When this happened, I was 16 and I had already been masturbating for a few years. I learned to masturbate on my own, back when I was younger, but that's for another story. I never had the talk from my parents, so I learned the rest from school, friends, and my dad's porn collection. When I was home alone, I would masturbate regularly to the videos. I would always put in a video, take my pants off and sit on the couch slowly stroking my 6 inch cock until I would blow my load all over myself.
This one particular day, my parents and sisters were all out of the house and I knew they were going to be gone for several hours, so I figured I would treat myself to a nice session with the help of one the videos. This tape I watched was a tape that I had watched several times before because there was a scene of a woman masturbating in the bathtub, it always turned me on and always got me off.
So I got the video tape, and went through my normal routine; put in the video, take my pants off and sit on the couch. While I was watching this beautiful woman get herself off, I slowly stroked my cock getting closer to blowing my load. When she started cumming, I started blowing cum everywhere. As I sat there collecting myself, the video had ended and went to white static. As I sat there, rubbing my fingers through my cum, I saw something come on the TV. I saw our couch and my dad walk into frame completely naked. He had recorded himself masturbating! I was so intrigued since I had never seen my dad naked before, so I kept watching. As the video went on, I couldn't take my eyes off his cock as he slowly stroked. He had such a beautiful cock, about 7 inches and with a full bush of hair above it. I was starting to get turned on again, so I started stroking my cock as I was watched my dad stroke his cock on video. I couldn't believe what I was doing, stroking my cock to a video of my stroking his cock. While I watching, my dad reached off screen to grab a dildo. I couldn't believe what I saw. He put the dildo on the ground and squatted over it and slowly inserted into his ass. I stopped stroking because I couldn't believe he was doing this. He let out a loud moan as the dildo slowly entered his ass. Once in, he started bouncing up and down on it and started stroking again. For some reason, I got extremely turned on watching that I started stroking again. After about 10 minutes of watching my dad ride a dildo, he let out a load moan as he started spraying cum everywhere. Just as he came, I blew another load all over my myself again. It was a great orgasm and I couldn't believe I just got off watching my dad masturbate and ride a dildo. After I recovered, I put the tape away, but couldn't stop thinking about what I saw. Then I started thinking about what a dildo in my ass would feel like as I masturbated.
About a week later, I was home alone again and decided to treat myself again. As I was looking for a video in my dads drawer, I found the dildo that he had used in the video I watched. Then I got the idea to give it a try to see what it would feel like. So instead of grabbing a video, I grabbed the dildo. It was about a 7 inch dildo with a nice girth on it. I went out to the living room and took off my pants just as I always had. I had always used spit as a lubricant, so I spit on the dildo to rubbed it all over making sure it was nicely lubricated. I put the dildo on the ground and started to squat down on it. I could feel the dildo slowly open my ass and I remember hurting so bad that I was sure I would be able to do it, but I really wanted to know what it felt like, and I had never had anything inserted into my ass before, so I put some more spit on it and tried again. I started squatting down on the dildo slowly again as it started to go into my ass. After about 5 minutes, I was finally felt the dildo slide in and I took the whole thing. After the pain subsided, I grabbed my cock and started stroking because I was already hard. I slowly started moving up and down on the dildo, stroking my cock in rhythm. I could not keep quiet as I bounced up and down the dildo because it felt so good and it was a feeling I had never experienced before. I was letting out loud moans as the dildo went in and out of my ass. I knew I was getting close to blowing my load, so I started bouncing up and down quicker while a stroked in rhythm. When I started to cum, I squatted all the way down on the dildo and let out a huge groan as I started blowing cum everywhere. The feeling was so intense, it was better than any orgasm I experienced from previous sessions. As I sat there, dildo still in my ass, I collected myself from what just happened.
From that point on, my masturbation habits had changed. I would try to use a dildo at least once a month, or when I was in the mood for an intense orgasm. I would have never tried it if it wasn't for my dad. We never talked about it nor did I ever ask my dad about it, which is why he unknowingly showed me how to masturbate with a dildo up my ass.