Losing Your Virginity

Raised on a diet of rom-coms, we often imagine our first time to be wonderful and romantic. He’d carry you into a candle-lit room, unhook your bra on the first try, and after a few throaty moans, you’d both orgasm at the same time.

But in reality, our first sexual encounters are far what we see in the movies. Clueless virgins and fumbling hands can make for a messy, complicated, or downright awful experience. Discussing how different real life can be from the fantasy we’ve been fed, 9 Singaporean girls describe how they lost their virginity.

*Some names were changed to protect identities

1. “It was awkward and painful”

“The first time I had sex was also the first time I’d been naked in front of a guy. He was my then boyfriend and we were 16. The whole situation was awkward and I was uncomfortable because we were both clueless.

As he rolled on a condom, I remember lying flat on my back, waiting for an impossibly long time. Getting it in was a challenge as well. Tip for first-timers: the vagina is way lower than where you’d think it’d be.

After some fumbling, he managed to find the opening and pushed himself into me. Because I was so nervous, my muscles contracted and it hurt quite a bit.

The sex was lacklustre and disappointing. I thought it’d be magical like in the movies with rainbows and unicorns flying across the sky, but it was meh.”
Bree, 23

2. “I was over-prepared”

“Having been with my boyfriend for a while, I felt ready to have sexual intercourse. However, I was inexperienced and felt anxious about the whole deal. Turning to the internet, I read every thread I could find about losing your virginity.

The night I was to stay over at his place, I remember how I discussed with him exactly how it’d take place. Fully prepared, I spread a towel on the bed and brought out condoms, lube and tissues.

The actual sex was alright I guess, it didn’t hurt but wasn’t anything spectacular. I didn’t orgasm because I wasn’t used to the feeling of having something move in and out repeatedly. Thinking back, it was laughable how overly-prepared I was.”
Lavi, 25

3. “I was raped”

“My first time was an unwanted experience with a guy I’d been seeing for two months. While I’m not against people who have premarital sex, it’s not for me. Despite knowing this, he forced himself onto me, ignoring my protests.

After it happened, I was so confused, upset and guilty. I did enjoy the sex but it felt wrong. Every time I tried bringing up the matter, he would gaslight me.

He’d say my body wouldn’t have reacted the way it did if I didn’t want it. He made the whole incident feel like it was my fault.

Being a victim of rape was a painful experience. Looking back, I know I should’ve just broken up with him immediately. However, I stayed a year in that relationship as a part of me didn’t want my virginity to ‘go to waste’.”
Brandy, 23

4. “It felt like a dildo”

“Back in uni, a close friend and I were having a couple of drinks in hall. We had a ‘thing’ going on and had exchanged more than a few drunken kisses.

He then jokingly offered to show me how good he was in bed. After some consideration, I agreed to sleep with him; I was never a believer in virginity anyway.

I remember feeling let down as it was so anti-climatic. When he pulled out, all I could think about was: “That’s it?!” It felt almost exactly like using a dildo.”
Rhea, 25

Also read:

Vaginismus: How I Managed To Overcome Pain During Sex After 8 Years

5. “I didn’t use protection so kena STD”

“This didn’t happen to me but a girl I know. When she dated her first boyfriend, she was a virgin but he was not, so she looked to him to guide her through the process. Turns out, he was more concerned about his pleasure than safety.

Being impressionable and gullible, she believed when he told her that “you only need to use condoms for casual sex with flings” and “you can’t get pregnant on the first try”. It didn’t occur to her that condoms prevented more than just pregnancies.

Several days later, she developed an intense vaginal itch and a foul-smelling discharge. Turns out, she contracted a urinary tract infection and bacterial vaginosis. Totally not worth it.”
Abi, 23

6. “It made our relationship more intimate”

“I had been dating him for a while and felt it was time to explore the physical side of our relationship.

While kissing and touching each other in bed, he asked if he could touch my vagina with the tip of his penis. It felt pleasurable, and I asked him to put it in. The sex was great and we both managed to orgasm.

While I didn’t feel that my body had changed, I did feel how the relationship had evolved into something more intimate. We had sex, cuddled after, and fell asleep naked together. It was a huge step in the relationship and it brought us closer together.”
Janice, 23

7. “I felt conflicted about sex”

“I was brought up in a staunch Christian family and had been taught to practice abstinence. But during a school exchange programme in Germany, I had sex with a guy I’d been dating for about two months.

It happened painlessly but after we were done, I had a mini existential crisis. I realised sex wasn’t as life-changing as I’d been brought up to believe.

Having had premarital sex changed my perception; sex isn’t bad and it doesn’t make you a bad person.”
Peiying, 24

8. “I pressured my boyfriend and ended up bleeding”

“I’m not proud of it but I pressured my then boyfriend into having sex with me. We’d been seeing each other for little over a year and the furthest we went was experimenting with oral sex and fingering.

I was impatient to lose my virginity. In my group of friends, I was the only one who’d never slept with a guy. I wanted to fit in and to relate to their experiences.

One weekend, when my parents were out of town, I found the perfect opportunity to get frisky. I started bugging him about it until he said yes. He climbed on top of me and went in dry.

Although his ‘package’ was huge, I thought it wouldn’t hurt as much because we’d experimented with fingering. Boy, was I wrong!

There was a sharp pain, which I thought was normal. Gradually, the pain faded to numbness.

I ended up bleeding pretty badly as his dick had caused micro-tears in my vagina. The mess I had to clean up after was not pretty and I’ve not had sex since then.”
Amanda, 26

9. “We ended up laughing”

“The first time I had sex was not a big deal. I went out clubbing with my friends and the guy I was dating. At the end of the night, I told my friends I was going home with him.

Drunkenly, we got into the cab and kissed all the way back to his place. Unfortunately, he got ‘whiskey dick’. No matter how hard he tried, he couldn’t get it up. He ended up putting his half-erect floppy penis into me anyway.

After going at it for a bit, we ended up in a fit of giggles. It wasn’t sexy at all. I blacked out after and woke up to him making breakfast.

While part of me felt disappointed about losing my virginity so carelessly, I was glad that it was with someone I was comfortable with and trusted.”
Grace, 21

It Doesn’t Matter What Age You Lose Your Virginity, Always Have Safe Sex

At the end of the day, having sex is a personal choice. No matter what age you lose your virginity, it should always be done safely and with consent.

This post was first published by Cheryl Chiew on 14 July 2017 and last updated by Nicole Yong on 11 September 2023. 

Also read:

What Would Zula Do: I Lied To My Boyfriend About Being A Virgin