Monday, will begin yet another trip to Europe for my husband Sylvanus. Anyone who has been reading us long enough, knows that I am very much interested in anal play. I enjoy anal play. My ultimate goal is to be fucked in the ass pleasurably by a cock. The key word being “pleasurably”. Have I been fucked in the ass before? Oh, yes indeed. Did I like it? No, not really. Both cases in my high school years where I was fucked in the ass, were very much rushed and forced events. One guy insisted on fucking me in the ass because I was on my period and he still wanted to have sex with me. Somehow, the thought of fucking my vagina of blood was unbearable compared to the act of fucking me in my shit stained ass. Heh, who knew? Needless to say, this guy never got to fuck me in the ass. His insistent need to ram his cock into me, was met with nothing but pain and my moving away from him.

Sylvanus has fucked me in the ass before. We did it the right way. He took his time and I found it more pleasurable than any experience I had ever had. Eventually, however, I had to regretfully tell him to stop. There was only so much movement I could handle. There was one night in particular that he took some time fucking my ass with one finger and then another. I was really getting into it and was ready to take his cock, however, when he did try to fuck me with his cock, my body said no. I was bummed …at my… bum.

Since Sylvanus is going out of the country for 2 weeks, I think now would be a good time to revisit anal play. Sure, he won’t be here, but my goal is to have my ass ready to fucked by his cock by the time he gets home and I hope to have Kink Academy help me out every step of the way!

Today I started with the basics of understanding the anus. I watched 3 videos. The first was by Sarah Sloane, where she “packs a lot of information in [a] 16 minute long video starting with: reasons to engage in anal play, the mental and physical obstacles that might be problematic and how to overcome them, safety awareness, lubricant suggestions, what makes a good anal toy, along with stroking and stimulation techniques.” The 2nd video was by Megan Andelloux where she “guides you through the special needs of female anal play and how to help the bottom be “eager” [for] attention.” The last video I watched was also by Megan and here she discusses “the ways to play with insertion including; the best way to use anal beads, adding vibrators or dildo’s and how to best prepare the anus for penetration.”

What I learned most from these videos is that I am not alone. I also learned that so far, all the anal play I have been doing in the past to help prepare me towards cock penetration, has been correct. I could relate to many of the things mentioned in the videos. For example, when Megan talked about getting ready to finally penetrate an ass with a cock, it is better if you let the ass move onto the cock instead of pushing the cock into the ass. This helps the person being penetrated to relax and allows them to be in control of what is happening. This also allows them to take things at their pace. The one time that I did enjoy being fucked in the ass was when Sylvanus and I attempted it. He stayed in place and I was the one that moved myself back into his cock. It was both very pleasurable and insanely erotic.

I have learned that having larger items inside my ass is not the problem. That causes me no discomfort. What is actually making anal sex more difficult, is having to hold the anus open. Wearing a plug is quite comfortable for me. Mostly because my anus gets to close around a very thin stem. When my anus is not allowed to close, that’s where things get uncomfortable and/or feel strange. I have also learned on my own (not from a video I have watched thus far) that if you are new to anal sex, it is not recommended that while getting fucked, that your partner pulls all the way out and then back in again with each thrust. This makes it very difficult to relax. It is best to leave the cock inside and thrust while still within the body and not allow it to leave.

I am looking forward to watching many more of the “anal” videos that Kink Academy has to offer for days to come and hopefully, when Sylvanus returns to me after Thanksgiving, I’ll have a success story to write about.