Well, every time I have anal sex or am fingered it’s really fun at the time but really hurts after. Is there something I’m doing wrong or what can I do to make it pleasurable?
Simon
Hello Simon,
The ass is pretty darn resilient and there’s a pleasure to be had from anal sex, but there are a few golden rules to make sure you keep safe and reduce pain.
It can’t be stressed enough lube is your friend. Use a good amount – and have a towel handy that you can wipe your hands, as it can get quite messy. **That** scene in Brokeback Mountain – as hot as it looks, is just not that realistic. A bit of spit and shove isn’t going to cut it. Use a good lube – and there are loads of lubes to choose from on the market. You might find that you get on with some better than others. Try the trial sizes until you find the perfect lube.
Take your time. One of the most misleading things about porn is that you can’t just stick it in – and that includes fingers. You need to take it gradually. You could start off with a bit of rimming and then move on to a finger – then if that feels good maybe two. Don’t just go for it. You will cause yourself a lot of pain.
Warm yourself up. You could do a bit of prep yourself before sex. Perhaps while you’re in the shower – or if you douche you could get your butt used to the feeling of a finger or two up there before you get down with your partner. Using warm water to douche could help you relax as well.
Anal Training. Why not try a set of dilating anal training toys. The toys vary in size and girth. You start small and gradually get bigger as you become accustomed to the size.
Finger maintenance. You say that it hurts after fingering, are your boyfriend’s fingernails ragged? If he’s got claws that a Gruffalo would be proud of it’s time to invest in some nail clippers for him. He may be, unknowingly tearing your insides – which will make the whole experience uncomfortable.
Keep the action smooth. Keep the fingering motion smooth and long and thin (goes right in). He shouldn’t curl up his fingers inside you – this is going to cause discomfort. No vigorous finger jamming like he’s Donald Trump giving a speech.
If you’re really concerned that there’s something wrong book an appointment to see your GP.
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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.
If you’re a gay, bi or curious guy chances are you might be up for a chocolate starfish stretch… But when you do it for the first time, there are just things you don’t expect.
(C) BIGSTOCK
We asked our wonderful community what they thought about the first time they had anal sex.
The pain (Allie)
How tight my ass was lol (Jim)
The pain after banging my head on the table lamp lol (Jon)
The agreement that more lube is always a must. (Brad)
Can’t really remember I was drunk . (Jim)
d
It didn’t hurt like I was expecting it too. (Jordy)
It was a romantic and powerful moment for this power bottom! I felt fulfilled! (Bri)
The pain! Omg the pain!!! Felt like being stabbed in the stomach and the sh*tter all at the same time! I’ve honestly felt less pain standing on a plug (Craig)
How bloody selfish he was. And the size of his manhood. Ginormous (W)
That it hurt like f**k, literally. And that I only truly enjoy it once I’ve become comfortable with my partner. (J)
Not to laugh at the other guys sex noises while inside. (Matt)
That my boyfriend who was 100% straight liked it very much. (Q)
The ability to actually stay awake !!! (Sean)
How much overhype there is. I was so bored, and have been every time. (Sean)
That not everyone likes doing it to ABBA! (Graham)
We get requests at THEGAYUK about all manner of things, one that is asked a lot is how to bottom.
Well, we’ve enlisted the help of top porn star Kit Wilde to give us some tips on how to make sure you put your best bottom forward and be a bottoming king.
Advice on these sort of subjects is difficult, for the simple reason that sex, like most things, is subjective. I could have sex with a one night stand and think it was pretty average and the following week you could have sex with the same person and think it’s mind-blowing.
There are however a few tips and hints on how to make bottoming easier and more pleasurable, again bare in mind that this is subjective so what works for me might not work for you. The key is to listen to your body!
WASH IT OUT
A douche or an anal enema is a bulb-like product used to clean the anal passage from waste. The enema is used to push water into your anal passage which you then expel repeating until the water being expelled runs completely clean.
You can get a douche for most adult stores (check out THEGAYSHOP) and most of them stock them in various sizes all pretty cheaply enough and if ordering online most stores offer discreet packaging.
Most anal enemas come with directions for use, please read them carefully before use, but generally, these 6 steps should help.
CLEAN BEFORE USE
Clean the douche well before use with warm soapy water, any muck or grime on it can increase the likelihood of contracting an infection, ensure the douche is clean of any soap as well before use.
LUKEWARM WATER
Fill the device with lukewarm water. Do not use scolding hot water or water with soap in it. Just plain old warm water, test it first, remember this water is going inside you, let’s try and not have a trip to A&E because you’ve scolded your rectum.
LUBE IT UP
Lubricate the douche and the anal cavity (that’s your bum hole), this makes it easier to insert, as a side note, your rectal cavity tears easily, so don’t just go shoving it inside you. If you’re struggling to get the flute inside your anus, take your time, relax, reapply more lubrication and try again. Need some lube, check out our selection of lubes.
INSERT AND SQUEEZE
Before you insert the douche, squeeze the bulb to release the air so the water fills the flute, this stops you pushing air into your body and means you won’t end up with trapped wind. Squeeze the bulb with ease allowing the water to fill you.
REMOVE
Remove the douche, keeping your grip on it whilst holding the water inside you. DO NOT release your grip on the douche as it’ll suck the water back into the douche. Only when the douche is fully removed from your body relax and release the water (it’s easier and less messy to do this on the toilet).
REPEAT
Continue the process until the water remains clear and free from any waste.
Although the use of an anal enema is very helpful in planned situations it’s not very helpful for those spontaneous sexual moments when you just let the mood take you. In times like these, you need to use something you can not buy from a shop.
You need communication, you might think it’s embarrassing to talk about but believe me, it’s far less embarrassing to say “do you know what? I might not be clean” than for your sexual partner to find that out the hard way.
If you’re in doubt take some time and go to the toilet, remember that while the anus and rectum do not usually store faeces, there may be remnants left behind so make sure to thoroughly clean the area around your butt, I’ve found that moist towelettes (baby wipes) really help with this or if you have a little more time maybe try a quick shower.
Now, this is the bit that may make a few people feel gross, but, trust me it’s far less embarrassing you finding something than your sexual partner.
The Finger Check
You can use your finger to check and see if you feel any remnants inside you, which can be removed pretty quickly. Yes I’m aware I am literally suggesting you pull your poo out with your finger but if you really want to have sex and don’t want your sexual partner to end with a messy penis, cleaning is necessary.
If you do clean yourself out with your fingers though, be sure to wash your hands very thoroughly. I am very aware that the process of cleaning out your ass is embarrassing, but please for the love of Cher talk to your partner about it.
Spontaneous or long-term partner, communication is important as it helps both (or more) of you understand what, if any preparations are needed to be made beforehand, it also lets everyone prepare for any potential accidents that may occur. Be aware that if they do occur, it’s ok, these things do happen just bear in mind that next time you might want to allow for more time to prepare.
Listen to your body
As a final note, remember it’s your body, take your time and enjoy yourself. If you’re not enjoying yourself listen to your body, change position or go a little slower.
Do not be afraid to tell your partner no, or ask them to slow down or even stop. You’re not letting anyone down and you should never feel guilty for having to stop.
Sometimes your body isn’t ready for sex regardless of the amount of preparation you do, and forcing your body to do it could end very messily. Long-term partner or a one-night fling safe sex is always key, whether you choose to wear a condom or go bareback, make sure you get your sexual health checked on a regular basis and know your status.
Be open and honest with the guy you’re having sex with. Hope this little guide helps. Have fun
This week a concerned reader asks about haemorrhoids and whether he can still have sex.
Dear Jose,
I have just found that I have piles… Great! The problem is I’m the bottom in our relationship. Is it safe to f**k whilst I’ve got these? If I use creams and they go away, is there a possibility they’ll burst – am I more likely to get an infection – if say we have a three way or go to an orgy?
J, 40, Somerset.
Dear J
Anal sex has the potential to inflame pre-existing haemorrhoids (piles), though research shows that it does not cause them in the first place. So long as the piles are not actively bleeding or painful at the time on intercourse then it is probably safe to have sex. If they are bleeding or there is inflammation though this means that the natural protective barrier formed by the skin and mucous membranes is not at its optimum which if exposed to a STI can make transmission more likely.
I would recommend using Preparation H or Germoloids to help control pain and inflammation and to reduce swelling. During sex it is also important that you use a good water based lubricant, particularly during acts of multiple person or high frequency sexual activity as this will reduce the chance of any inflammation being caused. They are very unlikely to burst during normal sexual activity, even in the case of sex parties, threesomes or orgies. If creams etc. though do not fix the underlying problem and I would recommend as a permanent solution surgical intervention.
This can now be done almost painlessly by syringing the haemorrhoids and a referral can be obtained by going to see your GP. There are also a number of private clinics undertaking the therapy which do not require GP referral.
This week one reader is concerned about being unclean during sex.
Dear Jose
I’m thinking about bottoming for the first time and I’m a little worried about being “dirty” down there during sex. I’ve heard about certain things you can do to make sure you’re clean and that there’s no sh*t when you’re having sex? Is there anything I can do that’s safe?
Thank you for your advice
Tom, 25 Huddersfield
Dear Tom, Hi there it depends what you mean by dirty. Obviously proper preparation prior to undertaking sexual activity such as anal sex reduces the chances of embarrassing things occurring such as “sh*t dick”.
This can be accomplished by proper douche technique or commercially available enemas.
From a sexual health point of view, any sexual act is broadly safe so long as you or your partners do not have any STIs, id you do have any underlying STIs then get them treated.
The best way to protect against these is to use condoms and to get regularly tested for STIs, at least every 3 months, this testing is available free at NHS sexual health clinics and some Terrence Higgins Trust offices. I would also recommend using condoms with a good water-based lubricant, again these are available free form Terrence Higgins Trust.
Advice by: Jose Perez de la Cruz, BPubHtlth, Public Health Practitioner
If you’ve heard the expression he’s such a white glove bottom and wondered what it is – we have the answer for you.
A white glove bottom is a guy who won’t bottom (be penetrated by another guy) unless he’s completely sure he’s completely clean if you get our drift. So basically he’s the type who will most probably douche or use an enema before penetration to ensure there’s no mess… ever.
Not every man who bottoms is a “white glove bottom” – if you know your body and have a good diet it isn’t always necessary to be excessive with your cleaning.
But if you’re worried about mess, use a condom. These things happen and it’s not the end of the world.
