Friday, December 21, 2012

Stick it in HIS ass

When Michael and I first entered into negotiations for anal, I resolutely determined that what goes around comes around. In fact, it was this very instance about turn about being fair play, that saved me many a drawn out begging sessions for anal from other partners.

The second the words were out of my mouth, Michael instantly said "yes"...

Dammit. Now what!? While the merest of seconds ticked by, while I tried to process a rejoineder, it felt like the world paused for eternity. Did I just somehow talk myself into a corner? Yes, yes I had. And that corner had no way out except the path straight to anal.

I had misgivings about anal for me, but I had never even thought about wanting to stick a vibrator in a man's ass. I was scared it would emasculated him in my eyes. The thing I like about men is being a MAN. How could I still view him in the same light if we did this? This perfect match, this incredible lover. This would RUIN it.

Somewhere, under my initial misgivings, laid a naughty, curious little sexual minx who thought "try anything once!" and I knew, Michael was nothing but a virile masculine man. He carried me around like I was a feather and made me beg for release sometimes. Nothing could change that.

While we were still warming me up for the big show, Michael immediately agreed to start our experimenting with his own anal experience. Much like mine, it was a bit awkward and uncomfortable at first. Uncomfortable for Michael (duh, first time taking something in the ass), and uncomfortable/awkward for me because I didn't know what I was doing. I DON'T HAVE A PENIS.

However, I'm a woman, and I do own more than a couple of vibrators. Once we got started it got easier. The best part about Michael and I is that we can communicate during sex. We would rock at team building exercises, that's how good our communication and understanding is in bed. He was able to tell me when to slow down, adjust angle, pressure, intensity so I didn't feel like a fumbling idiot and he didn't feel like a baby-faced new inmate at the county lockup.

After my not-quite-successful first anal attempt, and the subsequent hilarity, we decided it was Michael's turn to attempt a realistic sized vibrator. This was it, the big moment. Michael had assured me he could take it like a champ (read: much better than I did), and much to my shame, he did.
We decided the vibrator would be controlled by him because he would handle it better. While he was reaching behind himself, I was in front in my oh so favorite position, doggy style. I was a bit bummed there would be no hair pulling with his hands occupied, but I knew I'd still get an incredible fuck. Michael never failed to deliver. So while I was in charge and occupied with keeping his rock hard dick sliding in and out of me and bringing me to a heart racing orgasm, Michael was experiencing anal for the first time simultaneously. We both achieved one of the hardest, most consuming orgasms that day. Something about the situation and how much pleasure he got gave me that much more, and according to him: he now loves his prostate.

As we lay there beside each other, panting and glistening with sweat and shivering with the aftershocks of our pleasure, Michal turned to me to say something... it was then that the air escaped... from him. My eyes grew wide and we both started laughing. Cue more air. I was doubled over laughing so hard I could barely hear it when he said, "well dammit, now I know what you're talking about, you really can't control it," as he sat there passing air two or three more times.

It was at that moment that I realized one other side effect of having participated in anal with Michael. He got it. He really did. He knew what I was talking about with the initial muscle threshold you had to get past and the ridiculous sensation of needing to go to the bathroom that is so weird. He understood everything, and although he got more pleasure from it, he still had to overcome those initial awkward, uncomfortable moments too. This understanding, plus the need to show him up, made me redouble my own curiosity and readiness to keep pushing those anal boundaries myself.

Stay tuned to see if I just talk a big game or if I ever actually successfully completed anal in the last part of the trilogy!


  1. Everything about this post is so perfect - the humour, the openness, the sexiness and most of all the love and connection. Just beautiful.

    Merry, merry, cammies...

    1. Thank you! While anal isn't my favorite thing by far sexually, these particular stories are some of my favorite. I never would've thought laughter could make anal easier, but I suppose stranger things happen in the bedroom all the time ;). I'm a very lucky lady indeed to find someone I work that well with in bed.

  2. This is a really sweet post! FYI, my upcoming book, The Ultimate Guide to Prostate Pleasure: Erotic Exploration for Men & Their Partners might be of interest to the two of you.