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My true story of exploring anal masturbation.
This IS a true story.

Ever since I was nine I have had bi-curious thoughts. I used to go over to my friends house and we would experiment. I enjoyed it a lot. But sooner or later, as I knew would happen he grew out of it, and for a while I thought I had too. But then they started up again when I was sixteen. I always loved tits and pussy, and always will. But there was something else I was longing for. Something long! I loved masturbating to threesomes with two really big dicks doing a barely legal woman, I just loved the way dicks looked. I really wanted to suck one too, I tried to subtly hint to my friend one night that I wanted his cock in my mouth. But it never worked.

Right after watching Road Trip, after the scene where the nurse hit’s the guys prostate, I knew I had to try it. So I went my sister’s room. I knew she had a vibrator, it was the perfect size, about as long as my cock, not as thick though, but that was okay because I knew my virgin asshole wasn’t ready for something as thick as a real cock. I got a hard on just thinking about finally having the courage to stick that beautiful stick up my ass. My cock was so hard, it formed a nice little teepee in my shorts.

I had the perfect opportunity to experiment, my brother was out with his girlfriend. My sister was out with her friends, and my mom was fast asleep. So I slip into my room. I throw on my favorite threesome porno. And lie down. I stroke my cock until I cum. It felt so good to just let loose for the night. Then I started to massage my asshole, I had read online that I had to prepare my ass for a vibrator and massaging was a good way to do that. So I did, I rubbed for a little.

It tickled a lot, and I loved it. I stuck my fingers in my mouth and sucked on them. Left a bit of saliva on them so I could my ass nice and moist like a pussy. I was so happy to be able to say I was “wet”. I then stuck my finger in my ass, this was to see how much I could take, it hurt a little at first but I couldn’t stop I loved it. I knew it was time to get down and dirty, so I grabbed the pink vibrator.

I put the bright pink vibrator in my mouth, sucking it, imagining it was my cock. The thought of sucking my own cock was so hot, something every guy wanted to do. This way it also had a little bit of natural lubrication on it. I started to tickle my asshole with the tip of a vibrator. It made my cock hard again within seconds! Then I got ready, I put myself on all fours and started slowly inserting the vibrator in my ass. It hurt so much, but also felt so good. The pain, I think, is what made it feel so good. After it was in there a bit I got used to the feeling and was ready to pump. I started slow and gradually increased the speed and depth. Then I turned on the vibrating function and nearly screamed!

While I fucked my ass with the vibrator I was also jacking off my cock. I would usually think of this hot girl I knew, I would think about her nice tits, and her perfect shaved pussy, but since I wasn’t just jacking off, and since I was fucking my ass I had to think of something a little more gay.

I thought of my brother. He is an ex-marine, and a really muscular, sexy man. I could only imagine how big his cock was, and how nice it must be to be able to suck and fuck it. I could only imagine because he was the last person in the world that would do anything homosexual or even bi-sexual. But that was what turned me on so much, that’s what made me want his cock so badly. So I imagined.

And trust me, imagine I did.

I imagined so much that I thought it was him fucking me, I was in a true state of ecstasy. Then I came, I came all over my hand, and since this was my first truly bi-curious experience I didn’t clean up like I usually did. Instead of just grabbing a towel and washing my hands I tried my cum.


It tasted so good, warm and salty, yet also sweet. I then took the vibrator out off my sweet now stretched asshole. I also had to clean that little pink toy so my sister didn’t know I used it. So I went to the bathroom and grabbed a wet towel, and cleaned it. Went back to my sisters room and put the toy back in her drawer. As I was putting it in the drawer I saw all her bras. Her panties were also in this drawer, all kinds too. Cotton panties, thongs, G-Strings, it made me so horny just thinking of my sister in these. I even grabbed some to put on later.

But that’s another story.
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