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After a long period of lockup, your sub needs to get a release,
No, not an orgasm type of release, he doesn’t need that…
but the semen built up in the prostate over a period of 1-2 weeks can be unhealthy, and can cause issues, the body need to expel the old semen and create new.
fortunately for you, you don’t have to allow him to masturbate, maybe you wont even have to unlock him at all! im talking about the famous ‘Prostate Orgasm’
The idea is stimulating his prostate through his anus so it will encourage the prostate to empty itself, orgasm is not so much the same on this occasion.
If you are completely new to this, i suggest you to explore the ‘anal space’ first, take a lot of lube, slide some fingers in there, with the tip of your finger facing towards the stomach and find the prostate, it is like a bump the size of a walnut, your parthner would be able to tell you when you have found it, oh he will feel the difference.
Massage this nice walnut, massage it sides and surrounding, you can apply some force but be concerned not to push the prostate upwards towards the bladder.
Milking can take anywhere between a few minutes to 40 minutes and even more, so approach this mission with dedication and patience.
Mostly, the first few time or more you will not achieve orgasm purely on massaging the prostate, however you can reach that eventually, the reason for that is that the brain link’s shooting cum to penis stimuli, and now you suggest something completely different, so you need to rewire his brain to accept this new way to get rid of old cum.
One way to go about it is to link the orgasm to the prostate stimulation, at the beginning you will need to provide penis stimulation, and near the point of no return leave it and keep the preasure on the prostate, much like a ruin orgasm, from then on you can drop the penis stimulation earlier and earlier until it’s not necessary for shooting cum, if you choose to go down this path try to emphasis those: always start with anal penetration, the mind will learn to build expectation to it in regards of shooting cum, don’t provide penis or prostate stimulation until the goal is reached, at some point it will be harder for him to orgasm without prostate stimulation, that’s a good step.
Another way is to force it, this method wouldn’t work with everyone, but if you are experienced with anal and like it in general, there is a possibility you can start from a further point, and start massaging for long periods of time, not allowing other types of relief, its possible that by denying orgasm for too long the prostate will be so packed, and the mind so horny, they will just give up and shoot it, pro tip, for the first times if your partner feels really close to cumming, touch his penis or cage gently, or give the head a kiss/ little caress, minimus stimulation, if this will cause him too shoot you are on the right track.
Rewiring the body to prostate orgasm can take many attempts, you can help your chastity locked partner by making him listen to prostate orgasm hypnosis of some kind, , see my post on hypnosis and chastity and make him listen every day over and over, results will show.
If you tried and tried and you feel like you are getting close but not enough, consider getting a prostate toy, prefer something firm over jelly, look for the ones who has a curve that you can aim right at the prostate and of course… strapons are always a good choice.
At the end, remember that every individual is different, some will take a few minutes to achieve anal orgasm, some will take months of attempts and will only shoot after 30 minutes or so.
Be patient, be dedicated, and don’t make this an excuse to get unlocked more often! no!
Enjoy your new only way to achieve orgasm.
Cum Cup October 16, 2018 In "continoues"
‘The Overflow’ October 3, 2018 In "continoues"
‘Release day’ variations February 17, 2019 In "Game ideas"
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May 8, 2022

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Getting into the “zone” for prostate play
If using a vibrating prostate massager
If using Aneros-style prostate sex toys
External prostate stimulation with vibrating toys
Other people’s takes on anal orgasms
What to expect from prostate orgasms
Scientific benefits of milking the prostate gland
Prostate massage troubleshooting – tips if you’re getting nowhere
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Prostate milking is the Holy Grail of male sexuality. If you’re ready, willing, and able, men (and those assigned male at birth!) are able to achieve mind-blowing multiple orgasms without even having to touch their cock at all.
Some men can even cum from anal orgasms alone, with their penis shooting out cum hands-free. It’s quite a spectacle!
However, milking your prostate is no walk in the park, whether you’re doing it alone or with a partner. The benefits and sensations of prostate massage are gargantuan, but getting there requires time, patience, practice, and some new male masturbation techniques.
There are also additional hang-ups for some curious men, such as the stigma around anal play in straight (and some gay!) men, but in this guide, we aim to answer all of your questions about prostate milking techniques, expectations, benefits, tips, and more!
“Prostate milking” or “prostate massage” refers to the stimulation of the male prostate gland. This gland, which is sometimes referred to as the “P-spot” or “male G-spot” is a walnut-sized gland which is located inside the rectum. It’s not very deep into the rectum – it’s only a few inches inside.
The prostate is located between the penis and the bladder. This gland is essential to male sexual functioning, secreting a fluid which helps to protect your sperm. Coincidentally, it is also intrinsically linked to the male orgasm, and prostate massage has to potential to produce incredibly strong orgasms in men.
Using a finger or reputable sex toy, you massage the prostate either internally or externally. Although external prostate stimulation can lead to some pleasurable sensations, internal stimulation is much more intense and enjoyable for most men. Everyone likes different kinds of stimulation; some enjoy the gentlest pressure or muscle contractions, while other men may like to hit their prostate quite hard in order to feel the pleasure. There are a variety of prostate toys available, such as vibrating prostate massagers and hands-free prostate toys.
The pleasure that gay men feel when receiving anal sex is largely due to their prostate gland being stimulated by their partner’s penis inside their ass. There are even some prostate orgasm porn videos of gay men getting fucked with titles such as “hitting his prostate” where the “bottom” partner is seen cumming from anal without any penis stimulation at all. It’s extraordinary. However, this should not deter straight men from taking advantage of the male anal orgasm. At the end of the day, every man is born with a prostate which can be milked for maximum orgasmic pleasure – it’s not something that is exclusive to gay men… they just got lucky! If you want to milk the prostate and achieve otherworldly sexual sensations, you need to let go of the idea that anal orgasms are only for gay men. Even though prostate orgasms concentrate on your anal G-spot, they don’t really “simulate” the feeling of anal sex anyway. In other words, it’s not like having a cock pump in and out of your ass, per se. However, the sensations that it produces within you are similar to that of receiving anal sex, with waves of leg-quivering pleasure radiating throughout your body. Basically, if you want to achieve multiple continuous orgasms and maximize the pleasure that your body can naturally give you, then you’re going to have to get past the idea that prostate milking is “gay”. Have you ever met a gay bottom? They have the best sex in the entire world – they’re getting their prostate stimulated every time they shag. All men should be taking advantage of this natural anal G-spot!
New to putting things inside your ass? Welcome to the world of anal play preparation. It’s not fun and it’s not always easy, but it’s an essential step to take if you want to keep things clean and avoid any nasty surprises.
Even if you’re used to anal play, there are additional steps which are advisable for prostate play, so be sure to give this a thorough read.
Poo comes out of your bottom, as you probably know. Do you know what’s a turn-off for the vast majority of people? Poo. So make sure that your bottom is clean before going up there – it’s not the sort of thing that you just chance.
Because the prostate is only 2-3 inches inside your rectum, you don’t need to go mad with the whole bum cleaning thing. Sometimes your bottom will need less cleaning than others, and other times it may just be a no-go-zone for the night. In time, you’ll get used to knowing when you’re clean enough for prostate play. And at the end of the day, if a little bit of fecal matter does come out, it’s not the end of the world. Put a towel down and get over it – it’s only a little bit of poo.
If you’re attempting to reach anal orgasm by having your (or your partner’s) fingers inside your ass, you should ensure that your fingernails are trimmed and clean. The last thing you want is dirty/pointy fingernails inside the rectum, as this can cause tears and uncomfortable feelings. Also, if you’re not used to it, reaching around inside an ass can be a little strange. For this reason, some people prefer to use a glove or condom as a barrier between the finger and the prostate, helping it to feel a little less weird and direct. As always with anal play, make sure that your finger is adequately lubed up with a high-quality anal lube . Everyone likes different lubes, but water-based and silicone-based lubes tend to be the most recommended for anal play.
If you’re using a reputable prostate toy brand such as Aneros , then the prostate massager toy is going to be shaped so that it ergonomically fits your body, making it easier to insert and feeling quite “natural” once it takes its place.
First, be sure to clean the sex toy with warm soapy water or specialized sex toy wipes before use. Before putting something in your ass, ask yourself “would I be willing the put this in my mouth?” If the answer is no, then you need to clean it. Never put something dirty or dusty inside your bottom.
Before putting something in your ass, ask yourself “would I be willing the put this in my mouth?”
Next, put a towel down on the bed and lay down. Lube the prostate massager up with plenty of water-based lube before insertion. You may want to “warm your anus up” by lubricating your finger and fingering yourself for a few minutes with 1 or 2 fingers. This helps your anus to relax and expand slightly, making more room for the toy.
It’s called a “prostate massage” for a reason – you really need to be in a relaxed and meditative state of mind. I know saying that you need to be in a meditative state sounds all hippie-ish and weird, but believe me when I say that it’s true! Calm your body and your mind, think arousing thoughts, and get yourself excited for one of the best orgasms of your fucking life. This meditative state of mind helps to trigger and stimulate the muscles inside you which are going to give you intense pleasure later on. It’s very hard to describe if you’re not used to these sensations, but it’s almost like you have to get your butt “excited” for this pleasure before it evens happens. The more “excited” your ass is, the more readily it produces anal orgasms.
Also, breathing is really important with many kinds of prostate massage – make sure that you take deep and long breaths, allowing your body to feel all the sensations of the massage as you slowly inhale and exhale your breath. Try to be as mindful as possible with your breathing; it’s an essential part of the process. Practicing mindfulness meditation in your everyday life could actually be a huge help here. Hands free prostate orgasms are not the sort of things that can be achieved in a quick 10 minutes before you catch the train – this is the kind of thing you need to set a couple of hours aside for. Ideally, you want to be home alone (you’ll want to moan loudly) and you’ll want to have 1-2 hours of time without any distractions. If you can plan for 2+ hours of free time, then that’s even better. Don’t rush, as rushing will get you nowhere with this kind of erotic milking.
Looking for those coveted prostate stimulation techniques which produce multiple long orgasms? Then you’re in the right place! Although couples erotic prostate milking can be fun, solo internal prostate stimulation with a high-quality sex toy is the best way to ensure a leg-quivering body-shaking continuous anal orgasm, sometimes referred to as the “Super O” in online prostate milking communities.
If you’ve seen prostate orgasm videos of men rattling around on their beds in pleasure and you want to want to know the best way to achieve prostate orgasm, keep reading.
Although not the best prostate massaging technique, milking the prostate with your finger (or your partner’s finger) could be a good introduction for newbies who are unfamiliar with this kind of anal play. Use a clean and well-lubed up finger, insert it into your rectum around 2-3 inches. You want this finger to be about 2 knuckles deep inside you. You may wish to use your index finger for this, although I find the middle finger to be best personally. The prostate gland is located on the anterior side of your body, so once you’re inside your ass, you want to curve your finger towards the front of your body, almost like you’re moving toward the direction of your penis from inside your ass. With any luck, you’ll feel a walnut-sized “bump” around this area. This is the prostate gland. Use your finger to gently “rub” or “tab” the prostate gland, getting used to the pleasurable sensations that it creates. This kind of prostate stimulation tends to be best accompanied with cock massage and penis masturbation, so try to adopt a position which makes it easy to stroke your cock and jack off while also milking your prostate.
Vibrating prostate toys are a good step up from finger play – they get you accustomed to prostate stimulation and having a male sex toy inside your ass for extended periods of time. You might think that a toy which vibrates would be the “ultimate” pleasure for your prostate gland, but this is not true, as the vibrations tend to “numb” the area over time. Alas, it will feel relaxing at first, but then the numbing effect will take over and the pleasure will become less noticeable. Still, it’s a good middle step for prostate play. After preparing your ass and washing the toy, use a lubed-up finger to loosen up your asshole a little. You need don’t to go too far in – just 2 or 3 inches should do – as we’re just trying to loosen up and relax the anus at this point, making it more ready for a toy to be put inside it. Use 1 or 2 fingers and take a good few minutes to loosen up your ass. When you feel relaxed and open enough, lube up the sex toy with water-based or silicone-based lube and then insert it into your anus with the prostate-stimulating end facing toward the “front” of your body, as if pointing toward the penis. Most manufacturers of these vibrating anal toys will include diagrams which show how their toy is supposed to slide into your rectum, such as this one and this one . Once it’s inserted and your body becomes accustomed to it, simply turn on the vibrations and enjoy! Start soft and work your way up to the bigger pulses – you don’t want to jump in at the deep end. When it comes to prostate masturbation, it’s about the journey rather than the destination! Again, you’re unlikely to experience the Super O anal orgasm from a vibrating toy, so feel free to stimulate your penis and scrotum along with the sensations of the toy.
You really want the best male orgasms that leave your body shaking and legs quivering with pleasure? Then acquaint yourself with the Aneros sex toy range. These sex toys feature patented designs and 100% medical-grade silicone, ensuring an amazing and safe road to your first anal orgasm. Aneros actually make the only medically patented prostate massagers in the world, with their unique design absolutely maximizing anal pleasure for men. The downside? They require practice. Before using Aneros devices, you need to acquaint yourself with your sphincter muscles (the ones you squeeze when pooping) and your PC muscles (the ones which stop you from peeing). The PC muscles (pubococcygeus muscles) are the trickiest to get used to contracting/relaxing, but doing some kegel exercises should help you to strengthen them. These PC muscles are quite subtle and it takes some time to find them, so don’t lose hope. It feels a bit like you’re “pushing out” up to your groin, but everyone describes this feeling differently. Place a towel down and lie in a comfortable position. For the best prostate stimulation results, most people recommend lying on your back with your knees bent up and your feet flat to the floor. Some people also find that lying on their side is pleasurable, especially if they bend their knees up toward their chest. Aneros actually recommend lying on your side and bringing one of your knees up toward your chest as high as you can – this is said to grant the easiest access to the prostate, but may not be the most relaxing or comfortable position. Get your a
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