Bend Over Bro: The What How Why of Pegging

by Eva Sless - 26 August 2016 - 99 Member Comments
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What Is Pegging?

Although “pegging” itself has been around for probably as long as sex has been, the term itself is relatively new. Coined by sexpert Dan Savage in 2001 after an online search to find a suitable term, pegging is the practice of men being penetrated anally by a woman wearing a strap on. 

So, why does it even need a specific term? Doesn't “anal” cut it?

Pegging Doesn't Make You Gay!

Well yeah it should, but in this crazy world of ours, men having anal sex is often equated with homosexuality, and straight men have, for the most part, spent their entire lives avoiding being called the G word, and therefore often avoid having any anal contact at all. There's also a common thought that it's an act of “submission” and, while that is true in some cases, it's no more or less submissive than any other form of penetrative sex. It's all down to personal preferences and desires.

These excuses not to try are sad and irksome for a few reasons, the first being that it shouldn't actually matter one little bit if you are gay, or someone thinks you're gay, or if you are or aren't submissive or whatever! It's so irrelevant in the great scheme of things! And the second reason this fear of anal is sad and irksome is because, for the majority of men, it actually feels good. Not just good. It feels mind-blowingly amazing!

This is all to do with the way the male body is made up, and that little ball of pleasure that sits just underneath the wall of the anal cavity called the prostate. Yes, that little ball that can cause a lot of angst and fear in the male population (prostate cancer is one of the biggest killers of men today) can also be a source of great pleasure and ground-shaking orgasms.

How Do I Bring It Up?

Being open and honest is an important part of any relationship, and is the key to having the best sex life you can. If you don't know what your partner wants and they don't know what you want, then at least one of you, if not both, are going to be missing out on some great experiences. In fact in Adult Match Maker's "Under the Covers" survey 38% of Aussie men and 34% of Aussie women said that strap-on sex was one of their sexual fantasies.

There are a few ways to broach the subject. Watching porn or reading erotica together with pegging in it is a good way to bring it up in conversation. Visit an adult shop together and check out the strap on and anal toy range. Just being in there and having the items in front of you is a great way to start talking about it. In fact, having regular conversations about sex and pleasure is just good sense anyway. Not only does it keep you both open and comfortable about sex, it is also a great space to be able to broach new ideas and fantasies and generally be in tune with your partner's desires. Or you could always send them the link to this article and ask them what they think.

Take It Slowly

The anal cavity, as we all know, is very very tight. It can stretch, yes, but nowhere near as easily as a vagina can stretch. It's made out of completely different stuff. This also means that, unlike a vagina, there is no natural lubrication there and that can make it even harder to penetrate, so you really do need to use a lot of lube (like heaps), and go nice and slowly with something small, and slim to start. A finger or a mini butt plug is perfect for getting yourself used to it. If you're using toys make sure that they have a flared base. The anal cavity is notorious for sucking things up irretrievably, and that's a trip to the emergency room you really don't want to make. Another way the anus is different to the vagina is it is completely safe to douche which can be a good way to ease your mind of any messes that may occur.

Harnesses, Dildos and Strapless Strap-Ons

When moving to the act of actual pegging the advice is essentially the same. Start small and slim and work your way up. You can buy harnesses that come with dildos, or you can buy them separately, and almost all of them use the same sort of O-ring attachment systems, so it can be easy to buy a harness and pick and mix your toys. It really is a good idea to spend a bit of money rather than go the cheap route as the better the quality, the far more use and comfort you'll get. The harnesses themselves come in a few different styles and sizes (almost always adjustable so you can fit it to your exact size), and some are nicer to wear than others. The thicker the straps, usually the more comfortable, but everyone has different likes. A lot of harnesses come with small bullet vibrators that slip into a pocket on the inside for the wearer's pleasure, and there's all sorts of other fun toys she could insert while strapped in. Speaking of insertion, strapless strap-ons can be great. They are a sort of double ended “L”shaped dildo. The shorter end is inserted into the vagina and the long end protrudes out. I'll be honest and say they can be a bit tricky to use and get used to, and they really do give your kegels a good workout holding on, but they can also create a really intimate experience as you're skin to skin, with no harness barrier between you. My best advice is to actually go into an adult shop and talk to the staff about what you're after. They will be able to direct you to the best products for your needs.

Comfort is Key

As well as starting off small and slow, you can buy lubricants and creams with relaxing agents in them too. This helps the sphincter muscles to loosen a bit, making penetration easier and more comfortable. I do not recommend the numbing creams that some companies sell. This is for a couple of reasons. The main one being that the skin of the anus is very very thin and very easily torn. This can cause a lot of damage and pain and discomfort, and numbing the area means you won't be able to feel anything going wrong, which can lead to all sorts of issues. The other reason I don't recommend it is if you can't really feel it, you can't really enjoy it, so what's the point?

Although every body is slightly different, the prostate is usually a few inches inside the anal cavity (about to the length of your second knuckle) and just outside the front wall (towards the belly button). It feels sort of round and firm and definitely different to the rest of the anal wall and, when pushed against, or rubbed, or massaged can feel “utterly amazing... hard to describe in words” according one friend.

Prostate, Perineum and Penis, Oh My!

These three P's are the key to giving your man the most amazing, intense, toe-curling orgasms he's ever experienced in his life. Stroking touching and teasing these areas while stimulating his prostate is pretty much guaranteed to blow his socks off. Let him guide you with his movements and noises as to what combinations work best for him and learn together what the best movements and actions are.

Constant communication is key, so check in with your partner if you're the one fucking, and if you're the one being fucked let your partner know how great (or not so) it is so they know how better to please you.

So relax, guys. It's not only perfectly normal no matter what sexuality you identify with, it's also so fricken good you'll probably be cross with yourself that you didn't start earlier!

Enjoy the ride, boys... Literally!

Your Chance to Win a DELUXE STRAP-ON Courtesy of S(A)X Leather

If you enjoyed reading this article you might also like The Bottom Line on Anal Sex Taboos and 7 Reasons Guys are Obsessed with Anal Sex

99 Member Comments

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  1. BiMelbGuy2

    More than a week ago
    guys try pegging, it definitely worth it, then once you are comfortable with it try the real thing.
  2. Fellator2145

    More than a month ago
    It is something that I would like to experience.
  3. voodude

    More than a month ago
    It's the best!! If you don't ask, you don't get
  4. Squirtingtiger

    More than a month ago
    We had to change our profile picture from my wife wearing her/my favorite strap-on back to this pic because once we did got slammed with emails from guys! Jezz so many guys want to try this but seem to scared to ask for it from their own partners. All we can say is MAN UP and tell your partner what you want in bed.

    Leolady727

    More than a month ago
    In my experience, men are very bad at saying what they like/want - can be very frustrating for a woman!

    Privateer76

    More than a month ago
    But...aren't women the more intuitive sex,Leo?
    Maybe that's just a myth...

    Leolady727

    More than a month ago
    Intuitive, maybe, but not fecking mind-readers! You just CAN'T help yourself, can you? :-)

    Privateer76

    More than a month ago
    I can't, no. Shucks.
    Just do what I do - what I want and take them along for the ride! Men are simple...now a woman's unspoken desires - there's a challenge.

    Melody2973

    More than a month ago
    I'd never do it, it's not something I'd be comfortable doing and to be honest wouldn't turn me on one bit :)

    BiMelbGuy2

    More than a week ago
    LoeLady you can peg me anytime
  5. sean3431

    More than a month ago
    I love being pegged
  6. 1thatlikesthat

    More than a month ago
    theres a few men i know that should be pegged immediately.

    PeggingGuy

    More than a month ago
    lol

    james6969

    More than a week ago
    tony abbott and donny trump two that cum to mind !!!
  7. THORGODOFTHUNDE

    More than a month ago
    Just because you like a dildo in the ass doesn't mean you are any less of a man.

    Leolady727

    More than a month ago
    Hear, hear - nothing "unmanly" about exploring your sexuality.

    Privateer76

    More than a month ago
    Sarc/ ?

    THORGODOFTHUNDE

    More than a month ago
    Not exploring my sexuality, butt (pun intended)there's pleasure to be had.
    For both the guy & girl ??
  8. dmncs4007

    More than a month ago
    Haven't had the strap-on, yet, but have had the butt plug and the sensations from that were amazing. I had a great partner at one stage where she and I both wore our butt plugs and shagged each other into oblivion for a night. Am yet to find another girl like her, oh well one day I will, I hope.
  9. Youknowwho1691

    More than a month ago
    i am very curious about the whole thing.
    I have used toys by hand in playtime but am scared to ask for more.
  10. Joeee01

    More than a month ago
    very interesting , hard to find a woman like this who values a mans butt :P !
  11. XDressinKink

    More than a month ago
    best feeling one can have

    Squirtingtiger

    More than a month ago
    An even better feeling is eating pussy while being ass fucked but a hot minx with a strap-on. I'll change our profile pic to match this comment lol. Pegging is wonderful
  12. daveydave5

    More than a month ago
    Where do i meet such a woman x

    Squirtingtiger

    More than a month ago
    We might seem hard to find but when you do you always remember us lol
    xoxoxoxoxoxoxo

    PeggingGuy

    More than a month ago
    I found her :) and others too
  13. areluctantsub

    More than a month ago
    I've had a number of girls I've been with do it to me & each time they have been amazed as to how much they enjoyed it. The power of someone giving themselves to you is a real turn on. If you've never done it I highly recommend. Finding a woman by saying "Hey, want to fuck me in the arse with a strapon?" is the quickest way of them running the opposite direction. It's a shame but that's just how it goes.

    You might not be able to feel the strapon cock, but if you get a good harness, with practice you'll be able to orgasm as well. If you never get to O, use the dominance of the situation to grab the guy by the hair and use his face & tongue to get you off instead. ;)

    BTW just a little side note, guys that are penetrated understand more of what it's like to receive so it allows them to become better givers which in turn better lovers. Just my 2 cents worth.

    Privateer76

    More than a month ago
    guys that are penetrated understand more of what it's like to receive so it allows them to become better givers which in turn better lovers

    That's just an opinion my man.
    As my gay mate said to me once - "You don't have to be a horse to judge a horse show".

    areluctantsub

    More than a month ago
    A horse would give a more informed opinion on other horses if it could talk. :) You may call it an opinion & it is your right to do so. Not sure why you felt the need to tell me this but thanks? :)

    Privateer76

    More than a month ago
    It's called "refutation".
    Look it up.
  14. MsNikstar

    More than a month ago
    Ms Nik and I LOOOVE pegging...

    I love taking it and she loves giving it. Often in our group plays Ms Nik dissappears briefly only to make a grand entrence wearing her beloved strap on, looking to take on all cummers..... men and women. She gets incredibly turned on by the feeling of being the giver.

    Until.... we left our beloved harness along with a bag of other assorted toys in a bag in a hotel room in Sydney!!! NOOOOOOOOO............

    It wasn't until we got home to Melbourne that we discovered this, devistated.

    So, we're slowly rebuilding our collection but have yet to aquire a new harness, we have our fingers crossed Eva and AMM....

    Stay beautiful all....

    T&N x

    Squirtingtiger

    More than a month ago
    You should have called the hotel and asked for them back. I would have lol. It's not like anyone else is going to want them...Side not: The Ms in your profile is Smok'n' Hot! She could Peg me any day
    Michael xoxoxoxoxo

    Leolady727

    More than a month ago
    Hmmm, maybe I should do that for the "toy" I'm sure I left in Thailand :-)

    tomskippy

    More than a month ago
    WOW, Were you too ashamed to ring that Motel & ask for them back, maybe the room cleaners had some fun with them when they found them lol.
  15. Squirtingtiger

    More than a month ago
    We do it and both love it.
    I leave him in a state of ecstasy shaking on the floor uncontrollably when I pump his nice little ass
    He even has his own profile on amm specifically for this where he is looking for ladies that would like to do this but cant find a guy who will let them.
    That user name is PeggingGuy so if you are a lady that wants to try this then by all means wink at us or him and we will get back to you, Yes he has permission to play alone & We tell each other everything
    We can also host or come to you. His ultimate Pegging Fantasy is to be pegged while eating pussy or have 2 ladies take turns on him.
    So if you are interested in this come say hi
    Let the Pegging Begin :) or END.... Pun intended
    B & M

    missSupergal

    More than a month ago
    Yes please. I'm in.
  16. FoxyFever

    More than a month ago
    "These excuses not to try are sad and irksome for a few reasons, the first being that it shouldn't actually matter one little bit if you are gay, or someone thinks you're gay" now straight people are being discriminated for not trying to be gay. What a fucked up world we live in...

    Privateer76

    More than a month ago
    Yes - what a time to be alive.
    Never fear, the Gaystapo are already beginning to overreach. There will be a pushback in the opposite direction. They won't be pleased but c'est la vie.

    Leolady727

    More than a month ago
    "Gaystapo"???

    Privateer76

    More than a month ago
    Yes - like the Gestapo but with rainbow flags,not swastikas.
    Join our "progressive" movement to fundamentally change the world's greatest civilization, or else you're a bigot.
    Love Wins! What shall we push for next - polygamous marriage? Sure. Marry your Beagle? Why not! Paedophiles are just "born that way"? Yes.
    Look up the Overton Window and you'll see what I mean.

    DeliciousEva

    More than a month ago
    Homophobic AND misogynistic.
    You're the whole package.

    Get many dates?

    Best thing about the comments section is being able to weed out the "nope never evers"... So I guess we should thank you for your service.

    Privateer76

    More than a month ago
    Homophobic AND misogynistic.
    You're the whole package.

    Thanks for providing incontrovertible proof for the other bloggers/lurkers that the Gaystapo is indeed real.
    Thanks for playing,Eva.
  17. Ryan183

    More than a month ago
    I'll be the one doing the anal thankyou lol
  18. StolenWaters

    More than a month ago
    Love being pegged. I have done it a few times now and am definitely eager for more.

    Totally agree with an enema being necessary beforehand, both for cleanliness and to free up space.
  19. Fittlad

    More than a month ago
    I'm open and willing to try, Hopefully
  20. horneeDevil26

    More than a month ago
    any guys that have wondered but are scared because its 'taboo' or whatever.. you should definitely try it. You get some mind blowing orgasms.. i just struggle to find a decent plus size harness to fight my bigger busted partner. and the strapless ones are tough as a protruding stomach also makes it hard for her to use.
  21. tr3nt88

    More than a month ago
    Mmmm always wanted to try this :)
  22. sexyfunmale

    More than a month ago
    Sounds very exciting to me. I'm open to some mutual pegging if any Sydney girls like to play.

    Privateer76

    More than a month ago
    Errr...wouldn't you rather do her with yourself? Strange, but anal sex with a girl using a strap-on cock does precisely nothing for me, as a man.



  23. JustR8ted

    More than a month ago
    Each to there own but the thought of being pegged,myself,does nothing for me.
    The only begrudgingly object i've had in my rectum,was from my addiction days,where i had to smuggle contraband into jail,end of story.Anyhow,perhaps it's more to the fact,that i prefer to please others,other than,someone pleasing myself.Again,each to there own.I do love rimming a female though and giving anal,if that is,what she wants.
  24. Sweetangelic3

    More than a month ago
    I have been one that has always enjoyed playing with a mans prostate while worshipping his cock. I have owned regular sized strap-ons for a couple of years and a few men have trusted me to peg them. The pleasure of watching his enjoyment is awesome...

    Recently though have progressed to bigger toys and really learning more about the giving of pleasure. The sound of his moans as you slide into him is addictive (as is the look and feel). .

    Lol i am told that when you use anal grease to start with and put it around under the knob of the toy it gets in better, and when you think you have used enough lube add more...

    letstraveloz

    More than a month ago
    MMMM sounds good to me.

    sexyfunmale

    More than a month ago
    Sounds very exciting to me, Sweetangelic3. I'm open to some mutual pegging if you would like to play.

    way2direct

    More than a month ago
    Best feeling ever!

    Melody2973

    More than a month ago
    What do you really feel ???, it's a strap on so I don't understand how you ' feel ' anything as its not your anatomy :))

    funlover521

    More than a month ago
    Count me in.

    timmy961

    More than a month ago
    I love prostrate milking, but having a cock in me, rubber or real, turns me fucking on.

    Pandhforfun

    More than a month ago
    And that sweetangelic, is why we all love you darlink,xxxxxxxxxxxxxxxxxlick.
  25. Leolady727

    More than a month ago
    I find anal very enjoyable and am not surprised that it can be enjoyable for men, as well. However, I have never had a partner who was willing to give it a try.

    Takemeplease6

    More than a month ago
    If you like you can try that with me :-)

    Privateer76

    More than a month ago
    Lol.
    The Thirst. It's definitely real.

    roleplay62

    More than a month ago
    Lol i think many men will offer there services

    Mike.vic

    More than a month ago
    I would love to try it with you I am not shy to try new and exciting things si would be happily a willing subject for you

    Privateer76

    More than a month ago
    Leolady has set off the male subs Tea Party lol

    Leolady727

    More than a month ago
    Privateer - why do you find it necessary to "label" everyone? Exploring one's sexuality and sensuality fully does not make one dom, sub, straight or gay - just adventurous.

    Privateer76

    More than a month ago
    Exploring one's sexuality and sensuality fully does not make one dom, sub, straight or gay - just adventurous.

    I disagree.
    Isn't blogging wonderful? You get to read "icky" opinions you may not agree with.

    Privateer76

    More than a month ago
    As for me labelling others...you have it backwards.
    They label themselves.
    By their words ye shall know them.
  26. orangeman555

    More than a month ago
    I enjoy being pegged. Not interested in a man having anal sex with me but with a woman I really enjoy it. Much of the pleasure for me is the enjoyment the woman gets as well as the slapping into my butt. Internally I do not get much stimulation at all. I most enjoy it when the woman lifts my legs and I can look into her eyes as she takes me.

    I once was anally stimulated by a special vibrating toy. the woman was quite experienced at giving men anal sex. I orgasmed very strongly but did not ejeculate. It was amazing. I could not believe it when I looked down and saw I was dry after an explosive orgasm. She proceeded to masturbate me and I came a bucketload and it was equally as strong. One very memorable experience
  27. roleplay62

    More than a month ago
    This is one of the most trusting things you can do as a couple and watching the smile on my friends as they peg me is nearly as stimulating as being pegged itself
  28. Takemeplease6

    More than a month ago
    I had the pleasure to have that experience and it was amazing :-)
  29. Milana09

    More than a month ago
    I've tried this with an adventurous guy..it takes trust and a good sense of humour in equal measure. I had to practice a bit to get the hang of thrusting, wrecking a few rock melons along the way..but in the end (!) we had a lot of fun..and it didn't turn him gay :)

    JR1957

    More than a month ago
    I couldnt agree more...trial & effort and the results can be mind blowing well, for me as a guy anyway....and, no, it didnt turn me gay either!
  30. funlover521

    More than a month ago
    Yes I must admit I love it too. And it is addictive. Shame there are two few women that like to do it to men. So sad.
  31. sydneystorm

    More than a month ago
    Nothing like being spit roasted by 2 women ! Love it :)
    By the way.... I always thought pegging was when you put clothes pegs all over the body! I think the term pegging should be changed when it applies to strap ons. Silly term.

    AMM.Editor

    More than a month ago
    To confuse you further playing with clothes pegs in bdsm is actually referred to as zippering.

    AMM.Editor

    More than a month ago
    And the original meaning of the wording "pegging" was a pin of wood being fitted or driven into something so it actually makes total sense :-)

    sydneystorm

    More than a month ago
    Aaah thanks :)
  32. guy2peg7250

    More than a month ago
    It is the best orgasm I have had... Fun, sexy, and role reversal...I love it. Shame most are scared or assume one is bi or gay..WRONG

    Melody2973

    More than a month ago
    I'm not scared, nor do I assume one is bi if they dig it :)), don't assume all women think that. It's just not something that turns me on nor would it. I'm aware men are aroused in that area though :)
  33. Here.to.play

    More than a month ago
    Love being pegged! Only thing tricky about it is finding suitable playmates lol.
  34. littlehottie22

    More than a month ago
    when done properly truly can be one of the best sexual experiences for both the guys and the girl, just takes time and practice. But then to each their own

    shagus5

    More than a month ago
    couldn' agree more with you, its not for everyone, but if done properly can be an incredible experience.
  35. pebbleb

    More than a month ago
    Only one thing once you have been analy penertrated you will need it for ever it is highly addictive whether its a girl with strapon on a guy

    phoenixio

    More than a month ago
    Yes i like giving and taking. Anal orgasm can be
    intense. In a MMF situation The guys can
    please the woman and each other as well.
  36. mickyincasino

    More than a month ago
    any girls want to do it to me i love it
  37. bi4bi6969

    More than a month ago
    I love giving .... The pleasure on the guys face is more than enough to please me. Not everyone's cuppa tea but don't knock it till you try it. My strap on cost me nearly $300 bucks. Definatly go for quality. Although I do believe that if a man wants regular anal play he should go buy his own that he would like used on him.

    guy2peg7250

    More than a month ago
    Well said

    Melody2973

    More than a month ago
    Maybe being ' bi ' helps ;)), no desire to strap on a fake cock ;)
  38. trusted8

    More than a month ago
    I guess the key words here are "Everyone is different" and what works for one may not be great for another. No different to some females who may not necessarily enjoy all forms of sex (let alone be able to climax). I'm not professing to be an expert by any means, but in saying that, I have had some partners who have made to whole experience so fantastically enjoyable, just using their finger and others that want to punish you by shoving a dildo in bigger than your manhole is without any persuasion or build up....Slow and easy is the key. We are here to enjoy the moment, not be turned off.

    LadyDragon

    More than a month ago
    Go you! Will be pleased to accommodate you... and by the sound of it - you me!
    ;~}

    CuriousGentAB

    More than a month ago
    Agree trusted8. No pressure on the partner if they're not interested or turned off. They should enjoy themselves as much as yourself. Mental attraction. Had one who was amazing to be with as great friends, made life & chats amazing, sex out of this world, even when just vanilla sex. Thoroughly enjoyed being with her, including receiving anal
  39. kissm3kwik

    More than a month ago
    Ladies, I am straight but I'd be happy to be your test subject :)
  40. andy0071

    More than a month ago
    I let my gf finger me and wow it's the best thing ever now I'm wanting to try a strap on just have to get one
  41. Melody2973

    More than a month ago
    Not interested in doing that to anyone, I understand men dig it but not my cup of tea :))

    Privateer76

    More than a month ago
    It's not gay if a girl does it to a man?
    Yep, keep those hamsters spinning.

    Melody2973

    More than a month ago
    Never said it was 'gay ' just said it's not my thing :))

    Privateer76

    More than a month ago
    I was agreeing with you Mel.
    Should have put it as a stand alone post,not a reply...
  42. 50shadesoffun66

    More than a month ago
    Wow I have never tried it ,but it sounds like fun ??
    Are there any female volunteers to show me what it's all about
    DD ??

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