Ride’em Cowboy

A few weeks ago Chaos tried to fist me again. It was marvelous; she’s getting pretty close to being able to fit her whole hand inside me, I told her that I had stretched myself out with Dita (my biggest and most realistic dildo) ahead of time. When she told me that next time, she wanted to watch, my imagination ran wild. I love butt stuff so much, and I’m always eager to get Chaos excited about my butt.

So last Sunday, when she expressed interest fucking me in the ass, I was excited. The downside of buttsex is that it’s hard to be spontaneous about it, so whenever I know there is a possibility that she’s gonna want to pound my ass, I try to prepare in advance. On Sunday, I went and got cleaned out, and then put in a plug, intending to let my asshole relax for a bit. However, Chaos said she wanted to fuck me right then.

I had a vague idea of what I wanted to do. I knew I wanted to put on a good show. I took this long-handled dildo and fitted it between my mattress and box spring and the got on all fours. “Is that something you do?” She asked, as I lined the head up with my asshole . “It’s something I can do.” I said as I pushed back onto the silicone cock.

Once it slipped in, I rocked back and forth, fucking myself on the dildo. I took Dita and started sucking on it. I wanted to show her what a slutty Boy I would be for her. I tried to deepthroat it, but gagged. I was hoping she would climb off the bed so I could give her a blowjob while I fucked my ass against the bed. But, as I put on my smutty act she told me it was so hot that she couldn’t wait anymore, and she wanted to fuck me.

I sort of wanted to put on more of a show but I’m not about to argue with Chaos. She had me bend over the bed. To accommodate our height difference I couldn’t be on my knees or all the way on the bed, so I ended up up on my toes as I bent over the bed. Gently, she pressed the tip of her cock into me. Then she gripped my hips and began to move her cock in and out. God, that woman can fuck.

I moaned and writhed under her as she thrust in and out of my ass.Then, she stopped and pulled out. She went to our toy box and got herself a vibe. “I want to come in your ass,” she said, as she slipped back inside me. Then she slowly, gently, fucked me, driving me absolutely nuts as she focused on getting herself off in my ass. My legs were burning trying to maintain the position, I gripped the sheets and moaned, talked dirty, trying to get her off before this teasing made me lose my mind.

Finally she cried out and collapsed, happily, onto my back. For a moment I thought she was done, but then she pulled out and climbed onto the bed. She laid down on the bed and told me to get on top. This was new, we may have tried it out before, but most of the time Chaos fucks my ass, she’s had me on my back with my legs in the air. On top was different–before then I don’t think I’d ever come while on top for any sexual activities.(Not that I am ever the top, I’m just sometimes on top.)

No one complains about bottoming from the top.

Knees bent, I lowered my ass down onto her cock and it slipped in. I started moving then, bring myself up and down. Riding her cock faster and faster. It was indescribable. Really, the thinking part of my brain stopped working as I bounced up and down on her cock, loving how she filled me up, tickling that special spot. It was so fucking intense, I lost control of my sounds, I was moaning, maybe screaming as I rode her cock while she played with mine. Then it hit. I asked her if I was coming, because it felt like I was had started to, and simultaneously felt like I was right about to. I fucked up and down faster as she told me to come for her.

Oh, and I did, I came so fucking hard, and for so fucking long. It was so intense. It shook me all the way to the core of myself, like I had been fucking my entire nervous system. I shook and nearly cried afterwards. I thanked Chaos profusely for letting me have that. She is so amazing, and she fucks me so, so well.