As a young boy when I was left at home alone I would explore the area of the house that was always forbidden to me, my parent's bedroom. During my first such exploration I found some of my mother's lingerie hanging in a walk in closet. I soon began to wear the lingerie to masturbate in. My favorite piece to wear was a crotchless lacy teddy with matching stockings.
While wearing the teddy, stockings, and a pair of mother's heels I would search the bedroom for any other material I could use in my masturbation. In my mother's night-stand I found a pink, rubber dildo. It had ball on top with a shaft that was a little bit smaller in diameter. The shaft had little ribs and ended with a knob that had two switches on it. I moved one switch and the dildo began to buzz and vibrate. I then moved the other switch and the dildo began to wiggle. As the dildo vibrated and wiggled in my hands, ideas popped into my head. Looking back into the drawer I found a tube of K-Y jelly. I grabbed the tube and ran to the bathroom.
I had never done this before but I had an idea of what to do. Once in the bathroom I lubed up the dildo. I then lay on my back and positioned the ball on the top of the dildo at my asshole. I slowly began to exert pressure but the dildo would not go in, the ball was too big for my virgin asshole. By this time I was shaking with excitement and did not want to give up. I tired a switch of positions.
I placed the dildo so the ball end pointed straight up in the air. I then squatted over it and slowly guided myself down so the ball of the dildo was centered at my asshole. I then began to take the weight off my legs and put it onto the dildo; I could feel it slipping in. Suddenly, the entire ball portion of the dildo popped in. It hurt so bad that I had to immediately pull it out. I crouched there for a few moments gasping for air and relaxing my nerves; I had gone too far to give it up now. I sat the dildo back up, centered my asshole, and slowly pushed down. It popped in a second time, and to my satisfaction, with a lot less pain.
After a few minutes of absorbing the pleasure of finally having the ball end of the dildo in my ass I put more of my weight onto the dildo. I could feel each rib pass into my ass as I slid further and further down onto the dildo. It felt so good to have this thing inside of me. I began to slowly hump the dildo by pulling it out till the ball just about came out and then sliding down to the base. It felt so good I started going faster. I kept it up until my legs became sore. I then remembered the two switches. I turned one and the dildo buzzed into vibration. After a few moments of that I moved the other switch which sent the dildo wiggling while in my ass.
My penis was as hard as a rock and dripping pre-cum. As soon as I touched it with my hand it exploded. The orgasm was so intense I feel forward. I had to lie there for a few minutes to catch my breath and allow my nerves to relax. I then cleaned myself up as well as the dildo and put everything away. After that whenever I was left home alone I would put on the lingerie and fuck myself with the dildo.