By @billiesoniq

My story starts in a small town just outside Seattle, back in 1990. I had just moved to a new town, starting a new school. There isn’t much to say about this backstory – my mother started a new career, and I was the last child still young enough to live at home.   As a single mother, she felt it necessary to get me exposed to as much ‘guy stuff’ as possible. This meant that I was supposed to at least ‘try’ sports, boy scouts – anything and everything that would supplement her idea of what I was missing without a father figure in the picture.

Up to this point, I thought it was torture. I didn’t want to go out for sports, I didn’t want to chase after a ball, or learn to light a fire with steel wool and a rock. I wanted to read books, write stories, and learn about these new computers that the last few schools I had attended now had. That was, until Joe Joe came along.

Soon after we moved to this little no-name town, my mother befriended one of the local neighbors. He was an athletic man, about 28, with a permanent tan. He choose a bicycle as his only means of transportation. At the time, he played it off as a way to keep fit; adulthood now leads me to believe that he had no other options at the time. Regardless, I was immediately drawn to him. He was a guy’s guy. He swore without regret, and went shirtless to the grocery store. To me, he was the exacting idea of what a real male should be.

Which leads me to my first inkling of interest in men’s underwear. At one point in the summer prior to my first year at my new school, my mother and I were invited to a local swimming hole by Joe Joe and two of his buddies. We packed up our swimming clothes, hopped in the car, and Joe Joe lead the way to a secluded lake, about 15 miles away. After a quick unloading of the vehicle, mother and a few girlfriends met up and started to drift towards a cabin. Confused, I started to follow. No one had told me what was going on. Joe Joe, noticing my confusion, called me over. I remember this part pretty much like it was yesterday. He tousled my hair, pointed to another cabin, and said, “Hey little man. The men’s cabin in that way. You’re a guy, you come with us.”   Honestly, this was the one of the first times I was included as ‘one of the guys’. Not willing to miss this opportunity, I followed the other guys, and Joe Joe, into the small cabin.

Once I was there, I was unsure what to expect, and certainly not expecting what I saw. I walked in, and there were at least 6 guys, all different ages and sizes, in varied states of undress. Obviously, seeing a bunch of guys in that state was rather embarrassing for a 10 year old, especially since my brothers and father were not really around for me to be accustomed to that.

I started to stammer. I didn’t know how I was supposed to react, and Joe Joe, who had now become sensitive to my confusion on this whole situation, reacted in probably the most constructive way any father figure could have ever done. He pulled me aside, and simply laid it all out for me. His words, as best I can remember, were simple, and flat out honest. “Billie, here’s the thing. Guys change in front of each other. Everyone looks, and everyone has the same junk. Don’t be shy, don’t stare, and don’t worry if people peek at you. It’s all out of curiosity, and that’s ok.”

At the time, it really helped. I wasn’t really into it for the sexual part, at the time; what really fascinated me about the situation was that all these different guys were all wearing different underwear than me. Until this moment, I had only known of ‘tighty whities’ that my mother had been buying for me to wear.

Older guys were wearing what I came to know as boxers; the teenagers that were there had on briefs, like me, but wait – they were in different colors! How cool was that? It was then that I saw my first bikini brief, colored brief, and even a makeshift boxer-brief. I didn’t know what they were called at the time, of course. I did know, though, that I wanted to see more. I wanted to try more.

Over the next couple months, both goals came to fruition. Between soccer practice, baseball, and physical education in school, I was a casual observer to almost every brand, style and type of underwear available to the 10 to 16 year old age group. I gained a sense of courage from the experience as well. It was that year that I convinced my mother how I was old enough to buy my own underwear. I decided in my mind that this was something special to men, and that as a man, it was up to me to decide what I should wear under my jeans, and what I needed for sports.  It was also the year that I had to find out what a jock strap was, how to wear it, why we needed them, and how attractive they actually were. Believe it or not, Joe Joe was helpful in that area too, since he was the only man in my life that was willing to tell me how things were. With a bit of fear in my mind, but a sense of manliness, I was able to walk over to his house, sit down in his living room, and tell him that school needed me to get a jock, and ask how that worked. Thankfully, he was just as cool as before. He offered to go with me, but in the end, I was able to man up and get one on my own. I even figured out the sizing of the waist and cup, all without help.
After that shopping experience, I was pretty much hooked. By age 16, I had easily 30 favorite pair; I was confident, unashamed, and completely interested in any store that carried variety. Of course, by then, I had also realized the attractiveness that comes from the right guy in the right set of undies, and the appeal and feel of certain styles and brands… but that’s another story for another time.

NOTE: Brief Tales are posts from our staff and readers in what got them into underwear. If you have a story you want to share email us at timothym@underwearnewsbriefs.com and let us feature your story.