It was Friday night football and our high school team just lost a very close game. You see I'm the head cheerleader and my brother Mac is the quarterback and captain of the team. Seems stereotypical but that's high school. Well he was definitely bummed because he threw the bad pass that could have won the game but put it in the dirt 5 feet in front of his best friend and tailback of the team in the end zone. I wanted to “cheer” him up really bad.
We have been going out for over a year now, since we were juniors. I really liked him. Late last school year after a dance we got in to some heavy petting and I let him slip his hand in my pants for the first time. It felt great but he was definitely clumsy. I guess I was too as I pulled his dick out of his pants and saw it for the first time. It looked wonderful to me. He instructed me to move my hand up and down on it. As he finally found the entrance to my now wet opening with his finger I complied and started stroking his member.
At the time I thought this thing was the most beautiful dick ever, not that I had seen one before. It was about as long as my hand and my hand fit nicely around it so his dick head just stuck out between my finger and thumb. I could see it disappear every time I brought my hand up. Unfortunately just as I started to feel some stirring in my loins, he came. I was glad to please him . My mother always encouraged my to talk about sex with her when the time came and so I told her about my encounter and how I felt. Mom said try to avoid having actual intercourse (mom uses such big words) as long as you can. You can use alternatives such as oral sex or what most call blow jobs or continue to give him hand jobs. I said but what about me. She said your brother should return the favor and go down on you as well. You two learn this and you'll not risk pregnancy.
Well the next time I got into some petting again he stuck his hand down my pants and when I pull his dick out I stroked it and decided if I was going to get some relief from my sexual tension then I'll learn to give a blow job. My girl friends said their was nothing to it and I'll enjoy it. I put my mouth over it and slid it easily all the way in. My brother went crazy. He came in about 10 seconds and I coughed and spit his cum out. I liked the taste but just couldn't bring myself to swallow just yet. When I suggested that he go down on me and return the favor his said no he wasn't horny any more. Well that left me frustrated but I liked pleasing him. This went on for a couple more months until about 2 months ago I finally thought I must have release of my own burning so I told him I wanted to go all the way. He put on his rubber and slid right in to me with no problem. My girl friends said losing my cherry might hurt a bit but this felt really good. Only problem is he came almost instantly.
We did it 3 other times before this night of the big loss and every time it was the same thing, he put it in and came. Well tonight I was going to really cheer him up good. When he came out of the locker room we walked across the field and in to the town park. We sat on a bench and just kept his head down all bummed out. I told him I know how to cheer him up and laid down on the ground in front of him pulled my cheerleader skirt up slightly and revealed to him I wasn't wearing anything under it. Well he cracked a smile and I told him to take me, take me now. He just looked somber at me and started babbling about how he felt sorry for himself and his loss. Well if pussy won't cheer him up I thought maybe some head will.
I got up on my knees in front of him, pulled down the front of his shorts and put my mouth right over his half stiffened member. He got hard right away and started that familiar groan of his letting me know he was about to cum. Just then I felt someone place his hands on my ass. I was scared and jumped forward quickly my brother just grabbed my head and pulled it back in place. I looked around and it was his best friend John, the tail back. When I looked up at Mac I saw him encouraging his friend and told me it was OK, he needed some cheering up too. I was concerned but I was also very hot and bothered at this point so I figured if my brother was Ok with it so was I. John pulled my skirt up over my back and uncovered my bare ass. He said alright Mac you keep her with no panties, cool. I felt his hand exploring my very wet pussy and he inserted two fingers right up to the knuckles. This felt wonderful and I enthusiastically sucked on Mac's cock as he got closer.
Actually I was amazed at how long he was lasting, usually he would have cum by now. Now John moved positions and I couldn't quite figure what he was doing. I figured he was getting ready to mount me when all of a sudden I felt his head slip between my knees and he brought his mouth right up on to my cunt. I all but screamed with pleasure. My mother was right when she said I should be doing this instead of fucking. He licked my clit and stuck his tongue in and out of me and finally for the first time in my life I began to cum. It must have lasted a good 30 seconds and just as I started to come down from my climax, Mac finally released his load in my mouth and for the first time I swallowed him right down and it was good. John climbed out from under me and pulled his dick from his pants. It was a nice one.
A little bigger than Mac's, about six inches. He moved forward and slid it right in me while I was on all fours. First time for doggy style as well. Later I found out this was a whole night of first times. John continued to plow his dick in and out of me and I was on fire again. I told Mac he better learn to eat pussy and to fuck like this or else. He just laughed. John said the only reason he's lasting this long is he already fuck his girl, Jill, just a half an hour earlier and just happened to be walking back through the park on his way home from dropping her off. Lucky for me. I thought I was about to cum again when John shoved his dick in as far as he could and unloaded. It was at that moment I realized he didn’t have a rubber on and the warm feeling of cum entering my womb for the first time was wonderful.
Mac was starting to come back to life again and I laid back on the ground and too fucked me really good and actually lasted for a whole minute. Still not long enough for me to cum again. Just as Mac finished I sat up and looked down at my very sloppy pussy and just laughed. I jumped again of the sounds of two more people approaching us. It was Bill and Bobby, the two linemen protecting Mac. I pulled my skirt down and as they walked up they said what's up boy's. Mac and John just laughed and said I was just cheering them up. Then Mac surprised me by saying hey boys, maybe you could use some cheering up too.
Well I couldn't believe what I was hearing. I did need some release and knew I couldn't talk Johnny in to going down on me with my cunt full of cum. So I said sure. Now these two boys were big. Bill was probably six foot one about 200 lbs and Billy was six five and about 220 lbs. Bobby was a neighbor boy of mine growing up and lived in town. He was going out with my best friend. Billy on the other hand was a farm boy that lived out in the country. He was always shy and never talked to me much. I knew Bobby knew how to fuck because my girlfriend always bragged him up about how he had such a big cock and knew just how to use it. Well Bobby stepped up first as I laid back down on the ground exposing my well fucked sloppy cunt to him. He said Jim and John fucked you good but you hadn't anything yet. He slipped his shorts down and revealed a big 8 inch cock that I swore would not fit in me. He positioned himself over me and started the head of his big dick into me. It was the greatest feeling I had since Johnny went down on me earlier. After a few strokes he managed to work the whole thing into me and I started to cum again for the second time ever in my life. Jimmy and Johnny was actually cheering him as I was bucking and screaming under him.
I finally came back down from my high and I could feel his balls stiffen. He pushed forward really hard and touch a place inside me never touched before and unloaded an awesome load of gizm inside me. I noticed Bobby half turning away and half staring as he wasn't sure what to think. I asked him what was wrong and he said nothing. The others laughed and said he was cherry and this was all new to him. I said awe come on we'll do something about loosing that cherry right now. Bobby said he had chances for sex before but every time he got naked with a girl she'd chicken out because of my dick size. It was kind of big and scared girls away.
She laughed and said it can't be that bad, look at Billy's monster dick and I handled that OK. Let me see it. Bobby stepped forward and I got up on my knees to pull his shorts down. When I did a bucket of cum sloshed from my cunt and on to the ground. As I pulled his shorts down to his ankles this most wonder monster dick sprang forward at me. It was only half erect and hung half way to his knees. The other three just gasped and Jimmy spoke and said you can't fuck him, he'll kill you. I said now Jimmy I made a promise to take his cherry and I will. Besides you let your other friends fuck me, Bobby should too. I realized just then what a slut I became. I put my mouth over the head of Bobby's dick and it barely fit.
I put both hands on his shaft and still had lots of room to run it in and out of my mouth. Bobby's dick had to be over 10 inches long and as big around as my wrist when I finally got it all the way up. I decided not let him climb right up on me like the other boys did because he'd hurt me for sure. I told Bobby to lay down and I'd get on him. Well I moved over him and had to get up on my heels to get my pussy high enough to get on him. I slowly placed his cock head at my well lubricated opening and started settling down on him. Thank goodness I was so wet and already stretched by Billy. I took probably half his dick in me until I now resting on my knees. It hurt a little so I decided to just hold it there for a while till I got used to it.
The others moved into position to watch as my pussy lips stretched around this monster impaling me. I looked up at Jimmy and told him I might love him forever but he could never do for me what Bobby is doing right now. I started moving up and down on his shaft trying to push down farther each time. I felt another orgasm building and it unleashed all over Bobby. I screamed and panted. My cunt squeezed down so hard and I was so full of Bobby that all the remainder of the other boy's cum inside me squished down over Bobby's dick and run off his balls.
I was getting tired in this position and decided it was Bobby's turn to do some of the work. I got off his dick and it made a slurping popping sound everyone could hear. I told Bobby to fuck me doggy style. He didn't know what I was talking about so the boy's said like the cows do it on the farm. That's all he needed and when I got on my hands and knees he knew just what to do. I told him to take it easy and don't shove it all in because he'd hurt me. He was very gentle and slid it half way in me. Billy now had his 8 incher back up again and was shoving it in my face. I opened my mouth and took him right in. The two boys got a good rhythm going as Bobby pushed forward I was thrust on to Billy's cock and when Bobby pulled back I too moved back. I was ready for more of Bobby's cock so I hollered back to him to give me more, fuck me harder. Jimmy and Johnny were both hard again and was jacking off to the sight of these two big boys fucking the shit out of me. I started to cum again and this time I was the one pushing back on Bobby trying to stuff as much of that wonderful meat into me as I can.
I felt pelvis bones actually spread as he finally lunged forward and put it all the way in me and I felt his nut sack against my clit and I came. He pounded me hard now and I must have came for over a minute the whole time muffled by the big cock in my mouth. My humming and moaning must have been just the sensation the Billy need as he was cumming buckets of cum down my throat and spilling out of the corners of my mouth onto the ground. Jimmy and Johnny were both getting close too and I told them I wanted them to cum in my mouth too. I now loved the taste of cum and hungered for it. As usual Jimmy didn't last to long and only offered me a few drops of his seed. He must have been pretty well spent.
Johnny pushed his cock forward and started to fuck my face which made it easier to enjoy the pounding I was receiving by the virgin cock in my pussy. Just as I was thinking this boy was lasting a long time for a virgin I heard him groan and his dick started throbbing in my cunt. He pushed all he had forward into me and I could feel his enormity more then ever then he came. I felt his thick hot juice pour into my innards and his spasming rod sent me into yet another huge orgasm. Johnny started shooting his load into my mouth but I was scream so much he cock didn't stay in and he sprayed it all over my face. Bobby just kept pumping squirt after squirt of man milk in to me and continued to do so as he withdrew.
His last few blasts hit my ass and shot over my back. Bobby rolled backwards and just sat on the ground in awe as his cherry was definitely popped. I stood up and was a sticky mess from head to toe. My pussy ached and was throbbing sore. Cum ran from my cunt like I was peeing and was running down the inside of both my legs. Yes I was worn out but was worth it. I'll still cheer hard for my team to win but secretly inside me I'm hoping for another loss so I could cheer my boys up again after the game.