An Anal Sex Guide For First-timers

When I was 16, I had my first taste of anal sex and I must say my first time went HORRIBLY. Not because he was bad, but because I was such a rookie and made things awfully awkward between us. To put things bluntly, I shat all over his bed when he pulled out. Yikes.

But I was lucky because he was extremely understanding and offered to give me a step-by-step of how to douche before anal sex, which I still practise to this very day. 

You need not be a thrill-seeker to enjoy anal sex, and it can definitely spice up your sex life. So, here’s my anal sex guide of what to do before, during and after anal penetration, including some additional tips to help you get the most out of your experience.


1. Be transparent

anal-sex-guide (2)After a good 5 years, I finally learnt the importance of being transparent with what makes the both of you feel good and more importantly, what doesn’t. I’ve been forced into getting tied up and participating in activities that turned the other party on but made me extremely uncomfortable. Remember, you’re not a sex toy!

2. Mental prep part 1

anal-sex-guide (4)Girls, you aren’t going to experience the same sensation as vaginal sex, and your first might even hurt a little. My first was a rather girthy dude, and that was already a struggle on its own. It didn’t help that I wasn’t warmed up yet, so I literally felt my hole splitting apart, maybe even tearing a little. But I soon learnt that there is no use being nervous. Sex should be enjoyable, and taking deep breaths helped prevent my nerves from spiking. 

In the moments leading up to the deed, I find doing things that make me feel confident and sexy a good way to get myself in the mood. I often do stretches, watch porn or read some erotic fanfic. Cleaning and organising my surroundings also helps, especially if I’m hosting.

3. Gather your tools

anal-sex-guide (5)A) Condoms

Protection is unquestionably a must. Chances of having sexual fluids coming into direct contact with an open wound is a lot higher, since your anus is much more delicate than your vag—which means it is more susceptible to tears. 

B) Lube

Lube is as important as condoms, as it prevents the condom from tearing due to friction. I recommend water-based lube as it is the easiest to clean afterwards. It does, however, dry up really quickly, so it is important to have lots of it prepared. While I expect my man to prep all of this, I will always prepare a set as well, so there is no excuse for unprotected penetration.

C) Butt plugs

Butt plugs were really useful when I first started, as it helped make the girthiness much more manageable. Needless to say, my butt plug became my best friend after getting scarred from my virgin experience.

4. Give your ass a good washing

anal-sex-guide (3)This step may not be necessary, because it can get rather uncomfortable but I would highly recommend it if you don’t wanna be like me—a literal shitty mess.

As mentioned previously, the first dude I had anal sex with introduced me to douching—specifically with a shower enema. A shower enema is a douching nozzle that you screw onto your shower hose and can be purchased on various websites including Lazada and Shopee

I find squatting while douching to be the most efficient position. Alternatively, you can prop one leg onto your bathroom sink if you’re flexible enough. Experiment and see what works for you.

  1. Take a deep breath and relax your anal sphincter muscles.
  2. Gently insert the nozzle into your anus. Do not be alarmed if you experience difficulty inserting it on your first try. Try fingering yourself first and applying lube on the nozzle to ease it in.
  3. Start with a steady stream of a comfortable pressure and fill your anus with water for about 5 seconds.
  4. Hold it in for about 30 seconds before squirting it out into your toilet bowl.
  5. Slowly work your way to filling it up longer and holding it longer, ideally 15-20 seconds and 3 whole minutes respectively. It is normal to experience cramping and discomfort along the way, but it is most important to do it at a slow and steady pace.
  6. The pressure of water should be consistent and not too harsh, as it may cause abrasion along your anal lining.
  7. Flush until the water runs clear.

If you’re a rookie, I’d suggest getting a colonic—a professional procedure that uses the injection and removal of water into the colon by a certified doctor. If you lead an active sex life, then I’d recommend doing it at least once a month.

5. Take PrEP

anal-sex-guide (6)This is extremely important. Condoms don’t guarantee full protection, so taking PrEP is vital—regardless of whether you’re at risk of HIV or not. If you’re active, it is necessary to eat PrEP daily, as studies show it can reduce the risk of contracting HIV by up to 92%. You can obtain PrEP from the Be Prepared Clinic at NUH Medical Centre, Tan Tock Seng Hospital as well as the DSC Clinic.

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6. Arousal is key

anal-sex-guide (7)Getting aroused with foreplay, dirty talking and fingering helps me all. the. time. This is also the part where my butt plugs and sex toys come in handy. I used to think that butt plugs were for solo pleasure, but it’s actually really fun and sexy when you use it on each other too. When playing with plugs alone, you know what to expect, but when someone else is in control, it gets crazy. 

My go-to routine: kissing, nipple play, tongueing and rimming the butt, fingering and playing with butt plugs and finally, penetration.

7. Mental prep part 2

anal-sex-guide (8)It’s time. The wiener is about to enter the bun. Take deep breaths and relax as he enters. Start slow and steady before going cray cray. As we already know, it may hurt initially, especially if he packs a tool, but continue taking deep and consistent breaths. Once I got used to the size, the sensation of him hitting my G-spot sent me flying to cloud nine. 

8. Lube, lube, lube

anal-sex-guide (9)As mentioned earlier, water-based lube dries up really quickly, so it is important to keep replenishing generously to keep things gliding smoothly. Thank God I’ve not had any experience of condoms ripping in my ass, thanks to my initiative to keep things lubricated down there.

9. Experiment with various positions for various sensations

  anal-sex-guide (10)Like vaginal intercourse, you can achieve and experience a plethora of sensations with various positions. My personal favourites include the classic doggy style, missionary and cowgirl, as it hits the spot well.


10. Do not douche

anal-sex-guide (11)I used to think it is necessary to douche after anal sex, but I soon realised how big of a mistake that was. Water-based lube has no chemicals and is water-soluble, which means it can be rinsed off with water. Outstanding lube inside will dissolve with the fluids in your colon and naturally be flushed out when you defecate. The pressure of douching may irritate or tear your already-irritated anus further, which may lead to more complications. 

11. Just take a regular shower

anal-sex-guide (12)For some reason, I used to have this irrational fear of turning mouldy on the inside if I were to not wash up as soon as the deal was done, and would always hurry to get cleaned. 

While the anus isn’t a self-cleaning organ like the vagina, there is no need to panic and hit the shower as soon as he pulls out. Take a regular shower and simply wash the rim of your butt with soap and water.

12. Go get checked

anal-sex-guide (13)Once you’ve had your fun, it’s important to go get checked once ASAP to test for STDs and once more about 3 months later, for HIV. Sexual health shouldn’t be taken lightly, so always say yes to safe sex. For a list of anonymous testing clinics in Singapore, refer to this article by the Ministry of Health.

Anal Sex For Dummies

This is my 12-step guide to having anal sex. Obviously, these steps and the order aren’t cast in stone, and I vary things slightly from time to time.

The key is to have fun and practise safe sex always, and every moment will be a blast. Sex should be enjoyable for both parties and you have the right to say no if you’re uncomfortable.

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