Pillow Humping

Posted by: Age: 20 Posted on: 0 comments
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Recently, jackinworld.com had a Question of the Week asking if there was anything people wished they had known before they began masturbating to orgasm. At first I couldn't think of anything, since I started masturbating so early in life that I didn't know what I did or didn't know at the time. But then I remembered the terrible guilt and uncertainty I had as a kid about this activity, and realized life would have been a lot more pleasant if I had known that all boys do it (though most don't start as young as I did), and that it is perfectly normal for boys to pleasure themselves.

Like most boys, I discovered very early that playing with my penis felt good. I probably started doing so as soon as I got out of diapers. But my mother didn't like it. When she saw me with my hand in my pants, she'd yank them out and slap my hand, and tell me it was 'dirty' to handle myself like that. So of course I got an aversion to doing that, at least when she was around. Even if she wasn't, the nagging feeling of it being 'dirty' was bothersome, and I felt I was doing something nasty.

Then one night in bed I had my hand in my pants, and it felt really good, but I felt I was being nasty and wanted to stop. But it felt too good to stop. Somehow I got the idea to put my pillow in my crotch between my legs and roll into it, and it felt really good. Since I wasn't handling myself, I figured that wasn't dirty, or at least not as dirty, so I kept doing it, rubbing my hard little penis into the pillow. It felt really nice, and I fell asleep that way.

That became a nightly habit, then one morning I woke up and found the pillow still between my legs, and started to rub on it. I got hard, and it felt good, and this time I didn't fall asleep. I lay there like that for quite some time, enjoying the pleasant feeling in my loins, when I realized it was feeling better and better. Suddenly my whole body tensed up, and waves of the most wonderful feeling radiated from my penis, and it started throbbing and pulsing. I didn't know what was happening, but I was having my first orgasm, and it felt wonderful. I lay there totally stunned by what had happened, catching my breath.

I had to hustle and get dressed for school, so didn't have much time to reflect on what had happened, but all day every time I had time to think I wondered about it, and looked forward to trying that again when I got home. I walked home from the bus stop very fast, and had a very sensitive boner in my pants from thinking about what I was about to do. When I got home, I didn't waste any time running to my room. I had about a half hour before my mother got home from work, so I got right to the task of getting that wonderful feeling again. I pulled my pants down, grabbed my pillow and put it between my legs, and began humping. It felt sooo good, even better than it did in the morning, I guess because I had been looking forward to it all day.

It didn't take long to build to the climax, and I again experienced that feeling, with my penis throbbing and the pleasure radiating out from my groin. I felt good all over. Knowing my mother would be home in any minute, I didn't linger, but pulled my pants back up and went downstairs to where I normally was when she got home. On the way I stopped at the bathroom, and I noticed my face was all red from the exertion, so I slapped some cold water on it so it wouldn't be obvious that I had been up to something.

That night I lay in bed thinking about what I'd discovered. I wondered if what I did would also be considered nasty or dirty. I figured if my mother thought it was dirty to play with myself, it was probably because doing so gave pleasure, and that is what she considered dirty. Since what I did with my pillow felt even better by far, it must be the ultimate dirty thing to do. I had mixed feelings from then on. I felt guilty doing this nasty thing, but I loved it so much I wasn't about to stop, and did it at least once, and sometimes two or three times a day, from then on.

When I finally started to develop semen, things got messy. Not much at first, but over a period of a couple of months I began ejaculating enough that it was starting to really mess up my pillow. So I got an extra pillowcase to put on top of my pillow to catch the mess, and then kept it hidden in my room. I was scared to death my mother would find it, but she never did because I hid it really well.

My guilt still wracked me, until one fateful day when I was 15. For some time I had noticed a quiet buzzing sound coming from my mother's room sometimes when I came home and she was in there with the door closed. Curious, I waited until she wasn't home one day, and sneaked in to see what was causing that noise. It didn't take long to find it in her dresser. It was a long plastic vibrator. Due to its shape, its purpose wasn't hard to figure out. I held it to my crotch and turned it on, and it felt wonderful against my penis. I pressed it hard, and left it there for a couple of minutes, and ejaculated right into my underwear. It felt great, but was truly messy.

I carefully put the vibrator away and went to clean myself up, and got to thinking what this all meant. My mother, who started this whole guilt thing years ago, masturbated also! What a hypocrite. Suddenly all my guilt vaporized. If my mother could do it, I could too. From that day on I masturbated guilt free, and it was wonderful.

I couldn't get the vibrator out of my mind, though. I didn't dare keep using hers out of fear she'd catch me or notice if I didn't get it back in place perfectly. But one day when I was in the garage I spotted the orbital sander, and it struck me that would make a dandy vibrator. I didn't want to hurt myself (or my best friend!), so I got a soft rag to cover it up, and pulled my penis out, turned on the sander, and carefully pressed it to my erection. The result was instantaneous - it felt tremendous, and I felt my orgasm coming very quickly. I realized I should use more cushioning in order to slow it down, but I still had a great orgasm, spitting semen all over the workbench.

Because of all the noise it made, using the sander wasn't very convenient, so I didn't do it often. But it was an occasional special treat.

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