When I was 14 I was pretty nerdy (OK very nerdy). Acne, goofy glasses, not too many friends, etc. I was (and am) very smart and horny, always. I started masturbating when I was twelve and a half years old and have been addicted ever since. I didn't see my first dirty magazine until I was 16 (found it, mostly in tatters, on the side of the road by my house) and spent many an afternoon home alone during the summer fantasizing about different girls I knew, friends moms, girls I saw at the pool, girls in school, my Aunt, you name it. I loved to jerk off looking at my moms underwear catalogs, and on more than one occasion even jerked off with a pair of her panties (sick, I know, but I pretended they were a friends moms).
I had an aunt and uncle who lived in town, and they had a daughter named Linda who was nine. For some reason she didn't think I was nerdy and we were pretty close and spent a lot of time together. As I got older my parents decided I was responsible enough to babysit her while they went out on 'couples night' (my mom/dad and aunt/uncle) - usually dinner and movies. I didn't mind because they paid me four dollars an hour and I was usually home not doing much anyway. The only thing it did was put a crimp in my masturbation routine, but I could manage.
One Friday night my aunt/uncle came over and left Linda, and since they planned on being out late Linda was going to actually sleep over. So I was responsible for actually making sure she bathed, got in her pajamas, etc. For some reason this night I was super horny (probably because I had been at the town pool that afternoon and saw tons of gorgeous girls in their bathing suits) and the perverted idea popped into my mind that maybe I would be able to see Linda naked while she was bathing or changing. It quickly turned from a brief perverted thought to an obsession, and I quickly mapped out a plan in my mind.
After we ate dinner I told her she had to go in and take a bath. She didn't give me any problem and I followed her in the bathroom. I sat on the edge of the tub, turned on the faucet, and as casually and calmly as I could told her to start getting undressed. I expected her to protest, but she didn't. She slipped her t shirt over her head like it was the most natural thing in the world, revealing a pink vest-type bra with a purple bow in the front. She then proceeded to unsnap her jeans, slide them down and kick them off. I didn't stare, I just pretended to adjust the water temperature. I DID look at her out of the corner of my eye and saw her panties were white with little bears on them, and blue flowers, and they were tight. Linda had not developed yet at all, but her hips did have a slightly womanly flair to them and her ass was deliciously small and round. I had a full fledged erection in a matter of seconds.
She stopped there, and didn't make a move to take off her bra or underpants and I didn't press her. I did engage her in some chit-chat (about water temperature, bath v. shower, etc.) which allowed me to drink in her nubile little body. Glancing at the front of her panties I could clearly see a cleft between her legs, and longed to be able to see her naked. Finally the tub was full and I excused myself, and told her if she needed anything to call me. I made a hasty exit of the bathroom, half humped over in an attempt to hide my hard-on pressing against my shorts.
I stood in the hallway, listening. I wanted to hear her get in the water. Then I knew she would be naked. The next part of my plan would take a lot of balls, but I was determined to go through with it. I went to my room and stripped down to just my underwear ( white briefs) and nervously went back down the hallway. I took a deep breath and knocked on the door and walked in, not even waiting for her to reply. I glanced at her in the tub and told her I REALLY had to use the bathroom and I hoped she didn't mind. She was making a mild attempt to cover herself (mostly with her hands down between her legs) but I got a great look at most of her naked body! I asked her again if she minded and she said no, but seemed a bit confused. The toilet was almost directly adjacent to the tub, and there was no way to use it without being seen. I turned around, facing the tub, and dropped my underwear, and my erection literally slapped against my stomach (I was nerdy, but can proudly say I had a pretty big penis for my age...). I quickly sat down and pushed my cock between my legs so she couldn't see it and sat there, pretending to take a crap. Linda was giggling and I asked her what was so funny and she said, 'your weiner'. It was going just as I had planned. I asked her what she meant and she said she had never seen an older boy's weiner, just her friends little brothers.
As she was talking I was looking directly into the tub. The tub ledge was too high so I couldn't see her pussy (damn!) but I could see her chest, which featured little bumps for tits and surprisingly big and puffy nipples. I acted nonchalant and told her boys and girls see each other naked all the time and its normal. I took some toilet paper and pretended to wipe my ass, then stood up, again exposing my erection to her. She giggled some more and I told her that if she wanted we could play 'naked games' when she got out of the tub. Her expression changed, and she seemed confused, but then she said OK and that she would be washed up in a minute. I told her to just dry off and come into my room and not to put her pajamas on yet.
I went into my room and realized I was trembling, badly. I paced for a minute to calm down, then laid on my bed, naked. Without warning Linda walked in, nude. She stood there for a second, hands covering her privates, and she was giggling still. She wanted to know what 'naked games' were, and I told her we could just hang around the house naked, or play a board game naked, or even play 'doctor'. She perked up at the idea of doctor and said it sounded fun, so I said OK I get to be the doctor first. I told her to lay on the bed and I would examine her. I was still trembling and my cock was SOOOOO hard, but I played it pretty cool. I pretended to check her heartbeat, and then had her go 'ahhhh' while I looked in her mouth, then I checked her reflexes. I then told her I had to check for lumps in her boobs and she laughed, and I proceeded to feel her up (best I could, not much to feel). She was staring at my cock almost the whole time. I then told her to lay back and I had to check her privates. Her vagina was hairless and very smooth. And the first I had ever seen; I had no idea what to do but I reached down and ran my finger along her slit which caused her to squeal and giggle even more. It felt awesome, and as Linda writhed on the bed her legs spread apart, causing her slit to open, revealing her pink insides just a bit. I moved my fingers around more and more, and noticed that she was wet down there (I had thought I made her pee, but realized months later that girls get wet when they are horny and excited). I continued to poke and probe for a minute, then announced that it was her turn to examine me.
I laid on my back, my erection standing proud and tall. Linda went through the same routine as me, but as she moved around my body it was hard for her to avoid touching my cock (which had a lot of pre-cum leaking out). Finally said she had to examine my privates, and I spread my legs slightly and told her (pretending) that my testicles hurt. I balanced them in my hand as I showed her, and she reached down and began to roll them around in her hand. I told her that it felt better when she did that, and that my penis hurt too and asked her to rub it. She was nervously laughing as she took hold of it, and began to tug it up and down. IT WAS THE BEST FEELING I EVER HAD! I told her to keep doing it because then the stuff would come out and it would feel all better and she wanted to know what I meant and I told her she would see, just keep rubbing it. As she did I reached behind her and began to feel her ass, and that sent me over the edge. My orgasm started with a solid stream of come that landed high up on my chest, and it caught Linda off guard. She pulled away and said, 'oh my god!' but I quickly resumed stroking myself, almost at the speed of light, and my orgasm continued as I sprayed several more ropes of semen up and all over my chest and belly, and a large pool of come formed on my skin between my thumb and forefinger.
I reached over to grab some tissues and began to clean up, and Linda literally had dozens of questions. We spent the better part of the evening talking about penises & vaginas (with our clothes on...), sperm, baby making, etc. I also reminded her repeatedly about it being our secret. Two more times we got together that summer to masturbate each other, and the last time she showed me where her clitoris was and I learned roughly how to flick it with my finger to make her feel really good.
I am 25 now and have only had one girlfriend in my life, and we had sex every night for about a month. She was pretty fat and not very pretty, but she loved sex so it was cool. I have discovered I am bi-sexual and like to jerk off and do oral with other guys, but prefer women if I can find one who will date me.