Your honest ANAL experience

[fireman0922]

Anal is subjective. Some like, some don't ......!
Let's see what it has to offer. Share your HONEST ANAL experience, the does, the donnots, the pros and cons, the best and the worse.
Help us understand the concept better by sharing your experiences.

To be honest, I haven't tried it only because I'm scared that it would quickly turn into something ugly and uncomfortable.

I have always fantasized about about anal sex, maybe it's the naughtiness, the taboo.....but always was turned on by the thought of it.
Then in my mid 20s I met a woman who was willing to let me try. It was absolutely amazing watching her asshole stretch around my cock as she lowered herself back onto me. I was hooked immediately!.
After that I always told the women I dated I was interested, some where willing, some were not. I always loved when a woman who had a bad past experience with anal was willing to let me try. It became a challenge to me to change their experience. I loved going slow, taking my time, slowly stretching them until they were ready, it was always a huge victory in my mind when the woman ended up loving anal.
In my 30s I had a girlfriend who was open to the idea but very hesitant. So it took me a while before she left me try. Whenever I'd go down on her I would play with her asshole, just massaging at first, then licking, eventually she started letting me finger her. Over time it became our normal routine every time I'd go down, I'd have one or 2 fingers inside her ass, her ass was definitely ready but her mind wasn't there yet.

One day while she was sucking my cock she looked up at me and asked what my fascination was with anal sex, as she returned to sucking my cock, I was explaining my answer as best I could. She then said, "what if I wanted to finger your ass?" As she asked the question her fingers were already sliding between my ass cheeks and once her finger started massaging my asshole it felt really amazing. My response was "go slow like I have done with you" She reached over to the night stand and poured some oil on her hand and went back to my ass. I spread my legs giving her better access. As a dominant male this was very unnatural and I felt very vulnerable but I stuck with it.
She started to massage my asshole then slip on finger inside slowly, allowing me to relax then she'd go deeper....taking her time.
Once I relaxed enough and she was able to finger my ass she resumed my blow job. She had me cumming in seconds, to this day I have never had more powerful climaxes than from getting fingered and blown at the same time. It's always so fucking intense.
That same night she let me fuck her ass for the very first time. Anal sex became a regular part of our sex life. She said she always liked vaginal sex better, but anal was a very close 2nd.