The Bio of a Masturbator

I still had those undergarments and wore them all of the time at night and most of the time on the weekends. The porch roof had become an every Saturday night routine, with some added events. I had taken anal penetration to liking. Since I had no dildo or such to insert into my rectum, I had to use a plunger handle.

Now I wouldn't laugh about it. The first time that I had used it, I was extremely horny and when it slid in me, it must have hit my prostate, because I had exploded all over my blanket before I had the chance to touch my cock. As I said, I was hooked. Spending those nights all alone, moaning and groaning out loud as I fucked my ass and stroking my hard cock. Those really were the days, I mean nights.

Then graduation day came. I was just happy that I graduated. After the ceremony at the high school, I just spent the rest of the afternoon riding my motorcycle around town, bored out of my skull and only wanted to do something with my cock. My only plans for the summer was to enjoy myself anyway possible, before I had to report to basic training. I would have to tell you, that those days were a complete waste, except for the final year and half before I got out. But that will have to wait for another chapter.

That night, I spent it either humping my pillow or with my cock in my mouth. But, while I was fucking my pillow, I had come across a story about smoking sex. I found myself extremely interested in the subject found myself wanting to smoke a cigarette while I was humping my pillow.

Since my father had recently quit smoking, I knew that he had several cartons of cigarettes stashed away. The next morning, he was out doings something in one of his fields, so I made my way to where he kept them and took out a pack. After finding a book of matches, I went to my room and locked the door. This time, I did not even bother to put on anything, I just grabbed a magazine and got on the bed.

After adjusting the pillow under my hips and felt that my cock was sliding along it just right, I opened the pack of cigarettes. An idea hit me to make a game out of this new thing. The magazine that I had selected was aGalleries Girl Next Door special issue, where they displayed all of the entries from the year before. After taking a few cigarette out of the pack, I began to flip through the pages and without looking I would insert a cigarette in the page. I continued to do so with each smoke until there was none left. Then from the beginning of the magazine, I would fuck my pillow to each and every woman until I reached the page that held the cigarette.

The first time I held the cigarette in my lips, my heart was pounding hard in my chest and I almost came from the excitement. As I lit the tip of the cigarette, I drew my first drag. I continued to hump my pillow as I smoked and when the nicotine hit my brain, I felt as if I was in another world. I humped my pillow harder and harder with each drag on the cigarette. The tingling sensation in my groin increased with each thrust. It got to the point that I could no longer focus on the photos in front of me as the nicotine continued it's assault on my brain. I pounded my pillow viciously and with out any type of mercy. I thought I heard myself groaning, but it sounded like it was coming from far away.

Before I had finished the cigarette, I some how managed to set it in the ash tray next to the magazine. What seemed like an eternity, I heard a scream. It sounded like it was far away, but I also realized that it was coming from me. That's when my whole body exploded. I felt my cock shoot hard and then I blacked out.

When I came to, I did not want to move. I felt extremely peaceful and content, but I was just too exhausted to try to move. I laid there for some time before I was able to move. Even then, I was still shaking from the experience and when I had seen what the time was, I had to struggled to clean everything up.

It was around the last part of June in 1985, that my crossdressing began to slow down. With joining the military looming around the corner, I thought it might be best if I would stop doing it. Although it did take a lot of will power, I manage to stop it all together, well for the time being. However, my experimentation did not stop at all. I continued to masturbate even more then I had been and the places that I did it in increased.

It was about the first Sunday in July when I was riding my dirt bike out somewhere on my father's property when I got the sudden urge to masturbate. I really did not like to simply jerk off, I loved to lay on my stomach and hump what ever was underneath me, such as a pillow, blanket, sheet, or even my shirt.

So here I was, out in the middle of nowhere, when the urge hit me. I had nothing to hump. I stopped and turned of the bike. When I got off of it, I looked around for a safe place to do my personal business.(WHIT) I spotted what seemed to be a nice place to have a little fun and I proceeded to take off my cloths. I placed my shirt on the ground and lowered myself on it, so that my cock was in contact with my shirt.

Slowly, I rubbed my hard cock against the shirt. I was determined to enjoy every second of this experience. My hips rose and fell slowly as I breathed slowly. But as usual, with every new experience, the excitement of the moment never lasted very long. My hips moved rapidly and before I knew it, I felt my sperm rising through my cock. I rolled to one side and I cupped my hand in front of my cock, catching my cum as it sprayed from the tip. When the orgasm had subsided, I swallowed the contents of my hand.

After I got dressed, I got back on my bike and continued on my what as if nothing had happened. But I should had really paid attention to where I had laid, because I had laid right on top of some poison ivy. My chest, arms, shoulders, hands and parts of my legs were infected. I had a real hard time trying to explain to my father what had happen.

Once I had recovered from that ordeal, I did not attempt an outdoor adventure ever again, or should I say, with more caution.

The weekend before I was to report for active duty, I had the house to myself. My father was out with his girlfriend and would not be back until sometime Sunday afternoon. This was an opportunity of a life time.

After he had left, I pulled out my girlie cloths and put them on. With it still being light out, I thought that I would like to take a ride on my dirt bike, but dressed up.

The coolness of the evening felt incredible against my skin as I rode along in the pastures. My padded bra bounced with each bump. Thinking back to that ride, it had to be one of the most erotic and thrilling things I have done. My cock stayed hard during the entire ride and when I had returned to the house, I was willing and ready for the night's adventure.

Entering the house, the first thing that I had noticed was how quiet it was, but that would change very soon. I went to my room and out of habit, I shut and locked the door. Since I had bought a VCR player and a small TV, I had a small collection of porn videos.

I put on a video and the scene where Marylyn Chambers gives this guy a blowjob began. I pulled off the girdle and since I was extremely flexible from all of the stretching that I had done, I was able to sit on the edge of my bed and lowered my mouth down to my throbbing cock. As I bobbed my head up and down, my mouth sucked eagerly and I watched the video out of the corner of my eyes. When she started to suck faster, I increased my speed to match her.

When the man started to come on her face, I exploded into my mouth and swallowed my load.

Temporarily spent, I straightened myself up and relaxed for a moment as I finished watching the flick.

It was dark out when the video was over and I moved out onto the porch roof. After the blanket was in place with a few pillows, I went back inside to retrieve a makeshift dildo that I had made out of an old shovel handle. The moon was up and I laid down on the blanket.

Taking the Vaseline and lubing up the handle and my rectum, I lifted my legs over my head, taking my soft cock into my lips. With the dildo in my hand, I eased it into my ass and proceeded to slowly fuck my anus as I sucked on my cock. As my hips moved, more of my cock went into my will mouth. As excited as I was, I had managed to deep throat myself and my balls slapped against my nose.

As I faced fucked myself, I felt the familiar tingling in my balls as I knew that I was close to cumming. I continued on with more vigor as my moans became louder.

Then without warning, the first spurt from my balls shot into my mouth. My hand, which held onto the dildo, violently thrust it in and out of my ass as screams of pleasure escaped from my cock filled mouth. I had came harder and more then I had ever done before. I could not swallow fast enough as sperm escaped from my lips and dripped down the sides of my cheeks.

I could not take anymore as I yanked the dildo out of my ass with such force that it slipped out of hands and slammed against the side of the house. I stayed in that position, not wanting to miss anymore of my cum.

When my orgasm subsided, I slowly lowered my legs down to rest. As I rested for some time as I kind of regretted that I had to leave in a couple of days.

When I had recovered some, I retrieved my dildo and when back at it some more.

The sun was just peeking over the horizon when I felt completely drained and after I crawled back into my room, with the blanket in tow, I crawled into bed and did not wake up until that evening.

This is the end of this part of the story. Please rate and comment if you like the story so far and let me know if I should continue on. Thank you for reading.