I think my mum must have known I was a sissy, for one thing I was borrowing her underwear and I doubt I returned it perfectly. Also, I feel like a mother knows these things. She must have been aware of my small penis, and definitely she could see my little boobs too. She also would have known that I didn't have a girlfriend.
It would definitely have felt very good if she decided to dress me up herself and I'm sure it would have been a lot of fun for both of us. I never had a sister so I could have been her little girl. I also might have liked a gentle bit of teasing about my "shortcomings" and being a sissy, and I'm sure that would have been very funny for her, and very nice for me. All women love to tease boys like that.
I wouldn't have wanted any sexual contact or anything, but just to be her little sissy. I think it would have been a lovely thing to do, strengthening a bond between us and giving me what we both knew I needed. I think if a mummy knows she has a little sissy on her hands, she should definitely share that with him.
I've seen lots of people speak about this and lots of stories on various websites, and I'm very curious if anyone here experienced anything similar! Of course I'd love to hear all about it in as much detail as you can, because I just can't think of a more delicious experience.
I'd also love to hear if anyone has any similar fantasies.