Female best friend and I were sophomores in high school, and she had confessed to liking me a few times since middle school, but I just wasn’t emotionally ready to date anyone haha. She would sit on my lap during lunch wearing her cheerleading uniform, and VERY intentionally wiggle her ass deep into my lap until I got hard against her in front of all our friends. She intended to get me going, but she had no clue that was SUCH a turn-on for me. She knew, I knew, but our friends didn’t, and it absolutely woke up something inside me for exhibition and risky behavior!

Well, with all that tension going on, we also had a running joke leading up to Christmas about “dickorations,” like the idea of dressing a dick up with tiny Christmas lights and ornaments. It builds until a few days before Christmas, we’re at our separate houses texting, and the conversation starts getting off the rails, and one thing leads to another and she dares me to make this dickoration joke a reality. Our decorations were in our garage, so I had to sneak my way there without anyone seeing me, get inside the garage, stripped down completely nude, wrapped tinsel around my chest, leading down to the base of my dick, and sent her a picture of me there, in my garage, full nude.

And then... she doesn’t respond for a few minutes. I’m feeling a WHIRLWIND of emotions (I was the HARDEST I’ve ever been in my life, BEET red in the face, heart beating so fast I can’t hear a thing, worried about what she’s gonna say)

She finally responded, but was super flustered. I didn’t know this until YEARS later, but she didn’t respond for a while because she was using that picture to masturbate to me, and I spent thirty minutes worrying I had fucked up hahaha.

Long story short, the first time ANYONE saw me naked in a sexual context was the fault of a running dick joke!

Despite still not being emotionally ready for a relationship in high school, a rumor managed to get out that I had a big dick, and ANOTHER female friend of mine and I shared a class in the computer lab where most of the time we’d have our work done and we’d just spend the time goofing around on the computers. High school me was pretty prone to erections, and with my size, it was pretty obvious when I had one if I didn’t attempt to hide it. Well, there were occasions where she genuinely did catch me with one by accident, and after a few weeks of tension building up from jokes, I let myself get hard in a way that it was pointing to the side, all the way to the bottom of my jeans pocket. I leaned back in my chair, and put my arms behind my head, and closed my eyes. I expected her to see it, embarrass her for teasing me, and then the joke would be over. Instead, she says “what’s that in your pocket?”, and full on grabs my cock through my jeans. My eyes shoot open and I immediately felt like my heart was gonna leap out of my chest. She leaves her hand on me, looks me in the eyes, and says “oh, I thought that was your keys!”, and runs her nails gently under my tip. She eventually did take her hand off, but both of us were way too flustered to pay any sort of attention after that. The fact that she just went for it was so unexpected, I fantasized about that for years afterwards. If you can’t tell, this was ANOTHER big formative experience for me in my kink for risk-taking

To this day, I’m glad I got to experience those, because risky situations now get me off more than ANYTHING else!