0 comments/ 135511 views/ 15 favorites Cheering up the Team By: Dr. Scott 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. 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. Cheering up the Team Ch. 02 Chapter 2: Off to College My husband Jimmy and I finally graduated high school and we are now in our freshmen year in college. I just had our twin boys and they are beautiful. Wait...I need to catch you up from my last story. You see that fall of my senior year Jimmy and I got pregnant. That summer after graduation we got married. We are young but thanks to Jimmy's scholarship I helped him get, we are well cared for by the college. We have a nice place to live, both tuitions paid for and a nice expense account to live off of. When I first told Jimmy about missing my period and thought I was pregnant he didn't even go crazy or anything. We intended to marry after school anyways, just not so soon. The twins just made marriage come early. It wasn't until they were born however that it was obvious that they were not his. We love each other dearly and the outcome won't change a thing. We'll raise them as our own just the same. You see my first-born twin was caramel colored just like his friend Johnny and the second was a big strapping red head like his other friend Billy. Apparently on that night of firsts I already told you about in the first story I got pregnant by two fellows other than my Jimmy. (Better swimmers I guess) Anyways we are here at college with the good life. I forgot to tell you how I got Jimmy the scholarship? You see as the high school season went on it was beginning to look like our team was going to make a run for the State title. We went on to win every game the rest of the season. We even beat that team that beat us in regular season during the playoffs. College scouts started looking at Jimmy and some of the other boys real hard. Us girls in the cheerleading squad were glad for our boys. One night after cheer practice in the locker room my best friend Jill, Johnny's girl, said we have to do something to help make the boys go all the way this year. Another girl set the mood by saying, "yeah, if I go all the way with my boyfriend he'd win the moon for me" Then Jill said "That's it. If the boys win the state championship we should all make sure all the seniors get laid" and laughed. Jimmy had told Jill about that one night adventure with the me and the other boys but she never let on to me that she knew. I wondered if she was ever pissed I fucked her boyfriend? Well anyways after some reservation all 12 of the girls on the squad agreed that if we took states that it was a deal. Jill told Johnny and he told the team and when it got back to the girls they all seemed pretty excited. Four underclass cheerleaders had some concerns. I think they were cherry. As they won play off game after play off game it looked as though we'd have to follow through with our deal with the boys. I was very excited and hoped I could have another shot at those same friends of Jimmy's from my first gangbang. The day of the state championship was here and the underclass girls came to me and told me they just couldn't do it and chickened out. Oh well, that still leaves 8 of us and their were only 12 senior boys. I could do 4 myself leaving the other girls not much to do. We all cheered our hearts out during the game. Myself, I cheered secretly for more reasons than a state championship. The boys had a great game and won by a narrow victory. All the girls looked at each other started to get worried. The van ride home was very quiet until Jill broke the ice and joked "Come on girls, it will probably only take a few minutes knowing the teenage boys" Jill told me she did the assistant principal, a young 28 year old man during her junior year. She said teen boys don't know anything about sex the way a real man did. I should have told her then that you need more than one of them to make it good but then I would have revealed my secret to everyone. Well the home crowd cheered the boys when they got off their bus and the home town stadium was alive with celebration. We girls sat quietly in the bleachers just waiting. Once in a while one of the boys would make a lewd gesture by licking their lips or something but otherwise paid us little attention. Soon the crowd cleared and the boys went into the locker room to change into street clothes. As I looked at my group of cheerleaders I noticed two missing. They must have chickened out as well. Well that leaves six of us. Two boys each, I thought, we can do it. As the boys filed out of the locker room each went to their cars or their girl friends. Each of us girls ran up to our respective boys to congratulate them. They all seemed to disappear for a while except for Jimmy and I. The stadium lights were turned off and not a sole was in the place except for the two of us and then some of the senior boys started to make their way over to the bleachers were we sat. It looked as though I was left to handle the four or five boys that wanted to follow up on the deal. Jimmy asked if was up to it and I didn't hesitate to say "sure thing!" Jimmy didn't want to disappoint his friends either. He just insisted he go first. We all went behind the bleachers were some of the tackling bags and equipment were stored. The only light came from across the field from the field house. The boys gathered around Jimmy and I. I was still in my cheer outfit. I got down to business and kneeled in front of Jimmy. I took out his now swollen cock and began to give him what I hoped was the best blowjob ever. The other 5 boys just looked on and soon Jimmy was beginning to moan. I knew it wouldn't be long. Jimmy unloaded a huge load in my mouth with a big grunt. That was probably the biggest load he ever came and I had to swallow twice to get it down. The other boys cheered and started to help me out of my uniform. My cunt was dripping with anticipation. I heard a couple of cars from a distance and was hoping that was the other girls were coming back to help me out. Turned out Jill did return with Johnny only to tell me he took care of her itch and wouldn't be staying. She did tell me to take as good of care of Johnny just as I did before. That's how I found out she knew about the first time. She also said the other girls wouldn't be coming back either. I think she planned this as sort of a punishment for me or something. I didn't mind though. At least until I realized the other cars were the rest of the senior boys. That's 12 boys against me. I started to get a little worried The boys had me naked and started kneading my tits and stroking my inner thighs and by now I was so hot there was no turning back. Jimmy started the festivities as though it were an awards night. He said the first one to have me was the leading scorer with two touchdowns and an extra point...his friend Johnny. Johnny proceeded to lay me back and plow is dick straight into me. I can tell you by now I was more than ready. Just like last time, Jill had already fucked him first and now he could last a long time with me. He pounded my pussy for at least ten minutes while the other boys played with my nipples. Just as I was to cum for the first time Jimmy announced that for the best defensive play of the game Kareem gets the second blowjob of the evening and with that his dick was in my face in a flash. Kareem was a junior? This was to be for Seniors only. That's when I realized that standing around me was an additional 6 underclass boys to make a total of 18 here right now. His ebony tool was about the same size as my Jimmy's but turned up a little more. I gulped it down quickly while Johnny finally got me my climax. I sucked so enthusiastically that Kareem only lasted about a minute. He gave me a huge load. The most cum I've ever had to swallow and Jimmy just gave me my second biggest load minutes earlier. I couldn't even swallow fast enough as cum just kept oozing and oozing from his dick. His come tasted sweet and wonderful. Better than any other and I actually thanked him. Johnny came in my cunt finally and that's when I realized he didn't wear a condom (again). I told Jimmy he came in me and he said don't worry, it isn't like he can knock you up, I already did that. That was his official announcement to his buddies about the baby(s). It was also his way of letting the boys know they could save their condoms for their own girlfriends. Jimmy then proceeded to line another boy up by saying "the best special team play goes to Ken". Ken was the kicker and a sophomore. He jumped between my knees with dick in hand. He had a little dick about 5 inches long and with the first load already in me I barely knew he was in me. He too came very quickly but pulled out and aimed his dick up over my stomach. His orgasm was impressive in that he sprayed three long threads, the first landed on my stomach and splashed the undersides of my boobs. The second and third sprayed all the way up to my chin and my hair. If I wasn't already knocked up I'm sure that would have done the job with as much force that had. For a young short dicked kid he'll make some girl a good lay. Johnny then announced one special recognition after another as a boy either arrived between my knees or at my head with a dick. They were of all sizes and shapes. Curved left, right, up, and some fatter than others. Some came in me while others pulled out. All the boys I blew came in my mouth. After I took care of about 6 of them I was ready for a position change. I got up on my hands and knees. The next boy laid back on one of the practice pads that was laying on the ground and that was my queue to start sucking him off. Just then I felt the familiar massive cock of lineman Billy and that wonderful 10-inch dick of his. Good thing I was all lubed up from all the other boys because Billy didn't take it slow with me at all. He mounted me from behind the way he saw all the bulls do to the cows down on the farm he was from never letting up at all. I didn't have to do any work at all with the cock in my mouth because each time Billy would plunge forward so would my head. The cock in my mouth started to explode but because of the motion of my body it pulled out of my mouth before finishing spraying all over my face and hair. It felt warm and I loved it. The practice bag was then placed under my belly now to help hold me up and Billy finally finished and filled my cunt to the brim. When he withdrew big globs of cum ran down the insides of my thighs. The next boy tried to stick his dick in my ass and I protested. I was saving my anal cherry for my Jimmy. He grumbled but stuck his cock in my very sloppy pussy. He pulled out and came all over my ass and lower back and it ran down between my crack and dripped to the ground. Jimmy was hard again and although all the boys had not had their turn at me yet I thought he should have another turn. I had a wonderful Idea. I took the other lineman, Bobby, who had a great 8 inch cock and laid him on the ground. I straddled his huge body with a big split and settled down on his big hard dick. Then I invited Jimmy to come behind us and go ahead take my last cherry hole. With all the cum that ran down between my ass cheeks in the last half hour it was well lubed. As Bobby began bucking up against me from below Jimmy pushed his dick against my ass and it slid in. At first I was amazed at the incredible pressure that I felt although it did not hurt as I thought it would. I was really full of dick though with both holes filled and soon another boy waiting in line came to my head and filled my last remaining empty hole. At one point in this position I actually had a dick in each hand as well as each hole filled and thought for sure it could not get any better. I was wrong. I had the biggest orgasm ever from this position and both boys came in me at the same time while I was cumming. The boys in each hand came against my ribs and there was cum everywhere. Everyone cheered at that one. Now all 18 boys had their turn at me in one form or another. The numbers soon began to decline as only 8 boys remained. They all wanted seconds. Jimmy protested but then said if I was up to it they could all go again. An hour and a half had past since it began. I was sticky with cum from head to toe. I turned back over to my back and just said go ahead boys, I've already gone this far and you guys deserve it for what you did for my Jimmy and me. They brought some towels to wipe some off the runny stuff that didn't dry on me. Apparently I was too sloppy for some of them. They all did take a dip in my swollen pussy though and in turn deposited their own loads. I didn't take another boy in my mouth because my jaw was getting sore. As I had my last of what turned out to be 12 orgasms total for the night I burped a nasty cum burp and tasted again all the many loads I swallowed. The remaining boys said how nasty that sounded. Finally the last of them had enough and went home. The college scouts in the stands that night signed Jimmy to a great college scholarship and threw in a package for me as well. Jimmy is convinced the boys would not have played so hard if it wasn't for their reward. That is why he gives me so much credit for our good fortune. Now maybe after he has 4 good years at college I can convince his new team mates to win a big bowl game to give my Jimmy a shot at the big money in the Pros. That will be another story for another time.