Newbie Ass Play
(I know we've seen him before, but isn't he pretty?)

Attention Anal Newbies

Is he new at receiving ass play? Are you new at giving it?

This article is for you women who want advice on how to start exploring your man's ass (before you don that strap-on and go for the pegging).


  • Brush up on your in-bed communication skills if you need to because the most important part about all of this is to stay in communication with each other.
  • Look at a map of the prostate gland and get a general idea of where it is located.
  • Make sure your fingernails are non-existent. Or push cotton balls into the fingers of a glove with a pen and wear the glove.
  • He needs to be fresh out of the shower. Exterior - Simple soap and rinse of his anal area will leave it clean for play. At this point you need to take into consideration the sensitivities of the couple. If either of you are freaked out about encountering a small amount of fecal matter he can rinse his rectal canal with this while in the shower.  An enema is not necessary. If you are both less sensitive to small messes and are okay with that very occasionally being part of the territory, he can skip the rinse out and just make sure his bowels are empty. Have wipes or towels handy and you are golden!
  • Don't be drunk or significantly altered, be fully present. Limit yourself to one drink if either of you need it to relax.

Getting down to it

  • Remember to have fun and don't rush.
  • Do some foreplay before going straight for his ass. (It's his turn for foreplay!) Kissing, a little bit of a blowjob or handjob so he's hard and excited; in a state where normally he would be ready to fuck you.
  • Then, he needs to lie down and relax. Face down with a pillow underneath his hips is usually most comfortable for him to receive and you to explore.
  • Rimming if you are into it is a great way to start. It feels amazing and is a great precursor to anal exploration. The tongue feels so warm and cozy that you just want to open up your ass and let it in. This is good because that's exactly what needs to happen. So have fun with the rimming if you're down with that.
  • Get out the lube and apply liberally.
  • This next part use gloves if you have fingernails or if you just prefer them for anal play.
  • Play with his ass with one finger pushing in just a little ways and then back out, slowly. Do that for a while. Sometimes he will ask for more. Gradually push your longest finger into his ass all the way. Remember where the prostate is; in this position it is in and down. You should just be able to reach it with your longest finger. You are trying to feel a round firm place about the size of a walnut. It is easier to feel if he is aroused. Stroke it gently, not too hard. The prostate is a gland, so poking it won't feel good. Sometimes it is hard to find so don't worry if you can't locate it right away. The more excited he is the easier it will be to find because it begins to fill with fluid. (Rare, but some women cannot reach the prostate because their fingers are not long enough.)
  • While your finger is inside him you can put your thumb on his taint and push or rub gently there, too. This basically lets you stimulate the prostate from inside and outside.
  • Experiment gently with faster, slower, stroking in different directions, firmer or softer pressure and get his feedback about what he likes best. Try to get really good at exactly what he likes best.
  • If it is comfortable for him, gently and slowly push in another finger. When I say slowly, I mean centimeters at a time. You can use your other hand to play with his balls, rub his ass or his back. Keep it sensual.
  • Instead of continuing to push your fingers in relentlessly, stop when you sense the pressure is too much or he asks you to wait for a bit. Back out and than go back in. Tease his ass; giving him a chance to open up more.
  • If he cannot take another finger, he might want to stop there and continue exploring the next night (or day). This is perfectly okay! More time for anticipation and gradual exploration.
  • If he's had enough ass play - then continue your play in your favorite way. Afterwards talk about how the ass play felt, what you both liked best, if there was anything that you didn't like and ask questions if you have them. Talk about what you want to try next time.

If he wants to keep going

  • You can either use a butt plug or a dildo, whichever you have. No larger in diameter than 1.25", smaller is fine. Make sure the toy is anal safe with a flared base and non-toxic. This is a good one. Hold it in your hand - it's too soon for the harness.
  • Reapply lube. (Do this often with fingers and toys, whenever you even think you need it. Anal penetration feels so much better with a lot of lube.)
  • When you penetrate his anus with the toy, once again go very slowly. Initial penetration technique is important so listen up - Push until you feel that resistance or he says to wait and then stop pushing. Do not back off and do not push forward, just stay there. This is important because when his sphincter opens if you are still pushing forward you can all of a sudden push it abruptly all the way inside him - not fun. Perhaps you've had that happen to you?
  • If you can feel him pushing back to meet you, you know that it's okay to go forward. Or you can always ask him!
  • Do not bottom out hard - this can feel bad in the beginning. Depends on how long your toy is and how much his ass can handle. Don't be in a hurry to push it all the way inside him; his prostate isn't that far in anyway and that's usually where it feels the best.
  • Once in, just hold it there for a bit - 30 - 45 seconds or so. Let him get used to the feel of it.
  • Begin to stroke in and out very slowly.
  • Talk to him - feel okay? Do you like me fucking your ass? Do you want more? Keep it sexy instead of clinical.
  • Remember where the prostate is. Experiment with changing the angle of the toy to see if it will feel better in different positions (this is what men who are good lovers do when they are fucking you).
  • At this point he may want to get up on his knees so that he has more freedom to move and add to the motion.
  • DO NOT WORRY if he is not hard. If you are concerned whether he is having a good time or not - just ask.
  • Talk to him. Keep going? Harder/softer/faster/slower?
  • Ask him if his cock wants attention (if he hasn't already got it in his hand). Many men say yes - some say no because cock stimulation can interfere with the delicious sensations of the prostate.

If he wants cock stimulation

  • Here you can decide to keep going and give him a hand job (if he wants that or wants to do it himself) or have him turn over and lay on his back for a hand job/blowjob. He may be ready to turn over if he's been on his stomach and/or knees a while.

If he stays on his knees

  • You can either kneel on the bed on one side of him so that you can use the dildo and stroke his cock more easily or you can stay behind him and reach around for his cock - whatever works.

If he turns over

  • Your position will be on your knees with your legs spread so that your knees are on the outside of his hips and under his bent knees. This position will give you a balance point so that you can use the dildo with one hand and give him a blowjob or hand job with the other. Again - if he wants to stroke his own cock - rock on.

An Orgasm in Not Necessary

  • Just go with whatever feels right for him. Some men cannot get hard or orgasm when something is in their ass. Some men get rock hard the moment anything is in their ass. Don't make orgasm the goal, have it be about the pleasure of the exploration, the fun of trying something new and the amazing sensations you can find along the way.

Here's why I went into so much detail with this topic. Because when you finally strap on, ladies, the learning curve is steep because you were not born with a cock. You don't know how to move, balance, make it do what you want. Takes practice. So if you take the time to explore your man's ass in the manner described above, you will already have a sense of what you are trying to duplicate with your strap-on because you've figured out what he loves with your fingers and holding that dildo in your hand. That is why these steps are so important for pegging newbies!

Sure, you can just go down to the local toy store and get some equipment, come home and dive in and it might turn out okay or it might turn out badly. The thing is, you will both be missing so much potential pleasure. Sexual exploration is not something to be rushed. It is best done relaxed, playfully, curiously, with lots of communication and luxuriating in every moment of new sensation.

©Ruby Ryder

14 Responses

  1. Loved it and we’ve been discussing this topic. I’ve tried only once to finger his prostate and my longest finger was too short, but we’re both willing to try again.
    Used a dildo once, but it was so awkward. The positions you described would probably be much better.

  2. Ruby, thank you for this. After a while of being interested in experiencing more sexual submission and pegging, I recently met someone that I feel comfortable exploring this with. Being raised in a dominant male culture, it was a relief to read your page. It was written in a way that made me feel that it was perfectly okay and not “un-manly” for me to be interested in this. It assuaged the remaining feelings of shame I still have on the topic. My new girlfriend will hopefully find it useful too. What you say makes a lot of sense to me. I think I will hold off on purchasing any toys until we’ve explored the foreplay first. Thanks again.

    1. So glad you found your way past the societal taboos and misconceptions and decided to explore new parts of your sexuality that have been calling to you. I’m especially glad that you found a partner you feel comfortable exploring with. Letting go of the shame can be a powerful experience. I’m here cheering you on!

  3. wow so glad i found your site! 🙂 finally found a man willing to give pegging a try and it’d been a fantasy for so long i hadn’t thought about all the nitty gritty. very helpful thank you so much 🙂

  4. I’ve always wanted to try this with my boyfriend. It seems so intimate and the thought of a man trusting me so much that he’ll submit to me has always been a fantasy of mine. But unfortunately, I never knew how to approach the subject and I wasn’t very well informed. This site has helped me very much, and I’ve finally spoken to my boyfriend about it. We experimented tonight and he loved it! Thank you so much Ruby, this site is a total lifesaver!

  5. (Sorry if the language is too strong)
    As soon as my wife broached the subject of pegging, I went out to find all the info I could, which brought me to your site.
    My wife has fingered my ass twice now, just this week
    I always wanted to try it, but had some issues after receiving a “shocker” from an aggressive lover that ended embarrassingly. I haven’t dome any self-exploration yet, but the feeling of my wife and I exploring my body together is an incredible turn on!! I already want her to fuck me, I’m surprised how eager my ass is for it, it feels horny all day for the last two days! Is there a length of time I need to wait before we can take it to the next level? I want her to fuck me sooo bad…

  6. I’m so glad I found your site! I have learned mostly on my own through the men who’ve wanted it, but I have always been either too nervous or over-eager lol. This is a great “refresher” and reminder to be gentle with the newbie I will be meeting tomorrow….

    I think I’ll be spending a lot of time here! <3

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