Photos/Videos: Meet Robert Sherry, the Man Who Likes to Dress Up as a Life-Size Doll

When 70-year-old Robert, pictured above, looks in the mirror, which he does often when dolled up, he sees a beautiful blond woman, voluptuous in her yellow halter dress and chunky heels. Her name is Sherry and she passes her time taking selfies in the courtyard of her Orange County mansion and floating topless in a macaroni-shaped pool.

But without costume, Robert (not his real name) is a property developer, recently divorced, and living
with his 19-year-old daughter.

Robert is a masker, leading two very different lives: one in the so-called vanilla world of his family and coworkers; another dolled up as a life-size figurine in the privacy of his own home, or, occasionally, out with other cross-dressers and fellow mask-wearers. He began dabbling in cross-dressing 15 years ago, not long after finding some discarded women’s clothes in a rental property.

But he hated the way he looked with a face full of makeup and had nearly given it up until he donned his first mask.

“I looked in the mirror and didn’t see myself, I saw a fairly attractive woman, and that changed everything for me,” Robert remembers.

Then, six years ago, he purchased a full suit called a FemSkin, a purchase he calls “a life-changing experience.” Rob slips into his FemSkin once a week or more for elaborately costumed photo shoots in his house, which he posts on Sherry’s Facebook page. See more pics below.