Discovering Pleasure: A Journey into Anal Fingering and Self-Exploration

Everyone keeps asking me what the first toy should be for anal play. I try to answer their questions after trying to gauge the level of experience they have. After mutual consent to discuss intimate play, I realised that they hadn't made use of the most resourceful tool. The finger. I remember the first time I indulged in anal play. I was with my then partner who was giving me oral sex. They looked up at me and asked if they could finger my ass while they were giving me head. I was confused but I trusted my partner, felt safe and said yes.

So there I was, with a partner prepping their hand with a generous helping of lube and blowing me while slowly fingering my ass and looking up to see if I was okay. How did I feel? Goddamn, was it beautiful. The sensation of the entire act made my toes curl! But was I even supposed to find it beautiful? Did I want anal sex? Imagine one finger making you question your whole sex life. It’s laughable in hindsight, but it’s strange to discover erogenous zones on your body when you’re continuously told that you only get to have one.

Here’s what I wish I had realised at the time— Enjoying the sensation of being fingered didn’t necessarily mean I would like anal penetrative sex. Enjoying the sensation of being fingered didn’t make me a bottom or a submissive. Enjoying the sensation of being fingered didn’t mean I needed toys to elevate that sensation. Now these just happen to be things that were true for me. Of course these observations can end differently for so many people. It's about retaining that curiosity and making sure you go on a journey of self discovery with your body, and not being bullied down a path of what society sees as 'normal pleasure'.

My partner realised from fingering that they enjoyed anal sex through toys and other means. My other partner realised from fingering that the sensation makes them want to poop. There is no button on your body that will ‘change’ who you are. That narrative of fearing what your sexuality might have in store for you, is misguided. Why do we expect all people to think, feel and respond the same way sexually? Everyone else is having fun with their bodies and their pleasure points, so why the hell aren’t we? It makes no sense that we’ve been told by extensive research and multiple sources that our pleasure can and does often lie in or around the prostate and yet, men go out of our way to avoid that very spot.

Men

Receiving anal pleasure through a strap-on apparently makes you ‘less of a man’. Trying anal plugs apparently makes you a cuck? (This confused me greatly when a fellow cis man said these words out loud in a discussion about sex toys). And getting rimmed apparently makes you effeminate or submissive. I’d fuss over these labels some more, but I’m too busy having full body orgasms to fret any longer. Why do cishet men constantly distance themselves from different forms of pleasure? What are they afraid of?

“Looking gay”? What’s …wrong with “looking gay”? What does gay even look like? If you say you’re not gay, you’re just not gay. You are exactly who you believe you are. And on that note, there’s plenty of gay men out there who do not enjoy anal play and define their sexual experiences in a plethora of non-anal ways. What’s your interest or disinterest in anal pleasure got to do with any of them? Or anyone at all?

Women

After speaking to peers who have indulged in anal play, the biggest mistake I observed was that the initiation of anal play always came from the cis male partner. This often led to anal sex which had little to no prep and ends in a lot of pain which then leads to trauma. Even the thought of anal play is struck off their list. They wouldn't even think about exploring it in the safety of their own hands. There has to be a safer start for anal play, and the first and safest step is with your fingers and a lot of lube.

In a survey among cis men and women 89% of those men had performed anal play on a woman, and 79% of women had received it. Only 59% of those men had received anal stimulation from a woman, and only 54% of women had performed it on a man. The most common anal stimulation received was a rim job at 38%. This male fear of penetration is hard to ignore and you know it too. While 82% percent of men in the previous survey were willing to perform anal fingering, only 58% were willing to receive it. When asked for their thoughts on male partners asking for anal play, 9% of the women said that they would react negatively and 59% expressed enthusiasm for it.

Now whether you decide to finger yourself or get fingered or not, no matter how you identify, know that your body is an amazing place just waiting to be explored. Don’t waste opportunities for having mind blowing orgasms, not for ridiculous stereotypes or plain misinformation.

Common Mistakes

Some of the biggest mistakes people make when starting out with anal play is buying the wrong toys and assuming that exploring pleasure for the anal sphincter is all about girth and not depth.

There’s multiple reasons why these assumptions are wrong. Firstly, it leads you to invest good money in a toy or product that your body may not be open to receiving and to make matters worse, you may try the toy and later discover that you do not enjoy anal penetration at all.

Second, it means you are likely to cause injury to a part of your body that actually experience pleasure from internal stimulus and not expansion of the anal sphincter alone.

The easiest and most affordable way to explore if anal penetration is something you enjoy at all, is by starting with a finger.

Your finger or a partner’s finger, but a heavily lubricated one no matter who it belongs to.

Start with the little finger or index finger. Take it slow and see how the sensations and angles make you feel and don’t be afraid to keep adding more lube. If it works and you like it and feel ready for more, graduate slowly to the middle finger for more depth or the thumb for a wider girth.

 

If you feel ready for more, explore a starter toy like the Scorpio. It’s a beaded silicone sleeve with a vibrating bullet inside it. You can insert the beaded end with lube and see how it feels, then click the button on the bullet to experience internal vibrations.

Once you get used to that and still feel like more, shift to the slender Curve. The Curve offers deeper play than the Scorpio and will allow you to explore more vibrations against your prostate or A-spot without testing the limits of your anal sphincter too much.

From there, you can move to the Swirl. The Swirl gives you a little more depth than the Curve while also bringing you the stimulus and beaded feeling of the Scorpio. This will allow you to explore depth, contours and a bit of girth and can really get you to understand what your anal preferences are.

 

It’s only after you complete this journey of slow, safe, tender anal play that you can actually escalate to butt plugs like our silicone Omega series. The Omega comes in Small and Medium sizes, but don’t let that fool you.

Take it one tiny, safe, measured step at a time and make sure that when you tell partners that you enjoy anal play, you have the information you need to guide them on exactly what you like.