
Why didn't we have this conversation earlier? Ladies, let's talk about anal sex.
We’ve all thought about it, or at least been pestered by our partners to “give it a try”. Yet, after a quick Google search (which I don’t advise doing on any traceable computer), the words “Singapore”, “women” and “anal sex” yield more porn sites than actual educational articles.
But it’s 2022! Sex toys are finally mainstream. Now, you can walk into a mother and baby shop to find a wall dedicated to vibrators and more. While I’m finally elated that women are open about their sexual escapades, this is just a step into a whole new world. One with honest sex talk – where it’s safe and normal to ask, “Have you tried anal?” during a casual Sunday brunch with the girls.
Since open conversations start with one person, I’ll be that person. When I told my husband I was interested in getting the word out about anal sex, he lit right up. “Does that mean… for research sake?” he asked, showing infinitely more excitement than when I told him I was pregnant with our first child. Possibly? But first, I had questions.
Let’s go through the basics: Safety first!

A common misconception is that anal sex is “safer” than vaginal sex when it comes to avoiding pregnancy. But, while it’s highly unlikely to happen, semen can leak out of the anus and slide into the vagina. And sperm can live up to five days inside a woman’s body. So it’s plausible that the sperm has enough time to make its way to the cervix and eventually the egg.
“Okay, but that’s still far-fetched.” I hear you. An alternate “ending”: after the man ejaculates in the woman’s anus and doesn’t come crashing down on top of her, they have a couple of last hopeful thrusts in the vagina. This greatly increases the chances of getting pregnant because there might still be semen in the urethra. So if you’re a fertile myrtle, give this last hoorah a miss.
However, what’s likely to happen – immaculate conception aside – is the risk of STIs. I spoke to Dr Michelle Chia, medical director of Ezra Clinic, and she dropped a truth bomb. The risk of contracting STIs or STDs this way may be higher because of poor practices.
“Most likely, women who receive anal sex are doing so unprotected because of the perceived decreased risk of pregnancy,” she says. Sex can start vaginally before moving on to anal. In most cases, it goes back to vaginal sex. Ideally, you’ll want to use a new condom to reduce the risk of transmission of bacteria from the anus to the vagina. But in the heat of the moment, that’s rarely done. Point numero uno: condoms are your best friends during anal sex – even in a monogamous relationship.
So, does it hurt and can you avoid the pain?

Tip: try anal training. It’s the method of learning to relax and expand the anal sphincter. And it’s not always for kinky reasons. Some surgeries that occur in the anal region might need the patient to relearn how to engage that muscle. After giving birth, I had a 4th-degree tear (the worst kind) where I tore my anal sphincter. With all the stitches, haemorrhoids and other things happening to my nether regions, I couldn’t help but clench when it was time to make the first post-birth poo.
I didn’t realise I was doing lightweight anal training at the time: staying calm, relaxed and focusing on the muscle, allowing it to naturally relax, dilate and release. Sounds cliche, but it really is mind over matter, like envisioning a flower opening in slow motion. It works, I tell ya! Try it and thank me next time you’re constipated.
You can also use butt plugs if you don’t have the time to “sit around” and will your butt to open. These can be used anytime before the actual act of sex. Of course, you’re recommended to “ease into it”. Lube up, insert the butt plug gradually and leave it in for increasing periods of time.
Lastly, if condoms are to anal sex what hotdogs are to buns, then lubrication gel is their ketchup. Take note: the type of lubrication matters! Oil-based lubes tend to be a little rougher on the latex of a condom, causing potential rips. Go with water-based gel. Although, ironically, if you’re attempting anal sex in the shower, water isn’t an adequate lubricant and can cause more friction or potential tears. Just relax, lubricate and go slow.
What if things go badly?
Regardless of what you’re into, it’s important to know what infections look like – even if you’re not sexually active. Recognise your regular discharge so you can spot infections early.
After anal sex, do a check down there with your trusty mirror. Michelle says to look out for small things like discomfort or bleeding, abnormal discharge, lumps or bumps around the region. Similarly, symptoms around the vagina also warrant medical attention. Women who engage in receptive anal intercourse should get proper and targeted screenings of the anal canal. There’s also the issue of piles, depending on how severe they are.
“Always have protected intercourse,” she says. “Go for regular STD screenings – this includes getting an anal or rectal swab to screen for STD.”

What about women who’ve recently given birth and want to give their vagina a break? Always wait six to eight weeks for vaginal sex – or until your doctor clears you. However, if you’ve gotten an episiotomy (like myself), depending on the degree of tear, it can take up to a few months for a full recovery. Make sure you check with your doctor and get clearance!
So, will my husband and I give it a shot?
Sadly, no. It all sounds like far too much work for this mother who has two sassy dogs, a fussy baby and a call time of 4am for work. Perhaps anal sex is in my future when my baby finally sleeps through the night. I’ll be on a quiet romantic island with my husband and my butt plugs. It’ll be a meditative retreat where I’ll practice anal training. The drinks (and lubrication) will flow freely. Maybe then, we’ll give it a go.