This is a true story with only the names changed. It is the story of how a high school senior helped educate his freshman neighbor about sex.
If this is something that offends you, please read something else.
This takes place many years ago, when I was 17 and starting my senior year in high school. Devin was 14 and starting his freshman year of high school. We lived next to each other, but weren’t really close friends because of the age difference. That would change, and we are still close friends to this day.
Devin was playing midget football that year, and had a game in the next town on Saturday. His mother asked me if I could take him, since she had the chance to work overtime. She would buy us pizza after the game. I said sure, I can do that.
Saturday came and I went over to get Devin, but he wasn’t dressed for the game yet when I went over so I told him he better get moving or we would be late. He got his stuff and took it into the bathroom to change. (He was shy to undress in front of me). From the bathroom, he asked me if I can go in his top dresser drawer and get his jockstrap and cup and hand it in to him, since he forgot to take it in, and can’t play without it. I opened the drawer, and saw his tighty whiteys, and there was one jockstrap in there, with the small youth cup. (I played sports myself, and I had outgrown that size when I was 11 or 12). I thought he must have another one somewhere else and looked in another drawer, but didn’t find any. He asked what was taking so long. I said "Devin, I can’t find it, all that is in the top drawer is your old little boy nut cup, where else would it be ?"
At that point, he stormed out of the bathroom, naked, and red in the face, grabbed the tiny jockstrap and cup, and said “My dick hasn’t grown yet and I still wear this size, ok ?”
I said “oh, I’m sorry, i didn't know.... “
He went back in the bathroom and got dressed and then we left for the game. He wasn’t talking on the way there. I told him I was really sorry about what I said, and didn’t mean to insult him. I told him when I was his age I wore a bigger cup, and just assumed he would too, but we are all different and grow at different rates.
He said “yeah i know i am small down there. It’s not your fault. I get teased in the showers after PE because I have the smallest dick, and barely have any pubes”
I told him not to worry, he would grow, he was just late starting, and that size didn’t matter much anyhow, except for showing off in the locker room.
So after the game, we got in the car. I asked him whether he wanted to go out for pizza or have it delivered. He said to get it delivered, since he was all sweaty and smelly and wanted to get a shower. I was glad he chose to eat at home, because he really was smelly, and I sure didn’t want to take him to a restaurant that way.
We got back to his house, I ordered the pizza, and he asked if i could help him get his pads off. I said sure, and we went to his room. He had gotten over his shyness, because he pulled his football pants off, and was just in his jock and cup, which he proceeded to take off, leaving him with his tiny dick sticking straight up. He asked if I would take his uniform down to the laundry room. I said “oh sure, give me the job of carrying your nasty smelly jockstrap”. He said “never mind then”. I told him “I was only teasing, my jock gets pretty smelly too, it’s not a big deal. Now go have fun in the shower”
The pizza got there, and he came downstairs about 10 minutes later, in athletic shorts and a t-shirt. It was obvious he had a boner tenting out his shorts and he was trying to adjust it so it didn’t show.
I joked and said “wow that thing never stops - how many times a day do u whack it?”
He said “what do u mean? hit it ? i don’t do that it would hurt! “
I said “no, you know”... and i made the universal hand motion jackin off symbol
He had a blank look and said “whats that?“
I said “you know - jackin off “….. then i realized he probably was embarrassed to admit he did it and I said “sorry if u don't wanna talk about it”
Devin said “no, i wanna know what it is, i hear boys talk about that but i don't understand what they mean”
I said “really? you don't..... rub your dick and make it squirt?”
Devin got totally red in the face and hung his head, and said “no, i don't know how.” Can you teach me how to do it?"
He had pubes, so i figured he was able to shoot sperm. I couldn’t imagine not knowing how to masturbate, it seemed like I had always known, or at least I knew from when I was much younger.
I explained to him how boys did it, and made some motions to illustrate the concept. His eyes were big, he said “wow, so that’s’ a real thing that boys do?“
I said “yes, everyone does it.” Then I got bold and asked “do you ever wake up with white slimy stuff in your underwear ?”
He got red in the face again and said “yeah sometimes, is that bad?”
I said “no, its normal. It happens to most boys and even some men. It’s because your body has too much sperm, and that’s how it gets rid of it.”
I told him to go to the bathroom and try it, use spit for lube. and to aim into the toilet... he did. he came out about 2 minutes later with a huge grin on his face and said “WOW..... that was awesome” then he asked if I did that same thing
I said “well, like i said, EVERYONE does it, so yes, I do”
Devin asked how much you should do it. I said “it depends, when you get that funny feeling, you will wanna do it, or when you wake up with a boner, or when you see a cute girl, or sometimes you will just want to do it because you can” I told him i do it twice a day usually.
Then he asked if he could see how big mine was, so I showed him… his eyes got really big and he asked if his would get that big. I said probably, you are still early in puberty. I should point out that I was 7 inches hard at that time, which I still am to this day. He was 4 inches hard, but obviously still had some growing to do.
He then told me his mom had never talked to him about sex, and he was clueless about everything related to puberty. He asked me if I would teach him about it. I told him I would, but I wanted to clear it with his mom first (sometimes parents are funny about that) He said to ask her when she got home. I still had an erection, but had tried to put it in my pants. His mother was due home soon, so I went to the bathroom and masturbated. Devin wanted to see mine when it was soft, so I showed him. He was surprised at the size it was when soft. I told him that his would grow a lot more too.
She got home shortly after and we talked about his game and various things, and then I told her he was asking me questions about “growing up”, and wanted to know if it would be ok if I answered his questions. I was nervous, thinking she might flip out, but she actually looked relieved, and said “oh would you? I know he has questions, and needs to know, but I don’t like talking about that, and it should come from a guy anyhow” I said that I would be glad to talk to him about. She said she would appreciate it.
We went to my house, since no one was home, and I gave him a crash course on puberty, sex, girls, condoms, etc.
Devin knew I had a girlfriend and asked if I had sex with her. I told him yes. He wanted to know what that was like, so I explained how incredible sex felt, and that we always used a condom, to be safe.
The stuff that i had learned over a few years about sex, he had learned in one evening. I told him he could talk to me about anything at all, and never be afraid or shy to ask me. He went home, and called me later that night to let me know he masturbated again, and more sperm came out” I told him good job! We had many talks about sex and things over the next year, and even had some mutual masturbation sessions. We are still close friends to this day, and even though he doesn’t say it, I know he is grateful to me for guiding him through puberty many years ago.