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An Adventure In Masturbation: First Time with Anal Penetration

Posted by: Age: 16 then Posted on: 4 comments
4 likes 17 views Category: Masturbation Male Solo Tags: Male Solo, Masturbation Male Solo, anal, masturbation, first time

First hand account of masturbating while using a toy to stimulate my ass.


One night when I in my late teens, I was reading masturbation stories that people on masturbation sites. At this time, I wasn't smart enough to find free porn and with these sites I could stroke it to the stories and the pictures of the different techniques. So these stories and pics served me well. 

I started the night as normal, get hard and stroke myself while I read the stories. But what stood out this night in the stories I was reading involved using different objects to masturbate with. Some used fruit, others used sex toys, etc. The ones that really caught my attention were the ones about prostate massaging. Fingers, a friend's/significant others fingers, dildos, butt plugs, flashlights and tools. I was like "Isn't that kinda gay?". Well my curiosity got the better of me and I went to a reference on the site. I began reading all about how one would stimulate their prostate. So stimulating it will produce stronger orgasms? Hmm, let me try this out. 

So now I was going to try this out but how? First things first, I cleaned "up"as suggested. Now what to use? My fingers? hmm naaahhh, that would be more clean up. Well I didn't have any sex toy so that option was out. Then I saw it. I had a small cheap plastic flashlight. Perfect! It's handle was about 5 inches long and the head of it would make a great "flared bottom" so it would get sucked up into my ass. Also it was broken inside anyway so I could toss it afterward if I wanted too. So what is next? Lube. So I ran to the bathroom and took the liquid hand soap back to my room. I was all set. 

I locked my door and then I went to my pc. I went to a special booked marked page that had an animated gif of a cock getting hard and below it a woman rubbing her clit. It was a large uncut cock that started limp then built it's way up to fully erect and then dribble some pre-cum, squirted then start over again. The pussy was of a young white woman and nicely trimmed. This was the mid-90's so trim just got popular but still years from my favorite type of pussy, completely shaved. I turn the monitor to face by bed. I then slide down my briefs and kicked them to the side, took my shirt off, got on my bed and laid on my back facing the monitor. For me, being completely nude really makes masturbation a lot more fun and sexy hahaha. I then lifted my legs up in the air and spread them far enough I could feel the air on my asshole. I was already hard from just thinking about doing this, but now I finally started to stroke for bit. Now for the moment of truth. 

As I stroked to the erecting cock and clit being rubbed on my computer, I put some hand soap on my asshole. I rubbed it around a bit to make sure it covered the opening as the instructions said. I stopped stroking and put some soap on the flashlight handle. I lubed it up really well. I then continued to stroke my cock slowly. My heart was racing. Was I really going to sticking something in my ass? Fuck it! Lets get this done. So with my left hand holding the flashlight, I slowly put the end of the handle on my asshole. Here I go. 

I stop stroking and used my left hand now to help keep my butt checks apart. Using my right hand, I pushed the flashlight in. It slowly and surprisingly easily slided right in. OUCH! The pain didn't come from the flashlight in my ass but from the soap burning it hahaha. From the moment I slide the flashlight in, my cock became rock hard and even a bit bigger then normal. I didn't even touch it and it shot up like a rocket on that first 
initial slide in. My cock felt extremely hot like it had a fever. I switched hands, my left was controlling the flashlight now, controlling the speed, rhythm and how deep it goes. The right now was stroking my hard lubed cock. The more I used the flashlight and stroked my cock, the better it all felt. I'd change up speed of penetration and how deep in my ass it went. Soon I started to arch my back as I kept the rhythm up. Next thing I knew I am moaning like a porn star faking an orgasm. These were not manly moans either, very woman like, and I didn't care. I was in a state of ecstasy and bliss. 

I continued to slide the flashlight in and out of my ass while I stroked my cock. Besides the slight burning now from my soap lube, it felt really good. So I started a fast then slow then fast again rhythm while I continued to stroke my cock slowly. My heart was pounding and I was breathing rapidly. I felt dizzy from the excitement. I continued to move the flashlight in and out of my ass but this time I added a bit of a wiggle to it, so it stretch my asshole a bit. FUCK! This feels so good. 

As I used the flashlight faster and started to stroke my cock faster, my asshole would started to tense up in a good way. These tensing up moments would suck in the flashlight into my ass with out having to push it in. The fear of getting the flashlight stuck in my ass increased as so did my excitement. The danger of that happening made my excitement even greater. I then spit on my hand and lubed up my hard cock and continued to stroke it. I was in heaven. 

During this whole time I keep my eyes on the erecting cock and clit rubbing on my pc. As I continued to stroke and slide, I watch the cock get hard on my screen. I imagined that it was my cock, so large and proud as I stroked myself. I then imagined that this large cock of mine will enter that pussy below and I will make that woman cum. I would also imagine that I would rub my cock against the big one, to feel it's warmth then I would go down on the pussy and lick the clit to no end. 

The arching, moaning and tensing up started to happen faster and faster as these image in my mind played out. I slowed down for a bit but it didn't last long as this felt so good. Then I started to get that special tingle you get right before you're about to cum and I started to close my eyes. I tired to hold back but I opened my eye for a second to see the cock on my screen dribble then shot his cum. TOO LATE! 

Like a rocket, I blasted my load. The first shot flew right over my head. The second landed on my cheek and a third on my shoulder. The rest landed on my belly. With each shot, the flashlight slide out of my ass more making the sensation even stronger until I was done cumming. I laid on my bed drained and in ecstasy. I rub my cock some more for the last feel good strokes as it slowly went back to normal. 

I would continue lay on my bed, nude and rubbing my now soft cock and lightly touching my body with the other hand. I felt very erotic and sexy with that orgasm and I wanted to bask in it's glow for a while longer. About 12 minutes later, I took the flashlight out of my ass. Thank god it didn't get stuck up there hahaha. I took a sock and wiped myself down. I put my clothes back and went to the bathroom. I put the soap back and washed off the flashlight. The stories on the sites were true, it really did feel so much better. Looking back, I never had an orgasm with that body shaking intensity or have my dick get harder and bigger like it did then until the first time having sex. Only during sex, penetrative or oral, do i get that same feeling again. Once in a rare while, I will lube up a finger and do the same. I never used the flashlight again. 

That's it. That is just one of my personal adventures in masturbation. What do you think? I have a few more but I will post them at a later date.



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