Can I take a tax deduction on my Health Insurance Premimums that come out of my paycheck?

Question

My employer sponsers this plan and the contributions i make are after tax dollars.

Answer 1

If they are after tax dollars then yes you can use them to compute Medical expenses for Itemized deductions on the Schedule A. Remember that all medical expenses must exceed 7.5% of your Adjusted Gross income, the first 7.5% gets subtracted from the actual expenses to get to the deductible amount.
If these were pre tax dollars they would not be deductible at all

If you are not itemizing your deductions, you can not deduct these expenses.

Publication 502
http://www.irs.gov/publications/p502/index.html

Answer 2

If you're paying in after-tax dollars, then yes, they can be taken as medical expenses if you itemize. But only the total medical expenses that exceed 7.5% of your income can be deducted, so while the technical answer is yes, the practical answer is probably no.