Do you mean the red boy or rude boy bcs I can't find any plugs called naughty boy.

If it pops out there is habitually nothing you can do to make it stay in unless you sit on it. It's not you but how the toy is constructed. It probably doesn't have a neck that is substantially thinner than the rest of the toy to allow it to *lock* into place. Hope this helps.

Looking around I found a prostate massager called the naughty boy, I think that's what TWG is talking about. Eden doesn't carry it.

I have a prostate massager of a similar style (Prock), and Naughty Student is right, these toys don't have quite enough of a bulge to catch, especially once you get excited. I usually use mine sitting down, with a chair pressing up against the base in order to keep it in (I do use a towel to keep things nice, before anyone starts making sounds of disgust). Other methods can be contrived, and hands can be used when necessary (but using them does change the experience. If you like to use it laying down, I'd recommend coming up with something that has a small chunk of something that will press against the perenium bit (wood would be an easy choice, you could press your foot or a handy wall against the other end).

Best of luck, and perhaps you could post with your solution.

Yeah Eden Doesn't carry it. How much of a diameter bigger does a toy have to be at the bulge spot than the neck for it to stay in place? I'm probably going to get a different toy but this one was expensive and kinda sucks that it doesn't work so well. I'll have to try using it on my chair. Right now I only tried using it in my bed, but I too put a towel down. Hehe

I know underwear helps me when I use toys, they tend to slip out but wearing panties as tight and as high on my hips as possible will keep the toy in. Would that work for men too???

It depends what you want to do - I have a Ryder, and it's great as a stay-put plug, but it's not as stimulating as some of the other plugs I have. The only time I had a problem with the base of the Ryder was when I tried to push it all the way in with my finger, so I guess the safety question depends on how violently you orgasm, but it would probably be OK. In general, you just want to make sure that there is some sort of a flare (usually 1/2" or more on a side) to keep it from going all the way inside.

Yes, by all means you can masturbate with a plug, and it feels great! For a plug to use while masturbating I like a slightly heavier base so that I can wiggle the plug around against my prostate from time to time. I have the Bronco, and like it a lot, but there are other plugs that would work well, just spend some time checking out the plugs section of your favorite toy store.

The difference between plugs and prostate massagers is somewhat flexible, given that almost any plug will also stimulate the prostate. Most of the time, plugs are bigger and more "filling", whereas prostate massagers are often smaller and generally have some way to move it against the prostate (vibrator, handle, or a specially designed shape that translates pelvic muscle movements into prostate stimulation). Since you already have a dedicated prostate massager, you might want to look at a plug to give you some variety, and then when your new vibrator comes you can try out both and see what you like.