Justin and I had grown up as childhood friends and always were spending the night at each other's houses. He was very open with his sexuality, but I was extremely shy and nervous. Every time I spent the night at his house, he always wanted us to look at each other, but I could never get up the guts. That all changed a few years later.
Our first year in high school our parents decided to rent a cabin in Maine. There were no extra beds, so Justin and I had to sleep on the floor downstairs. Late that first night we started to play Truth-or-Dare. It started off with stupid things like mooning out the window, but as the night drew on things took a more sexual tone. I had never told anyone that I masturbated as my father had told me it was a sin to do it, but I had always wondered if anyone else did. Justin chose truth, and I asked him what his darkest secret was. After a couple of minutes he told me that he masturbated.
I couldn't believe it. My best friend did the same things I did. He immediately asked me if I did and I shyly responded yes. By this point it was extremely late, but little did I know what would happen next.
The next night after everyone else was in bed, we skipped straight to truth-or-dare, but it was completely different. I dared him to masturbate on the chair for 15 seconds, and he got up, but then asked if he could do it under the covers, I said yes. He started humping the ground, and I couldn't believe what I was seeing. I had never tried humping before as I had always used my hands. He dared me to do the same thing. I had lost all inhibitions by this point and willingly agreed. After several exchanges of the same dare we decided to see who could cum first. We sarted masturbating like mad, me pumping with my fist, and him humping and moaning. Unfortunately, Justin finished first. All of a sudden he started moaning and gasping and then his hips bucked as he came. I wasn't far behind him and came into my boxers, covered in cum, we both went to the restroom and cleaned up. We went to bed right after, but everynight it was the same story, of me jacking with my hand and even being taught by Justin the joys of humping pillows. It was a week to remember.
We never did this again, and are now regular straight guys, but I will never forget those nights in the cabin.