How to bottom for the first time: a gentle guide

Almost every guy is nervous before he bottoms for the first time, and almost every bad first time comes from the same few things: rushing, not enough lube and not being relaxed. Take those away and bottoming can feel amazing, partly because the prostate sits just inside, a few centimetres in towards the front.

Before the day

• Practise on your own first. Fingers, then a small beginner butt plug, teach you how relaxing those muscles feels.
• Talk to your partner. Say it’s your first time and agree that you set the pace.
• Sort out protection: condoms, PrEP or both, and know your partner’s status if you can.
• Eat well and get some fibre in the day or two before; it makes the next step easier.

Getting clean

Many bottoms like to rinse first so they can relax and stop worrying. A gentle douche with plain lukewarm water 30 to 60 minutes before is plenty. Our douching guide walks through it step by step. Don’t overdo it: lots of water or repeated rinsing irritates.

Warm up, then warm up some more

• Start with plenty of foreplay. Being turned on genuinely helps you relax.
• Use lots of lube, and add more than you think you need. Your ass doesn’t make its own.
• Begin with a finger or a small toy and breathe slowly. Gently pushing out as something enters helps the outer muscle open.
• Move up in size only when the last step feels easy.

Positions that put you in control

• On top (riding): you control the depth, angle and speed. The best choice for a first time.
• On your back with a pillow under your hips: relaxed, face to face and easy to say slow down.
• Spooning, on your side: shallow, gentle and comfortable.
• Save doggy style for later. It’s deeper and harder to control.

What’s normal, and what isn’t

A feeling of fullness, pressure or needing to go is normal at first and usually fades as you relax. Sharp pain isn’t. If it hurts, stop, breathe, add lube and slow down, or call it a night. There is always another time. Some light spotting can happen; heavy bleeding or pain that lasts is a reason to see a doctor.

Lube matters

Water-based lube is safe with condoms and every toy. Silicone lube lasts longer and is great for sex, but don’t use it with silicone toys. Avoid numbing lubes: pain is your body telling you to slow down, and you want to hear it. See the lube guide for more.

Tip: A slim prostate massager or a small plug before the big night is the best practice there is. Ten minutes of relaxing with it teaches your body what to expect.