Cumming in Chastity

You can try first to learn to use a vibrator on your penis (instead of jerking off) to make it cum soft trapped in a cage or very tight underwear. Once you start cumming this way you may get easier to do it just with your dildo.

I love using a vibrator on my little dick ..it makes me cum so hard not even touching with my hands and I just cum all over myself.

It feels wonderful.
 
You can try first to learn to use a vibrator on your penis (instead of jerking off) to make it cum soft trapped in a cage or very tight underwear. Once you start cumming this way you may get easier to do it just with your dildo.
My advice is just the opposite. Use the vibrator only when you don't cum with a dildo. Vibrators desensitize you to stimulation and makes it harder to cum. If you practice, use the dildo to learn to accept a cock and only use the vibrator if you really want to cum and the first two methods aren't working.
 
I occassionally us the thin 4" vibrator and use directly on my prostate, 95% of the time i'll leak all my semen, not ejaculate/ squirt it and also while totally flaccid.. I mean not even remotely hard, totally soft. I wouldn't say it pleasurable, but it still feels ok. I mainly do it to remove my ability to get erections for a few days, thus lessen my need to masturbate. My wife and I found, if we do it twice, say 15-20 minutes later, it leaves me impotent for 4-5 days, and no matter how much porn I look at, my brain and penis have a total disconnect for those 5'ish days.
 
Can't really see your problem. If you feel guilty around your girl after jerking you got some conversation to do... anyway the answer to your question:

Use a dildo thats not to big, but curved. Make sure you touch your g-spot. I'm sure you feel it when you hit it. Then place a vibrator on your cage. If tvat dont bring you to O, I dont know what..
 
Before 7". Now caged for over 6 weeks. No milking, no masturbation. Gym. Watching porn, no effects. Working out should increase my testosterone levels. But I don't know where my sperm goes. My dick shrank like 3" and yesterday changed to a smaller, really smaller cage like this.
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Only last night, I cum in my dreams. The stuff was full of small yellow crystal-like things - dried-up sperm? Anyways. Today I was a bit tired. Worked out and now I'm overactive again.
 
Unable to jerk off I have started sitting on a small dildo wile watching IR porn. I start squirting through my chastity now. I have never jerked off this way. It makes me feel so guilty and is confusing. Is this normal?
It is just nature setting things right again. Its the natural order of things. White men are half female. Just go with it. Because, u cant stop it.
 
Unable to jerk off I have started sitting on a small dildo wile watching IR porn. I start squirting through my chastity now. I have never jerked off this way. It makes me feel so guilty and is confusing. Is this normal?
It is wonderful! You are achieving a hands off sissygasm! A delight for cuckolds in chastity! And a step further on the cuckold path!
 
i tend to agree with dildo with no vibe, a cock shaped one or a moderately aggressive butt plug. a buzzing vibe on your prostate can get you to ejaculate without the orgasm more often, if ruined orgasm is your goal though - you got it. i can only speak of my experience, the stretching and full feeling of some plug or dildo slipping and popping in and out works for me. though i go soft when i have something in my ass, it still gets me to pleasant orgasms. conditioning and practice.
 
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