Okay Ladies…

Let’s explore what makes you orgasm while pegging. Inquiring minds want to know, including your partners, beginners, other women who peg, and their partners!

Engaging in pegging gets me so hot that I’m dripping, but I am typically more about the orgasm that I give my partner than about me getting off. That’s the way I am built sexually. I love to give pleasure. We are all special snowflakes when it comes to our sexuality. Some women (like me) focus on giving pleasure. Others enjoy pegging men for their own pleasure, not caring about his. Some women are adept at the multi-tasking that men usually perform during PIV, and they can get themselves and their partner off. Some women come easily while pegging. Others never will. All of this depends on responsiveness of the participants, toys, technique, positions, and many other things.

Responsiveness plays a huge role in women’s orgasms during pegging, almost equal to the mental factor! Some women can get off just from the pressure of the base of the dildo against their clitoris. Of course this requires a good fitting harness that will securely hold the dildo low enough to cover the vulva and stimulate the clit. Some women get off easily because the thought of what they are doing is just so fucking hot. Some women need a Magic Wand level of clitoral stimulation to get off, and struggle to orgasm while pegging. So what are some of the factors that provide her pleasure?

Dildo Options for Her Pleasure


Every woman’s vagina is different! The various sizes and shapes of bulbs (the end that goes in her) will vary in comfort for each woman. There is no one size fits all. Here’s an article that compares doubles.

Double ended dildos can offer excellent G-spot stimulation. Although there is not a lot of in and out thrusting motion from the bulb end that fits inside her, there is definitely some movement as well as excellent pressure when fucking him. When that pressure hits the G-Spot just right, it feels amazing! For women who orgasm more easily from clitoral stimulation (or a combination of both clitoral and G-Spot) the best double with a vibe option is the Fuze Tango, with the We-Vibe Tango Mini Vibe. Rumbly and not buzzy, this mini vibe is the strongest, rechargeable, and waterproof. It has 8 different vibe choices (three speeds and 5 patterns). Though it doesn’t insert flush into the vibe pocket space, it will never get in the way, and makes it easier to remove for cleaning.

Keep in mind that Doubles require harnesses for 95%+ women who use them, despite the ‘strapless’ claim of many manufacturers. Read more about that here: The Truth About Strapless Strap-ons. Also, many women find that using a double to begin with is difficult, because they need to learn how to fuck first. The learning curve can feel pretty steep for beginners. Of course practicing and getting good at it is quite fun!

Single Dildos

The best clitoral vibe option for a single flare-base dildo is also made by Fuze (what can I say, those Canadians have it down). Their entire line of Fuze Singles, the Velvet, Harmony, Alpha and Wilde all have well placed vibe pockets to hold the We-Vibe Tango.

There are many other dildos made with a hole in the base to insert a vibe as well. Women who need medium to strong clitoral stimulation report that the vibration is insufficient with these models, but some women love them. The We-Vibe Tango may not fit in the dildos with a hole in the base, requiring a shorter bullet vibe instead.

When choosing a dildo with the idea of her clitoral stimulation in mind, think about what she enjoys. If she likes to get off with a motion of pressing against him to increase the vibe on her clit, be sure to choose a dildo that isn’t too long so that she can be in to the hilt (when the best vibe pressure can be obtained) and it is not too deep for him. Nothing worse than needing to push hard against him to get off but not being able to do so because the dildo is uncomfortable when it is in that deep.

The dildo vibe option is great for women who like to fuck with enthusiasm, because there is a cushioning layer of silicone between her clit and the hardness of the vibe. Vigorous thrusting is still comfortable!

Harness Options For Her Pleasure

Vibe Pockets

There are a variety of harnesses with pockets to hold bullet vibes. Spare Parts Harnesses (the Joque, Sasha, Bella and Tomboi) all have two pockets for bullet vibes, above and below the O-ring on the back face of the front harness piece. Using the We-Vibe Tango (which I firmly believe is the best mini vibe in the world) will not work because it’s too long. Regular bullet vibes will work, and you can decide which pocket gives you the most stimulation, or consider using both!

The Sportsheets Plus Size Harness has a vertical pocket for the bullet, which works better, allowing the vibe to nestle in between your vaginal lips, in which case the We-Vibe Tango will work great!

Using the vibe pockets with bullets may reduce the amount of vigorous thrusting you can do, because you basically have a hard metal or plastic vibe between you and the base of the dildo. But some women don’t need as much pressure, and are more sensual peggers, so the pockets work great.

Other Harness Options

If you are a woman loves something in her ass, and you have a two strap harness like the Jaguar or the Minx, the Aslan Leather Double Up Cuff allows you to use a nice butt plug, like the Tantus Ryder or the vibrating Je Joue Nuo, which is an amazing toy all by itself (remote and long distance phone app controlled vibrations). You can enjoy the feeling of your ass being filled while you fuck your partner! You could even give him the remote to the Nuo if you wanted to….

The Double Up Cuff can be purchased as an extra for the Jaguar, but already comes with the Minx. It should work with any 2 strap harness that you own, provided you can detach the straps.


The positions women prefer vary widely, and seem to have a large mental/visual component. One of my favorite positions for my own stimulation is laying down full length on top of my face down partner and slowly thrusting into his ass (even better if he’s got a Liberator Ramp under his ass). I do have a dominant streak, so that plays into my fantasies, like I am holding him down and he has no choice. Other women find that it’s the most exciting laying on their backs while their partner rides them, simply because the visual is so fucking hot. Doggie style can feel like the ultimate power trip and be extra stimulating mentally, too. Or consider this, if you are a woman who literally gets off because he gets off, you will want the position that produces an orgasm for him, which can trigger yours.

Foreplay Before You Start Pegging

Another consideration to help you achieve orgasm during pegging relates to what you do before you start! Engage in extended foreplay, kissing, and nipple stimulation. Have your partner give you oral sex, fingering or intercourse before you start. But he can’t come if he fucks you! He will lose interest in getting pegged…. 🙁

Other ‘before you start’ options include watching porn together, abstinence for a few days prior to pegging, and even edging for a few days before, too. All those can help!

Men Love to Feel a Woman Orgasm from Pegging Them

Many men talk about how hot it feels when a woman lets go and moves for her own pleasure instead of his. Many also say that the hottest thing ever is when a woman comes from pegging them. So this isn’t only about your orgasm, your partner will enjoy you getting off, too. That’s worth working towards. Practicing is such fun!


Over at I’m planning a special podcast.

Podcast #115 is going to be comprised solely of women’s stories and offerings.
Most of my readership and listeners are men. For this podcast…

I want to hear from the women.

Tell us all the things you love about pegging…
Tell us the story of your favorite pegging encounter…
Tell us about your first time…
Tell us about your last time…
Tell us about a funny time, or an embarrassing time…
Tell us about your favorite pegging fantasy…

One sentence, a paragraph, several pages – I want it all!

Spill it, Ladies!

You can write me at
Or send me an MP3 of your recorded story
Or record your story on my call line (805) 500-6544

We are going to blow the men away with podcast #115!


So, dear readers, it’s that time again. Periodically, I write a post about how pegging is not gay.

Why? Because the assumption is so very prevalent that monthly reminders are necessary for all the newcomers to my blog.

A reminder is also necessary for those of you who are considering trying it out but you have concerns. You guys lurking and reading and trying to decide if you really want to do this wild thing called “pegging” or not? Yeah. This post is for you. Here’s my message for you today:


Don’t listen to the little voice.

You know, the one that says…


He must be gay if he likes ass play.

If I peg him, he’ll leave me and go get a real cock.

If I like ass play I must be gay.

If she pegs me it’s will be like a gateway drug and I’ll want men!

That little voice is not your friend. That little voice is lying to you, misleading you and scaring you. Conclusion: that little voice is not nice. Ignore it.


The only thing that determines your sexual orientation is which gender you are attracted to – not what they do to you!


♥ If you are sexually attracted only to the opposite gender, you are heterosexual.
♥ If you are attracted only to the same gender, you are gay.
♥ If you are sexually attracted to both genders, you are bisexual.


In this age of marvelous and hi-tech sex toys, we can do so many things we were unable to do without them, no matter what gender we are. One of these things is pegging.  Pegging is just a heterosexual couple playing with sex toys! And believe you me, a strap-on is one fun toy to play with.

Take a look around the website and see what the men say about it, how insanely pleasurable it is.

Read why I like pegging.

Read what another woman says.

And ignore the little voice!


I hear from the women all too rarely. I think it is important to hear our point of view in order to understand what motivates us to lovingly fuck your delicious asses. Men often ask – why would a woman want to use a strap-on? What does she get out of it? There are many answers to that question, but sometimes it’s helpful to hear a personal story. The rest of you women out there…we would love to hear your stories, too…


Six months ago my fiancée, then boyfriend of two and a half years, told me he had tried anal play during masturbation and was interested in exploring this together. At first I was mildly upset/offended. Hadn’t I been a good enough lover? Was he bi-because he certainly isn’t gay. Most importantly we had been fucking for two years and he never mentioned it, although he had mentioned an interest in giving anal pleasure. I began to feel ill-equipped to please him, compared to a toned man with a raging hard cock.

Since then he has shared all of his sexual experiences with me, and I have learned that no, my future husband is not gay. Rather he is a heterosexual male who really enjoys having his ass fucked by a woman, and a prostate massage in tandem with being blown.

The best part is…I LOVE it. Seeing my glistening purple Share dildo right before I penetrate him gets me so hot, and I love hearing him moan as he gives me his ass and totally submits all thought.

There is something so erotic about being fucked and submitting as I am being penetrated. To simply feel, and not think. I am so happy to bring that same pleasure I experience to the best lover I have ever known and get to spend a lifetime in the sack with. Since we have started pegging, it has become a normal aspect to our sex life.

I am still coming to terms with accepting that I like to fuck and make sweet love to his ass, but I am coming to accept it. I enjoy taking his ass, and desire to be inside him almost as much as I long for his tongue on my clit when he is at work.

I love anal sex, and what is has done for my sex life.

-Happy Fiancée-

If you are a woman who wants to approach your man about pegging, this article is for you.

(If you are a man who wants to approach your woman about pegging click here.)

Plumisms 1


First, communication is the key. You need to be able to ask for what you want. If you can’t open your mouth and talk with your partner about sex, he is not going to magically intuit that you want to fuck him up the ass with a dildo. Take a good long look at your relationship first. Do your very best to practice Dan Savage‘s GGG – Good, Giving and Game.  “Think ‘good in bed,’ ‘giving equal time and equal pleasure,’ and ‘game for anything—within reason.'” We are not just talking about your man’s willingness to explore pegging with you…we are also talking about the state of your relationship with him…think about it. And before you blurt it out there that you want to pay his lovely ass some special attention, please read the rest of this article!


Okay, ladies – Trust. Is. Huge.

I am talking about your man’s ability to trust you not to out him. This is a bigger factor than you could ever imagine! For younger men whose generation is more open to and accepting of different types of sexual play, this may not be as big of a deal. But for men, say 30 and up, it can be the single largest factor holding them back from exploring pegging. Why? Because societal repercussions can be severe for men who enjoy pegging.

And even if they have a loving, intimate relationship with the woman of their dreams…what might happen if things don’t work out and they part? Will she tell? Will their circle of friends find out that he likes to get fucked? Will his friends or coworkers judge him? All those people likely have the same silly misconceptions about pegging that most people do and they might not look at it as just another passionate way to have sex with your partner.

Some men decide this is too big of a risk to take; getting outed. Perhaps because of their career, their religion or perhaps they live in a very conservative community. So the challenge is for you women to swear on whatever you hold sacred that you will never, ever out your guy. And keep that promise no matter what.

You know how men supposedly brag about the sex they are having? Well I’m sure there are some men who do…but the majority actually don’t. Ask around if you don’t believe me. They might make crude comments about the waitress or the woman that just walked by, but they do not talk about the details of the sex they are having with their significant other.

You know how women supposedly talk about….everything? That is actually true. Women do talk about the details. And men know that. So here is my advice around pegging. Just simply don’t ever tell. Make pegging a secret thing between you and your partner that you will never tell anyone, even your best girlfriend, even if you’ve had too much to drink. Make it a sacred thing between you and your guy so he can relax and really enjoy it without worrying about what will happen if anyone finds out…because he knows no one ever will.

So how can you reassure him that you won’t tell even if you don’t stay together? You make a big deal out of it. You tell him sincerely, to his face, making sure the timing is right (special dinner, just after sex, romantic moment, no one else around), swearing to him that it will be just between you two…forever. Another idea…consider giving him some compromising pictures of you naked that he can put up on the internet if you out him. That way you are both operating on trust.

There is also the kind of trust he needs to allow you to play with such a sensitive part of his body. Anal play is quite intimate. You are asking him to open up and be vulnerable, completely vulnerable. If you have received anal sex before you know how important technique is and taking thinks slow and easy. If you have not received anal sex before – please read up on it because ass play is best done after educating yourself! Here is a basic educational article for women who are beginners at male anal play.

Pegging is Not Gay

The biggest hurdle you will likely have to get beyond is the “No – that’s gay” hurdle. It’s like a knee-jerk reaction in many men that no one is coming anywhere near their ass…because that’s just…gay. There is a sad and rather unfortunately automatic connection between male anal play and homosexuality in so many people’s minds. Very common misconception that is 100% incorrect. The part of a man’s body that he enjoys having stimulated has absolutely no bearing on the gender he prefers to do the stimulating. (And actually there are a fair number of gay men who never have anal sex.)

Even if pegging does not threaten their sense of sexual orientation in any way…what stops most men is the thought that other people will think that they are gay or somehow less-than in terms of masculinity because they enjoy something up their ass.  For men…the blow back can be harsh. It leaves them vulnerable to ridicule, rumor and ridiculous assumptions from a largely homophobic society. Plus they certainly do not want their lovely partner to ever think that they are anything less than manly because they like ass play.

The Magic Thing to Say

Most men are pretty intensely sexual beings…if you tell them that pegging along with cock stimulation can produce orgasms 10 times more powerful than anything they have ever experienced with tons more come, most men will want to try it. I mean really, if you were a normal horny guy after hearing that could you really live the rest of your life not exploring pegging? No, I didn’t think so. Few men can.

Yet as with everything…there are all different types of men. Some will be quite ready to play at the merest suggestion. Some may require a little convincing but warm up quickly to the idea. And there are indeed those men who want nothing to do with anal play…ever, period…it’s “exit only” territory. Only you women out there have a sense which category your man falls into.


Remember that men are not used to receiving and being penetrated. There is a vulnerability and openness inherent in penetration that is completely new to men. Women are quite familiar with the feeling of being penetrated during sex. For men it’s a whole new deal. And that level of vulnerability can be pretty scary, surprising, and amazing all at once. Often that vulnerability is part of the turn-on for men, but that doesn’t necessarily mean it is easy for a man to go to that space or that it is comfortable for him to be seen there. Being able to trust that the woman understands this role reversal and will not suddenly judge him when he softens and receives helps him to more fully relax and allow that vulnerability to happen. Promise him that you will handle his ass with care!

Semi-Guerrilla Ass Play

Many guys get interested in anal because a creative woman slid a well-lubed finger up their ass during a blow job with quite good results. This does present a way to introduce your guy to anal play…even if it’s a little sneaky. I don’t prescribe to the sneak-it-in-there theory…but I have heard many a man say that this is exactly how they discovered that something up their ass really turns their crank. The part of this idea that really works is that prostate stimulation generally feels best when a man is already really turned on. But… instead of sticking your finger where you do not yet have permission to go, wait until he’s very close to coming and just circle your finger around the opening of his anus and see what kind of a reaction you get. The more turned on he is by your blow job the more likely you will get a good response. If he’s not giving you any signals and you’re not sure whether he likes it, ask him!


If your guy is on the fence, considering it but not sure…here are some testimonials from men who love it.

Best of luck encouraging your man to let you explore his sweet, handsome ass….

Ruby Ryder

(Many thanks to my friend fliedermaus for his help with this article. His willingness to be so open about the male viewpoint was invaluable to me.)

What does an orgasm feels like with combined prostate stimulation or pegging and cock stimulation?

Is an orgasm like that really 10x more powerful than a “normal” orgasm?

♥ It’s 100% more intense than a normal orgasm due to the fact that a normal pegging means a fair amount of prostate stimulation before hand, and so long as she doesn’t stop while he’s cumming it can feel like the world has gone dark and time has slowed.

♥ Like my penis no longer matters.

Joking aside 99% of any orgasm I’ve ever had with prostate stimulation is better than any orgasm with out. The difference in feeling at least for me is that a cock orgasm is centered around the gathering pressure in the cock that feels like it tightens until you finally get release. That release is brief and short lived but amazing none the less. A prostate orgasm ignored the build up of tension and is more a build up of waves that start at the point of pressure and slowly ripple out over the rest of my body. Each subsequent wave slowly building, rolling through my body, and crashing against the seams of reality bringing me to an ever higher and longer lasting state of release from tension I didn’t even know I had. Either way orgasms are great and we should all try and have them as often as we can. If having something in your butt may make that orgasm better why not at least try it?

♥ Prostate stimulation enhances orgasm by different degrees for different guys.

For me, I’ll admit that at first it feels rather odd (probably because it doesn’t happen very often) and it can be uncomfortable if there’s too much stimulation to either location. It turns me into a moaner (I very rarely make involuntary noise), and makes my orgasm incredibly intense, it also increases the amount of my ejaculate.

♥ I like a vibrator against my prostate while I masturbate. My body just goes limp when I cum. Complete loss of all control and a blinding orgasm.
It’s even better if you can get a partner to do it for you, though. If you can get a blowjob while they work the vibrator, it’ll change your life 🙂 Or a handjob while getting strap-on fucked is pretty awesome too. I came on my own neck while flat on my back once from that.

♥ Pegging and cock stimulation give a fantastic orgasm. If you can cum at the right moment, double orgasm, it is indescribable. Its full body and brain. When it happens to me I am out of this world for some time. I am very experienced with anal orgasms. To cum at the right moment (double orgasm) takes a lot of exercise and skill from the person pegging.

♥10x…I guess I’ve never attempted to quantify the power of my orgasms. I can tell you the following characteristics.

  1. I, also, shoot my load much further and harder from orgasms that correlate with anal penetrations. I can feel my come moving along the entire length of my shaft. I often edge quite a bit before I come during anal penetration because my body and mind go numb with pleasure after these intense orgasms.
  2. I stay harder longer after getting off with anal penetration than I do without. I also get harder more quickly afterwards. Starting with anal penetrating orgasms (APOs) has led to the longest, wildest, and most satisfying sexual romps of my life.
  3. While normally not a talker, I cuss, moan, pant and go crazy with a strap-on stretching me. My heart races just thinking about the energy it feels me with.
  4. Pegging and self play is all I’ve ever engaged in. I’m always a switch but I prefer the more submissive orgasm to the dominant one because of the intense out of nature experience I have. I’m a corporate leader type, captain of sports team type, by day and most nights, but the right woman can find a deep wild lust that’s animalistic.

So, I reckon that means its a 12x better orgasm. Hell, maybe even a bakers dozen.

♥ Pegging gives the most fantastic Orgasm. If done right in combination with stimulating the cock, it will blow your brains out. If hands free it will last and last, you will keep cumming. My friend gives me the most fantastic prostate massage, no cock stimulation, which can last for hours and you keep cumming and cumming. Better than pegging.

♥ It’s both a mental and physical orgasm. Like, I can feel it throughout the body whereas a regular, strictly handjob, orgasm has like a two-eight second feel. It’s one of those weird times where the body takes over and the brain takes a hike 🙂

♥I’ve never been pegged, despite my very intense desire to be, however when I purchased one of those Rude Boy prostate/perenium massagers, I got a taste.

For me, it’s the first time I’ve ever been breathless during and because of an orgasm. The pressure and the alien sensations at first were mindblowing enough, but when I got used to it, I find myself wanting to just grind there constantly. I’ve not quite had a handsfree orgasm from it yet, but I’ve had a good 10-15 minutes of constant dribbling until I get so pent up I need to bring myself to a full climax. What I’m saying here, is that I can’t wait for the real thing.

♥ I can’t say for full blown pegging since my girl and I haven’t tried it, but I was trying to describe the orgasm I got from her fingering my ass while she blew me to a friend, and the only thing I could think of was: It’s like the ghostbusters threw one of their traps near me, and my cum was the ghost getting sucked inside. It was mind-blowing.

♥ My response to this might be strange because I discovered at a very young age (13 I think?) that I could have prostate orgasms… and I used to have sessions where I had those because they are so amazing and different from the norm. But, as I have gotten older, I usually end the session with a combination of prostate and edging into a… I guess the analogy would be a blended orgasm?

Ten times more powerful would be accurate, but not in all cases. I would say the average prostate+cock orgasm is 10 times more powerful than the average masturbation session. But I have had some incredible regular orgasms with women before, that rival my prostate orgasms. It just comes down to how different they feel.

As others have said, any orgasm involving the prostate feels so deep inside. A regular orgasm does have an internal component, but it gets so overshadowed because of the strong contractions and pure pressure in the base and length of the cock. A regular orgasm feels so right, like I’m totally in control and working toward this pleasurable goal and release. With prostate stimulation the orgasm always comes outta nowhere; I’m working toward it but each one seems different in some way, and I always worry that this time, I won’t get there. And when it does come, I feel totally out of control, like my body is almost doing something wrong. The tension/release and waves of pleasure are almost unbearable.

Of course, my description might differ from those simply getting prostate stimulation while they come… those are usually pretty intense but nothing like the ‘blended’ orgasm. I have never been pegged either 😛 Prostate play has always been my personal thing I do. Luckily I have a partner that wants to get into it, so we’ll be doing that soon. Can’t wait!

♥ Most of the time my man doesn’t squirt that far when he does come but lately, since we have started pegging, he is now shooting it hard and far. One cum shot flew past my face while he was riding me and landed a few feet back. He was also thrusting uncontrollably to the point I was a bit concerned. ( I have NEVER seen him like this in the 5 years that we have been together. ) He has become a moaner, which he never does.

Intimacy is often a necessary ingredient in pegging, and cannot be created with the buckle of a strap-on harness.

The fantasy of meeting someone, going home with them and pulling out the strap-on makes for great erotica fodder, yet it rarely happens in real life. For most people, a certain level of intimacy is necessary to consider indulging in pegging. Intimacy is created through trust, affection, understanding and sharing of confidences, among other things. Why does pegging often involve intimacy? Let’s take a look.


Trust, Trust and Trust

Anal sex requires trust. Just as most women would not consider receiving anal sex during a casual one night stand, men can feel even more strongly about needing to establish trust before allowing a woman to peg them. Basically there is a lot of room for error. The anus is a delicate area of the body and needs to be treated with care and respect. Just as it is possible for a man to give bad anal sex to a woman because he is not knowledgeable about the act and has never received anal sex himself, the same can be true for a woman pegging a man. She needs to know what she is doing and he needs to know that she knows what she is doing.

Education is extremely important. Learning about the best ways to make it enjoyable and even more importantly the mistakes to avoid can literally mean the difference between pleasure and pain. Before you try pegging, whether you are the pegger or the peggee, doing your research first will help you enjoy a better first experience.



Men are not used to receiving and being penetrated. There is a vulnerability and openness inherent in penetration that is completely new to men. Women are quite familiar with the feeling of being penetrated during sex. For men it’s a whole new deal. And that level of vulnerability can be pretty scary, surprising, and amazing all at once. Often that vulnerability is part of the turn-on for men, but that doesn’t necessarily mean it is easy for a man to go to that space or that it is comfortable for him to be seen there. Being able to trust that the woman understands this role reversal and will not suddenly judge him when he softens and receives helps him to more fully relax and allow that vulnerability to happen.


I Don’t Know What I’m Doing

Women are not used to taking the reins and running the fuck. They have never had a cock, they don’t know how to use it and often have fears that they look as awkward as they initially feel. To be sure, wearing a strap-on and using it takes some getting used to. That initial period of awkwardness can be alleviated by being with an understanding partner whom you have a comfortable and close connection with. She needs to trust that he loves everything about her fucking him with a strap-on and that any learning curve will be accepted gracefully.


Emotional Responses

Just as the female G-Spot can trigger emotional responses in women, prostate stimulation can trigger emotional responses in men. Tears are possible. Yes, tears! Not many men will talk about it, but it does happen. Both G-Spot and prostate stimulation can touch a very deep, emotional part of some people. Those responses are not uncommon and are most often described as “good tears” or “letting emotions out that needed to come out”. (First time a man stimulated my G-Spot I was in tears.) It’s all good, but it may be surprising to experience and/or witness. Trusting his partner to be understanding and accepting of emotions or tears that might surface is so important for a man to fully open to the experience of pegging. This one is huge. Those deep emotional reactions can feel quite out of place during a casual hookup.


Her Reaction…to His

Men can have valid concerns about how their partner will react to their experience of being pegged. Aside from the potential emotional response, prostate stimulation can be so all-consuming for some men that it puts them in a bit of an altered state and the resulting orgasm can be full-bodied and very intense to experience and witness. The sight of a man deeply opened up, exposed, vulnerable and completely sensorially overwhelmed…is a rare and beautiful sight to behold. But more than one woman has gotten a little freaked out by seeing her man like that. Again, trusting his partner to accept what happens and not freak out is very important.


Peg and Tell

Social taboos seem to inflict more severe repercussions on men who enjoy pegging than on women who do. Many men will not want anyone other than their partner to know about their enjoyment of strap-on sex. Trusting their partner to keep that confidence is essential. That trust has not been established with a casual hookup. (The younger generation seems to be less concerned with this, which is quite encouraging. Slowly but surely, attitudes about pegging are relaxing.)


I Need a Woman to Peg Me!

I suspect all of this contributes to the difficulty men experience in finding partners to peg them.  There are few enough women who are interested in pegging to begin with. With the likelihood that a man will need trust and intimacy to feel comfortable exploring pegging, that takes it out of the realm of casual sexual exploration. So while thoughts of pegging may dominate a man’s fantasies, the reality often requires…a connection more akin to a relationship.

A man can pay a professional and trust her to be knowledgeable, keep confidences and not judge whatever reaction he has. I have recommended this to men who are intensely craving a pegging experience and I believe it is a valid option. Sex workers appreciate a clean, respectful client with specific needs. For men who crave it so much they tend to approach the strap-on before the woman, this can help to take the edge off.


Because of all these factors, it is more often an established couple who will engage in pegging instead of a casual hookup. The intimacy of pegging can be very powerful for all the reasons mentioned. It is good for both genders to be aware of these factors when considering pegging play, lest they be caught unawares at different turns.

This information certainly does not apply to everyone. There are people who can practice pegging with a casual hookup, and may even prefer to. Perhaps there are some parallels here to regular PIV (penis in vagina) sex, which can be engaged in either in a more casual, for fun type of manner, or can be deeply emotional and intimate – depending on the connection of the couple involved. But because pegging takes normal penetrative sexual experiences and reverses them, many unexpected things can happen, taking either gender by surprise.