Story Details

Best Orgasm ever in my life

penispounder on Masturbation Stories

This is a true story and really happened

When I was just a boy I realized that women’s clothing was softer and sexier. I started to steel panties from my sisters and loved the way they fit and felt,When I was just a boy I realized that women’s clothing was softer and sexier. I started to steel panties from my sisters and loved the way they fit and felt, it was so smooth and hugging. I would wear them to school. Then I moved up to pantyhose, skirts and blouses. I would go out at night sneaking them out, finding a secluded place like the high school stadium, put them on and walk around. I would always get to horny and end up beating off. When I was old enough to get a car I had a place to hide my collection and would also drive around fully dressed in women’s clothing.




It was making me so horny I would constantly find new more exciting ways to jerk off. I would do it while driving army trucks, in public, in the garage, with any kind of lube I could find, laying on the cold cement floor of the garage, anyway that cum to my mind. Yes always with some sort of women’s clothing on.



Later in life I would have to wait until my wife was at work and then the whole house turned into my private little whore house where I abused myself. By this time I owned only women’s panty’s and wore only them. I started shaving my balls and dick and soon moved on to my belly and ass, then my whole body. I was then so smooth and silky. I had also discovered that I had two yearning holes and was putting almost anything in them as I jerked off. I would put broom handles, dusters, shovels, racks, lift was round it went in my ass. Each time deeper and deeper until I could see my belly bulging. I put pencils, pens, silverware, hoses,and sounds in my dick. WOW I was having so much fun. With the hoses I would fill them with cooking oil and blow it in my dick as I inserted it, I got up to 36 inches into my dick. I love it.



One day my wife left for work early and I dressed up with stockings, garter, a bra, heels, and a full length slip. I filled my but with oil and a large dildo and went for a drive. I auto cummed all over my self while driving. As I pulled into the garage I saw it out the corner of my eye, the ultimate thing to shove in my ass. I was so excited, I ran into the house and got the cooking oil. When back to the garage, still dressed up, pulled the dildo out of my ass, found the funnel, went to the wall and did a shoulder stand against it, put thefunnel in my ass and dumped ¾ 0f the bottle in my ass. Then I got the hose and sucked oil into it and inserted it into my dick blowing the oil out as I went all the way in. once I was oiled up, I went over to it, a wheel barrel. I sat it down and pushed the front against the wall. I got on my knees, lifted the slip up and backed into the handle. My ass opened up and accepted the 2 inch handle right in. I threw the slip over it and kept backing on as I looked under me to watch what was going on, there was my bald dick and balls hanging there, drippingoil, and hard as a rock. I reached under and smeared the oil all over my balls and dick as I began to play with myself. I kept pushing the wheel barrel handle deeper in me as I massaged my balls. I went so deep I went beyond where the handle went from round to square, two feet in. I was so fucking horny I could not believe it. Oil was gushing out my ass and I began to cum over and over out the hose in my dick. I reached down and put it in my mouth. The orgasm was so much I fell over pulling the wheel barrel over with me, almost passing out. Once on my back I had to gasp for air and cum drooled out mymouth all over my face, down my cheeks, onto my eyes and chin. It was fantastic. I laid there for about an hour pissing oil all over me as I massaged myself. Then I rolled over pulling the handle out of me and released the oil out of my ass letting it run between my legs and up my back. I felt sensational covered in oil and cum.




After I calmed down, I placed a piece of plastic over the seat of my car, got in and went ti the edge of the woods. As I walked into the woods, totally alone covered in cum and oil, still with the hose in my dick, I started stripping. Somewhere around the 2 mile mark I was totally naked and felt wonderful. I walked back to the car with my soaked cloths over my shoulder feeling free as a bird and so proud of myself.




I still fuck myself with the wheel barrel and everything else I can find, but have never had such a great orgasm.

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