Losing it

Gay
2006-05-16

    When I was about 15 years old I experimented with one of my friends. We jacked each other off and we both gave each other blow jobs. When I was around 16 years old my friend had just broken up with his girlfriend and was having a  tough time with it so I thought this was a perfect opportunity to experiment some more. I told him I wanted to suck him off and let him cum in my mouth, to make him feel better and, of course, he agreed. He layed down on the bed and pulled off  his pants. I wasn’t to sure if I wanted to suck him off but seeing his dick convinced me. He was six inches long and thick, very ,very thick when he was hard. I got down on my knees and softly held his dick in my hand making him shake a little and making his cock grow in size. I started to lick my way up and down the shaft making it wet. It tasted a little salty but still good. I then licked my way up to the top of his cock and slowly took the tip into my mouth. I sucked my way up and down, only a few inches in my mouth at first but I slowly got use to it and had most of his dick in my mouth. It didn’t take long before he was slowly bucking his hips against my face trying to get more in me. I knew what wanted so I went down all the way and felt his dick slide down my throat. I didn’t choke and loved the feeling with my face pressed down into his pubs. I started to play with his balls and this pushed him over the edge.

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   I could feel his hot cum shoot down my throat. I backed off a little and held the head of his cock in my lips, letting him fill my mouth with cum. I wanted to swallow it all but decided to suck his cock a little more with his cum still in my mouth. After about two more minutes of this I swallowed it all and loved it. He then thanked me and went to sleep, which is exactly what I wanted. I layed down on the floor and jacked off thinking of what had just happened. I felt a little weird but I know that I wanted more… well his parents weren’t home the next day at all so we decided to take a shower together. I got down on my knees again as soon as we were in the shower and took his soft cock into my mouth. After he was hard and close to cumming I stood up and told him I wanted him in my ass. He nodded his head and I bent over sticking my ass in the air. He grabbed the conditioner, poured some on his cock and into his hand rubbing it up and down over my asshole. Having someone else touch my hole made me jump and quiver. He then slowly walked  up close behind me moving his cock and placing it against my lubed up ass. I jumped and clenched up telling him to push. He pushed against my asshole trying to break his way in but it hurt so bad that I couldn’t take it.

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   I moved away from his dick and told him to give me a sec.

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we tried three more times but he could not get in. I then said we should jack each other off at the same time instead of letting him fuck me. He said no and pushed me down on to my knees and shoved his cock into my face. I looked up into his eyes and said I’m sorry it didn’t work but if all he wanted was a blow job he could have just asked. He wasn’t mad just horny and I knew that so I took his cock into my mouth quickly and let him fuck my face instead. Having someone fuck my mouth felt so good I came right there, only stroking my own dick a little for help. He said he was going to cum so I pulled my mouth off his dick and wrapped my hand around it, jacking him off and letting him shoot off on my face. We got out, dried off, and went and hung around the house, playing video games, eating and just chillin’. we never spoke of it. It was really cool how we acted, like nothing had ever happened.         So about a year later with no more experimenting in between that time we both went to the same party at a friends house. There were only about 7 people there and it was really fun. Well at about 1 o’clock at night everyone was going to sleep. People slept in the living room but I went to sleep in a separate room.

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   I couldn’t sleep and was alone so I started to jack off. About 15 seconds after I started my friend I had fooled around with so many times before walked in. he was bored because he couldn’t sleep. Well I was awake and hard so we started talking about sex and stuff like that. He then got up and said it was hot and took off all of his clothes and layed down under the fan with his semi-hard dick pointing towards me. I then remembered that time that he let me suck him off and wondered if he wanted more. I took off my clothes and lied down showing my semi hard dick off. Again he is 6 inches and so, so thick, and as I remember rightly was extremely hard to get my mouth around. I am 7 and a half inches long but no where near my friends girth. So lying there I bluntly asked if he liked the blow job I gave him about a year ago and he said yes. I had to only think for a moment and decided, yes, I wanted to try more stuff again and maybe he could get his cock in me this time. I asked if when we fooled around he was close to getting his cock inside of me and again he said yes. So I simply asked if he thought he could get in with more lube. He said maybe, so I told him if he found some lotion or something like that we could try it again. He wrapped a blanket around and left.

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   He came back within minutes with a bottle of aloe vera in his hand.

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He set the bottle down, locked the door and let the blanket fall to the floor exposing his hard dick. I decided I was going to make him really hard so it would be easier to get in. I crawled over on my hands and knees to where he was standing and started to play with his dick. I was slowly stroking his cock and then I moved my head closer and started sucking on his balls making him moan a little. I then took his cock into my mouth and sucked as hard as I could only  moving my head a little bit that whole time. I just held his dick in my mouth for about 15 seconds and then looking into his eyes I told him to fuck my ass.   I got up and went over to the bed sticking my ass into the air. He grabbed the bottle of aloe vera and rubbed it on his cock and up and down the crack of my ass. The gel was cold and make me shiver but having his fingers on my asshole was the main reason I was shaking. Then he slowly pushed one finger into me loosening me up and making me squirm. He asked me if I was ready and in a very feminine voice I told him that I was. He stood behind me and put one foot on the bed. He got up close behind me and put his cock against me asshole. I told him to fuck me and with that he flexed as hard as he could and slowly pushed his hard cock into my ass.

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   It hurt really bad but I just kept telling myself to relax. He was being nice and only pushing a little in at a time, sliding out and pushing a little more into me. After 5 minutes of the slow fucking it felt great and I told him to go faster. He started pumping into me faster and faster deeper every time until he pushed all the way in and held it there making me squirm and push back against him. I was moaning and whining telling to fuck me more when he started up again, pounding my ass so fast. I told him to stop and lie down on the bed, once he was there I squatted over his dick and slowly let him impale me, ramming his fat cock into me. I was soon bouncing up and down on his dick, sliding down balls deep. He said I wasn’t going fast enough and told me to lie on my back. He then made me grab my legs and hold then up against my chest. He quickly shoved his cock back into my ass and started pounding away. He grabbed my cock and started to jack me off at the same pace he was fucking me in the ass. It felt so amazing I almost came right there but stopped myself because I wanted to enjoy it. For 10 more minutes he fucked me like that; he told me he was cumming so I let him stradle my chest and fuck my face until he came. I jacked off while he did that and shot my load all over my stomach. We both went to sleep and never spoke of it again.

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   I will never forget that night, the night I lost my anal virginity.  .