The First Time

Sex for the first time can be equal parts amazing and appalling. It also involves a lot of ambiguity — should it be openly planned, or should it be silently set up and happen seemingly naturally? CLEO speaks to three women about their first time.

Portrait of Tammy Strobel

Sex for the first time can be equal parts amazing and appalling. It also involves a lot of ambiguity — should it be openly planned, or should it be silently set up and happen seemingly naturally? CLEO speaks to three women about their first time.

My Reading Room

“Regina”, 28, Homemaker

I was 17 and had just entered a polytechnic. He was 18 and in the second year of Junior College. We met while we were both working part-time at a restaurant. I’d noticed him around and we somehow exchanged numbers. I learnt he had a girlfriend who was studying overseas, but I wasn’t looking for a relationship and just wanted to be friends.

I guess he took an interest in me, as he would text me daily and ask to hang out. I didn’t think much of it or show I was into him as he’d always remind me he had a girlfriend, and would talk about her. Soon, he was doing things that a boyfriend would do – walking me home, burning Jay Chou songs onto a CD and even printing out the lyrics and translating them into English. He bought me meals, took me to the movies and even took me for walks along the beach. I was pretty aloof about all his gestures as I didn’t exactly enjoy his company.

He was good-looking, charismatic and smart but would talk a lot about himself. He objectified women, and would talk about his “conquests” and how he loved to “hang them high and dry”. It was clear he was a bad boy. I only hung out with him because he was eye candy. And, of course, I didn’t need to spend any money when we went out.

Eventually, we started making out at staircases near the restaurant we worked at, and we got together soon after and I became his “girlfriend”. He introduced me to his friends. I can’t exactly recall what the arrangement was like, but I wasn’t jealous of his overseas girlfriend and didn’t ask him to break up with her for me. I guess knowing the type of person he was, I never took him seriously. One thing I really liked about him, though, was he was such a good kisser. I loved kissing him.

When my parents had gone away and I had the house to myself, I invited him over as I wanted to take it a step further. I had read quite a bit about sex by then and wanted to do it with him. I wanted to feel what it was like. We engaged in foreplay for a really long time but when he tried to enter me, it hurt and I didn’t want to continue. We tried a few times before giving up, and I saw that he was frustrated as we had been dating for a couple of months by then.

After a while, I decided to try again. We had sex for a really long time, and he left soon after he was done. He sent me a text to remind me to wash up.

We didn’t meet up anymore after that, and soon broke up over text. I was probably just another “conquest”, and I lost my virginity to an attractive albeit sleazy guy.

I met him a few years later at a club and he bought me a drink. I was drunk by then, and decided to follow him back to his place. It was my first time being in his room as he had never invited me over when we were dating. He didn’t finish, and we chatted in bed for a while before I headed home. I remember it was dawn when he walked me down and paid for my cab, and I never saw him again.

I met him a few years later at a club and he bought me a drink. I was drunk by then, and decided to follow him back to his place.”

My Reading Room
“Claudia”, 29, Copywriter
My first time was an accident. I was a late bloomer, and only had my first official boyfriend at the age of 20. He was 22. We met in university. We were both virgins, so neither of us wanted to rush sex. We had made out multiple times in the back of his parents’ car and in the privacy of his room where I would often go over to “study” (and actually study).
During one of those study sessions, we started making out very heatedly, and before we knew it, our clothes were off and caution was thrown out the window. It was lightning fast and over before we knew it, or knew how to stop it. It was a frazzled, harrowing experience as his parents were home. Also, he didn’t have an attached bathroom and I had bled onto his sheets.
Do I regret it? Only that we were not prepared, and so neither condoms nor birth control were used (it’s very important to have condoms because STIs are real and scary). It also put undue pressure on us to stay together because we both took each other’s virginity, and so there was this expectation that we would be each other’s “The One” and would live happily ever after, forever. The relationship ended much later than it should have, and it did not end well.
Thinking back, he was sweet after the deed — as sweet and concerned as any decent boy should be after popping your cherry. But as with all jerks, the niceness ran out once they’ve gotten tired of you. Or start cheating behind your back.
Am I bitter? I can say with confidence: not anymore. I’ve realised I enjoy sex and am quite good at it (verbal confirmation has been obtained), and it wouldn’t have happened without him. Also, he’s taught me to look out for and recognise red flags and warning signs early in a relationship. But as for advice my naggy soon-to-be-30-yearold self would dish out, it’s to always, always, always use protection. And to be prepared. 
My Reading Room

“Tavienya”, 28, Lawyer

It was my first semester in university. There were three of us — him, me and another girl – who were assigned to the same classes. The three of us saw each other a lot, then he and I got grouped together for one of our classes.

During group meetings, we found our eyes meeting more frequently than usual. He asked me out after some weeks. We watched a movie and kissed on the beach on our first date. We dated all through the first and second semester and were each other’s first “real” boy/girlfriend. It was only about a year after meeting that we finally had sex.

We were both virgins. I was 20 and he was 22. Neither of us had much sexual experience before that. Kissing led to other things. Growing up in a very religious household where even having a boyfriend was demonised, I felt guilty. I could say he pushed me further than I had wanted to, but the truth was I wanted him to. We progressed from kissing to the other bases. Sometimes, we made out at the side road near my house; sometimes, in his house when his parents weren’t around; and sometimes, on the beach. We kept finding sand in our pockets for that whole year.

Towards the end of a school break, we took a trip overseas, and planned to have our first time then. We were both quite nervous. We kissed, did some foreplay, and then he put on a condom before sliding inside of me.

It felt like a natural progression from what we had already been doing, and because we were inexperienced, we didn’t know what a female orgasm was so I just sort of participated until he came. Then we fell asleep in each other’s arms.

I expected it to be this huge moment, but the truth is, it didn’t feel particularly mind-blowing. I remember feeling sort of let down, but realised later that it didn’t have to be amazing. Now that I’m much older, I know now that first-time sex is never great. And that’s OK.

About to have sex for the first time?

Clinical sexologist Dr Martha Tara Lee of Eros Coaching tells you how to make the experience more comfortable.

“Look into the date, time and place you want to have sex. You can set up the space so it feels relaxing and romantic to you, if that is what you desire. Do not have expectations about having earth-shattering sex. First-time sex can feel awkward, uncomfortable and even painful. The way to have less painful sex is lots of foreplay for arousal.

I usually encourage my clients to practise fingering for a number of sessions before deciding to have penetrative sex. This way, the focus is on the pleasure and arousal of the person with the vagina, and less on the penetration of the penis (which can be intimidating). The vaginal muscles will have a chance to get used to the sensation of being penetrated and feeling relaxed, and you’ll be less likely to feel that penetration is all about force, pressure and pain.”