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Sex toys for virgin bottoms

Never had a dick in your butt, but keen to give it a go? Experiencing the feeling of getting fucked before your first time bottoming is the best way to get ready for awesome, pain-free anal sex. 

Sex toys are a bottom’s best friend, so here we’ve outlined an easy and cost-effective way to get yourself ready for some action.

First up, you’ll need some basic equipment:

  • Condoms: These are an easy way to keep fingers and toys clean as you experiment with anal play, plus it’s great to be ready with condoms at hand for when you do bottom for your first time. Condoms are available for free from
  • PrEP: If you're HIV negative and struggle with consistent condom use, you could consider taking PrEP to stay safe. But remember that while PrEP is great at preventing HIV transmission, it won't protect you against other STIs like gonorrhoea, syphilis or chlamydia.
  • Water based lube: Endinghivnz condom and lube packs come with plain, water-based lube, but for starting out with toys we recommend having your own bottle as well. Lube prevents damage to your butthole and makes everything feel fantastic. You’re far better off having too much than not enough.
  • A small butt plug: Start out with a nice small plug and make sure it has a base to prevent it going completely inside. For cheaper toys it is important to make sure they are made from a body safe material. Toys made from medical grade silicone are ideal because they are both body safe and flexible.
  • A standard size dildo with a base: The best starter dildo should be made from medical grade silicone and have a flared base (this is very important). A 13-14cm length with a 3.5cm diameter it is a nice, manageable size.

TipWhen you think you’re using enough lube, double the amount.
Lube is the best way to help your body comfortably adjust to penetration, so don’t be afraid to use a lot!

Now that you’re set up, it’s time to play! We’ve broken full preparation down into three steps. Some guys will be able to do all three steps in one night, but most beginners will have to work towards all three across a few days or weeks.


Start out by making sure your nails are cut short and tidy. You can also have a shower if you want to feel extra clean. Start jerking off, then, when you feel ready, begin moving your fingers towards your butt and start feeling your hole. You can put a condom over your finger for hygiene if you like, then add some water based lube to your finger and bring it to your hole. The lube will feel cold when it first makes contact. Relaxing your anus can take a long time, sometimes 20 minutes or more, so just go slowly and enjoy the sensation.

When your anal muscles are relaxed enough you can start easing your finger inside your hole. The first few times it can be tricky to work out exactly what’s going on because there are two rings of muscle in your anal opening. When you’ve passed the first ring of muscle it can feel like your finger is inside, but there is still another ring to go. Gently pushing your anal muscles out as you push your finger in can help you get inside a bit easier.

When you can comfortably get one finger inside, try a second. Get used to how this feels and when you feel very comfortable, move to the next stage.


Butt plugs are T-shaped anal toys that sit inside your butt and allow you to feel stimulation against your prostate.

Butt plugs don’t need to be covered by condoms when you use them, but if you want you can put a condom over it to make cleaning the toy easier. Be sure to hold onto the condom at the base of the toy so that the condom doesn’t slide off and end up completely inside you during use. (If you're using any toys for sex though, it's a good idea to put condoms on them. Remember to change the condom when the toy gets taken out of on person and put in another).

When you’re ready for play, get your hole warmed up with your fingers and plenty of lube, then add plenty of lube over the plug and very slowly ease it inside. Butt plugs can be curved or straight, the curve is there to direct stimulation toward your prostate when inserted. If your plug is curved, insert it so that the curved tip of the toy points in the direction toward your belly-button.

Because plugs have a wider head and a slimmer stem, there will be a point where the toy slides into place. This can happen quite suddenly once the toy is in past its widest part and may feel strange. The first few times your prostate is stimulated it could also feel like you need to pee. Don’t worry, your body will soon start to recognise this as sexual stimulation and respond with a pleasurable feeling.

Most butt plugs can be worn when standing and moving about, so you can leave it in while you masturbate and get used to the feeling. Wearing a butt plug when you top someone can also feel really awesome.

When it comes time to remove the plug go very slowly and take deep breaths. Pulling it out too fast will feel very uncomfortable. After use give the plug a wash with antibacterial soap and warm water, and make sure you rinse it thoroughly because any remaining soap can irritate the lining inside your butt the next time you use it.


When you’ve gotten used to playing with your hole then it’s time to get something cock-sized in there!

When it comes to the dildo it’s much the same deal as the plug. Make sure your dildo isn’t too large and that it has a base to stop it going completely inside. When you slide it in go very slowly and use lots and lots and lots of lube. You can put a condom over it to keep it clean if you like.

Unlike the plug that sits in place once inserted, you can slide the dildo in and out to fuck yourself. Using heaps of lube will make fucking yourself feel a lot better, so it’s very important that you have enough lube on hand. Gently build your way up to getting fucked faster and deeper, and play around with different angles to see which ways feel really great to get fucked and which ways are uncomfortable.

When you’re ready to bottom during sex with a partner, getting him to use the dildo on you to warm you up will make sex a lot easier. Warming up with the dildo will get your hole ready, and it will let your partner get a feel for your ass, how tight your hole is and what angles work best.

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