Rookie needs help: Two shell sessions in one

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Hi everyone, I am new here and I am very new to be
working with SSH

Problem:
I need to establish a session within a session.

The first connection goes to a remote box. The second
connection goes to that same box but within the
previously established shell and from there to another
machine in another location, I am tunneling SOCKS5
programs through the second session.


How I did it before:
Until now, I have used Putty twice (on windows XP) to
do that but since I switched over to Linux Ubuntu, I
am using the pure command line.


So far, I have been able to establish the first
session by doing:
ssh -D 1088 -p 443 username@remoteboxIP

Previously on XP, I would now open the second putty
session configured as follows:
Under Session:      IP_of_second_remote_box   |   
Port 443   |    SSH
Under: Connection--Proxy:  SOCKS 5 | Proxy Hostname:
127.0.0.1 | Port 8888

Can you point out what the equivalent command line
input would have to be ?

Thanks for the help :))

PS: sorry if this question is too trivial




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