How to masturbate and orally please a male dog: A guide to oral sex.

Ah yes. It's hard to deprogramme years of learned behaviour.
Would you mind if I ask whether the taste of sperm differs from dog to dog, or for that matter depending on what the dogs diet consists of?
This question is aimed at those of you who actually do this... those who have actual experience of tasting animal sperm and prostate fluid!
Partners (female because I am heterosexual) have commented that my sperm tastes delicious and that experience, in itself, has led me to tasting my own sperm and I cant disagree! Is it my diet or is there a difference from one individual human to another and does this apply to animals? Apparently dog sperm can taste metallic but is that due to the awful diet some of them are given by their humans?
Just curious and, for those people who are prone to humiliating others, look somewhere else if you want to make clever negative comments about this subject
:D
 
Would you mind if I ask whether the taste of sperm differs from dog to dog, or for that matter depending on what the dogs diet consists of?
This question is aimed at those of you who actually do this... those who have actual experience of tasting animal sperm and prostate fluid!
Partners (female because I am heterosexual) have commented that my sperm tastes delicious and that experience, in itself, has led me to tasting my own sperm and I cant disagree! Is it my diet or is there a difference from one individual human to another and does this apply to animals? Apparently dog sperm can taste metallic but is that due to the awful diet some of them are given by their humans?
Just curious and, for those people who are prone to humiliating others, look somewhere else if you want to make clever negative comments about this subject
:D
 
Oral sex it more or less about masturbating a male dog with the added benefit that in the end you do the masturbation with your mouth. So lets begin with how to masturbate a dog.

Castration/neutering:
The purpose of castration is the removal of sexual behavior.
"Another benefit of castration is decreased inappropriate mounting behavior. Mounting can be both a sexual behavior as well as a display of dominance. Neutered males tend to not mount as a sexual behavior because their testosterone levels are much lower than an intact male dog."
(https://www.petcoach.co/article/benefits-of-neutering-castrating-male-dogs-puppies/)
Male dogs without balls do not have the hormones required for a sexual drive. This results in diminishing sexual interest and eventually complete loss of sexual interest. If a dog had sexual experience before being castrated, it is rarely possible that the dog may have some sexual interest after castration. But it will likely diminish over time. The dog will have more trouble keeping an erection, will ejaculate less and the penis may be more dry and require lube.
If a castrated dog is not responding to masturbation, there is no point in trying it any longer.

Age:

1. "Adolescence in dogs marks their sexual maturity, usually between 8 and 12 months."
(https://pmcofedmond.com/pet-education/puppy-dog-vet/dog-stages-of-life/)

2. "When Do Puppies Reach Sexual Maturity?
"The timing of sexual maturity is largely size- and breed-dependent. So, talk to your vet and breeder about your puppy. Sexual maturity in puppies typically begins to occur between 6-to-9 months of age, although certain giant breeds may not reach sexual maturity until they are older."
(https://www.akc.org/expert-advice/health/sexual-maturity-in-puppies-what-to-expect/)

3. "Sexual Maturity. The onset of sexual maturity (puberty) is triggered by hormonal changes that lead to physical and behavioral changes. Generally speaking, puppies will start to mature sexually between 7 and 10 months of age."
(https://www.guidedog.org/PuppyRaising/PuppyRaiserManual/CareAndHealth/Sexual_Maturity.aspx)

Generally speaking you should not attempt to masturbate a dog until he is sexually mature. You should wait for the dog to show sexual behavior like interest in female dogs and mounting/humping.

Training:

Masturbating a male dog:
I am going to describe it based on my dog. Every dog is different and only you know your dog, so you will have to adapt relevant parts to your situation.

Foreplay is the key:
Play with the dog, it is going to get him excited. Ideally the dog should be the one who asks you for sex. This way you have absolute proof of consent. In my case after 5-10 minutes of playing my dog comes to me and pretends to mount my leg. Or if he is too excited he skips the playing and attempts to mount any part of my body immediately. :D
The first time this happened was when he was 6-7 months old and he tried to mount my leg.

You may notice that when your dog is thinking of sex he will actively try to position himself so that his sheath is near or in your hand. Several dogs I have interacted with learned to do this in some way. But when you try to touch the sheath while the dog is not interested in sex, he might growl at you or move away or both. Learn to recognize these signals and do not force it.

Grabbing the sheath and jerking:
When your dog tells you that now is the time grab the sheath so that it rests in your palm and your thumb and index finger is behind the knot. You will feel the knot as a small bulge near the back of the sheath and you will also feel the bone inside the penis. Squeeze the back side of the knot with your fingers, apply gentle pressure on the sheath with your palm and make a few short forward jerking motions.
You will notice that the dog will probably try to thrust forward. Most dogs want something to grab with their front legs onto, so provide your leg or a pillow for example.
At this point the knot will begin to inflate and the dog will ejaculate a few spurts of 1st salty, clear fraction. At the same time the dog will be humping the air or whatever is there. You have to time it right so that you pull the sheath back behind the knot before the knot grows too much but not before it grows at least a little bit. If you miss that, do not force the sheath over the knot, it will hurt. The dog is completely ok with having a full knot inside the sheath, so do not worry.

Keep your hand on the knot and continue applying pressure to it. The knot will grow in your palm and hold the sheath back on it's own. Sometime at this point the dog may ejaculate the sperm rich 2nd fraction which is white and milky and may taste a bit metallic. Though the exact moment of 2nd fraction ejaculation is not precisely defined and may happen later.
When the penis is fully erect the dog will likely want to turn his back to you, so that the penis is pointing back. Let him do it.
At this point the dog will pull on the knot. This is expected. If you have seen any dog mating, the male does pull on the knot. Hold the knot firmly but be cautious. If it looks like the dog really wants to stop and get away, let go of the knot. In this position the dog continues to ejaculate 3rd clear fraction similar to 1st fraction (this may continue for quite a while).

When the excitement wears off the dog will just calmly stand there in a relaxed position, with his mouth slightly open. You will feel the penis pulsing in your hand and you will see the tip twitching. Also you can see the anal contractions.
Keep massaging the knot by periodically squeezing it. I found that squeezing the knot right after you feel a pulse is good.

Have a good look at the penis (It is beautiful, I know :p). If you are lucky and your dog has one of those exceptionally beautiful penises with white shaft, you will easily notice the red tip and red back side of the knot. These parts are the most sensitive and should be stimulated.
Keep your hands off the middle shaft part. Most dogs do not like being touched or rubbed on the shaft.
The tip can be gently stimulated with your fingers but keep it wet. Use only saliva or water based lube. The whole penis should be kept moist because the skin is extremely delicate and easily damaged or uncomfortable if it dries up.
The most sensitive part of the penis is the small twitching end of the pointy tip. You will notice that when you gently rub it, the pulsing in the penis will intensify or resume along with anal contractions and even ejaculation.
NEVER jerk a dog penis like a human penis. It is uncomfortable or even painful for the dog. You are only interested in the knot and the tip.

The oral:
Now with the penis facing back towards you and the dog reasonably calm you can taste it. Take the tip in your mouth and use your tongue to stimulate it.
NEVER touch the penis with your teeth (or any other sharp object) and keep your lips wet.
NEVER suck a dog penis with the up/down motion like a human penis for the same reason as above. This is a dog, they work differently. You may have seen people do it wrong in (commercial) porn, but that was indeed wrong.

Always pay attention to the dog. Dog penis is delicate and can be easily damaged by rough handling.
The dog may want to turn around and lick his own penis a couple of times. Let him do it, you can keep the tip in your mouth while he licks his knot. He is most likely just moistening it up. I have noticed that my dog ejaculates more liquid when he licks himself.
If it happens that you scratch the penis accidentally and there are a few drops of blood, stop what you are doing and give the dog at least a day or two to heal.

If you are doing it right you may notice intense pulsing in the penis, which stops when you stop stimulating the penis or when you do something wrong. Closed or half closed eyes are also generally considered a sign of pleasure along with relaxed facial expression and droopy lips.

The end:
How long a dog will want to have sex depends on how horny he is. At some point the penis will begin to feel colder or begins to deflate. This is a sign for you that the dog will want to stop soon. The dog will become restless and attempt to move away. You must let go of the penis.
My dog has a special body language sign he uses to tell me to stop. Look out for such signals and respect them. It will build trust and clear communication between you two.

Let the dog take care of his penis himself. In most cases the penis deflates completely and goes back into the sheath. If your dog has long hair, you may want to check after a while and remove any hair that might have been pulled into the sheath with the penis.

Some tips for improved experience:
Smell the knot. It has a pleasant smell.
Do some semen collection in a cup, you can enjoy all the taste at once.
Learn headhumping. This means letting your dog mount your head and hump your mouth directly. You will get all the cum, not a single drop is wasted and it is much more fun. But it has to be done carefully and you have to know your dog well so nobody gets hurt.

Have a nice day.
This was simultaneously informative as well as satisfying to picture. Very well written
 
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Oral sex it more or less about masturbating a male dog with the added benefit that in the end you do the masturbation with your mouth. So lets begin with how to masturbate a dog.

Castration/neutering:
The purpose of castration is the removal of sexual behavior.
"Another benefit of castration is decreased inappropriate mounting behavior. Mounting can be both a sexual behavior as well as a display of dominance. Neutered males tend to not mount as a sexual behavior because their testosterone levels are much lower than an intact male dog."
(https://www.petcoach.co/article/benefits-of-neutering-castrating-male-dogs-puppies/)
Male dogs without balls do not have the hormones required for a sexual drive. This results in diminishing sexual interest and eventually complete loss of sexual interest. If a dog had sexual experience before being castrated, it is rarely possible that the dog may have some sexual interest after castration. But it will likely diminish over time. The dog will have more trouble keeping an erection, will ejaculate less and the penis may be more dry and require lube.
If a castrated dog is not responding to masturbation, there is no point in trying it any longer.

Age:

1. "Adolescence in dogs marks their sexual maturity, usually between 8 and 12 months."
(https://pmcofedmond.com/pet-education/puppy-dog-vet/dog-stages-of-life/)

2. "When Do Puppies Reach Sexual Maturity?
"The timing of sexual maturity is largely size- and breed-dependent. So, talk to your vet and breeder about your puppy. Sexual maturity in puppies typically begins to occur between 6-to-9 months of age, although certain giant breeds may not reach sexual maturity until they are older."
(https://www.akc.org/expert-advice/health/sexual-maturity-in-puppies-what-to-expect/)

3. "Sexual Maturity. The onset of sexual maturity (puberty) is triggered by hormonal changes that lead to physical and behavioral changes. Generally speaking, puppies will start to mature sexually between 7 and 10 months of age."
(https://www.guidedog.org/PuppyRaising/PuppyRaiserManual/CareAndHealth/Sexual_Maturity.aspx)

Generally speaking you should not attempt to masturbate a dog until he is sexually mature. You should wait for the dog to show sexual behavior like interest in female dogs and mounting/humping.

Training:

Masturbating a male dog:
I am going to describe it based on my dog. Every dog is different and only you know your dog, so you will have to adapt relevant parts to your situation.

Foreplay is the key:
Play with the dog, it is going to get him excited. Ideally the dog should be the one who asks you for sex. This way you have absolute proof of consent. In my case after 5-10 minutes of playing my dog comes to me and pretends to mount my leg. Or if he is too excited he skips the playing and attempts to mount any part of my body immediately. :D
The first time this happened was when he was 6-7 months old and he tried to mount my leg.

You may notice that when your dog is thinking of sex he will actively try to position himself so that his sheath is near or in your hand. Several dogs I have interacted with learned to do this in some way. But when you try to touch the sheath while the dog is not interested in sex, he might growl at you or move away or both. Learn to recognize these signals and do not force it.

Grabbing the sheath and jerking:
When your dog tells you that now is the time grab the sheath so that it rests in your palm and your thumb and index finger is behind the knot. You will feel the knot as a small bulge near the back of the sheath and you will also feel the bone inside the penis. Squeeze the back side of the knot with your fingers, apply gentle pressure on the sheath with your palm and make a few short forward jerking motions.
You will notice that the dog will probably try to thrust forward. Most dogs want something to grab with their front legs onto, so provide your leg or a pillow for example.
At this point the knot will begin to inflate and the dog will ejaculate a few spurts of 1st salty, clear fraction. At the same time the dog will be humping the air or whatever is there. You have to time it right so that you pull the sheath back behind the knot before the knot grows too much but not before it grows at least a little bit. If you miss that, do not force the sheath over the knot, it will hurt. The dog is completely ok with having a full knot inside the sheath, so do not worry.

Keep your hand on the knot and continue applying pressure to it. The knot will grow in your palm and hold the sheath back on it's own. Sometime at this point the dog may ejaculate the sperm rich 2nd fraction which is white and milky and may taste a bit metallic. Though the exact moment of 2nd fraction ejaculation is not precisely defined and may happen later.
When the penis is fully erect the dog will likely want to turn his back to you, so that the penis is pointing back. Let him do it.
At this point the dog will pull on the knot. This is expected. If you have seen any dog mating, the male does pull on the knot. Hold the knot firmly but be cautious. If it looks like the dog really wants to stop and get away, let go of the knot. In this position the dog continues to ejaculate 3rd clear fraction similar to 1st fraction (this may continue for quite a while).

When the excitement wears off the dog will just calmly stand there in a relaxed position, with his mouth slightly open. You will feel the penis pulsing in your hand and you will see the tip twitching. Also you can see the anal contractions.
Keep massaging the knot by periodically squeezing it. I found that squeezing the knot right after you feel a pulse is good.

Have a good look at the penis (It is beautiful, I know :p). If you are lucky and your dog has one of those exceptionally beautiful penises with white shaft, you will easily notice the red tip and red back side of the knot. These parts are the most sensitive and should be stimulated.
Keep your hands off the middle shaft part. Most dogs do not like being touched or rubbed on the shaft.
The tip can be gently stimulated with your fingers but keep it wet. Use only saliva or water based lube. The whole penis should be kept moist because the skin is extremely delicate and easily damaged or uncomfortable if it dries up.
The most sensitive part of the penis is the small twitching end of the pointy tip. You will notice that when you gently rub it, the pulsing in the penis will intensify or resume along with anal contractions and even ejaculation.
NEVER jerk a dog penis like a human penis. It is uncomfortable or even painful for the dog. You are only interested in the knot and the tip.

The oral:
Now with the penis facing back towards you and the dog reasonably calm you can taste it. Take the tip in your mouth and use your tongue to stimulate it.
NEVER touch the penis with your teeth (or any other sharp object) and keep your lips wet.
NEVER suck a dog penis with the up/down motion like a human penis for the same reason as above. This is a dog, they work differently. You may have seen people do it wrong in (commercial) porn, but that was indeed wrong.

Always pay attention to the dog. Dog penis is delicate and can be easily damaged by rough handling.
The dog may want to turn around and lick his own penis a couple of times. Let him do it, you can keep the tip in your mouth while he licks his knot. He is most likely just moistening it up. I have noticed that my dog ejaculates more liquid when he licks himself.
If it happens that you scratch the penis accidentally and there are a few drops of blood, stop what you are doing and give the dog at least a day or two to heal.

If you are doing it right you may notice intense pulsing in the penis, which stops when you stop stimulating the penis or when you do something wrong. Closed or half closed eyes are also generally considered a sign of pleasure along with relaxed facial expression and droopy lips.

The end:
How long a dog will want to have sex depends on how horny he is. At some point the penis will begin to feel colder or begins to deflate. This is a sign for you that the dog will want to stop soon. The dog will become restless and attempt to move away. You must let go of the penis.
My dog has a special body language sign he uses to tell me to stop. Look out for such signals and respect them. It will build trust and clear communication between you two.

Let the dog take care of his penis himself. In most cases the penis deflates completely and goes back into the sheath. If your dog has long hair, you may want to check after a while and remove any hair that might have been pulled into the sheath with the penis.

Some tips for improved experience:
Smell the knot. It has a pleasant smell.
Do some semen collection in a cup, you can enjoy all the taste at once.
Learn headhumping. This means letting your dog mount your head and hump your mouth directly. You will get all the cum, not a single drop is wasted and it is much more fun. But it has to be done carefully and you have to know your dog well so nobody gets hurt.

Have a nice day.
I've learned a lot from this. Thank you! I want my K9 lovers to enjoy themselves as much as I do, this gives me some excellent ideas on how to do that.
 
  • Like
Reactions: pes
Oral sex it more or less about masturbating a male dog with the added benefit that in the end you do the masturbation with your mouth. So lets begin with how to masturbate a dog.

Castration/neutering:
The purpose of castration is the removal of sexual behavior.
"Another benefit of castration is decreased inappropriate mounting behavior. Mounting can be both a sexual behavior as well as a display of dominance. Neutered males tend to not mount as a sexual behavior because their testosterone levels are much lower than an intact male dog."
(https://www.petcoach.co/article/benefits-of-neutering-castrating-male-dogs-puppies/)
Male dogs without balls do not have the hormones required for a sexual drive. This results in diminishing sexual interest and eventually complete loss of sexual interest. If a dog had sexual experience before being castrated, it is rarely possible that the dog may have some sexual interest after castration. But it will likely diminish over time. The dog will have more trouble keeping an erection, will ejaculate less and the penis may be more dry and require lube.
If a castrated dog is not responding to masturbation, there is no point in trying it any longer.

Age:

1. "Adolescence in dogs marks their sexual maturity, usually between 8 and 12 months."
(https://pmcofedmond.com/pet-education/puppy-dog-vet/dog-stages-of-life/)

2. "When Do Puppies Reach Sexual Maturity?
"The timing of sexual maturity is largely size- and breed-dependent. So, talk to your vet and breeder about your puppy. Sexual maturity in puppies typically begins to occur between 6-to-9 months of age, although certain giant breeds may not reach sexual maturity until they are older."
(https://www.akc.org/expert-advice/health/sexual-maturity-in-puppies-what-to-expect/)

3. "Sexual Maturity. The onset of sexual maturity (puberty) is triggered by hormonal changes that lead to physical and behavioral changes. Generally speaking, puppies will start to mature sexually between 7 and 10 months of age."
(https://www.guidedog.org/PuppyRaising/PuppyRaiserManual/CareAndHealth/Sexual_Maturity.aspx)

Generally speaking you should not attempt to masturbate a dog until he is sexually mature. You should wait for the dog to show sexual behavior like interest in female dogs and mounting/humping.

Training:

Masturbating a male dog:
I am going to describe it based on my dog. Every dog is different and only you know your dog, so you will have to adapt relevant parts to your situation.

Foreplay is the key:
Play with the dog, it is going to get him excited. Ideally the dog should be the one who asks you for sex. This way you have absolute proof of consent. In my case after 5-10 minutes of playing my dog comes to me and pretends to mount my leg. Or if he is too excited he skips the playing and attempts to mount any part of my body immediately. :D
The first time this happened was when he was 6-7 months old and he tried to mount my leg.

You may notice that when your dog is thinking of sex he will actively try to position himself so that his sheath is near or in your hand. Several dogs I have interacted with learned to do this in some way. But when you try to touch the sheath while the dog is not interested in sex, he might growl at you or move away or both. Learn to recognize these signals and do not force it.

Grabbing the sheath and jerking:
When your dog tells you that now is the time grab the sheath so that it rests in your palm and your thumb and index finger is behind the knot. You will feel the knot as a small bulge near the back of the sheath and you will also feel the bone inside the penis. Squeeze the back side of the knot with your fingers, apply gentle pressure on the sheath with your palm and make a few short forward jerking motions.
You will notice that the dog will probably try to thrust forward. Most dogs want something to grab with their front legs onto, so provide your leg or a pillow for example.
At this point the knot will begin to inflate and the dog will ejaculate a few spurts of 1st salty, clear fraction. At the same time the dog will be humping the air or whatever is there. You have to time it right so that you pull the sheath back behind the knot before the knot grows too much but not before it grows at least a little bit. If you miss that, do not force the sheath over the knot, it will hurt. The dog is completely ok with having a full knot inside the sheath, so do not worry.

Keep your hand on the knot and continue applying pressure to it. The knot will grow in your palm and hold the sheath back on it's own. Sometime at this point the dog may ejaculate the sperm rich 2nd fraction which is white and milky and may taste a bit metallic. Though the exact moment of 2nd fraction ejaculation is not precisely defined and may happen later.
When the penis is fully erect the dog will likely want to turn his back to you, so that the penis is pointing back. Let him do it.
At this point the dog will pull on the knot. This is expected. If you have seen any dog mating, the male does pull on the knot. Hold the knot firmly but be cautious. If it looks like the dog really wants to stop and get away, let go of the knot. In this position the dog continues to ejaculate 3rd clear fraction similar to 1st fraction (this may continue for quite a while).

When the excitement wears off the dog will just calmly stand there in a relaxed position, with his mouth slightly open. You will feel the penis pulsing in your hand and you will see the tip twitching. Also you can see the anal contractions.
Keep massaging the knot by periodically squeezing it. I found that squeezing the knot right after you feel a pulse is good.

Have a good look at the penis (It is beautiful, I know :p). If you are lucky and your dog has one of those exceptionally beautiful penises with white shaft, you will easily notice the red tip and red back side of the knot. These parts are the most sensitive and should be stimulated.
Keep your hands off the middle shaft part. Most dogs do not like being touched or rubbed on the shaft.
The tip can be gently stimulated with your fingers but keep it wet. Use only saliva or water based lube. The whole penis should be kept moist because the skin is extremely delicate and easily damaged or uncomfortable if it dries up.
The most sensitive part of the penis is the small twitching end of the pointy tip. You will notice that when you gently rub it, the pulsing in the penis will intensify or resume along with anal contractions and even ejaculation.
NEVER jerk a dog penis like a human penis. It is uncomfortable or even painful for the dog. You are only interested in the knot and the tip.

The oral:
Now with the penis facing back towards you and the dog reasonably calm you can taste it. Take the tip in your mouth and use your tongue to stimulate it.
NEVER touch the penis with your teeth (or any other sharp object) and keep your lips wet.
NEVER suck a dog penis with the up/down motion like a human penis for the same reason as above. This is a dog, they work differently. You may have seen people do it wrong in (commercial) porn, but that was indeed wrong.

Always pay attention to the dog. Dog penis is delicate and can be easily damaged by rough handling.
The dog may want to turn around and lick his own penis a couple of times. Let him do it, you can keep the tip in your mouth while he licks his knot. He is most likely just moistening it up. I have noticed that my dog ejaculates more liquid when he licks himself.
If it happens that you scratch the penis accidentally and there are a few drops of blood, stop what you are doing and give the dog at least a day or two to heal.

If you are doing it right you may notice intense pulsing in the penis, which stops when you stop stimulating the penis or when you do something wrong. Closed or half closed eyes are also generally considered a sign of pleasure along with relaxed facial expression and droopy lips.

The end:
How long a dog will want to have sex depends on how horny he is. At some point the penis will begin to feel colder or begins to deflate. This is a sign for you that the dog will want to stop soon. The dog will become restless and attempt to move away. You must let go of the penis.
My dog has a special body language sign he uses to tell me to stop. Look out for such signals and respect them. It will build trust and clear communication between you two.

Let the dog take care of his penis himself. In most cases the penis deflates completely and goes back into the sheath. If your dog has long hair, you may want to check after a while and remove any hair that might have been pulled into the sheath with the penis.

Some tips for improved experience:
Smell the knot. It has a pleasant smell.
Do some semen collection in a cup, you can enjoy all the taste at once.
Learn headhumping. This means letting your dog mount your head and hump your mouth directly. You will get all the cum, not a single drop is wasted and it is much more fun. But it has to be done carefully and you have to know your dog well so nobody gets hurt.

Have a nice day.

damn. This got me hard just reading and I have precum running down my shaft! Very good reading!
 
so.... to do oral with a male dog, I cover my teeth with my lips, and lick the tip like in a french kiss?
What I've noticed that works really well, is puckering your lips a little bit and latching onto his tip. And I mean JUST the tip, then apply suction and stimulate with your tongue. The very tip usually comes to a small point like a triangle, just cover this part with your lips and youll feel him pump like crazy. Also, keep one hand at the base of his knot and apply a small amount of pressure. Hope this helps!
 
Oral sex it more or less about masturbating a male dog with the added benefit that in the end you do the masturbation with your mouth. So lets begin with how to masturbate a dog.

Castration/neutering:
The purpose of castration is the removal of sexual behavior.
"Another benefit of castration is decreased inappropriate mounting behavior. Mounting can be both a sexual behavior as well as a display of dominance. Neutered males tend to not mount as a sexual behavior because their testosterone levels are much lower than an intact male dog."
(https://www.petcoach.co/article/benefits-of-neutering-castrating-male-dogs-puppies/)
Male dogs without balls do not have the hormones required for a sexual drive. This results in diminishing sexual interest and eventually complete loss of sexual interest. If a dog had sexual experience before being castrated, it is rarely possible that the dog may have some sexual interest after castration. But it will likely diminish over time. The dog will have more trouble keeping an erection, will ejaculate less and the penis may be more dry and require lube.
If a castrated dog is not responding to masturbation, there is no point in trying it any longer.

Age:

1. "Adolescence in dogs marks their sexual maturity, usually between 8 and 12 months."
(https://pmcofedmond.com/pet-education/puppy-dog-vet/dog-stages-of-life/)

2. "When Do Puppies Reach Sexual Maturity?
"The timing of sexual maturity is largely size- and breed-dependent. So, talk to your vet and breeder about your puppy. Sexual maturity in puppies typically begins to occur between 6-to-9 months of age, although certain giant breeds may not reach sexual maturity until they are older."
(https://www.akc.org/expert-advice/health/sexual-maturity-in-puppies-what-to-expect/)

3. "Sexual Maturity. The onset of sexual maturity (puberty) is triggered by hormonal changes that lead to physical and behavioral changes. Generally speaking, puppies will start to mature sexually between 7 and 10 months of age."
(https://www.guidedog.org/PuppyRaising/PuppyRaiserManual/CareAndHealth/Sexual_Maturity.aspx)

Generally speaking you should not attempt to masturbate a dog until he is sexually mature. You should wait for the dog to show sexual behavior like interest in female dogs and mounting/humping.

Training:

Masturbating a male dog:
I am going to describe it based on my dog. Every dog is different and only you know your dog, so you will have to adapt relevant parts to your situation.

Foreplay is the key:
Play with the dog, it is going to get him excited. Ideally the dog should be the one who asks you for sex. This way you have absolute proof of consent. In my case after 5-10 minutes of playing my dog comes to me and pretends to mount my leg. Or if he is too excited he skips the playing and attempts to mount any part of my body immediately. :D
The first time this happened was when he was 6-7 months old and he tried to mount my leg.

You may notice that when your dog is thinking of sex he will actively try to position himself so that his sheath is near or in your hand. Several dogs I have interacted with learned to do this in some way. But when you try to touch the sheath while the dog is not interested in sex, he might growl at you or move away or both. Learn to recognize these signals and do not force it.

Grabbing the sheath and jerking:
When your dog tells you that now is the time grab the sheath so that it rests in your palm and your thumb and index finger is behind the knot. You will feel the knot as a small bulge near the back of the sheath and you will also feel the bone inside the penis. Squeeze the back side of the knot with your fingers, apply gentle pressure on the sheath with your palm and make a few short forward jerking motions.
You will notice that the dog will probably try to thrust forward. Most dogs want something to grab with their front legs onto, so provide your leg or a pillow for example.
At this point the knot will begin to inflate and the dog will ejaculate a few spurts of 1st salty, clear fraction. At the same time the dog will be humping the air or whatever is there. You have to time it right so that you pull the sheath back behind the knot before the knot grows too much but not before it grows at least a little bit. If you miss that, do not force the sheath over the knot, it will hurt. The dog is completely ok with having a full knot inside the sheath, so do not worry.

Keep your hand on the knot and continue applying pressure to it. The knot will grow in your palm and hold the sheath back on it's own. Sometime at this point the dog may ejaculate the sperm rich 2nd fraction which is white and milky and may taste a bit metallic. Though the exact moment of 2nd fraction ejaculation is not precisely defined and may happen later.
When the penis is fully erect the dog will likely want to turn his back to you, so that the penis is pointing back. Let him do it.
At this point the dog will pull on the knot. This is expected. If you have seen any dog mating, the male does pull on the knot. Hold the knot firmly but be cautious. If it looks like the dog really wants to stop and get away, let go of the knot. In this position the dog continues to ejaculate 3rd clear fraction similar to 1st fraction (this may continue for quite a while).

When the excitement wears off the dog will just calmly stand there in a relaxed position, with his mouth slightly open. You will feel the penis pulsing in your hand and you will see the tip twitching. Also you can see the anal contractions.
Keep massaging the knot by periodically squeezing it. I found that squeezing the knot right after you feel a pulse is good.

Have a good look at the penis (It is beautiful, I know :p). If you are lucky and your dog has one of those exceptionally beautiful penises with white shaft, you will easily notice the red tip and red back side of the knot. These parts are the most sensitive and should be stimulated.
Keep your hands off the middle shaft part. Most dogs do not like being touched or rubbed on the shaft.
The tip can be gently stimulated with your fingers but keep it wet. Use only saliva or water based lube. The whole penis should be kept moist because the skin is extremely delicate and easily damaged or uncomfortable if it dries up.
The most sensitive part of the penis is the small twitching end of the pointy tip. You will notice that when you gently rub it, the pulsing in the penis will intensify or resume along with anal contractions and even ejaculation.
NEVER jerk a dog penis like a human penis. It is uncomfortable or even painful for the dog. You are only interested in the knot and the tip.

The oral:
Now with the penis facing back towards you and the dog reasonably calm you can taste it. Take the tip in your mouth and use your tongue to stimulate it.
NEVER touch the penis with your teeth (or any other sharp object) and keep your lips wet.
NEVER suck a dog penis with the up/down motion like a human penis for the same reason as above. This is a dog, they work differently. You may have seen people do it wrong in (commercial) porn, but that was indeed wrong.

Always pay attention to the dog. Dog penis is delicate and can be easily damaged by rough handling.
The dog may want to turn around and lick his own penis a couple of times. Let him do it, you can keep the tip in your mouth while he licks his knot. He is most likely just moistening it up. I have noticed that my dog ejaculates more liquid when he licks himself.
If it happens that you scratch the penis accidentally and there are a few drops of blood, stop what you are doing and give the dog at least a day or two to heal.

If you are doing it right you may notice intense pulsing in the penis, which stops when you stop stimulating the penis or when you do something wrong. Closed or half closed eyes are also generally considered a sign of pleasure along with relaxed facial expression and droopy lips.

The end:
How long a dog will want to have sex depends on how horny he is. At some point the penis will begin to feel colder or begins to deflate. This is a sign for you that the dog will want to stop soon. The dog will become restless and attempt to move away. You must let go of the penis.
My dog has a special body language sign he uses to tell me to stop. Look out for such signals and respect them. It will build trust and clear communication between you two.

Let the dog take care of his penis himself. In most cases the penis deflates completely and goes back into the sheath. If your dog has long hair, you may want to check after a while and remove any hair that might have been pulled into the sheath with the penis.

Some tips for improved experience:
Smell the knot. It has a pleasant smell.
Do some semen collection in a cup, you can enjoy all the taste at once.
Learn headhumping. This means letting your dog mount your head and hump your mouth directly. You will get all the cum, not a single drop is wasted and it is much more fun. But it has to be done carefully and you have to know your dog well so nobody gets hurt.

Have a nice day.
This is so informative and really helpful. Thank you so much for posting.
 
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