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 boy friend Jim 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 like this boy. 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 boy friend 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 boyfriend 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 my 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 loosing 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 quick my boy friend 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 Jim 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 boy friend was Ok with it so was I. John pulled my skirt up over my back and uncovered my bare ass. He said alright Jim 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 Jim'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 figure 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, Jim 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 Jim'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 my Jim 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 a far has he could and unloaded. It was at that moment I realized he did have a rubber on and the warm feeling of cum entering my womb for the first time was wonderful.
Jim 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 Jim 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 my Jimmy. I pulled my skirt down and as they walked up they said what's up boy's. Jim and John just laughed and said I was just cheering them up. Then Jim 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.