Sitting around with some girlfriends the other night, the topic of "first time you ever.............." came up. It made me remember my first time doing anal with my high school boyfriend Joe.
Joe was cute, and had a pretty big penis. To be exact, 7 and 3/8 inches. We measured the bottom from where the balls and the root meet. And it was FAT! Filled up my kitty quite pleasantly. My parents went out of town this particular weekend, and Joe came over. Well, pretty much stayed over! Joe was my first everything. First kiss, oral, (giving and receiving) first fuck, facial, and as mentioned above, anal.
We were both 17, and I couldn't get enough of him. This weekend we must have done it 20 times. So good. So here is the short story.
After doing it twice that afternoon, we went out for some pizza. I kept playing with his penis under the table. He kept trying to get me to show him my boobs. We barely made it home. We went straight to the bedroom and started to go at each other. My girlfriends had mentioned anal before, and I had seen some pornos showing it, so I was curious. I asked Joe if he wanted to try it. I think he said something like "HELL YEAH!" I got up to get some Vaseline. I specifically remember two things that happened before we did it. My nipples got super hard and long. More than ever before, and my breathing got really fast and shallow. Wierd. We decided the best way to do it would be doggy style. I got my butt in the air, and Joe slathered the Vaseline on my butthole. It was so slippery we had a hard time getting his penis to not slide all over the place! Finally, I held my asscheeks apart as wide as I could, and Joe held on to the base of his penis and pushed. I could feel the head breaking through my butthole, but (butt!) for obvious reasons, my butthole was clenching. He kept pushing, but it wasn't going in. I told him to sit still and let me come back on him. I pushed back, slowly at first, but still no penetration. So I pushed hard. EGAD! WOW! WOWWIE! I felt his head blast through my sphincter and into my ass. I thought my ass was being ripped apart! I made him hold still for a few moments, then told him to push. I was gripping the sheets with my fingers, surprised that I didn't rip them. His hand were on my hips, pulling me towards him while he entered my ass. Every inch of Joe's penis was agonizing. I thought his penis must've been 13 feet long, it took forever to go in me! Then I felt his pubic hair on my butt, and I knew he was all the way in. We sat motionless for almost 30 seconds, (guess), and I could actually fel my butt relax. And suddenly, it felt ok. I told him it was ok to go in and out now. He slowly started to kind of slide his penis in and out of my ass, a little bit at at time. Soon my butt was really relaxed, and I began to enjoy it. I asked Joe to pull out further, to give me all his length when he would go in. I was really likng the feel off his penis against the walls of my ass. I liked the in and out feeling, feeling my ass relax a little when he would pull out, and the way it really gripped him tight when he went in. I lifted myself up on my hands, and he could go even deeper into me. Thats when I really got going. His balls were hanging very low, and I could feel them slapping against my pussy. Suddenly, I caught myself rolling my clitty. I wondered if it were possible to have an orgasm from anal sex. I wanted to try. I rubbed my clitty hard, and asked Joe to pinch my nipples. Wow. There was a huge fire in my ass, the pain was practically never ending, but I loved his penis in my butt. I had never before felt so full. I was really liking anal sex! I was getting close to coming, and was anticipating it, I knew it would be different. But, to no avail. Joe came first. But I loved that too! I could really feel his cum shooting into my butt. A TON of it, too. I can remember hearing him sound as if he was going to cry, and his grip on my hips kinda hurt. I thoroughly enjoyed feeling his cum inside my butt. A nice thick warm glob of goo! I fell forward onto my belly, and he went with me, laying on my back. My butt was a mess. Full of Joe's ejaculate, Vaseline, and Joe's softening penis. I liked the way my butthole was relaxing back to normal while his penis shrunk. When Joe pulled out, his penis made a "plop!" sound. Airtight!
I have since then had many anal orgasms. I like anal, but only once in a while. I have to be in the mood for it.
Thanks for reading this. I hope you enjoyed it.
