One thing I have been hearing about over and over lately is couples who rush through the period of time between getting excited about trying out pegging, and the first time the actually do it.

There is so much to learn and so much to enjoy during that space of time! Not only will you really miss out if you rush through it, your initial experience with pegging might be more awkward and difficult as a result. So many ‘firsts’ happen, too! You don’t want to miss a one.

I’m big on anticipation. If I could give lovers a timeline to follow from when they share that first exciting moment of embracing the concept of pegging, feeling all that eagerness to explore, to the actual moment of insertion, it would look something like this…

  • For the next 5 or more times you have sex, explore his ass as a part of your foreplay. If you want to try rimming for foreplay, but aren’t sure about sticking your tongue in his ass, try a dental dam – they are sheer and ultra-thin – he won’t be able to tell the difference. Use fingers and plenty of lube. Gloves are optional. Take it really slow, make it a sensual experience. Stay in communication and have fun. Giggle and laugh if you feel like it. Sometimes exploring new territory is funny and it’s okay to feel nervous or self-conscious. Go so slow that he is arching his ass back to meet her fingers.
  • Around the 3rd or fourth time, once he can easily take a couple of fingers, use the beginner dildo that you bought for pegging. She can hold it in her hand and discover what angle, depth, and speed sends him to the moon. This is what she will be trying to duplicate when she straps it on.
  • Spend one evening staying in. She wears the harness while you both cook/eat dinner, watch TV, or clean the kitchen. This gets her used to putting it on and how it feels to have a cock! It also teases the fuck out of him to watch her walk around with it. Heh heh.
  • Finally – this is the night. He cleans out. He has no fear whether he can take the toy or not – he’s already had it inside him. She knows what she is aiming for after playing with the toy and her fingers. She’s used to wearing the harness and cock and knows how to put it on. The blanket is on the bed, because you’ve done this before. The lube is handy, along with a towel, and you are ready to begin pegging…


  • Write and tell me how it went and I will play the music for you on my next podcast!



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


Rimming, as sexy and hot and intimate and delightfully nasty as it is…is not everyone’s cup of tea. Yet some people love the feel of teasing their tongue into their partner’s ass and feeling them squirm with pleasure. And many people love the sensation of a warm wet tongue pushing into their anus. It can be exquisite. (Can you tell I am biased, here?)

But let’s back up (subtle pun intended) and begin at the beginning for those of you not familiar with the terminology.

Rimming: Using your tongue and lips to stimulate your partner’s anal opening – also called analingus.

Perhaps some of you out there are going ewwww. But there are many of us who love the sensuality of loving attention in such a vulnerable place. Others are turned on by the taboo factor and perceived nastiness of it. The anal area is definitely full of sensitive nerve endings and can be just the thing to stimulate a wickedly intense orgasm. Additionally, rimming can also be lovely foreplay to pegging.

So how does one go about “rimming”? Since you have found your way to this website I assume you take pleasure in or are curious about anal penetration (either giving or receiving). Because this site is all about the glorious act of pegging, I will concentrate primarily on male receiving, though women love rimming, too!

Rimming can be a delicious, teasing introduction and invitation to anal penetration. Men who are interested in the idea of pegging but are inexperienced or apprehensive can experience rimming to see if anal stimulation turns their crank. (I have yet to meet a man who didn’t enjoy it.)  The flutter of a warm wet tongue on his sensitive, puckered opening can produce spontaneous exclamations of pleasure…occasionally a full octave higher then normal…


The optimum positions for receiving rimming are either on hands and knees or laying face down with 2-3 pillows under the hips (or if you are a connoisseur of sex furniture – a Liberator sex cushion rocks.)

The advantage of the hands and knees position is that it will part his cheeks nicely, all the better to receive your attentions. Also, you can easily reach your hand underneath him and stroke his balls and cock for a mind-blowing orgasm.

The benefit of using pillows or a cushion is that it will allow him to relax completely while your tongue and lips are tantalizing his sweet ass…and for beginners, this can be important. If the pillows or cushion are placed forward a bit, giving his manly equipment some room, you can pull his cock back to stimulate it if that’s comfortable for him. Many times if you start with him on pillows at a certain point he will spontaneously get up on his hands and knees just because he wants…more. More stimulation of his cock, deeper penetration of his anus with fingers, toys, or perhaps a strap-on. But I do get ahead of myself…


Massage your partner’s back and butt to relax him. Kiss the back of his neck…brush your nipples against his back. Gentle or feather-light fingers on the small of his back, his butt, the insides of his thighs and his balls. Tune him in sensually. Then pull his legs gently far enough apart (if they are not there already) so you can settle yourself behind him and have the object of your attentions front and center. Knead and stroke his ass cheeks, kissing and licking them softly. Work your way gradually down his crack to his anus. Slowly. Rimming is something to take your time with.

The whole point here is that by the time your tongue actually touches his anus you want him to have been imagining how it would feel for the last 5-10 minutes; craving it. Even if your guy is quite experienced, approaching rimming this way is a first-rate erotic tease. If you get off on seeing your guy squirm – I highly recommend the slow approach.

The Act Itself

There are a variety of techniques that you can mix and match:

Reach your tongue as far as you can down to his perineum or “taint” and begin licking there, slowly working your way up to his anus.

Kiss his anus with soft lips, slowly, over and over.

Touch your soft, warm, wet tongue to his ass and just leave it there for a while, then slowly beginning to move it around.

Flutter your tongue around the edges of his sensitive puckered opening.

Lick him with regular firm strokes of your tongue.

Stiffen your tongue and insert it into his anus, basically fucking him with it.

Your partner will let you know which of these he likes the best, either by moaning or gasping…or pushing back to get more of the luscious thrills you are offering. Pay attention to these signs and you will discover his favorites.

What’s Next?

For some men, rimming can be intensely enjoyable for a fairly long period of time without any other stimulation. Others will crave fingers, butt plugs, dildos and/or cock and balls attention pretty quickly because rimming turns them on so much. At that point it is up to you (and perhaps the nature of your relationship) whether to indulge your man’s urges or make him wait for it.

My personal preference? There are few things as erotically thrilling as when I have made him wait for it so long that when his pegging adventure commences I am treated to his voice, rough with passion, pleading, “Fuck me!”

Bathe That Butt

Okay – I did this kind of back-assward here, because obviously, asses need to be washed thoroughly before rimming. Part of the act can involve a seductive bath or shower together so you are both squeaky clean. Enemas can be part of the ritual if that is something you enjoy, so that you know you are clean inside as well.

The possibility of STD and STI transmission is a very important consideration with rimming. You need to be fully informed about the risks you are taking if you decide to perform rimming without a barrier. As with any sexual activity, know the risks and then make your own decisions.

Butt (hee hee), my dear readers, the hour grows late and I will address that issue in detail in my next post. I know…that’s like placing a gourmet meal in front of you and asking you not to eat it until I give you the fork (you are so gonna use your fingers…). I guess I  am indeed an insufferable tease…!

Seriously, you can find that information pretty easily on the internet – so if you are hot to try out some things I described and can’t wait until my next post, be responsible and please educate yourself about the risks first.

Link to my article: The Risks of Rimming

Happy Rimming!

Ruby Ryder

A man found my website with the search words:

“i bled after being pegged”

This situation always concerns me. Anal tissues are much more fragile and subject to tearing than, for example, vaginal tissues (where babies are born from). So many people do not realize that care must be taken when approaching anal penetration. A LOT of care. And too many people don’t seem to realize that when I say slow I really mean slow…like half an hour of foreplay, not just sticking your finger in his ass for a minute and then two fingers for a minute and then shoving a dildo up his ass. NO!!!

If you go too fast with pegging, it can definitely cause problems. Bleeding is one of them. If you see any blood while pegging, call it a night, give his ass a rest and try in a couple of days. Usually there will be pain connected to bleeding, too. So some people wonder when to be concerned if there is bleeding. If it’s just a spot or two, no problem. You should still stop the fucking and let his ass recover. If there is more blood and/or it doesn’t stop, a trip to the doctor might be in order. These are the Mayo Clinic’s guidelines for seriousness of symptoms.

For the Newbies

Step-by-step foreplay in my article “Newbie Ass Play”