So you want to put it in my butt?

Sub title: Sex is mess, anal sex is messier.

You can already tell where this post is going, can’t you?

It’s Friday and I’m in need of some relief to get me through my work weekend so I’m going to tell you about my anal sex experience. That’s right, in an ongoing effort to be honest, I’m going to talk about my ass.

If you recall, I had a bit of a bucket list of things to accomplish before 30. I’m not sure I managed to get many of them done before July ended, but a few things are better late than never.

I’ve got a fat ass that garners a lot of attention so I’ve always had a bit of a thing for all things ass. Spanking has been my ass play of choice, but the fascination with anal sex has been there.

A lover or two has taken a lubed digit and swirled it around my rose bud when he’s got me from behind. Some have pushed it in and made me squeal. It’s good and I like it.

Porn and erotica paint this picture of anal sex that’s alluring, sexy, hot. Reality can be that, but as a first timer I can say it’s a lot of other things too.

I am not sexy during the act of sex. I can argue that I’m not sexy most of the time, but some of you will call me a liar.

Unless you’ve had lots of the D in your A, anal sex hurts like a bitch the first time.

I prepped with pretty, jeweled plugs that a few of you were privileged enough to see. I consulted experts in the ways of anal sex and watched a little porn, but nothing can prepare you for the first time someone slides in.

It’s this interesting mix of pain/pleasure that blows your mind. You question how something can feel good and hurt so damn bad. It’s the moment he’s in to the hilt, that is the moment where you know you’d do it again over and over.

But this shit (emphasis on this part) is also hella gross.

I’m not sure what comes out of your ass, but mine holds and expels some nasty stuff. Sticking a dick in will not change that. Actually the stimulation increases the likelihood of a messy occurrence.

(It’s taking everything I have not to be crude, folks. It’s far more difficult than you know to refrain from making shit jokes.)

He seemed to enjoy the sex. He enjoyed it enough that we had sex more than once, but he hightailed it to the bathroom after each go.

So things I’ll need for future anal sex encounters? Lots and lots of lube and an enema pre sex. How often does the topic of an enema come up in a blog? It’s never graced mine!

If you plan on sticking anything up my ass, be prepared. I’m very clean, but some messes can’t be avoided. We are talking about the stink and not the pink here.

I guess it’s a good excuse to shower together after? Because many of you fantasize about that, right? Me, naked and wet. Naughty!

If you ask real nice, maybe I’ll show you my jeweled plug snuggled in between my cheeks. You have to ask nicely though. 😉

Here’s just a little sexy to take the stink out of the post.

He jerks my hips up, pulling me back when I want to sink forward. The shallow thrust of his cock burns so good that I bury my face in the pillow to hold back my groans.

My head’s pulled back, his hand grasping my hair and yanking me up.

“I’m gonna fuck that ass. Tell me you want me to.”

The withdrawal is slow like he’s waiting for my answer before he’ll begin.


I want to beg, but I can’t speak. I want him to use me, disregard my pleasure, take my ass at his speed. I’ve never wanted anything so badly.

And then he’s pushing me to my limit, blending pain and pleasure with the depth that his cock can go to. Whispering “Shut the fuck up” knowing I can’t keep silent, knowing that the restraint makes me pant and thrash and cry out.

Makes me say “thank you” when he’s done.


  1. advizor54

    There are lots of things that get left out in porn and this is certainly one of them. A friend of mine is a devoted anal sex slut and she is all about preparation. “Cleanliness inside and out is the key'” she says, and when her lover is coming over she eats right, bathes often, and starts a routine that makes it all work better. it’s fun, she says, but it pays to be prepared.

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  2. Warm Creme

    Cara, as you know, my pain tolerance has kept us from proceeding fully with this. I am glad you shared this reality about it. What you didn’t emphasize In this was the amount of pleasure that you received in this. It is one thing to let Mr. WC feel this sort of pleasure (in spite of the mess), but if it isn’t pleasurable (meaning that I’ll want it more and more), I don’t know if I will proceed any time soon. I will be awaiting the plug that you endorsed, in the meantime.

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      Cara Thereon

      I liked it, but it hurt. I liked it enough to try it again. I have a feeling the pleasure increases as I get used to it. But I also know a little anal play can be enough. Enjoy the plug!!

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  3. Samara

    I think it’s pretty standard to use an enema to prep beforehand. I’m not an expert, but I do enjoy anal sex. And not to be gross, but I enjoy it more when there’s more room I there for what I want!

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      Cara Thereon

      Hahaha. Don’t worry about being gross here! Maybe I’ll try that. Not something anyone tells you when you’re thinking of trying it. Or maybe I’m just not all that intuitive.

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  4. Hyacinth

    You are too funny! I wish I could get TN to try anal, but he’s much too nervous about his size! It’d probably take me weeks of butt plug work to convince him I’d be ok.

    And to that end, like Advizor said, lots of prep is good. I’ve mentioned this before to people, but I had a roommate years ago who discovered she loved anal and would eat colon-cleansing foods for days before her bf came over (she swore by it!) and my ex lover, Troy, would run and give himself a quick one before any ass work (he used s little handheld bulb squirter thingy and swore by it!).

    Anyway, yes, it’s messy as hell, but I’m convinced dudes are just waaaay cooler than we are about that kinda stuff since they’ve been making stinky messes themselves their entire lives 🙂

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      Cara Thereon

      This is like the one thing no one talks about! I mean, can something this intense be anymore embarrassing? Apparently. Haha.

      I’ll have to be a bit more prepared in the future.

  5. Nick

    You are soo right about lots of lube, especially if it is all new to you. ‘No lube needed’ sounds simply dangerous! And go oh so slowly, too.
    In most cases, a visit to the bathroom a couple of hours before is good enough. Hey, consenting adults and all. No amount of enema will make you totally clean and you have to be careful to get rid of the excess (plain) water you use. Not doing so is a real turn off!
    To reduce the yuk! factor, especially early on, condoms (and lube!) are a great idea to let everybody relax. And remember, the anal wall is much thinner than the vaginal wall, so while you won’t get pregnant the risk of a ‘social disease’ being passed on is higher.

    I’m so glad you had a good time:-)

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  6. Fatal

    As everyone else has said: prep work, eating right, lots of lube, blah blah blah. But part of Anal sex is just accepting sometimes there will be a mess and sometimes there won’t be.

    Totally UNSEXY alert:

    It’s a lot easier if the receiver is “regular” and has a balanced diet. Like anything, water is also really good for you! Not just for the stink, but the pink too (laughing like a child right now!) I drink about 3 litres a day on the regular.

    Sir and I engage in a lot of anal sex and the gross stuff has only happened once or twice. But I’m also super paranoid about it (even though it’s just a fact about anal sex–IT HAPPENS) so I may go overboard on the prep work if there’s even a chance—since he likes to spring it on me I generally make that part of my preparation for him coming over—clean the house, clean the room, clean the butt.



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      Cara Thereon

      I have no idea when I’ll be having regular sex again let alone anal sex. I just wish I had thought about this beforehand. So better diet, more water (something I’m bad about), and lots lube. A partner not so worried about it would be good also

  7. hubman38

    Okay, where to start…
    Yay for your first anal sex experience!
    Boo, it wasn’t me 😉
    Enema beforehand? I’ve had anal sex with, umm, numerous partners, and to the best of my knowledge only one of them used an enema beforehand. Yes, I noticed a difference, there ‘was more room’ as one of your other readers said, and not even a trace of poo. But of all the others, a mess is a pretty infrequent occurrence, with or without any other sort of prep beforehand.
    Even when there’s no trace of a mess, I’m pretty much heading right for the bathroom once we’re done to wash up.
    Anal sex doesn’t have to hurt, even the first time (I’ve been the first once or twice), encourage him to slow down, might take a while to get your ass to fully relax but when it does, unless he’s *really* thick it shouldn’t hurt much at all.
    Lastly, I hope this is the first of many times you get a cock in your ass and that the pleasure only increases!

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      Cara Thereon

      It wasnt an awful mess, but it definitely wasn’t clean. There are a few other factors that added to the mess, but that’s neither here nor there.

      He should’ve a little slower in order for me to adjust. We did talk about this long before it happened, but I don’t that kind of consideration was going to be taken on his part. I know I’ll need far more lube than was used and a lot more personal relaxing as well. Lots of lessons!

      I wasn’t turned off was the biggest part even with the pain. The rest I can figure out

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  8. Dawn D

    Alright, I seem to be commenting a lot here today! Usually happens when I first (re)discover a blog!
    Anal sex has been a fantasy of mine since I was pretty much a teenager. I’ve had fingers up there a few times and a cock there only once or twice. I never did any special preparation (especially since the first time was thrust upon me completely, I never expected it would come to that, having had a spouse who was grossed out even by just the thought of it). There never was a big mess. I was lucky and so ready for anything like this that it wasn’t really painful ever, even that first time when we didn’t have lube on hand. It just became uncomfortable too quickly and I told him so and he stopped.
    It’s much more pleasant with lube. And some added again later on if needed.
    What I read about enemas is that there is actually a risk of infections because the anal lining is so fragile. So it may be better not to use one. I’m wondering about the use of glycerin suppositories, but my experience was that it tries to clean you too much and you end up having to go to the loo too often, which is not what you want at all when trying anal!
    I suppose that any man willing to go the anal route is aware there is a risk of a mess.
    I am pretty sure I’d recommend going to the bathroom to clean up after the act both for him and for you, especially if you want to keep going and revert to vaginal. To prevent that, condoms may be useful as Nick said. Use one for anal, get rid of it for vaginal, and you can switch from one to the other as often as you like (with new condoms, it’s easier to put them on I think!) without having to worry about cleaning up in between.

    And for Mrs WC… the pleasure is intense, at least it is for me. Very much worth trying 🙂
    But you may want to work up to your husband’s girth by using plugs, fingers and so on 🙂
    Any sort of anal play is worth it in my book!

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      Cara Thereon

      I think it would’ve been less painful some pre-stretching (fingers or a plug), but I also enjoyed the pain with the pleasure.

      Okay, maybe it wasn’t as messy as I’m making it seem. There was some clean up required after, but not so overwhelmingly disgusting. I’m actually pretty used to poop.

      I’ll definitely try it again and be a bit more prepared for anything in the future.

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