I introduced him to pegging – it was a huge mistake

He found out about my strap-on; and his obsession started (Picture: Getty Images/Westend61)

‘Do it again’, said Hugh*, looking up at me with his puppy eyes.

I was standing in my bedroom in my PJs, holding a cup of tea. I’d just asked him whether he wanted to go to sleep or watch a film.

‘What?’ I was confused by his request. ‘Do what again?’

He pointed to the far corner of my bedroom, where my small collection of sex toys sat on my desk chair, alongside the clothes I really needed to fold.

I sighed, finally realising what he meant.

He was pointing to my strap-on – and was yet again, asking me to peg him.

Usually, I wouldn’t have had this somewhat unwilling response. Up until recently, I had loved how much he enjoyed it. But my enjoyment started to disappear when, after introducing Hugh to pegging, he fell head over heels with it and became obsessed.

Suddenly, it had stopped being fun; and had become a chore. 

When I met Hugh, we had very mediocre sex. He would penetrate me, I would go down on him, and sometimes, if I was lucky, he would give me oral. Other than that, I would come sometimes, and he would come often. Like I said: Mediocre.

But as a regular f***buddy, I didn’t want to try and change anything about him. It was all very low-stakes for me.

When I met Hugh, we had very mediocre sex (Picture: Getty Images/Westend61)

Then he found out that, as a bisexual person, I have slept with other women. His interest piqued – if he’d been a puppy, his ears would have shot up. He began asking the typical questions, ones I’ve answered hundreds of times before: how many women had I slept with, did I prefer it, how did we have sex.

That’s how he found out about my strap-on; and without me realising this would be my future, his obsession started.

‘Have you used the strap-on recently?’, he asked me sheepishly, after his tirade of – slightly offensive – questions about my sex life.

‘Not since I’ve been sleeping with you’, I said dismissively; before straightening up and looking at him properly. ‘Although, I could use it on you’.

That night was the beginning of the end of our mediocre sex (Picture: Getty Images/iStockphoto)

I smiled at him when I noticed him smile back. He was definitely curious; in fact, he was into it. He divulged that he had never been pegged before – no one had penetrated him with a strap-on – but he wanted to know what the ‘fuss’ was about (I didn’t have the heart to ask him what ‘fuss’ he was referring to).

That night was the beginning of the end of our mediocre sex.

I had never heard a man make the noises Hugh did – and I was so incredibly turned on that it didn’t take me long to come after, when he gave me oral sex.

We fell on the bed, sweating and out of breath, orgasmic and happy.

Hugh looked over to me and smiled. ‘We should do that more’, he laughed.

And so we did. At first, it was only occasionally – whenever he’d come round and the strap-on happened to be out, he would point at it and smile. Other times, it was tucked in my wardrobe, and I think he felt too shy to ask for it.

Our mediocre sex without the strap-on also got better. He was more passionate, his rhythm changed and he held me firmer. It felt as if the strap-on upskilled him somehow, even though I was the one using it.

I didn’t complain.

Until he started asking to be pegged every time I saw him.

When this happened three times in a row, I realised I wasn’t going to be able to have penetrative sex from him anymore; and that I could no longer expect an orgasm that way. Because he also got into the awful habit of falling asleep as soon as I made him come through penetration.

The issue wasn’t that he wanted to be pegged, it was that he stopped thinking of me and my needs (Picture: Shutterstock / Aloha Hawaii)

The fourth time, we were settling into bed to watch a film – or so I thought – but he asked for it again, pointing to the strap-on on my desk chair.

I had had enough.

‘Are you never going to have sex again? Where I get penetrated?’ I asked, almost sounding whiny. I felt embarrassed for a moment, but stood my ground.

His smile faded. He began to stammer, saying ‘Of course I will’, and ‘It’s not like I ask all the time’; and he randomly told me he’s ‘definitely straight’.

I shrugged. ‘Quite possibly, yeah, but that’s not the problem here, is it?’

I wasn’t going to waste my time on someone who was not going to make me orgasm (Picture: Getty Images)

Standing up, he decided to get offended and claim that I was the one forcing him to get pegged.

‘Yeah, you’re definitely straight’, I scoffed at his display of toxic masculinity. 

The issue wasn’t that he wanted to be pegged, it was that he stopped thinking of me and my needs. And I wasn’t going to waste my time on someone who was not going to make me orgasm.

I picked up my strap-on, pointed the huge rubber penis at him and told him to get out.

After he stormed out, I fell to my bed and laughed. It felt like such an absurd experience, but something I got to tell my friends about nonetheless.

I never saw him again, but I did use my strap-on a lot in the months following.

And every time I did, that person made sure I was also taken care of.

*Name has been changed

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