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.

Vulnerability

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.

©Ruby Ryder