Bruce Jenner reportedly wore woman's clothes as a teenager.
The former Olympic gold medallist, 65 - who is in the process of transitioning into a woman - allegedly raided his mother Esther's wardrobe as a youngster and tried on her lingerie and blouses.
A source told RadarOnline.com: "[Bruce] would play dress-up as a kid, just like anyone else. However, as a teenager, Bruce would take items from his mum, Esther's, closet. It would be a sweater or a loose blouse and was always done behind closed doors.
"His favorite items of clothing were silk and satin lingerie. He has always liked the way it feels on his skin.
"For years, Bruce had felt ashamed of it, and that is what drove his athletic success, thinking that would banish the behaviour. It just didn't, and Bruce has broken down in tears over the years, telling close friends and family about the shame he felt as a teenager.
"He now recognises that there was nothing wrong with wearing women's clothes. Wanting to help other people, and especially teenagers, struggling with gender identity will become a big platform for Bruce."
The 'Keeping Up With the Kardashians' star - who has daughters Kendall, 19, and Kylie, 17, with his ex-wife Kris Jenner - is reportedly keen to become a "sophisticated" woman and his hoping his stepdaughters Kim, Kourtney and Khloé will help him.
The source added: "Bruce is going to be a very sophisticated and classy woman, but will not be seen in flowing gowns.
"He is going to be more of a pantsuit kind of lady and his daughters are going to make sure of it."
Meanwhile, Bruce - who will share his journey into a woman in an interview set to air in May - was involved in a fatal car crash over the weekend after his motor smashed into another vehicle, killing a woman and injuring seven other people.