I noticed some questions on anal sex on free dating sites, and as a later cummer to it, and one who had a very strong, “my ass is an exit only” view for a long time, well, I figured I’d share what changed that.
I think of myself as fairly open minded, and I gave anal a try, well, several tries early in my adult sex dating life.
The first time was at 18, and I have written a couple posts about that night, most recently, “The 3-Some,” and it was also the night that I responded sexually to pain, and I wrote an earlier post on that as well. That was a night of expanding and exploring my sexual limits, and that night he didn’t ask, he just went for my ass and it made me scream with pain, not pleasure and that was that for anal that night.
I tried a couple times with my next b/f, but he was practically a virgin and neither of knew how to make it work, so again with the pain and after a couple painful tries, I wasn’t interested in trying again.
Then about 4 years later, I tried again with a new b/f and he wasn’t that thick and it still hurt like hell, and he made a comment that my ass was so tight it was hurting him. So, that was that for many years and I was unwilling to try again, an absolute mind set against it, and I really believed I’d given it a fair shot.
What made me change my mind was reading an article on online sex dating which talked about this problem, and even went as far as to warn guys to not make the mistake of hurting your partner because you might never get another chance, but he talked about how to introduce anal sex properly.
It had never occurred to me that there was a right way to introduce anal sex dating.
For me, once I was determined to make it work, it took trying over 3 different days to be successful, and a couple more times after that before I started asking for it, wanting it and getting turned on thinking about it. The article wisely said it might take a few tries to be successful and if I’d only given it one try again, I wouldn’t be an anal sex lover right now.
We actually got further the first day then the second because of going too fast the second day. Third try it worked, but it took 15-20 minutes to let me get comfortable before getting going and even though we managed to get it to work, I wasn’t too sure how I felt about it.
Looking back, I’m actually quite disappointed that I didn’t figure it out earlier because it can feel so good.

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