It’s my belief that you can’t escape embarrassment while having a sex life. We all have at least one moment where we wish a particular moment didn’t occur, but let’s face it, those memories are pretty hilarious even if we never share them with anyone. Ever.

Luckily for you, I’m not like others and I love sharing embarrassing moments. Although I did mention it, this story is not about sex in the traditional sense of the word. No, this is about sex with yourself, or as the pros call it, masturbation.

Penises should come with a manual…

At around 13 or 14 (they’re both the same age to me) I had already experienced hand jobs and blow jobs from a couple of girls but still no orgasms or masturbation – they go hand in hand right? So, alone, watching late night softcore, I figured the time had come to attempt my first masturbation session. Without going into the details of how I came to get an erection I’ll cut to the chase… I had a boner so I decided to rub it and see what happens.

There I was, standing in my dark room, stroking away like a man possessed, waiting for something magical to occur. Penises don’t exactly come with an instruction manual so I wasn’t exactly sure what to do so I just closed my eyes, thought about boobs and kept at it. I figured I was doing something right because it felt pretty good and on a couple of occasions thought I was cumming so I stopped and waited for whatever was supposed to happen next. Nothing. Frustration started to set in after a few times of failing but my determination wouldn’t let me quit. I was told magic was at the end of this road and I needed to experience it.

After some quick thought, I finally realized that my best bet for an orgasm would be to continue stroking without stopping to see what happens. An obvious solution for an unknown outcome. As I continued to stroke I knew I was nearing the end by the unusual, yet exciting, sensations coming from places I’ve never felt before. Persevering, a new sensation started at the base of my erection and began to slowly make its way upward. Feeling this for the first time I became nervous, and of course, very excited. There was no way I was going to stop this time. This was it. The grand finale. As the feeling made its way to the head of my penis, my body tensed up and quickly relaxed, giving me the okay to ejaculate.

The warmth, the feeling of relief and relaxation was cut short when I realized it wasn’t cum and I was in fact pissing all over the carpet of my room. Thinking quickly I tried to cut the stream off by tensing and squeezing the head; running quickly to the bathroom.

As I finished taking a leak, in the bathroom this time, I couldn’t help but shake my head and feel like I had just let myself and my penis down. Not to mention the enormous feeling of embarrassment I was experiencing.

Needless to say, I waited a while until I tried masturbating again…

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