Do you have a specific account in MS Outlook and you need a way to automatically request a "Read Receipt" for these people (but not everyone you email)?
In that case, you can set up a specialized "After Sending" Mail Rule:
1. Click Tools | Rules and Alerts, and select New Rule; this will start the Open Rules Wizard.
2. Select the option to 'Start from a Blank Rule' (near the top of the Window); also choose the 'check messages after sending' option. Click next.
3. In the Conditions window Step #1, checkmark "Through the specified account". In Step #2, click the link to "specified account" and choose your "account". When complete, click Next.
4. In the Actions Window, checkmark "Notify me when it's read". Click next.
5. Save the rule.
6. Keep Clicking OK until the Rules Wizard closes.