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So, I have always enjoyed anal play and prostate stimulation to try to help me cum more reliably since I started using injections. However, none of the prostate toys or plugs will stay inside during penetrative sex unless I clinch the whole time. That won’t encourage an orgasm for me.

We started experimenting a couple of months ago and now we kind of have a routine. After playing (Magic Wand), having both vaginal and anal sex and my wife having many orgasms (over 45 minutes to an hour and a half) we transition to the “make ME cum” mode. She will lay on her back, I’ll lube up her whole hand and sit back on it until her fist is all the way in. (Of course, preparation is key here for any butt play) When we do this, I am straddling her arm, so she can suck me while her fist does its magic.

She will slowly rotate her hand back and forth as I go up and down. Within 2 or 3 minutes, I will start to cum uncontrollably. Since she cannot stand the texture of cum in her mouth, I will cum on her chest. The first time we did this, I had two big squirts and she said “you’re cumming!” And I said “not yet”. Then I actually orgasmed and shot 6 more squirts, all larger than the first two. Amaaaaaaazing.

We have done some version of this 4 more times with success every time.

I know this won’t be a solution for many that don’t want ANYTHING near their butt and it may not work if you’ve had prostate surgery, etc. I get that. All I can say is that if you can and you’re open minded enough, some type of prostate play may be what you need to get over that hill. I’m still looking for a solution that will do the same thing while fucking. If only her arm was long enough to do this while we’re having vaginal or anal sex… OMG

You're correct, that's not for everybody, myself included, and I'm not against a little butt play. But(t) that's way over the top (bottom?) for me. Here's the answer for your original stated predicament: Male Pouchless Briefs. It'll let your dick out to play and hold the toy of your choice in place. Well probably not a toy of your choice if you're already into what sounds like fisting. But anyhow: https://www.adameve.com/lingerie/mens-wear/sp-the-pouchless-brief-11292.aspx?st=male+power+pouchless+brief. Probably found cheaper on Amazon.

bldoink wrote:You're correct, that's not for everybody, myself included, and I'm not against a little butt play. But(t) that's way over the top (bottom?) for me. Here's the answer for your original stated predicament: Male Pouchless Briefs. It'll let your dick out to play and hold the toy of your choice in place. Well probably not a toy of your choice if you're already into what sounds like fisting. But anyhow: https://www.adameve.com/lingerie/mens-wear/sp-the-pouchless-brief-11292.aspx?st=male+power+pouchless+brief. Probably found cheaper on Amazon.

Thanks, that just might work…

While my wife probably do that and I'm not loose enough,
Good for you. I enjoy prostate massage or even outside
stimulation which gets me off. My difficulty has been loss
of penile sensitivity. But, as posted above, a cut in Trimix
seems to be bringing it back. But anal stimulation is Great.
I sometimes enjoy an an vibratory but if Trimix is too high no go.