The majority of massive stars are formed in multiple systems, and at some point during their life, they interact with their companions via mass transfer. This interaction typically leads to the primary shedding its outer envelope, resulting in the formation of a “stripped star”. Classically, stripped stars are expected to quickly contract to become hot and UV-bright helium stars. Surprisingly, recent optical spectroscopic surveys have unveiled many stripped stars that are much larger and cooler, appearing “puffed up” and overlapping with the Main Sequence (MS) in the Hertzsprung–Russell diagram. Here, we study the evolutionary nature of puffed-up stripped (PS) stars and the duration of this enigmatic phase using the stellar-evolution code MESA. We computed grids of binary models at four metallicities: Solar (Z⊙ = 0.017), Large Magellanic Cloud (LMC, Z = 0.0068), Small Magellanic Cloud (SMC, Z = 0.0034), and Z = 0.1 Z⊙. Contrary to previous assumptions, we find that stripped stars regain thermal equilibrium shortly after the end of mass transfer and maintain it during most of the PS phase. Their further contraction towards hot and compact He stars is determined by the rate at which the residual H-rich envelope is depleted, with the main agents being H-shell burning (dominant for M ≲ 50 M⊙) and mass-loss in winds. The duration of the PS star phase is approximately 10% of the core-He burning lifetime (1% total lifetime) and up to 100 times more than the thermal timescale. It decreases with increasing mass and luminosity and increases with metallicity. We explored several factors influencing PS star lifetimes: orbital period, mass ratio, winds, and semiconvection. We further carried out a simple binary population synthesis estimation, finding that ∼0.5–0.7% of all the stars with log (L/L⊙) > 3.7 may, in fact, be PS stars. Our results indicate that tens to hundreds of PS stars in post-interaction binaries may be hiding in the MS population, disguised as ‘normal’ stars: ∼100 (∼280) in the SMC (LMC) and ∼1500 in the Milky Way. Their true nature may be revealed by spectroscopically measured low surface gravities, high N enrichment, and likely slow rotation rates.