Welcome to HCM.
Bp.140/100 It is called grade 1 hypertension
.If this is same 4 to 5 times within 10 days than you have to start Anti hypertensive medicine under guidence of cardiologist because you are already diabitic.Try to loos some weight because you are obese
.(your BMI is 32)
Improper method of measuring BP. may hurts you.
BP. should be measured after 10 minutes of rest.But my advice is don't measure BP. at home it may confuse you sometime better go to family physician