Intimacy and Pegging

Ruby Ryder shares standing naked woman pegging man laying face down on bed, lit candle
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Intimacy and pegging often go together in pegging, and an intimate connection isn't magically created by the simple donning of a strap-on harness.

The fantasy of hookup strap-on sex might make great erotica fodder, yet it rarely happens in real life. For most people, a minimum level of connection and intimacy is necessary to consider engaging in pegging. Intimacy is created through trust, understanding and sharing of confidences, among other things. So 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. It 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.

Vulnerability

Men are typically unfamiliar with receiving and being penetrated. There is a vulnerability and openness inherent in penetration that is completely new to men. Women are quite familiar with penetration 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 the vulnerability is part of the turn-on for men. Yet many times a man doesn't go to that space easily, and is uncomfortable being 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 may have little experience 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. Wearing and using a strap-on takes practice. The initial period of awkwardness is often alleviated by an understanding partner, one whom you have a comfortable and close connection with. The giver needs to trust that any learning curve is accepted gracefully by the receiver.

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. They 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. A full-bodied orgasm might be and very intense to experience and to witness. The sight of a man deeply opened up, exposed, vulnerable and completely sensorially overwhelmed...is a rare and beautiful sight to behold. However more than one woman has freaked out after 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. Trust is not part of 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. Few enough women show interest 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.

Intimacy and Pegging

Because of all these factors, it is more often an established couple who will engage in pegging instead of a casual hookup. The potential intimacy inherent in pegging exists for all the reasons mentioned. These factors are important to be aware of, lest couples encounter awkward surprises.

This information certainly does not apply to everyone. There are people who can practice pegging with a casual hookup, and may even prefer to. There may be some parallels here to regular PIV (penis in vagina) sex. Of course PIV enjoyed in a FWB manner is as valid as a deeply emotional and intimate connection - we all get to choose. But because pegging takes normal penetrative sexual experiences and reverses them, many unexpected things can happen, taking either gender by surprise.

©Ruby Ryder

7 Responses

  1. This is precisely why we need you Ruby! This should be required reading for everyone. And if they are a couple, both partners should read it. I especially like the section on trust. As a man who loves to be pegged (and is not afraid to say it) I consider trust the key ingredient to satisfaction – for all concerned. Thank you for understanding the needs of those who may possibly be missing one of the most intense experiences they will ever have.

  2. Nice to hear this really resonated with you, Dean. I’d written so many things about pegging and this subject seemed to be the missing piece. I do think it is important reading for all couples interested in pegging, and it is a subject that has not been broached well enough in current books about strap-on play.

  3. Just wanted to mention…
    I have discovered since posting this that there are indeed some men who experience pegging quite differently. They can only let go when they have no choice in the matter; when it is rough and they are being abused and there is little emotional connection. These guys come from the kinkier circles (FetLife.com) and they helped me to realize my way of looking at pegging is not the only way. Of course I write from my own experience as well as the majority of people I talk with. Just wanted to give a shout out to the kinksters that don’t share my POV. Thanks for explaining your side of the pegging equation. Whatever turns your crank – it’s all good!

  4. Hi Ruby,

    Your absolutely right about the other types of men. I am a very kinky guy that would love to take it rough with very little emotion. I have been pegged before by my gf , I have a 16″ long 3″ wide dildo in a harness , believe it or not , they do make large harnesses. I used to tell her ( fuck me harder , faster , go deeper and pull out fast) all that kind of talk, I miss it so much, since then I have been fucking bigger and bigger dildos. I can take a 4″ wide dildo now , about 10 inches deep, I get so horny all the time,

    I love taking it up the ass with big ones now. I think a 4″ wide dildo is the biggest I want to go , it’s big , it’s filling and it really stretches me to my max opening. I don’t want to rip my ass out.
    I have seen some people take a 5″ wide dildo , now that’s really big , I guess they have really been practicing regularly to achieve that size. I have to work out with a 3″ wide, then a 3 1/2″ wide and the I have a 3 3/4″ wide dildo before I can take the big 4 incher. Once it’s in it really feels so good, I start moaning and get in tears from having that much cock stretching my hole out.
    If I could find a woman that could help me and feed those huge cocks inside me it would be a lot more intense not knowing if she is going to go faster than I would expect. Also I would be on all fours and probably would be able to relax my sphincter muscles even more so I would be able to take it easier , faster , deeper , and I love to be popped. Popped is when you have a dildo with a large head and pull it out real fast and it pops the anal ring. God that feels so good.

    I’m going to say this about me and possibly every other man that has taken it up the ass. It it very very addictive and after you have been pegged with small dildos you crave bigger , every man does, they want to feel that stretch feeling, that’s what gets us off . I started out with a 1.5″ wide and moved up to a 2″ in no time then a week later I ordered the big purple ******** dildo which is 2.75″ wide head and I bought the vibrating one and she used to put the whole cock up my ass and turn it up on high , hold it in me. Then yank it out fast popping me. Omfg !!!! Nothing felt better than a big thick vibrating cock rubbing all over you prostate. I used this dildo so much that the vibrating bullets inside it stopped working. Then I just kept moving up in size , wanting thicker and thicker cocks inside me.
    Every man that takes it up the ass eventually want thicker , hopefully some people will reply to this and highly agree, it’s so addictive ????????????

  5. Absolutes are rarely true in this world of so many different experiences and different kinds of people.
    So…

    Every man that takes it up the ass eventually wants thicker…

    It is very very addictive and after you have been pegged with small dildos you crave bigger, every man does, they want to feel that stretch feeling, that’s what gets us off .

    While these are your experiences, they are decidedly not the experiences of other men. I intend to compose a quiz/survey to try and find out how many men take the path of size king versus the ones who don’t.

    You have, however, given me a lot of material for those who seek it, and I’m going to read your comments on Podcast #164! Thank you!!!

  6. I am 40 years old, my wife and I have been pegging for about 8 years now. In your arrival you touched on the emotional response. It more rare these days as my wife and i have been doing it so long, but the first few times you receive an orgasm from pegging, you are going to cry, and it’s an amazing experience. you will feel more loved and cherish in that moment than you have ever felt in your life. First time my wife was able to get me to have an orgasm from pegging, I shook uncontrollably for a min, and she stopped, thinking she hurt me. I tried to yell at her to keep pumping, but my brain wasn’t working, so it was just gibberish, which really scared my wife. We laugh about it now. Don’t worry if you see him shaking and looking like he is having a stroke – all is well, be proud and keep pumping right through. There is a strong bond that forms from pegging and you really understand the opposite sex. Please if you have not gone through it yet, give it at-least 3-4 chances. This was something my wife wanted to try, and I was against it, but I gave in. Now I request it once or twice a week.

    1. This is one of the magic things about pegging, I believe. There is so much vulnerability possible for the receiver and a deeper intimacy often results for the couple. I am so happy for you!

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