I originally posted the story below as part of my answer to another question - someone suggested I repost under another heading - so for what its worth...
I just loved going commando as a kid (still do obviously) - but it felt so wonderfully naughty - especially because you could do it - and no one knew. I had the distinct pleasure of being the one to introduce my son to it when he was 9 - I acted very "conspiratorial" even though I knew my wife wouldn't care. We were going out to dinner and I was shaving when he got out of the shower. He watched me for a while - as he often did - and i asked him if mom had laid out his good clothes, and he said yes. And clean underwear? Yes. So I whispered - what if tonight...we don't wear any underwear. He giggled uncontrollably. So I said, I won't if you won't. But don't tell mom, ok? It was obvious he loved this idea. As we were getting ready I went to his room - I hadnt tucked in my shirt yet and he was just putting his on - I pulled back my pants to show him I didnt have any underwear on - and he did the same. We both cracked up and finished putting our shirts on. My wife came by and wanted to know what was so funny and I said "ah just guy stuff." The two things I noticed that night were that a) he took more trips to the bathroom than any previous outing, and he had his hands in his pockets more.
Although I never told my wife specifically about this - she sure was pleased to find one less layer of clothing to deal with when we got home.
I've been lurking - and just read my post again and realized I hadn't responded - sorry! Well here it is...better late than never. One thing I forgot to mention was that another result of that first outing commando, when I put him to bed that night (we had gone to dinner and a movie)he took off his clothes and I suggested he just hop on into bed. My wife came in to kiss him goodnight - no idea he was naked as a jaybird lol. Again - not that she would have cared, but you could tell he was both nervous and excited. Ah to be young again!
thats a funny story on how your son started freeballing....
I bet he loved freeballing, but thought it was weird and too loose at the same time (He did love it - and did it with greater frequency - the great thing was that for about 2 years he always "let me know" lol)
and i bet he played with himself alottttt that night with his hands in his pockets and in the bathroom.... (that did seem to be the start of it - my wife noticed that to)
sorry if this sounds too personal, but I am guessing he wore briefs, like most boys do at 9, is that true?? (At the time he wore briefs/tighties - he then got some boxers and jocks as he got more into sports. Now the only jocks he will wear are the narrow band jocks.)
how long ago was this and how old is he now?? (He was 9 when this happened - 12 now.)
did he keep freeballing and eventually stop wearing underwear?? (He does both - I guess he freeballs about half the time - almost always in summer.)
do you freeball part time or fulltime, and how often did u freeball then??? (part or full time...) I go both ways! lol I wear underwear sometimes - and sometimes I don't. Depends on the day, the situation, and my mood.
lastly do you remember what pants or shorts he wore the first time, because what a guy wears while freeballing the first time can be different against a bare ass and bare balls/penis.... (The first time he was wearing dress pants. The wife did get a bit of a show when he had shorts on one weekend and was watching tv - didnt realize his package was visible - but it was. My wife looked at me and laughed as she said oh god, now theres two of you. lol)
I like underwear - SOMETIMES! I also like going commando. I like my wife in underwear - but am always pleasantly surprised when i find she isn't wearing any. So, like all boys, he was brought up on briefs - has now expanded to boxers, trunks, and jocks. And - like the all-American boy he is - goes without sometimes. We don't put any particular restrictions on it - whatever he is comfortable with. He's 12 now - so well old enough to make those kinds of decisions, we think. Sometimes we hang out in unders - sometimes not. He didn't even realize his mom was totally ok with his going commando for almost a year! lol