First Time Discovering Bear / Daddy Porn
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Since I reached puberty, I was always attracted to mature men. The typical gay men portrayed in media and through the gay scene did not appeal to me whatsoever. For that reason, I did not consider myself gay for a long time. I did not know there were other gay men who appreciated what I did.
I have been online for a significant period of time (i.e., before there was even a proper browser). Sometime in the late 90s someone (straight) jokingly told me to join a chatroom called "bearcave." The topic in the chatroom had a link to a website with dozens of pictures of hairy and mature men. That's when I discovered that there was a subculture of gay men who appreciated the look of a real man.
Prior to that, in the mid-90s, I encountered the "Sheriff Parker" stories. These were a series of erotic stories about a chubby, extremely dominant, sheriff in a southern town who could not get enough cock (you can still find them online, and even today they are hot to read). This too was a major discovery for me.
So when did you first discover bears / daddies? If it weren't for the Internet I do not think I would have ever come to understand my sexuality and find like-minded men.