I was a real late bloomer and very shy. I didn't talk about sex stuff with my friends, and all my cousins were girls older than me, so when I started growing hair and getting bigger down there when I was about twelve, I didn't know much about what was going on. I had played with my dick when it got hard but I never did anything that was even close to masturbating. I had not yet had a wet dream but it probably would have occurred before much longer. Instead this story happened and I never had any wet dreams because of what I learned that weekend.
Right after my 13th birthday, my parents took me and my little brother, who was ten, over to my aunt and uncle's house because they had just built a new swimming pool and they wanted to show it off. They had three daughters who were at that time I think 20, 19, and 16. The two older girls were away at college then. I had never played much with them growing up because we were so far apart in ages, but I had always got along pretty good with the youngest one, Lesley. She could be bossy sometimes when we were growing up but most of the time we were on very friendly terms, even if we didn't see each other all that often.
When we got there, we all splashed around in the pool for a couple of hours and then my parents and my aunt and uncle got out and changed to go out to dinner or something. After us kids were left alone for a little while, Lesley started teasing me because I was now a teenager but I didn't have any hair under my armpits yet. I was embarrassed but I didn't say much about anything, I just splashed the hell out of her when she would get close enough. After this went on for maybe half an hour Lesley looked over to see what my brother was doing at the other end of the pool, and then she leaned in close and whispered, 'I bet you don't have any hair on your dick either.' I was so shocked it took me a few seconds to say 'oh yes I do' which was the truth, even if there wasn't very much of it. She said 'yeah, right' and swam over to splash my brother. He got tired of that pretty quickly and he went inside to play computer games. Lesley floated around a while and then said, 'so prove it.' I said 'what?' and she said, 'prove there's hair on your dick.' I didn't know what to say or what to do. Then she said, 'come with me,' and she got out and went inside the house. I got out and followed the wet footprints from the patio into the house, past the den where my brother was playing a game, and up the stairs to the second floor.
Lesley was waiting in the hall next to the door to her bathroom, still in her wet bikini. She pointed at me and then pointed to the door, and I nervously stepped past her into the bathroom. She followed me in and closed the door. She put the lid of the toilet down and sat on it. She said, 'so let's see your hair.' I was blushing furiously and was starting to get, I don't know if it was scared or what it was. I had never felt that feeling before (now I know it was being horny!). I said I didn't want to, and Lesley stood up and put her hands on my shoulders and said, 'Eph you know I like you, and I really think you have a nice body. I would never make fun of your dick, you don't have to worry about that.'
I decided what the hell, and I said OK. Lesley sat back down and watched as I untied the strings on my swimsuit and peeled it down my legs until it dropped onto my feet. It was the first time since I was out of diapers that I was naked in front of anyone besides my little brother or our doctor, and it definitely was the first time I was naked with an erect penis in front of a girl. Lesley said, 'whoa, it IS hairy, and it's big too.' (well maybe for a 13-year-old, it was about six inches then and has only grown a little bit since)
I had a brainstorm and asked Lesley, 'Can I see you?' She said OK and she pulled off both halves of her bikini. She leaned back and opened up her legs a little and I just about had a heart attack seeing my first naked girl. My dick was flopping up and down with my heartbeat and Lesley put her hand underneath it so that when it flopped down, it just touched her palm. She stared at my dick and asked me, 'can you cum?' I didn't know what she meant because I had never jerked off, so I just mumbled, 'I don't know.' I could hardly breathe but squeaked out, 'can I touch you too?' Lesley took my hand and put it on her breasts. Her nipples were hard and pointy, and so were mine. Feeling her made muscles I didn't know I had inside behind my dick throb and jerk. Lesley said, 'OK, you just hold still and I'm going to see if you can cum.' I still didn't know what she meant but anything she wanted to do was just fine with me, just as long as we could stay naked together.
Lesley opened a drawer and took out a bottle of hand lotion. She dumped a big glob into her hand and then she GRABBED MY DICK and rubbed it up and down, spreading the lotion all over my dick, over my balls, and down into my butt crack. It was freezing cold and I was going crazy because it felt so fantastic. I started to lose my balance a little, and she said to lean toward her and hold onto her shoulders. This angle put my dick right in front of her face.
She was rubbing my dick faster and squeezing it harder now, and I was breathing faster and deeper. My legs were shaking and I kept feeling muscles contract in my crotch and butt as she stroked my penis with one hand and massaged my butt with the other. Then suddenly I noticed Lesley was actually touching my butthole and a moment later she pushed a finger inside me. She said, 'does that feel good?' and before I could answer the question, I came. As Lesley stroked my dick to my first orgasm, I shot three or four streams of semen onto her breasts and stomach, and my butthole clamped down onto her finger again and again. It was absolutely fantastic, and I slumped against Lesley, totally out of it now, and she gently held me and said, 'well, now we know you can cum!'
After a few minutes I had got my breath back and was starting to get hard again. I wanted to do it again or check out Lesley's body or SOMETHING, but we were interrupted by our parents returning home. She threw my swimsuit at me and said, 'go play with your brother' as she dashed naked down the hall to her room. I wiped the cum off my dick and my stomach, put my swimsuit back on, and went back to the pool, where I tried to act normal in front of the adults. Lesley didn't rejoin the party that day, instead she went out with some of her friends and we went home before she came back. That night, before I went to bed I locked myself in our bathroom, took off all my clothes, and masturbated for the first time. I came thinking of Lesley with one hand wrapped around my dick and a finger inside me. Almost every time I have masturbated since then, that image of Lesley is what makes me cum.
I wish there were more stories to tell about Lesley and me, but there aren't. Our families drifted apart due to divorces and moving around, and I rarely see her anymore. She has been married and divorced twice, and has a couple of kids.