En español hay un curso en video del 2014 por Adastra de The hackerWay, también tiene libros en español

Videos originales en 720p (también están en YouTube pero con mucha menor calidad)

https://thehackerway.com/2014/02/04/hacking-con-python-parte-1-banner-grabbing/
https://thehackerway.com/2014/02/11/hacking-con-python-parte-2-reconocimiento-de-maquinas-en-el-entorno-de-red/
https://thehackerway.com/2014/02/18/hacking-con-python-parte-3-dnspython-para-consultar-servidores-dns/
https://thehackerway.com/2014/02/25/hacking-con-python-parte-4-enumeracion-de-usuarios-smtp/
https://thehackerway.com/2014/03/04/hacking-con-python-parte-5-conceptos-basicos-sobre-scapy/
https://thehackerway.com/2014/03/11/hacking-con-python-parte-6-arp-poisoning-mitm-y-dnsspoofing-con-scapy/
https://thehackerway.com/2014/03/18/hacking-con-python-parte-7-manipulacion-de-peticiones-http/
https://thehackerway.com/2014/03/25/hacking-con-python-parte-8-web-scraping-con-beautifulsoup/
https://thehackerway.com/2014/04/01/hacking-con-python-parte-9-web-crawling-con-scrapy/
https://thehackerway.com/2014/04/08/hacking-con-python-parte-10-mechanize-para-interactuar-con-aplicaciones-web/
https://thehackerway.com/2014/04/15/hacking-con-python-parte-11-desarrollo-de-un-crawler/
https://thehackerway.com/2014/04/22/hacking-con-python-parte-12-usando-urllib3-y-requests/
https://thehackerway.com/2014/04/29/hacking-con-python-parte-13-mecanismos-de-autenticacion-en-protocolo-http/
https://thehackerway.com/2014/05/06/hacking-con-python-parte-14-utilizando-nmap-desde-python/
https://thehackerway.com/2014/05/06/hacking-con-python-parte-14-utilizando-nmap-desde-python/
https://thehackerway.com/2014/05/20/hacking-con-python-parte-16-twitter-desde-python-utilizando-el-protocolo-oauth/
https://thehackerway.com/2014/05/27/hacking-con-python-parte-17-fuzzdb-y-pywebfuzz/
https://thehackerway.com/2014/06/03/hacking-con-python-parte-18-modulo-ftplib-para-acceder-a-servidores-ftp/
https://thehackerway.com/2014/06/10/hacking-con-python-parte-19-automatizacion-con-pexpect/
https://thehackerway.com/2014/06/17/hacking-con-python-parte-20-controlando-servidores-ssh-con-paramiko/
https://thehackerway.com/2014/06/24/hacking-con-python-parte-21-automatizacion-con-plumbum/
https://thehackerway.com/2014/07/01/hacking-con-python-parte-22-caracteristicas-avanzadas-de-plumbum/
https://thehackerway.com/2014/07/08/hacking-con-python-parte-23-controlando-instancias-de-tor-con-stem/
https://thehackerway.com/2014/07/15/hacking-con-python-parte-24-consulta-de-descriptores-de-tor-con-stem/
https://thehackerway.com/2014/07/22/hacking-con-python-parte-25-atacando-repetidores-de-salida-de-tor/
https://thehackerway.com/2014/07/29/hacking-con-python-parte-26-introduccion-a-twisted/
https://thehackerway.com/2014/08/05/hacking-con-python-parte-27-construyendo-clientes-y-servidores-con-twisted/
https://thehackerway.com/2014/08/12/hacking-con-python-parte-28-introduccion-a-pydbg/
https://thehackerway.com/2014/08/19/hacking-con-python-parte-29-scripting-en-inmmunity-debugger-pycommands/
https://thehackerway.com/2014/08/26/hacking-con-python-parte-30-scripting-en-inmmunity-debugger-pyhooks/
https://thehackerway.com/2014/09/02/hacking-con-python-parte-31-examinando-programas-y-librerias-con-pefile-y-pydasm-2/
https://thehackerway.com/2014/09/09/hacking-con-python-parte-32-uso-de-fabric-para-crear-botnets-sobre-servicios-ssh/
https://thehackerway.com/2014/09/16/hacking-con-python-parte-33-peticiones-http-contra-tor-utilizando-requests-y-requesocks/
https://thehackerway.com/2014/09/30/hacking-con-python-parte-34-examinando-servicios-snmp-con-pysnmp/

Libros:
https://thehackerway.com/libros/

Han de estar hechos con una versión vieja de Python pero igual te sirven como base, los puedes migrar a una versión más actual o a partir de acá seguir cursos o libros más actualizados con mucha más facilidad.