0001193125-15-314010 Sample Contracts

MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY Springfield, MA 01111-0001
Annuity Contract • September 8th, 2015 • Massachusetts Mutual Variable Annuity Separate Account 4

This Contract was approved under the authority of the Interstate Insurance Product Regulation Commission, hereafter referred to as “Commission” and issued under the Commission’s standards. Any Contract provision that on the provision’s effective date is in conflict with the applicable Commission standards for this product type in effect as of the provision’s effective date of Commission contract approval is hereby amended to conform to the Commission standards in effect as of the provision’s effective date of Commission contract approval.

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FUND PARTICIPATION AGREEMENT
Fund Participation Agreement • September 8th, 2015 • Massachusetts Mutual Variable Annuity Separate Account 4 • New York

THIS AGREEMENT is executed as of July 13, 2015 and effective as of July 13, 2015 (the “Effective Date”), by and among BLACKROCK VARIABLE SERIES FUNDS, INC. an open-end management investment company organized as a Maryland corporation (the “Fund”), BLACKROCK INVESTMENTS, LLC (“BRIL” or the “Underwriter”), a broker-dealer registered as such under the Securities Exchange Act of 1934, as amended (the “1934 Act”), and Massachusetts Mutual Life Insurance Company, a life insurance company organized under the laws of the Commonwealth of Massachusetts (the “Company”), on its own behalf and on behalf of each separate account of the Company set forth on Schedule A, as may be amended from time to time (each separate account hereinafter referred to individually as an Account” and collectively as the “Accounts”).

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