Moon is a chastity connoisseur from Vancouver, British Columbia. For the past nine years, he's also had a special passion for hands-free orgasms. Along the way, he's learned as many methods and strategies as possible for achieving this fabled result.
He can be found at @PupMoon3 on Twitter/X and @PupMoon on Bluesky.
By: Moon
For many kinksters, the special season of Locktober and No Nut November is renowned for denial. With these months drawing to a close for 2025, I thought it was the perfect time to write about hands-free orgasms — my favorite way to mix caging with pleasure!
The first time I had a hands-free orgasms was a magical experience. I didn't even know it was possible. I was in a long-distance relationship and would only see my boyfriend on weekends. We had a dom/sub dynamic, and I wasn’t allowed to cum on my own. Not only did this whole situation lead to my love of chastity and denial, but it also led to my first-ever hands-free orgasm, which happened unexpectedly while I was riding my boyfriend during one of our visits together.
These days I talk to a lot of people who don’t think that hands-free or prostate orgasms are achievable for them. However, I believe that with the right technique, and lots of practice, many more people could experience hands-free orgasms.
The mind is a very powerful thing. In the case of wet dreams, your mind can make you orgasm in your sleep, with no external stimulation at all. But the mind can also be a limiting factor when it gets habituated to certain types of stimulation. If this typical kind of stimulation is then lacking, your mind won’t be primed to cum. This can create a self-fulfilling prophecy that makes learning to cum in a new way extremely difficult.
Through a process I call “Gradual Cum Conditioning”, I not only was able to learn for myself, but also have taught dozens of people who didn’t initially believe it was possible.
A Beginner’s Guide to a Hands-free Orgasm
1. Get pent up
The hornier and more pent up you are, the easier a hands-free orgasm will be. I believe this is due to two major factors:
The first is biological — the buildup of seminal fluid in the prostate. While this buildup doesn’t continue indefinitely, it does happen for a period of time after your last orgasm. For some people, this may make your prostate more sensitive to stimulation.
The second is psychological — wanting or needing to cum badly helps your body get all hot and ready for stimulation.
Generally I find that 3-4 days of denial is enough to make a huge difference. If you're having trouble refraining from orgasm, locking yourself (or having someone else lock you) in chastity can make it much easier to achieve this pent up state!
2. Choose the right tools
While it can be extra hot to cum from a toy that really turns you on mentally, like a huge fantasy dildo, the most important thing is being able to put pressure on your prostate.
Time for an anatomy lesson! The prostate is typically only 2 inches inside your rectum. The way I tell people to find it is to insert a finger and point it towards your belly button. Gently apply pressure and rub the wall of your rectum until you feel it. Once you find it, play around a bit, get used to the feeling, and analyze your target.
When choosing a toy, I recommend something hard, not too long, and with a good grip for optimal control and pressure. In my experience glass and metal toys work best, but hard silicone can also get the job done. My personal favorite toy for this purpose is the stainless steel Njoy Pure Wand. [1]
3. Positioning
Generally I recommend one of two positions:
- Lying on your back with your legs in the air. This is comfortable, gives good access to your prostate, and can help you relax – great for beginners!
- Riding a toy. Especially if your toy has a suction cup, you can place it on the floor and ride it. This position takes more effort, but gives a great angle, and allows you to use your body weight to put pressure on your prostate.
If you’re one of the lucky few with access to a fucking machine, it's even easier. Just position the toy so that it hits your prostate with each stroke, lie back, and enjoy.
Regardless of your weapon of choice, the goal is putting rhythmic pressure on your prostate. A general rule of thumb is that you should imagine a line between the entrance of your hole and your belly button. Position your toy so that it follows this line.
A helpful tip to get a good angle when riding a toy is to put your hands behind you and lean back just a bit, rather than going straight up and down. This will help your toy get on the perfect line. As a bonus, it also makes riding a little easier!
Always keep in mind that people's bodies are different, so if these positions don't feel comfortable or pleasurable for you, play around until you find the angle that works best for you and your body.
4. Motion/Technique
No matter the position, the motion you’ll want to use for your first hands-free orgasm is the same. Your goal is to essentially rock the toy over your prostate. Every time you slide the toy past your prostate there will be a sensation of pressure and pleasure. You’ll want to start out with just a slight pressure on your prostate. As you become more comfortable with this motion, you can slowly increase the pressure.
Once you get comfortable, you’ll want to start activating your pelvic floor (the muscle you would use to stop your pee mid-stream) and tense your muscles just a little bit in time with the rocking motion, making sure the peak of the activation and tension is right when the toy is rocking over your prostate. This will add even more pleasure on top of the feeling of your toy penetrating your hole.
Once you get this motion down, you should feel an intense mix of pleasure and pressure on your prostate that grows to a peak with every stroke of your toy and tensing of your muscles. Once you feel that, focus on keeping a steady rhythm. Then it’s time to work on your headspace.
5. Headspace
Some people like to watch porn, listen to hypno files, play with their nipples or balls, or do any number of other things to make themselves desperate with desire. My personal favorite is to find a “Dildo Hero” video or music to set the vibe and turn your riding session into a horny rhythm game.
Others like to relax and try to achieve a sort of flow state. To achieve this, maintain your rhythm but close your eyes. Try to tune out all of the sights and sounds around you, and focus solely on the sensations you are feeling. Allow them to build and come to the front of your mind. Imagine you’re being fucked. Imagine the feeling of an orgasm slowly building. Take yourself back to the last time you came. Imagine how that felt, realize that the sensation you feel now is similar to what you felt then. A feeling in your body that tells you that you need to cum NOW. Let that feeling build, focus on it, become entranced by it. Allow yourself to keep your rhythm, but relax your mind and allow yourself to give in to the feeling. When this is achieved, you will cum without having ever touched your locked cock.
Time to cum
When you cum, stay focused and keep going. Prostate orgasms are very different from normal orgasms. You can ride them for much longer, have multiple orgasms, and keep the pleasure going. What’s important is that you maintain the headspace that got you there in the first place. Tell yourself that this is how you cum now. Allow your body to become used to the feeling of orgasm without touch, and enjoy the feat that you have achieved. Such a good toy cumming in your cage!
Having trouble? Time for Gradual Cum Conditioning.
Gradual Cum Conditioning is a method designed to break through the mental block of hands-free orgasms. For many people, the belief that they cannot or will not cum hands-free is a self-fulfilling prophecy. However, this does not have to be the case.
The basis of this method is creating the ideal conditions to initially make cumming hands-free as easy as possible with additional stimulation and edging, and then gradually work towards needing less and less additional stimulation.
The Gradual Cum Condition Method has three steps:
- Edging
- Pushing over the edge
- Repetition and improvement
1. Edging
Choose one of the methods you normally enjoy for pleasuring yourself and get as close to the edge of orgasm as possible. At the same time that you’re doing this, use your prostate toy and maintain rhythm, but do not go over the edge. Some people like using a vibrator on the outside of their cage – this can be a great option while locked, but please be careful and make sure not to damage your cage!
You could also use ball busting, nipple play, or even sounding for advanced practitioners. If you have difficulty cumming while caged, you could also unlock and edge for this part of the training. Just be extra careful not to lose control and cum during this training phase.
2. Pushing over the edge
Once you’re on the edge of orgasm, stop all stimulation other than the feeling of your toy rocking over your prostate. At this point one of three things will happen:
- If you do not cum, then repeat the edging step and try again. The idea is to get yourself as close as possible, and allow the sensations of your toy to push you over the edge. It may take a few tries, especially for your first time, but eventually there is a good chance you will cum.
- If you cum, but you feel like it was a direct physical result of the edging step, that is totally okay! It takes practice to learn your limit. With this method, some ruined orgasms are bound to happen before you can achieve an elusive hands-free orgasm.
- If you cum from the sensations of your toy pushing you over the edge, congratulations! You’ve beaten level one and can begin the process of leveling up.
3. Repetition and improvement
Practice, Practice, Practice. Rome wasn’t built in a day, and neither was a hands-free orgasm. Make these types of sessions a regular part of your routine. This stage is about conditioning your mind to associate orgasm with the sensations from your prostate toy of choice. Eventually you will work your way up to not needing any additional stimulation.
For optimal results, commit to not cumming any other way while you’re in the middle of the training. Make it the only way you allow yourself to cum. Adding this mindset to the ever-growing feelings of horniness and desperation makes a killer combo when it comes to helping rewire your brain to have explosive hands-free orgasms.
Each time you cum this way, try to gradually extend the time between when you stop edging with the additional stimulation and when you solely use your prostate toy. Set a tangible goal. It can start with as little as 3 seconds between turning off the vibrator and orgasm. Soon this will become 5 seconds, then 10.
Over time you will learn how to be more effective with your toys, how to get into the optimal headspace, and how to overcome the mental block and belief that you cannot cum in your cage. Eventually, you will no longer need the additional stimulation at all. You will be able to cum hands-free like a good locked sub.
Summary
Whether you are able to cum hands-free straight out the gate, or you need to practice for weeks before you’re able to achieve your goal, it is important to remember that everybody's journey is different. Cumming hands-free is not as easy as it seems in porn. However, I truly believe that it is achievable for far more people than you’d think.
I personally used this method to teach myself how to cum hands-free. Now I can do it almost as often as I'd like. In addition, I’ve helped dozens of people who've asked me for advice learn to cum hands-free. Some of these people did it for their very first time after following my process.
The exact techniques that will work for you might vary from person to person. I encourage people to experiment and deviate from this “Guide” as needed. Try different toys, different positions, different methods of edging. Take your time and figure out what is pleasurable for you. Ultimately this process is not meant to be just about achieving some sort of Holy Grail; the fun you have along the way is just as important as the fun you have when you eventually achieve the goal of cumming hands-free.
[1] If you’re new to anal toys, make sure to learn about using anal toys safely before you begin!
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Chastity is a deeply personal journey, and each individual experiences it in their own unique way. The views expressed in this guest post belong solely to the author and do not necessarily reflect those of KINK3D.