August anal fingering fun

An enby's hand is held over a wooden table, with a single finger extended.
Photo by Queer and Confused, taken specifically for use in this post!

It’s Anal August, so it’s the perfect month (from a sex-blogger-content point of view!) to explore butt fingering while fucking in a hotel room. Welcome to a super long post about my recent adventures in anal fingering, and why it was a fucking beautiful moment.

In April, I did a week or so of butt plug training (#AnalTrainingApril, I like a hashtag, ok?) before my mental illness meant that putting fingers and silicone toys in my ass had to take a back-seat to other self-care strategies. It was a fun challenge, though, and let me take some really hot photos of my butt – which I could then send to folks who I wanted to flirt with. Asking ‘would you like a photo of my ass filled with a butt plug?’ is an excellent line – in my life, at least – to initiate a some sexting with someone whose cock you’ve already sucked.

Anal sex is brilliant – and not only because it makes brilliant blog content. There’s something filthy about butt sex, something dirty and taboo that gives it an edge that plays into so many of my kinks. Anal sex is hot – it’s the first penetrative sex I ever had, with me fucking my kink partner with my brand new strap-on.

But when it comes to my ass? Psychologically, anal sex is super hot. Physically, it’s a bit hit or miss for me. It’s not because I think it’s dirty, but because physically it’s uncomfortable. Throw down a towel and I’m not too worried about my own shit ending up on my gloved fingers or anal toys. I’m more self-conscious about it with partners, but not much. The first or second time I had sex, the fucking involve a little bit of fingering each other’s butts – using lube but no gloves or condoms. It was fun and playful, and I was very up for the exploration of what it felt like to have something inside me – especially as it was already clear that I wasn’t going to get anything inside my vagina.

Since then it’s been something that I’m into the idea of more than the reality of – which is totally ok! Fantasies can stay as fantasies, my problem is that I want them to be reality, and get frustrated with my own body when I can’t make it do what I feel like it should do. And there’s been times when I’ve done it and it hasn’t been super fun – like when I’d been wanting my play partners to plug me with my sparkly new butt plug all weekend, but when it came down to it my body didn’t want to cooperate.

When I was pushing myself to do more butt stuff in April, I realised that it might be a fear of how much I like it that holds me back. There’s discomfort there – because my body isn’t used to having a chunk of silicone in my ass – but if I pressed a Doxy against my cunt and relaxed my asshole then it was much less uncomfortable. It did hurt as I pushed it past it’s widest point, but in a way that made me feel hungry, like my ass was pulling the plug inside me. That scared me too… so there’s the fear of the pain and discomfort AND the fear of the fact I might really like it (yay for internalised shame about sex!). Butt stuff remained a fantasy, but I stopped pushing my body towards it.

And then I got my ass fingered in a hotel room, and something changed.

It started with spanking – so many good things in my life start with spanking. I was bent over the edge of the bed being spanked – and explaining that yes, they had called me a pain-slut, I don’t like stingy spanks and my pain tolerance in regards to a classic spanking is relatively low. They experimented with thuddier slaps and some butt punches that had me squirming against the sheets.

“Can I eat your ass?”

My fuck yes was instant – I probably should have taken a half-second to remember when I’d last showered and how clean I was there. It was such a hot request that I didn’t care, I just wanted their tongue on me. In me; in my ass. I read a line once that described rimming as somewhere between transcendent and dirty, and I can’t describe it better than that. There’s something inexplicably vulnerable and playful and incredibly hot about feeling someone’s tongue pushing inside your asshole.

When they asked if they could put their finger inside me, I hesitated.

They quickly reassured me that they didn’t need to if I wasn’t down for it. I fumbled for words, trying to explain that it wasn’t that at all. I had paused because while usually I’d say no, I didn’t want to say no to them – not out of a fear of disappointing them, but out of a desire to try it. My eagerness to have something in my ass intrigued me.

I explained this to them, and slowly – careful of my own surprise and arousal – asked if they could do it slowly, with lube from the bottle I’d brought as opposed to their (more practical for a travel-sex kit) sachets and packets. They agreed, and we gave it a go. They can only have been a centimetre or so inside me when I panicked, because it felt uncomfortable and wrong. I told them – my voice probably rising in fear – to stop.

It hurt, but I pushed down the frustration with my body and tried to relax. I was worried that they’d loose interest in me at this point, because fucking me in reality – when I’m naked and messy and potentially going to cry – isn’t as fun as the idea of fucking me. I need to go slow, and I need lots of lube, and I need to try things a couple of times. My kinks are more extreme in my head than what my body can take. When it comes to actual fucking, I promise (or at least worry I do) more than I can deliver.

The fact they were patient and gently stroked my ass while I pulled myself together and asked if we could try again – with more lube. It was still uncomfortable, but I relaxed a little more. They held my hand while I wiggled and fought the uncomfortable heat in my body More lube, and they tried again. I don’t think my cunt was wet any more when we tried for a fourth time, but I stubbornly wanted to keep trying and prove – to them? to myself? – that I could take their finger inside me.

Magically, I was able to give over to the sensations: to submit, in a way I don’t think of myself doing in a physical way often. Apparently my partner could see on my face the moment I surrendered, and they described it as ‘exquisite’. And it felt good. Wrong hot, not wrong my-body-isn’t-working. I could feel their finger moving inside me, and I relaxed into how it felt and grinned in amazement because I liked it. They probably didn’t finger my ass for more than thirty seconds or so, but it felt good – and it felt even better because I’d pushed myself and been vulnerable to get there.

I want more anal fingering in my life soon. I know it’s going to take time – and communication and trust and lube and experimentation – for it to feel good. And I’m ok with that: I just want to submit to the sensation of getting my ass finger-fucked again.

Masturbation Monday is run by the fabulous Kayla Lords. Click on the logo to see what everyone else is getting off to this week.

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White sheets, a red velvet cupcake, and my pink cunt
Dildos for decoration

3 Comments

  1. Awww, this is such a sweet post, which is not something I’d anticipate saying about anal fingering. 🙂

  2. This was such an honest and insightful post. Thank you for sharing your experiences! 😉

  3. I think that struggle is more common than we realize — especially when there is so much content out there that makes anal sound effortless and amazing. I am so glad you had an experience in the right moment with the right person that helped you transcend the uncomfortableness of the feeling. That kind of experience can be really powerful as you move forward, to.

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