Best Anal Sex Toys for Beginners: Starter Kits, Plugs, Beads, and Dilators That Hit Just Right

Nobody is born knowing how to bottom. At some point, every “natural” you’ve ever hooked up with quietly went through the same awkward phase of too-much-lube-not-enough lube, bad angles, and accepting that it’s definitely not going in today. Anal training toys exist to make that phase less questionable and more intentional. Think of them like Couch to 5K, except the finish line is you actually enjoying anal instead of clenching for dear life.

Good beginner toys are small, smooth, body-safe, and shaped so your body can relax around them. Great beginner toys also make the whole process feel fun instead of clinical: a cute jewel here, a colorful plug there, maybe a little vibration when you’re ready to level up. This list is for curious butt rookies and “I tried once and it hurt so I panicked” veterans alike. As a gay guy who’s very much been in the “oh god, that’s too big” trenches, grab one of these toys below and your favorite lube, breathe, and remember: going slow is not only allowed, it’s literally the whole point.

Consider the following sex toys, anal beads, butt plugs, and accessories like a road map. Start off with the essentials, and explore your options in texture, size, and sensation.

our top picks for the best anal Sex Toys

• Best Beginner Anal Training Set: Lovehoney Silicone Jewelled Training Butt Plug Set for Beginners
• Best Vibrating Anal Trainer: Adam & Eve Vibrating Anal Trainer Set
• Best Silicone Anal Plug Set: Nobu Rainbow Silicone Plug Set
• Best Small Vibrating Butt Plug: Lovehoney Butt Tingler 10-Function Vibrating Butt Plug (3.5″)
• Best Gradual Anal Training Kit: Doobies Anal Trainer Set
• Best Anal Dilator Set for Gentle Stretching: Adam & Eve Expansion Anal Dilator Set
• Best Beginner Prostate Training Kit: PinkCherry Ready, Willing and Anal Prostate Kit
• Best Premium Vibrating Anal Plug: b-Vibe Trio Plug
• Best Anal Beads for Beginners: Lovehoney BASICS Anal Beads (6″)
• Best Anal Training Alternative to Butt Plugs: Blue Line 2-Pack Anal Finger Sleeves
• Best Anal Starter Kit: Lovehoney Get Started Beginners Anal Kit (4-Piece)
• Best Small Prostate Plug: b-Vibe Butties Thumb Silicone Prostate Plug
• Best Wearable Anal Training Set: They-ology Wearable Anal Training Set (5-Piece)
• Best Prostate Plug with Cock Ring: b-Vibe Butties Ringer Cock Ring Prostate Plug
• Best Glass Anal Dilator Set: Borosilicate Dilator Training Set

Best Beginner Anal Training Set: Lovehoney Silicone Jewelled Training Butt Plug Set for Beginners

This Lovehoney jewelled set is the training wheels of anal, but in a hot way. You get a progression of petite silicone plugs with tapered tips and slim necks, so insertion and wear actually feel doable when you’re nervous. The sparkly bases make them easy to remove and weirdly confidence-boosting when you catch a glimpse in the mirror. If you’re starting from zero and want to work up in size without jumping straight into more serious gear territory, this is a gentle, cute starting lane.

Best Vibrating Anal Trainer: Adam & Eve Vibrating Anal Trainer Set

This trainer set is for anyone whose brain needs stimulation to match the stretch. It pairs a series of gradually larger plugs with built-in vibration, so you can start with the smallest one completely still, then turn on the buzz once you’ve relaxed. I like sets like this because you can stack sensations instead of throwing everything at your butt on day one. It’s very “intro course now, advanced seminar later” energy.

Best Silicone Anal Plug Set: Nobu Rainbow Silicone Plug Set

The Nobu rainbow set is basically a queer starter kit for your ass. These smooth silicone plugs come in graduated sizes that let you test what your body can handle on a given day, without suddenly leaping from pinky to eggplant. The color alone keeps it from feeling like a medical device, which matters when you’re trying to rewire your brain from exclusively thinking anal is absolutely terrifying. 

Best Small Vibrating Butt Plug: Lovehoney Butt Tingler 10-Function Vibrating Butt Plug (3.5″)

If your main fear is anything bigger than a finger, this small Butt Tingler is your friend. It’s short, slim, and made of soft silicone, but it packs multiple vibration patterns you can turn on once it’s in. The small size makes it ideal for absolute beginners, foreplay, or just getting used to the feeling of something being there without committing to a full-size plug. 

Best Gradual Anal Training Kit: Doobies Anal Trainer Set

The Doobies set looks simple, but the sizing curve is the magic. Each plug is only slightly bigger than the last, so your body has time to adapt instead of hitting a hard difficulty spike. They’re smooth, flexible, and easy to wear around the house with plenty of lube, which is great if you want to build tolerance gradually instead of doing intense sessions. This is exactly the kind of set I wish I’d had when I was first trying to embrace bottoming and realizing my body needed a bit more onboarding.

Best Anal Dilator Set for Gentle Stretching: Adam & Eve Expansion Anal Dilator Set

This dilator set leans more into deliberate stretching than “cute plug,” and that’s not a bad thing. The slim, elongated shapes are meant to gently teach your muscles to open and accommodate more over time, which is useful if your end goal is comfortable penetration. It feels a bit more clinical, but for anxious beginners or folks dealing with tightness or pain, having this kind of slow, structured option can be a game-changer. It’s kind of like pelvic-floor PT, but in your own bedroom with better lighting.

Best Beginner Prostate Training Kit: PinkCherry Ready, Willing and Anal Prostate Kit

This training kit is aimed at people with prostates who want to balance training and targeted pleasure. You get beginner-friendly sizes plus curved shapes designed to press toward the prostate once you’re ready for that kind of sensation. You can start off treating the smallest piece like a basic plug, then level up to more curve and pressure as your butt and your brain both relax. 

Best Premium Vibrating Anal Plug: b-Vibe Trio Plug

The Trio Plug might be one of the more serious toys on the list. It’s not enormous, but it has multiple motors and patterns that can make your whole pelvic floor sit up and pay attention once you’re ready. You can start on the mildest settings and just use it as a regular plug while your body adjusts, then experiment with more intense vibes when you feel curious. For a lot of people, this is the toy that turns anal training from work into something they genuinely look forward to.

Best Anal Beads for Beginners: Lovehoney BASICS Anal Beads (6″)

These BASICS beads are a straightforward way to ease into movement-based anal play. The beads start small and gradually increase in size, so you choose how far you want to go on any given night. The flexible strand makes insertion and removal feel controlled, and pulling them out during an orgasm hits very differently than a static plug. For a lot of people, these are the first toy that makes anal feel actively good instead of assigned homework.

Best Anal Training Alternative to Butt Plugs: Blue Line 2-Pack Anal Finger Sleeves

If jumping straight to a plug feels like too much, these finger sleeves are the one-step-up from bare fingers that a lot of people need. They slide over your fingers to add extra girth and texture, which makes anal exploration feel intentional without losing the control and responsiveness of finger play. Because your fingers can still bend and adjust instantly, they’re great for learning what angles feel good and what’s a hard no. These are perfect for shower experiments or for tops who want to give their partner a little more sensation without pulling out a whole toy kit.

Best Anal Starter Kit: Lovehoney Get Started Beginners Anal Kit (4-Piece)

This beginner kit is basically a sampler platter of anal feels. You usually get a small plug, some beads, and at least one other shape so you can test whether you like steady fullness, movement, or something in between. It’s ideal if you have no idea what kind of toy you’ll actually enjoy and don’t want to commit to just one style. Also, if you’ve ever said “this is the year I finally get into anal” out loud, this is a very literal way to back that up.

Best Small Prostate Plug: b-Vibe Butties Thumb Silicone Prostate Plug

This b-Vibe plug is shaped like a thumb giving your prostate a respectful little nudge. The size stays in beginner territory, but the contour is built to rest against the prostate once it’s fully seated. The base keeps it wearable, so you can practice with it during solo time or while you’re fooling around with a partner. If you’re ready to dip a toe (well, thumb) into prostate stimulation without going straight into heavy, vibrating hardware, this is a friendly introduction.

Best Wearable Anal Training Set: They-ology Wearable Anal Training Set (5-Piece)

The They-ology set is all about low-key, wearable training. You get a range of slim silicone plugs designed to sit comfortably between your cheeks, so you can start with the tiniest size and work your way up over days or weeks. The idea is gentle, consistent stretching instead of intense one-off sessions, which works really well if you’re trying to get ready for penetration in a realistic timeframe. 

Best Prostate Plug with Cock Ring: b-Vibe Butties Ringer Cock Ring Prostate Plug

Here, b-Vibe combines a slim anal plug with a cock ring to hit two zones at once. The plug portion stays fairly petite so beginners aren’t overwhelmed, while the ring can help you stay harder and more sensitive up front. It turns a regular jerk-off session into something that feels way more involved, without needing advanced toy skills or elaborate setups. For guys who want to start anal training but still want the main event to be their dick, this is a very fun compromise.

Best Glass Anal Dilator Set: Borosilicate Dilator Training Set

This borosilicate glass dilator kit is for beginners who want precision and control. The ultra-smooth surface makes insertion with lube feel slick and predictable, and you can play with temperature by warming or cooling the pieces under water beforehand. The gradual size progression lets you target tightness slowly, which can be helpful if you’re dealing with anxiety, pelvic floor tension, or past bad experiences. It’s less about wearing a plug for hours and more about short, intentional sessions where you focus on relaxing and breathing.

What to Look for In an Anal Sex Toy

If you’re new to butt play, shop like you’re buying first-time gear, not stunt equipment. In our “Anal Training” guide, we recommend starting with your own finger because it gives you total control and instant feedback; the same principle applies here: your first toy should make it easy to go slow, stay relaxed, and stay in charge.

Prioritize a tapered shape (so insertion feels gradual rather than abrupt), a non-porous material (100% body-safe silicone, stainless steel, or glass), and a flared base (non-negotiable). One of the smallest recommended diameters is about 0.3 inches, and increasing by about 0.25 inches as you get comfortable is suggested—so if you want a low-stress progression, beginner kits are great because they come in graduating sizes. Start small and simple—there’s zero prize for rushing.

GETTING STARTED WITH ANAL SEX TOYS

You actually have two sphincters in your butt: an inner one that you can’t control, and an outer sphincter that can be taught to relax, to open, to let pleasure in. It takes time to show the outer one how to have a good time and to help it get accustomed to accommodating big stuff. PLEASE: Don’t stick just anything up there. Your inner sphincter is a powerful, wonderful part of your body that can suck up whatever goes in like a sandworm in Dune.

The vibe is: slow, small, slippery, and not a performance. You can warm up with a finger first (to learn what’s happening in your body), then move on to a tapered beginner toy when you feel ready. Insert slowly, pause when you need to, keep breathing, and let your body soften around the sensation instead of trying to bulldoze past it.

Use lots of lube, and match it to the toy. An easy rule: silicone toys = water-based lube, while metal or glass can usually handle water-based or silicone lube. If you’re working through a set, stay on a size across multiple sessions until it feels comfortable and genuinely enjoyable. Progress isn’t linear, and some days you’ll want smaller, which is normal. A gut check is perfect: if it starts feeling like effort instead of pleasure, pause and reset—your body’s feedback is smarter than your ego.