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First Time Cumming Masturbation
I was thirteen years old and had been what I thought was cursed with a rather large cock because in the showers after gym class the other guys would make fun of me. I would hang down farther then the rest of the guys and the head of my cock was just huge even when it was retracted inside of me. I had been masturbating for some time by then but had not been able to bring myself to orgasm. Part of the reason was that I was so inexperienced in knowing my body and I had an eight inch cock that was so thick I could barely get my hands around it so my hands would get tired of stroking it before I could get to that point. My parents had gone to their yearly retreat to Las Vegas by themselves and had left me with my sister who was eighteen and had just graduated from high school that summer. It was July and very hot and we had no air conditioning. My sister was trying to talk me into going over my friends house one night which was just a neighbor two doors down. I knew that she was planning something because Mom told her not to let me out of her sight while they were gone. Before leaving I overheard her talking on the phone that the party was at our house. I knew that she was going to have a few of her girl friends over to hang out since my sister wasn't really a wild girl at the time. I also knew that the girls she was going to have over were all very hot and I would have fucked anyone of them at anytime. I got my stuff together and played along with her leaving as if I didn't know a thing. When I got to my friends house I told him I was only staying for a little bit and would be back later. I waited until dark fell to make my way back to my house, I had left my bedroom window open since it was so damn hot so I figured I would just climb in and see what was going on. I heard them partying and playing drinking games and laughing as I put my head to the door. I soon heard one of them say they should all go skinny dipping in our pool because it was still hot. That was the moment I was waiting for and scurried out the window as fast as I could to make my way to the changing room next to the pool. We had a small changing room with a couch and some towels and stuff near the pool that also had a shower in it so I knew that was the best place to get a glimpse of some naked woman and not get caught. I ran to the room and waited for them to come out and strip down the whole time with such a raging hard on from just knowing I would finally get to see a real naked girl. I had seen plenty in some of my dads playboys he hid in the garage and had jacked off to the pictures but had never been able to bring myself to cum. It didn't take long for them to get out to the pool and start taking their clothes off, they had left on one outside flood light and since we had allot of trees in between our houses no neighbors could see what was going on but I had a perfect view of everything going on. I already had my hard cock out by the time the last one was still getting undressed and was stroking it kinda slow and soft. I watched and touched my cock while they jumped in and swam around and laughed and played for a little while sweating my ass off the entire time. My sisters one friend who I just adored and was in total lust with soon got out of the pool and sat just under the flood light on one of our lounge chair, the other girls including my sister were now sitting on edge of the pool talking. I was trying to stay so quiet as not to get caught but I felt compelled to keep pulling on my cock while staring at these naked girls. They started talking about their boyfriends and how big their dicks were and what it was like giving head to them as well as fucking them in different places. My favorite girl was laying on the chair and started to rub her belly then I saw her hand go down to her crotch. Because the other girls were sitting with their backs to her I could see her start to rub her pussy and kinda moving her hips around. I was in sheer pleasure watching that and was just rubbing my cock as if I was inside her, I could feel the pre-cum on the head of my cock every time I would rub it. My hands were starting to get a little tired by this point and I was so hot in that little room that I just had to stop for a moment and rest while they talked about getting fucked and giving head. I saw them all get up and grab some towels and start to head back into the house so I knew that this was my chance to finally get off since I could feel some sort of tension welling up in my stomach but wasn't sure if that was what I was striving to achieve or not. When they all went into the house I pulled my shorts off and let my huge eight inch swollen cock free so I could have my way with it. I began stroking it pretty feverishly just trying to get something to happen only to have my hands become ever more tired but I did not stop since I knew I was close to something happening. In my feverish attempt to bring myself to total pleasure I had not noticed the girl who was touching herself had come back out to the pool and had walked right in on me in the changing room. When I looked up and saw her staring at me I was so shocked and scared I didn't even try to reach for my shorts or try to cover up at all. She was looking at my boner with a huge smile on her face and when I looked back down at it you could see my heartbeat in it because it was bouncing up and down. I started reaching for a towel when she said to me she wanted to watch, I was so scared I could barley talk when I told her that I was afraid she would tell my sister. She told me she wouldn't if she could watch me make myself cum, but I had to tell her that I have never been able to get off. She kinda snickered and asked me why not so I told her the truth that my hands would get to tired before I could make it happen. She then began to tell me that her boyfriend had a pretty large cock as well and I already knew that since I heard the conversation they were having earlier. She told me to use both hands and rub the shaft but to work on the head most of the time and that would work because thats how her boyfriend did it. I asked her about the other girls and she said they were getting changed and drinking some more and that we were safe because she only came out to shower off the chlorine. I said Ok and began jacking off while she watched with a huge smile on her face the entire time just looking at her naked body and seeing her pubic hair glisten in the shallow light from the pool deck. She started touching her tits and rubbing them while telling me how hot it was to watch a young guy beat off in front of her, I could smell a musky odor and wasn't sure if it was coming from her or not until I could see some drips of juices starting to run down her leg, she began to rub her clit and moan a little bit which made me stroke my now hugely swollen and very red cock even faster. My arms began burning very badly and I could feel some sort of tension well up in my stomach but I had to stop, she asked why I was stopping and I told her that my arms were hurting so she leaned over and grabbed my cock. She said she would help a little bit while my arms rested but I could never tell anyone so I replied as long as she didn't tell either then that was alright. I was so horny and couldn't believe that I actually had a girl touching me and my head was just swimming with all kinds of thoughts. I asked her if I could just stick my cock in her for just a moment to see what it feels like and she said no but she would let me know what it kinda felt like. She got on her knees and to my surprise she put the head of my cock in her mouth and began sucking on it and licking it. I couldn't believe how good it felt and when she would lick my balls which were hanging down low and very soft I would shudder from the warmth of her mouth. She did this for a little bit until she took my hand and put it back on my cock to start rubbing again, That feeling was becoming so intense in my stomach and now it was moving into my groin. She kept telling me how badly she wanted to see me cum while I was jacking off in her face and she would touch my balls gently which sent waves of pleasure up my body every time. The burning in my arms was so bad but I would not stop and I didn't even really notice it that much. The musky smell coming from her was now so heavy in the air and I hadn't even noticed that she had two fingers inside her just plunging in and out. I knew I was close to cumming by this point because my legs were tensing up and I was breathing so heavy while sweat just rolled off of every part of my body. I actually thought I may be hurting myself because the feeling in my stomach and groin had become so intense that I couldn't move, Just when she started rubbing my balls I could feel allot of pressure building up. She began to say something but I hissed at her that I think I'm cumming and just then I released a rather surprisingly huge amount of cum, it shot out so hard that it went across a ten foot room and splattered halfway up the wall. That was the first shot and the rest just kept cumming out over and over with every shot making my legs weaker and weaker. She kept rubbing my balls while I stroked my cock back and forth with every pulse my body was making the milky white ooze just kept blasting out of me. I was so shocked and wiped out by now that I had to sit down before I fell down, she asked me if I was alright and I could barely get a word out but managed to say "is that what cumming is". She replied yes and that was allot for a little guy like you but you have a big cock, she cradled my balls which had shrunken up inside me and told me that I must have drained them both since there was so much cum everywhere and they retreated back inside me. I could barley see anything because the sweat was in my eyes but I could smell her pussy juices which kept me hard. She asked if I was going to jack off again since I was still pretty hard and I told her I didn't know if I could right away but when I was ready would she be willing to help me again. She laughed and said I didn't need anymore help but if things worked out she would be happy to watch next time. I tried to blackmail her by telling her I would tell my sister and her boyfriend what had happened but she trumped me by telling me she would tell my parents that I was hiding in the pool room watching the girls. I watched her take her shower while I played with my semi hard cock and we said good night to each other while she went back into the house. I made my way back to my friends house not telling him a thing about what had just happened and went to sleep with such ease that I had never felt before. That night gave me plenty of thoughts to jack off to many many times and each time it became easier to get the cum out of my cock. I never did jack off in front of her again but I always thanked her and thought of her almost every time I would pull on my cock. I learned that I didn't have to stroke the entire length of my dick to get it to spout off and I could get it to spew faster and faster every time I would try. I had no more problems in the locker room and shower with the other guys making fun of me now knowing that the girls were gonna like my cock and I knew how to make it work!