To suggest unlocking a TureCrypt volume the system needs first to know that the device contains a TrueCrypt volume. But the TrueCrypt header is encrypted, so nothing gives any hint about the content of this device. Consider:
bor@quokka:~$ sudo cryptsetup tcryptDump /dev/sdb
Enter passphrase for /dev/sdb:
TCRYPT header information for /dev/sdb
Version: 5
Driver req.: 7.0
Flags: 0x0
Sector size: 512 [bytes]
MK offset: 131072 [bytes]
Volume size: 104595456 [bytes]
PBKDF2 hash: ripemd160
Cipher chain: aes
Cipher mode: xts-plain64
MK bits: 512
bor@quokka:~$
The /dev/sdb was formatted as TrueCrypt volume and after having entered the password cryptsetup also understands and recognizes it. But nothing on this device identifies it as a TrueCrypt container:
bor@quokka:~$ sudo blkid -p /dev/sdb
bor@quokka:~$ lsblk -f /dev/sdb
NAME FSTYPE FSVER LABEL UUID FSAVAIL FSUSE% MOUNTPOINTS
sdb
bor@quokka:~$ udisksctl info --block-device /dev/sdb
/org/freedesktop/UDisks2/block_devices/sdb:
org.freedesktop.UDisks2.Block:
Configuration: []
CryptoBackingDevice: '/'
Device: /dev/sdb
DeviceNumber: 2064
Drive: '/org/freedesktop/UDisks2/drives/QEMU_QEMU_HARDDISK_1_0000_3a00_3a1d_2e7_2'
HintAuto: true
HintIconName:
HintIgnore: false
HintName:
HintPartitionable: true
HintSymbolicIconName:
HintSystem: false
Id:
IdLabel:
IdType:
IdUUID:
IdUsage:
IdVersion:
MDRaid: '/'
MDRaidMember: '/'
PreferredDevice: /dev/sdb
ReadOnly: false
Size: 104857600
Symlinks: /dev/disk/by-diskseq/56
/dev/disk/by-id/usb-QEMU_QEMU_HARDDISK_1-0000:00:1d.7-2-0:0
/dev/disk/by-path/pci-0000:00:1d.7-usb-0:2:1.0-scsi-0:0:0:0
/dev/disk/by-path/pci-0000:00:1d.7-usbv2-0:2:1.0-scsi-0:0:0:0
UserspaceMountOptions:
bor@quokka:~$
If you look at the content of the /dev/sdb with a hex editor, you will see what appears a garbage or random content.
You can unlock it manually though if you know the correct device:
bor@quokka:~$ sudo cryptsetup tcryptOpen /dev/sdb tcrypt
Enter passphrase for /dev/sdb:
bor@quokka:~$ lsblk -if /dev/sdb
NAME FSTYPE FSVER LABEL UUID FSAVAIL FSUSE% MOUNTPOINTS
sdb
`-tcrypt ext4 1.0 5ae80e09-d375-494b-86a3-49f00f9e7802
bor@quokka:~$
I do not think it is possible to do what you want using TrueCrypt.
For the sake of completeness - it is possible to run a command when USB drive is inserted. This command could be a script that first unlocks the volume and then starts Nautilus on the result. There are several alternative methods to do it in the answers to this question. Of course, the challenge is to unambiguously identify the device.