I own the O-ME53 Magnifying Eyecup and I wear glasses. The VF diopter adjustment is not sufficient for me to shoot without glasses with or without the Eyecup.
I shoot left with right eye closed. Seeing the entire VF including the LED's has been more challenging on the K10D than on my MESuper. On my KX and Spot F I use SMC +2 diopter correction lenses and shoot without glasses. Correction is as near to perfect as one could get - especially considering the older cameras have microprism screens. The MESuper horizontal split image VF is a breeze to focus.
I tried the O-ME53 Eyecup for general use. Wearing glasses it limits my FoV in the viewfinder too much to be useful for hand held photography. When using a tripod (thus able to move my eye around the viewfinder) the extra magnification helps with manual focus while wearing eyeglasses.
I recently found a Nikon +2 diopter attachment that fits the M-series viewfinder frames. It slides down over the K10D frame and fits snugly enough that it will not come loose. Even with little peripheral vision (I have glaucoma and have lost considerable peripheral visual acuity) I can see the entire viewfinder, including the margins, without my eyeglasses. I adjusted the VF diopter so the LED's are as sharp as I can make them and I'm shocked at how much better the viewfinder image appears. The focusing screen seems to be clearer and the image is in sharp focus at the focus point; the image appears to jump into focus just as the focus confirmation hexagon appears.
The Nikon attachment does not accept the regular eyecup over its external frame, so there is not any cushion to protect my face from sharp edges. The diopter adjustment assembly that would normally be covered b the Pentax eyecup (either one) is exposed, which concerns me in case of damage to the assembly. An old Pentax rubber eyecup made to hold a custom correction diopter (ground by an optometrist), but without any glass installed, slides over the Nikon diopter frame and ameliorates this problem somewhat, and has the added benefit of blocking external light from the viewfinder while shooting..
I have tried looking "into" the VF and keeping both eyes open, rather than pressing my eye against the back of the camera. For just a few test shots this seems promising, but I'll have to see what I feel like after an extended outing. The hard frame edges aren't an issue with my film cameras, so I imagine I will simply need to adjust the way I hold the K10D up to my face. Holding the camera with my head turned to the left and my body facing about 30 degrees to the right of straight on to the shot, cradling the base of the camera in my left hand, is very comfortable. My nose does not contact the LCD screen so much this way. My pinky and ring fingers gently grip the bottom of my right hand. For manual focus lenses, my index and middle fingers and thumb adjust the focus ring. This grip is very stable. With time it will feel more natural.
Shooting without glasses seems like a reasonable strategy for times when I am going to take pictures without interruption. For those occasions when I will take one or two, then do something else, then take a few more, shooting without glasses might be more of a problem.
I will shoot without glasses for a time to evaluate whether removing and replacing them is an issue - I don't mind doing it, I just don't want to stretch or break the frames.
EDIT / ADDITIONAL: Shooting without glasses absolutely prevents chimping my shots. Since the object is to use this diopter when shooting MF, maybe I should just go to full manual, turn the LCD off and shoot like it is film!
Second observation: I need a cheap pair of "shooting glasses" that hang on a chain around my neck. Next time I go for an eye exam . . .