My first prostate massage experience

Ever since I’d discovered prostate pleasure, I’d imagined what it would be like to receive a prostate massage. My first experiences with prostate pleasure with toys – butt plugs and vibrators – had totally transformed my sexuality and shifted my erotic focus from my dick to my prostate. But I knew that being fingered would be a different experience, both physically and emotionally. I wanted to experience that and even started fantasizing about it.

It finally happened one morning when my partner and I were laying in bed in a hotel room in Vegas – which seems kinda appropriate. The day before, she had asked me if I would like her to use one of my prostate toys on me that evening. I said that I’d love that, and I couldn’t stop thinking about it for the rest of the day. That evening we went out and when we got back to the hotel we were tired. But she brought it up again the next morning.

I tried to contain my excitement as I showed her the Lelo Hugo, my go-to vibrator, which I had brought along with me as I usually do on trips. As she held it in her hand, I showed her how the main bulb hit my prostate and the other bulb hit my taint, which made it feel like it was enveloping my prostate. The idea of her controlling the Hugo while it was inside me turned me on. But what I really wanted was to be fingered...

I got naked – she was still wearing clothes, which made me feel even more vulnerable but also somehow made it hotter – and lay on my back. She lay down beside me and started stroking my dick. But within a minute or two, I wanted her to move on to my prostate. That’s how it is when I masturbate too – I start out by stroking my dick, but it’s just foreplay, and pretty quickly I am craving the feeling of prostate stimulation. I gently pulled her hand off my dick and directed it towards my taint.

Looking back, it’s amazing how far I had come. When she had touched my taint before – before I had started exploring prostate pleasure on my own – it made me extremely uncomfortable. I remember she even asked me if I felt violated when she touched me there. I hadn’t yet learned to embrace the vulnerability that comes with prostate pleasure. But now I was ready for it and was totally relaxed with her hand right between my legs. I was kind of proud of myself.

It felt so good when she pressed down on my taint – I even told her she could press harder. At some point – I don’t really remember when – she applied lube to my ass. But I remember I felt like was already on the edge just from external prostate stimulation. It just felt so good. Then I felt her finger right on my hole.

When she finally slid her finger inside me it was an unforgettable moment. Being penetrated with a finger feels very different from a toy – having someone inside you is very different from something. It was just her middle finger, which is much slimmer than toys like the Hugo that I had been using. But it felt much more intense.

To be honest, everything after that is a bit of a blur. I remember feeling her finger slide deeper inside me, which felt incredible, like she was literally opening me up. She quickly found my spot (she told me afterwards that it was easy – exactly like all the guides to prostate massage said, it was 2-3 inches inside and felt harder, like a walnut). Each stroke sent a wave of pleasure through me. I think I was moaning loudly – and saying things like: “Right there.”

It felt so amazing and overwhelming that after a while – I have no idea how long – I told her I needed a break. She started to slowly slide her finger out of me, and I guess she could tell how good it felt when she did that because she said: “Are you sure you want me to stop?” I did and I didn’t. She teased me for a little while, sliding in and out, before she finally slid her finger all the way out of me.

We lay there for a while as I processed it all. It was a totally different feeling than you have after sex when you are the one doing the penetrating – the only way I can express it is that you just feel very open, physically and emotionally. The intimacy of it was like nothing I had ever experienced before – the feeling of having had someone inside you.

I was still recovering when she suddenly slid her finger all the way back in me. She didn’t go slowly like the first time – she just thrust her finger all the way in in one go. It took my breath away all over again. She started fingering me more aggressively than before – instead of laying down beside me, she was now on her knees between my legs – and started varying things up. She slid her finger all the way out, then in again. It was exactly how she liked to be fingered herself (isn't it amazing how G-spot stimulation and P-spot stimulation are so similar?). By now I was thrusting onto her finger with my hips, moving in sync with her.

Those long strokes pretty much blew my mind and I don’t really remember anything after that. After we finished – we didn't even get around to using the Hugo – I was literally speechless. She later told me it seemed like I was “floating” – like, in a totally blissed out state. It was only afterwards that I processed it all and was able to even say anything about it. Even now, I find it hard to put it into words – and the best descriptions I've heard are actually from women.

Sexologist Goody Howard says having your prostate massaged feels “as you though you’re being jacked off from the inside.” That captures exactly how it felt for me – like my partner was deep inside me jacking me off. But even more than the physical pleasure, it was the intimacy: it felt like a deeper connection than I had ever experienced during sex before. After getting fingered for the first time I felt exactly as Layla Martin says guys often feel: “deeply touched inside by the sexual experience”.