One of my favourite comics that I shamelessly repost each Valentine’s Day is this little guy from The Awkward Yeti. It’s Heart, knocked flat out in the boxing ring, bruised and battered and asking Brain for just five minutes to rest before he gets up and tries again. It pretty much encapsulates my entire philosophy on love and relationships. Except that in my case, Vulva would probably be catching her breath right next to Heart as well. 

I’ll dare say though Vulva is in a higher weight class and way tougher than Heart. Given my fair share of long-term relationships and lovers, she always bounces back faster and ready for the next adventure. But Rin, you ask, that doesn’t make sense – how can you claim you’re looking for love yet engage in casual sex with anyone that catches your fancy? 

True, there are schools of thought in dating of waiting for the right person and having your actions align with your true intentions. However, it’s not that I’m able to cast my emotions aside easily (quite the opposite actually), but instead I see owning your pleasure as a natural right one deserves. In other words, sexual pleasure shouldn’t be a scarce treat that you reward yourself only if you think you’re worthy enough. Whether through a lover or a sex toy, in the words of a wise woman named Ariana Grande, “I want it, I got it” when it comes to sexual health.

My attitude towards sex and pleasure wasn’t always as definitive as today. Just like how Miss Grande describe in “Thank you, Next”, I must thank each ex-boyfriend and fling who taught me something new, not just about sex and pleasure but about myself. So in the spirit of World Sexual Health Day with this year’s theme being ‘let’s talk pleasure’, I take a walk through memory lane – or more accurately my Spank Bank records. From being a sexual newbie at 22 to the grand cougar-y age of 38, here are my top 10 lessons on the good, the bad and the sexy I’ve picked up over the years so you can save a few bouts in the sexual experience boxing ring. 

1. Good Sex is Safe Sex 

Let’s start with the most important one – safe sex is good sex, but we’re not just referring to protection. When I first started having sex, being safe meant using condoms during penetrative sex, being on birth control, and going for regular STI check-ups. That’s all true of course and a non-negotiable in your sexual journey to ensure peace of mind. However, the older I get and the more I know myself, the definition of safe sex has also expanded to include physical and emotional safety. 

Physical safety is pretty straightforward but not just reserved for the kinky and BDSM play. While you should be using safe words to denote your comfort level and boundaries during any kink play, you should also be able to tell your partner during regular sex if any positions, thrusting speeds, or body zones are uncomfortable, hurtful or simply no-gos. 

When it comes to having a sexual partner, whether serious or casual, I’ve also learned that having trust, respect and a shared goal of giving and receiving pleasure to each other is the difference between sex that’s just “nice” to “having-random-flashbacks-that-make-you-tingle-down-there”. Feeling emotionally safe is key, especially since sex is such an intimate and vulnerable act, in letting yourself relax when exploring what makes you and your partner tick. 

2.Sex is fun when you make the effort

I used to believe in the magic of spontaneous and romantic grand gestures that lead to mind-blowing sex. Scheduled sex in comparison sounded like such a sad oxymoron! But when you’re juggling work, family and friends, setting aside time and space for sexy dates allows you to be fully in the moment with your partner. That’s the time when both your pleasures are prioritized and the outside world can wait a while during this carnal escape. It also gives you something to look forward to in your calendar as you both get to build up the sexual tension through flirting and sexting. For example, I love the ritual of getting dressed up in beautiful lingerie, dolling up and smelling good for my next date. What’s even more fun is when I’m playing the role of seductress with my partner to see if he’ll like to be spoiled by certain acts or toys for our scheduled rendezvous and vice-versa. 

3. Sex is fun when you take it less seriously 

Yet on the flip side, sex is also more fun the less you take it seriously! While I may bring a treasure trove of toys, deck myself in sexy lace, and plan a list of acrobatic stunts to the bedroom, at the end of the day – all that matters is that we’re both enjoying ourselves without any expectations. That can mean going back to basics, just making out and cuddling, not having penetration, not climaxing, making messes, going limp, becoming dry, the list goes on and on. 

Performative sex is a term that’s used when you’re not actually being in the moment enjoying the pleasurable sensations but instead worrying about how you look, how you’re performing or what’s going to happen next. There’s nothing to be ashamed or guilty about, we’re all humans and it’s no wonder that we worry so much when we’ve put sex on such a pedestal! Movies aren’t going to show how we’ll only last 2 minutes before wiping out from all the squatting, riding, thrusting and needing to clean up and have a snack. Instead I find that the best sex I’ve ever had are with partners where we’re both laughing off the messes, smells, farts and queefs, and taking breaks to catch our literal breaths from positions that just don’t work. So we end up just lying in and chatting as our regular ‘non-sexy’ selves before we go back to being hedonistic beings again. Sometimes those are the memories that I go back to when feeling frisky by myself…

4. Keep an open mind

You’ll often find me referring to sex as ‘play’ and that’s because it’s precisely that. Just like play, sex is also about exploring, being open to new sensations and finding joy in the moments. That’s not to say you can’t have hard limits or personal boundaries when it comes to certain acts in the bedroom. However, when you come across something that you feel resistance to, ask yourself where is this resistance coming from. Is it coming from a place of fear and believing that it’s taboo and doing otherwise you’ll be seen as a slut/deviant in society (e.g. using sex toys, anal sex, pegging,etc)? These are valid concerns of course, especially as the most important aspect is still feeling mentally safe as pointed out earlier. 

However, sometimes fear is also born from ignorance by not researching the options and facts. Instead of immediately shutting down a sexual suggestion, let yourself be curious about it, find out more and have a conversation with your partner. For example, I used to be afraid of choking during sex as I saw it as being too aggressive and possibly going wrong and leading to asphyxiation. I’d explained my fears to my partner and we reached a compromise where he would hold my neck while I have my hand on top of his so I’ll be able to control how tightly he holds. I found out then that feeling the warmth of his gruff hands over my skin and the intensity of the act which required ultimate trust was a huge turn-on and gave me as much pleasure as it did for him. 

5. Check in and communicate

So my story of introducing choking in the pleasure repertoire is the perfect segue into how important is checking in and communication is, especially during sex. I blame it on the movies and romance novels but for some odd reason, the minute the clothes are off, we’re all expected to be mind readers and naturally know where everyone’s hot buttons are. Spoiler alert: It’s easier to ask. 

While it doesn’t have to be a job interview, having a sexy check-in on each other’s expectations and vulnerabilities before sex is something I advocate for, especially when you’re both new to each other. It can be as simple as flirting and asking what their fantasies are, to being direct and asking which sex acts are on the table and which ones aren’t. And even in long-term relationships where you’re used to each other, it always helps to keep the fire going and explore new experiences and sensations together. How do you do that if you’re still shy? You can check out Yes No Maybe lists available online or even play sexy card games like Letz Get Naughty designed to break the ice. 

6. What you do after is just as important

I’m like a broken record when it comes to aftercare post-sex. This is one of the biggest red flags for me in a partner due to my terrible experience the first time I had sex where he pulled off the sheets immediately so he could wash the blood stains while I watched from the bathroom’s doorway feeling absolutely dirty. 

While I’m not expecting a post-coital outpouring of love and cuddles each time, it is important to me that we both decompress and reset together through reassuring words and sharing a drink or snack to replenish our energies. As pointed out in a previous article, it’s natural for the body to crash after sex and suddenly have waves of sadness/loneliness to come over. Just as you’re aware of your own aftercare style, you should also be aware of your partner’s style and respect it. Some of my partners wanted to be alone to deal with the crash so I didn’t take it personally but compromised by a quick kiss and hug, then having words of reassurance later once they’ve settled down. 

7. Toys are tools, not replacements

Call me biased but sex toys are my best friends in the bedroom and I’m not ashamed to admit it. As much as I enjoy feeling my partner inside me and every intimate act together, my anatomy belongs to the 80% of women who can only climax through clitoral stimulation and not penetration-only. When I was younger, I didn’t know what was going on and some partners took it personally that they weren’t satisfying me so they got resentful or gave up. (Yes, I kicked them out of my life…) Ironically it was a partner who noticed it in our sessions and thoughtfully bought me my first vibrating bullet. I came within minutes and was a convert for life. 

In my capacity of being a sex writer and working at Horny.sg, I’ve definitely graduated from your humble bullet vibrator. I’m now privileged to try out a multitude of toys for myself and my partners, including toys for men. I’ve also met a lot of couples and individuals who are new to sex toys in general and it makes me so happy to see people being open to exploring new experiences in the bedroom. It means that while they may initially worry or hesitate to try a sex toy, at the end of the day they’re putting effort into their relationship and partner’s needs, just like my ex did so many years ago. 

8. Flirt & Seduce

It almost sounds too basic to include in a sex list but it’s actually a lesson that took me several years to get comfortable with and now it’s a dealbreaker if my partner doesn’t appreciate the flirting. Growing up, I used to think flirting was a dirty word – good girls don’t flirt, you’re only asking for it if you do. I also had a picture of someone who’s the perfect tease, she’ll be confident, witty and can stride up to any man of her choice and win him over with her coyness. I could never be a femme fatale as I didn’t have the looks or confidence. 

That’s the beauty of flirting though, all it really boils down to is being comfortable in your skin and taking a curious interest in someone else. I flirt through humour and banter (and yes sometimes a flash of the cleavage helps too). What I’ve found out though is it’s about being in the moment with someone and really paying attention to them to what they’re saying and their body language. And what if you’re usually cool in every social situation except when there’s someone attractive nearby? Here’s my secret weapon: if you ever get tongue-tied in front of your crush and feeling awkward, just be honest “Sorry if I’m coming across as a little awkward, I just find you really cute and it’s hard to focus.” Who knows, they might be thinking the same thing! At the very least, you’ve gotten it off your chest and not spiraling in your mind. Worse case scenario? They’ll say ‘thanks but no thanks’ and you’ll sulk for a while and then move on to someone who will adore you. 

9. Forget about gender roles

I had a Latino ex once upon a time and unfortunately he had the stereotypical macho chip on his shoulders. I had to act like the submissive lady while he would be the man who takes charge in the bedroom. One day, while I was on top and lost in the moment of riding, he suddenly blurted out in an actual confused voice “I don’t know if I’m fucking you or you’re fucking me.” I literally froze and looked down, “What does it matter?” in an equally confused tone. He shook his head and said never mind, just continue as it feels good. But the mood was killed and the damage was done. Although it seemed like a small moment to any observer, I already had some insecurities about being on top from a previous partner who voiced out how bad I was at it. I thought I finally figured out the rhythm and was enjoying it after so much pressure on myself. Then that happened and I didn’t ride him anymore for the rest of our relationship. 

As awful as I felt and eventually became a trigger, it does bring up an important lesson in my litmus test for future partners. If a partner is so concerned with traditional gender roles, it’s quite likely they won’t be open to new things like exploring prostate play, sex toys or kinks. It also manifested into being upfront with all future partners and them know that I’m insecure about being on top and to be patient with me when I am. Thankfully, I’ve only dated partners who were nothing but empathetic and didn’t mind the extra practice or new adventures 😉

10. Be kind to yourself and your partner

As you can tell through some of the stories I’ve shared, I’ve had some doozies of terrible partners but thankfully the good ones have made up for it. Which brings me to the final lesson that if you just have one takeaway from this list, it would be this: Be kind to yourself and your partner when it comes to sex and love.

The beauty and bane of coupling up, whether physically for the moment or emotionally in a relationship, is the weight of each other’s histories when both try to create something new together. 

Just like how I had insecurities about being on top and having aftercare, I’ve had partners who worry about their stamina or looks despite me being naked in bed and raring to pounce on them. You’ll never know how it feels for the other person unless you’re a safe space for them as well to confide their vulnerabilities to. So each time you’re feeling down on yourself, remember you’re not alone and that your partner probably has their own fears and insecurities that you can work on together to grow. 

11. (BONUS) Quality trumps quantity

Just like how I like to surprise and indulge my partners, here’s a bonus lesson for you! At the end of the day, being sex positive and advocating for sexual health doesn’t mean you’ve a high libido, have multiple partners, try out every single position from the karma sutra, or have a long history of lovers. It just means you keep yourself informed, empathetic, and prioritize mutual respect, trust, consent and pleasure with your partner/s. It also means you can also decide sex isn’t a priority in your list and that you’re happy as you are. Here’s where I have a confession, the longest I’ve gone without sex was 3 years where I chose to remain celibate as I was in a long distance relationship. Friends were surprised when I’ve shared that little tidbit given how passionate I am about the subject. The truth is, it’s always quality over quantity for me. As long as I feel connected and safe with my partner, I prefer a fun, pleasurable session where we take our time to indulge each other over a quickie just to say we got laid. 

So as we reach the end of the lessons I’ve learned from my 16 years in the sack with exes and lovers, I’m honestly grateful for all of them as they’ve helped shaped the partner and lover I am today. These nuggets of wisdom, both painful and amazing, have also helped to serve as litmus tests for future partners as each person I’ve encountered have brought something new and better to the table each time. At this rate, I can’t wait to find out what new sexual adventures I’ll encounter in the next 16 years 😉

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