A reader asks advice on whether he'll ever be able to have anal sex, especially as he finds it uncomfortable fingering himself.

A reader asks advice on whether he’ll ever be able to have anal sex, especially as he finds it uncomfortable fingering himself.



I find it quite uncomfortable when fingering myself and i get sore from it. I actually want to try being a bottom but since I can’t handle fingering I don’t think I could do it with another person, what do you think I should do?

Ty, 18

Dear Ty

Everyone’s ass is different and so is its ability to take various sized objects. Barring any medical reason, like anal fissures or piles it sounds as though you just need time and practice. As you’re quite young, the odds of you having fissures or piles is quite slim, but not impossible. If in any doubt you should definitely book to see your GP or visit to a sexual health clinic, who will be able to give you a sexual health check and you can discuss any issues you have.

In your letter, you didn’t mention whether you use lubrication when you try and finger yourself. If not, you should invest in some lube – but if you’re not in a situation where you can buy lube there are alternatives. There are, however, some liquids you shouldn’t use as a lubricant – these include body lotions and shampoo as these will irritate and potentially make your insides feel like the gates of hell.

If you can’t get hold of proper lube, it’s best to use a natural, unperfumed oily liquid. When you’re just by yourself there are a number of lube substitutes around the home that you can use, like olive oil, coconut oil, vaseline and aloe vera gel – none of these are good to use during sex with a condom. They will destroy the integrity of the condom. Always use a lube designed for condom usage.

Also, make sure you cut your nails and smooth them off. It’s important not to have jagged nails as you could catch your insides and cause a tear or rip internally.

Time is your friend

The trick with taking anything larger than a finger is time and patience and you should communicate that with anyone you have sex with. Don’t feel rushed into taking the D before you’re ready.

A word to the wise, it probably will hurt the first time you bottom for someone – and the chances are that you won’t be able to take it for very long either, but with time and practice (either by yourself or with a partner) you will be able to take it for longer and longer.

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Most guys can’t bottom for that long – even though porn can make it seem that they’re taking dick for hours at a time. It’s just one of those unrealistic expectations that gay porn has given us! Most guys cum within minutes of starting penetrative sex, a study found that men can last anywhere from 1 minute to 10 minutes, so you don’t need to be an ass athlete. You can always ask your topper to stop as well. Your body your rules.

Practice Makes Perfect

By yourself, after one finger, there are two fingers. Some people may want to try experimenting with various fruits and vegs, but there are some issues with using anything that doesn’t have a flared end. Without the splayed bottom it could disappear up inside you and that’s where problems can really begin. Ideally, you should try and buy a dildo or butt plug designed for ass play.

Take your time

There’s no rush – and when it comes to the actual sex take your time. If you’ve got time to prepare, you might want to douche (where you use water to get rid of poop in your anal canal and rectum) and lots of foreplay. Yes, get your guy to rim you and play and finger your butt.

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The advice listed above is not intended to replace or take the place of that of your own doctor, GP or medical professional who knows your full medical history. If in any doubt make an appointment with your doctor as soon as possible.

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About the author: Jake Hook
The editor and chief of THEGAYUK. All in a previous life wrote and produced songs on multi-platinum records.