I Want To LOVE Anal Sex, But It Just Doesn't Get Any Easier

I seem to be f*cked. But not in the ass.

I Want To LOVE Anal Sex, But It Just Doesn't Get Any Easier weheartit

I want it in the butt.

Or, more accurately, I want to want it in the butt.

Anal sex has always been a huge obsession of mine. My porn of choice has almost always been anal, I’ve written a ton of gay male slash fiction centered on anal sex, and I’m a huge fan of pegging.

Anal is something that has fascinated and excited me ever since I knew it was a thing.

Problem is, I don’t enjoy receiving it.

Like most people, my introduction to anal wasn’t ideal.


When my first boyfriend suggested it, I didn’t know of any reason to say no. It seemed like an odd request, but since he was way older, my teenaged self figured he knew what he was doing. He didn’t know what he was doing, and a bit of vegetable oil did not prevent the searing pain that ended that first attempt as quickly as it started.

I tried again many years later with my husband, Flick, and though we knew about using proper amounts of lube, we still knew almost nothing about "warming up" thoroughly and taking it incredibly slow.

Although I would occasionally consent to it, even suggest it when its deviant allure was calling to me, I didn’t ever actually enjoy the physical sensations involved, and would pretty much just endure it.


The memory of drunken, cruise ship balcony anal in the Caribbean is still a good one, despite the well-remembered ass pain the next day.

I love tongues and fingers in and around my ass. Such a huge fan of both of those things and I can firmly add them to my "Hell, yes!" column.

Where I run into trouble is when I try to go beyond those, and I always want to go beyond those.

It’s sexy! It’s hot! It’s what the cool chicks do!

We’re going to return to that last thought in a bit, since it is pretty much the crux of my problem.

Now that I’m a sensible woman in my 40's and not a clueless teen or twenty-something, I’ve read the books on anal, listened to the podcasts, attended the seminars, and know that the key to pleasure is going slow.


With those tips in mind, I have enjoyed reasonably sized plugs in my ass on a somewhat regular basis. I’ve had a lot of solo fun with decently large dildos, DP’d myself, and with enough preparation, I’ve even had really pleasurable anal sex with Flick.

My first anal creampie (a huge porn turn-on for me) felt like an incredible victory. And when my girlfriend, Iris, and Flick DP'd me, I had a geyser of a squirting cry-gasm that felt like it would never end.

Trouble is, it takes so damn long to get there. I’m talking two hours to get me there. And the necessary preparation isn’t decreasing through repetition.

That connected time felt really awesome and hot, so Flick and I made a point of having an anal night.


It was really intimate and I loved being at the center of his attention as he warmed me up and we progressed from tongue to finger to fingers to small dildos to his penis.

As long as we waited at each step for my body to get over the nerves freaking out, sending really strong, panic-inducing sensations of numbness down my leg, I could progress to the next level, and eventually get a lot of pleasure from him doing my ass.

I was doing it! In the butt!

Unfortunately, every time we revisit, we have to start over from scratch.

I would expect the freaking-out nerves to desensitize to stimulation with repetition, but with each experience they react like they’ve never been touched before. My leg goes numb, and I panic and can’t imagine how it could ever feel good, unless I wait and breathe through a two-hour process and we eventually get to it feeling great.


I want to jump to great, or at least feel like great is achievable in noticeably decreasing increments.

I simply do not have time in my week, or my regular sex life, to include this kind of preparation when there are so many things that feel great immediately. I get burned out on repeatedly answering that, yes, I want to keep going despite the scrunchy look on my face, because I know it will subside with time.

With a LOT of time.

But unless I do it regularly, there’s never going to be any chance for it to improve.

I seem to be f*cked. But not in the ass.

I eventually get impatient and start rushing it, and then it doesn’t feel good and the experience doesn’t work for anyone ... and I’m back to the feeling like a failure.


If I’d never experienced real pleasure from anal sex it would be so much easier to write it off, put it in the "not for me" column, and move along.

But the ecstatic moments I’ve experienced when I’ve put the right amount of time into preparation are enough to make this lab rat keep smacking the shock bar, desperately hoping for the pleasure burst, when normally-pragmatic-me would have given up long ago.

Anal pleasure seems to come so easily to women I know and those out there in the world.

I’m always reading blogs and listening to podcasts, and it’s all about the awesome anal G-spot orgasms, the DPs, the global entries. It’s effortless for most women, it appears, and I feel so much shame that it isn’t the same for me.


The messages couldn’t be any clearer: Cool, adventurous, GGG, sex-positive chicks love anal.

My stomach clenches with shame thinking about it.

I feel disqualified from being able to claim any of those descriptors due to my inability to take it up the ass.

I know intellectually that that is ridiculous. I am all those things, and it has nothing to do with how many access ports I have available.

I would never feel shame about not being able to reach the Z-key and delete-key on my keyboard due to my small hands, but the inability to easily accommodate a penis in my ass feels like a character flaw.

The secondary problem is that every guy I date or hook up with wants anal.


And not all of them have been gracious about the "Hard No" I give them from the beginning.

I set my boundaries and don’t budge on them, but I’ve had some pretty unpleasant experiences with the reactions and the "teasing" I’ve received from men I’ve barred from my ass, and it feels awful to feel so devalued for providing only my outstanding mouth and vagina for their pleasure.

This is not just an inconsiderate-douche-canoe-not-worth-your-time problem. Otherwise, decent guys react this way too. I consider myself incredibly lucky to that it stops with a disappointed "Damn!" when they ask and I say no.


Despite my frustration with being considered a terrible disappointment sexually, I don’t actually want to love anal sex for the sake of the men who want it. I’d be so happy to have it feel good so I could love it for me, share it with a special person or two, and continue have it be a "Hard No" for casual partners.

It’s delicate tissue down there, and not somewhere I want any old rando' poking around.

But I want to get to make that choice, not have my over-reactive secondary sphincter make the choice for me.

I realize there’s no magic fix and that all I can do is be patient and go slowly.

Patience is a virtue, but if you know me at all, you’ll know I ain’t virtuous.


If anyone has any suggestions of what has worked for them, I’d love to hear them.

For now, I’ll be in bed with a lot of lube, some nitrile gloves, and a series of progressively larger plugs and dildos.

[Cue theme music from Rocky]

Listen now: There are few acts in the pantheon of sexuality that carry with them so much intrigue, coveting, and fear, as double penetration, and its more advanced siblings double vaginal and double anal. For one thing, these really can’t be done in a monogamous relationship. Oh sure, we can use dildos and such things, but that’s not really where the intrigue lies, does it? On this episode of Life On The Swingset: The Podcast, we discuss double penetration or “DP” in its many forms and talk other varsity level sexual moves.