Welcome to Ask a Cleveland Sex Therapist. Want to ask Matt a question that could be tackled in a future column? Click here. Now, onto this week’s topic.
Hey Matt,
I want to ask my girlfriend to peg me but I am scared she is going to leave me. Any tips?
-Anonymous
Oh, pegging. One of the most divisive sexual acts among straight men. In talking with them, I usually find they fall into one of two camps: 100% into it or 100% against anything going near their butt because “bro, that’s not for me.” Ask any of my straight friends and they will tell you that I tell them all the time that they need to engage anally with themselves and in their relationships. We need to remember that it is actually very common for people to become curious about sexual experiences that fall outside of what we tend to label as “vanilla” sex. Human sexuality is not static; it evolves as we learn more about our bodies and what brings us pleasure. So, Anonymous, if you are finding yourself curious about something like pegging, that is not random or weird, it is actually quite exciting.
For those of you who may be in the dark, pegging is a consensual sexual activity in which a person, typically a woman or vulva owner, uses a strap-on dildo to penetrate their partner, often a man or penis owner, anally. While it is commonly associated with prostate stimulation, which can be highly pleasurable due to the sensitivity of that area, pegging is not just about physical sensation. It can also involve a shift in traditional sexual roles, creating opportunities for vulnerability and different forms of connection between partners. Like any sexual activity, it relies on clear communication, mutual consent, and a whole lot of lube.
When you take a step back and really consider what that involves, it makes sense why even thinking about it can bring up a lot. It takes courage to admit this kind of curiosity to yourself, let alone consider sharing it with a partner. Men are cultured in a very specific way when it comes to sex and any sort of butt stuff usually falls out of them script. There is vulnerability in naming a desire that pushes against traditional roles, especially for men who have been taught very narrow definitions of what sex and masculinity should look like. You are not just asking for a new experience, you are opening a door to being seen in a different way. I do not want you to see that kind of honesty as a weakness, because it is actually a sign that you are developing a more grounded and authentic relationship with your sexuality.
Before bringing a partner into it, it is really important to start with your own exploration. Get to know your body in a low pressure, private way. Grab the lube and let’s get to it. Start with your fingers and begin exploring your anus, or the opening at the end of the rectum and when you are ready, slowly insert one finger into the rectum. The goal here is not performance or pushing yourself too far too fast, it is simply noticing what sensations feel like, what your body responds to, and what thoughts or emotions come up along the way. The more familiar you are with your own body, the more confident and grounded you will feel when talking about it. You may have already done this and if so, maybe move onto other objects like a small vibrating dildo or a butt plug.
I hate that I even have to say this, but it still needs to be stated. This has nothing to do with your sexual orientation. Being curious about anal play or pegging does not suddenly mean you want a penis or that your identity has changed. It’s not like the moment something goes into your butt you are immediately going to start voguing and watching RuPaul’s Drag Race (although you should, because both are great). Pegging is about connection and exploring different dynamics of pleasure. The prostate, for example, is a highly sensitive area that can create a very different kind of experience. That is biology, not identity. When we separate pleasure from rigid labels, it becomes a lot easier to approach this with curiosity instead of fear.
There is also some interesting research and emerging conversations around this. Studies and surveys have shown that many straight men are curious about or engage in some form of anal play, even if they do not talk about it openly. At the same time, many women report that taking on a more active or penetrative role can feel empowering, especially when there is clear consent and communication. When a person moves from the one penetrating to now being penetrated, that dynamic can create a different kind of connection. One that has the potential of leading to a kind of total freedom that a lot of couples may never experience in their sexual relationships.
When it comes to actually bringing this up with your girlfriend, think of it as starting a conversation, not making a request with a deadline. Do you two already talk about your sex life? If not, that is the place to begin. You can start by simply asking if you can both be more open about it in general. Once that rhythm gets going, this will feel a lot less intimidating. This is not something you want to drop on her out of nowhere. Instead, you might say that you have been exploring your body more and came across something you are curious about, and you would love to talk through it together. Keeping the tone open, calm, and curious can go a long way. It also helps to share what draws you to it, whether that is wanting to explore new sensations or feeling interested in shifting roles in a way that feels safe (this is why we started with the personal exploration).
At the end of the day, just be prepared for anything that might happen. She might be onboard and already has a dildo in her shopping cart. She could also be unsure or not interested, and those feelings are also valid. This is where trust really comes into play. If she is hesitant, it does not mean rejection, it might just mean she needs time or more information. If she is open, then you both can start to build comfort together. Either way, the act of having the conversation is meaningful. You are showing up honestly and inviting deeper connection. I know it feels risky, but in my opinion, that is a huge win. This is the kind of foundation that leads to a sex life that actually feels like yours, rather than one you are just performing.
Matt Lachman is a Licensed Professional Clinical Counselor and Supervisor, AASECT Certified Sex Therapist, and owner of Cleveland Sex Therapy, located in the heart of Gordon Square. Since opening Cleveland Sex Therapy in 2019, Matt has been dedicated to promoting sex positivity and inclusivity in his work with individuals, couples, and polyamorous relationships. When he’s not helping clients navigate their sexual and relational journeys, you can find him enjoying a cold brew at Gypsy Beans, sipping a cocktail at Luxe, or relaxing on his couch watching reruns of Happy Endings. Ask a question of your own here.
Disclaimer: The advice provided in this column is intended for generalinformational purposes only and should not be considered a substitute for professional therapy or mental health treatment. Each individual’s situation is unique, and the insights offered here may not address the complexities of your specific circumstances. If you’re experiencing challenges related to your mental health, relationships, or sexuality, I strongly encourage you to reach out to a licensed therapist or mental health professional for personalized support. You’re not alone—help is available.
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