The Sex Files: ‘The First Time I Tried Anal Sex’

Memories of the best (and worst) rides of your life.

“Sex with my ex was always pretty… dull. We’d have the same old missionary style sex over and over again and he rarely cared if I came. He’d kiss me for a bit, then have jackhammer style sex with me for a couple of minutes until he came, before rolling over and falling asleep afterwards. It was hardly surprising that I wasn’t feeling satisfied.

His disinterest in pleasing me in the bedroom rolled over into everyday life too, and after about a year of mistreatment I finally decided to end things. I was okay with being single, but I really yearned to be with someone who both treated me right and showed me a damn good time in the sack. That’s when I met Aidan.

Aidan was everything I liked in a man. Tall, confident, charming, but he also had this gorgeous sensitive side about him that I loved as well. He was also, I was pleased to discover, a total devil in bed. We tried everything during our time between the sheets, restraints, nipple clamps, toys, even eating food off each other, but my absolute favourite time with him, was the first time we tried anal.

We had discussed trying it briefly before but the night we finally decided to do it, it was completely spontaneous. I’ll admit, I was nervous on the build up to it. I’d heard horror stories from friends who’d either tried it and didn’t enjoy it, or worse, downright hated it. What if it hurt? I wondered. What if I just didn’t like it? What if I, er, needed to poop? But really, I shouldn’t have worried because Aidan commandeered the whole thing and took control of me in a way that made me feel safe, relaxed and totally aroused.

He started by getting me as turned on as possible, and focused all of his attention on me, kissing from my neck, down to my nipples and eventually on to my clit, skilfully teasing it with his tongue, and by the time we were ready to do the deed I was begging for it and my nerves had dissipated.

We started with him on top of me. He grabbed a little bullet vibrator and placed it on my clit as he pushed into me with the help of a very generous amount of lube. It hurt for just a second and then, ecstasy. I couldn’t believe how turned on I was. Every thrust seemed to make everything feel more sensitive and the thought I was doing something different, adventurous and a little bit taboo turned me on even more. It was even more arousing to see how much he was enjoying it too – he told me afterwards that the tighter fit felt incredible. For me, it was like a sensory overload and I’m pretty sure I came quicker that night than I ever had.

After that, anal was something we incorporated into our sex lives pretty regularly, but our relationship eventually fizzled out. The sex was phenomenal but we realised pretty quickly that our relationship wasn’t based on much else and decided to call it quits. Soon after I met the man I went on to marry. We dabble the odd time in a little butt play, because I trust him more than anyone else in the world, but like losing your virginity, you never forget your first time.”


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