When Jack entered me there was a brief moment of intense pressure, it was not what I would characterize as pain. It is uncomfortable and it leads to a moment of indecision – Do I want to do this? I  continued and I was grateful that Jack was patient enough to go slow through this interval. I think if you are working with learning anal, develop some communication of when your partner needs to slow down and when they can proceed. After that sensation passed, within the first minute, I relax a bit more and everything feels wonderful. No, it is beyond that, it makes me have one continuous orgasm. Last night I added a vibrator up front to the mix and I think I might have blacked out for a bit there. I have to say that a real cock in your ass feels much better than any toy.

I have learned a couple of things beyond the need to work up to the size of the cock you hope to have in your ass. One, it helps to relax if I am already turned on. A fair amount of foreplay or some good old-fashioned cock-in-pussy fucking will go a long way here. Two, I need to be relaxed overall. I think if my legs or arms are under tension, it is going to be difficult to not also be tense everywhere. Tension might lead to a nice tight pussy, but may be detrimental to anal. My pussy gets wetter when I am bound up, my ass won’t. Combining anal with sensual bondage is going to be an exercise involving a great deal more mental discipline than I have now.

So now, three times in, I feel like we are well on our way to a whole new area of sex to explore. I can’t wait to try some new positions!

If she refuses, she’s unwilling to spontaneously lose control with you. Deal with it.

If she locks herself in with her hands cuffed in front of her body, she’s likely to be up for some play, but won’t be ready to completely let go. Be prepared to invest some time building trust to the point where she can really cut loose with you.

If she puts them on with her hands restrained behind her back, congratulations! You’ve found a woman who’s willing to give herself to you unreservedly. Marry her, quick, if you haven’t already.

The secret to happy anal is patience. Take everything slowly. (That, and use insane quantities of lube.) Alex started small, with a well-oiled fingertip placed just inside her anus. Over the last several weeks, she’s worked, moaning and begging, up to the point where she’s ready to try something a little larger.

About a month ago, I presented her with an Njoy “Pure” medium-sized plug. It’s a luxury toy, made from surgical steel about 1.25″ at the widest point, and heavy. Alex went crazy for it, and I’ve slid it into her ass at every opportunity since I brought it home. I’ve even started calling her from the office late in the day and having her put it in for when I return.

I just ordered an anal “training kit,” a set of three cock-shaped plugs in small, medium and fucking large sizes, along with some nice anal lube featuring a mild numbing agent. Alex will be taking the first of these into her snug butt in the next day or two, and has been begging to get through her “training” as soon as possible. I plan to help her celebrate her graduation, personally, sometime very soon. I’ll keep you posted.

More later.