A crash course on how to give anal pleasure with a strap-on. By Laura LeMoon

A guide to anally topping or pegging a partner with a strap-on, with a focus on communication, how to ease into things, position advice and more, presented in five steps.

How to Have Anal Sex with a Strap-On by Laura LeMoon

Strap In and Strap-On 

Anal sex is one of those things for which none of us is exactly equipped with a roadmap. In fact, in many cis-het relationships specifically, it’s the ‘path less travelled’, something reserved for ‘special occasions’ and – if mainstream porn is anything to go by – usually ‘given’ by a person with a penis and ‘received’ by a person with a pussy or, alternatively, exclusively for gay cis men. Luckily, mainstream porn 

 anything to go by and giving someone anal pleasure no more relies on having a dick than enjoying it means you are submissive, disempowered or somehow demasculinized. The reality is that depending on who you are, what your background and your previous experiences in life, love and sex, you may not bat an eye at a lover’s suggestion of butt play… or you may feel like booty fun is a kind of sexual no man’s land.

The first time I had anal sex I was 18 and really just did it because I felt like I 

 to for my boyfriend at the time, like this was my duty in order to satisfy him sexually. At 27 years old, I tried ‘pegging’ another boyfriend for the first time… Today, as a queer nonbinary person, I enjoy exploring anal play with people of all genders. Anal play is for literally every consenting adult with a butthole – or with a willing butthole to play with. (If you’re reading this, that’s likely even you.) 

So, you’re strapping on your dildo for the first time?

Most anal sex advice tends to stress one thing: lube, lube, lube! But before even that, the most important things as you prepare is communication, communication, communication. Especially if neither yourself or your partner has never really experienced anal sex, you’ll want to make sure to not just speak about boundaries ahead of time, but also talk about nerves. It’s normal to be a little nervous or anxious about anal your first time, or even your second or third, and communicating openly and honestly can go a long way towards helping you ease into things.

Going from zero to 100 is never a good idea, so don’t just dive in there with your biggest dildo.Help your partner relax and loosen up with some stretching exercises beforehand. Kind of like butthole yoga. Whether that means inserting a finger or two (don’t forget that all-important lube) and exploring all the delicious sensations of anal pleasure manually first, or using smaller toys like butt plugs, this can not only help to stretch the area, but can help to ease any anxiety about the experience too. Remember to let your partner set the pace and tell you when they are ready for more.

Letting your partner set the pace is about more than preparing their bodies – be aware of the role of power in (anal) sex. This is especially true if you or your partner is a survivor of trauma. The anus is not like the vagina, and was not made to stretch the way a vagina can and does, so this is oftentimes why, especially if you’re receiving for the first time, there can be pain. All sexual activity has the propensity to cause a survivor of sexual trauma to feel triggered, but with anal sex, because of the mere mechanics of it, it’s important to be aware that someone may have this response. Before you go any further, it can be helpful to check in with your partner (and yourself) – it’s totally okay for them – or you – to ask to stop or take a break at any point, and it doesn’t mean you’re doing it ‘wrong’. Some empowering ways to approach anal would be to choose a dildo together with your partner, to establish a safe word for if you need to stop or slow down, and – of course – to keep checking in.

Saying there’s no ‘wrong’ or ‘right’ way to give anal pleasure isn’t quite correct but 

 what’s right or wrong isn’t something you’re going to learn from reading an article – it’s what you learn from each other. Even so, as you’re preparing to penetrate your partner, it never hurts to start off slow and gentle. For an intimate position that allows your partner to control the speed and depth of penetration, try spooning them from behind (also perfect for whispering romantic words into their ear). A doggy-style position will give you more room to thrust and take charge, while having your partner on top will give them greater power (and you the chance to lay back and enjoy the view) – don’t be afraid to experiment, it’s half the fun.

Note: Keep an eye on your partner’s body language – even if they haven’t said anything, if they tense up or go quiet, you might want to check in to make sure everything is still alright and feels good.

Aftercare for anal is just as important as the anal itself. Some people may want to take a hot bath with epsom salts to ease muscle pain, or perhaps your aftercare is more emotional. Especially if it’s a new experience for you, you may want to decompress and process through writing, music, or talking to a friend. (This is really most critical if you have experienced sexual trauma, or if the experience triggers negative feelings.) Topping someone isn’t about exerting a power trip over another person, unless you’re specifically and consensually engaged in power play. Topping someone anally can give you new insights and perspectives on sex, vulnerability, and intimacy. And these are all areas in which we can, and should, strive to grow as people and as sexual beings.