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ORIGINAL: plaything

Thank you, both, for replying :)

MsSonnetMarwood: The Lady I mentioned was, infact, a babysitter when I was only 13 (now 35). She was 20 and I later found out had been a domme in training under her older sister at the time. I already had a natural admiration of women - in a platonic sense - and my submissiveness was showing in a hunger for the religion my parents were indoctrinating me with and in my becoming a 'social chameleon'. Lastly, the town I was raised in was rather rough and women were treated rather poorly. I was continually hearing about the lousy way my mother's friends were treated by their men.

The sitter first impressed me by being the first woman I can recall who didn't seem downtrodden by men, instead she put little stock in them, she seemed to see womanhood as all the things I considered good in a person and my faith, but ascribing it to womanhood challenged my understanding of the faith at that time. Although I was already starting down the path of learning how to be the masculine sort of male, my time around her stirred something in me that wanted to look to womankind for my role models. Another time I overheard her discussing with her sister what a shame it was that I was going to become a "typical male" when I had the potential to be such a nice boy, and one of them said "or even a nice girl, its not too late".

I got jealous as she started being closer to my younger sister, but being around me sometimes seemed to bother her - because I tended to draw a little more of her domme aspect out than she felt was suitable for a 13-14yr old but perhaps in part because I was struggling to write off my feelings as the devil trying to lead me astray, and I was actively trying to embrace the very "typical maleness". For instance, one night, my sister had a friend over while she was sitting and I was virtually hanging off the sitters every word feeling like a complete outsider, but also *trying* to make myself aware that I had the thing that slotted in her slot. This lead to her telling me that if I wanted to be included with the girls, she could take me upstairs and dress me apropriately - and I distinctly recall the look of hope in her face.

I already, at this point, sort of wanted her to make it a decision, not an offer, and with my 8yr old sister there too, I said "no" before I'd really thought about it and she looked thoroughly dissapointed. When I recovered I backtracked, and she considered for a moment before saying "You missed your chance now". I wasn't going to beg infront of my sister but after the sitter put her to bed, and I was still up for a couple of hours, and she looked quite melanchology, I volunteered myself to be her "girlfriend" which evoked another few moments of considering looks but only a simple "don't be silly, I'm not going to wake your sister up".

I didn't care for her dressing me in girls clothes, but the prospect of seeing her pleased by my letting go of some of the manhood she so disliked felt ... divine. That gave rise to thoughts that so affronted my christianity, assigning divinity to a "mere woman", that I threw myself into church and trying to bury the devilish whispers. Meaning that I missed the next opportunity when it finally came many months later, and then by repetition twice more (different circumstances). She once commented on a heated religious debate my dad was having in the next room which she finished with "if you want to pray to someone, you should pray to someone living, and preferably a woman", then fixed me with a look and said "you could pray to me, I might not answer but I'd be here to appreciate it". In the agonizing moment while I tried to abandon my religion and do it, which drew the happiest and most hopeful look I've ever seen, the debate ended and my dad walked into the room.

After a couple of days of "wickedly" praying silently to her to see that I was already too deep in to my "man training" to cross the gap without her intervention, horror kicked in at my blasphemy and I burried myself in trying to devote myself to new and "safer" depths of religious brainwashing. The occasional comment or overheard remark that resonated was perhaps just enough to keep me from drowning out what was left of that part of me.

I won't go into all the other little nuances - but to get back to your question: I don't have "man in womans body" feeling, if that's what you mean't by part of my makeup, a small part of its development was certainly the lingering hopes to maybe one day "break out" of my christian shell and please the sitter, certainly there is a part which is the desire to demonstrate outright rejection of the male-proscribed male I tried to obliterate the little seed of "girly" that the sitter wanted for me.

But it goes beyond that - beyond the basic fem/sissy/gender-play stuff - but to willingly offer my male "image of god" self at the feet of a Woman and allow and assist her to use it to shape an idol to Womanhood and specifically to her. Again - I'm not just talking about the fem stuff at this point - that's just the laying down the maleness at her feet. From there on its about what she wants of/for her girl. Heh, I even perhaps imagine her putting the last dirt over my male sides burial by specifically teaching her "girl" how to pass as a man in any situations she feels its still appropriate for me to do so.

I hope that wasn't too much detail :)

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ORIGINAL: LadyEllen

I dont see it as sad. I see in it a story which very likely could have happened, at a time in a boy's life when inklings begin to turn to mad frenzied compulsions that can take on strong associations. The 20 year lady babysitting may well have been supervising the younger sister rather than the boy in question too.

I also see in it something of a fetishistic link between this first woman of whom the boy became sexually aware, and all subsequent relationships with women. He needs a woman alike with her who first stirred him, and I'm not sure that the crossdressing is all that important in that fetishistic link. Whats important is that he casts off the negative male image to which he feels from his upbringing, he must live up, and surrender it and so himself to her.

OP - you are going to have a difficult time, finding a lady who enjoys crossdressing you - at least from the impression I get from previous similar threads on that subject. I would ask, given my interpretation, whether crossdressing (by whatever name) is important to you as such, and ask yourself whether some other way of achieving the same ends of surrender to please a lady, might be just as adequate, and prove more successful for you?

E

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ORIGINAL: AAkasha

I am curious to hear what the kinky women who are mothers think of this babysitter and how they would react if these activities were conducted with their sons.  Would that be acceptable behavior for a babysitter?

Akasha

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ORIGINAL: AAkasha
I am curious to hear what the kinky women who are mothers think of this babysitter and how they would react if these activities were conducted with their sons.  Would that be acceptable behavior for a babysitter?

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ORIGINAL: plaything
It was also suggested to me privately that I seek counselling. Infact, I did, 10 years ago, when the conflict between this mindset and my religious faith were truly troubling me. I came away with a clean bill of [mental] health, and have since shed the more onerous aspects of my religion and began coming to terms with my particular form of admiration of Women.

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ORIGINAL: Najakcharmer

But given that the parents were fundies and raising a kid inside an Old Testament horrorshow, that kind of psychological pressure makes for very fertile ground for fetishes and paraphilias.  If you attempt to completely suppress and demonify normal feelings and urges, you tend to create intense internal conflict.  Think of it like squeezing the heck out of an unbreakable balloon to suppress its natural shape.  You're never going to deflate it, but you will deform it, and all of its mass will creep out in tendrils to find alternative outlets.

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ORIGINAL: Najakcharmer

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ORIGINAL: plaything
It was also suggested to me privately that I seek counselling. Infact, I did, 10 years ago, when the conflict between this mindset and my religious faith were truly troubling me. I came away with a clean bill of [mental] health, and have since shed the more onerous aspects of my religion and began coming to terms with my particular form of admiration of Women.

Good for you.  So you believe that your current conscious adult choice to seek this lifestyle is a healthy one at this point?

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ORIGINAL: TigressFL

I know that after a few experiences with sissy boys, I have decided they are not for me.

Good luck to you!