I’ve been doing so many prostate massage sessions lately that I am having trouble typing as my ‘come hither’ finger is fatigued. It seems the longer the internet is around the more men are discovering prostate play and anal play and wanting to experience ‘the release’ they read about.

From early in my career, I experienced something magical during a fisting and heavy latex session at Salon Kittys. The submissive, completely encased in latex and bondage, would ejaculate water out of his penis when being fucked with a massive dong. I knew he was having an anal orgasm and that that liquid was not urine. However, the session was never replicated with anyone else, so I thought he was just a bit of a blessed saint of the anus. Male squirting is what I always referred to it as, and it occurred when I was pushing a very large dildo inside him at pace. His escalating moans directed me to continue until I felt extreme pressure on the dildo, which, in effect, forced me out of him, allowing this fluid release from his cock. That was in about 2003. My interest in prostate massage has always been driven by this experience and my first-hand knowledge of this, the holy grail of kinky desire. (i.e. pain/pleasure/mess [that isn’t semen]= ultimate depravity)

This anonymous gent has been the subject of many a discussion over the years on anal orgasm and even female ejaculation, as I believe the clear fluid expressed is the same for all genders. The desperation to seek this ejaculation seems the same too. For women, squirting is almost like getting to experience the release of a full male ejaculation. That flush proves that something miraculous has just occurred and seems to reify or embody the essence of desire. Now, I am one of the lucky ones who had a sexual partner so committed to and competent at female pleasure that I experienced squirting for the first time. It was exciting indeed, as it was messy and new, and I felt like I had been welcomed into some advanced orgasm club that I can been denied all my life. But after a while, the ‘female ejaculation’ didn’t really feel like an orgasm of any sort. It was just something different and a nice addition to the experience of sex.

So… back to the present day. I am seeing a lot of gents who feel like they are so close to anal orgasm but just can’t get over the line. And working with these people a lot has come to light. From my experience, there is the anal orgasm (usually with a dildo where the prostate hardens and a contracting/ expanding phenomenon occurs quite like a vaginal orgasm), or the prostate orgasm (Very similar but semen and/or the oblique fluid that no one can confirm oozes out of a soft cock). My expertise lies within the latter, and is often accompanied by a rolling type of orgasm, body shaking etc.  The anal orgasm with dildo sometimes happens very easily and with little commitment. I think some bodies are just designed with more erogenous zones than others, as even beginners can experience this, however (for me) it’s been extremely rare. The prostate orgasm you can work on over time. It helps to do some training to be relaxed to allow for a P-stim vibe to be inserted. (This is good homework for those wanting to pay a professional – I have the Lelo Bruno, which is not cheap but great quality, rechargeable and waterproof).

The point is – we all want our bodies to have more orgasms. We all want to experience the most pleasure life has to give us, however, its not always possible. I’ve had some really great results lately. Just today, a regular experienced a small contracting in his anus, and when I milked his cock it came out white as snow and thick as yoghurt!! Half the fun is manipulating our bodies to get them to experience new things. This is the joy of anal play/ prostate play for me. Sometimes these sessions are completely relaxed, just two people playing and exploring and experimenting together. It’s a sensible thing to do with a professional as it’s so hard to lubricate the anus enough sometimes, and overstimulation stops all anal play in its tracks. It should be mostly pleasure leading to 50% pain/ 50% pleasure, and its time to change play when the scale tips more than that.

Anyway — my current rate for anal orgasm is around 4/10. It’s not very high but its definitely on the rise, and I’m always looking to share skills and learn more to make my practice better. I look forward to hearing about your experiences with anal orgasms in the comments please!

[I thought AI Pembroke gave some great descriptions of the different types of AO in this Quora post here]