Orient trailed at the break through Francois Zoko’s stoppage time strike, but they left it late to secure the point when the ball fell to Massey and he lashed the ball home for his sixth goal of the season.
The O’s made two changes to the side which lost 1-0 to Morecambe in midweek, with Liam Kelly making his first start since October, while Rowan Liburd was restored to the starting line-up.
It was a positive start for the visitors and Orient fashioned the first chance of the game when Michael Collins when he broke clear, before finding Nigel Atangana. He drifted in off the right and shot left-footed, but Artur Krysiak pushed the strike behind for a corner.
Up the other end Francois Zoko held off the challenge from the O’s defence and though he got a shot away, the effort was weak and Sargeant gathered in the Orient goal.
Skipper Kelly was then able to thread a ball through for striker Liburd, who took a couple of touches before dragging a shot well wide, while Yvan Erichot was forced to head the ball behind for a corner after a teasing delivery from Alex Lawless.
Matty Dolan unleashed a shot on 23 minutes and as the effort was blocked it presented the O’s with a breakaway through Sandro Semedo. The Portuguese youngster had Massey with him for support. The winger opted to go it alone though and he saw a shot blocked.
Liburd glances a header wide as the game passed the half hour mark, before the hosts had the best chance of the game. They worked the ball across midfield before playing in Shephard and unmarked, the defender flashed the effort into the side netting.
Orient continued to create opportunities and mostly through Massey. The winger picked up the ball in the middle of the park before playing in Judd down the right. He put the ball back into the box but it was diverted behind for a corner.
Kelly took it upon himself to have a shot from distance after 37 minutes and Krysiak produced an equally good save to deny the midfielder.
The deadlock was broken though in first half stoppage time and it went the way of the hosts. Tom Eaves’ effort from distance was deflected but keeper Sargeant did well to save, but Zoko was quickest to react and slotted the rebound home across goal.
Kennedy replaced Erichot at half time, with Hunt moving in to the centre of a back four before Paul McCallum was brought on for Liburd nine minutes into the second half.
Massey forced an early save from Krysiak, while Sargeant could only watch a Tom Eaves effort fall just wide of the post from 20 yards. The keeper then held Whitfield’s strike after Atangana gave away the ball inside the O’s box.
Josh Koroma replaced the Frenchman in the O’s final change as the O’s went to a 4-4-2 formation, before Kelly forced Krysiak into a solid save at his near post.
Koroma then had an opportunity of his own when played in by Massey, however, the winger flashed the effort over.
Just as the chances of a equaliser looked to have gone, up stepped that man Massey as he fired home from six yards after McCallum had headed down Koroma’s left wing cross.
Orient pounced on that and had chances late on to take all three points away from Huish Park as McCallum directed a header wide deep into stoppage time
YEOVIL TOWN: Krysiak, Shephard, Ward, Smith, Dickson (Mugabi 79), Whitfield, Lawless, Dolan, Zoko (Sowunmi 88), Akpa Akpro (Harrison 71), Eaves
SUBS: Maddison, Butcher, Goodship, James
GOALS: Zoko (45+1)
BOOKED: Lawless (55), Dolan (78)
ORIENT: Sargeant, Judd, Erichot (Kennedy HT), Parkes, Hunt, Massey, Atangana (Koroma 65), Collins, Kelly, Semedo, Liburd (McCallum 54)
SUBS: Grainger, Mezague, Moncur, Dalby
GOALS: Massey (88)
BOOKED: Semedo (71), Collins (73), Kelly (74), Massey (88)
REFEREE: Darren Deadman
ATTENDANCE: 3,120 (151 Orient fans)