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No. 1681
>>1666
Alright, 1634 here again, let's see...
You didn't mention how much anal play you've done so far, so I'll start at the beginning. My first 'toy' was a CD-R spindle with a latex glove on it, pulled into a finger. (I've come a long way from that point! :P)
My next stop was a pestle (as in mortar & pestle) in a condom with the end tied shut. Its dimensions are about 1" wide by 6" long. Took it all the way in on my first try, and was officially hooked. :) Another good one for around that size is the handle of a screwdriver.
A good option for progressively working your way up is using Sharpie markers. You can start with just one, and then keep stuffing more and more markers into the middle of the bundle until you've reached your limit. Use the medium point ones with rounded barrel ends for easier stuffing. You could also try ballpoint pens if you want to take it slow. Might be cheaper, too, if you buy in bulk.
If you're heading to the produce aisle, yeah, I'd stick with the cucumbers. Bananas are too soft for anal stretching - unless you've already used something else to stretch you to that size, you're just gonna end up mashing it. Cucumbers also have the advantage of coming in a wide variety of sizes.
You could also try some bottles. You'll probably want to look for one with a gradually-tapered neck, no abrupt bulges. Though if you get experienced enough, some like taking the flat end first. Or just grab whatever looks fun, like a Pom pomegranate juice bottle.
Most of these options will work best when placed inside a condom, which will smooth out any rough bits and generally make things glide better.
Then there's the matter of lubes. Others have suggested conditioner or lotion. Those will do the trick if necessary, but I think there's a much better option: Crisco. Stays put, nice & thick, and nice & slick.
One last caveat: be careful with your purchases. A grocery store receipt lying around that reads "cucumbers, Crisco, and condoms" just might blow your cover. :D
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