was a knock at the door, I quickly ran to the door and looked through the peep hole. It was his parents. I couldn’t believe this. I was so mad. I wanted to get off with him so bad!! He left. We got through finals week with little contact. Once our last final was over, we came back to my house for the afternoon. We quickly ended up in my bed, again. He wanted to try on a condom. So I found one of my fathers, and we took turns trying it on. Our pants were down to our knees. I wish looking back that we had gotten completely naked. He asked again if I would put it in him. I consented, dying to get off with him. I didn’t know the first thing about it, so he sent me around the house looking for Vaseline. I couldn’t find any. He said it was okay and just to put my spit on his asshole. Right on!! So I’m rubbing his asshole with as much saliva as I can get out of my mouth, to my hand, to his not so virgin asshole. He rolled over on his stomach, I came up between his legs and spread his ass cheeks. I guided my dick to his awaiting manhole. He said to go slowly, he seemed to naturally relax as I gained full penetration. Wow, what a feeling. It was like none I had had before. It was hot and it felt open, except for the tight grip around the base of my throbbing dick. I could hardly contain myself. I slowly pumped his ass, feeling his tight hole grip the length of my dick. I was gasping for breath with each stroke. My moans were so loud, I was afraid the neighbors would hear. Also, I had one of those oval mirrors in my headboard, so I was really turned on by watching myself pump his beautiful white ass. I just kept saying: ”Chuck, it feels soooo gooood!!!” Just a few more strokes and I cum all inside of him. I screams with each shot “It tickles!” I just collapse my shaking body on him while I took a moment to recover. He must have been really turned on because he was still hard, and couldn’t wait to get inside of me. He wiped his spit all over my asshole and then gently went in. I was afraid it was going to hurt like hell, but it actually felt pretty good. I loved the way each stroke of his hips messaged my prostate. I could feel myself getting hard again. It didn’t take long for him to start moaning and pumping my ass faster and faster. I looked up in the mirror to watch his face. His eyes were closed with his mouth half way open. With every thrust there was a “Urghh!” Finally, after thrusting uncontrollably, he shot his load. He quickly dismounted and went to the bathroom to shit out my cum, and he told me to do the same. I saw that he was still hard, but he pulled up his pants and left. I was left there felling like some whore. Our friendship was never the same after that. Come to find out later, he had fucked most of his male “friends.”