Andrew's Adventures

It was one week before Halloween, and I was at my friend Dave's house discussing the Halloween party he was throwing. My name is Andrew, and Dave and I were 14 and freshmen in high school. Dave lived at home with an older sister, older brother and his Father. His Mother had left his dad a few years back. Dave and I became friends 4 years ago, when his dad started working with my dad, and they would hang out after work. Dave was your typical jock, 5'9", with slightly curly black hair, and good definition, which he got from his weight lifting for football. I on the other hand was your average freshman in high school, maybe a little on the short side at only 5'4" with hazel eyes and short blonde hair, and a slight tan. I was fit, but not muscular, and my greatest attributes, from what my girl friends had said, not that I had many girl friends, were my cheeks, the rosy one's on my face and the two in my pants.

We were in his kitchen discussing our costumes for the party, when Dave said he was going as football player, and I thought to my self how un-original. I couldn't think of what I wanted to go as, and I asked Dave what he thought. His sister walked in and heard the conversation, and in laughter said, "You should go as his cheerleader girlfriend". I cringed at the thought, and said "hell no", but Dave thought it would be hilarious. His sister Rebecca was a couple years older then us, and on our high school cheerleading team. She started talking about how she could fix me up with the whole outfit, as we were about the same size.

Saying no to Dave was hard, but I was determined to come up with another idea. "Come on", he said, "we'll be the hit of the party you have to do it". But I tried to hold my ground against the two of them. "Look we'll draw straws for it, looser has to go as the cheerleader, while the other one goes as the football player", he said. I knew this was my only chance to get out of this, even though I could never fit into Dave's football uniform, and he knew it. Long story short, I of course pulled the short straw, and the only one who seemed pissed or shocked was me. Dave and Rebecca quickly decided right then and there that I would come over a few ours before the party and Rebecca would fix me up.

As the party drew closer, my nerves were getting the better of me. I even tried to talk Dave out of it, but he wasn't having it. He said he had told a couple people already about our costumes and they were all dying to see what I looked like. He then told me that his Father, Mr. Roberts, had a last minute change of plans and was going to be out of town. "Your dad will kill you if you still have the party", I said. "He already worked it out", was Dave's response, "Steven is back this weekend, and he and my Dad worked out a deal, and Steven's going to supervise the party". Now I should tell you, I was like a lot of 14 year old adolescent boys, not that I knew it at the time, but pumped with so much testosterone, that everything and anything looked good enough to hump, and Dave's brother Steve was no exception. Although struggling with the concepts of being straight, gay, or bisexual, and which term fit me, Steve had been my fantasy as of late during my evening jerk sessions. Steve was Dave's older brother by five years, and was in and out of the house as he was in college at the local State school. He was 6' of ripped solid muscle, and in my eyes a Greek God. "Drew, Drew, earth to Drew", I heard as Dave landed a punch to my arm, "dude, I lost you there for a second", Dave said as he continued with the conversation, as if my participation in it really didn't matter, which it didn't. "So with Steve at the party, we'll be able to sneak more beer, and hopefully get the girls feeling pretty good". Dave kept talking about the party all through lunch, but all I could think of was that his older brother was going to be there, so much so I forgot about my impending date with a cheerleader costume.

Finally the day of the party arrived and I headed to Dave's house as planned a couple hours early to meet Rebecca. Now, only recently had Steve become my jerk off fantasy, in the past it was Rebecca, as she was HOT! She was your typical high school cheerleader, quite popular and very good looking. She had dark hair that hung to middle of her back, with great tan skin and some of the best tits in our whole high school, and here she was waiting for me at the door, apparently excited to get started. As we walked to her room I couldn't help but stare at the pink sweat bottoms she was wearing with the word sexy across her ass. If it wasn't for the cheerleader outfit on her bed in front of me I definitely would have been harder than an oak tree.

She pulled me over to the bed and presented me her cheer outfit, which was a tight fitting green and white top with our school name on it and a short green skirt. Now these items I had expected before I arrived, I mean what high school boy doesn't know what his schools cheerleader outfit looks like? It was the lacey white bra and what looked like really small white Speedos that shocked the hell out of me. I started to back pedal and stammered, "I don't think I can do this". "You have to wear the bra, it's the whole idea of the costume, you know to look like a girl". She said in the typical teenage girl fashion, annoyed with one hand on her hip, looking as if I was the worlds biggest idiot. "I need something to hold the socks I'm using for your fake breasts", she said. Unfortunately her reasoning on the bra made sense, but I saw no reason to wear the Speedos, which she quickly corrected me, by calling them cheer briefs. "It would look stupid to wear boy underwear under the skirt, especially boxers, as when you move quickly you can see under the skirt". "Fine", I sighed, knowing I wasn't winning this battle.

So here I am in a cheerleading outfit complete with a white lacey bra, stuffed to look like tits, white cheer briefs, that look like thin white Speedos, and no underwear on underneath, as I was wearing boxers when I arrived. Rebecca came in after I was done changing, and with a giggle said "You look as cute as a button", which killed any shred of manhood I had left. She then finished the costume with white ruffled socks, white shoes, a Blonde wig they bought just for me, and bright red lipstick. Me being a late bloomer I only had a light covering of blonde peach fuzz on my arms and legs and my soft facial features, I honestly looked like a freshman cheerleader, but with exaggerated tits and dramatic red lipstick. Dave came in and thought it was perfect, "Damn your bubble butt is looking fine in that short skirt" he joked, as he put his arm around me. I think I actually blushed.

As we were walking out of Rebecca's room I saw Steve for the first time, he was wearing a tight white T-shirt and a pair of jeans and had a beer in his hand, walking down the hall. "Hi Steve", I said trying to act calm and cool and failing miserably as my voice kind of cracked. "Looking good Drew" he said as we passed, and then slapped my ass. But it wasn't your normal slap, like after a good game in the locker room, but more of a lingering slap, where his hand stayed on my butt after it hit for a few uncomfortable seconds, as he grabbed a fill. I looked back at him with an uneasy smile, "Thanks".

As Dave predicted we were a big hit and people loved the cheerleader costume. However where Dave was a big hit with the girls at the party, none of them were looking or talking to me, and I was still a little uncomfortable with the costume, as I was getting pinched and grabbed by a few of the guys at the party, and not the cute ones, all night long. At one point a found myself sitting on the couch just to avoid the unwanted contact. Now I was still confused about all the feelings I was having towards guys, but the one thing I wasn't confused about, was how my small town high school felt about gays, and I sure as hell wasn't giving anyone a reason to think I was.

As I was sitting there I notice from across the room Steve was sitting in a recliner drinking a beer, and clearly starring at me. When I followed his gaze I realized I was sitting with my legs open, and he could see the cheer briefs and what little they hid. Before I could even think to reposition myself on the couch Steve got up and headed towards me. As he sat down next to me, so close that our legs were touching, he asked how the party was going. "Its fine, but I might leave", I told him. He said it was obvious I wasn't having a good time and asked why? "I'm just not comfortable in this costume and all the joking", I said. "Don't leave, little buddy," he said. He then looked around as if to make sure we were alone, "I might just have a way to help you out, why don't you follow me". He took me to the back washroom where he grabbed a bottle of Jack Daniels from a cupboard and poured us a shot each. "You'll have to drink it quick; I can't have the other kids seeing this". So I quickly downed it, followed by another. This went on for a few more hours, where every 15 minutes or so Steve would call me over and we would have a shot. This wasn't the first time I had ever had hard liquor, but this was the first time I had ever had so much so fast. My liquid courage was at an all time high, and I was having more fun at the party now. Kids were talking to me and I wasn't so bothered by guys trying to grope my fake tits, or even grabbing my ass. I even sat in one guys lap for a photo.

As the party started to end, you could see people leaving, and as usual Dave had a girl all over him, and if my guess was right I wouldn't see him until tomorrow morning, as it was my plan to stay the night as I always did. Steve caught my eye again, and signaled for me to come over, and I followed him again to the back washroom. He opened the cupboard ," looks like we're out of Jack sport", he said, as he put his hand on my shoulder, "I'm glad you decided to stay, looks like your having more fun". I was feeling really good, drunk really, and told him, "I'm having a great time, and that has a lot to do with you". When I said it, I meant he had a lot to do with how I was feeling because of the shots he had gotten me, but I think he took it to mean, he was the reason I was having a good time, because all of a sudden he tells me, "I'm having a good time too, and its because of you". Then he grabs the back of my head with his other hand and pulls me into a kiss. His lips were warm and inviting, and even as drunk as I was, I still remember him lightly biting my lower lip as we kissed. Reality crept back in and I was scarred someone might see us, but I gave in a let him continue to kiss me, as his tongue entered my mouth. I finally pulled away, and he looked at me and said, "Do you want to follow me up stairs; I have something that will make you feel good?" Now it was my turn to misunderstand what he said, as I thought he was talking about more liquor, and still in a daze from the kiss I said sure, and followed him to his room, as I would have followed him anywhere.

When we got there he opened the door and let me go in first, and then shut the door behind us. He walked up to me and again he put his hands on me, this time on my hips, as he leaned in for another kiss. But this time his warm wet lips were on my ear, sending shock waves through me, as his tongue and warm breath danced around my ear, making me week in the knees. I tried to regain my ground, and mumbled to Steve, "Should we be doing this". When his kiss traveled to my neck I heard myself let out a soft moan, it felt so good, that I almost missed that his hands had traveled down my hips to my bare legs, where they rested for only a second as they started back up my thighs under the cheerleader skirt and stopped on my ass. Now cheer briefs are somewhere between Speedos and girls panties. Not as thick as Speedos, but not as thin as panties, as they were meant to be worn over panties. But when his hands started massaging my ass, it felt like I was wearing nothing. I new I should stop this, as this was going to far too fast and I was starting to get hard, as my cock was making the already tight briefs unbearable. "Please Steve, ...huh huh, sto, stop,... I I can't do this I'm not gay". He just ignored my requests and lifted me up and set me on the bed. "Its ok sweetie, I'm not gay either, but you have been driving me crazy all night long with that ass of yours". He slid his hands down my legs to the back of my calves and then to my feet and removed my shoes. "Please Steve", was all I got out as I sat there my head spinning from the booze, my thoughts, I mean here I was in a cheerleader costume, and the guy I have been fantasizing about at my feet.

I had to sigh, as his big hands started massaging my feet. "You smell so good", he said as his mouth started sucking on one of my big toes. "God, your legs look so smooth", as he had abandoned my feet and moved to the inside of my leg, where he began kissing up my calf to just below my knee. My 5" hard cock was throbbing in the worst way. I could actually time its pulsing by the heavy beating in my chest. Steve had moved to my other leg and was slowly working up inside of my thigh. "Ahh, Oh God, pleeaasssse" was this really happening. I knew where he was heading, and at this point my legs were over his shoulders and I could no longer see his head past the skirt. My hands grabbed the sheets tight, as I was moaning, "ohh no, no, ummmm, OH FUCK!" His mouth had reached my nut sack, sucking and licking them so slowly I could feel his tongue stutter as he scraped across my balls. "Oh yeah, my little girl tastes good", was all I heard from under the skirt. But the mere fact that I heard it at all, over my moaning was amazing. The thought of Dave coming in to see what all the noise was from, and seeing me, still in the cheerleader costume and wig, with my legs over his bothers shoulders moaning like a whore, crossed my mind for a millisecond as Steve started mouthing my cock. "Shit, Shit, Shit", I thought I was going to cum any second, when all of a sudden Steve stopped and popped his head out from under the skirt. "How's my little girl doing? I bet you're having a good time now".

I caught my breath and sat back up on my elbows, when I noticed Steve was taking off his shirt. I started to get up and move off the bed, with the intent just to get out of the costume, when Steve said through a big grin, "Whoa where do you think your going? You can't tease me all night long and then just leave". With Steve's shirt off I could see he had a nice patch of chest hair, and his muscles rippled with each of his movements, which were quick to say the least, as he stepped in front of me. "Look you don't have to worry, I know you want this, your boy pussy is dripping wet". "I'm not going to hurt you Drew, and if you trust me we're going to have a lot of fun tonight", and with that he put his hand on my shoulder and gently pushed me to my knees in front of him. "What if Dave comes in?" was all I could think to whimper". "I locked the door and he's got his own pussy to fuck tonight, so I am sure he won't be bothering us". I was looking at the floor, trying to figure out my emotions, should I bolt, should I tell him about my fantasies, did he just refer to me as his pussy to fuck?

Steve put a finger under my chin, pulled my head up, and looked me in my eyes, and simply said, "Take my pants off cutie". He sounded so sure of himself, that I started unbuttoning his jeans before I even knew what I was doing. When they dropped to the floor, my face was inches from the biggest cock I had ever seen. Stuffed into a pair of tight white briefs and poking out the top, had to be at least 8"s of thick hard cock. Steve had stepped out of his pants and now was only wearing his underwear. "Ok babe, pull my underwear down". I was frozen in that room kneeling in front of my best friend's brother, the wig on my head causing me to sweat, my cock throbbing, my head spinning, unable to think, to move. I was snapped out of it quickly when I felt Steve's cock head drag across my lipstick covered lips, leaving a trail of pre-cum. He had tucked his underwear under his balls, and with one hand around his snake, the other grabbed the wig. "Oh yeah, yeah, come on sweetie, open up for daddy". I heard his words and gulped as I realized he wanted me to suck his cock. I gave up on trying rationalize the situation any more, as my dick decided for me, I was going to enjoy the moment; So I opened my mouth and his cock slid in.

As his cock entered my mouth, it was battling with my tongue, as I started giving my first ever blow job, he grabbed both sides of my head and effectively held me still. "Oh God your such a little whore, yeah suck that cock,... Ummm, fuck your good", he kept repeating, as he tried to shove more and more of his cock into my virgin mouth. Never having done anything before sexually, except jerk my own pud, I was sure I was doing a bad job, but trying as best I could. At one point his cock made it all the way to the back of my throat only to be pulled out suddenly with me coughing, eyes watering, looking up at him like a lost puppy hoping for him to say I was doing great. "I knew cheerleaders like to suck cock, but damn you have to be the best cocksucker I've ever had", He said as he walked away from me to near by dresser. I smiled from ear to ear when he said that, wiping the excessive spit coming from my mouth.

I was still kneeling when he came back with a tube of what looked like lube in his hand and completely naked, big hard cock swaying in the air. Steve picked me up and kissed me before turning me to the bed. I was hoping I could finish the blow job, as there was part of me that wanted to taste a mouth full of cum, but Steve clearly had other ideas, as he bent me over the edge of the bed, and with his left arm sliding up my back under my top, his right hand was rubbing my ass. "Steve I've never done this before". "Ohhhh, Uhmmm, shiiit", was all I could say as his hand moved from my ass to the front of the cheer briefs, where it slipped under the elastic band and over my cock. His mouth had moved to my lower back, with his lips slowly dragging up my spine. "Shhh", was all he said as his hand wrapped around my cock and started stroking me. "Oh, Oh,...Ahhh", I found myself moving my hips to his strokes, pushing my butt into his groin, his cock slipping under my balls and adding a new level of pleasure. His other arm had slid up my back and was resting under the bra straps. "God I wish you had real tits", he said as he whispered in my ear and pushed his weight into my ass. As if he remembered what I had said earlier, "Don't worry babe, you're not my first virgin cheerleader, now just relax", as he kissed my back again and his hand stopped stroking my cock, and slowly pulled the cheer briefs down, which must have been soaked with pre-cum.

I was dripping with sweat from the wig and my nerves. I had to take the wig off or I was going to over heat. "Go ahead babe and get comfortable, your hot with or without the wig, you can be my little sporty slut". Steve's constant referral to me being his little girl, or babe, was having it effects, and I would get a horny warm feeling rushing through me to my cock every time he did. As I laid my head on the bed, I looked over and saw in the mirror of the dresser me bent over the bed, with my short hair matted down, the cheerleader top pushed up to my shoulders, my back glistening with sweat, my lower back covered by the flipped up skirt, and my naked bubble ass just inches from Steve's throbbing cock. You couldn't see my cock as it was rock hard and pinned between me and the mattress. It looked like Steve was about to plow some hot little cheerleader, and he was.

Steve's lubed hand slid over my cock and balls a couple times getting them nice and wet, and then his fingers started tracing between my cheeks. When he brushed over my boy hole, I moaned from the new sensation. "Aahhh, man, shit, ...oohh, yeah, Steve". "That's it baby tell daddy what you like", Steve said as his fingers centered on my hole, lubing the outside pretty good. As I felt one finger starting to push in, I clenched and tried to climb up the bed, "Oh God, please" I whimpered". "Just relax he said", as I felt his finger plunge into me. "Aahh, huh, huh, mmmm", his finger worked back and forth opening me up. "You sure are tight, for a cheerleader", he said with a little snicker. I felt him try and add a second finger. "Oh crap", I grabbed the sheets harder, as the second finger pushed in, and started sliding together with the first. Every time he pushed in with his fingers, my body pushed up on the bed, humping my cock into the sheets and mattress, "Uhh, rrrrgh, Uhh," I needed to cum so bad. I looked into the mirror again and saw Steve using his other hand to stroke his huge cock, and my God it looked bigger than before. He pulled his fingers from my ass and added more lube and shoved them in, driving me hard into the mattress, "Oh God!" came my muffled scream into the mattress. "Damn your boy pussy is real tight". He worked my ass over for quite some time, with just the two fingers, to the point, it started feeling good, until he added a third finger, causing me to bite my lower lip, as he stretched me good. "Ok baby, I think your ready, I sure the fuck am", he said. There was only a short second between his fingers coming out and his large mushroom head pressing up against my hole. I was breathing like a pregnant woman in labor, as he leaned in and whispered in my ear, "Here we go sugar, relax and push out like your taking a dump". And with that I felt him bare his weight down and drive the tip of his dick into my boy pussy. "FUCK, I cried out as it went in, "Take it out, huh, huh, take it out, oh God it hurts", were unfortunately the first words to escape my mouth, as even though it did really hurt, I wanted this bad.

Steve held still, I think he too was feeling the grip of my ass, "babe I don't want to hurt you, I'll stop if you want me to". My breathing had slowed down a little, but the pain was still there, "No, noo, don't stop, uhh, just go real slow", I said through clenched teeth. "Hold on sweetie the hard part will be over soon", as he kissed my neck and with that he rocked back a little pulling his cock back what felt like a mile, but was probably only centimeters, and then rocked forward slowly pushing his cock just a little deeper. He repeated the movement for a while until I could tell he was getting closer to being all the way in.

"I'm, sorry baby, your tighter than I thought you would be. On his final thrust Steve nipped my neck with his teeth as he drove his cock in all the way, "Ohhh fuccckkk", I gasped.

Steve laid there with his full weight on me, hard cock buried to the hilt in my ass, not moving, and whispered, "I know it hurts baby, but give it a few seconds and it will feel really good". It did hurt, but you know what's funny about that moment, I can remember it hurting, but I can't describe it to you today, I just know it hurt. What I do remember, and what I can describe is the feeling of his bush and balls resting on my ass. The tickle of all his coarse curly hairs on my smooth butt, the weight of his ball sack lying on the bottom of my cheeks, and its heat.

I had my eyes closed as Steve started little jabs with his cock. "Ahh, ugh, huh, mmmm, OHHH!" Steve had hit something with his thrusts and my moans let him know when he did. "There its lover, I found your little boy button," as Steve started directing his thrusts at that spot. The pain was getting replaced with intense pleasure, "Oh GOD, Ohh, yeah, fuck yes, ohh shiiit yes." Steve didn't miss a beat, "Looks like my little cheerleader is starting to like her pounding." His thrust were more drawn out and deliberate, pulling at least half way out and pushing back in with the intention of driving me crazy.

This was it, I was no longer a virgin, I was getting fucked, and I loved it. "Does My little cheerleader need it harder?" Steve asked as he drew his cock almost all the way out and thrust back in with authority, "Fuuuuuck" was all I could get out as my teeth clenched the sheets. I was on sensory overload, Steve's thrusting was driving my hard cock into the mattress, and I new I was close to cumming. "I need to hear it sweet hart" Steve said, "Come on tell daddy what you want." Ohhh, ..Fuck me, ..PLEASE!! God, Don't Stop." I couldn't believe what I was saying, but it felt so good. Steve slowed down, and as he withdrew his dick, "Not yet baby". Steve said as he grabbed me by the hip and flipped me over forcefully, then sat me up and took my top and bra off, and then yanked the skirt off, all in a matter of seconds. Holding the skirt, he said "Don't want to get my sisters uniform too dirty do we," and with that he threw it on the floor and grabbed my legs and dragged me down the bed until my calves were on his shoulders again and his cock was at my boy pussy. "Yeessss!" was my cry of ecstasy as he drove his cock back in.

Looking in the mirror again, what once was a teenage boy in a cheerleader costume was now a naked boy getting his ass plowed, and loving it. The only remnants of the costume were the ruffled white socks and the smeared lipstick. Steve held my right thigh with his left hand as his right hand stroked my cock and balls. "I knew you would be a great fuck the moment I saw you." Steve's right hand was stroking my cock like mad and I knew I wasn't going to last much longer. "Please, please, please, fuck me, OH SHIIIT!" And with that my body arched and the first blast of cum came firing out of my cock and hit my forehead and face, the second shot hit my mouth and chin, while my boy hole squeezed down hard on Steve's cock, and the rest of my shots hit my stomach in the best cum of my life.

Steve's pace picked up as he did one final thrust with all his might as he exploded into me. "FUCK, fuck, fuck, I'm cumming", he yelled.

I was a horrible mess with cum in my hair, eyes, and mouth. I could taste the salty cum as Steve laid down on top of me. I had to wipe the cum from my eye lids before I could open them again. When I did, Steve was looking up at me with a huge smile, "Now that's what a cheerleader should look like". For the second time that night I blushed. I felt Steve's dick start to shrink and eventually pop out, followed by his cum running out of my ass. Exhausted, smiling like a little boy who just lived out his fantasy, but scarred as to what it meant, my face must have been an expression of mixed emotions. Steve came back from getting us a towel, and as if reading my face said, "Don't worry babe, no one will know, and you don't have to wear a costume the next time". Again his confidence was alluring and reassuring, as I smiled back at him, "Next time"? "Yeah, next time".

"But you would look good in a maid's costume", Steve said as he climbed into bed with me. I fell asleep with Steve's limp cock pushed between my ass cheeks, his arm holding my chest, and images of me in a maid's outfit getting plowed over the arm of couch.

If you liked this story, please send comments to tfreitas91@yahoo.com. Please be kind as this was my first attempt at writing.