Caught

This guy always writes the same Types of stories I guess this is his favorite jerk off fantasy...

Try having him sit while you make him up then have him get dressed in his own sexy panties, bra and lace nightie, see if he wants to try heels
He will love you forever

Don't be a bitch, support him/help him let him explore his sexuality at that age every guy tries female wear it's just the thing that happens, if you are not open and helpful you could well end up with a sissy or gay guy that detests you, don't punish him get some girl wear for him that he knows is his own and let him wear whatever he likes at home

He is just finding himself, be nice, let him and help him explore his feminine side, don't make such a big thing of it.

Please don't do that to him, he is 17 feeling feminine and sexy. You should let him find his own feelings even let him wear some of your underwear, make a fuss of him, be affectionate, talk to him gently. what made you take a photo of him dressed.

At 17, I felt feminine and loved dressing in my aunts clothes as not only did they feel sensual but they gave me a sort of comfort feeling as well. My decision was to become a gay transvestite. I confessed to my aunt, who had brought me up and she was very understanding and explained about being gay and having different feelings to other boys, she was so lovely and helpful.

In my case, my aunt helped me to become more and more feminine, my uncle just accepted it. I now have a feminine name, Jasmine, work in a hairdressers where they accept me completely and I am very happy and contented.

Encourage him to be feminine. Take him shopping. Buy him a dildo and panties.