I told him it was in the wrong hole – then I found out why

‘No, not there, you did it again.’

I sat up and looked at him. His face was full of confusion and I just couldn’t understand why. I couldn’t stop wondering – throughout the very awkward night – why he was so bad.

‘Um, sorry,’ he mumbled – his face red from both the workout and embarrassment.

I was in the throes of what I was hoping would be passionate sex with Tom (28)*, when I found myself having to calmly guide my one-night stand’s penis to the…right hole.

The last thing I expected when I came home with this cute guy was to teach him how to have sex. But multiple times that night, he kept accidentally inserting his penis into my butt.

It was awkward to say the least. 

It was 2018 and I was fresh out of a serious relationship, and my heart was already too raw to risk any more heartbreak. 

During this time, I found intimacy to be comforting, so eventually downloaded dating apps. I think I found solace being close to someone.

Earlier that same day, I had swiped right on Tom on Hinge because he was cute, and I was horny, and in my eyes, he seemed a good enough lay for that night. 

There wasn’t any deeper intention behind our meeting – a simple ‘hello’ went straight to ‘want to grab a drink tonight?’ with no additional verbal foreplay. 

We organised drinks in a pub, and I made sure it was close to my flat, so we could stumble to mine easily after. He happily agreed, and the unspoken agreement was made – this was a one-night stand of fun, and nothing more.

Silly of me to think, therefore, that he might know what he was doing.

I got to the pub early, and waited with a pint, sipping while eyeing the door. And then, right on cue, two minutes later, he walked in, wearing a big, gorgeous smile.

I decided then that I couldn’t wait to kiss him. 

We drank our pints and laughed about episodes of the TV show Spaced that we were able to quote off by heart, until our words started to slur. We went outside for a rolled-up cigarette and he gently pushed me against the pub wall before kissing me on the lips. 

I smiled, feeling everything inside me burst. This was going to be a great night.

As soon as we finished our drinks, I grabbed his hand and pulled him to the door, eager to be alone with him. We giggled our way to my flat and we were quickly in my room, making out on my bed.

It didn’t take long before our clothes were stripped off and the night was set in motion.

Or so I thought. 

I reached under my bed, pulled out a few condoms and threw them at a tipsy and nonchalant Tom.

I never really trusted men to come prepared, so I made sure I always had condoms with me. I wanted sex, sure – but I also wanted to stay safe. And let’s be honest, those two things don’t always line up – there have been multiple times men have attempted to have unprotected sex with me.

I watched him tear off the packet and attempt to put one on. That’s when I should have realised something was up. He fumbled with the condom, occasionally letting it slip from his hands as he examined it. He poked at the top and mumbled something about it being the right way. 

It slipped from his hand one last time and ended up on the floor. So he reached for another, laughing nervously while I was losing any hope of having sex that night.

‘Sorry,’ he mumbled, ‘I think I’m a bit tipsy,’ before he finally managed to get one on. 

Smiling, he started to crawl towards me, giving me another kiss. Suddenly, I was ready again, and could feel his hand guiding his penis while I was laying on top of him. 

‘Oop!’ I feel him go towards the wrong hole.

‘Sorry,’ he mumbles, realising what he did and trying again.

And then he did it again. And again. That’s when I sat up and looked at him, seeing his confusion and embarrassment. 

‘Let’s try another position,’ I suggested, knowing there could be no mistakes this way – him on top of me in missionary. He obliged, taking orders easily, with no real reaction.

We had very quick and unsatisfying (for me) sex, until he flopped next to me on the bed, happily snoring minutes later. 

Meanwhile, I was left still in bed, looking over at him, wondering what just happened. He finally left on his own accord an hour later, and I immediately told a friend over the phone, who howled with laughter at the story. 

A few weeks later, while scrolling through dating apps looking for another hook-up, I saw a message from Tom – and what I read surprised me. 

‘I didn’t tell you because I was scared, but I was a virgin when I met you.’

A 28-year-old virgin is not too shocking – I knew people who were keeping themselves for marriage, and in many cultures and religions I’m surrounded by, sex is not done for anything other than procreation at the ‘right’ time.

What I was shocked about was that he had not told me. Had he communicated to me that it was his first time, we would have moved more slowly; I would have been gentler and definitely would have helped him understand what to do.

The shame and embarrassment he felt upset me and I wished I could have made his first time a lot nicer.

I politely declined his invite to meet a second time, but told him no hard feelings and hope he has lots of great sex from now on. We left it at that and never communicated again.

But part of me was disappointed that I wasn’t able to give him a great first experience.

If men communicated in bed, I truly believe they would have a better sexual experience every time. They would know what their partner needs, and in turn can explain what they would want to experience. 

It makes me sad that unfortunately for Tom, when he looks back, all he’ll remember was putting it in the wrong hole.

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