If anal sex or booty play has ever hurt or scared you off, I promise you this: you didn’t do it wrong, you just started on the wrong step. Here’s what almost nobody tells beginners: anal is a staircase, not a diving board. Everyone panics because they picture the top step first, but you never start there. You start at the bottom, one foot at a time, and you don’t move up until the step you’re on feels genuinely good. This guide is your permission slip and your instruction manual at once — how to prep, the two rules that hold everything together, and the exact toys that walk you from your very first time all the way up to the good stuff.
If you’re short on time, here’s the bottom line: start small, use my code, and climb one step at a time. Keep reading for the full step-by-step below, or grab your toys now.
Get 15% off with code ANNETTE15 at lovehoney.com and we-vibe.com — works on every toy in this guide and anything else you shouold want!
My Full Step-by-Step Anal Training Guide
Below is my complete, hands-on walkthrough — how to prep, what to buy, and the exact order to climb the staircase so it feels good the whole way up.
The two things that hold the whole staircase together: lube and patience. Miss either one and it falls apart.
Step 1: Talk About It and Warm Up (The Part People Skip)
Before any toy comes out, two things have to happen — and skipping them is exactly why anal goes wrong.
Talk about it out loud ahead of time: not in the heat of the moment with someone’s hand already halfway there. If you’re playing with a partner, anal is a conversation you have with your clothes on: what you’re curious about, what’s off the table, and the agreement that either of you can call it at any second, no explanation owed. Knowing you can stop instantly is what lets your body relax, and relaxing is the whole ballgame. That conversation isn’t a mood killer; it’s foreplay.
Then warm up. Don’t go from zero to anal. Kissing, hands, whatever gets you turned on and out of your head. Arousal relaxes the body, and a relaxed body is the entire secret. The more worked up you are before anything goes near the back door, the better the back door goes.
Step 2: Prep So You Feel Relaxed
Let me be your cool older sister here. If you eat a decent amount of fiber and use the bathroom an hour or so before, you’re genuinely most of the way there. A warm shower relaxes everything and does more than you’d think.
If you want extra peace of mind, that’s what a simple rinse or basic anal douche with plain warm water is for — a little bulb, a little water, rinse until it runs clean. But don’t overdo it; going overboard actually irritates things. The mindset that matters most: this is a normal body part doing a normal thing. The more relaxed you are about it, the better it all goes.
Step 3: Lube: Non-Negotiable
Rule one of anal, and I can’t say it loudly enough: the back door does not self-lubricate. Ever. Unlike the vagina, there’s no natural wetness back there. Lube isn’t optional and it isn’t a nice-to-have: it’s the whole foundation.
I use Lovehoney Discover Gel. It’s water-based, so it plays nice with every toy in this guide (including all the silicone ones) and rinses clean. And because it’s a gel, it’s thicker than runny liquid lube — that thickness matters back here. It stays where you put it and gives you the cushion that makes everything glide instead of drag. Use more than you think, then use more than that. If you feel any drag mid-play, stop and reapply like it’s your job.
👉 What I use for this step: Lovehoney Discover Gel → · code ANNETTE15 for 15% off
Step 4: The Training Kit (Where Beginners Start)
If you’re brand new, this is your first toy, and I love that the beginner pick is also the most fun: the Firefly Glow-in-the-Dark Rainbow Trainer Kit. Three plugs in three sizes, and yes, they actually glow in the dark. Charge them under a lamp, hit the lights, and they glow. It’s playful and a little goofy — and that matters, because the number one thing that makes anal go badly is tension. Something that makes you laugh is doing real work.
Here’s why a graduated set is the right way to start. You get three sizes that build on each other: the Mini (3″ insertable, genuinely tiny — the “let’s just see how this feels” plug), the Small step-up, and the Medium (4.5″ insertable) once your body knows what it’s like. They’re soft, flexible, body-safe silicone, fully submersible so you can play in the shower, and cleanup is nothing.
The honest part nobody tells you: moving up sizes is not a one-night thing. Graduating from mini to medium can take weeks, and that’s completely normal. Some people spend two or three sessions on the mini before sizing up. Let the smallest one feel genuinely boring before you climb. There’s no prize for rushing, and a real cost to it.
Every plug has a tapered tip (starts narrow, eases wider) and a flared base — the non-negotiable safety rule of anal toys. Anything that goes in the back must have a flared base or retrieval cord. Always. No exceptions.
What I use for this step: Firefly Trainer Kit · code ANNETTE15 for 15% off — the best affordable on-ramp for beginners
Step 5: Your First Vibration
Once the smallest plug feels genuinely comfortable- comfortable, not tolerated — here’s your next step: the same idea, but now it vibrates. The We-Vibe Ditto+ is a vibrating anal plug with a smooth tapered head, a slim flexible neck, and a flared base that sits comfortably between the cheeks, so you can wear it and move without it shifting. You put it in and almost forget about it until it reminds you it’s there.
Here’s what vibration adds. A still plug gives you fullness, that lovely sense of pressure. But vibration wakes up the entire ring of nerve endings around the opening, one of the most nerve-dense parts of the body. For anyone with a prostate, it starts brushing up against it. For anyone without, it turns a worn plug into a low constant hum that makes penetration or clitoral play out front feel bigger.
Its best trick: it comes with a remote, with app control too. Drive it yourself or hand it to a partner. Wearing this to dinner with your partner holding the remote is a very specific kind of evening, and I recommend it. It’s impressively quiet, IPX7 waterproof, USB rechargeable, and runs two hours on a 90-minute charge. This is the step where anal stops being the thing you’re trying and starts being the thing you want more of.
👉 What I use for this step: We-Vibe Ditto+ · code ANNETTE15 for 15% off
Step 6: Prostate Play (For Bodies With a Prostate)
We’re near the top of the staircase, and this step is specifically for bodies with a prostate because if that’s you and you’ve never had it stimulated, there’s an entire category of orgasm you haven’t met yet.
Quick anatomy: the prostate sits a couple inches inside, toward the belly-button side. It’s often called the male G-spot for good reason pressure and vibration there produce an orgasm that’s deeper, fuller, and more full-body than penile stimulation alone. These three toys are all built to find it, and they climb in intensity.
Mantric: The Entry Point (~$99)
Your accessible entry into targeted prostate play. A curved, bulbous shaft shaped to seek out the prostate with precision, and a firm build firmness is what lets you actually press against the spot instead of flexing away from it. The textured base rests against the perineum for internal and external stimulation at once, with seven vibration modes, an LED panel that remembers your favorites, a remote, and a travel lock so it won’t buzz to life in your suitcase.
👉 What I’d start with: Mantric Rechargeable Prostate Massager · code ANNETTE15 for 15% off
Arcwave Perc: The Sweet Spot (~$119)
The step up, and the one I’d point most people toward. A dual-motor massager: one motor sits inside against the prostate, the other presses the perineum, both running at once. The internal arm bends to your own anatomy, so vibration lands exactly where your prostate is — not where the factory guessed. Four intensities and six patterns on the toy, unlocking 10 patterns across 10 intensities with the remote. Medical-grade silicone, waterproof, hands-free once it’s in.
👉 My top pick for most people: Arcwave Perc · code ANNETTE15 for 15% off
We-Vibe Vector+: The Top of the Staircase (~$149)
The fully loaded version — same dual prostate-and-perineum stimulation with a bendable internal arm, but with both remote and app control built in. Hand off the remote or let a partner run it from across the room or 100 miles away. This is the splurge for someone who already knows they love prostate play and wants the most control.
👉 The full experience: We-Vibe Vector+ · code ANNETTE15 for 15% off
So: start at the Mantric, land on the Perc, splurge on the Vector+.
The Rules That Make It Good
The toys don’t matter if the approach is wrong. The whole method in one place:
- Lube first, lube often: more than you think, every time.
- Go slow on entry: tapered end first, and let your body open on its own instead of pushing in.
- Pain is not the price of admission. It’s your body saying stop. Back off and add more lube.
- Breathe out as you insert: a relaxed body opens, a tense one clamps down.
- Flared base or retrieval cord on anything that goes in. No exceptions.
- Keep anal toys anal: don’t move them to other body parts mid-session without washing first.
- Clean everything with warm water and toy cleaner after. Every toy here is waterproof, so it’s easy.
Patience, lube, and the staircase does the rest.
Which Toy Is Right for You?
- Total beginner, nervous, not even sure it’s for you? The Firefly Kit: affordable, fun, glows in the dark, lets your body set the pace over as many sessions as you need. Nobody regrets starting here.
- Ready for more, or want something to wear during other play? The We-Vibe Ditto+ — vibration plus a hand-off remote changes the whole thing.
- Have a prostate and curious? Start with the Mantric.
- Already know you’re into it? The Arcwave Perc is the one I’d hand almost anyone.
- Want it all dialed up? The We-Vibe Vector+ — app, remote, full control.
An honest note: the We-Vibe and Arcwave toys are a bigger investment. If you’re not sure anal is your thing yet, don’t start there. Get the $40 kit, find out what your body likes over a few weeks, then climb. The expensive toys you’re intimidated by sit in a drawer. The affordable ones on the lowest step are the ones you actually reach for — and they can change your sex life.
👉 Ready to climb? Everything here is 15% off with code ANNETTE15 at lovehoney.com and we-vibe.com.
Keep Climbing
That’s the staircase: talk about it first, warm up and prep so you’re relaxed, start with plenty of lube and the Glow kit, take real time to graduate the sizes, add vibration with the Ditto+, and climb toward the prostate toys when your body is ready.
Once you’re at the top, you’re not standing on a step anymore — you’re at the deep end, and now you get to dive in and play. That’s a whole world of its own, and it’s exactly what I get into on my podcast.
For more on partnered anal, see my guide to anal sex with women and my beginner anal sex positions. Want the in-depth walkthrough for any single toy here? Sign up for my e-newsletter at talksexwithannette.com — that’s where each full guide goes out, along with my Substack, Talk Sex with Annette.
Grab your lube, and I’ll see you on the next step. Cheers.
Frequently Asked Questions
Does anal training hurt? It shouldn’t when you do it right. Pain almost always means a step got skipped — not enough lube, moving too fast, or a tense body. Go slow, use plenty of water-based lube, breathe, and stop the moment it hurts. Pain is a signal to back off and reapply, never something to push through.
How do I prepare for anal for the first time? Eat enough fiber, use the bathroom about an hour before, and take a warm shower to relax. For extra peace of mind, use a simple water rinse or basic anal douche — but don’t overdo it. Most important: talk about it ahead of time and warm up with plenty of foreplay, because a relaxed, aroused body is the key.
What’s the best anal toy for beginners? A graduated training kit like the Firefly Glow-in-the-Dark Trainer Kit, because it gives you three sizes to build up through gradually over multiple sessions. Start with the smallest plug and only size up once it feels genuinely easy.
How long does anal training take? It varies by body, but moving up plug sizes can take weeks — and that’s completely normal. Some people spend two or three sessions on the smallest size before sizing up. Let each step feel boring before climbing to the next.
Do all anal toys need a flared base? Yes — the non-negotiable safety rule. Anything inserted anally must have a flared base or retrieval cord so it can’t get lost inside. No exceptions.
What is a prostate massager and who is it for? It’s a toy designed to stimulate the prostate (often called the male G-spot), a couple inches inside toward the belly-button side. It’s for bodies with a prostate and can produce a deeper, full-body orgasm. Beginners can start with the Mantric and climb to the Arcwave Perc or We-Vibe Vector+.
What kind of lube should I use for anal? A thick, water-based gel like Lovehoney Discover Gel. Water-based works with all silicone toys and rinses clean, and the gel thickness stays put and prevents drag. Reapply often, since water-based lube can dry out over a longer session.
How do I get a discount on these toys? Use code ANNETTE15 for 15% off everything at lovehoney.com and we-vibe.com, including the Firefly Kit, We-Vibe Ditto+, Mantric, Arcwave Perc, and We-Vibe Vector+.
