Sexual Relationships
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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.

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Most Helpful Girl

  • 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 :)

    • 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.

    • Well, as long as it works for the girl, it doesn't really matter how you do it :)

    • very true!

    • Show All

Most Helpful Guy

  • This is excellent advice. Thanks for sharing!

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

    • How many of you prefer anal sex to vaginal sex. Ladies is it better than Vag sex? and men?

    • @Badballie I prefer anal sex, esp to finish.

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What Girls & Guys Said

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  • 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!

    • And how'd it go?

    • If he tears your sphincter muscle it will need surgery to repair it. Otherwise, you are going to seep shit out your anus forever. you may have to use tampons in you anus eventually forever.

  • Thank you so much for sharing this information

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

    • I haven't done it yet, but I did talk to my boyfriend about it.

    • How'd he react?

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  • " 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.

    • Speak for yourself and someplace else besides MY Take.

    • Anuses are not built for sex. It's not opinion, it's fact. And if anyone should be having something shoved up their asses it's males. The prostate is the male g-spot. I wonder why more men aren't open to that?

    • It's only a fact in your closed mind. Yes, prostate massage is absolutely fabulous but so is anal sex done right.

    • Show All

  • Extremely helpful! Thanks for this!

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

    • I will tonight haha

    • I'll look forward to your report in the morning. :D

    • Show All

  • All of this is excellent advice!

    • Thank you.

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

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

    • U r the expert.. lol

    • If heat is what you want, a trip over my knee and the accompanying bare bottom spanking would heat things up substantially, don't you think?

    • Show All

  • Helpful article. Thanks for sharing this.

    • My pleasure.

  • thank you for this take! smiling

  • Thanks, this is what I have been looking for.

    • Glad I could help. I have several other My Takes that may or may not be helpful.

  • It worked perfectly:) thanks

    • 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?

    • It always felt good but I tried it tho easy and OMG... and yea:)

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

    • Show All

  • I think it's the way I finger my girlfriend, but her asshole is wet enough we don't need lube. I do make sure 3-4 fingers can fit easily beforehand though

    • Two is sufficient. Are you kinky, individually or as a couple?

    • I guess as a couple. We were virgins before January.

    • Does she enjoy erotic pain?

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  • Bravo! Well-said! You're explanation is simple and clear! 5 out of 5 stars!

  • 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.

    • 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.

    • 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.

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

  • 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.

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

    • 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.

  • 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 ^^

    • 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.

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

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

  • 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!

    • 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.

    • okay :) Thank you!

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