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Comfortable Anal Sex for Beginners: A Guide to the First Time

A very common question in the Sexual Behavior category is how to have anal sex. Men want it and women are terrified of it based on what they hear and read from other women who've had a bad experience. This guide describes a technique I have used successfully with many women to introduce them to anal sex or convince them that despite earlier bad experiences, it can be a fun and rewarding way to connect.

This guide is written from the perspective of the ladies. You need to be in control initially so you're the focus.

Anal sex can be tricky but it just takes a little thought and consideration to make it more fun than you can imagine for both of you. The critical success factor is your control of the initial penetration. I strongly recommend the spoon position. Use a good lube like Astroglide Gel. You don't need a lot of it, just enough to make everything good and slippery. Spoon up in front of him. He has to stay completely still until you tell him he can move. This is critical. Reach back and place him against your anus and press back with firm, constant pressure. Breathe and relax. Don't be in a hurry. You have all the time in the world. Push back internally like you're going to the bathroom. Before long, your sphincter will start to relax and he'll start to slip in. Just keep up the firm, constant pressure. If at any point the pain gets to be too much, just pause right where you are and wait for things to relax. If you need more lube, have him apply a little and you move him out and back to work it in. Once you're fully impaled, pause and focus on how it feels so you can replicate that feeling. Then slide him out and do it again. It'll be much easier the second time. Once you're fully impaled again and are ready, he can take very slow, short strokes to get you used to it. As you acclimate, he can increase the intensity. He'll likely not last long and so be prepared for the spasms of him cumming up your ass. As you get better at it, position won't matter and it'll be similar to vaginal sex except that he'll possibly need to slow down on the initial entry. Since he's into anal sex, he's more than likely a booty man so doggy will be a popular position over time.

Comfortable Anal Sex for Beginners: A Guide to the First Time
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Most Helpful Girl

  • Bellibooo

    Nice article, however I would suggest not starting with a penis right away, rather start with finger (s) and work your way up to a real dick, but that is just my opinion :)

    • AustinMan

      You make a good point. I found over time that if I was completely still and we took our time, they loved taking the big one the way I described. That said, it never hurts to dilate the sphincter first.

    • Show All
    • AustinMan

      The point being that it work for her.

    • sachinHunk

      Good idea rather...

Most Helpful Guy

  • Amagi82

    This is excellent advice. Thanks for sharing!

    • AustinMan

      My pleasure. I've had a lot of fun with it.

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What Girls & Guys Said

141
  • throwit

    " Men want it and women are terrified of it based on what they hear and read from other women who've had a bad experience."
    Actually men and women BOTH fear it because ASSHOLES ARE NOT MEANT FOR SEX.

    • AustinMan

      Speak for yourself and someplace else besides MY Take.

    • Show All
    • throwit

      Fact is fact. Vaginas are made for penetration, assholes are meant for defication. It is not natural otherwise you wouldn't need all this prep and lube and emotional preparedness.
      It may feel good when done absolutely right, but don't confuse that with being "made for sex"

    • jonblane

      If it feels good and both people are enjoying it who are you to say there's anything wrong going on? Have you noticed that some body parts do more than one function? Penis emits urine as well as semen. Mouth takes in food and drink but also sends out words ~ and so on?

      Are you against married gay / bi men putting their penises inside one another's bottoms also?

  • Mariposalover

    Thank you for sharing this piece of advise. It has always been my fantasy to be able to have anal with my fiance but since he is quite large i can never get past his dick head going in. I'll give this a go and share the results!

  • Alej27

    Accurate description but what makes it less painful is the heat of the moment.

    • AustinMan

      That, too makes a difference but patience is, to me, the most critical aspect.

    • Show All
    • Alej27

      Are those your recommendation? Then something to try maybe ;)

    • AustinMan

      I'd make you bring me something to spank you with next time we're together and if it's too wimpy, I'll use my belt on your smart ass to give you a smarting ass.

  • slavehorl969

    It worked perfectly:) thanks

    • AustinMan

      I'm so glad. If my experience holds true, you'll be much more comfortable from now on. From your handle, I take it you're kinky?

    • Show All
    • AustinMan

      If you're into S&M, now he has a way to hurt you, GOOD!! No?

    • biguyct

      mmmm nice

  • Oxxymoron

    Extremely helpful! Thanks for this!

    • AustinMan

      It's my pleasure. Have you tried it this way?

    • Show All
    • Oxxymoron

      I've always been curious. But I just tried it for for the first time after reading this. I am surely a fan

    • Naydyonov

      Why exactly did you like it? (As compared to normal vaginal sex.)

  • Afrajakia

    Helpful article. Thanks for sharing this.

  • lostgirl_searching

    Thank you so much for sharing this information

    • AustinMan

      It's my pleasure. Did you have fun anal sex?

    • Show All
    • He respects me a lot and he even told me it will feel disrespectful to do anal because he knows it's not something I'm really into. I just want to make him happy, so I said I was willing to try. Haha he's a sweet guy but I guess I will have to tell him that it's really okay

    • AustinMan

      I think you need to tell him that what's disrespectful for you sexually is something that you, not he, gets to define. If you want to be butt fucked, his job is to take you up the ass and enjoy doing it. I suggest you tell him that you're a pretty sexual animal and that you're gonna want to try a lot of things over time and that you want him to not judge but to just humor you as you will do with him. A major part of a partner's role is to fulfill the fantasies and curiosities of the other.

  • OlderAndWiser

    All of this is excellent advice!

  • GFEDATY

    thank you for this take! smiling

  • Anonymous

    You are missing so many critical steps in your process and getting a couple things dead wrong.

    This may have worked for you.

    But this is not really thorough, descriptive enough or accurate enough to be considered excellent instructions.

    I give it a 6/10 with bonus points for even trying, it's commendable. But nope.

    If you want to, I can DM you. You and I can work on a bit better set of instructions with a little of an actual woman's POV, and some more anatomical accuracy, and repost is as a new MyTake.

    • AustinMan

      Fire away. I'll be very curious to hear your perspective if my presumption is correct that you've had a LOT of anal sex.

    • Anonymous

      You made no mention of the process of getting ready to have a whole penis in there, like starting with smaller objects until the woman is able to consciously control the second sphincter.

      If people just do what you're describing with no prep work in the weeks, months or years preceding, it will be painful for MOST of the recipients. If your recipient does not know how to control the second sphincter pain is virtually guaranteed.

      And you recommended one of the standard water based lubes, which are not even close to as good for anal play as silicone or oil based, not even close.

      You are very correct about the recipient needing to control the action. But just pushing against the sphincters (of which you only mention ONE) is exactly what causes pain, and it can also damage the muscle. You can't just bully the muscles to open, the recipient actually needs to learn how to OPEN the second sphincter consciously.

    • AustinMan

      Let's take this to messaging until we have a joint My Take to share, if we can, please.

  • Anonymous

    Wow that seems close to how I want to lose my virginity.

    I want to try anal at least once in the future, especially if my man wants to, but I was really worried.

    Does it actually feel pleasant for women? I figured it'd hurt more.

  • Anonymous

    whats the spoon position like if we are "spooning"? cuddling? i'd have to try this

    • AustinMan

      Spooning with your back to his front. This has the advantage of giving you complete control without your body weight in the picture. That allows for a lot more control. It also gives him a great angle for seriously butt fucking you when you're ready.

  • Anonymous

    What about hair in there? is it a problem for guys?
    I heared that it was okay to cum inside but that its not good for the man cuz there r bacteries that live naturally in the anus that can cause him infections on his dick?
    also how many time does it take to speed things up? Thank u ^^

    • AustinMan

      Please message me. You have excellent questions though I'm not sure i understand all of them. I want to distill what we talk about down and put in here as an update.

  • Anonymous

    He always tries to do this in the doggy position and I just can't take it like that not yet with him anyway

    • AustinMan

      So try the spoon position and make him be perfectly still while you back up on it very slowly as your sphincter relaxes.

  • Anonymous

    Thank you for sharing this! I'm 17 and plan on trying Anal in a year or two and have been a little iffy about it. I can finger fuck my ass and it feels great but a dick is so much larger so I have no idea what to expect or how to go about it. Thank you for sharing!

    • AustinMan

      Thank YOU for being the first to comment and for being so positive. I'm delighted to help and if you have any questions, you can attach them here or just message me.

    • Anonymous

      okay :) Thank you!

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