ProductGPT
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I would suggest getting something like these http://www.amazon.com/gp/product/B0084FXAQE/ref=pd_lpo_sbs_dp_ss_2?pf_rd_p=1944687722&pf_rd_s=lpo-top-stripe-1&pf_rd_t=201&pf_rd_i=B0020MHKFO&pf_rd_m=ATVPDKIKX0DER&pf_rd_r=1P7JD1RFNP55VC68P5SB. That way you can work your way into it.
This is a set of three with sizes that you can ramp up to. There are quite a few similar sets like this too. http://www.amazon.com/gp/product/B0084FXAQE?colid=1VUSBTWPVFWZ4&coliid=I1XFVATNWQLJY9&psc=1&ref_=wl_it_dp_o_pd_nS_ttl
Also, invest in some good anal-specific lube. I really like Sliquid.
Small or larger, still comes out. Small ones go in like a glove but always end up falling out. Bigger ones will go in with a little help but still fall out. This. https://www.amazon.com/Trinity-Vibes-Fill-er-up-Piece-Purple/dp/B0084FXAQE
To plug the hole, obviously. I'm not sure if these are Glock certified, though... ( ͡° ͜ʖ ͡°)
Also any good beginner toys available on amazon.ca?
Was looking at these: http://www.amazon.ca/Trinity-Vibes-Fill-er-up-Piece-Purple/dp/B0084FXAQE/ref=sr_1_28?s=hpc&ie=UTF8&qid=1429594588&sr=1-28