I Regret Losing My Virginity to a Sex Worker. Here’s What Happened

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“Yeah, let’s go look at some chicks! I know their usual spot, it’ll be like window shopping, man. See before you buy!”

That’s how it all started. I made a sarcastic joke with David (not his real name), which he clearly missed.

For virgins, we dream of popping our cherries at some point.

The desire to have sex for the first time is alluring, especially for men. They’d rather lose their virginity sooner rather than later.

But my first experience made me sick to the core. It was with a street hooker.

Let’s start from the beginning.


I’m a massive fan of satire and adult humour, especially anything sexual.

A lot of my sick sense of humour came from watching Youtube groups known for making lewd jokes.

So it was common for me to make jokes about sex. I was the guy in the group who didn’t mind overstepping a bit sometimes.

And with David, sexual humour was common banter between us.

So a couple of months ago, David and I were up late chatting at a 24/7-Kopitiam. I told him that after this we should go check out some prostitutes. Just a drive-by.

This part I was serious about.

“Yeah, I always do it when I’m in town,” I exclaimed. Eye-balling women was still a habit for me at the time, and women putting themselves for display was an added bonus.

I told him stories that I made up on the fly, like I was some sort of improv comedian.

“Dude, they are super fine! Also, they’re so easy to get. If you have an itch just do it with them!” I joked, but who would’ve thought that David was taking me seriously.

We got in my car and drove around the streets but they were completely empty, so we headed home instead.

A week later though, after my shift was over I got a call from David.

“Hey, my friend and I wanna check out these hookers again. I really feel like doing it, can you come pick us later?” he asked.

I was sceptical that he would actually go through with this.

“We’ve joked about sex for years, no way is he actually going to hire a prostitute,” I said to myself.

However, he and his friend suddenly asked me to stop by a 7-Eleven to get condoms.

I realized that he was serious. At first, I was shocked, but as he explained I understood his need. ”Dude, I really have developed an urge,” he pleaded.

I started to resent this night and the other night when he took my joke out of context. But I tried to remain supportive of my friend – if this is what he wanted, then I shouldn’t stop him.

I should’ve stopped him.

While I waited for them to go get condoms, I thought, “Ok, he goes in with a woman, and his friend does the same while I wait in the car.”

But when we stopped at the site that the girls were, his friend bailed out. “Oh, they’re too expensive…” he whimpered.

And as if things couldn’t get any worse, David insisted that someone join him in getting a woman. Don’t ask me why.

No one was budging, and we were standing outside this sketchy hotel where cheap-ish, meaningless sex took place. Our situation came to a standstill – neither one of us wanted to buy a hooker with David.

But I’ve known David since the first year of primary school, so I knew he would persist until he got what he wanted.

So in the end, I said “FINE! I’ll do it, I’ll do it. I know you won’t stop insisting on this so let’s just get it over with,” I exclaimed.

We entered the hotel lobby and my stomach twisted itself into knots.

I whispered to David as the hookers were getting the room key, “I hate you! I don’t want this!”, but he didn’t take me seriously and whispered back, “Well it’s happening anyway, man.”

As we made our way to our rooms, a realisation crept in – this is how I’m losing my virginity.

I blanked out.

I became a helpless passenger – I had no control over what was about to happen. It felt like I was just standing on a moving treadmill, heading to a room that smelled like ass, honestly.

When my hooker and I got into the room, she immediately undressed and so did I. It was too late to turn back.

She started off with a handjob, but I couldn’t get hard – there was no chemistry.

That was what it was like having sex with a hooker – you get stiff, you penetrate, you cum, and you’re done.

The handjob wasn’t working and I was still soft, so we laid down on the bed and she sucked my nipple, which disgusted me but actually worked. I started wanking myself and got hard enough.

That’s when it happened.

Things go weird. The intercourse was so passionless so I just had to start a conversation.

“How am I doing?” I asked. Please rate me on a scale of one to ten.

She said I was doing well, and the next best line popped out,

“It’s my first time.”

She giggled in disbelief – wonderful, as if this wasn’t awkward enough, I thought.

After a few more thrusts I told her I was done, but I didn’t actually orgasm, I was just done being here.

We cleaned ourselves off, got dressed and headed out. But before we parted, the lady told me, ”See you soon.”

I simply nodded at her, but under my breath, I said, “Not in a million years.”

When I came out, I felt a mix of emotions – disgust, shame, regret, anger.

“How did I get here?” I asked, looking up into the sky.

I met my friends friend outside.

But when he asked me how was it, I couldn’t contain myself anymore, “I hated it, every single second of it. I enjoyed nothing, I felt nothing. I hate this, I’m just fucking angry,” I scolded in Chinese, David’s friend at a lost for words.

We waited for David, not speaking a word.

David came out probably 20 minutes later, looking satisfied. But I stopped caring about everybody else’s self-interests at the expense of my own self-esteem. I told him off as I did to his friend, ruining what was supposed to be “our fun night out”.

I spent the next half an hour standing in the shower, letting the water rain down on me, hoping that it would wash away all the filth I felt.

When I got into my bed, my penis sunk deep into my body – I couldn’t think about sex the same way anymore.

The next day was my off day, thankfully, and I spent it wallowing in my bed all day. I texted David:

“Look, I need time to process all of this. I didn’t enjoy a single moment of last night and I certainly didn’t want to lose my virginity that way. I led you on with my jokes, not knowing you would take them seriously, and that’s my fault. But right now I just need some space.”

And for the next few days, I didn’t feel like talking to anybody, fearing that I would blurt something I felt embarrassed about. But I eventually did talk to one friend, who had a similar experience, to seek conciliation. It was the first step to getting my life back together again – like a weight had been lifted off my chest.

David and I eventually met up a few weeks ago to clear the air.

“I didn’t know you would take all of my jokes seriously. I’m sorry for inciting this itch you needed to scratch. But I still didn’t want to be dragged into this, but be honest; we would’ve been there for another hour bickering.”

David agreed on the latter statement and apologized too. He told me to try to look on the bright side, though, “You lost your virginity.”

Except that wasn’t sex for me. I would never look at that night rationalizing it for the positives.

I’m still trying to own this experience; that this is how I’ve lost my virginity.

It’s not ideal, but it’s happened and nothing will change that – it’s part of who I am now.

For similar articles, read Losing Your Virginity: Real Stories from Real Malaysians, and I Lost My Virginity to a Call Girl – Should I Tell My Wife-To-Be About It?

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Gregory Wong
An aspiring writer from Kuching. Opinionative, cynical, always hungry (figuratively and literally), and always searching for more meaning in life.
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