I never thought I'd be the kind of woman who could 'dominate' a man. I'm super awkward, have zero confidence when trying new sex things – I tend to fumble and giggle my way through them like a total idiot – and always take on the submissive role if I'm given half the chance. But, being in a relationship with an open and adventurous person – and getting comfortable with them in private – has gradually warmed me to the idea of taking control.
At first, we started off small, and I'd tie his wrists and ankles to the bed. Then we took things up a notch, and I felt brave enough to blindfold him. While these things may come naturally to some, to me, they felt like little wins and helped me to build up my sexual confidence to where it is today.
While pure terror in the first few moments often rendered me mute, once my worries about screwing it all up and looking like a fool wore away, I started to genuinely enjoy playing a more dominating role. Sometimes you just don't know til you try...
The conversation
Crossing that initial bridge then led us to broadening our sexual horizons in other ways, and as my boyfriend is quite - how to put this - anally curious (he loves anything up there), next-level butt stuff was very much On The Cards. Anal sex had been part of our bedroom routine since we first met, so it wasn't something that felt totally out of my comfort zone. If anything, I was quite experienced in that area. We'd always messed around with butt toys, too - our go-tos being classic anal beads and vibrating butt plugs.
So, perhaps unsurprisingly, when I suggested pegging, his instant answer was, "Yeah, I'm SO up for that."
Pegging, for those who don’t know, is (traditionally) where a woman wears a strap-on dildo to anally penetrate a male partner. While some queer people have taken issue with the terminology (why do we call it "pegging" rather than plain old "anal sex", I wonder?) it's the most widely used word to describe the activity.
The preparation
I'd been kindly sent a beginner's strap-on and harness, and fortunately for us utter novices, the dildo involved was a small 5 inches, very flexible, and not too girthy. As I took it out of the packaging and saw it could fit comfortably in the palm of my hand, I was, rather arrogantly, thinking, 'I could rock that'.
Still, I did feel some nerves ahead of this new sexual adventure. I was also flooded with my usual feelings of self-doubt – Will I actually do it right? What position should we be in? Will I feel like an absolute buffoon when I see myself with a penis? Will he laugh at me?
At the same time, I was trying to balance this desire to have new and enjoyable experiences. Needless to say, that strap-on hung, unworn, on the back of my bedroom door for a full week. Every time I left the room, I saw it swinging there by the harness, gently mocking me. 'Not today Satan,' I'd think. 'I'm not quite ready for whatever you've got in store yet.'
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Then, it all happened one very average Friday night. We'd just got home after a post-work glass of wine, when he said to me straight-up, eyeing the door, "Are you going to put that on and fuck me or what?" Whether it was his cavalier attitude or the large glass of Merlot taking effect, I suddenly felt ready. No nerves, no apprehension, just a 'fuck it' mentality served with a side of excitement.
I'd previously worked myself up about everything, from what outfit would best compliment the strap-on to what other sex acts would be a suitable accompaniment to a good pegging. But like most new sexual experiences, they don't happen like you'd expect them to, and they often come without a warning.
The actual pegging
We made out before I steered him to sit on a chair and sucked his cock until he was just about to come. I very cautiously unhooked the strap-on from the door of shame and slipped my legs into it. Tip for anyone pegging the first time: try that baby on beforehand. Having been helped into it by my colleagues a week before, much to their amusement and horror, I knew what leg to put through which strap. It minimised any potential cringe that could have instantly ruined the moment.
Because it was our first time, I strategically avoided my bedroom mirror - I wasn't quite ready for the sight of myself avec penis - so I asked which position he thought would be most comfortable for him. He laid down on his back, with his knees bent while I positioned myself in between. Not wanting to go straight in there with the strap-on, we fooled around for a bit with A LOT of lube and a small butt plug. And when he was ready, he let me know.
Holding the end of the strap-on, I guided it very slowly into his butt with my hand. But then it hit me that the incredibly obvious thing I didn't consider was that this penis was not my legit anatomy, meaning I wouldn't be able to feel a thing. I wouldn't know how deep I was going or whether I was keeping it at the right angle. At first, there was some very on-brand fumbling and a few "oops, soz" moments from me as I entered him. But once he gave me the nod and said it all felt good and comfortable, I finally relaxed.
During our first pegging session, I thought the best thing to do would be to kind of copy my boyfriend when he's on top. I also made a mental note to think about what I knew felt good to receive in that position. Taking it suuuper slow, I thrusted in and out. And from the look on his face, I knew he didn't want me to stop. Next, I tried leaning back on my heels so I could fully see the strap-on gliding in and out. He let out a low moan and I could feel him moving into me, pulling me closer so I was fucking him deeper. It made me instantly wet.
As I quickened my thrusting, I leant forward, leaving enough room between us for him to gently stroke his penis. At this angle, the harness was rubbing against my clit, and with each forward motion, things just felt more intense. He began masturbating quicker, and harder, and I felt myself nearing the edge of an orgasm. "I’m gonna come," he panted.
Lying there afterwards, I snuggled up to him. It's important to get the aftercare down whenever you try something new, especially something that puts your partner in an incredibly vulnerable position. I made sure to ask him how he found it, how it felt, and if he was okay. But he didn't need to say anything - the dopey post-orgasm grin on his face spoke volumes.
I hadn't come. When he'd said he was close, I instantly became so self-aware that my mind was very much not on my orgasm. But that didn't matter at all. We're all so obsessed with orgasm and often make it the 'end-goal' of sex when really it's the getting there that's the most fun. Putting pressure on ourselves and each other to climax adds unnecessary pressure to what should be a fun and enjoyable experience.
Would I do it again?
Cringe as it sounds, something as intimate as pegging – if you communicate properly and it's consensual – can really make you closer. He was put in a position of extreme vulnerability and trusted me fully to take control. Plus, watching him masturbate as I fucked him was really, really hot...
