Your Fool-Proof, Awks Free Guide To First Time Anal Sex

When it comes to anal sex, there’s a common belief that it can be messy, painful, or uncomfortable. 

But the reality is, done properly, it can be an extremely erotic and exciting activity. If you’re willing to try it, you might find it an unexpectedly fun addition to your sexual repertoire. Read on for the best tips for an enjoyable first time.


This is one of the most common concerns people have when it comes to trying anal penetration, and the truth is, if you start too fast or too large, it can get uncomfortable. However, it definitely doesn’t have to hurt – and there are ways to make it pleasurable, not painful. 


Before getting into the swing of things, make sure that your body is relaxed, and that you’re not feeling tense or nervous. You could also try to help the muscles around your anus relax, too, by squeezing your butt muscles and holding for a few minutes, and then releasing. Anal should be enjoyable experience so, be sure to relax breathe have a glass of wine to calm the nerves if need be. 


To keep anal play comfortable for all partners, make sure that you’re both comfortable communicating about what does and doesn’t feel good. But the number one thing that will keep anal play fun and comfortable is using a good quality anal lubricant, as the anus doesn’t produce its own lubrication in the same way the vagina does. For safe and pleasurable anal adventures, we suggest the Lovehoney Discover Water-Based Anal Lubricant 100ml RRP $12.95 


Be sure to let your partner know that the key here is to be gentle. Many people with penises think the best way to do it is to just dive in; however, no matter how much lube you use, your backdoor is not a water slide. First, you’ll want to ‘warm up’ the anal area by getting it used to the sensations with a finger or a small toy, such as the BASICS Slimline Butt Plug. The Lovehoney Full Bloom Rose Sensual Glass Butt Plug RRP $39.95 is also a great introduction; allowing your partner to gently rub around the opening with the toy, then allow him to experiment by actually inserting the toy (don’t forget the lube!). Then, and only then, should his penis come into play. Start with just the tip and work your way up the shaft.


If you’re concerned about cleanliness and safety (which, to be fair, should be all of us), use a condom! To minimise the risk of infection, be sure to clean your genitals before and after engaging in anal sex. In addition, do not switch between the anus and the vagina during play, as this can lead to some rather unpleasant infections. Make sure that you pick a condom that’s the correct size for you or your partner to keep things safe and comfortable.


Three of the best positions for first-time anal sex include:

Girl-on-top: This position allows the female partner (or person being penetrated) to control speed and depth of penetration, which is extremely important, especially for backdoor newbies.

Doggy-style: This classic allows the person doing the penetrating easy access to the anus, although things can get deep very quickly so do keep things controlled. 

Spooning: This is another great pick for bum-fun beginners. This gives you shared control of your movements and adds an extra touch of intimacy, which may help you relax as well.


Once you’re done with anal sex, it’s important to think about the clean-up, which should be the most important step in your aftercare routine. Wash dirty towels, properly dispose of used condoms or dental dams, and thoroughly wash your toy with the Lovehoney Fresh Toy Cleaner 250ml (RRP $19.95). It can be especially nice to reassure your partner that you enjoyed the experience with them and invite them to have a shower with you for a little extra TLC post-play.

So, anal doesn’t have to be scary! If you’re prepped, comfortable, and equipped with the right mindset and the right tools, you might be surprised to find a world of pleasure waiting for you. 

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