Timmy's Confession
by
Pamela (
[email protected])
Harriet regarded her lingerie drawer. Her husband, John, was nearby in
the bathroom brushing his teeth getting ready for bed. They had been out
that evening at a dinner party with friends down the block. When they
had gotten home their 10 year old son Timmy was sleeping peacefully in
his bedroom. Ever since he had been eight they had felt OK to leave him
without a sitter if they were just a few doors away in the neighborhood.
It was a very safe community they lived in. There had been nothing amiss
in the house when they had come home, except now, when Harriet had taken
off her slip and had folded it neatly and was about to put it back in
the dresser drawer. She noticed that something didn't seem right. The
problem wasn't necessarily with her bras and panties which looked pretty
much like she had left them. No, it was her slips. She could see that
the top slip on the pile was not folded as neatly as she always folded
them.
She picked the slip up and let it open up. It had definitely not been
folded correctly. Timmy must have touched it, there was no one else who
could have. Probably some adolescent curiosity was creeping into him now
that he was approaching puberty. Hopefully this would be a one time
event and she had better not get worked up about it - though she didn't
like the thought of her son poking around in her lingerie drawer.
***
Three weeks later the incident was out of her mind when she came home
after a bridge night with other neighborhood friends, to discover that
her dresser drawer was not fully shut. It was just a tiny bit ajar, but
she was more than a little bit obsessive about shutting drawers so she
didn't think she could have left it open. She looked inside the drawer
and saw that her bras may have been touched and so too her panties and
slips. "Damn," she thought, "that Timmy is getting out of hand." She
then opened the closet to put away her dress and noticed that a pink,
cotton sundress that she rarely wore was hanging a bit askew on its
hanger. Harriet sat down on her bed in a state of shock. John walked
into the bedroom and asked her what the matter was.
Harriet shook her head and told him "nothing," it was just her stomach
that felt a little bit flippy floppy.
"I hope you aren't getting sick," he said.
"Oh no, it's already passed," she said. She had decided that she had
better not tell John. Surely he would wake up Timmy in a tirade of
anger. It would be too ugly. She would have to handle this herself.
***
That week Harriet went to an electronics store and bought a tiny
wireless spy camera and had the salesman explain to her five times
exactly how it was to be used; especially how to record and send the
video to her computer. Later that week, while John was at work and Timmy
was at school she set up the camera on the top of a picture frame in her
bedroom so it had a sweeping view of her bed and dresser. It's not
spying she said to herself, not like it would be if she put it in
Timmy's room. She hoped against hope that the camera would not turn up
anything of interest.
The first opportunity she had to catch Timmy in the act of invading the
privacy of her bedroom and clothes was that Tuesday. Every Tuesday and
Thursday Harriet worked part time at the local school district in the
central offices until five in the afternoon. On those days Timmy let
himself in after school at three and was alone until either Harriet or
her husband came home. Before she left for work that day, Harriet turned
the camera on and set the timer to begin recording at three.
When she came home from work that day, fearful of being caught either by
her husband or Timmy, she made no attempt to look at the video. Instead,
she waited until the next morning after Timmy left for school and John
had gone to work and the house was empty. She turned on her computer and
began playing back the video file. For 15 minutes she watched a fixed
view of the room and then suddenly the bedroom door opened and Timmy,
naked, tiptoed into the room. She heard him say "mom?" as if double
checking that she wasn't somewhere lurking in the shadows. She hadn't
seen him naked for a half dozen years and her heart tensed with
affection for the thin little figure she saw. His penis was a tiny
little thing and she watched as he walked to her dresser. He opened her
bra and panty drawer and she watched in a state of disbelief as his body
tensed and seemed to convey a degree of excitement equal to that if he
were to have opened a long lost chest of pirate gold.
He used one hand to lift up the top few bras and with the other took out
a pink bra. It was her only pink bra - actually she hadn't worn it for
years. It was a bra she had gotten when she was younger and worried
about being sexy. Now she preferred more functional bras that were more
comfortable to wear. The pink bra was a bit tight on her, her breasts
had filled out a little with age. If she remembered correctly the bra
probably had a B cup, not the C she wore now.
She watched as her son almost comically put on the bra. He clearly had
no clue how to do it correctly. Once he had it on she saw him take
panties and very carefully stuff them into the cups. Next he took out a
panty from the very bottom of the pile and put it on. It was a faded
pink and almost a rag. His little penis pushed ever so slightly against
the nylon fabric. Abruptly, Timmy closed the drawer and opened the one
below. She wondered what he would do with her hosiery drawer, put on
pantyhose? Instead, he took out an old girdle of hers. She had even
forgotten she still owned it. It had a shiny satin front panel in a sort
of diamond shape and an open leg style with a side zipper and a set of
three garters on each leg. Timmy slipped into it, zipped up the side,
and then lay down on the bed. He lay there quietly without moving and
she watched his face as it softened and relaxed. He crossed his arms
across his chest below the bra. He looked like a thin, gentle little
girl wearing her mommy's clothes. Harriet felt herself tearing up and
becoming deeply sad.
She had expected to see Timmy masturbating but he didn't. He just lay
there looking blissful and then also forlorn. The full impact of the
scene slowly dawned on her. Timmy wasn't raiding her drawers for a
sexual thrill. No, he was pretending to be a girl.
After awhile Timmy got up and went to the closet. He put on the pink
sundress and lay down again on the bed Harriet watched as Timmy began
crying. Tears rolled down his cheeks. He suddenly got up and got a
tissue and went back to lying on the bed. Even though he was crying a
bit he looked blissful. It was heartbreaking to watch. After awhile
Timmy seemed to be having a dialogue with an imaginary person. His arms
moved in a delicate, graceful fashion. He had very pretty hands she
thought. Girl hands.
Harriet wondered what she ought to do. Clearly Timmy was getting very
careless. Maybe he even wanted to be found out. But his father would
become a force of nature if he knew what she was witnessing. He would
never understand. God knows what he would do.
Timmy got up and kneeled next to the bed and formed his hands in prayer.
She had a view of his back in his dress and if she hadn't known better
she could have mistaken him for a girl. In his tiny voice she heard him
say, "please God make me a girl. Please, please, please. I'll do
anything. Please God. Just this one little thing." Timmy dabbed at his
eyes with the tissue and blew his nose. He got up and lay down again on
the bed and Harriet heard him sobbing. In a few minutes he looked at the
clock on the nightstand and got up again. He removed the dress and put
it back in the closet and then did the same with the lingerie. She saw
him double check that everything was back in its place and then he
exited the bedroom.
Harriet got a tissue herself and dabbed at her eyes and blew her nose.
She thought back to how she had raised Timmy. It was true that she had
felt a twinge of disappointment when she had given birth to a boy. She
had been so convinced her baby was going to be a girl that it was a
shock to find out she was wrong. However, when she had first held Timmy
she couldn't have been happier that God had sent her a little boy.
Perhaps she unintentionally raised Timmy to feel like a girl, but if she
had done so she couldn't for the life of her see how she had done it.
John was a fully engaged dad. He was good with Timmy, played with him
often. They did occasional dad/son activities - things that mainly only
guys did. Timmy was not a momma's boy though she had always felt that he
was on the sensitive side of things. Sometimes it seemed like he cried
too easily like some girls did, but it had never been a real problem.
***
Over the next few days Harriet pretended in her dealing with her husband
and Timmy that all was well. She bent over backwards to seem happy and
relaxed while inside she felt a terrible, suffocating helplessness. She
didn't do anything to prevent Timmy from invading her clothes. She
worried that if she was to tip him off about knowing what he was doing,
then she would be stuck with a problem she didn't know how to handle.
The consequences of confronting him could unalterably change her
relationship with him and she could not stand the thought of that
happening. She also worried that getting caught in such an intimate
misdeed by his mother could lead Timmy to a lifetime of trauma.
A week went by and finally, in desperation, she arranged to have lunch
with her sister, Ruth, who was a couple of years younger, childless and
single. Ruth was a career woman in the fashion industry and she and
Timmy had a special bond that was only possible because Ruth wasn't his
parent. Ruth was very fond of Timmy and Timmy looked up to her.
Over lunch at a chic restaurant in town, Harriet said, "I asked you here
for a purpose. You see I have a problem."
"You know I'll help any way I can. Is it with John?"
"No, no, it's with Timmy."
"Timmy!" Ruth's face which had formed into a frown in anticipation of
hearing that John had been cheating on her sister now turned to one of
genuine worry and concern.
"What's the matter?" she asked, fearing for the worst. She couldn't
imagine that Timmy would be a drug taker, or misbehave at school. She
wondered if he had come down with a terrible illness.
"You have to swear to not tell anyone anything I say here. Especially
John and certainly not Timmy!"
"Sure Harriet. You know I never would betray your trust."
"Good. Well, you see, I've discovered that Timmy dresses up in my
clothes. My bras, my slips, my panties and a dress. Even my old girdle."
She went on to describe the initial evidence and then about the camera
and Timmy's prayers.
Ruth listened with her mouth agape, every so often saying, "oh my!"
Harriet had fought back tears as she spoke and Ruth reached out across
the table and held her sister's hand. "I haven't confronted him or even
done anything like lock my bedroom door. I didn't want to get John
involved or cause Timmy to freak out. So what can I do? What should I
do?," Harriet said.
"Oh my gosh," Ruth said, "I need to think, it's so surprising. I thought
you were going to say he was sick or something. Well, I guess I agree
that you don't want to tell John. Bless his heart, I doubt if he could
be at all helpful in this situation." Ruth was thinking what advice she
ought to give. She imagined Timmy in a bra and girdle and dress. Girdles
were so uncomfortable, but if you wanted to be feminine she supposed it
was right on up there with a bra. "I guess we have to believe that what
he was praying to God about is true. He sees himself as a girl. From
what I understand he'll probably always feel that way. It's indelible. I
don't want to make you cry again but I think you have to accept this
truth the same as if he grew a third arm. Denial or ignoring it will not
help, but I agree that confronting him might not be the best thing to
do. It's probably a good idea if he can be coaxed into taking control of
his own situation."
"How can we do that?"
"That's a good question. He needs to tell you on his own free will that
he's been sneaking around in your drawers and why. That's exactly it! We
need a confession. It would take him from being just a naughty kid, that
John would clobber if he found out, to a kid who is looking to his
parents for help with a problem. I mean I don't think that John would
kill him if Timmy confessed to him his desire to be a girl. Would he?"
"You're right. Even if he did initially get mad, he'd soon see he was
wrong and apologize. I give that much credit to John."
Ruth scrunched up her face in thought and then said, "but perhaps that's
going too fast. Maybe just a confession to you would be a good start. I
can't imagine Timmy standing in front of John telling him he was a girl,
but with you I could see it."
"But then what?"
"We could see how this goes and then make up a new plan later. For the
moment you want to stop him from raiding your clothes and you want to do
it with the least trauma. That says that we need to leave John out of it
for the time being with good justification. So the problem becomes how
could we get Timmy to confess to you?"
"Someone else would have to convince him to tell me what he was doing,"
Harriet said.
"Exactly," Ruth said. "You could let me discover him cross dressing. It
would be a bit traumatic for him, but much much safer, nothing as bad as
having you find out."
"But it could ruin your relationship with him."
"I don't think so. It might even draw us in closer, particularly if he
saw that I wasn't condemning him, just trying to set him on an honest
path. It could help him to maintain his self-respect throughout this
ordeal."
"OK, but how could we do it? You can't barge in on him at my house."
"Maybe you and John could take that little jaunt to Puerto Vallarta you
always talk about to reenact your honeymoon and I'll watch Timmy at my
place. It seems like a safe bet that he'll invade my lingerie drawer if
I'm at work and I'll try and catch him in my bedroom by coming home
early."
"And then what?"
"Then we can have the big conversation in which he tells me the whole
story of his cross dressing and wanting to be a girl. I'll tell him he
has two choices: if he intends to cross-dress again, then before he does
so, he has to first confess to you his desire. If he doesn't ever cross-
dress again, then he doesn't have to say anything and I'll promise to
keep it a secret forever."
"But we know he won't or can't stop."
"So we can be pretty sure that he'll end up confessing his desire to you
and then you can make sure that he doesn't go into your dresser drawer."
The two ladies thought about the plan and discussed it further. "I think
it's a great plan Harriet, because it will get you involved in a
positive way, on his side. It gives you some control."
"I agree," Harriet said. "So instead of me confronting him, he'll never
know that I know what he's doing and he'll eventually come to me with
his problem. That sounds great. I'll talk to John tonight and see if we
can get away soon."
***
A few weeks later with Harriet and John away on their second honeymoon,
Timmy moved in with his Aunt Ruth. It was the spring break at school and
Ruth planned to take a day or two off from her job to be with Timmy. He
came on Saturday and over the weekend they did many fun things together
like visit museums and shopping and even went to movies they could both
enjoy at the Cineplex. To outward appearances Ruth could find nothing
about Timmy out of the ordinary. In fact, their mutual fondness for each
other made for a delightful easygoing time.
Ruth stayed home from work on Monday morning and at lunch time said she
had to go into the office for the afternoon to take care of some
important business. She expected to be home at 5 in time to make dinner.
Timmy assured her, a bit too eagerly she thought, that he would be fine
being alone by himself. She had to laugh to herself thinking what kind
of entertainment he probably had in mind.
Ruth left the apartment and went to work. She knew she would feel better
in the long run if she didn't have to lie about having been at work that
day. At 3PM, two hours earlier than she had said, she headed back home
to see what she might see. The reality of sneaking in on Timmy was much
harder than her fantasy about what it would be like. The fact of the
matter was that she was so fond of him, it was painful to contemplate
the embarassment she would cause him by catching him in the act. But she
had to do it since it would be better in the long run for Timmy than to
do nothing.
She quietly entered the apartment and looked around. Timmy was not in
sight and everything looked pristine, just as she had left it. Her
bedroom and the guest room where Timmy was staying were across a
carpeted hallway from each other. Ruth tiptoed through the apartment
toward the hallway. When she got to the door of her bedroom she saw that
it was part way ajar even though she had made sure to close it before
she had left. This was exactly what she imagined she was going to find.
Her plan now was to call out to Timmy as if she expected to find him in
his bedroom while simultaneously entering her own. That way she would
look completely innocent of having snuck in to catch him.
She braced herself for what she might find in her room. She counted to
three and then pushed open her door, backing in and calling out "Timmy?"
She heard a shriek behind her and as she rapidly swiveled around she was
just in time to see Timmy spread out on the bed wearing her bra and
panties. He leapt up, arms flailing in the air as if to block her view
and ended up crouching on the floor next to the bed in a fetal position.
He sobbed and wailed uncontrollably and struggled to get the bra off.
She noticed that one of her prettiest slips was lying on the bed nearby.
"My God Timmy, I wasn't feeling so good so I came home early. How could
you do this? How could you sneak into my bedroom and open my drawers and
wear my clothes?"
Timmy managed to take off the clothes. He put them on the bed while
hiding his nakedness. "I'm sorry, Aunt Ruth!" he wailed.
She picked up the bra, it was one of her everyday bras. The panty was
light blue with several rows of ruffles across the bottom. It had once
been part of a Halloween costume. "I'm putting my clothes back in my
dresser. I'll turn my back and you can run back to your room and get
dressed. Then I want to meet with you in the living room!" She said this
with as stern a voice as she could muster.
Timmy hurriedly got up to do as she ordered and as he did so he said,
"are you going to tell my mom and dad?"
"Maybe," Ruth said, "but first I want to talk to you, so get dressed."
***
A few minutes later Ruth and Timmy were sitting together in the living
room. Timmy had a fistful of Kleenex in his hand. Ruth couldn't recall
ever seeing the boy in such a miserable state.
"Look, Timmy, if the truth be known, I'm more upset at catching you
sneaking around in my personal property than I am about you wearing a
bra and panties," she said, "not that I'm wildly happy about that
either."
Timmy seemed like he was trying to form some words but instead went into
a new convulsion of crying and blew his nose. Some snot dangled between
his tissue and nose and his eyes were bright red from crying.
"I don't know why you want to wear my bra, you're a boy aren't you? But
the thought of you sneaking around in my clothes is very disappointing
to me. It doesn't seem like the Timmy I know and have always loved. What
is that all about?"
Timmy calmed down enough to say, "I know I'm gross and disgusting."
"You're saying that to stop me from punishing you, aren't you?"
"No!" he shrieked.
"OK, Timmy, I really want to talk to you about this, not just punish
you. So tell me why you did it."
"I don't know why I did it."
"You'll have to do a lot better than that," Ruth said sternly. She
wasn't going to let him off the hook easily. "Start with why you snuck
into my room."
"I guess I thought that if I just borrowed your clothes for an hour and
put them back that you wouldn't notice."
"OK, I can figure that part out myself. But what made you think to do it
in the first place. The first moment alone from me and all of a sudden,
boom!, you're right into my clothes."
"I just was curious," Timmy said.
"Curious? Look, young man, I'm expecting a lot better answers than
that," Ruth said. "We're not going to leave this room until you explain
why. And if I'm not happy with your explanation, I'll definitely have to
tell your parents. For all I know you sneak into your mom's bedroom
also." She was being harsher than she really wanted, but couldn't let
him do a Ronald Reagan on her.
After sniffling quietly for several minutes, Timmy said hoarsely, "can I
tell you something you'll never tell anyone else?"
"I suppose so. Sure, I won't tell anyone."
"Well, I remember once a few years ago seeing my mom wearing a bra. She
was in her underwear." Timmy paused and seemed to be fighting back tears
again.
"Go on," Ruth said.
"I don't know, later that night I was going to bed. I was lying there
and I remembered what I had seen and I thought that I should probably
have to wear a bra also. Just like my mom. But I know its gross and I
will never do it anymore."
"Wait, wait, back up, Timmy, and enough about it being gross! So what
did you do?"
"I thought about it." Timmy became silent.
"So today was the first day you finally decided to wear a bra?"
Timmy began crying in earnest again and Ruth said gently, "be honest
Timmy and I promise you that everything will end up being all right."
Timmy blew his nose and Ruth continued, "so, have you ever done what you
did here anywhere else?" Ruth asked.
"I've done this a few times with my mom's clothes."
"With your mom's clothes?"
"When she and my dad were out. I couldn't stop myself."
"Sneaking around in your mom's personal clothes cannot be nice!" Ruth
smiled inwardly. This had been so much easier than she had thought
possible. A full confession and she was sure that one day Timmy would be
admitting the same things to Harriet.
"I know. I've felt badly about it, but I couldn't stop myself. Like
today, I tried to stop myself, but then the thought that I could be so
happy made me do it and I told myself that if you didn't know I was
wearing your bra and panties it wouldn't really hurt you."
"Like if, suppose somebody borrowed your bicycle without asking you and
returned it before you knew it was gone. Would that bother you?"
"Yeah."
"Why?"
"Because they might hurt it."
"Yes. They put your things at risk without your permission to do so. In
the case of my underwear, it's the most intimate part of a person and I
feel like your violating my most private space."
Timmy fought back more tears and grew silent.
"Will you do it anymore?"
"No, no, like I said, I won't." Timmy said and as he did so he felt a
state of panic overtaking him. He loved his mom's clothes. He loved her
panties and bras and especially her slips. And that wonderful pink sun
dress. Lying in bed dressed like that was the happiest he had ever been
and he couldn't imagine not allowing himself to be that happy again.
"Won't do what?"
"I won't wear your clothes or my mom's clothes anymore."
"But what about wearing ladies clothes?" Ruth asked knowing that this
was the far bigger issue to get into.
"Oh, I mean I also won't wear girl's clothes anymore," Timmy said.
Ruth regarded him tenderly. That was certainly a promise he would never
be able to keep, but it provided the perfect opportunity to spring the
trap she had worked out with Harriet. "I'm willing to not say anything
to your mom and dad about what you did today so long as you promise me
one thing."
"What's that?" Timmy asked with some hope.
"That if you ever find yourself not being able to stop yourself from
wearing ladies clothes again, then you will first have a talk with your
mom about it."
"But I'm never going to do it again."
"I know you said that Timmy, but I still want you to make this promise
to me. Is it agreed?"
"You don't believe me!" Timmy said.
"I believe you Timmy, but how you feel today might not be how you feel
tomorrow. So, let me ask you again: if you do want to dress up as a
girl in the future do you promise to ask your mom first?"
"Yes," Timmy said.
"And you won't be sneaking into your mom's or my clothes or any other
ladies clothes any more?"
"No, I won't."
"Good then my lips are sealed. I won't tell your mom anything that
happened here today."
Ruth smiled at Timmy who still looked utterly miserable. "Let's not let
this incident get in the way of our having a good time this week," Ruth
said, "in fact let's go out to dinner tonight!"
Timmy looked depressed and still afraid to look her in the eye, but he
attempted to make a slight smile and said, "OK." It had to have been a
deeply traumatic experience for him, and now he had to go through his
mother to get to wear girl's clothes. Perhaps it would prove to be a big
enough obstacle to stop his behavior for a few weeks or even months, who
knew. Thankfully at least Harriet would now have the chance to take
control of the situation once it developed and that beat a blank as they
say.
***
Timmy and Ruth still had better part of a week to spend with each other,
and though initially awkward, within a day or two they returned back to
their usual relationship. At dinner one night, feeling a bit encouraged
Ruth said, "I just wanted to say that I hope you know that I love you
very much."
"I love you too Aunt Ruth," Timmy said.
"I'm glad. I want you to know that whatever happens in the future you
should know that I'll be there for you. I'll provide a sympathetic ear."
"You're not mad about my ..."
"No, definitely. Please. It's not easy growing up, finding ones way, and
I understand that. No one is free from errors of judgment or mistakes
that they have to learn from. You're a wonderful boy Timmy. I couldn't
imagine a nicer nephew to have."
Both she and Timmy became a bit choked up.
"As far as what happened here I won't say anything to your parents, but
like we agreed to, you should talk to your mother about your feelings in
case you get those desires again."
"I don't think I'll ever have to but if I do I promise I'll talk to her.
But don't you think she'll get mad or cry or something?"
"Your mother loves you very much. It's as close to unconditional love as
love can be. Whatever you say, as long as you're honest she'll be happy
to know that you confide in her and she'll try her best to do what's
right."
There was a lull in the conversation while Ruth assumed that Timmy was
thinking whether or not his mom would think that it was "right" for him
to dress like a girl.
"Do you believe in God, Aunt Ruth?" Timmy said, startling Ruth.
"Why, I suppose so, sort of." In truth she said what she said so as not
to prejudice whatever Timmy was about to say. "Why do you ask?"
"Sometimes I wonder about God watching me do things, like what I did you
know in your bedroom."
"I think it's what is usually called your conscience. That's the idea
that we try to do the right thing because we're watching ourselves and
we don't feel good if we do bad things."
Seeing that Timmy was perplexed she said, "it means that you have to
think about what you do, not just let God do all the watching and
thinking." She hoped that he would think about this the next time he
wanted to dress up as a girl.
"But sometimes it may be that I think it's OK and God doesn't. Or what
if God wasn't watching what happened?"
Ruth wondered what he was driving at. "I guess there are times when it's
hard to figure out what is right and wrong."
"And maybe God can make mistakes and then a person could do something
that looked to be wrong but was really right?"
Ruth wondered what powerful forces were bubbling up through Timmy's
inner soul. She felt sorry for Timmy that he had to come to terms with
who he was in a world where people had to be very much concerned with
what others thought about them. At his age it was even more difficult to
be one's self. On top of that her poor sister Harriet was going to have
to end up with this entire problem in her lap one day. It was a question
of when and not if. That, perhaps depressing news, was what she would
have to report to her sister when she got back from her trip.
***
The day after she returned from her marvelous vacation with John,
Harriet met with Ruth and got a complete accounting of what had
transpired. The two women were more convinced than ever that they had
done the right thing thus far. Harriet was unhappy to hear that Timmy
had invaded Ruth's private space, but glad that at least his
predilection to wear girl's clothes was out in the open. The next big
step in their plan was to await Timmy's confession if it should come.
The two women discussed what options they had when the time came to
respond to Timmy, and left a final decision as to what to do until such
time as it might be needed.
At first, Harriet expected Timmy to present himself to her with his
confession at any moment and she felt tense and irritable awaiting it.
Happily, the video camera showed that Timmy had definitely stopped going
into her room when she was gone, except one time when he entered, stood
in front of the dresser and then left. It saddened her to see the
agitated expression on his face but she was also glad that he had enough
courage to control his impulses.
Another week went by and Harriet was thinking less often about Timmy and
thinking that maybe he would never bring up the subject of his cross-
dressing. She and John had gone out to play bridge and when she came
home she had turned on her cell phone to see there was a text message
from Ruth saying it was urgent that she call her. While John was getting
ready for bed, she snuck down to the kitchen and did so.
"Timmy called me this evening," Ruth said.
"Really?"
"Yes, he asked me if he really has to talk to you about wearing girls
clothes."
"What did you say?"
"Well first I asked what happened, since the last time we talked he was
so convinced he would never want to wear girl's clothes again."
"What did he say?"
"He said that he was going crazy. He was sure that he was really a girl.
He couldn't see not dressing like a girl. I told him that it was good
that he had reached a clear vision of himself but that he definitely had
to live up to his end of the agreement. He sounded a bit depressed but
also resigned to what he had to do. So I just wanted to give you a heads
up. I think he might try and talk to you tomorrow."
"Thanks dear. You've been a big help."
***
Harriet passed a restless night worrying about what she would say to
Timmy. The best idea she and Ruth had worked out was to give him some
clothes and a restricted time when he could wear them. They definitely
agreed that it was not a good idea to refuse him the opportunity.
The next day when Timmy came home from school he was terribly
distraught. He was on the verge of crying and Harriet braced herself for
whatever it was that he was going to say.
"What's the matter honey?" she said with some alarm. She had decided
that without doubt she would never give Timmy any hint that she already
knew about what it was he would want to confess to her. Besides making
him lose trust in Ruth she wanted to give him every opportunity to find
himself, to find for himself what he needed to do. It was a very tall
order for a ten year old, but in her heart she felt this would create a
foundation of strength in him that would enable him to weather whatever
storms were to come to him later in his life.
"Mom," he said with a tremulous voice. The misery, fear, hopelessness in
his voice rent her heart into pieces.
"What happened Timmy?" Harriet said trying to sound like she would
normally sound in such an instance, "were you sent to the principal's
office!"
"No!" Timmy said.
"Come sit with me," Harriet said as she sat down on the sofa and
indicated the spot next to her. "Whatever has made you so upset!"
Timmy sat down next to her, then got up and got a few tissues and came
back. He blew his nose. "I have to say something. I guess its sort of a
confession."
"A confession?" Harriet said soothingly. She knew what was coming. It
had to be very hard for Timmy and it was definitely going to be hard on
herself.
Timmy looked at his mom. His face was so distraught Harriet wondered if
her leaving it up to him to broach this subject had been a good idea
after all. "You won't tell anyone?" Timmy said.
"Of course not Honey," Harriet said, "confessions are private."
Timmy hesitated a moment and then said, "I went in your bedroom a couple
of times when you weren't home."
Timmy fell silent and Harriet wondered if that was going to be it, but
just as she was about to ask him if that was the confession he said, "I
opened your drawer."
"Which drawer?" Harriet asked.
"The one in the dresser, where you keep..." His voice had gotten husky
and he began to cry.
"Where I keep what?" Harriet said. She had decided to play as dumb as
possible.
"You know your lady stuff."
"You mean my blouses?" She kept them in the bottom drawer of the
dresser.
"I mean where you keep your underwear." The last part of the sentence
was barely audible.
"You mean you looked in my underwear drawer where I keep my bras and
panties?"
Timmy shook his head up and down and through his tears said, "yeah, but
I also touched your stuff."
"Touched?"
"Put some on."
"You wore my bra and panties?"
"Yeah," Timmy said and lapsed into a crying fit.
"Why are you telling me this?"
"Because, Aunt Ruth ..."
"Aunt Ruth? What has she got to do with this?"
"Mom! She caught me doing the same thing at her house and she said..."
"Wait a minute!" Harriet said. "The same thing?"
"Yeah I was wearing her bra and panties and she came home early and ..."
"She told you to confess what you had done?"
"Well, actually, I told her that I had worn your bra and panties too.
And she said that I wouldn't have to confess if I promised I would never
do it again."
"So you did do it again?"
"No, I didn't but mommy..." Timmy started to cry with large upheavals of
air coming and going from his lungs.
"Calm down," Harriet said and she put her hand on his slight shoulders
and pulled him toward her so his head was in her lap. She looked down at
him as he struggled to regain control of himself. It was so hard to find
oneself she thought. What can a parent do, it was something everyone had
to do for themselves. "You need to tell me why you wore my and your
aunt's bras and panties."
There was a long moment of silence and she felt Timmy's breathing
becoming more regular. He was a very attractive child and maybe she had
never noticed that he did have some feminine traits. His skin was soft
and delicate like a girl and of course the silky smoothness of his
straight blonde hair. His arms were also thin and undeveloped like that
of a girl.
Finally Timmy said, "Mommy?"
"Yes?"
"Do you think that God could make a mistake?"
Harriet felt a wave of tears hit her own eyes. "What kind of mistake?"
she asked.
"Maybe there was a little girl that He was creating and then by accident
she ended up being a boy?"
With all her self-control not to breakdown Harriet said, "is that little
girl you?"
"Yes, mommy."
Harriet stroked his head and she let some tears come down her own
cheeks. "I guess God could make a mistake, but maybe it's just that God
makes some people very very special. People that can be both girls and
boys at the same time."
She could sense that Timmy was thinking intensely about what she had
said. "How can someone be both a girl and a boy?" he said.
"When you put on my bra and panty did you feel like a girl?"
"Yes. Mommy, I also wore your slip and your dress. Your pink dress
and..."
"and they made you feel like a girl."
"They make me feel happy. They make me feel like I don't know, it's just
that I know I want to feel that way all the time. I don't want to be a
boy."
"Is it you don't want to be a boy or is it that you want to be a girl?"
"I think it's that I feel I am a girl and that's why I don't want to be
a boy. I don't want to look like a boy since I don't think I am one."
Harriet felt exhausted. Where should she go from here? It was not
obvious to her. Can she condone this and even if she did how much must
she be a part of Timmy's life? After awhile her mind cleared a bit and
she said, "you've not yet told me why you're confessing. If you haven't
done it again, why confess?"
"I promised Aunt Ruth that if I wanted to wear a bra again that I should
confess. I mean I promised that I'll never sneak into your clothes again
but I want to wear a bra. So what can I do?" He turned on his back and
was looking up at Harriet. She looked down at him. She had all the power
right now. His fate hung on what she decided to do.
She hadn't held him in this position since she last breast fed him. It
had been a wonderful pregnancy and she had loved being a new mother. The
connection she had felt as Timmy suckled her was some of the happiest
times of her life. From time to time she wondered if maybe she would
have preferred having a girl if just for the reason that they could have
intimate talks about girl stuff. She had even thought sometimes that
John would always have a slight advantage over her since there would be
times when he and Timmy could have man to man talks that she could not
be part of. But now Timmy had upended the cart. Should she force him to
be a boy or should she help him to be a girl? Could she force him to be
a boy even if she wanted to?
"So the problem is that you won't sneak into my room any more but you
still want to wear my bras and panties?"
"It doesn't have to be yours."
"You just want to wear bras and panties, it doesn't matter whose they
are?"
"I feel like a girl mommy and if I can dress like a girl then I'll feel
better."
She stroked his forehead. How tortured he must be inside that he risked
everything by confessing. "I need time to think about this. You know
your dad has to be involved in this."
"Don't tell dad!" Timmy cried out with fear and sat up.
"How can I not tell him?"
"You promised that you wouldn't tell anyone about this."
"Yes, I won't, but it's a separate issue as to whether or not you can
wear girl's clothes here. You're asking me to approve that without your
father knowing about it. Is that fair to your father?"
"Then I won't do it mom, so you won't have to ask him."
Of course she wasn't really planning on telling John and that was one of
the biggest parts of her dilemma. It was easier to go along with Timmy
and give him a bra than to let John in on the secret, even though she
hated the idea of having a marriage where she kept secrets from her
husband. Either way she figured John would get hurt. Perhaps there was
less pain involved in the long run if she kept him in the dark. Timmy
was her son, her own flesh and blood and why should he suffer needlessly
for something as silly as a bra. It seemed wrong to her. "I'm not
planning to talk to your dad, but I need some time to think about this
little talk. You'll have to wait for an answer. I'm sorry."
Timmy looked confused, it wasn't what he was expecting. He lived in a
world of instant gratification. He felt tears coming on again. Harriet
said, "the good news is that I haven't said no, so you might as well
not be sad."
"OK, mommy, thank you," Timmy said.
"You don't have to thank me," Harriet said.
***
A few days later Harriet met Ruth for lunch and related to her what had
happened. "What should I do?" she asked Ruth.
"Whether or not you should aid and abet the enemy?"
"Exactly, as well as risk John's eternal anger at me and maybe Timmy."
"I've done some reading about this," Ruth said, "and I think its true
that Timmy will for the rest of his life long to be a girl. It's never
going to go away. So that's a reality that I think helps ease the
problem."
"How so? It seems like it means that there is no way out."
"What I mean is that it doesn't matter if you give Timmy access to bras
or not. He's going to always want them. He won't want them more or less
because you gave him one. It's like worrying about whether or not
morphine can turn the terminally ill into addicts."
"That's a ghastly analogy Ruth but I see your point. If I help make
Timmy happier that's the only effect of my helping him. I haven't really
corrupted him."
"Exactly my way of thinking. And it provides some cover against John if
he ever finds out about it."
"But John will believe that it's just a matter of self-control for
Timmy."
"You can tell John that you couldn't stand the thought that he would
think less of his son, so you kept it from him knowing that it was
futile to prevent it."
"John will still get mad."
"Your fall back position is that you love them both very much and you
did the one thing that was sure to keep them both loving you. If you
told John, his reaction to Timmy would cause you to think less of him
besides causing Timmy to think less of both of you. So its win-win vs.
lose-lose. Take your pick."
"John will be mad because he'll think that he could have changed Timmy."
"But you'll be able to point out how happy Timmy has been with the
freedom to dress like a girl, besides the fact that John hadn't even
been suspicious it was going on."
"What would I do without you Ruth?"
"That's what sisters are for. I love Timmy also and I love you and I
sincerely think that it's also best for John."
"OK. What kind of clothes should I get for Timmy?"
"It's probably best if you work that out with Timmy," Ruth said.
"I'm sure you're right."
***
The next opportunity to be alone with Timmy, Harriet gave him her
answer. "I've had some time to think about your confession and I've
decided that I'm not going to stop you from pretending to be a girl if
that's what you want."
Timmy, who had looked terribly nervous broke out into a big smile and
hugged his mother.
"There are some important rules however. First and foremost is that you
must never ever dress as a girl with your father in the house, or about
to come home or any other circumstance where he could catch you."
Timmy nodded his head up and down excitedly. "The second condition is
that you can only dress like a girl in the house. Never outside."
"Thank you mom!"
"Do you agree to the conditions?"
"Yes mommy, I'll never dress as a girl when daddy is home or about to
come home and I'll never dress as a girl outside the house."
"Good. So this is how it's going to be. We'll sit down at the computer
and we'll do some shopping on line and have the clothes sent here. When
they arrive you'll keep them hidden in your room."
Timmy started to cry with joy and buried his face in his mom's neck and
held her as tightly as he could. "We'll keep your girl clothes in the
old trunk in the back of your closet and pretend, if anybody else should
open it and ask why there are girl's clothes inside, that the clothes
were left there for us to hold by Mrs. Milbauer your nursery school
teacher - but she never came to get them."
Timmy looked so blissful Harriet felt increasingly confident that she
was doing the right thing.
"When can we pick out some clothes?" Timmy asked.
"How about right now?" Harriet said, and she fetched her laptop computer
and brought it to where they were sitting.
"I wonder what a good site is for girl's clothes," Timmy asked.
"How about we look around at J.C. Penny, they have a good selection, and
we've bought you jeans there before."
Timmy put his thin arms around his mom and hugged her. Harriet felt a
joy in her heart as powerful as the day Timmy was born. In some ways,
this afternoon marked a second birth for Timmy. He could be counted upon
to ever more deeply enter into his girl self and as he did so, Harriet
would acquire a daughter. As they waited for the machine to power up
and make the wireless connection, she also felt a sudden sense of
foreboding. Perhaps she was crazy for not remembering first and foremost
that this plan was terribly fraught with danger. Timmy might get caught
by his dad wearing girl's clothes, or he might accidentally act the part
of a girl in front of his dad. She would have to be ever vigilant, a
thought that made her question the folly of what she was about to do.
When the J. C. Penny website came up, Harriet said, "let's see where we
should look." On the top they saw "Women" "Lingerie" "Juniors" and to
the right "kids + baby". Harriet said, "I'm looking for girls. You're
too young for "Juniors" so I suppose it must be in "kids + baby". Timmy
looked on with complete absorption. Harriet clicked on "kids + baby" and
saw on the left "girls clothing" and clicked on that. Some pictures of
different categories of clothes came up that gave them a choice of
directions to go. Timmy saw that one of them said "dresses" and had a
picture of a bright pink dress. He couldn't wait to see if his mom would
buy that dress for him.
"Let's start with "underwear"," his mother said and she clicked on an
icon of some gaily colored panties. Icons of bras, panties and socks
came up . "We might as well first start with bras," she said and she
clicked on "bras." Timmy was in a state of ecstasy when he saw the
selection that appeared. The first was called "Maidenform 2 Pack
Beginner Bras" for $12.00. They were pink and white and Timmy
reflexively squeezed his mothers arm when she said, "oh, these are very
pretty! Would you like a package of these bras?"
"Yes mom!" he said.
"We need to decide on a size."
"How do you do that mom?"
"I'll get a tape measure and see how big you are around the chest,"
Harriet said and got up and went to get one from her sewing kit.
Timmy looked at the other choices for bras. One of them looked to be for
older girls, anyway, it looked like the bra he had worn at Aunt Ruth's
house. It was called "Maidenform One Fab Fit Bra."
When Harriet came back she had Timmy take off his shirt. She then
encircled his chest with the tape measure and read off "29, 29 and a
half inches." That means that your bra strap size would be 30.
"30?" Timmy said.
"You always round up to the next even number. Like I'm a 36 but if you
measured me I'd be a 35 or so."
Harriet was enjoying herself and she made a mental note to tell Ruth
about this experience when she got the chance. Talking to Timmy about
bras reminded her of the kind of conversation she would have wished to
have had with a daughter, if she had had one.
Harriet clicked on size and selected 30. Below that was a button to
select a color that revealed there was a choice between white and white,
or pink and white. "How about the pink and white bra, it's a little bit
prettier," she said.
"OK," Timmy said.
"It's so funny, they don't even ask for a cup size. It's just 30, since
they know girls wearing a beginner bra don't really have a cup size."
Timmy looked confused and Harriet explained, "it's not just the distance
around the chest, it's also the size of the you know whats that go
inside the bra. The cup size reflects how big they are. A is the
smallest cup usually, then there is B and C and even larger ones for the
really big girls. Like here, you see this other bra," she said
indicating the Maidenform One Fab Fit bra, and she clicked on that.
"See, if we click on 30 for the size then it asks us to enter a cup
size. Here, it shows only the one cup size A since this bra is really
just for young girls. They don't even make it in larger cup sizes."
Timmy was looking at it with such intensity that Harriet said, "would
you like one of these too?"
"Can I?" Timmy said.
"Sure, dear, but we have to choose a color for it, black, nude, pink or
white?"
"What do you think I should get?" Timmy asked.
"How about we just get you a white one and a pink one?"
"Great, mom," Timmy said appreciatively.
"So we'll have four bras altogether, and now we'll look at panties."
Harriet's mind raced along imagining what her relationship with Timmy
would be like once his girl clothes arrived. She would definitely have
to make sure to teach Timmy how to put on a bra and whatever other basic
girl knowledge he ought to know.
Harriet sent the browser back to the screen listing bras, panties and
socks and clicked on panties this time. Several different styles
appeared. Each of these came as packages of 5 panties and without asking
Timmy clicked on the one that said it was bikini style. A picture of 5
gaily colored panties appeared. "These seem nice, don't they?" Harriet
asked.
"They're very pretty," Timmy said, "and isn't it so cool that they come
in so many colors."
"I guess that's true. Your boy underwear has been white, but girls often
like to have lots of different colored panties. Anyway, the bikini cut
is probably the nicest for you and we'll stick to that."
Timmy looked at the other pictures and said, "what about hipsters?"
"I find them to be cut too low and kind of uncomfortable. I don't know,
maybe later on we'll branch out."
"OK mom," Timmy said.
"Now we journey over to the socks department."
They proceeded to weave a path through the web site buying socks, some
skirts and tops and sandals. There were some nice dresses but Harriet
didn't sense they were exactly what Timmy had in mind so she suggested
they try a different website for them. They went to the J.C. Penny
checkout and ordered the clothing. Everything was in stock and in a week
they could expect it to show up at the door.
"Had enough for today?" Harriet asked.
"No!" Timmy exclaimed, "I'm happy to look at more dresses."
"OK, we might as well spend a bit more time, then you had better start
your homework."
They cruised around on the internet searching under the key words "girls
dresses" and came up with a nice website where they decided on buying a
pretty light pink organza over tulle, tea length dress with a full skirt
and cap sleeves. In the back there was a satin bow, streamers and
appliqu?d trim. Half the fun for Harriet was watching Timmy's eyes, the
size of saucers as he carefully examined each dress that they saw. She
was sure that she heard him gulp with excitement when he first saw the
one that they finally picked. The last thing they searched for and
ordered was some tights that he could wear with his dress and skirts.
Harriet had to admit to herself that she had thoroughly enjoyed the
experience. She truly was gaining the daughter she had never had. How
many moms out there had the fun of shopping with their daughters -
discussing which bra or skirt to buy - an experience she had never had,
and so completely unlike buying clothes for a son. Of course, facing
the reality of seeing her son dressed as a girl was another huge hurdle
that she would have to leap over in a matter of a week or two. For the
moment, however, she treasured the memory of sitting side by side with
Timmy peering at the girl's clothes and she would get to relive it in
detail when she told Ruth about it the next day.
***
The day the packages of clothes arrived, Harriet was at home and Timmy
was at school. She had been unsure of how she would feel when she first
looked upon the girls clothes she had bought for Timmy, but she found
herself pleasantly surprised, even happy that she had managed to get him
such a pretty collection of things. Some lingering doubts about the
wisdom of what she had done began creeping into her mind the closer it
got to the time when Timmy would be coming home from school. The reality
of having her son wearing girl's clothes and behaving like she had seen
from her spy camera was sinking in and she began worrying herself sick.
She would have to take the blame for having allowed him to pursue his
obsession and she could imagine John yelling at her: "How could you not
have known better? Turning our son into a girl? What terrible judgment
you have. I'll never forgive you for that!"
Suddenly nervous, Harriet thought that she should hide the clothes from
Timmy. In fact, it was not too late to call the whole thing off. She had
merely to tell John about Timmy's confession and then all would be over
for better or worse.
She called Ruth at work and told her that the clothes had arrived. The
pretty dress with the organza and tulle was just totally precious. There
was a cute built in starched crinoline that puffed out the skirt. It
would be incredibly darling. "But every time I think of Timmy wearing
that, I get cold feet. Do you think I'm doing the right thing Ruth?"
"Just keep focusing on the alternative," Ruth said. "Sometimes a person
has to pick between two tough choices and I think we've made the right
one. You know, in time, I hope that that becomes clearer and clearer,
even if now the reality of what you're doing seems scary."
"I hope you're right. I guess I'll give him the clothes and we'll hope
for the best."
"Call me tonight if you can and let me know how it went."
"I'll try."
***
As he had done every day since he and his mom had ordered the clothes,
Timmy ran home from school to see if they had arrived. Harriet greeted
him at the door and by the smile on her face he knew that they were
there. "Oh mom, I'm so happy" he exclaimed panting for breath.
Harriet had spread the clothes out on his bed and when he came up to his
room he looked at each and every package one by one. He held up the
organza dress and said, "it's so much prettier than I imagined! Can I
try it on?"
"Well you know the rules. You've got a couple of hours now until your
dad comes home, so go ahead and wear the clothes. That's why we bought
them."
"Thanks mom."
"If you have any questions I'll be in the living room. You can also come
down and give me a fashion show if you want."
Timmy laughed and then said, "there is just one thing I don't understand
too well."
"What's that?"
"I'm not so sure I know about how to put on an um..." He pointed to the
package of bras.
"Bras? Yes, I suppose you wouldn't know how to do it. Shall I help you?"
"Would you mommy?"
"Sure, take off your top," Harriet said and waited while Timmy took it
off. She opened the package of beginner bras and took one out and handed
it to Timmy. "It's best if I just tell you how to do it while you put it
on yourself," and Harriet proceeded to lead him through the technique
she used herself. "Look for the little ribbon on the front of the bra
and then hold up the bra in your right hand by its left end." Timmy was
so confused as to which was the left and right ends that Harriet finally
had to stand behind him and guide his hands. "If all mothers have to go
through such an effort with their daughters it's a miracle any girls
wear bras at all!" she laughed. Timmy smiled seeing that she was just
playing with him. Harriet continued, "now reach behind your back with
your left hand and catch the right end of the bra." Timmy twirled around
three times until he finally caught the end and Harriet roared with
laughter. She could barely control herself enough to say, "bring your
two hands together in front of your belly and clip them together. Very
good. Now you can swivel the cups around to the front and lift up the
bra putting your hands inside the straps on the left and right sides.
Excellent." Timmy now seemed to be getting the idea of what he was
doing.
"The last thing is to make sure that your breasts are caught comfortably
in the cups." She was tempted to show Timmy what that looked like in
her own case, since his cups lay flat on his small chest. However, on
second thought she wasn't sure it was such a good idea to undress in
front of her son and discuss with him how she filled out her bra. She
remembered that Ruth had told her how Timmy had said that his original
inspiration for cross dressing came from seeing her in her underwear.
The last thing she wanted to do was give him any more ideas.
Despite the absence of breasts, Timmy made a serious attempt at
capturing his own non-existent breasts. This time the effect was perhaps
a bit more sad than comical and Harriet said, "very very good Timmy. I
think you'll have no trouble putting on your bras from now on."
With the pretty bra on correctly Timmy ran to a mirror to look at
himself. "It's so pretty mommy, I love it."
"It'll be easier to get on with practice," she said. A first big
milestone in the life of her new daughter she thought: wearing her very
first bra. She thought back to when she got her own first bra and tried
to remember if her mother, Timmy's grandmother, had been excited about
it. She couldn't remember one way or the other, she had been so focused
on her own happiness of having passed through that transition into
adolescence.
"I'm going to first try on my dress," Timmy said.
"First put on some panties," Harriet said.
"I know mom," Timmy said blushing and indicating that she should leave
the room so he could change.
"OK dear, but I'm going to have to help you with the dress. It's got a
back zip," Harriet said and she picked up the dress, unzipped the zipper
and showed it to Timmy. "You'll have to put it on over your head and
then I'll zip it up for you. Come to me when you're ready."
Harriet left Timmy to himself and she went downstairs. So far so good,
she thought. It seemed like such innocent play for Timmy and he was so
happy. She smiled again at the remembrance of him struggling with the
bra. She would make a point of describing that to Ruth.
A few minutes later Timmy came down to the living room wearing his
organza over tulle party dress. "I put on some panties and the tights,"
Timmy said.
"I see," Harriet said trying to sound positive. The little stiff skirt
stood out around him and Harriet saw that he had also put on his low
heeled shoes. She got up and zipped him fully into the dress and said,
"why just look at you Timmy, it fits like a charm. One would think it
was just made for you."
"I love it mom," Timmy said and he walked slowly about the living room
with a dainty gentleness. Things inside him were opening up, some inner
need that came out into the open once he looked the part of a young,
pretty girl. Harriet felt a twinge of worry. Would it be hard for Timmy
to transition back to his usual self when his dad came home? Or in
school the next day?
"I hope you'll be able to be yourself when your dad gets home," Harriet
said and then realized that "yourself" could be interpreted either way.
"I mean your boy self," she corrected herself.
"Sure mommy, I promised you I would and I will. I don't want daddy to
know about this."
Harriet smiled. It was a relief: Timmy and she were on the same page.
***
That night she called up Ruth. "You can't believe how precious our
little princess of organza and tulle looks," Harriet gushed. "He's like
a little doll. More delicate and girly than you or I ever were."
Ruth laughed, "and everything fits?"
"Yes pretty well really. It's remarkable. He showed me a few outfits,
the shorts, skirts and tops all are lovely."
"What about the bras?"
"I was going to tell you. He asked me to help him on with it and I tried
to teach him. It was so cute and funny. We both were laughing."
"I can't wait to see him."
"John will be travelling on business in three weeks. He'll be gone a
week and you'll have to come over, that is, assuming that Timmy has no
objection."
***
The days went by one by one with Timmy spending a couple of hours each
afternoon after school dressed in his pretty clothes. At first he
favored the party dress but as time went on he branched out to
experiment dressing in a skirt and matching top. He became an expert at
putting on bras and stockings. A couple of times Harriet surprised him
with little gifts. One time it was pantyhose and another it was a slip.
One day she came home with a pink leotard, stockings, ballet slippers
and a cute little tutu. "I saw it in the shop window, and I couldn't
resist buying it for you, it's so darling," she told him. For the next
few days Timmy flitted around the house as a little ballerina.
After the excitement of the first week, Harriet noticed that Timmy would
come home from school, choose an outfit and then get absorbed in his
homework. It was as if he was defining normalcy in his life as being a
girl. During the two hours that he was dressed up, if Harriet talked to
him, Timmy seemed like a girl to her. It was a remarkable if subtle
transformation and it was not what Harriet had expected. She thought she
would always be looking at a boy play acting the part of a girl, but it
did not seem that way at all.
Harriet kept Ruth in the loop as much as possible about how Timmy was
progressing in the role of her daughter. She purposefully didn't tell
Timmy about his father's upcoming trip since she suspected that it would
be hard for him to contain his excitement and he would act strange in
front of his dad. A few days before the trip, however, John talked about
it at dinner and Harriet could see Timmy's excitement and she signaled
to him with her eyes that he had better be careful not to make his dad
think that he was anxious for him to leave on his trip.
Finally, on a Saturday morning, Harriet drove John to the airport with
Timmy coming along for the ride. The moment his dad said his goodbyes
and was gone, Timmy and his mom exchanged glances. They both understood
that this presented new opportunities for Timmy. Harriet felt like she
ought to try and rein him in somehow but she knew deep inside that it
would be hopeless. The horse was out of the barn and not likely to
willingly go back in again.
"Your Aunt Ruth will be coming this afternoon for a visit," Harriet
said.
"Oh, does that mean I have to be a boy?" Timmy said sounding a bit
deflated.
"Actually, it's up to you. Your Aunt did see you wearing her underwear
so I guess she wouldn't be too surprised if she saw you dressed as a
girl today."
"I won't mind," Timmy said and Harriet thought to herself "mark me
surprised."
"Can I mention it to her before she comes over so she won't be shocked?"
"Sure," Timmy said, "but..."
"But what?"
"But I wanted to wear my pretty white and pink dress today. Maybe she
won't like that."
If only Timmy knew how much Ruth wanted to see him like that! "Don't
worry. You look darling in that dress and I think Ruth will agree with
me."
Harriet glanced over at Timmy. He was smiling and happy. This was going
to be an enchanted week.
***
When they got back home from the airport Timmy made a beeline to his
room and took out the clothes he had been planning to wear for this
special day: his 30A cup bra, panties, pantyhose, his slip and his
organza over tulle dress. Now that he knew that Aunt Ruth was coming he
was more anxious than ever that he look his prettiest. It would be his
way of trying to explain to her why his claim that he would never wear
girl's clothes again had been wrong. He wanted to convince her that it
didn't make sense for someone who felt as entirely feminine as he did
should not dress as a girl.
When he was fully dressed he stood looking at himself in the large
mirror over his dresser. He still couldn't get over how much he loved
the organza dress. He turned sideways and looked at his profile. Though
it was nice to have a bra on that made a slight outward thrust over his
chest, it would be a lot nicer to have a more definite figure. Also the
time had come when he ought to wear some makeup. He went to his mom who
was busy in the kitchen and said, "can I put some panties in my bra to
fill out the cups?"
His mother looked at him and stopped herself from saying any of the
obvious objections: that it was silly and unnecessary. Clearly Timmy
would want breasts like any young girl would. She hadn't thought about
it before, but perhaps she would have to order him a couple of padded
bras. "Sure, I guess it's OK!"
"Thanks mom," Timmy said. Instead of rushing off he stood where he was
and finally said, "since it's a special occasion