only thing about veggies-fruit like cucumber is getting a grip on them not so much getting it in your hole but the action after it's there, toy cock dildos have a suction find a smooth surface put it on lube it up and ride it or at least grab the fake balls spread your legs lift your legs and shove it in or better yet have someone close shove it in.
About 6 years ago I was still pretty new to acting on my bi curousities but I was slowing gaining confidence. So, I went to a mens bathhouse in Reno, NV and had met a handsome guy in the video room. We went up to my private room to party some more. He had a huge horse cock - at least 10 inches long and very thick. I could barely get my hands wrapped around it. I loved sucking on it, and could get a few inches past the head of his huge cock; however, he was really agressive and kept trying to force my head down further on his cock. Of course I would immediately begin chocking and would pull back. He repeated this agressive action 4 or 5 times and I got intiminated.
Because of his overly aggressive actions, I was afraid to try letting him fuck ass. I was certain he would not be patient and let my ass get used to his huge cock. So we ended our party. He left my room angry and I've never seen him since. However, that night after I left, I was determined to never let that happen again. The next day I went to the XXX bookstore and bought some dildos that I could work with to train my ass to take big cocks and I wouldn't be intiminated again.
So I started off with a 7 inch "Slim Jim", then worked up to a 9 incher that is about 1 1/2 inches in dia. I also have a "Pool Boy" that is 8 inches insertable and about 2 inches in dia. I regularly play with these last two dildos in the shower. I also have an 18 inch double headed dong that I've fully taken inside me. But it is so flimsy and slippery, that it is hard to handle in the shower. I want so badly to play with this dildo with someone so we can fuck each other at the same time.
I've had some live anal play times, but none were as large as that horse-cock.