For stretching to be successful it needs to happen steadily over a reasonable period of time. I compiled a guide to stretching a couple of years back, you can find it here.
I have had several recent inquiries about ways to get started with vaginal stretching. Contrary to what a lot idiots might tell you just cramming the biggest things you can find is NOT the way to go. It can easily result in tearing which isn't fun at all. My key to starting out is using...
www.kinktalk.com
Cant stress how important docs advice is.
Anally is easy to tear soft tissue and cause major bleeding and injury when it is rushed. Short version anal advice on my end is: lots of lube, frequent lube application, start smaller than you think you need to, work up slowly in length of time filled, then gradually increase size while reducing the time filled again. trust your body if it hurts too bad, cramps, pains, burns. stop and assess the situation.
With the veggie suggestion for anal. Careful as carrots and cucumbers have no give like a penis or fingers. this can go too deep and cause issues at the second sphincter muscle. Some types of Cucumbers have sharp bumps on outside. Wash everything and possibly use condom. Dont go from anal to vaginal with the same item without cleaning it you can get a nasty infection.
If you use house hold objects be sure there are no pointed edges or sharp seams from like a molding process. A popular choice among household items is hairbrush or makeup brush handles, small plastic bottles or thin can like items such as body spray. Try it on you tongue if you feel sharpness it needs to be sanded first or just left out of the toy mix.
Last warning for both holes is dont use somthing small enough to lose up there. A friend of mine had to have one of those EVO lip balm balls removed from her vagina in the ER cuz after two days she couldnt get it unstuck.