• Tue, Sep 24 - 12:00 pm ET

10 Totally Effed Up Thoughts I Had Trying It In The Butt

augustus gloopI come across as more sexually adventurous than I really am, but much to my chagrin, my sexual proclivities lean to the prudish side. Considering my youth (a few weeks away from my 24th birthday,) I suppose I have years and years to learn how to get freaky, but as of now, I keep it vanilla. Not that I haven’t tried doing cool sex stuff–in fact, I’ve been trying to try it in the butt for ages.

Every attempt at anal sex has ended up with me yelping in fear and scuttling away before contact has even been made between the dude’s P (penis) and by BH(butt-hole), until very recently. Since I’m already bringing shame upon anyone who has ever known me by discussing my pathetic sex life so candidly, it’s worth mentioning that I have had my butt licked and I’ve liked it a lot every time, except for that time when my then-boyfriend started getting handsy with it and put his fingers in there before I could crawl to the edge of the bed and crumple into a crying heap. It’s like anything outside of the butt is beyond cool, but once they start tunneling, I’m out.

My fear of butt stuff has been majorly disappointing (to me, not to most of my sexual partners who have been very understanding and cool about consent and boundaries and stuff). It’s just that I want to be the kind of person that does anal. I know it’s not gross or anything–it’s how a lot of people have sex, even if they have a vagina in the mix. I’ve done extensive research on the subject and have discussed it exhaustively with friends who enjoy that form of intercourse, but I just can’t make it work.

The first time I tried butt sex was horrible. The asshole who tried pressuring me into it didn’t have lubricant, but assured me that saliva would do the trick. It didn’t and I left his house immediately. I haven’t spoken to him since and I never will again because that’s an awful trick to play on someone who tells you they are terrified of being penetrated anally. I went to my best friend’s house after to watch movies and drink wine which cured my hurt feelings, but not my lightly bleeding sphincter.

Most recently, when I tried exploring the old poop chute (effing disgusting euphemism), I got farther than I ever have. He actually got part of his penis up in there before I recoiled, but I did recoil and did not end up having anal sex. But I got close, which I guess counts for something.

Here are 10 Effed up thoughts I had trying to do it in the butt:

  1. I trust this idiot not to hurt me, so this is totally worth a try.
  2. Where does one even find such large bottles of lubricant?
  3. The lube between my cheeks makes it feel like I had an accident.
  4. Oh man, accidents–should I have given myself an enema or something?
  5. At best, I don’t poop or bleed. Do not like those odds.
  6. He’s warming my butt up with a finger and I guess I don’t really mind.
  7. Thank goodness I had that wine earlier.
  8. There is a penis poking at my butt.
  9. THERE IS A PENIS MAKING ITS WAY INTO MY BUTT.
  10. Get the fuck out of there dude; this hurts.

And that’s how I failed at anal again. He took the condom off, put a clean one on and we had classic penis-in-vagina sex together. I’m not going to give up on the butt, one day I will try again and like it, damn it.

Image Via Paramount Pictures

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  • Alexis Rhiannon

    This forever.

  • Samantha_Escobar

    That. Fucking. Picture.

  • Emily

    Why do you want to so badly when you don’t like it? You clearly think of yourself as prudish and don’t want to, but knowing and owning your pleasures (or lack thereof) is the opposite of prudish. You tried it, you didn’t like it, go back to enjoying sex the way you like it best. Stop saying you failed at sex, because you can’t.

    • Joanna Rafael

      I don’t know if I like it or not yet because I’m having trouble giving it a real chance. This is just my experience.

  • re

    There is absolutely nothing wrong with trying anal and NOT liking it. Why are you putting so much pressure on yourself to enjoy it, when you clearly don’t? Anal is not some sex trophy that a select group of people achieve. Sex is all about trying new things and being free to decide if you like them or not (and then never having to try them again)! If you’re with any partner who suggests differently, leave. Do what you want! You didn’t “fail” at anal- you tried it and didn’t enjoy it. Move on to the next new thing.

    • Joanna Rafael

      Or I’ll keep doing what I’m doing@

  • Alyson Melody

    You’ve outdone yourself. So good.

  • anna

    Ok, unsolicited advice, which you may or may not know-
    Don’t do it all at once. it will hurt. go slow.
    Put a tip of penis in, then hold it. stop. wait. Talk about your days, or buffy, or that awesome cheesecake you had. Anything that won’t make him lose his hard on but won’t get him too feisty either
    You will relax, and your “area” will as well, Making it easier.
    Go slow, if it hurts stop again. It should feel more like stretching burn than someone shoved a red hot penis poker up your ass.
    Continue until you can go at it SLOWLY.
    I’d say do that one night then wait for a while, then again, until you feel you can go full speed.
    Then try not to act too bored because really it feels… not unpleasant but not really sexually enjoyable.
    Source: former recoiler in fear/agony/disgust

    Sorry if this was TMI!!

    • Joanna Rafael

      There’s no such thing as TMI with me, Anna. Thank you for this!!

    • gemma_sanji

      “red hot penis poker” is my new favorite phrase

  • Vanessa Vieira

    11. Does poop just fall out of your butt the next time you have to take a shit, or does your hole tighten back up before then?

    • Joanna Rafael

      Good question!

    • redamazon

      The sphincter is an amazing thing. It tightens up in between strokes,
      even during, which is why you have to take it in slow increments at
      first, as discussed above. Unless you are getting fisted by the Jolly
      Green Giant you will never have to fear any kind of incontinence from
      consensual, non-damaging anal play. What you do need to be careful of is
      accidental tearing because of that tightening up. So, when you
      graduate to actual thrusting, make sure he never fully withdraws and has
      to re-enter fully. Also he has to watch the angle so he doesn’t put
      too much pressure on the opening.

    • Joanna Rafael

      Thanks for the info, redamazon.

  • enbrown

    “It’s like anything outside of the butt is beyond cool, but once they start tunneling, I’m out.” Best sentence ever. I want to share it everywhere, but I’m too much of a prude to even tweet about butt sex.

    • Joanna Rafael

      It’s good to hear from you!

  • chicadujour

    You have to have the right partner to do it with, he has to be knowlegable, you just can’t go right into it.There has to be enough anal foreplay so that you actually WANT it! then lay on your side and ease into it, it feels really nice if he plays with your front too, I don’t even need any lube. If you are excited enough you kinda self lube..

  • Psych Student

    If I may, it sounds like you’re trying to jump in too quickly. You need to start by having positive associations with the area. I suggest starting by having your partner use fingers (he can wear a glove if you’re concerned about things) and feel around the area. It’s even better if he can do that while performing oral on you or something. Additionally, putting a vibrator there or inserting a small (though not tiny) butt plug and leaving it there while you masturbate and orgasm will help you feel the pleasure that can be associated with it. I wouldn’t recommend putting in a butt plug and then having vaginal sex – that will probably feel like a bit much to start with. Once you find that you enjoy things being around/in your anus (toys, plugs, fingers, etc.), *then* you can work on the penis. You want to do some foreplay first, perhaps some lubed fingers up there, maybe even an orgasm. Then, slowly put in his penis. Go very slowly, remember to breath, and relax. Just go a little bit at a time, it will probably be a few times before you two can begin a thrusting motion. Just have him get it in and then use a vibrator to orgasm. This will be more association of positive butt action, as it were. You can do it, you just have to be patient. I also recommend books by Tristan Taormino, especially The Ultimate Guide to Anal Sex for Women. Good luck!

    • Joanna Rafael

      Thank you so much for your thorough tips!! Much appreciated.

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