This was a few years ago when I was 11 but almost 12. Summer just started and during the day a girl, Maggie, would watch me when my mom was at work. She must have been 16 because she just got her driving license and always looked for reasons to drive me somewhere just so she could drive. She was the first girl I thought of as being hot. She had large tits, or I thought so, and when we were home she would often be in just a shirt without a bra or wear just a bikini. She would often hug and cuddle me and it would give me boners.
One morning a few days after school, she took me to sign up for baseball and that year I moved up to the 11 to 14 year old league. We got uniforms but we were told we had to buy our own athletic supporter with a cup and they were mandatory. I didn't really know what one was except that it replaced underwear for bigger boys when they played sports. Maggie asked if I had one and I said no so she said we would get one. I was really embarrassed about it. My mom always bought my underwear and stuff and never had to talk about it. I had no idea where to go to even get one. Maggie was a bit clueless to but she called her boyfriend and asked him to take me but he was working and couldn't but she told Maggie where to go and stuff. So we go to this one sport store at the mall and we find them in the store and there are all kinds and stuff and we don't know what to get so Maggie gets this girl that works there to help. It was so humiliating with them talking about all the kinds and what I would need and stuff. They made me open my pants so they could look at the tag of my briefs to see what size I wore. The girl even said what cute Spongebob Squarepants you have or something like that. It was even more embarrassing when she asked if I was developing. At first I didn't know what she meant, all I could think of was developing film and I couldn't understand what film developing had to do with buying an athletic supporter. I just asked, 'What do you mean?' Maggie says, 'You know.' I asked, 'Developing what?' I didn't have a chance to even close my pants yet and without saying anything Maggie pulled the front of my underwear open, looked in and said she thought I would probably need the smallest size they had. I figured out what she was talking about. They couldn't find one my size and called the manager over to help. He said they don't sell many my size and had to go in the back to find one. It took forever for him to get back. I thought if he didn't find one I would rather quit baseball before going to another store and go through that again but he came back with a supporter and another box with a cup. Maggie paid for it and we went home.
I didn't talk the whole way home and Maggie told me to go to my room right away and try on the uniform and make sure everything fit so we could take it back that afternoon. I didn't have a problem with the clothes but I really couldn't figure out the supporter and cup. Underwear was easy but this thing was a bunch of straps and pockets and even though I read the package I couldn't get the hard cup to fit in the pouch it belonged in. I finally gave up and just put on the uniform with my underwear and I would figure out the supporter later.
I showed Maggie and she asked me why I didn't try the supporter. I told her I couldn't figure it out and she told me to get it. I didn't want her to have anything more to do with it and I tried to convince her I would handle it but she had to see right away and made me get it for her. I stood there while she played around with it and she called her boyfriend again. She was doing different things and as she did her boobs were jiggling around and I could see her nipples through her shirt. I was getting a boner and was about to leave the room when she told me to take off my uniform and try to put it on. I was about to take it and she told me to try it right there in front of her because she had it figured out. I hesitated a little because I wasn't sure what to do and she told me I didn't need to be embarrassed because she has younger brothers and saw a lot of boys naked babysitting and stuff. She then just reached over and pulled my pants down to my ankles and told me to hold up my shirt and she pulled my underwear down. I was a little embarrassed but my mom saw me bare a lot and often after my bath when I had a boner. I didn't think much of it only that I was bare.
She held the supporter in front of me and I stepped out of my clothes and she told me where to get my feet. I felt a little foolish since it looked so simple once I did it. The problem was my boner didn't fit to good in the cup and was pretty uncomfortable. Her boyfriend told her if she hit it right where my nuts are and it didn't hurt it was probably on right. She tried it and it hurt my penis and I complained. She pulls it off again and said maybe the problem was that is was hard and she knew how to care of it from helping her boyfriend. Without saying anything she grabbed it with her fingers and started stroking up and down. I did that many times in my bath but it usually only made it harder. I didn't see how it would help. She told me to lay down on the couch and she started stroking it faster and faster and then I had an orgasm. It was the first one I ever had and I thought it was the best feeling ever. It was dry but still felt great. My penis went soft again and we tried the supporter again but it still didn't work right. We took it back and found out it was the wrong cup and we got the right one.
When we got home again I tried it on again and Maggie helped me with my boner again. It became a regular ritual every time we had a game and I had to put the uniform on. I love baseball that year and I joined football after that. I don't need to tell you why.
The next summer Maggie would watch over me again. I was 12, almost 13 and started puberty sometime during the winter. I had hair but Maggie was there sometime on a hot July day when I squirted my first cum on her hand. I'll never forget her.