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Exploring Anal Play Toys, Anal Play & Anal Sex

Anal Play and Penetration

There are two things I know about anal sex. The first is that most people seem to have a huge fascination with it. The second thing is that anybody who receives anal sex or anal play in general, should be careful regarding how the act is carried out, and follow necessary precautions or advice to ensure that the delicate cavity is not harmed in anyway.

Young Open Minds

My passage (if you will excuse the pun) into anal play began as a late teenager. I socialised, and indeed became sexualised, within a tight group of mixed gender friends. We were relatively open in our opinions and thoughts about sex and often watched dire porn – that had been released in the 70’s – as a leisure activity.

Because of these videos it appeared to us that everyone was shoving their fingers and tongues (rimming) in each other’s arses. So this is what we did as a matter of course during sexual activity. And we bloody well enjoyed the intensified orgasms we achieved from doing so. It was only later on in life that I realised not all play mates want to be involved in this kind of set up.

However, my first two sexual partners were part of this group of friends so they thought it was conventional practice. Indeed my first boyfriend had a whole list of erotic recreation for us to pursue. One was anal intercourse. As mentioned, I was used to fingers and tongues being inserted in my anus, and returning the favour, but I hadn’t had much experience of the male anatomy. I looked at his cock. Instinctively I knew it wouldn’t fit in my anus without a lot of force and a tub of lubrication. I had no idea how to find out which was the best lube for anal play so I told him an emphatic “no”.

Anal Sex The First Time

My next boyfriend just had a list of 3 things he wanted to do – apart from the usual stuff.
First: come on my face, yes I know, don’t they all…
Second: insert various phallic shaped objects in my cunt, not all at the same time I hasten to add.
Third: yes you got it, anal intercourse. He was a darling, with a cock I could visualise in my arse so he got to do all three.

We were together some years but only shared anal sex 2 or 3 times. Even then I felt this was something that should be done sparingly and in the right way. In those days there was little in the way of advice and related products readily available to make anal a risk free venture. Not only that, aids propaganda was rife.

As Jaques Brel would say, “NEXT!” – But the next guy was so completely cautious that deviating from vanilla  was not on his menu.

NEXT ~ What more men!

Almost as an antithesis, my following sexual partner attempted anal sex soon after the first date. I had to inform him that a build up of trust would be needed for me to actually accept his cock in my arse. He persisted and I finally relented, but only when I knew I could relax with him. Trusting someone physically and the consequent relaxation of the sphincter are both paramount to the enjoyment.

So we come to my Ex. By this time I had a much better understanding of the type of sex I enjoyed, which featured bondage for recreational pleasure rather than intimacy. However, he didn’t have it in him to spank me or tie me up. Having been brought up to believe that a man should never hit a woman – so who could blame him.

We both enjoyed anal and because he demanded frequent penetrative sex we often turned to this. For me the purpose was twofold. I didn’t want to get pregnant, he disliked condoms and I would not use the pill. And as I wasn’t getting the kinky thrills I required from other sexual practices, anal intercourse was deviant and sometimes painful enough for the adrenalin to start flowing.

Do it Right

However, even though I enjoy pain, anal intercourse done correctly should not be overly painful. I should have made sure we used the best lube for anal play and made use of anal play toys as well, to make the penetration laissez-faire instead of a scene from Brokeback Mountain. We should have explored the subject matter more thoroughly.

That was several year ago. Now I am with my man, and because of the experiences with my ex, we have gone back to the start where this type of play is concerned – we want to get it right. Pain – spanking, whipping, bondage – is at the core of our date night romps, so I don’t require it from anything else. I need physical enjoyment from anal penetration, not pain. We’ve acquired some lube and anal play toys one being a butt plug and have been having fun with them. After all, you are never too old to learn…

This post has been updated and was first published when I started blogging in 2017.

#422 Adventure ~ Anal play toys

16 thoughts on “Exploring Anal Play Toys, Anal Play & Anal Sex”

  1. You’re very punny! haha Loved the “My passage”. My boyfriend and I have anal sex pretty often and what’s weird is I love it more than anything else we do!

  2. Really? Rimming was such a big thing? This is one of the things that I can never imagine myself doing

    I find it so interesting that you have been so involved with anal play. You write about it as if it’s like any sort of vanilla penetrative sex – completely normal, and you know, it should be without that taboo.

    It’s also interesting that you keep on wanting to try it again, albeit once you trust the other person enough

    1. anal was made to seem normal when I came to sex in the late 80’s – the old 70’s porn movies and men’s mag literature made it that way.

  3. I’ve never performed anal, but I have been pegged. It’s a rare thing for us, but my Queen likes it occasionally. She doesn’t want Angus inside her anal sphincter though! Would I like to try it sometime? Only if I was certain I wouldn’t hurt the recipient. I get enough pleasure in so many other ways.

  4. I think I’m triggered when it comes to anal sex because of what the ex did to me. Lover wants to give anal and we’ve tried many times, but it’s very painful so he stops because he doesn’t want to hurt me. I think it’s partially psychological and partially because as you mentioned, we’re not doing it correctly.

  5. Anal sex is fascinating and for good reason, it’s something we can all (potentially) enjoy. Loved reading about your adventure. Also is the website new? I may have missed it and not noticed, but it looks good.

  6. We’ve never had penetrative anal sex. We do play with fingers. Her pleasure is best when she’s in the mood (understandable). I like when her fingers wander back there, she’s used a small toy on me one time, but it weirded me out afterwards… Maybe try again sometime because it did feel good… She is not interested in being penetrated and I’m okay with that, we do so much else I can’t really complain. Though I would like to try it once in my life. As I’ve said before, never say never when it comes to our marriage thus far. Great Post!

    1. That is a great way to be – the never say never (but don’t forget lube) and – i liked it – but it wouldn’t bother me if i didn’t do it again – so many other great ways to have sexy fun. TY for reading 😉

  7. I love this post, May! You made me smile with some of your remarks along the way. Anal is indeed something that should be pleasurable, and not overly painful. Reading this now has me thinking of anal stimulation 😉
    ~ Marie xox

  8. I enjoyed hearing about your experiences. I have to say anal play can be truly amazing which in my past would of not believed that to be true. But once I experienced anal pleasure I have wanted to find others to share how incredibly amazing it can be.

  9. I’ve got a butt plug. i started of with a small one and could hardly feel it when i relaxed so i got a bigger one and really like it. I liked your post about it.

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