Anal

I tried anal for the first time over 10 years ago. The guy I was dating at the time, really wanted to do it. He told me he knew how to make it feel good for both of us. He was full of shit. He was also a pathological liar, which I realized later and broke up with him for, but that’s a different story. 

Anyways, since I wanted to make him happy, even though I wasn’t sure how I felt about the whole thing, I agreed to it. He had me lie on my side. There was no prep really and there were no weeks of training my ass. He wasn’t even that hard when he went to push in and while I think he lubed up a little, it certainly wasn’t enough. 

It didn’t hurt, but it wasn’t pleasant. It just felt awkward and uncomfortable for me. I have since learned he did EVERYTHING wrong. I shouldn’t have been lying on my side, I should’ve been ass up. He should’ve been hard as a rock, so it would make it easier on me when he was sliding in. He should’ve lubed up A LOT. And at a minimum, there should’ve been size prep in that moment – finger to multiple fingers to a dildo and then his cock.

Fast forward to a couple of months ago. One of my Fet friends & I are discussing anal and he tells me I should give it another try, suggesting I buy an anal training kit and use that first. I take his suggestion and get the kit. I open it and am scared to death of the large plug. I still am. Haha! The medium plug is at least sane to think about. But I start out with the small plug. It feels awkward to me. I don’t really know how I feel about it, and I’m back to worrying that I will never like anal.

A week or so later same friend comes over. He tells me he wants me to use the medium plug, so I hand him the plug and the lube. He fucks my ass with the plug for awhile, and I’m in shock at how good it feels and that it is actually turning me on! He fingers me for a long time, occasionally bumping the plug, and I’m in heaven. I will never forget the experience because he actually showed me anal could feel amazing. I owe him many thanks for that one. (I’m sure some future guys do as well. Ha!)

My next endeavor was putting the plug in myself. I used the friend’s method of fucking myself with it for awhile first and then getting it in. Then I got brave and pulled out a couple of toys and used them on my pussy, while the plug was in. It was incredible. I could feel the head of the dildo sliding passed the plug. You’d think it would be an awkward feeling, but it wasn’t at all. 

And now, I really, REALLY want to try DP with two guys. I mean, I wanted an MMF threesome anyways, but now it could perhaps be even more fun. 

I suppose I should at least try anal without toys first though. I’ll get there. But at least I no longer have a fear of anal and know it can feel amazing!