This is my working hypothesis - the way I see it as of this moment!!
and that of Zane Perry.

  Phillip Perry, who bought 100 acres from Nicholas Aldred 10 Sept 1655 in Isle of Wight,  wrote his will 20 Nov 1667 in Isle of Wight Co, VA  and gives his age at 70 years or there about.  
On 9 Oct 1669, Ralph Channel, in right of Grace, his wife, relict of said Perry, requested probation of will. His surities were Richard Penny and James Bagnall.

  The eldest son, Phillip, disappears from the records and may have moved to Nansemond. 

  In 1673 John Perry, son of Phillip of "Whitemarsh" decd  sold the land he inherited from his father to Col. Joseph Bridges of "Whitemarsh" who had a large estate nearby. In 1693 John Perry, son of Phillip Perry, dec. conveyed a tract of land to Col. Joseph Bridgers lying in Whitemarsh.

  On 10 Aug 1674 John Perry requested administration on the estate of John Young who died intestate, he having married Elizabeth Young, daughter and heir of John Young. His surities were John Marshall and Francis Ayers.
   John Young was probably the son of Richard Young, who patented land in Isle of Wight in 1635. John Young was mentioned in the will of Edward Cherwine, 27 Sept 1649.

   John Perry and his wife Elizabeth of the Upper Parish of Nansemond on May 26 1675 sold to Nathaniel Bacon 70 acres in Lower Parish of Isle of Wight bought of John Young and Robert Butts. A John Perry held 870 acres in Nansemond in the Quit Rent of 1704. 

Children of Philip Perry and his wife Grace:
1. Philip Perry ca 1652 -
2. John Perry  (under age in 1667) ca 1653 -
      married by 1674 Elizabeth Young
            daughter of John Young ca 1615 - 1675

Isle of Wight Book A 
Thomas Hinson sold to William Brunt, a parcel of land upon southside of John Newton between 100 acres to James Watson and said Wm. Brunt is to have with as good assurances as John Seward hath given me. It said Wm. Brunt doth lose said land and Mr. Robert Pitt do require it, I do bind myself to pay 1000 weight in Tobacco and cask to Wm. Brunt. Dec 1643. 
Wm. Brunt assigns same to Thomas Kerrke 19 Oct 1644. 
Thomas Keerke assigns same to Nicholas Aldred 23 Nov 1645. 
Nicholas Aldred assigns same to Phillip Perry 10 Sept 1655. 
   - Boddie’s abstract

"John Young. Dying intestate, administration requested by John Perry, who married Elizabeth, ye daughter and heir of the decedent. August 10, 1674. Security: John Marshall, Francis Ayres." This would mean that in the same 1674/1675 timeframe there was a John Perry who was married to Elizabeth Young, but not particularly the same man (although could be) as the John Perry who one year later in 1675 provided Security for one Benedict Lewis.

Isle of Wight County, Virginia Administrations and Probates, Volume #1,  probate for one Benedict Lewis. It says "dying intestate, administration requested by his relict, Hannah. June 9, 1675. R: June 15, 1675.
 Security: Richard Silvester, John Perry Sr., page 36."

The realization is that it calls John Perry "Senior" in 1675. This means they were differentiating between at least two John Perrys that needed to be differentiated. If Phillip and John were both under age 16 in 1667 when Phillip Perry wrote his Will in Isle of Wight County, then they were born no sooner than 1651, and perhaps later.

Isle of Wight Will and Deed Book 1 - John Perry. U. P. of Nansemond for 5000 lbs tobacco sells to Nathaniel Bacon 70 acres in Lower Par of Isle of Wight bought of John Young and Robert Butts who bought the same of Anthony Jones long since deceased. Eliz. Perry relinquishes d ower. 26 May 1675. Wm Smyth, John (x) Ross. . Boddie’s abstract

This clearly indicates that  at the same time as the John Perry Sr. who provided a security for Benedict Lewis's Probate in Isle of Wight County in 1675 a John Perry (who lived in the Upper Parish of Nansemond County) had a wife named Elizabeth, and he sold land in Isle of Wight County in the lower parish. 
Phillip Perry resided in the Lower Parish on Brewers Creek.

Quit Rents of VA 1704   compiled by Smith
 Nansemond Co:      Perry, John . . . 870 a.,  
                                    Perry, Nicho. . . . . 200 a.
Prince George Co:  Perry, Grace. . . . 100 a.,  
                                    Perry, Joseph . . . 275 a., 
                                    Perry, Micajah . . . 600 a.
Princess Anne Co:  Perry, Joseph . . . 35 a., 
                                   Perry, Thomas . . . 650 a.
Accomack Co:         Perry, John . . . 217 a.,  
                                    Perry, Thomas . . . 232 a.
Essex Co:                  Perry, Samll . . . . 225 a. 

    John Perry was the son of Phillip Perry who died in Isle of Wight Co VA in 1667 at about the age of 70. He was underage at the time.
   John Perry had married by 1674 Elizabeth Young. 

Children of John Perry and Elizabeth Young: