23. October 2013 · 17 comments · Categories: Blog · Tags: ,


Attention Anal Newbies

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

Here are some suggestions for you women who want to begin to explore your man’s ass before donning that strap-on and going 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 or this (emptied out and refilled with plain water) while in the shower.  An enema is not necessary. If you are both less sensitive to that 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 don’t poke it! (Credit for this line goes to The Ultimate Guide to Prostate Pleasure by Charlie Glickman and Aislinn Emirzian). 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 small toy 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. 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.
  • 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 interferes with the sensations of the prostate for some men.


If he wants cock stimulation

  • Here you can decide to keep going and give him a handjob (if he wants that or wants to do it himself) or have him turn over and lay on his back for a handjob/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 handjob 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



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  2. I really like this new forum setup Ruby. The Tribes site gets a bit challenging to navigate. This particular tutorial should be a required read for any couples considering pegging as part of their sexual activities.
    Not only is the slow and careful approach safer, it’s also highly erotic, improves communications between couples and definitely broadens intimacy and appreciation for the uniqueness both bring to the sexual arena.
    IMHO, if more people employed this approach to all sexuality in their relationships, we would need fewer psychologists in our presently, dysfunctional society.
    Rock on sister. You’re providing a great service to humanity.

    • William

      Not only is the slow and careful approach safer, it’s also highly erotic, improves communications between couples and definitely broadens intimacy and appreciation for the uniqueness both bring to the sexual arena.

      Well said! I think I’m going to quote you here…

  3. Without you revealing anything too personal, I would find a recounting of your evolution to pegging quite interesting: the lust aspect, the ‘romantic’ discoveries and progression from your initial encounter / techniques, to more sophisticated ones as increased knowledge & experience expanded your repertoire. Also, at what stage of your life did all your longings come to fruition?

    • Just found this comment – so sorry for the delay. I will read and answer it on my podcast #70 (Ruby Ryder’s Pegging Paradise free on iTunes).

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  5. Okay so my boyfriend really wants to do it and I’m beyond nervous. I’ve just never done anything like it before and I’m scared I’m gonna be bad at it or he isn’t gonna like it or something is gonna go wrong. Please help me and be able to face my fears. I’m not against doing it just really nervous to attempt it.

  6. Ruby, long ago, probably years now, I read a piece from you about light role reversal. It was back on peggingparadise.com. I can’t find it now! My wife and I have FINALLY started talking about this stuff, and you had a wonderful write up about giving the man a chance to be the more submissive partner. (My wife and I have very ‘traditional’ roles in the bedroom) You explained it better than I ever could, about the man wanting to experience what the woman does, the taking in of their partner, etc. Do you know where that article might have ended up?

  7. My hubby and i have been trying pegging for about a year and sometimes i want to and other times it is a turn off. I want to please him but just dont always like it what do i do? I am willing to try anything he wants so i just need to be more dominant!

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  9. My wife and I have explored this activity and we both enjoy it. It is difficult to explain how it feels however it really turns me on to see her turned on and moving as she does. To all of the women out there; don’t be worried about not being good at it. If you are truly excited and turned on about it, you will be good at it. I am not gay, I am not bi and I have nothing against either of those orientations. I am 100% heterosexual and most likely considered a manly man. I do enjoy seeing my wife get excited, moving her hips, moaning, etc. It is the best.

    Good luck to all of you and thank you Ruby for publishing this site.

    • Thanks very much for sharing this. I love hearing from the manly man peggers!
      I’m going to read this on podcast #181, which will be posted January 2nd, hopefully early in the AM.
      Oops! Now I’ve done it. I blew it and forgot to include your comment in the podcast. 🙁
      I will reserve it for a future one… – #183!

    • Yes!
      Finally! I read your comment and responded on podcast #183, which will be posted tomorrow, just past midnight PST. Thanks!

      Lots of Love,

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