Jul 03


This post is continuing my good stuff week of posts. It discusses matters of my personal sex life so if that is TMI for you please don’t read.

The first time I tried anal sex I was stupid. It was my idea but we were stupid nonetheless. I knew nothing about anal, and all we had was some lotion and a dark room. It was before the age of the internet and there was no way, as an adolescent girl, I was going to ask for advice from my parents. So we tried. Not surprisingly, to everyone who has fucked in the ass before, we failed miserably. I mean there had never been so much as a finger in my ass prior to putting a full cock in there. Ungodly pain. There was no way I was going to try that again…exit only.. you know the deal.

Jump some fifteen years later and now if I don’t get fucked in the ass on a regular basis I start to get crabby. What changed? A little bit of eduction on the matter and a very wet inducing article in Playgirl magazine.

I had been thinking about it. Some friends enjoyed it. I remembered the pain though. I asked around a little. Still too nervous. I read the article about her back door man. Fuck, I want it.

So we tried again. This time we knew what to expect. We bought some KY and and waited till I was ready. Finger play to be sure I enjoyed anal stimulation. Constant communication. I was ready.

At least I thought I was ready.

There was still some pain. Not as much as my first attempts. But yeah it hurt. It also felt curious, like I might be able to get past this pain and continue. Of course we stopped again that time, cleaned up and went back to fucking. The seed was there though. I learned that the more relaxed and confident I was with anal the less it hurt. Yeah, lube was important, but so was the certainty that you were doing the right thing. I had to let go of my inhibitions about poop. I had to let go about inhibitions about sex. I had to let go of my inhibitions about pain.

When I let them go, when I relaxed, anal became a whole new world to me, and I loved it. It brought out the dirty talker in me. I wanted to beg him to cum in my ass. I could feel every contraction in his cock when he did. Beg for it I did. Melted when his words matched mine. His hot breath in my ears as he asked how deep I wanted him to fuck me. Anal became my friend.

And it wasn’t without its ups and downs. Sometimes I would think I was ready when I wasn’t, so once again we would have to clean up and return to other forms of fucking. Sometimes we would try a lube that caused too much sensation and made anal unpleasant after a short while. Clean up and resume fucking again.

Anal takes confidence more than anything (besides lube. can never use too much lube). Anal takes the confidence in saying no, the confidence that your partner won’t hold it against you for not being able to continue what you started. Anal takes confidence that your partner will slow down or stop halfway in your ass so you can work past some initial pain even if it takes a couple minutes of just holding still. Anal requires confidence in yourself, that you are making the choices you want to make in a sex relationship.

Anal takes confidence, but it is a confidence that can be learned.


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  1. 1
    Sasha Pixlee

    Good piece. Anal is where I learned all my communication and consent skills that come in so handy with kink and, well, life really.

  2. 2
    Timid Atheist

    Consent and communication is something they should teach as a part of sex ed. I really think that I would not have ended the miserable, angry person I am in regards to sex if I and my former partners had been taught to communicate properly during sex.

    Also, too many romance books made me think it would just be so easy to know! Of course the man I was in love with would just know what I wanted and how I wanted and he just teach me everything I didn’t know! Please excuse my stupid younger self for ever believing that crap.

    And thank you for this reminder! Not sure I’ll ever even have sex again. But it’s definitely food for thought on my own views of anal.

  3. 3

    Awesome post, Willo, and you know I like the subject!

    Anal not only involves having to conquer feelings that undermine self-confidence (in overcoming the very loud messages from some parts of society that it’s perverted and disgusting, which consequently redound to the reputation of those who do it; it requires a strong self-belief to ignore that) – anal requires a huge amount of trust in your partner, especially so if you’re on the receiving end.

    I’m AMAB and so back when I was in a gay relationship, I really really wanted to be fucked, but it required building up a lot of trust in my boyfriend, and the first few attempts involved the usual amounts of making mistakes and working through them. I was also secretly curious to take the role of giving rather than receiving, but I had my own feelings to work through (mainly feelings of ‘ick’ from the poop factor) before we tried having sex changing places (I’m ‘vice-reversible’ it could be said). We were about six months into our relationship before we swapped. It proved actually to be more enjoyable a lot of times, because I never quite got used to the size of my boyfriend’s cock – the idea you can progressively stretch the anus to greater diameters, like in the Story of O, is nonsense – and at one stage I developed a pile which made receiving anal sex quite uncomfortable for a while.

    So, starting with either fingers or a small butt plug/dildo to begin with (well-lubed, of course), just to initially loosen the sphincter and then relax for a few minutes before thinking about what to with the penis, is not just highly recommended, it’s pretty well mandatory I think. The rectum doesn’t lubricate, so tons of wet stuff is also good, and getting over the idea that it’s not going to be messy. Of course it’s going to be messy! Even so, it requires a lot of communication and patience on the giver’s part to be continually aware of what’s happening: if there is pain, to listen to your partner and be prepared to stop dead where you are, or to fuck very slowly, or even to gently withdraw and try other things. Sometimes I’ve had some initial pain and decided to ignore it and push through it, and after a while it went away; other occasions started fine and quickly became unbearable, usually putting an end to it except for having a mutual wank instead.

    The sense of intimacy is special, but with it comes great responsibility! The receiver can obviously do damage to the anus and inflict pain; clenching the sphincter slightly can provide more stimulation to the giver, do it too much and that’s liable to be painful as well.

    Sadly at present it’s many years since I’ve enjoyed anal because my present partner doesn’t get the appeal, and so PIV is the better option for a variety of reasons (I suspect that if I go through with genital reconstruction surgery – still a maybe – then I will be getting much better acquainted with the old stand-by known as the strap-on).

    Finally, for the benefit of readers who aren’t familiar with the blog called the Pervocracy, I’ll leave you with highly recommended further reading: How to Buttsex Someone Up But Good.

  4. 4

    Is it just me, or did this post get a bit, well, hot in the middle?


    So, yeah… not into anal myself; I kind of get the appeal, but I lean towards OCDishness in regards to poop, so the squick overcomes the horniness for me. That said, if I was with someone that loved it, I’m sure I’d learn to enjoy it. If nothing else, doing it repeatedly would likely lessen the impact of the squick factor.*

    I think you hit the nail on the head about confidence though. Any really good sex, especially kinky sex, requires confidence, I think.

    *And, let’s be honest here, if I’m ever going to have sex with anybody else ever again, I really can’t afford to be fussy about which hole they want me to stick it in.

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