You most likely suffer from dry skin in the anus region or generally dry skin condition. However it's not the end of the world and there are very simple things that can help you.
1. The first thing is to actually get the stool softer, that can be achieved by mid laxatives, however this is only a temporary solution. I'm not familiar with your diet and general digestive conditions but I would say the proper thing would be to drink enough water and fruit juices. No sodas, no soft drink, nothing with sugar and nothing dehydrating. I'd recommend to replace coffee with black or green tea (green is even better for general health and detox)!
2. When you have stool you should lube it up a little bit - just take any water based lube and it should be enough. This will make easier and reduce the tear.
3. I don't know what is available locally in Alabama, however I'm sure you can buy something similar like
Bepanthen and apply it after you have stool. Due to it's fatty structure it will preserve the moisture and the active ingredient (
Product Info) will repair the damaged skin.
4. Check with your doctor if the problem persist or during the next check up have let him have a look at this. Can be a
Hemorrhoid condition that needs to be treated.
When you finally overcome this issue and it should take a few weeks, you can start with really beginners toys. (Below is the repost of my usual beginners advice)
If you want to get into the anal play area with comfort and ease I guess the best thing is to start with smaller dildo like the:
Blush UR3 Anal Starter
or a silicone alternative:
Sedeux Please
To grow up I'd suggest:
Pure Skin Player jr
The silicone alternative is:
VIP Super Soft
For Butt Plugs:
The best training of all times (after you grow out of the beginners toys):
Triple Ripple
Best Butt Plug (I guess many will agree):
Ryder
And finally my personal favorite among plugs:
Gapers Organic
Generally speaking that's my product advice. For lubes you have to look for yourself what suits you more. Just don't use silicone lube on silicone toys, it really kills them. The rest as usual, hygiene, foreplay, foreplay, lube -> and plenty of fun