We have the Share - but never use it. It turns out that when pegging it's pretty hard to make something this short functional. My wife would succeed with the initial penetration - but when she would try to thrust - it just kept popping out.

It wouldn't surprise me if they stopped making it - because it just doesn't really work.

As far as something he can handle - spend more time on preparation. We have some but plugs in the 1.25" to 1.5" range - as well as some tapered dildos. Neither of us accept anal penetration until using these toys to help relax the naturally tense sphincter muscles. With plenty of lube (reapplied many times) - it's easy to tell when enough relaxation has occurred. Admittedly over time - it takes less preparation because the body learns to adapt.

When you get into somewhat larger/longer toys - you may want to look into lube-shooters, they get the lube deeper so that it's more comfortable for thrusting.

Best of luck.