Practice going bigger over time. Start with the dildo you have now and when you get it in, hold it in there for a while. Work your way up to being able to leave it in for a half hour with no discomfort. Then get something larger and keep working up like this. I can now take two fists and anal sex is great. I also like to wrap a tennis ball in a condom and jam that up my ass as well It feels soooo good.
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