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Anonymous File :-(, x)
Biggest thing I've taken up the arse is 2.5 inches, but I'm pretty sure my methods will scale up.
First, stop fucking around groceries and get some proper equipment. You should get a small dildo that goes up to about an inch in diameter to start, something that goes to 1.5 inches, something that goes to 2 inches, and so on until you can get a fist in. Textured surfaces, ridges, odd shapes like the picture or even animal shaped dildos all help to open you up quicker, experiment and find out what gets you loose.
You'll also need some good quality water based lube. ID Glide is great and I've heard good things about Astroglide. Note that these aren't intermediate stages that you drop and never use again. Each time you decide to go for the fist, you'll have to gently work the muscles, lube up and all that shit each time. Now you know why women are so focused on foreplay, you need to be in the mood and worked up to take anything beyond a finger.
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