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So, You Want to Try Anal Sex… a Beginner’s Guide | the Urban Dater


So, the two of you have decided that you would like to try anal sex. As with trying anything new sexually – or just spicing up what you usually do – communication is the key, so talk about it, understand how you both feel about it. And I would suggest having that conversation when you aren’t about to rip one another’s clothes off, but when you can both focus on the discussion

Personally, I really enjoy anal sex as part of a rich sex life – so my ten top tips are below

I want to be honest with you – yes it can hurt a bit. But if you follow the advice below, the pain should be minimal, and the pleasure can be immense. Personally, I always feel a little pain when my partner enters me anally, but once he is fully in, I love the sensation and it all becomes pleasurable

1. Does it hurt?

I did a little survey among my Twitter followers, close to one hundred women who have tried anal sex responded with their opinion on whether it hurts when he first enters you:
• 26% said they don’t find it painful at all
• 52% (myself included) said they do find it quite painful, but it is worth it
• 10% said they find it painful and struggle to take it
• 12% said they find it too painful, so no thanks

2. You need trust

I find even more trust is required for such an intimate act. And it does feel very intimate which can increase the closeness between you. But I also need to trust that he will stop or pause whenever I need him to and that his key focus is on making this pleasurable for us both. Not just that he has seen a video of anal sex and wants to feel like a porn star

Also, trust includes remembering all the same STI precautions as you would normally

3. Ignore the porn

I think porn can be misleading at the best of times, but I think this is particularly so when it comes to anal sex

Without any foreplay, he gives one big thrust and his cock is fully in her welcoming bottom. Frankly, that would be more likely to have me screaming and running away. Which brings me to my second point…

4. Take it slow

This is really important – and sadly, I think some people are put off because they don’t take it slowly or spend long enough “warming up”

Slow for me means, he pushes the head of the cock against my rear opening and then pauses, gives me a moment to feel him there. I like it when he then pushes just the tip of his cock inside me and again pauses, allowing me to adjust to the sensation. Then again, a little more and pause, let me get used to the stretch – and so forth

Sometimes he can tell from my breathing that he has paused long enough, or if I push back a little, encouraging him to give me a little more. But we will also use that wonderful power of speech! He will ask me if I am okay, I will tell him when I am ready for more

5. Use some lube

Your bottom does not produce natural lubrication in the same way your pussy does, so you need to add some lube (I would suggest a good water-based one). A generous coating of lube on his cock and on your hole will help you both to enjoy the experience much more

With time, you may choose to use less lube. My partner loves the sensation when we don’t use any lube, he enjoys the tightness and the tug on his foreskin – and with experience you may choose to try these things. But to start off with lube, lube, lube and more lube

6. Enjoy some anal foreplay

As with any sex, there is a lot of fun to be had with the foreplay. Firstly, get the mood right, so you both feel aroused. It is also important that she feels relaxed – partly knowing that you will both stop if she isn’t enjoying it, but also entering her will be easier if her muscles relax

A sensual massage with particular attention on her buttocks is a good way to start

A well lubed finger or two can be wonderful stimulation but also help get her warmed up for what is to come

7. Anal toys

Toys are another good idea for foreplay. A small butt plug is a great beginner toy. All the same rules apply – take it slow, use lube – but it can be a great warm up for taking something bigger

Start with some foreplay and then I would recommend lying down on your front on the bed with a pillow under your hips, or on all fours if you prefer. Let him apply a generous amount of lube to you and the toy, and then very slowly and gradually push it inside you

Once it is inside, you may want to roll over onto your back and then the choice is up to the two of you. He might want to use his mouth to pleasure your clit or slide his cock inside your pussy. Either way, the plug inside you should add a wonderful extra dynamic

8. Clit play

On some occasions, I seem to be able to take him anally relatively easily, other times I struggle a bit more. Some clit play really helps when I am struggling. For me, the pleasure on my clit helps me balance any pain

Depending on the position, this could be his fingers playing with my clit or sometimes me using a clit vibe on myself as he enters me. I have been known to “accidentally” forget to remove the clit vibe and just continue enjoying the two wonderful sensations!

9. Is it messy?

I know this is a common concern and generally the answer is no. However, as a lover once said to me on an evening when the sheets were not pristine afterwards “If you play with fire, occasionally you will get burnt” – we both giggled and it stopped me feeling any embarrassment

I think that is the right atmosphere to create. But if you are worried about a little mess, put a towel down that you can clear away afterwards if need be

Alternatively, you can buy an anal douche from most sex toy suppliers and use this beforehand if you want to ensure you are pristine

10. Switching between holes

It is not recommended to switch back from anal sex to vaginal sex – even if everything looks perfectly clean. I heard a wonderful description of the vagina as a “delicate ecosystem” and you don’t want to introduce any unwelcome bacteria into that ecosystem. It can commonly cause urinary tract infections or more complex bacterial infections – all of which are not enjoyable

So, if you want to switch back, ensure he has a quick clean up and if you are using condoms, he pops on a clean one

I hope these tips help you in trying anal sex – following them should help to make it a fun and satisfying experience for you both

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