There is more than one approach to solve for this. Only thinking out loud but, there is a Utility Filter that will generate a date and allow you to provide an offset, but your requirement implies that you have a variable number of dates to calculate.
You might consider a implementing some script (JSR-223 step, Scripted Assertion, etc.) within a loop that calculates the value of a date. For example:
<add imports>
// your date could be preset for the first time through using the date filter found in Utilities
// assume that the date filter creates a current date in proper format and stores this date
// in a property called 'prop_date'
String aDt = testExec.getStateValue( "prop_date" );
// set up a date format and
create a calendar using the date then add one day to the date
SimpleDateFormat sdf = new SimpleDateFormat("yyyy-MM-dd' 'HH:mm:ss.SSS");
Calendar cal = Calendar.getInstance();
cal.setTime( sfr.parse(aDt) );
cal.add( Calendar.DATE, 1 );
// ADD code here to do something with the date or allow another step
// in the process to do something with the date before generating the
// next date
aDt = sdf.format( cal.getTime() );
// do something
// :
// set the date value back so next loop increments 1 day from previous loops date value
testExec.setStateValue( "prop_date", sdf.format( cal.getTime() ));
// if JSR-Step return and print the date as the last response
return sdf.format( cal.getTime() );
// OR if Assertion, change the Assertion to error when response is FALSE
return true;