Where it happened: her house
Well i was 15 at the time. My sister was 16, as was her best friend Tiffany. Tiffany often came over our house, to see my sister. I always tried to be really nice to tiffany so i could get on her good side. I was a sophmore in high school and Tiffany was a junior. I liked high school alot because there were so many fine girls there and all of them were much more mature than those jr. high chicks. Anyway my sister and tiffany were both on the cheerleading squade, Tiffany being the head cheerleader. now when you think head cheerleader, you automatically think that she would be with the captin of the football team. Well, she was at one point but dumped him because i guess from what i heard, he was being an asshole. Everyday since i didn’t have my licence yet, i had to wait for my sister after cheerleading practice so she could give me a ride home, when i couldn’t get one from my friends. After awhile of wtching the cheerleaders i got to know all of them, and not one of them was ugly. This is what led me to popularity, not only with my friends that i had known a long time, but with guys that i didn’t even know. Pretty soon i was one of the most popular guys in school. just to brag a little, at the end of the year i was voted most popular sophmore. Anyway whenever i would see Tiffany around campus she would say hi, or we would start talking. One day, my sister had not gone to school because she was sick, and i decided to go to the cheerleading practice to walk with Tiffany home, since she just lived a couple doors down. After pratice i waited outside the gym for Tiffany to leave the female locker room, just as i always did. All the girls that walked out before Tiffany and my sister(which was the whole cheerleading squade) stopped and talked to me or at least said hi. Like usual Tiffany wailked out last. Her hair was still wet from the shower. But unlike usual she was still wearing her cheerleading clothes. As we were getting ready to leave she relized she had left her backpack in the gym. So we turned around, went into the gym. There it was sitting on the bleechers. I stopped a waited by the gym door for her to get it. I took a long look at her as she walked over to it. There she was still wearing her short skirted, small shirted, cheerleading clothes. Now Tiffany, being a cheerleader, of course had an excellent body and perfect size tits. She didn’t have too much chest, but she didn’t have too little, like i said perfect. When she bent over to pick up her backpack, i began to think of us being together, which i usually did in private if you know what i mean. my dick started to get hard, so i tried to think of something unsexy, like my sister naked. That did the trick, soon i was limp again. She walked back over to me and said we can go now. On the walk home we started takling, but something we never talked about before. We got into a conversation about relationships. She asked me how i broke up with my ex girlfriend Terry. I told that Terry was nice but she was kind of bitchy, and i was board of her. Then i asked her what happened to the football player, and she simply said he was an asshole. Then i said something dumb(well not really, it got us together). I told her that friends like me and her were would make perfect couples. It got real quiet, fast. I was cursing at myself in my head.Then after a few seconds she replied that we would make a good couple. That suprised the hell out of me. She asked me if i wanted to give it a try and of course i said yes. So by the time we got to her house we were being all soft on each other. Her parents worked late and she was an only child so she would be home alone. She invited me in, and i accepted. I had been in her house before, but bot for long. she got us something to drink and we sat on the couch to together and watched T.V., for a sec. The next thing i knew we were all over each other. Since she was wearing a skirt my hand had easy access, to rub her leg all the way to her cheerleading underwear stuff. Thats when things heated up, she was sitting on my lap frenching me, and i was getting a huge hard on. Since she was wearing only a skirt she could feel it. Pretty soon i had my shoes off, along with my shirt and pants. There i was in nothing but boxers with this fine ass cheerleader feeling me up. By this time was shaking, i was so nervous. She was a little nervous too because i could feel her hand shaking. So i hand pulled off this little cheerleader shirt to expose her braw. Now this being my first time, i was an amutre at the removment of the braw. It took me a sec to get it off but i did. There was her perfect breasts. Her young pink nipples were hard. So i laid her on the couch, and began kissing her neck. After i kissed and sucked on her neck long enough to give her a hiki, i move down to her tits were i licked, sucked, a lightly bit her nipples. By this time she was softly moaning. Then my busy lips made their was down her tight firm stomach, then to her skirt. Thats when i placed my hands under her skirt to remove her wet panties. After i had the panties off, i simply flipped up her skirt, and began attacking her soaking pussy with my tounge. I licked hard a deep into her quivering slit. With one free hand i slipped my finger in and out of her asshole. Then with the other hand i began finger banging her. I wasn’t that cordinated yet so i had to stop fucking her in the ass with my finger so i could concentrate fingerbanging her. I did this untill she orgasmed several times, makeing my finger wet with her womanly juices. While i did this i kissed her again, and sucked on her nipples. I had done this for about 20min. Then off my boxers came and she was down on her knees giving me a blow job. She had done this until i cummed in her mouth, were she swallowed my cum. She licked and sucked on my sack sending me into heaven. The thought crossed my mind that i was going to be a part of Tiiffany’s no matter what. I was about to take her virginity. So i softly whispered if she wanted me to fuck her in her pussy, and she said yes. So i pulled the condom i had always kept in my wallet out and slid it on. Then i pulled her by the legs to the edge of the couch were her ass would hang off. Then i put her legs in the air and spread them giving me acesse to her pussy. I aimed my weiner and stuck it not even half way in, and she moaned in a pleasure. Then i just startted going off, taking my dick in and out of her. It took me a couple minutes to orgasm, because i had already orgasmed a few minutes before. But the second i penitratied her pussy she hit orgasm, and continued to until i was done pounding her pussy. As i was pounding her, the little green skirt i didn’t remove flopped about(now i don’t know about you but i think girls that wear skirts, are so sexy, but only if they have the body and looks to wear it like Tiffany did). After i was done there i flipped her over and took her from behind. I fucked her in the ass until i reached my final orgasm. Then i sat down, and we were done. We had been fucking for a good 35 minutes and my parents were probly worried by now. We laid on the couch together me naked her in her skirt, and went to sleep. When we woke up it ws about 6. Her parents woulden’t be home for another hour and a half. So fucked again, and after that i went home to get in trouble. It was only later when i talked to her on the phone that she told me when i entered her pussy the first time it hurt, and i had popped her cherry.