You asked:

I’m really excited to try pegging with this girl I’m seeing, but I’m just not ready yet. I’ve used a vibrator anally before and it felt good, but mostly just made me feel full, if that makes sense. I bought a butt plug, but sadly I grossly overestimated my ability and it’s too big. How do I actually get better at this and is there something wrong with me?

Grace:

Everything you've said sounds very normal, especially overestimating your first plug (happens to the best of us). So no, there's absolutely nothing wrong with you.

What you need is an anal training kit. They’re made for this exact kind of buildup, and they’re usually way more cost effective than buying plugs one by one. You get a range of sizes so you can slowly work your way up, and a bunch of other anal essentials. I really like the b-Vibe Anal Training Set, but depending on how large a diameter you're hoping to eventually take, something like the Tantus Cone might be a good alternative, with the cone design helping to ease you in gradually.

And when you’re ready for the main event, make sure to pick an appropriate toy. I’d go for something smooth and simple, and the smaller it is, the higher the chance it'll fit. You can always upgrade later. I'd suggest looking at the Dillio Curious Five, it's designed exactly for this.

Frequently asked questions about pegging practice

Am I broken if I can’t take a big plug yet?

Nope - totally normal. Most folks overestimate when they start. Anal tissue needs time to relax and adapt. Start smaller, go slow, use lots of lube, and work up a size or two at a time. Mindset matters: treat it like training, not a test.

What’s an anal training kit and how do I use one?

It’s a set of progressively sized plugs or cones made to help you build comfort and capacity. Use the smallest piece first, wear or practice with it for short sessions (minutes to half an hour), relax your breathing, add more time as you feel good, then move up when the current size feels easy. Kits like the b-Vibe Anal Training Set or a graduated cone like the Tantus Cone are designed to ease you in.

How do I pick a starter toy (size, shape, material)?

Choose smooth, simple, and small to start. Look for a tapered tip and a flared base for safety. Silicone is a forgiving, body-safe choice. A small, simple model (like the Dillio Curious Five mentioned in the article) is a good starter. You can always upgrade later - progress beats bravado.

How should I β€œclean out” before pegging?

Light, sensible hygiene is best: don’t eat a heavy meal beforehand, shower, and if you want extra reassurance use a small bulb syringe with warm water for a gentle rinse (not a full-force enema). Don’t over-douche - frequent aggressive douching can irritate the rectum. If you’re unsure, consult a reputable sexual health resource such as Rainbow Health for guidance.

Is pegging β€œhealthy”? What are the benefits?

Yes - beyond physical pleasure, many people report relationship perks like better communication, trust-building, and shared intimacy. When done consensually and carefully, pegging can increase mutual attunement and pleasure.

What should I bring to the β€œtraining session” or first pegging attempt?

Bring lots of lube (avoid silicone lube with silicone toys - use water-based or a recommended hybrid), condoms for shared toys or easier cleanup, a small towel, the smallest plug or dildo you’re comfortable with, patience, and a non-urgent safety word or signal. Go slow, check in often, breathe, and use positions where you feel relaxed (side-lying or you on your stomach can be gentler than full-on missionary).