This is a true story. The names have been changed, of course. They have to be. This is a story in the life of my good friend of mine, Heather, yet more the story of a young boy named Robert. It is for those of you whose mom or sister dressed you, or who have dressed another. i tell this life as it goes on, with permission and with care.
First off, i must tell you my relationship to heather. I know this lovely girl very well and we have come to relate on a level, fantastically. I love this girl. Something you must know about Heather is that she was born male and is still physically a male, yet at a young age, her mother dressed her as a girl and she now lives the majority of her life as such. But that is her story. We now focus on Robert.
Well, Heather being a normal teenage girl babysits quite a bit. One child that she babysits for, Robert, had an intriguing behaviour. Heather would often find him staring into her closet, at the clothes, as if in awe or wonder, as if he wanted to get a much closer look at them. Heather took notice and began to wonder, as did i.
Heather believed that Robert wished to try on the clothes, yet wasn't sure how to go about it. I agreed, it was a sensitive thing and the child is impressionable. Yet it is true that many crossdressers get their start in childhood. Yet web oth could be jumping to conclustions, that would be catastrophic if false. Yet with all the signs, how could we help but wonder?
We thought about it, what if Robert doesn't really have that interest even though it was obvious to us that he did? He could laugh or be insulted, even run to tell his mother about it. Heather of course not dealing with her own child could get in a lot of trouble if Robert's mom found out and didn't agree or if even Heather's mom found out. For Heather is a secret as well, and her mother would not approve of her doing so with another person's child. Yet what if Robert did have the interest? yet after being confronted about it, got defensive and unfomfortable? Not a good situation. And one must weigh in all possibilities. Yet, what if he cooperated?
We both decided to address this issue about Robert, not to just leave it alone. It ate at our curiosity. Yet to address it with care, attentiveness, and subtlety.
Then we devised a plan.
Heather was babysitting Robert. That day, she had taken out an old box of clothes she had when she was around Robert's age. (Her mom keeps everything.) She sat on the floor, sorting them out, folding them, holding them out just enough so Robert could see them well. And he did. He watched. Heather said,
or something to that effect. Robert looked a bit shocked, intrigued maybe. "I can't wear that. those clothes are for girls?" he said. Tread carefully, Heather. She replied that some boys do wear dresses. After some unreadable looks and miscellaneous questions and statements, Heather put the boz away and said it would be there the next time he came over if he changed his mind.
The next time Heather babysat Robert, they were sitting watching cartoons, and coincidentally there was one cartoon that came on with Bugs Bunny. You know how that cartoon character sometimes dresses female. Heather pointed this out to Robert, showing him that Bugs Bunny was a boy and dressed as a girl. Well, Heather then brought out the box again, and laid out some clothes, a whole ensemble actually. She then left the room to check her mail, yet partly to leave Robert alone with the clothes and see what would happen. It was at this time Heather emailed me, telling me what was happening. Robert was in teh room with the clothes, staring at them, slightly touching them.
Heather re-entered the room and casually asked if he'd like to try on the dress. Robert was reluctant, yet Heather could sense he wanted to. Later on that evening, Robert did put on the dress and seemd like he really loved it. Heather pushed, saying that the dress didn't look right with him wearing pants and for him to take them off and wear stockings instead. Robert shook his head no. I don't think he was ready right then.
30 minutes before Roberts mom, Sue, was to come and pick him up, Heather took the dress off him. Before he left, Robert asked Heather not to tell his mom about it. "Of course not" she said "and i'll keep your clothes for you here, okay?"
The next time Heather babysat Robert, nothing happened for a while. A half hour after his mom left, Robert asked Heather if she still had the clothes. Of course she did. That night our dear Robert got dressed fully as a girl.
Over the next few times Heather babysat for Robert, he showed interest in dressing up and did. And according to heather, is an adorable little girl, her hair kept a bit above her shoulders, so he looked a bit feminine hair-wise.
Then we realized we needed a name for our little girl. Oh she loved being a little girl. Only Heather and i knew about it, and therefore thought of her as "our little girl", our daughter, even though Robert didn't even know of me. Yet she needed a name. Well, i'd always wanted to name my child Elizabeth Anne, for an old friend of mine and because my middle name is anne. Heather's middle name is Anne as well, so we decided to keep it "in the family" so to speak. And now our Robert, is now our Anne. She doesn't like the nicknames Annie or Anna however, just Anne. :;smyle::
Anne is an adorable feminine child. One time, heather took her outside into the backyard. Anne was reluctant, but ended up loving it. And once, they checked the mail all the way at the end of the driveway. More and more Heather babysat for Anne. "I thinkRobert's got a crush on you, Heather. He talks about you all the time," Sue said. If only she knew ::smyles::
One day, Heather was babysitting Anne, Sue called and asked if her son could spend the night instead of picking him up. Of course it was all right with Robert. Heather checked with her mother because heather's mother's job often kept her overnight, and she said it was all right. Oh Anne and Heather were going to have some fun!
That night, Anne was given a luxurious bubble bath and dressed up extremely feminine. Heather even did her makeup. Anne loved it. The same thing happened the next day, but this time, Anne would undergo something unexpected, a kind of "test"
The sound of horse hooves came up the driveway. It was two of Heather's neighbors, other teenage girls, just paying a visit. Anne had three choices. One, she could go and hide until they left. Two, she could run and change back into a boy. Or three, she could stay and hope for the best. Anne chose to stay.
The neighbors stayed for a little while, and absolutely adored the little girl that Heather was babysitting! They didn't notice anything odd and even Heather was surprised at how feminine Anne could be. Anne passed her "test", oh how proud we were!
Then one day the most unexpected thing happened. Sue went over to Heather's house to talk to her, she had left Robert over at a friend's house so that she could talk to Heather alone. It seemed as if Sue had found out about what had been going on.
Sue asked Heather if she had noticed anything strange about Robert. Sh=ue said that she found Robert a lot of times looking through the little girl's section in catalogs and looking through her own closet. Heather suggested that maybe Robert likes the little girls in the catalog. "i thought that too, but it wouldn't explain anything about the clothes," Sue said.
Heather was shocked! Turns out that Sue had been thinking of letting her son try onthe clothes, but came to Heather for some reason. Personally, i think she was looking for some reassurance, or maybe Robert actually did tell his mom. Ah, Heather did reassure her and said the statistic of 10% of children under the age of 12 who were born male, live either full time of part time as a girl. Sue seemed to smyle.
Now Heather was faced with a decision, to tell Sue or not about what had been going on. I told her that she shouldn't, it could only complicate things and change Sue's point of view on the whole situation. Though Heather chose not to speak of it, because of her promise to our little Anne, our daughter.
ah, i'll just copy and paste what Heather last told me (changing names), it's easier this way ::smyles::
Here's what's happened with Robert's mother. She came over like she said she would. We talked some more, and she said that if she was going to do anything, that she would like to do it at her house, not that she was intending to. I went to my room and came out with a large bag filled with a fw things that I gave to her and told her that if she did decide to do anything, I would be more than happy to help, and if she did decide to do anything, what's in the bag would be of help and that they
should fit. The bag contained two dresses, a slip, two pairs of panties, two pairs of tights, a pair of black maryjane shoes, and two nightgowns. She looked through it and put everything back in with a smile on her face. When she did that, I told her that I wouldn't say anythng to anyone, and what she decided to do with the clothes was her business. Now the dresses were ones that Robert has never seen before. I am really curious about what may or has happened while I was gone. (so am i!) .
This section will no longer be updated, but will remain up for the sole reason that this site cannot be what it is without it. It can no longer be updated because my very precious Heather and i are no longer holding correspondence. She is gone from my life. If any of you knew her, it would be greatly appreciated if you would help in finding her; she touched so many lives. For more information on this... And now, the story:
Intro
In the Beginning...
The First Time
The Name:
The Neighbors
The Mother 
Introduction
In the Beginning...
The First Time "These are my old clothes. Aren't they pretty? My mom's thinking of throwing them away. You know, you could have them if you want. I think they could fit you"
'okay.'
The Name
The Neighbors
The Mother "Heather dear, be honest with me. Ane please don't tell anyone - especially your mother - about this, but do you think, it would be wrong with me, to dress Robert up as a girl?"
Yet the story is still continuing and i'll keep you posted as soon as heather tells me what's going on!! ::smyles::
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