I have quite a lot of experience with ruining orgasms and I have a very talkative submissive husband. I force him to tell me everything. Every sensation he experiences. Every pleasure and every pain. I have used this information to gradually improve my routine.
If you're really going to ruin his orgasms the first thing you need to do is to teach him to ALWAYS ask for your permission to cum. This is to ensure that he's not spoiling your plan. You also need to learn his bodylanguage when he himself or you are jerking him off. You should look for visual signs of orgasm such as twitching muscles near his balls, perineum and asshole. These signals are your STOP signals. You should NEVER let him jerk himself after he has asked for permission. It is vital for a successful ruining that his penis is nowhere near anything that could stimulate him.
My husband is almost always in chastity but once every two weeks I let him out for a proper shower & shave (under my supervision). I use this opportunity to either milk him by massaging his prostate and seminal vesicle combined with one-way milking of his cock or by emptying him by ruining his orgasm. I prefer the latter because this means less work by me and an even more satisfying result. By ruining his orgasms I take away and reduce his hornyness and sexdrive for a while and this is what I really want to achieve.
Here is how I usually do it. Like I said before it is of utmost importance that his penis is nowhere near anything that might come in contact with it. I usually tie his hands behind his back using my beloved thumbcuffs. They're so small and beautiful, yet so powerful. I have him standing with his legs wide apart and his upper body resting against the dinnertable. This is also the position I use when milking him. This way he'll never know which way it's gonna be. It is important that he's not able to touch the table with his penis. His member has to be in "free air".
I usually position myself behind him sitting on a small foot stool for comfort. After a week or two in his belt he's always extremely horny and it doesn't take long. I start wanking him. Making sure to look carefully for his "signs". When he asks for permission to cum I know he's close and I look for the twitching of the muscles underneath his balls, around his perineum and asshole. The twitching is the first visual sign of an orgasm. When this happens I know that my husband has passed the point of no return and I immediately let go of his dick. When my stimulation stops he always starts clenching his buttocks and thrusting his hips but his dick doesn't receive any more stimulation and his orgasm is ruined. His cum just drips out of him and when I know the danger of orgasm is over i milk the rest of the cum out of him by gripping his shaft by my thumb and forefinger right underneath his balls and milking his cock by sliding my thumb and forefinger along his shaft being careful to release the grip and taking a new one in such a manner that I "milk" his cock. I'm not wanking him.
By doing this whatever spem is left in him after his ruined orgasm drips out.
I have tried several methods for ruining orgasms including spermstopping, botching etc.
Some of these methods minimizes his orgasm but they doesn't ruin them. He's always having some degree of orgasm and receiving some form of pleasure from these methods and this is something I don't want.
I have been able to successfully both ruin his orgasm and stopping his sperm.
But I'm usually not interested in stopping his sperm.
Actually I want as much of it out of his body as possible.
Even though a ruined orgasm is more pleasurable for my husband than a milking (he finds my handjob up until the point where I let go to be very pleasurable). The end result is more satisfactory to me. A ruined orgasm lasts longer than a milking when it comes to reducing his sexdrive and hornyness.
When milking him I've found the new vibrating toy "RudeBoy" from Rocks Off to be the best ever for massaging his prostate.
When he's in position I lock his hands behind his back and carefully lube his anal opening. When the opening is lubed up I push a lot of lube into his ass and get to work. Lots of lube is important because you'll want to keep going 10-20 minutes to make sure he's empty. The base of the RudeBoy makes a great handle. I push it into him and start fucking him with it. When doing so the tip of the toy will massage the prostate and his seminal vesicle. After only 20-30 seconds the fluids starts dripping from his cock. At first it's only seminal fluids but when I start milking him with the thumb and forefinger of my left hand he starts dripping sperm as well. I can bring my husband to the brink of orgasm doing this but so far he hasn't been able to orgasm from this kind of massage. After 10-15 minutes of massage he's so frustrated he'd do anything for an orgasm. He actually humps my hand and my toy to get more of it into his ass and to get more massage. He continually clenches his buttocks and thrusts his pelvis into thin air.
If you have anything on your wishlist.....this is the moment to have him promise you stuff!!!
My husband usually produce 1-2 tablespoons of cum during a milking. If I'm feeling especially wicked I collect the result and have him consume it.
This came out a little longer than I first intended but I felt it necessary to let you know my experiences with ruined orgasms. In my opinion the only method for ruining orgasms that work is the one where you let go at the point of no return. He should never be allowed to wank himself if you plan to ruin his orgasm. His hands must be out of the way!