"Are you sure you're ready?"
No I wasn't sure! The last time Michael and I had attempted anal sex with me on the receiving end met with disaster. (See the story here). I didn't want to fail or disappoint, and I was so nervous.
I wanted it. I wanted him. I wanted to feel him slide smoothly inside of me. I wanted to be lost in the pleasure of his arms. I wanted to be consumed wholly, and I wanted to have anal sex.
I just wasn't sure I was ready. Sometimes, athletes and actors talk about being nervous. Those jitters that seem to take over the entirety of their being to the lose of anything else. In the midst of these jitters, just when the curtain is about to raise or they take their first step onto the field, the sudden blazing moment of clarity comes and nothing is left to be worried about, no fear or anxiety. This is it, it's time to perform.
That in no way happened to me. Not even a little. I was just a ball of anxiety to the point where (and I had to be told later because I didn't realize it was out loud) I was MUTTERING for Christ's sake; "ok, ok, just relax, relax, relax. Ok, you can do this! Relax!" I'm sure this did nothing but convince Michael of my readiness.
Then, a soft sigh on my neck as he gently kissed the spot behind my ear that instantly sends pleasure through me. A whispered compliment of how beautiful my ass was and how very much he wanted me. I was ready. Still nervous- but ready.
Michael, ever the in-tune lover, slid in like a pro. Smoothing skin here, a moan of pleasure/encouragement, a vibrator to keep my body humming and ready to find release. This was the point we had gotten to last time, I decided, why raise the bar too high? If he got in anything over one stroke I was ahead of the game, I'd take it!
Michael ever so slowly pulled out a couple inches. I didn't move. Steady like a rock I was! I was the champ, I had done it, we could call it a game! With my flagging confidence bolstered, I thought, "well...we've made it this far. Let's see how far we can take this..." Within the first few tentative strokes I decided that I could handle it. Still weird, still a bit uncomfortable, but I could handle this. Kind of.
"Are you ok?"
"Yeah, I can do it, I can do it... But Michael? You're gonna have to hurry up ok? I don't know how long I can do this"
"Ok." Half stroke. "Oh God, you have no idea how easy that's going to be." Michael was true to his word. Hot, passionate, extremely brief, then suddenly, a shudder. A tightening of the grasping of my hips, my name escaping his lips in a part groan part sigh. I instantly perked up.
"Wait... Did you cum? DID YOU DO IT!?!"
"Yes, I came" was the chuckling reply.
Then as quickly as I had maneuvered away the first time we had anal penetration, I flipped around in a flash and did the only thing anyone who has just successfully had anal sex from beginning to end would do...
I high five'd him. That's right. I threw my splayed hand in the air and gave him the heartiest high five I believe I have ever given in my life. The words that accompanied this were a bit jumbled, but they went something along the lines of.
"Oh-my-God-yay! I-knew-we-could-do-it. I AM FUCKING AWESOME!"
I've found at times like these, it's best to maintain an air of worldliness and refinement. The look on Michael's face was priceless. He looked at me, looked at his hand that he's put up immediately in reflex to receive my proffered digits, looked at me again, and in the most deadpan voice inquired, "did you really just high five me?"
I paused for a moment in my victory dance/butt wiggle to assure him that yes, yes I had just high five'd him and he had better prepare himself for more if I so chose to share in the delight of accomplishment with him.
Any other man would've thought I was crazy. Any other man wouldn't have cared enough about me to take his time and do it properly, and he wouldn't have even have gotten that far. This was Michael however and he was all the things I could ask for in a lover. So he chuckled, shook his head again while looking at his hand, then cuddled and kissed me.
It was a great experience and incredibly pleasurable. We have since gone on to continue our anal explorations and it keeps getting better. We don't do it all the time, but neither of us certainly have any objections to it anymore.
I am also happy to report, like the conquering heroine that I am, no air was passed that day. So while Michael got the prize for taking it first, I got the one for controlling it after.
(Interested in what I did to him previously? check out stick-it-in-his-ass