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Ruined Orgasm with Chastity


Dubious

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Wasn't sure where to post this, so I figured here would be good

Not masturbated in at least a week and figured I should put on chastity before I got the urge, so been in chastity for 2 days now, and diapered of course.
Then today I looked at some pictures and read some stories, that lead to some anal play, still in chastity, with diaper on, I pulled the diaper to the side and pushed in the dildo, that I has on a rod so I can change position, from kneeling to standing and found a position to push hard on the prostate (Not using hands, other than to hold myself up)
When kneeling, I made it to precum, like I always do, but when I raised myself up and got pressure on prostate, It felt like I was cumming, but I didn't get an orgasm and since I'm wearing a diaper, I cant confirm that I actually did cum, but it felt like it, and it was "amazing" to have a ruined orgasm.

Looking forward to the next time, but not sure when that gonna be... just wish it was with another person.

Edit: Sat down after that session, then got up to walk and do some chores, then I bent down to pick something up and couldn't hold it, so I shit myself
Guess I was well lubricated as I cleaned out with little to no effort, almost like an enema..

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On 1/25/2020 at 9:03 AM, Dubious said:

Wasn't sure where to post this, so I figured here would be good

Not masturbated in at least a week and figured I should put on chastity before I got the urge, so been in chastity for 2 days now, and diapered of course.
Then today I looked at some pictures and read some stories, that lead to some anal play, still in chastity, with diaper on, I pulled the diaper to the side and pushed in the dildo, that I has on a rod so I can change position, from kneeling to standing and found a position to push hard on the prostate (Not using hands, other than to hold myself up)
When kneeling, I made it to precum, like I always do, but when I raised myself up and got pressure on prostate, It felt like I was cumming, but I didn't get an orgasm and since I'm wearing a diaper, I cant confirm that I actually did cum, but it felt like it, and it was "amazing" to have a ruined orgasm.

Looking forward to the next time, but not sure when that gonna be... just wish it was with another person.

Edit: Sat down after that session, then got up to walk and do some chores, then I bent down to pick something up and couldn't hold it, so I shit myself
Guess I was well lubricated as I cleaned out with little to no effort, almost like an enema..

Yes, lube and deep anal stimulation tends to give me a loose poop for a short time too.  I'm str8 but possibly bi-curious and do participate in self anal play to my wife's consternation and repulsion.  I have found not so much of the effect when using my LARGE stainless steel plug but when I use the silicone dildo (originally purchased by me for my wife's enjoyment), between deep stimulation and lube required to insert, it does tend to loosen up the bowels.

As to your "failed orgasm", I've done digital (finger) prostate stimulation before while masturbating and found that pressure at the right time on the prostate tends to stop the ejaculation portion of the orgasm but highly enhances the pleasurable contractions in the prostate related to orgasm.  When I used to do this, I might have a tiny amount of ejac, only flowing over the head and dribbling but very intense contractions deep within (prostate).  The feel as I recall my prostate orgasm from back then, was more of an intense single contraction that built up to about 2-3 times the strength of any one contraction of a regular orgasm, followed by several tiny contractions in rapid succession, almost like a whimper.

I wondered at the time if I might have retrograde ejac'd but I believe my pee was clear.  I'm not sure how long a retrograde ejac would be visible in urine though as I would imagine the semen would almost immediately start to break down in the very saline urine in the bladder.

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  • 3 months later...
On 1/25/2020 at 10:03 AM, Dubious said:

Wasn't sure where to post this, so I figured here would be good

Not masturbated in at least a week and figured I should put on chastity before I got the urge, so been in chastity for 2 days now, and diapered of course.

 

When I was in my teens, 20s and 30s I don't think I could ever go a week without ejaculating. I find male chastity devices interesting though. Do you use the cage style device? Ive seen them online and they fascinate me. If I used one when I was younger I might have had a relationship that lasted. I go both ways and had a few partners over the years who probably would have recommended a chastity device if they knew that was an option.

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Bought a cheap Holy Trainer v3 copy on Ebay, which is a plastic cage 

Don't really use it that much and it rarely stays on more than 2 days now (Weekends)
I get horny wearing it and can cum when caged, with magic wand 

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Chastity devices are fun, but they don't really work.  THey are usually pretty easy to get out of and with enough vibration you will orgasm.  An orgasm with one on can feel really intense and last a long time though or sometimes feel about like slightly wetting yourself.  

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The belt and PA piercing chastity works as they are impossible to get out of, without ruining either lock or penis
Without a magic wand or anal stimulation you wont orgasm 

Cages like holy trainer has more give and you can reach orgasm by just moving the cage, at least if you have a foreskin, from experience 

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  • 2 weeks later...
On 5/8/2020 at 11:43 AM, Sarah_Hillcrest said:

Chastity devices are fun, but they don't really work.  THey are usually pretty easy to get out of and with enough vibration you will orgasm.  An orgasm with one on can feel really intense and last a long time though or sometimes feel about like slightly wetting yourself.  

Orgasms in chastity are earth shattering ! I feel like I came gallons and yes sometimes i pee and cum together, my legs shake and my body gets tense.. Orgasms in chastity are the best.

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  • 2 months later...

I have found that achieving an orgasm while caged is a most intense experience, far far better than just normal masturbation. It is even all the more pleasurable and is more intensified while wearing a soaking wet diaper. Naturally of course, vibrating toys are most certainly in order. But what I have been discovering more and more is that while that "shivering/shaking" moment overtakes me, the actual feeling of orgasm is much more on the lines of deep wonderful sensations but with only copious amounts of precum that had leaked out during diaper/caged masturbation. Now maybe that does not really fit into the actual meaning of "failed orgasm", but when compared to an actual intense moment of plentiful penis milk spurting I have now found that I rather have one of those intense but failed moments with lots of precum leaking out in my pee soaked diaper. ?

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On 5/18/2020 at 8:05 PM, Transfusionelle said:

Orgasms in chastity are earth shattering ! I feel like I came gallons and yes sometimes i pee and cum together, my legs shake and my body gets tense.. Orgasms in chastity are the best.

I agree completely, my boyfriend rarely lets me out of chastity now. I needed to be talked into trying the cage initially but its mazing how good the orgasms feel wearing the cage. My cum and pee both come together and as I'm IC both just ooze out, but the high is icerdible

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  • 2 months later...
On 5/5/2020 at 1:56 PM, rubbersheetmike said:

When I was in my teens, 20s and 30s I don't think I could ever go a week without ejaculating. I find male chastity devices interesting though. Do you use the cage style device? Ive seen them online and they fascinate me. If I used one when I was younger I might have had a relationship that lasted. I go both ways and had a few partners over the years who probably would have recommended a chastity device if they knew that was an option.

Dude, if you're at all intrigued.  Get one.  You can try the best, holy trainer, for around $20. 

I generally put it away myself, and tell Momber that it's there when she wants it.  Sometimes 3 weeks go by, hmm maybe it just feels that way, I'll have to get out for a day or two.  I alays keep a key for cleaning, but I'm a good boy and put mommy's toy away immediately. Immediately after a thorough and vigorous wash.  

I didn't say nothin, so dont be tellin nothin.

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On 10/14/2020 at 3:03 PM, Amber's Boy said:

Dude, if you're at all intrigued.  Get one.  You can try the best, holy trainer, for around $20. 

I generally put it away myself, and tell Momber that it's there when she wants it.  Sometimes 3 weeks go by, hmm maybe it just feels that way, I'll have to get out for a day or two.  I alays keep a key for cleaning, but I'm a good boy and put mommy's toy away immediately. Immediately after a thorough and vigorous wash.  

 

I'm post-sexual nowdays so it wouldn't do me much good. But I find the idea interesting.

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I am on day 69 of a 90 day chastity lock up in a steel belt, and my hubby and I have just recently got in to diapers, my hubby loves this new level of control.

Due currently release from chastity 12th November.....yay

But then 2nd December I start a one year lock up..... hubby cannot wait, and now diapers are in play, an interesting year ahead for both of us

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  • 2 months later...
On 8/5/2020 at 3:48 PM, SrDiapCaged said:

I have found that achieving an orgasm while caged is a most intense experience, far far better than just normal masturbation. It is even all the more pleasurable and is more intensified while wearing a soaking wet diaper. Naturally of course, vibrating toys are most certainly in order. But what I have been discovering more and more is that while that "shivering/shaking" moment overtakes me, the actual feeling of orgasm is much more on the lines of deep wonderful sensations but with only copious amounts of precum that had leaked out during diaper/caged masturbation. Now maybe that does not really fit into the actual meaning of "failed orgasm", but when compared to an actual intense moment of plentiful penis milk spurting I have now found that I rather have one of those intense but failed moments with lots of precum leaking out in my pee soaked diaper. ?

What you have to try is having a male friend massage your prostate with his penis, or have a female wear a strapon and go to town on that prostate. It will be earth shattering and the shivering and shaking feeling is doubled. Like I have said even with a steel cage I spurted all over my shin a few times and the feeling is intense.

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3 hours ago, Transfusionelle said:

What you have to try is having a male friend massage your prostate with his penis, or have a female wear a strapon and go to town on that prostate. It will be earth shattering and the shivering and shaking feeling is doubled. Like I have said even with a steel cage I spurted all over my shin a few times and the feeling is intense.

Being your loving wife I have seen them shattering orgasms and have felt you shake and shiver love. I wish to keep pleasing you more and more each time. Men you can achieve some great orgasms if only you just open your hearts to your loved ones.

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@Evelyn Dellcerro

How TRUE it is:  and I remember the song "How True it is To Be Loved By You"  This applies SO Much, and I agree:  with the RIGHT touch, you could send someone into ORBIT, and MAN, does it feel GOOOOOD - Right Elle *grin* ;)

Brian

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On 8/10/2020 at 7:35 AM, DaveeBEd said:

I agree completely, my boyfriend rarely lets me out of chastity now. I needed to be talked into trying the cage initially but its mazing how good the orgasms feel wearing the cage. My cum and pee both come together and as I'm IC both just ooze out, but the high is icerdible

@DaveeBEdI tried a cage for the first time last night with someone I just had a first date with. He is 10 years older than I and I have to say it was something I never expected. I met the guy while out with family and friends and he is DL which really made me feel very safe and comfortable with him. The age difference did not even cross my mind. I never have been handled like I was last night and it brings new meaning to manhandled. This man handled me with such precision and care and made me ejaculate hands free 3 times in a row. I moaned and bit my pillow with such force I am sure the teeth marks are still there. I have to admit being young has its advantages and new encounters open me up to new feelings. Cage orgasms is something all men should try even if you are straight, you gotta try it.

On 1/25/2020 at 10:03 AM, Dubious said:

Wasn't sure where to post this, so I figured here would be good

Not masturbated in at least a week and figured I should put on chastity before I got the urge, so been in chastity for 2 days now, and diapered of course.
Then today I looked at some pictures and read some stories, that lead to some anal play, still in chastity, with diaper on, I pulled the diaper to the side and pushed in the dildo, that I has on a rod so I can change position, from kneeling to standing and found a position to push hard on the prostate (Not using hands, other than to hold myself up)
When kneeling, I made it to precum, like I always do, but when I raised myself up and got pressure on prostate, It felt like I was cumming, but I didn't get an orgasm and since I'm wearing a diaper, I cant confirm that I actually did cum, but it felt like it, and it was "amazing" to have a ruined orgasm.

Looking forward to the next time, but not sure when that gonna be... just wish it was with another person.

Edit: Sat down after that session, then got up to walk and do some chores, then I bent down to pick something up and couldn't hold it, so I shit myself
Guess I was well lubricated as I cleaned out with little to no effort, almost like an enema..

 

On 1/25/2020 at 10:03 AM, Dubious said:

Wasn't sure where to post this, so I figured here would be good

Not masturbated in at least a week and figured I should put on chastity before I got the urge, so been in chastity for 2 days now, and diapered of course.
Then today I looked at some pictures and read some stories, that lead to some anal play, still in chastity, with diaper on, I pulled the diaper to the side and pushed in the dildo, that I has on a rod so I can change position, from kneeling to standing and found a position to push hard on the prostate (Not using hands, other than to hold myself up)
When kneeling, I made it to precum, like I always do, but when I raised myself up and got pressure on prostate, It felt like I was cumming, but I didn't get an orgasm and since I'm wearing a diaper, I cant confirm that I actually did cum, but it felt like it, and it was "amazing" to have a ruined orgasm.

Looking forward to the next time, but not sure when that gonna be... just wish it was with another person.

Edit: Sat down after that session, then got up to walk and do some chores, then I bent down to pick something up and couldn't hold it, so I shit myself
Guess I was well lubricated as I cleaned out with little to no effort, almost like an enema..

@DubiousYou made me laugh so hard with your edit that I peed my diaper uncontrollably. That has happened so many times to me after sex. All lubed up and only place to go is my diaper. I was sweeping under the kitchen table one morning just after anal sex and bent down to pick up some chips with the dust pan and just let it all out in my diaper. What a great feeling though. Thanks for the shits and giggles.

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10 hours ago, tryingtocope said:

Um, cages scare me. I really don't like the idea of being denied and being told to be a "good girl". As if touching yourself makes you bad? No it doesn't.

Cages are fun and if done right give you great orgasms. I dont understand the part about being a good girl, but me and my diaper loving friend loved having on a cage and having a prostate orgasm. We love touching each other and nothing bad about that. Dont know where you getting the idea of being denied, but have a great day. Cages are fun..

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  • 1 month later...
On 1/25/2020 at 3:03 PM, Dubious said:

Wasn't sure where to post this, so I figured here would be good

Not masturbated in at least a week and figured I should put on chastity before I got the urge, so been in chastity for 2 days now, and diapered of course.
Then today I looked at some pictures and read some stories, that lead to some anal play, still in chastity, with diaper on, I pulled the diaper to the side and pushed in the dildo, that I has on a rod so I can change position, from kneeling to standing and found a position to push hard on the prostate (Not using hands, other than to hold myself up)
When kneeling, I made it to precum, like I always do, but when I raised myself up and got pressure on prostate, It felt like I was cumming, but I didn't get an orgasm and since I'm wearing a diaper, I cant confirm that I actually did cum, but it felt like it, and it was "amazing" to have a ruined orgasm.

Looking forward to the next time, but not sure when that gonna be... just wish it was with another person.

Edit: Sat down after that session, then got up to walk and do some chores, then I bent down to pick something up and couldn't hold it, so I shit myself
Guess I was well lubricated as I cleaned out with little to no effort, almost like an enema..

I think what you are describing is what I call an anal orgasm.

I used to indulge in a lot of anal sex. I tended to climax really early on while being penetrated by a guy, but if he went on long enough I would cum again but with an orgasm in my anus not my cock. They were some of the best orgasms I have ever had and left me exhausted, 

And yes, anal sex solo or getting ploughed does inevitably loosen you up. One of the reasons I got not diapers was that i would lose control temporarily after an heavy anal session. A friend, who is into fisting, had a stash of pads and diapers which intrigued me, so i tried it. One Saturday morning, after my bf at the time had given me a good pounding, I discreetly pulled on some pull-ups for our trip to the supermarket. As we walked around I shat myself. Just a little bt it was thrilling

 

 

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