1. A young man's summer [full story]


    Date: 9/8/2017, Categories: First Time Masturbation Shemales, Author: serious58

    ... be older women, perky tits were nice, but big nipples and open pussy lips were a major turn on for me. Seeing them online made my mouth water sometimes. I had collected a vast array of photos and video clips that I would play and jerk off to while watching. By the time I was 15, John had moved out, attending college a 100 miles away from our home town. I found the freedom of having the house completely to myself for a least a couple hours everyday and nearly all summer a fantastic way of life, I rarely wore any clothing during these private times and roamed the house, my cock bouncing freely like nature intended. I don't know that I jerked off more than before [1 or 2 times a day], but my interests began to widen, a significant influence happened one night when I was watching some gay porn and found a section that had bunches of guys riding dildos and cumming 'hands free'. I researched this and found out about prostate milking, which sounded like a hell of a lot of fun to me! I had always enjoyed playing with my butt hole and often pleasured myself as deep as I could get two fingers up in me while jerking off, I found that there was a certain spot that I could reach if I got on the edge of the toilet sitting on my hand, with my middle finger crammed up my ass, it felt incredible and made my cock explode in some major cum shots. But I found that my finger wasn't quite enough to do the job like I was seeing in the videos, so I started looking around the house for various ...
    ... things I could use for anal stimulation. I tried lots of things; hammer handles & the old standard plungers were the first, but I didn't like the feel of wood, plus they were hard to clean the slippery off of. [I did not want Mom to ever ask why the plunger handle smelled like baby oil!] Different kinds of vegetables were sometimes an option and I would frequently buy a good sized cucumber when I went to the store for Mom and would keep it back for play time, I practiced incremental ass stretching but soon found that I had a limit in size, about 2 3/4 inches in diameter was all I could ever cram up my hole, it felt like it was bone to bone in my pelvic opening. For the first few months of my anal experiments, I tried nearly every type of drink bottle there was at the local convenience store. A great revelation came when I got home from a softball game one day and was feeling supremely horny. I debated several things but it suddenly dawned on me that my aluminum bat was just about 2 1/2 inches in diameter, it hadn't been used but in a couple games, and was still nice and smooth too, the thought of sitting astride it made my cock jump and drip in anticipation. I got my bicycle tire pump and went to my bathroom, filled the sink with warm water and greased my ass. Placing the pump in the sink I pumped it until the air was all expelled and it had filled with the warm water, then I ran the hose up my ass and injected the liquid deep into my bowels, I knew I could take at least two fills ...
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