When Pegging Hurts but You Still Want to Serve

Dear Mizz Geena,

I could really use your advice, because I’m starting to feel like a failure.

My girlfriend is really into pegging. She loves it, talks about it constantly, and has made it clear that it’s a big part of her dominance and sexuality. I’ve been trying my best to get into it with her, and I want to be good for her. I’ve taken her maybe a half-dozen times now, but the truth is… it just hurts. Every single time.

We go slow, we use lube, we try different positions. But I end up screaming in pain or tensing up so much that we have to stop. It’s frustrating for both of us. She hasn’t said anything cruel or impatient, but I can feel the disappointment building. I know she’s had partners before who took her easily, and I can’t help but feel like I’m falling short.

What am I doing wrong? Is it normal for it to hurt this much at first? How long does it take to get used to it? I want to please her, I want to give her that kind of access to me, but I’m terrified that she’s going to lose interest if I can’t take her the way she wants.

Please help.

Sincerely,
Hurting and Hoping

Dear Hurting and Hoping,

First, take a breath—and then take some pressure off yourself. You’re not failing. You’re exploring a new, vulnerable experience in service to your partner’s pleasure and your own growth. That is not failure. That’s courage.

Let’s talk about the physical part first: yes, it’s absolutely normal for pegging to be painful or uncomfortable in the beginning. The anus isn’t designed to take penetration the same way a vagina is, and like any new physical activity, especially one involving muscle control, it takes training, patience, and practice. Even something as simple as your breath or mindset can influence your body’s ability to relax. Pain is a common early response when tension overrides arousal.

But you can change that.

Let’s retrain your body, gently. Think of pegging as a journey, not a test. If you’re only practicing with full insertion and full-size toys—or going straight to your girlfriend’s strap-on—you’re likely skipping the foundational work. Here’s what I suggest:

• Use smaller toys or fingers regularly, outside of your partnered sessions. This is personal training for your body, and it lets you learn what your muscles need without pressure.
• Practice breathing through discomfort. Exhale slowly as something enters you. The goal is to feel pressure, not pain.
• Include anal training in your solo masturbation. This pairs arousal with the sensation and helps your nervous system associate it with pleasure instead of fear.
• Warm up more than you think you need to. Pegging isn’t just physical—it’s psychological. Seduction, surrender, teasing—all of this will relax your mind and help your body follow.

And now, let’s talk about the emotional side.

Your desire to please her is clear and admirable—but don’t let your self-worth hinge on your performance. Submission is not about how much you can take. It’s about showing up with openness, honesty, and willingness. And the reality is, communication is a bigger turn-on than pain tolerance. You’re already demonstrating that you care about her dominance, and that you’re committed to pleasing her. That, in itself, is deeply submissive.

If you want to be proactive, have a gentle, confident conversation with her. Try something like:

“I love giving myself to you, and I want to learn how to take you better. I’ve been struggling with pain, but I’m willing to train. Will you help me ease into this at a pace that keeps me wanting more?”

You might be surprised—what she truly desires may not be that you take her like a porn star, but that you submit to her lead, even in your vulnerability.

One more suggestion? Consider watching or reading together. Explore pegging guides, anal training tools, or erotic stories that build anticipation. Turn this into a shared journey. That kind of intimacy is the real goal—not just the physical act itself.

You’re not broken. You’re becoming. And she’s lucky to have someone who cares enough to ask these questions.

With confidence, lube, and a whole lot of patience,
Mizz Geena

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