Orgasm in chastity

Port249 · Feb 10, 2023

MsPamela said: ↑

I would absolutely love that. But I don't know what to do, and am not sure it is even possible. Hubby, who isn't very talkative to start with, completely clams up about anything anal. I know he enjoys it, but I don't really know what he needs to get him over the edge. Faster? Slower? A longer dildo? Thicker? What position is best? Maybe I'm just giving up too soon and he needs longer to "warm up". If I understand correctly, his prostate is the key. But I don't know if I'm reaching it at all let alone providing the right kind of stimulation.

Would it be better to try giving him an anal orgasm manually (with toys) instead of pegging? It seems like it might be easier try lots of different motions, etc. On the other hand, he appears much more turned on while I'm pegging him than he is for any other kind of anal play.

I know there aren't going to be one-size-fits-all answers, but any guidance at all would be greatly appreciated.
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While getting pegged I've noticed it feels better when I relax my PC muscles on the stroke in and tighten them on the way out. Or vice versa. Sometimes it's the little tweaks that get the results.

fkfk · Feb 12, 2023

caged oragsm is much different from PIV orgasm, as you can't "shoot" it out the enjoyable way, but rather a drop by drop cum while in the cage

For my queen, her control over me while caged is not the masturbate without her knowing or supervision, she understand regular orgasm is needed for a healthy man, but she would not let me have the 100% pleasure if not served her right. Only serving her right get the reward, if not, minimal oragsm while caged

JaySaysYes · Feb 12, 2023

I have made myself cum in the cage using a vibrator a few times when we first started with chastity and I quickly realised I hated it. It was often painful.

I've also made myself ejaculate in the cage with just meditation and breathing/tensing, no toys. I didn't like that either.

nikkel · Feb 16, 2023

Gumballz said: ↑

Our golden rule is the one in the cage only is allowed to produce ejaculate if he becomes so sexually excited & spontaneously ejaculates in his cage or, if he is able to cum from nipple stimulation or, ejaculates while being pegged. Of course all the above will occur with no additional stimulation i.e. stroking of the penis which is mute as the penis will always be locked.
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That would be so erotic to have an orgasm while my dick is all shriveled up and straining to expand in my cage . I don't think I could achieve an orgasm. My jailbird's bars dig into my dick when it tries to expand .

nikkel · Feb 16, 2023

IB-Chaste said: ↑

I think the things to consider are:

Position
This is important. Doggy style is fun and seems to be the standard but the direction of entry actually drives the dildo away from the prostate. It’s more a gentle stroking.
When she’s behind I tend to arch my back more upwards so that the toy is pushing against my frontal walls.
Our favourite position is spooning. It’s just nice and loving. Also, I adopt the ‘recovery’ position. Like this with my under leg bent and the top one straight my penis is projected away from anything else, there’s nothing to interfere with it. As I’m laid down I’m also not tensing my torso and leg muscles, there’s less distraction.

Size of the toy
This is not the important factor. The knowledge that a 10inch dildo will probably far exceed the requirements of hitting the spot is. We’ve actually found that a shorter dildo with a more pronounced head does a better job, it rubs right where it needs to.
So maybe try some different toys. Think about the Ergonomics, what’s going to work well.
It’s not all about that though, there’s nothing sexier than seeing my wife with her 12inch monster dangling between her legs… being super aroused helps! She just doesn’t push it all the way these days. Not until the right moments and I’m begging for more (I mean, she can’t actually get all 12 in, but she definitely goes for it!)

Research.
He needs to know what’s he’s doing with regards to using his muscles to pull the toy into the right spot. He also needs to know not to force it, that’s it’s not about his penis. Once he understands this and just relaxes it will be very beneficial.
Something like the aneros is good. I didn’t get it at first, but after enough foreplay in that area I’ll tense my muscles and it will just poke the right spot and I’ll know. It’s like “yep, that will do it.” A few more contractions and I’m over the edge.

Duration/movements
I understand what you mean when you say pegging can be an endurance test. It’s hard at times to know when to stop if nothing further is going to happen.
Using manual toys could be an option, but he’s going to have to tell you it’s in the right spot and you’ll have to be careful not to deviate from there.
This spot is very much easier to find after a longer period of denial.
I would recommend a rotating massager. It’s a good start. It’s not necessarily a couples toy but you can still lay with him and touch him up a bit while it’s going on. Give him the assurance you want him to enjoy it etc. the benefits of it is it won’t get tired.
It’s actually now one of my least favourite ways to cum. It’s slow and methodical… which is great to overcome the endurance, but it also means you can’t ‘go harder’ when it’s required. Yes, I am a little ashamed to admit that I’m now very vocal when she’s pegging me.

My advice with regards to doing it as a couple and I suppose that’s more difficult with him being less open to the ideas…

You could possibly tie him down. Just massage him while he has something inserted in him. If you’ve also done the research you can tell him what he should be doing etc.

I would possibly try it uncaged. Only that way there is no concentration on the bars of the cage squeezing against the penis. There’s nothing else to think about. It won’t be long before that will matter.

It sounds like it’s going to be a whole lot of effort, and frankly the first one might not be that great but don’t worry, once it’s clicked for him they get better and easier to achieve. pegging will no longer be an endurance test. It can be over all too quickly. The feelings can be absolutely incredible. That I suppose gives you the upper hand, you can take him anyway you wish knowing that he won’t enjoy some ways as much as others.
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I just realized reading your post that the prostate is toward the cock, not to the rear .. How stupid of me !

Ackwon · Feb 16, 2023

nikkel said: ↑

That would be so erotic to have an orgasm while my dick is all shriveled up and straining to expand in my cage . I don't think I could achieve an orgasm. My jailbird's bars dig into my dick when it tries to expand .
Click to expand...

You will think again when you have a vibrator on the penis and a dildo in your anus Or even better, a vibrating butt plug. I can never survive a vibrating butt plug for more than a few minutes, no matter how restrained my penis is.

We had to get rid of all the vibrating tool when we restarted chastity training this year just so that I wouldn’t be able to cum easily

MichaelAlan · Mar 4, 2023

IB-Chaste said: ↑

I think the things to consider are:

Position
This is important. Doggy style is fun and seems to be the standard but the direction of entry actually drives the dildo away from the prostate. It’s more a gentle stroking.
When she’s behind I tend to arch my back more upwards so that the toy is pushing against my frontal walls.
Our favourite position is spooning. It’s just nice and loving. Also, I adopt the ‘recovery’ position. Like this with my under leg bent and the top one straight my penis is projected away from anything else, there’s nothing to interfere with it. As I’m laid down I’m also not tensing my torso and leg muscles, there’s less distraction.

Size of the toy
This is not the important factor. The knowledge that a 10inch dildo will probably far exceed the requirements of hitting the spot is. We’ve actually found that a shorter dildo with a more pronounced head does a better job, it rubs right where it needs to.
So maybe try some different toys. Think about the Ergonomics, what’s going to work well.
It’s not all about that though, there’s nothing sexier than seeing my wife with her 12inch monster dangling between her legs… being super aroused helps! She just doesn’t push it all the way these days. Not until the right moments and I’m begging for more (I mean, she can’t actually get all 12 in, but she definitely goes for it!)

Research.
He needs to know what’s he’s doing with regards to using his muscles to pull the toy into the right spot. He also needs to know not to force it, that’s it’s not about his penis. Once he understands this and just relaxes it will be very beneficial.
Something like the aneros is good. I didn’t get it at first, but after enough foreplay in that area I’ll tense my muscles and it will just poke the right spot and I’ll know. It’s like “yep, that will do it.” A few more contractions and I’m over the edge.

Duration/movements
I understand what you mean when you say pegging can be an endurance test. It’s hard at times to know when to stop if nothing further is going to happen.
Using manual toys could be an option, but he’s going to have to tell you it’s in the right spot and you’ll have to be careful not to deviate from there.
This spot is very much easier to find after a longer period of denial.
I would recommend a rotating massager. It’s a good start. It’s not necessarily a couples toy but you can still lay with him and touch him up a bit while it’s going on. Give him the assurance you want him to enjoy it etc. the benefits of it is it won’t get tired.
It’s actually now one of my least favourite ways to cum. It’s slow and methodical… which is great to overcome the endurance, but it also means you can’t ‘go harder’ when it’s required. Yes, I am a little ashamed to admit that I’m now very vocal when she’s pegging me.

My advice with regards to doing it as a couple and I suppose that’s more difficult with him being less open to the ideas…

You could possibly tie him down. Just massage him while he has something inserted in him. If you’ve also done the research you can tell him what he should be doing etc.

I would possibly try it uncaged. Only that way there is no concentration on the bars of the cage squeezing against the penis. There’s nothing else to think about. It won’t be long before that will matter.

It sounds like it’s going to be a whole lot of effort, and frankly the first one might not be that great but don’t worry, once it’s clicked for him they get better and easier to achieve. pegging will no longer be an endurance test. It can be over all too quickly. The feelings can be absolutely incredible. That I suppose gives you the upper hand, you can take him anyway you wish knowing that he won’t enjoy some ways as much as others.
Click to expand...

IB,

When being denied for an extended period trying to build upnto a prostate orgasm, will ruined orgasms set you back? I still feel very aroused after one but feel a degree of relief.
Thanks

IB-Chaste · Mar 4, 2023

MichaelAlan said: ↑

IB,

When being denied for an extended period trying to build upnto a prostate orgasm, will ruined orgasms set you back? I still feel very aroused after one but feel a degree of relief.
Thanks
Click to expand...

I want to say yes. Save it all up and it will make it easier. It would be a lie… but a nice little lie. Mentally, that’s when it happened for me. When there was no excuses in my own head about it.

I think what is actually really important is how aroused you are, a period of denial will aid with that and make it easier to achieve the first time around.

I think once it’s clicked and you ‘know’ how to let it happen it doesn’t matter so much. It could happen for me every time…

That said, I’ve been under lock and key for so long my wife only has to kiss me and look at me in a certain way and I can orgasm!

MichaelAlan · Mar 4, 2023

IB-Chaste said: ↑

I want to say yes. Save it all up and it will make it easier. It would be a lie… but a nice little lie. Mentally, that’s when it happened for me. When there was no excuses in my own head about it.

I think what is actually really important is how aroused you are, a period of denial will aid with that and make it easier to achieve the first time around.

I think once it’s clicked and you ‘know’ how to let it happen it doesn’t matter so much. It could happen for me every time…

That said, I’ve been under lock and key for so long my wife only has to kiss me and look at me in a certain way and I can orgasm!
Click to expand...

Thanks, Ill give
Your advice a try. Im even considering picking up that rotating vibrator. Itsnworth a try!

madams-sissysub · Mar 4, 2023

IB-Chaste said: ↑

So many questions…

No!!!
Sorry, that’s like a big no, all those exclamations… but that’s what it is. A big no! Any other stimulation will divert the attention away from the prostate pleasures and create more of a typical orgasm. You don’t want that. Achieving it from just anal adventure is so much better. It can be earthquakingly fantastic. The body shakes for minutes (that doesn’t sound a lot, but when you compare it to a typical orgasm it’s like an eternity!)
Persevere. It’s worth it.

So you know a ruined? It’s basically that. All the excitement of the orgasm approaching, but none of the pleasure of the release. The difference? If you enjoy it too much the attempted erection adds an element of pain. It’s can be a cruel way to orgasm.

Nah. Don’t panic on that, it’s like a ruin. Not so bad at all.

It could be. It could be incredibly frustrating, to tell him he’s going to have an orgasm and make him do it caged… I’m in favour of you doing that to him
I will say that like a ruin, you’ve got to limit them. Don’t give a caged orgasm and then a full orgasm over consecutive days. It relieves the frustration and therefore the enjoyment of the next.
The more you do in succession the more apparent the drop will become too.
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I totally agree!
Just focus on anal stimulation, for me the most intense is when Madam uses a dildo by hand as she can go faster and harder!

Newcomer · Mar 4, 2023

Chloé Rian said: ↑

I'll echo what Ms Angela & IB-Chaste have said, caged orgasms are "different." For me personally it's much closer to a ruin, maybe it takes a slight edge off but usually I'm still very worked up 5-10 min later.

The only time I experienced a "drop" was when a Magic Wand was used on the cage and wasn't pulled away when I started to cum. Even then, it usually just dribbles or pours out, there is no spurting. If the wand is taken away at the last second or if no additional stimulation other than anal is used, then it's basically a ruin.

Personally, I've started to like caged orgasms although I can't put my finger on why that is. It's not the real thing but it's still fun and incredibly frustrating and leaves you craving more!
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have you started to orgasm from prostate stimulation?

Newcomer · Mar 4, 2023

IB-Chaste said: ↑

My wife and I struggled with this for a long time. It was something we strived to achieve. We literally tried everything… even fisting. It was important to us and that heaped the pressure on. We were uneducated and as it turned out it was what I was doing that was holding us back.

You’re definitely reaching it. It’s roughly 3-4 inches inside.

https://www.lovehoney.co.uk/sex-toy...-rotating-prostate-massager/a42638g76716.html
This is the toy we used to make our discovery. It’s nothing special. It’s just a rotating dildo. Even the vibrations need to be switched off to make it work.

Chasity helped. That’s for sure. It got us to a stage where we knew that the prostate needed “milking”. It took away the excuses on that front.

This is the problem: You can’t teach him to have an anal orgasm. You can’t force it. It’s a counterintuitive experience that only he can master in his own mind (that’s my experience). You have to forget everything you knew about orgasms, completely forget how it usually occurs. Any strain, pressure, force to ejaculate from the penis and all is lost - I actually think of it like my wife’s orgasms. If she’s trying for it it won’t happen, she has to relax and allow it to progress on its own.
It’s an experience of intense relaxation that allows the stimulus on the prostate to take control.

The good news is, once he’s able to do it… pegging is incredible. It’s not only a submissive act of enjoyment. It reaches levels of intimacy (for the male) that you wouldn’t imagine. Laying down, completely immersed. Thinking of nothing but the soft touches of your partner on your skin whilst the slow methodical thrusting takes you close to heaven!
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Have you started to experience an orgasm from prostate stimulation? This is why I started wearing a chastity belt 2 days ago, I have a dildo that I use constantly and only once in 2-3 years of use I managed to achieve an anal orgasm, I tried with a vibrator, it feels like sperm just flows out without an erection and the same orgasm as from masturbation. Maybe that one time when I had an anal orgasm I was so excited that I just finished because my cock was hitting my stomach, but that one time I will remember for the rest of my life, it was incredible, how do you have anal orgasms now?

IB-Chaste · Mar 4, 2023

Newcomer said: ↑

how do you have anal orgasms now?
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The only way I can answer this: easily. Anytime anything is inside me. It’s a artform.

Newcomer · Mar 4, 2023

IB-Chaste said: ↑

The only way I can answer this: easily. Anytime anything is inside me. It’s a artform.
Click to expand...

that is, an anal orgasm can be even better than from ordinary masturbation?

IB-Chaste · Mar 4, 2023

Newcomer said: ↑

that is, an anal orgasm can be even better than from ordinary masturbation?
Click to expand...

I haven’t masturbate for nearly a year now. An anal orgasm can far exceed the feelings from a typical standard orgasm. It’s crazy!

Newcomer · Mar 4, 2023

IB-Chaste said: ↑

Я не мастурбую вже майже рік. Анальний оргазм може значно перевищувати відчуття від типового стандартного оргазму. Це божевілля!
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WOW, you are a master of chastity! I also have a goal to be locked before anal orgasm, but I don't know how? Tell me, please, how to understand that I got an anal orgasm?

MichaelAlan · Mar 6, 2023

IB-Chaste said: ↑

The only way I can answer this: easily. Anytime anything is inside me. It’s a artform.
Click to expand...

We tried an Njoy pure wand (caged ) and got to that feeling of needing to pee...I tried letting go, as you suggest, but while I was very very close I dont think I had one. However it was still pretty amazing. I leaked quite a bit snd even shot a couple times.

Nornally, I dont enjoy pegging without simultaneous penis stimulation and I have
Never leaked from just pegging.

So it would seem Im headed I'm the righ direction!

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Orgasm in chastity

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