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Can a Woman Tell?
I’m absolutely sure women can tell.

When I was a teenager I had a lot of girls who wanted to be just friends with me - they’d often say they felt ‘safe’ with me. Sometimes if I was around their house they’d get changed in front of me, stripping down to bra and knickers without a thought.

Even as I got older I’vd had girls asking me if they should worry about their boyfriends wanting to wear their knickers.
I sense most women or girls know when boys would be more accommodating to feminization . My mom raise 3 boys and 1 girl yet she only approached me to start wearing dresses. Yes I was introvert and shy, I liked poetry and shyed away from more boy activities (baseball, other sports, playing war games, etc, etc..). She also noticed I didn't mind to go clothes shopping with my sister or girl cousins for their dresses and such.
I liked wearing my dresses.
You are certainly in a lucky and enviable position. It would be interesting to see if your role evolves from a protector and facilitator to that of a role model and mentor.

Your post is a very inspirational one, I hope you can update as the summer unfolds.

Hopefully the boy gains confidence and grows his femininity as the summer progresses.

When I was in Sunday School (as we called it) over 40 years ago, one day a mom sent her son to class wearing his sister's blouse and crosstie with tights under his pants. The teachers all said he was "cute", and of course none of the boys dared make fun of him in a church.

(05-19-2018, 01:51 PM)dlittle6 Wrote: I had an incident recently following a vacation bible school meeting at church the other day.  A very attractive young mother whom I have seen around the church on Sundays actually cornered me off to the side.  Normally, Miss Brenda doesn't allow me to talk to other women without prior approval, but I was alone and really didn't have much choice.  I was in my male clothing with the requisite panty underneath.

Anyway, she started telling me that her son was going to be attending vacation bible school and would I be a "dear" and look out for him.  Naturally, I would, especially when requested by a member of  the superior sex.   She went on to mention that she was afraid of bullying, and that I would know what that was like.   Then she proceeded to tell me that this would be his first time out dressed as a girl!  Surprised and flabbergasted, I stammered a bit giving assurances.  She then asked if I knew what the weather would be in two weeks, and told me that he would be wearing a pretty flowered sun dress.  I was completely red and my face was burning as I thought about my own panties underneath.   Then she asked if I thought she should make him wear his training bra if it was too hot!!  I was speechless at that point, but managed to say that he probably should anyway just to get used to it.   i can't remember what else was said, but as she walked away, she turned, smiled and said, "Thanks, I figured that it takes one to know one." 

She never came out and called me a sissy, but she sure talked all around it!  I asked Miss Brenda, but she said she had never talked to the woman, so she probably just sensed it.  The subject was closed at that point. 

Can a woman tell?
I also wonder about this. I do think some women can, and that there are different levels of awareness between women.

I was once introduced to a woman, she took my hand and kissed the top of my wrist. Like you sometimes see a man do to a woman.
I only saw her that one time so I don't know what she thought.
Welcome, Dena, I can't help but suggest She thought you were such a "sweetie" that She just had to kiss your hand.
Thanks Gina! I love it when women call me sweetie!
Mother have a keen sense of when a boy or her son is effeminate. My mom knew that I was more of a girl then a boy as did an aunt of mine. I got to spend a whole summer in dresses at her home and my girl cousins knew I was a boy. They even told me more boys should try wearing dresses.

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