I kind of like that fantasy Davina. I can only say that back in those days, I had no idea what transgender was or that just dressing up was possible.
Bringing it back to chastity, it's not really something I fantasize about. There is one aspect that interests me. I see myself as a one woman girl. I'm not really ruled by what's in my panties, but if I met a woman and fell in love and she wanted to lock it up, I would do it for her. The most intimate gift I could give her is control of that. I mean, she locks me up and has the key and she lets me know it. If I use it, it will only be with her and with her permission. I only want that anyway, but this way, she dictates when and where.
My wife, if I had one who was comfortable with me being 24/7, would control that. She would also help pick out my wardrobe. If I wasn't asking for release, she would bring it up. She would tease me and then tell me no and make me beg for it. I can imagine those times we are being intimate and being attentive to her needs. She would punish me of I didn't last long enough. I may be locked up longer. I may be spanked, but I would do my best to not fail her.
My releases might come in other ways. She might make me masturbate in front of her or she may do it for me and tell me when I could cum. She might make me use a toy when I did it. She might leave me locked up and only using a toy or take me with a strap on. I would learn to focus on making her happy and meeting her needs. I would become an oral devotee to her, even when it was only she who would get release. If it made her happy, I would do it, but she was always letting me know she loved me.
But, chastity would be 24/7 for me at her discretion. When we go out, she would delight in reminding me and teasing me. She might tell a few of her friends that I was locked up. She might have me show it. It's not so much that I'm a sissy slave or maid, but if she asked me to get her friends drinks and do something, I would. I also envision getting to go on shopping trips with her and her friends or beauty appointments.
I know chastity goes hand in hand with cuckolding for some. This is not something that sounds appealing to me. I know I definitely wouldn't like it if I wasn't included. I see myself losing interest very quickly if she's doing it privately. It means she would rather be with somebody else. If I'm in the room participating, servicing her and the guy and being included. Maybe we both entertain guys. We are together and not shutting each other out. Maybe. I see this as a dangerous game though.
Anyway, if I had a chastity fantasy, it would be along those lines. Not sure how many can relate to that. Not enough humiliation for some, but that's not really my thing