Tenga has a very simple value proposition. Quick, easy and discrete sex toy products for men. They are single use so you peel back the wrapper, pop the top and then go at it. When you're done just pop the top back on and toss it out.
Of the ones I've tried the Rolling Head Cup is my least favorite. Designed for dual action, massage at the top as you thrust at the bottom, The Rolling Head Cup is probably one of the looser fitting products in the line. Still sized modestly at 6 1/2 inches, this product isn't a great fit if you're very well endowed, but for the average guy it will fit fine. The inside sleeve however has a much less grip on your member in favor of the rolling and stretching ability.
The Rolling Head Cup is designed to simulate 'Woman on Top' sex, but I found it to simulate 'Woman whose had a few kids' sex. As with other Tenga products the inside had stimulating ridges, but I never really felt all that stimulated. This product took much to much work to get where I wanted to go with it and never really registered very high on the fun scale.
For some reason the Rolling Head Cup seemed to have a much higher level of lube in it and I found it's looser size and the large amount of lube to make it a lot less mess free than the other Tenga products.
In general I think the Tenga line is a great concept, I'd definitely pick these up and pack with me on my next business trip, but of the Tenga products The Rolling Head Cup would probably be the LAST one I'd choose.