My suggestion is to run
openssl enc -aes-256-cbc -in plain.txt -out encrypted.bin
under debugger and see what exactly what it is doing. openssl.c is the only real tutorial/getting started/reference guide OpenSSL has. All other documentation is just an API reference.
U1: My guess is that you are not setting some other required options, like mode of operation (padding).
U2: this is probably a duplicate of this question: AES CTR 256 Encryption Mode of operation on OpenSSL and answers there will likely help.