JCDakota
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I remember my first jock when my dad has gone over the checklist for little league and summer sign up for a class i was taking for summer school and was surprised that my mom had got a jock already.
He asked me how it fit and I said it was tight and it hurt my tummy. He said in a joking way, something to the effect of: "you aren't that big down there Tiger... still got some growing to do..." and I said that it was tight on the waist and it just was uncomfortable. He thought I was just un-accustomed to tighter fitting undergarments so he told me to put it on and he'd do a finger-in-the-waistband check. I pulled down my shorts and started to put on my jockstrap while my dad went to his den to get a sharpie to label my things. He came in and chuckled a bit and told me that I had to take off my underwear, and that "men" don't wear underwear with jockstraps. So with my really tight jock around my thighs, slid down both my undies and my jockstrap. The two garments got rolled up with each other, and I distinctly remember bending down to pick up my jock and standing there a minute or two with a raging hard-on while I tried to untangle them from each other. After what seemed like too much time, I tried again, this time getting the jock *almost up to my waist, but stopping short, trying to stretch the band over my waist, with my erection sticking upward, caught in the waistband.
My dad reached down and pulled off my jock, and left the room. He came back and gave me a different kind of jock strap from his room and held it up to my little one. He then took another one that was between the sizes and had me try it on. It was too big and didn't fit me at all. My dad then took my XS jock and made it a S by stretching the band with both his hands and snapping most of the elasticity. I remember hearing the tearing sounds and wondering why the hell my mom didn't do this for me earlier.
I put the jock on again, and it was still tight, but I was able to slip it on. I tent-polled the entire time and I will never forget my dad saying this: "Stick your fist and stretch out the crotch" I had no idea what that meant, and before I could ask, I heard the sound of my dad's shorts dropping to the ground and I managed to look over as he reached for the large jockstrap and watched as he effortlessly stepped into it one leg at a time. I watched him slide his penis inside and move it to the right. Had I hit puberty, I'm sure I would have ejaculated right then and there. He grabbed his jock from the bottom straps below his sack and gently stretched out his jock by using a fist from the other hand. He reached over and did the same with me and then re positioned the contents of my pouch. "You can point it up and it stays hidden" he said and gave me a wink.
I was slightly embarrassed and I think he knew it, because he looked at me and said: "you look good! Now you're ready to play some REAL ball" and told me to run to the end of the hall and back. He asked how it fit and I said it was better, but still a bit tight. He said it was supposed to fit snug, and we hung out for a good hour in only our jocks and tees, oiling the mitts, and carefully tossing hte ball back and forth on the side of the house before it was time to go to practice. I felt so grown up and close to my dad, and he even lightened the mood by pointing out how our butts were free and that we could see each others.
Before getting dressed for practice he told me to pee before putting on the cup. I went to the bathroom and tried to pull down the waistband to pee. I didnt see that my dad had followed me into the bathroom and simply said: "No son, like this" He reached out of the right side of his jockstrap and pulled out his dick. My little 12 year old dick instantly swelled up and once again I was tent polling. I watched for a brief moment as I saw that thick stream of piss come out of his piss slit and splash fervently into the toilet water. Before I knew it, he was done and gave his dick a little milking and tucked it back into his jock. I could see a little wet spot bleed through the fabric. He teased me and told me to "stop dicking around and pee" as he left the bathroom. I eventually peed and suited up. We arrived at practice and I told my dad that my stomach was hurting. The other coach was present and gave my dad a look. Right then and there my dad told me to open my pants and see how the cup was fitting. That too was too small. (even for my pre-pubescent anatomy). Long story short, I took off the cup and I was put in outfield and practiced pitching and throwing and was told to watch out for my nuts...
My dad and I went to the navy exchange (also a navy brat here) that late morning after practice and bought me 2 size S jocks in men's (not youth) and 2 cups. He also bought me a swimmers jock in M. I went home and he made me try on all jocks. The Smalls were good, but stiff and the medium was a bit loose, but it stayed on. the pouches in all jocks were small enough to house my goods. :) I still stretched out the crotch like my dad said, and before hitting the showers, my dad told me to add my jocks and pants to the washer and do a load. We both undressed in his garage, threw our gear in and showered for lunch.
I liked seeing both of our jocks mixed together when they came out of the dryer. I thought I was coy, but I slept in my jock that very night and experimented with putting it on backwards and letting my erection stick out the sides. However late that night when my dad came to tell me lights out and I was laying in bed wearing my jockstrap backwards and moving my hips so my dick was pointing straight up at the ceiling! I was embarrassed and laughed it off as I pulled over the sheets and blanket. My dad smiled and said I could wear my jock whenever I wanted, but that I shouldnt wear it to bed. He made me get out of bed, take it off, put it in my drawer before I could jump back into bed. The jig was up though the next morning when my dad has found my rolled up jockstrap next to my bed, which proved I had played with it during the night after lights out! :)
I think of this story, and I’m sure my son has done the same. It’s jaut one of those things I guess