GUIDES & ADVICE WELLNESS BLOG

Prostate Play Solo: Your First Night, Step by Step

Author: Tiffany M 5 min read
A man lying on his back on a bed in boxer briefs, knees up, head back on the pillow, eyes closed in pleasure, low warm light

So you've been wondering. Maybe you read something, maybe a bloke at the pub told you a story that went on a bit too long, or maybe you just got curious. You've got a gland about the size of a walnut, sitting a few centimetres inside your arse, and men keep saying it gives them the biggest orgasm of their lives. You'd like to find out, and you'd prefer that nobody else be there the first time. Fair enough.

First: it's got nothing to do with who you're attracted to. Having a prostate isn't a sexual orientation. Here's your first night, step by step.

Step 1: Get what you need

  • Lube, and lots of it. Water-based is safest with silicone toys. Wicked Simply Natural is a good gel for the job, and our anal lube guide has others.
  • Short, clean nails. File them smooth, if you're starting with your finger.
  • A small toy made for this. Skip the giant ones. The Anal Adventures Prostate Stimulator is $24.95, and it's held in place by your muscles. The Maia Colton is a bigger step, in 100% silicone with a remote and vibration. Whichever you choose, make sure it has a flared base or stopper. Never put anything in there that could get lost.
  • A towel. Just in case.
Anal Adventures Prostate Stimulator
Anal Adventures Prostate Stimulator

Step 2: Get ready

Go to the toilet, have a shower and wash thoroughly around the outside. Most blokes don't need to do any more than that, particularly if you're getting enough fibre. Our douching guide covers it if you'd feel better doing a quick rinse. If you do, wait at least half an hour afterwards. And relax. If you're worried about mess, that's what the towel's for. Nobody's watching, and you'll cope.

Step 3: Get turned on first

You really need to be aroused for this. The prostate tends to get more sensitive and easier to find, and you'll relax a lot better. Start with a wank, as you would normally do, and don't rush. Get good and hard. Take your time.

Step 4: Start outside

Lie on your back with your knees up, or on your side with your knees drawn up. Add lots of lube to a finger, and start by circling the opening. Press gently on your perineum, too, as you can sometimes feel the prostate from the outside. Keep touching your cock with your other hand. Let your body get used to it.

Step 5: Go in slowly

Breathe out, and bear down gently, as if you're pushing something out. That actually opens things up. Slide a finger in, just a little way, and stop there. It'll feel strange at first, and it might feel like you need to go to the toilet. That usually passes. Wait a minute or so. When you've relaxed, go a little further.

Step 6: Find it

Go in a few centimetres, about up to your second knuckle, and curl your finger towards your belly button, as if you're saying "come here". You're feeling for a firm, slightly rounded bump about the size of a walnut, on the front wall. It's often easier to find when you're hard. Press on it gently. You may feel a sort of deep, full pressure, or a sudden need to pee, or something that travels right down your cock. Many blokes say it's a bit strange at first.

You probably won't have a mind-blowing orgasm the first time. Lots of people just feel an odd pressure at first, and it takes a few goes to learn to enjoy it. That's normal. Don't press hard. It's a sensitive gland, and it's a gentle massage rather than a poke.

Step 7: Try the toy

Once you've got used to your finger, usually on another night, add lots of lube to your toy, and go in the same way. Slowly. With a prostate massager, you'll often find that it moves as you tense and relax your muscles, and that gives you a hands-free massage. Try squeezing and releasing, and breathing slowly. Then add vibration if you have it, on low. Keep stroking yourself, or don't, and see what happens.

Good to know

  • It shouldn't hurt. Pain means stop. Don't use numbing products, as you need to be able to feel what's happening.
  • Don't go from your bum to anywhere else without washing up first. Clean your toy after each use, and here's how.
  • See a doctor if you get persistent pain, bleeding, or if a toy gets stuck. Don't be embarrassed. Emergency departments see it often, and they don't care.
  • If you've had prostate problems or surgery, ask your doctor first.

If you try it a few times and don't get much from it, that's fine, too. Not everyone does. But if you do, then our prostate massager guide has plenty more for you, and multiple orgasms might be next. Enjoy your walnut.

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