If you check Outlook Express Tools|Options|Receipts|Request a read receipt
for all sent messages, does that make any difference? If not, there's
probably no way you can do it from e-mail other than by using the "merge to
e-mail" approach described by Doug Robbnins at

http://word.mvps.org/FAQs/MailMerge/MergeWithAttachments.htm

and even that may not work with Outlook Express.

(FWIW it's not something I normally do, and I suspect I am not the only
person to dislike getting "read receipt" popup messages in my e-mail reader:
if I'm going to reply, I'd rather do it properly. If I'm not, I'd rather not
be pestered and tend to assume that responding to the receipt request is
going to result in some form of malware afflicting my system).

Peter Jamieson