"I got all this so you could start dressing as a girl whenever you are ready hon, do you want to try any of it on?"
"yeah I do, can you pick something that you think I'll look good in, first." Jon asked
"of course I'd love to," Linda (his Mom) said, "I really liked this skirt and this tank top" she said picking them out "oh and wear these under them," she said handing him a bra, and foam breast forms and panties. "these are shape wear, the bra has pads to give you some breasts, and the panties have a padded butt and firm front to hide any of you don't want to show.
"thanks I guess Mom." Jon said taking the clothes and underwear to his room.
Jon stripped naked, he had never worn girl's clothes before, this was just for fun. he slipped on the black panties, found the little fold of cloth and slipped his penis into it between his legs. Looking in the mirror, the panties did a good job of making him look like a girl between the legs.
he put the bra straps on his shoulders then tried to clasp the clip in the back, and even after several minutes of trying, was unable to get it. he decided to ask his Mom for help.
"Mom?" he called out
"Yes honey?"
"Can you help me with the bra?"
Linda came into the room
"the panty looks good, I'll show you how to shave your legs if you want too"
"sure"
"here when you put a bra on you should turn it around and clip it first then position it"
"ah that makes sense." Jon said getting his bra on and placing the foam pads in. he quickly finished getting dressed after that, wearing a skirt was a unique feeling, he decided to let his Mom shave his legs, then show him makeup, he was going to do this for a while, there were so many types of girl's clothes, maybe he was getting into this.