Stick it in your ass

About a year ago I had the pleasure of finding my perfect sexual partner. No subject was taboo, no inch unexplored. He stripped away my insecurities and made me delight in the pleasure we could find in each others bodies. Any fantasy the other had was instantly fulfilled, no matter how awkward it might have been with our first attempt, if you could think it we would do it.

... Of course he wanted anal.
I'd had what we refer to as the "8 second anal experience" before. You don't really want to, but think "Okay, if he wants it THAT bad I'll give it a try". It never ends well and he never gets it in before you squirm, jump, yelp, and generally get the Hell out of there. I didn't have much hope for future anal experiences.

Something about Michael though made me want to try. I knew he cared about my pleasure, safety, and happiness and if I was ever going to be able to accomplish it, this was the man. I also figured anal is a skill set not many woman have and I pride my self on being a very good bedroom experience, so this could only be to my advantage to figure out.

The first time we tried he spent hours worshipping my body from head to toe. I wasn't allowed to lift a finger, this was about me. He worked me until I was more pliable than putty. We had purchased a small wand vibrator and it was time to put it into play. Michael and I had invested in a very good silicone based lube which was ok to use with the plastic based vibrator; a choice we made deliberately and with prior planning. I was at the height of pleasure, every nerve ending vibrating with the taunt tension of desired release. He went so slowly and made sure I was adjusting.

I'm not going to lie, it was uncomfortable, but also a tiny bit pleasurable, so I was able to keep pushing that boundary. That first experience was short, minimally invasive, and masterfully planned. It was decided that I would use the wand during masturbation sessions to get used to it. In the case of anal, practice does make perfect. It is such a foreign feeling that you almost automatically tense up, thus making it uncomfortable.

After about two weeks I felt comfortable to step it up.
This was it, the big moment. I was about to have a successful anal sex experience and was brimming with confidence.

Michael is obviously quite a bit bigger than the wand but with the patience to ease in and the forethought to focus on my clitoris at the same time with a vibrator, we were able to accomplish penetration.

Then he moved. Just pulled out the merest of milliliters to begin the actual thrusting and I lost it. I flew forward and up violently, spun around and said, "I can't do this!", and generally panicked. He was mid reassurances when I found out an interesting fact about anal. Once you're stretched out that far, there's no muscle control for awhile. I laughed at one of his lighthearted comments and that's when the air escaped. This was immediately preceded by me falling off the bed, I was so startled. He laughed, I laughed again, more air. By this point tears of hilarity are streaming down my cheeks, which are stained the red of embarrassment, and I'm begging him to stop making me laugh.

Luckily, like I said, I was with the man who it was impossible to have any reservations or insecurities with. He may have teased me, but it was about me being embarrassed rather than what had happened. It was due to his patience and ability to put me to ease that I was able to agree to keep up the experimenting with anal...

Stay tuned to see if I ever actually was able to complete anal sex from beginning to end, and also what happens when the tables are turned.
*names have been changed to protect the not quite innocent