29. January 2018 · Comments Off on FAQ · Categories: Blog
  1. Do women love pegging?
  2. What’s the best harness?
  3. What’s the best dildo?
  4. What’s the best lube?
  5. What’s the best position?
  6. It feels awkward…what are we doing wrong?
  7. Can she orgasm while pegging?
  8. Can he orgasm while pegging?
  9. How can I try to minimize the mess?
  10. How can I convince my woman to peg me?
  11. How can I convince my man to let me peg him?
  12. Why isn’t he hard?
  13. Why can’t she fuck me like I fuck her?
  14. It just hurts – what are we doing wrong?
  15. We can’t find the prostate – help!
  16. Where can I find a woman who will peg me?
  17. Where can I find a man to peg?
  18. Does the man have to be submissive?
  19. Does the woman have to be dominant?
  20. What if I don’t want to reverse roles?
  21. Why do they call it “Pegging”?
  22. What Questions have I missed?


1) Do Women Love Pegging?

Some women absolutely do, yes. Click here to find out what Ruby loves about pegging.


2) Harnesses

There are a number of good harnesses. First, what to avoid..Steer clear of the cheap, poorly made harness with thin elastic straps – they will not hold the dildo securely enough and aren’t worth the money. I would not recommend Vac-u-loc harnesses because they limit you to the dildos you can buy and Doc Johnson is not exactly a quality name in sex toys. The “two-strap” style of harness usually has better stability and accessibility than the single G-strap style that runs between her cheeks and can get in the way if she wants any action with her lady bits. As with all toys, I say buy once and buy quality. Some couples prefer to get a beginner’s kit, but most couples go straight from the beginner’s kit to something more sturdy and better made pretty quickly, so consider skipping the beginner’s kit if you are an experienced in anal pleasure and ready for something larger to start with. If you have serious doubts either of you will like pegging try a dildo by itself (with her hand) first and if he enjoys it, buy a quality harness to go with it.

Beginners Kits – If you decide to choose a beginner’s kit Tantus makes them but I would advise the intermediate kit because the dildos in the ‘beginner’s’ one are not long enough to allow for thrusting in some positions without falling out. Also – be aware that if you decide to use a double-ended dildo, the Tantus “bend over” harnesses are not compatible.

Harnesses can be made from leather (strong, luxurious and yummy), vinyl (strong, shiny and cleans well), rubber (waterproof, flexible, cleans well) and fabric (comfortable and washable). Leather, vinyl and rubber are porous materials and are not meant to be shared because they are not sterilizable. Fabric harnesses are sterilizable to the extent of putting them through the washing machine. Make sure the “O” rings will accommodate the size dildo you want to buy. Make sure the measurements of the harness will accommodate the wearer. Ruby’s favorites? Aslan Leather…makes some yummy leather, vinyl and vegan harnesses. Aslan wins my sexy and comfortable leather/vinyl/vegan award. Spare Parts has a lovely collection of comfortable, infinitely adjustable harness that are all washable. I have to say the Spare Parts harnesses win the comfort, adjustability and easy care award. Their new harnesses have 2 pockets for bullet vibes.

Other things to consider when selecting a harness…what presses against her lady bits? The leather panel that the dildo sits on? The base of the dildo itself (great for vibe dildos)? Is that a sensation she wants while she is pegging – pressure against her clit? (I know it sounds silly but some women don’t.) How high or low does the harness sit and will that give her the pressure in the place she wants? Some harnesses have a special pocket for a bullet vibe. One can choose to place a vibe in the harness or in the dildo. Some women love harness vibes – some say the vibrations are nowhere near strong enough to do the job or the pockets that hold the vibes are poorly placed. Read the reviews before you buy! Some are not compatible with the double ended dildos, so make sure you know if what you are buying will work with the dildo you select.

3) Dildos

Ahhhh…so many dildos, so little time. First let’s talk materials. Silicone is by far the very best material for a smooth texture, ability to be sterilized, and durability. (Don’t get the toxic jelly dildos – no matter how cheap! You cannot sterilize them and they will expose your body to bad chemicals.) One of my favorite brands of dildos is Vixen Creations. The “Mistress” is a reasonable size for beginners. There are many other quality silicone dildo manufacturers you can find online, too.

I would recommend one with a curve – helps stimulate the prostate. Make sure it will fit snugly in the ring of the harness. And don’t let your eyes be bigger than your ass and buy something too big. That happens more often than you might think. Also, don’t let your apprehension prevent you from selecting anything larger than your finger – you might as well just use your finger. Practice moderation – 1″ diameter and 5 – 6 ” in length works for most beginners. Size and shape can be very individual. Some men love ridges…some don’t. Some men say it’s the girth that gets them off, others say it’s the length and position of the dildo.

There are also “skin-like” materials out there…”Vixskin”, “Tantus O2” etc. They are expensive and they are really nice; a solid inner core and softer outer layer to mimic a real penis. Some people (including me) love them but if you decide to try them out please read this and make sure to get one that is sterilizable – most of them are toxic or porous which means they can hold bacteria.

A word about double-ended dildos like the Tango, Share and the Feeldoe…most couples find that these cannot be used without a harness, no matter how sexy that may be to envision. I would like to emphasize that they are on the advanced end of pegging toys for the majority of people. Some couples love them, but almost all women need a harness to hold them in. The difficulties arise from a) vaginal muscles being no match against the anal sphincter so they are difficult for most women to even keep in, b) the insertion point is the only point of balance as opposed to a nice snug two strap harness which will let you push up down and sideways and c) imagine dealing with all that when you are just learning how to fuck someone else! Not recommended for beginners, especially for women who are even a little reluctant about pegging – you don’t want the additional complicating factor to put her off pegging forever.

4) Best Lube?

You will probably need to experiment yourself here because there is no one lube fits all. Keep in mind you need to use a water based lubricant with Silicone toys. There have been reports of a few very high grade silicone lubes being compatible with silicone toys – but I would test anything on the base of your dildo before using it. Using silicone lubricants on silicone toys can damage your expensive toys. Also – do your own research and decide whether you are comfortable using petroleum products for your innermost passage or other ingredients used to preserve lube that some people consider slightly toxic. For example, this article talks about certain lubes being toxic to cells and tissues because of dissolved salts and sugars. Here’s a quote from the article:

Astroglide, a water-based and therefore condom-compatible lubricant, was found to be the most toxic of the lubes studied to cells and tissues. KY Jelly was also highly toxic to “good” bacteria in rectal tissue. The team found Elbow Grease and ID Glide had intermediate effects in terms of toxicity. Dezzutti and coworkers found PRE and Wet Platinum to be the safest — a fact touted by Wet’s CEO.

My favorite water based is completely natural Boy Butter H2O which is creamy but long lasting texture with no stickiness – and a mild, pleasant scent from the shea butter ingredient. Also noteworthy is Maximus. It is clear, has a gel-like consistency, is made with anal play in mind and lasts a long time without getting sticky. Maximus does have preservatives that some people react to, though. There are many lubes – buy small sampler bottles and test them to find your favorite. This is especially important because there may be an ingredient you react to in the lube and it’s great when you can just throw away the sample size and try something else.

5) What’s the best position?

Depends on what you want to achieve…

Missionary rates high for intimacy (face to face), high for prostate stimulation and high for access to his cock. Depending on how a man’s testicles hang, he may need to hold them up while you thrust…or end up with sore balls the next day. She can hold his legs up, he can hold his legs up, she can put his legs over her shoulders or you can use a sex-sling to do the work for you.

Doggy Style (the man on all fours and the woman behind) rates high for the woman’s visuals, high for ass access (for spanking) and medium for cock access (reach around).

Cowboy rates high for comfort for the woman (he’s doing the riding) high for prostate stimulation (he rides it how it feels best) and high for cock access.

Reverse Cowboy (the man faces her feet) rates high for ass access (spanking), high for the woman’s visuals and high for prostate stimulation (he rides it how it feels best).

The Chairman rates high for intimacy (face to face), high for woman’s comfort and high for prostate stimulation (he rides it how it feels best).

Bulldog (Advanced): The man on his hands and knees and the woman above and behind him with her legs on the outside of his. Here is the visual (with genders reversed). Rates very high for prostate stimulation and high for both ass access and visuals. The woman needs to have very strong thigh muscles. (I didn’t know this was the name of the position but knew about the website of animated sexual positions and was fairly sure I could find an example with the genders reversed – voilà !)

With all these positions…there are so many variables. Let me give you just one example from my personal experience. My legs are quite long (36″ inseam). The distance from my hip to my knee is longer than most people I know. That meant with Doggy Style I had to spread my legs very wide to be at the right height for his ass…so wide it was not as comfortable as it could have been. Pillows can be used to adjust heights sometimes, or if you want the best – get a Liberator sex cushion to play with.

6) It feels awkward…what are we doing wrong?

Nothing. It will feel awkward at first. Women were not born with cocks and it takes a while to get the hang of strapping one on. They also are not used to being the ones running the fuck. Men are normally not used to receiving and being vulnerable. Getting comfortable with something new just takes time.

7) Can she orgasm while pegging?

Absolutely. Not all women can orgasm while pegging their man, but many can, and there are different ways to reach that goal. One is to have a bullet vibe in the base of the dildo (in which case you need to make sure that the harness you use is open in the back so the base sits against her lady bits). One way is to buy a harness with a pocket on the back of it specifically made for a bullet vibe. One way is to have a double ended dildo that is stimulating her at the same time she is fucking him. There are some women who can orgasm simply from pressing against the harness while they are fucking their man. (Go back to the harness discussion for specifics and links.)

8) Can he orgasm while pegging?

Oh HELL yes. Absolutely. Again…not all men can orgasm while being pegged, but most can. This is where it gets a little involved, though. Some men have erections while they are being pegged. Some men don’t. Some men have erections that come and go. Whether he is hard is not an indicator as to whether he is enjoying the pegging…it is just an individual thing…and nothing to worry about. So moving on to orgasms…a man can orgasm from combined cock stimulation and pegging, which men say is about 10 times as strong as an orgasm with just cock stimulation (and produces much more ejaculate). Some men can also orgasm just from pegging. A prostate orgasm for a man is sort of like a G-spot orgasm for a woman. And then there are men who can have multiple orgasms from prostate stimulation. So the answer to that is a big yes.

9) How can I try to minimize the mess?

Keeping it as clean as possible is a combination of diet, thorough showering, anal douching or enemas, and liberal use of towels because of the liberal use of lube. You will find more information about that in this article: “Keeping Things Clean“. If you have never tried anal sex before, it is not normally as messy as you might imagine. Some people never douche or use enemas and don’t have significant problems with messes.

10) How can I convince my woman to peg me?

The answer to that question is actually pretty involved. Read about it here.

11) How can I convince my man to let me peg him?

The answer to that question is pretty involved, too. You can tell him you found something that will give him an orgasm 10 times more powerful that anything he’s ever experienced and produce a lot more come. That will do it for about 75% of sexually adventuresome men (okay, that’s an estimate with no studies to back the figures up, I admit). For the rest, or for the reluctant….read more here.

12) Why isn’t he hard?

If he is not hard….don’t freak out. There are a wide variety of penile responses to anal stimulation. While getting pegged some men will stay hard the entire time, some men’s erections will come and go and some men’s cocks will never get hard. Pay close attention here, though…his erection or lack thereof is not an accurate indicator of whether a man is enjoying the pegging. The best way to know whether your guy is having a pleasurable experience is to actually ask him. Good and open communication is essential during pegging, especially in the beginning. So keep asking if he likes what you are doing if you have any doubt. Some men have even reported that they do not like their cock stimulated during pegging because the sensations are different and it detracts from the prostate pleasure.

13) Why can’t she fuck me like I fuck her?

Women…were not born with a cock. They need time to get used to it. So in the beginning it will seem awkward and hard to manage. From a man’s perspective, it can be frustrating. The balance and natural roll of the hips takes time to perfect. The stamina takes time to build up. The muscles need time to develop. Which all means you just simply need to practice. Yay! It is likely your woman will appreciate you more once she dons a strap-on and fucks you – she will realize that the grace, strength, endurance and balance required to fuck is significant. You guys rock!

14) It just hurts – What are we doing wrong?

Pegging is not for every man. There are indeed some men who despite loving the idea of pegging, they do not feel any pleasure from their prostate or it’s just painful and never gets any better. If you are following all the rules (go slow, use lots of lube, relax, bear down like you are trying to have a bowel movement, start small) then either he just isn’t a man who enjoys pegging or there is a possibility he may have a medical condition (like hemorrhoids) that causes pain when his anus is penetrated. Best to check with a doctor if you have concerns in this area. Pain is an indicator – don’t ignore it. Pegging done correctly should never be painful.

15) We can’t find the prostate – Help!

Here is a map for you. Take a good look at it. The man should find a position that is comfortable for him. Face down with a couple of pillows under his hips is usually a good one. She sits on the bed behind him and uses her finger (gloved if preferred). If she has long fingernails fill the finger ends of a latex glove with cotton balls and then put on gloves before you begin. Anal exploration and long nails do not mix! You want to avoid tearing or scratching the rectal lining at all costs.

I like to use my middle finger, because it is the longest and the prostate can be difficult to reach sometimes. (I have met women who say their fingers are not long enough to reach their man’s prostate and they have to use a toy.) Insert your finger about 2 inches and press downward toward his belly, stroking gently. Poking is not recommended, most men do not like that sensation. Explore and get feedback about which spot feels the best. If he’s turned on the prostate will be much easier to find. The more turned on he is, the more his prostate swells and can be located easily. When a man is about to come it’s amazing how you can feel the prostate get bigger and harder and then release.

Like the G-spot, sometimes men have to sort of get used to feeling pleasure in that spot…it takes a while to wake it up. As long as it feels good, keep exploring and you’ll find it eventually. Using your finger in the beginning is many times easier than using a toy. Once you know where the prostate is, the positioning and angles of strap-ons and toys is easier to picture.

16) Where can I find a woman who will peg me?

Sorry guys, but there is no magic formula for finding a woman to peg you. In the end (pun intended) it’s the same as looking for a woman to date. Read more about this here and here.

17) Where can I find a man to peg?

The truth of the situation is that if you are a woman who loves pegging…you actually have your pick from a significantly large group of men who are looking for a woman just like you. You can explore FetLife(free) or OKCupid(free) or AdultFriendFinder($) and there will no doubt be groups of men bemoaning the fact that there are no women around to peg them. And I don’t mean to sound negative about that. They are interested in pegging and sad/frustrated that there don’t seem to be many women around who are into it. You will not have to look far.

In fact it will be more difficult to find a man who loves pegging but will approach you politely and respectfully when introducing themselves to you. There is something about the prospect of a woman with a strap-on that often seems to turn reasonable men into single-minded crude dudes. The better ones will keep their enthusiasm in check and approach you with manners and style…getting to know the woman behind the strap-on first.

Another possibility for you men is to consider going to a professional. If you can set aside your judgment of sex workers for a moment, have a read.

18) Does the man have to be submissive?

Not at all. Many men do find that they feel somewhat submissive because the act of receiving pegging requires openness and vulnerability. But there is no rule that men must be submissive, nor is there any likelihood that a man will suddenly become effeminate just because he gets pegged.

19) Does the woman have to be dominant?

Not at all. Many women who are interested in pegging have dominant traits, but it is not necessary to be dominant. For a woman, pegging requires being the one to run the fuck, the active and giving role. This can be a new experience for her, but it does not mean she has to turn into a cold demanding bitch who wields absolute power over her guy (not that there’s anything wrong with that!).

20) What if I don’t want to reverse roles?

Then don’t. Pegging can be a close, intimate and tender act between loving partners. There is really no need to look at it any way other than that. If you want to put your own particular kinky spin on it, then by all means go ahead, but that is entirely optional.

Now if there is something inherently mind-twisting about wearing a cock as a woman or getting penetrated as a man…well, that’s just the mind fuck you are dealing with there. It can be a turn-on. But it can also freak you out a little. Take a deep breath and go with it…and always keep open communication with your partner.

In the beginning of a relationship or even an established relationship, when trying something new sexually, it is good to have a debriefing after sex talk about what you enjoyed, what worked, what felt weird…everything. Builds great sex partners and increases intimacy to do this…and not just with pegging.

21) Why do they call it “Pegging”?

Pegging is defined by Wikipedia as a sexual practice in which a woman penetrates a man’s anus with a strap-on dildo. The word “pegging” was popularized when it became the winning entry in a contest in Dan Savage’s Savage Love sex advice column, held after an observation was made that there was no common name for the act. the word can now be found in Wikipedia and the Urban Dictionary…and all over kinky websites!

22) What Questions have I missed?

Is there a pegging question you were looking for the answer to and you didn’t find it here? Help me make this section more complete…go to the bottom of the page and click “Write Ruby” – send me your question!