CHAPTER ONE
"Are you sure you're going to be all right?"
Bobby Kingsley sighed, rolling his eyes. His mother could be so
overprotective sometimes. It really got on his nerves when she was like
this. He was seventeen years old, for crying out loud.
"Yes, mom," he said. "I'm perfectly capable of staying home by myself
for a few hours."
His mother, Rachel, poked her head into view from behind the wall by
the stairs leading to the second floor. Bobby could tell from her odd
stance that she wasn't fully dressed.
"It's not a question of what you're capable or not capable of," Rachel
said. "I just don't like the thought of you being alone all night."
Rachel was going out to meet an old friend from university. She didn't
go out much, but when she did, she liked to make sure she covered her
bases.
Bobby sighed again. "Mom, I'll be okay," he said. "Don't worry; I've
done it before, and I'll be able to do it again."
Rachel smiled, convinced. "Okay," she said. Her head disappeared behind
the wall as she went upstairs to get dressed.
A few minutes later, she came down the stairs and into full view,
showing off her clothes for her son.
"Well?" she asked. "How do I look?"
Bobby chuckled. His mother was wearing her best black dress; she had
put on her most expensive piece of jewelry (a gold necklace) and a
matching pair of earrings. Her dark hair was exquisitely styled - which
she had spent the last two hours doing herself - and she was wearing a
pair of black patent leather pumps with stiletto heels. (Bobby always
noticed the shoes; he had a thing for shoes.)
"You look great," he said. "Have a wonderful time."
Rachel smiled again and headed for the front door. "I'll be back in a
few hours," she said. "Here's twenty bucks for dinner."
Bobby got up off the couch and headed to the door to see his mother
off. When he got there, she was putting on her leather jacket (Bobby
shivered at the thought of it; he also had a thing for leather). Bobby
reached and unlocked the door, opening it for Rachel.
"Bye," he said.
Rachel gave him a quick hug, uttering her own goodbye, and walked out
the door. Bobby closed it behind her and watched her get into the car.
He heard the engine start, saw the car back out of the driveway, and
heard it drive down the road. It went around the corner and disappeared
from view.
As soon as Rachel was gone, Bobby moved away from the door. He headed
upstairs and to his mother's room at the end of the hall. Not bothering
to close the door, he went over to the dresser on the far side of the
room. Grabbing the handle, he could barely contain his excitement: he
had been waiting for this ever since Rachel had mentioned going out for
an evening.
Opening the drawer revealed a collection of bras and panties, most of
them black and silk. Sifting through the panties, Bobby pulled out the
sturdiest-looking pair he could find (he didn't want to tear anything)
and placed them on Rachel's bed. He also grabbed a pair of black
pantyhose and a matching bra. Closing the drawer, he moved over to the
closet.
Opening this, Bobby scanned the vast quantity of clothes hanging before
him. Looking carefully, he picked out a black pencil skirt that he knew
his mother had said was somewhat snug and laid it on the bed next to
the under-clothes. Going back to the closet, he grabbed a white blouse
with buttons up the front. This, too, he placed on the bed.
Getting down on his knees, Bobby grunted as he peered into the bottom
of the closet, underneath his mother's collection of skirts and pants.
After a minute, he spotted what he was looking for: a pair of stiletto
ankle boots with five-inch heels and a small platform. The back was
zippered, which made it easier for Bobby to fit in his feet, which were
slightly larger than Rachel's. Pulling the boots out, he closed the
closet doors and brought the boots to the bed.
Looking at the outfit he had laid out for himself, Bobby smiled.
Grabbing his shirt, he pulled it up and over his head, throwing it to
the floor. He quickly unbuckled his pants and kicked them off. Soon
joining them were his socks and boxer briefs. He was now standing buck
naked in his mother's bedroom.
He started with the basics: grabbing the panties, he spread his legs
wide and tucked his penis and scrotum between his legs. He reached
around his hips and felt for them, making sure they would not be
injured if he sat down too quickly. Making sure to keep his legs
tightly together, Bobby stepped into the silk panties and pulled them
up into place carefully, so as to avoid ripping them. He looked down at
his apparently smooth crotch and smiled: step one was complete.
Next on were the pantyhose, which, again, he was careful not to tear.
The feeling of them on his legs, pulling at his leg hairs, was
electric, and he was almost shivering as he pulled them up to cover his
panties. He carefully bent over to make sure the seam of the pantyhose
was correctly lined up with his toes.
Next he put on the bra, which was harder than he liked. He decided to
put it on backwards, without putting the straps over his shoulders. He
then spun the bra around carefully until it was in place and bent his
arms to place them in the straps. He couldn't bend far enough and his
arms began to hurt as he tried to maneuver into the bra. It seemed he
was a little bigger than he'd thought.
On top of the bra, he placed the blouse; he had no problem with this,
as it was easy enough to do up the buttons. Next, Bobby donned the
pencil skirt, pulling it up his legs and trying not to move or tear the
hose. He tucked in his blouse and pulled up his skirt all the way, so
that it fell to just below his knees. He tried to take a few steps and
found that his mother had understated the skirt's restrictiveness. He
could barely walk, though he didn't mind it. He liked the feeling of
tight clothes.
Finally, Bobby put on the boots. It was a little harder than
anticipated, because of the tight skirt, but he managed to do it.
Unzipping them, he placed the left boot on the floor and slipped his
foot in. Balancing on his other foot, he bent his foot up in the air
behind him and did the zipper up. It was another tight fit, but the
satisfaction was worth it. He then did the same thing with the other
shoe.
Bobby was now five inches taller; looking at himself in the mirror, he
found he couldn't see most of his face, which didn't bother him at all.
He hated looking at his male face, chubby and usually at least a little
hairy. His beard often grew quite quickly, and he sometimes let it as
part of a desire to hide his true ambitions of being female.
Not that he needed to do so: he was hardly feminine to begin with. He
had an average-sized waist, he was somewhat awkwardly built, and he was
not at all light on his feet. The only reason Bobby might have been
considered not manly was that he was very shy and timid when it came to
meeting and talking to people he didn't know. He found it hard to voice
his opinions sometimes, which often led to his ideas never being heard.
Thinking of all of these thoughts made Bobby feel sad, so he tried to
force them from his mind. Standing up a little straighter, and managing
to balance on his toes, Bobby made it so he could see not one bit of
his face, which made him appear to be a woman with a flat chest.
Needing a remedy for that, Bobby went into Rachel's sock drawer and
grabbed a few pairs. He stuffed them into his bra and arranged them so
that they looked somewhat like real breasts. Satisfied, he decided to
make his way downstairs.
The trip to the main floor was not easy, and Bobby almost fell several
times. Taking each step painfully slowly, he had one hand on the
railing and one hand on the opposite wall, so that he could balance
himself entirely. When he got to the bottom, he almost fell again, and
only his arms swinging wildly through the air enabled him to stay
upright. Placing his hand on the wall once more, he made his way back
to the couch.
Before he had made it five steps, however, he heard a sound that made
his heart stop. His stomach felt like it had dropped out and he was
filled with an unstoppable panic. He heard the sound of the door
opening.
No matter who it was, there was no way he could explain his way out of
this. There was also no way he could run for cover quickly enough, not
with these heels on. Eyes wide in horror, Bobby could only watch as the
door opened and Rachel stepped into the house.
At first, she didn't see him. "Hey!" she called to the entire house. "I
forgot my cell phone, I?"
Rachel stopped talking as she looked up and into the house. Her eyes
went wide when she saw Bobby, dressed in her clothes and with fake
breasts in his chest. Bobby actually felt his lip tremble as he waited
for the inevitable explosion.
Apparently, his mother was too shocked for something so obvious. She
could only continue to stare, her mouth agape. Bobby figured it
couldn't hurt to say something that would make her feel better.
"Mom, I can explain," he began hurriedly.
Rachel shook her head, grabbed her cell phone, and walked back to the
door. Was she leaving? Would she come back? A million questions ran
through Bobby's brain as he watched her go.
"Mom, wait!" he said. "Don't leave, please, just stay, and I'll explain
everything."
Rachel turned to face her son; she wore a sad expression. "I've got to
go now," she said. "My friend is waiting."
With that, she stepped out of the house and closed the door behind her.
Bobby stood there, heard the sound of a car door slam, and listened as
she drove away again, possibly forever.
CHAPTER TWO
Five minutes later, Bobby was still standing there. He had begun to
shake and he could feel tears running down his face. He had messed up
big time. Suddenly, he didn't want to be in these clothes any longer.
The very thought that wearing them might cause his mother to abandon
him was too much for him to handle, and so he undressed right there in
the kitchen, not bothering to go upstairs and return them to their
rightful places.
He trudged naked to his bedroom, which was on the first floor. Going
into his own dresser, he grabbed a pair of sweatpants and a t-shirt,
not even putting on his boxers. He just wanted to crawl into a hole and
die. He was so embarrassed by the situation and worried about what
Rachel would saw when she came back.
If she came back.
No, he told himself, she would come back. She had to; he was her son,
and she would come back.
He lay on his bed, not moving, not looking at the clock; only once did
he get up, to use the bathroom, and when he was done he lay back down
in the same position. Finally, long after the sun had set and darkness
had descended upon him, Bobby heard the front door opening once more.
His hope rose when he heard the clack of stilettos on the hardwood
floors.
His mother had come back from her dinner with her university friend,
and though this elated Bobby, he still didn't move. If she wanted to
talk, she would come to him. He had decided that a while ago.
For a minute, nothing happened. Then he heard Rachel approaching his
bedroom. He didn't turn to face her. He couldn't face her.
"I need to ask you a question," Rachel said to the back of his head,
"and I need to see your face when you answer it."
Figuring that he owed Rachel pretty much anything she wanted at the
moment, Bobby rolled over and propped his head up on his pillow so that
she had a clear view of his face.
Rachel struggled for a minute. Finally, she said, "I need to know why
you were wearing my clothes."
Bobby hadn't expected this question; he'd thought she would ask the
automatic response to any man doing something not entirely manly in
this society (if he was gay), and so this threw him off.
"I dunno," he said. "I guess ... I like wearing them."
"I figured that," Rachel said quickly. "I meant, why do you like to
wear them?"
Bobby really thought about it, wanting to come up with at least a half-
adequate answer. After a minute, he looked into his mother's eyes and
said what he thought represented his entire life.
"When I wear your clothes, I feel different. Not just because of the
clothes, but because of the feeling I get when I wear them. I feel ...
right, like I was supposed to wear them all along. When I wasn't
wearing them, I didn't know that I didn't feel this way, but as soon as
I put them on, it's like my entire life without them has been wrong."
Rachel stared down at her son. "So, this isn't just some sick fetish or
something?"
Bobby shook his head. He couldn't tell whether or not she was
disappointed in him. After a few minutes of unreadable silence, Bobby's
panic began to mount again, and he feared the explosion was finally
coming his way. He was once again caught off guard when Rachel smiled.
"Thank you," she said.
Frowning, Bobby sat up in his bed. "What?" he asked. "You're not mad?"
Rachel flicked on the light and Bobby saw that tears were running down
her face. She looked genuinely relieved, if not happy.
"No, I'm not mad," she said. "Well, I as at first, but while I was at
dinner, I realized that all that mattered was why you were wearing my
clothes. I'm glad you're doing it for the right reason, is all."
Bobby felt so relieved he could barely keep from smiling. A grin spread
across his face as he realized his mother was actually accepting his
cross-dressing. He let his head fall back onto his pillow, his stomach
filling with a buoyant sensation that made him feel like he could
float.
He and Rachel shared one final look as she made to leave his room.
"We can talk about this whenever you want," she said, "but I just want
you to know that I will always support you, no matter what."
Bobby couldn't find anything to say to that, so he just nodded.
It was enough.
*
A few days later, Rachel was sitting on the couch, watching one of her
favorite programs, when Bobby came and joined her. She was sitting with
her back up against the couch and her legs straight out in front, her
feet resting on the coffee table. Bobby sat in a similar fashion.
As they watched television together, neither of them spoke, just
bonding. Rachel quickly noticed that Bobby was repeatedly stealing
glances at the yoga pants she was wearing, and she smiled. He must
really want to have his own pair. Deciding to do something before his
glances moved from cute to annoying, Rachel turned to her son.
"Bobby," she said, "why don't you go and get my other pair from my
dresser. You should know where they are."
Bobby pretended to be confused. "What are you talking about?" he asked.
"Other pair of what?"
Rachel gave him a knowing look that told him not to bother pretending,
and that, as his mother, she would always be able to tell when he was
lying. Bobby sighed and looked longingly at the pants before moving. He
then caught Rachel's eye.
"Are you sure you're okay with this?" he asked.
Rachel loved her son dearly, but sometimes he thought too much of what
other people wanted, afraid to upset anyone with his own goals.
"I wouldn't have suggested it otherwise, would I?" she said, and Bobby
smiled.
He practically leapt up from the couch and Rachel could tell he was
dying to sprint upstairs and into her bedroom, but he walked at a
normal pace up and out of sight. Rachel waited while he retrieved the
pants and said, "And you might as well grab the panties you wore; I'm
never going to wear them again."
Bobby didn't respond. Rachel loved seeing her son happy, and was happy
for him. She liked that he had something to define him now, some ...
well, she didn't know if hobby was the right word. But she had been
worried that Bobby would grow up the same, always quiet and never going
through with his ideas. This showed that he had the potential to get
past that.
When Bobby came down, Rachel saw that the pants fit him somewhat well.
She smiled at him, and Bobby smiled sheepishly back at her. His face
was tinged red with embarrassment.
"You don't have to be embarrassed," Rachel said. "We're both wearing
them."
Bobby seemed to realize this and moved to sit down again. Rachel
couldn't see any lines from his boxers through the skin-tight pants,
and so assumed he had followed her suggestion to wear her panties.
They resumed watching TV. After a few minutes, Bobby said awkwardly,
"Thanks, Mom."
Rachel just smiled and wrapped her arm around him in response. If Bobby
was happy, then she was happy. And then something came to her that
would make her son happier than she could ever remember him being ...
CHAPTER THREE
A week had passed since Bobby had been found out by Rachel, and it had
been one of the best of his life. He hadn't done anything spectacular
or seen anything breath-taking, but had been able to go home after
school, don his mother's extra pair of yoga pants, and not have to
worry about being caught. He felt comfortable, and not just physically.
He was beginning to find himself.
It was a Friday, and Bobby had just gotten home from school; he was in
the basement, playing WiiSports on his Nintendo (while wearing his yoga
pants) and was kicking ass at tennis when he heard Rachel arrive home
from work. As he continued to play, he heard her making her way
downstairs. She came up behind him and watched his last serve. There
was no way his opponent was coming back.
As the match ended, Bobby turned to his mother. "What's up?" he asked,
shutting off the Nintendo.
"I have a surprise for you," Rachel said, smiling gleefully.
When she didn't elaborate, Bobby said, "And what is it?"
Rachel's smile broadened, if that was possible. "I need you to come
with me."
Why was his mother acting so weirdly? "Come with you where?" Bobby
asked suspiciously.
"I can't tell you, but I promise you, you'll be glad you came," was all
Rachel gave for an answer.
Bobby thought about it. He and his mother had grown closer than ever
before during this past week. He had trusted her with his deepest
secret - well, only after she'd caught him in the act - and she had
accepted it as part of who he was. He figured he could trust her again;
after all, she was his mother.
"Okay," he said. "Let me get changed, though."
Rachel looked like she was going to protest, but thought better of it.
She waved her son upstairs. "Hurry, hurry," she said.
Bobby chuckled at his mother's haste and made his way to his room.
Closing the door behind him, he pulled down the yoga pants, revealing a
pair of silk panties over his hair legs. The sight was odd, for sure,
but Bobby felt at home in the panties. He was not yet ready to shave
his legs, not with summer and shorts coming up. Pulling off the
panties, he replaced them with a pair of boxer briefs and donned his
track pants.
Rachel was waiting at the front door for him. "Come on!" she said, and
Bobby laughed again.
"Mom, are you sure you're okay?" he asked, only kidding. He'd never
seen her so excited - not for a long time, anyway.
Rachel locked the door behind them and the two of them entered her car.
Rachel put the keys in the ignition and backed out of the driveway,
much in the same fashion as she'd done a week before. Bobby looked over
at her and saw that her smile remained on her face.
"Where are we going that's got you so excited?" he asked.
"You'll find out," Rachel said, and Bobby gave up.
As the trip grew longer and longer, Bobby's mind began to wander; he
explored several possible destinations, such as a place that would try
to deprogram him, or make him see the "error" of his ways. What if
Rachel had only lied about accepting him? He shook his head, reminding
himself that Rachel was his mother, and he was being paranoid.
Finally, after forty-five minutes, Bobby realized that they were
leaving the city limits and were headed for the neighboring town.
Wondering where they could be going, Bobby's question was answered when
Rachel pulled into a parking lot. There were several stores in this
plaza, but Rachel headed for the one on the very end, a clothing store
called La Belle Femme.
Bobby had heard of this store. They sold women's clothes.
He looked to Rachel in shock. "What are we doing here?" he asked,
trying to keep his voice calm and his panic low.
Rachel smiled a great big smile at him. "Surprise!" she said happily.
Bobby looked at her incredulously. "You brought me to a clothing
store?" he said. "A girls' clothing store?"
The smile dropped from Rachel's face. "What?" she said. "I thought you
would like this."
Bobby sighed. He hadn't meant to come across so angry. "I do," he said.
"It's just too fast."
"At the rate you move, you'll never buy your own clothes," Rachel said,
trying to convince her son.
"That doesn't matter," Bobby said. "I'll do it at my own pace. And
besides, you could have told me we were coming here. At best it would
have prepared me."
Rachel raised an eyebrow in a "You've-got-to-be-kidding-me" look.
"Bobby, I know you," she said. "You would never have agreed to come
here if I'd told you about it, so I had to surprise you." Bobby began
to object, but Rachel pressed on. "I know it seems daunting, but it
really is a good thing for you. And I'll be there every step of the
way, to help you."
Bobby fell silent. This was more than he'd expected at this point in
his life, but he really did want to do it. He wanted it so badly, but
was afraid of taking such a big step. Weighing the options, he sighed.
"Let's get it over with, then," he said, trying to sound resigned
instead of excited beyond belief.
Rachel clapped happily and got out of the car. Bobby followed suit and
made his way across the parking lot. In late June, the humidity was
always high and this did not help Bobby, as he had begun to sweat from
nerves alone. Thankfully, as they entered the store, they were hit by a
welcome blast of cold air. Bobby stopped to let it flow over his body
before continuing into the store, his heart pounding.
A saleswoman approached them as they stood looking about the store.
"Hello," she said with a kind smile. "My name is Brenda. How may I help
you?"
Her voice sounded like one she had put on to please the paying
customers, and Bobby thought it sounded a little too squeaky.
Rachel looked at Bobby, who nodded. "My son here is looking for a new
wardrobe," she said.
Bobby looked at the floor, waiting for the inevitable realization of
what Rachel meant and the disgust that would follow. Instead, Brenda
said, "Uh, this is a woman's clothing store. It's in the name."
Rachel smiled again. "Yes, we saw that," she said, "but my son is going
through some changes and requires a new wardrobe to facilitate them."
Brenda continued to smile at them for a moment longer. Then her eyes
widened and she seemed to understand what Rachel meant. Her mouth fell
open slightly and her eyes darted rapidly to Bobby.
"Oh, I get it," she said, and Bobby was glad that her squeaky voice was
gone. "Hey, no problem, I'll help you find whatever you need."
Brenda spent the next fifteen minutes taking Bobby around the store,
showing him all of their products. Nobody else entered the store, for
which Bobby was grateful. At the end of the fifteen minutes, he had
accumulated quite a pile of shirts, shorts, skirts, pants, sweaters,
jackets, panties, bras, and even a few pairs of shoes and boots. All
were in the upper sizes that the store offered, because Bobby wasn't
exactly a petit person.
Brenda led them to the back of the store, where there was a line of
changing stalls. Bobby tried on everything except for the underwear and
found that most of it fit well. He looked in the mirror happily, noting
that even the clothes by themselves made him look - and feel - more
feminine. He didn't know if he'd actually slimmed out in the last week
or if it was a mental thing, but he suspected it was the latter. He had
even shaved this morning, and so his face was smoother than a baby.
As he made to take off the clothes, Bobby was struck by a sudden
realization. He wanted to wear the clothes out of the store. He didn't
want to have to take them off ever again. The only problem was, he
didn't think he could make it to the car without being recognized as a
guy. Thinking quickly, he called for Rachel.
"Mom!" he said, trying not to be too loud in case anyone had entered
the store. "Mom, are you there?"
A few seconds later, "Yes, I'm here," came Rachel's voice. "What's the
matter?"
Not hesitating, Bobby said, "I wanna wear the clothes out of the store,
but I don't want anyone seeing me wearing them."
He heard a soft "Oh" of understanding from Rachel; it was followed by a
few moments of silence. After a minute or two, Rachel said, "Hang on,
I'll be right back."
Having no choice but to wait, Bobby stood in the stall, looking his
reflection up and down. These clothes were really nice, he decided.
A moment later, Rachel returned. "I've got Brenda here, and she says
she'll do some make-up for you. Is that okay?"
The idea of wearing make-up made Bobby's heart thump, partly from
anxiety and partly from excitement. "Sure," he said, trying again to
sound nonchalant.
Brenda entered the stall, clutching a small black bag with her. She sat
Bobby down on the small wooden bench in the middle of the stall and
stood in front of him.
"Try not to move," she said.
For the next few minutes, Bobby sat stock still. Brenda applied all
sorts of make-up he didn't even have names for, and she even styled his
hair. She sprayed mousse or something on his hair and combed it over to
one side to make it look more feminine. To complete the picture, she
added a clip to it.
"The clip's free of charge," she said, and smiled at Bobby. Finished,
she placed her items in her bag again and spun Bobby around so he could
see his reflection. "What do you think?"
Bobby was shocked. He was definitely not the most beautiful girl to
pass through this store - though he hadn't expected to be - but he was
extremely passable. He guessed Brenda had applied some sort of blush to
his face, because his cheeks were somewhat pink. His eyes looked like
they had been done up, too, and his eyelashes even seemed longer.
"Thank you," was all he could say.
"One more thing," Brenda said, and Bobby looked at her in the mirror.
She held out a tube of lipstick. "Don't worry, it's not used."
"Uh, can you??" Bobby said. "I mean, I don't know how to?"
Brenda caught the gist of what he was saying and smiled. She spread the
lipstick along Bobby's lips and told him how to make sure it didn't
smudge. Bobby looked at his reflection again, the picture complete.
The two of them headed out of the stall, carrying Bobby's clothes. He
was wearing a pair of black ballet flats, easy to walk in, yet still
feminine. He and Rachel headed to the cash register, where they paid
for his entire wardrobe. Five minutes later, they had thanked Brenda
profusely and were back in the car, headed home, the back seat laden
with bags.
CHAPTER FOUR
The trip back was uneventful. Rachel hummed to herself the entire time,
and Bobby was too happy to talk. When they turned on to their street,
however, he immediately began looking about, making sure no one would
see him. He was relieved to see that nobody was outside. Perhaps it was
too warm for their tastes.
As they pulled into the driveway, Bobby grabbed his bags out of the
backseat. Rachel locked the car after they'd gotten out, and they made
their way up to the door. Halfway up the steps to the front porch,
Bobby stopped.
"Hey, Mom?" he said. Rachel turned to look. "Thanks."
Rachel just smiled at her son. Words were not needed.
As Rachel turned to open the door, the most humiliating thing Bobby
could think of happened. The front door of the house next-door to
theirs creaked open and slammed shut. He looked to Rachel to hurry up
with the door, but the key was stuck. There was nowhere to hide.
Out walked Samantha Allston, the beautiful girl of Bobby's street and
high school. Every guy had either been with her or wanted to be with
her, and Bobby was in the latter half. His chances were quickly brought
down to zero as Samantha raised her eyes and saw him, fully attired in
female clothes and make-up.
"Bobby?" she said, stunned. "Is that you?"
Before Bobby could say anything, Samantha began giggling. Embarrassed,
Bobby ran to the front door, which Rachel had only just unlocked. He
leapt inside, closing it behind him. When Rachel came in after him, he
could still hear Samantha giggling.
"Are you okay?" Rachel asked a moment later.
"No, I'm not okay!" Bobby shouted, not able to face his mother. "I
can't believe I let you talk me into this."
Rachel didn't say anything. She just moved forward and placed a hand on
Bobby's shoulder.
"Don't," he said, shrugging it off. "Please don't bother me for the
rest of the day."
With that, he dropped his bags and headed to his room.
*
Two days later, Bobby was back in his male clothes. Upon arriving home
from the store, he had taken a long shower and washed away any traces
of the make-up that had made him feel so happy. Ever since then, he
hadn't worn any of his new clothes. He didn't ever want to be a girl
again. It was too embarrassing.
On the third day after the Samantha Incident, as it would forever be
known in Bobby's memory, he was approached by Rachel, who had
mercifully left him alone as requested.
"Bobby," she said quietly, as though trying not to upset him, "there's
someone here I want you to meet."
Bobby looked at his mother, confused. "Who is it?" he asked.
"Just come out and say hello," was all he got from Rachel before she
left the room.
Curious, Bobby hesitated only a moment before getting up off his bed
and heading out of his room. Sitting on the living room couch was a
redheaded woman who looked to be the same age as Rachel (late
thirties). She was slim and quite attractive, and wore stylish glasses
over her emerald eyes. She smiled warmly and stood up as Bobby entered
the room.
"Hello, Bobby," she said. "My name is Ellen."
She extended a hand and Bobby unsteadily shook it, not sure what to
make of her. He looked to his mother.
"Who is she?" he asked.
Rachel just looked to Ellen, who nodded understandingly.
"I am here to help you," Ellen said. "I run a very special school for
young people like you. I have helped many a troubled teenager overcome
fears and anxieties in order to become who they are meant to be. I want
to help you as well."
"What are you talking about?" Bobby asked.
"When your mother told me about your ... situation" - Bobby stole a
glance at Rachel, who looked apologetic - "I felt inclined to make
things better for you. I offer you a place at my school."
Bobby was hesitant. He didn't even know this woman. "What kind of
school is it? When would I attend? Who else would be there?"
"It's a school designed for people in your ... situation," Ellen said,
not missing a beat. Bobby took her to mean cross-dressers or
transgendered people. "My program begins the first week of July, so
just after you are finished your regular schooling. As for who will be
there: why, it will be, like I said, people like you, people who are
lost and need help staying on the right path." She paused to let the
message sink in. "What do you say?" she finally asked.
Bobby was silent. He had just met this woman, but she'd made a good
sales pitch. He was glad, too, for a chance to get away from this place
and Samantha and anyone else she might have told by now. Feeling the
right choice was pretty obvious, Bobby nodded.
"I'll go," he said.
Ellen smiled triumphantly and Rachel let out a sigh, probably of
relief.
"That's wonderful, Bobby," Ellen said, looking from Bobby to Rachel and
back. "I will be seeing you in a couple of weeks' time; until then,
good luck."
Bobby nodded. Ellen turned and was led by Rachel to the front door.
With a final nod to Bobby, she stepped out the door and was gone.
Rachel closed and locked the door behind her. She turned back to face
her son.
A new step had been reached in Bobby's long journey to happiness, and
both mother and son knew it.
As Rachel headed to her bedroom, Bobby called after her. "What's this
school of hers called?" he asked. He had every intention of looking it
up online.
Rachel paused. "I don't know," she said, shrugging. "She only called
it, 'The School with No Name'."
CHAPTER FIVE
The roiling clouds in the grey sky overhead oddly represented Bobby's
thoughts as he and his mother made their way to where they had been
instructed to meet the driver who would take Bobby to the institute
known only as "the School with No Name". It had been two weeks since
they'd met with Ellen, the mysterious woman who apparently ran the
School with No Name, and it had been the longest fortnight of Bobby's
short life. What with his growing anxiety about attending the school,
and Samantha and her friends tearing him apart at his high school, he
was glad that the day had finally come.
About a week after his little chat with Ellen, Bobby had received an
interesting tidbit in the mail. It had been a booklet of sorts with
instructions pertaining to his arrival at the School with no Name. Most
of the instructions had been self-explanatory, and all of them had been
or would be followed:
1. You will wear only male clothes upon arrival to the School
2. No one will be allowed to make the trip with you except your driver
3. You will not bring any sort of mp3 player or phone with you
4. You will follow the instructions of the driver without question
5. You will, before meeting with the driver, have completely shaved
your body
6. You will not bring clothes other than the ones who wear to meet the
driver
Rachel had helped Bobby with this last one; even though he knew how to
shave, he'd had trouble with cutting himself accidentally, and he had
several fresh cuts all over his body even at this moment.
As for the driver's instructions, Bobby couldn't imagine what sort of
instructions he'd need to follow that would be all too serious. Also,
the bit about not having an mp3 player was a bit of a downer, as he'd
hoped to listen to some music on the way to the School. It seemed he
would have to find other ways of passing the time.
The drive to the rendezvous point was awkward, and neither Bobby nor
Rachel spoke. Bobby kept his eyes dead ahead on the road, but he could
see out of the corner of his eye that his mother was stealing furtive
glances at him every few minutes or so. After about a half-hour, he
turned to look at her.
"Is there something on my face?" he said, in a moodier voice than he'd
intended.
His mother acted the innocent. "What are you talking about?" she said.
"You've been looking at me funnily ever since we got into the car,"
Bobby said. "What's going on?"
Rachel was silent a moment, and then sighed. "Well, I guess, I was just
worried that you'd change your mind before today," she said. "I keep
thinking you're going to back out."
Bobby thought about this. After a few minutes, "Do you think I should?"
he asked.
"What, back out?" Rachel asked, surprised. "Oh, no, I think you should
go through with it, for as long as you can. This place will help you."
"So this Ellen person says," Bobby countered, scowling. "She didn't
even say what goes on at this School of hers."
Rachel smiled comfortingly. "Don't worry. If you don't like it, you can
always come home."
That was the only thing keeping Bobby sane at this moment.
As the length of their drive increased, the butterflies in Bobby's
stomach seemed to multiply. He hated not knowing what lie ahead for
him, even if it was supposed to be something good. He had tried several
times to look up this School on the internet, with no success. It
really did have no name, apparently. Such obscurity and anonymity made
Bobby think that the School might not be entirely legitimate.
After a few minutes more of driving, they finally reached the parking
lot of the old, closed down Taco Bell. Rachel pulled the car into the
lot, and there was only one other car there: a black work van, with
tinted windows in the front and none in the back. It wasn't exactly the
best thing for Bobby's nerves.
Rachel turned off the car and she and Bobby stepped out onto the
pavement. Bobby was wearing a black track suit with an old pair of
running shoes. He couldn't help but gulp as the driver door of the
black van opened and out stepped a very tall, very beautiful, very
strong-looking woman.
"Bobby Kingsley?" she asked.
Bobby nodded.
"I'm your driver for the day," the woman said, smiling not unkindly.
She reached out a hand and Bobby shook it. "If you'll please get in the
van, we have a schedule to keep."
Bobby looked at his mother, who apparently felt just as bad about this
black van as he did. She caught his eye and tried to give him a
reassuring smile, but the result was that she looked sick. Bobby walked
over to her and the two embraced, hugging.
"See you in two months," Rachel said.
"No, you won't," Bobby said wisely, and Rachel knew what he meant.
The woman watched while they said their goodbyes, and stared after
Rachel as she walked back to her car and drove away. She then turned to
Bobby.
"Please, get in the van now," she said.
Bobby made to go for the passenger door, but the woman stopped him.
"You go in through this door," she said, and opened the back door.
There was a curtain inside the door, so Bobby couldn't see inside. When
he stepped through, his heart beating quickly, he was shocked to see
some sort of restraints attached to the walls, floor, and ceiling.
Before he could get out of the van, however, the woman stepped in
behind him, closing the door.
"What is this?" Bobby asked, horrified.
"Don't worry," the woman said. "It's standard procedure: some of our
past inductees have had second thoughts on the way to the School, and
several accidents forced us to come up with such strict protocol."
"You want me to let you tie me up in those?" Bobby said. "You're crazy.
I'm not gonna let you tie me up."
"Well, then, you're not going to get to go to the School," the woman
said, giving Bobby a stare that said she was all business. "I really
don't care, I get paid either way; I'll just leave you here, and you
can figure out how to get home with no phone and no money."
Bobby didn't want that; he also really wanted to go to the School,
despite whatever misgivings he might have had. Seeing that he had no
other choice, Bobby sighed.
"Fine," he said.
The woman smiled curtly at him and moved around him so she was nearer
the front end of the van. Going into a box behind the driver's seat,
she pulled out two pairs of leather handcuffs.
"Take off your clothes," she said to Bobby, who just gave her an
incredulous look. When he didn't move, she went on, "Take them off or
get out."
This woman was serious, Bobby realized, and so he quickly took of his
windbreaker jacket and track pants, until he was wearing only his boxer
briefs. His hairless body felt somewhat odd; his skin was so smooth.
The woman spun him around and grabbed his wrists, locking them
together. She then did the same for his ankles. Next, she laid him down
on his front and chained the two sets of cuffs together. Pulling him
back up, she forced Bobby into a kneeling position. The chain
connecting the cuffs was tightened until Bobby's hands and feet were
almost touching. His back was at an odd angle now, and he feared he
would have to spend the entire ride like this.
He needn't have feared, though, as the woman next produced a thick
black leather collar with several rings attached around the outside.
She placed it on his neck and tightened it comfortably. A chain was
attached to the ring on the back of the collar, connecting to his
wrists and ankles. Two more chains were attached to either side of the
collar, and were connected to the two walls of the van. Yet another was
attached to the front ring, and hung loosely for the moment.
The woman then produced something Bobby had not seen before from the
box. It looked like a red rubber ball attached to two straps that could
be tightened. He couldn't imagine what it was for, until the woman
explained it.
"This is a ball gag," she said. "Open wide."
Bobby didn't open his mouth. "How is that going to help prevent
accidents?" he said, trying to keep his mouth as tight as possible.
"It's part of the rules," the woman said, "as were your instructions to
follow my orders without question."
"Why?" Bobby asked.
"Without questions means without questions," the woman said, and Bobby
rolled his eyes.
After a moment's hesitation, he opened his mouth wide. The woman
roughly shoved the rubber ball in between his teeth, forcing his mouth
open wide. She tightened the straps behind his head until they were
almost cutting into the sides of his mouth. Drool began to run down
Bobby's chin.
The woman then took the loose chain and attached it to a hook on the
ceiling. She tightened it until it was holding Bobby up on his knees,
and proceeded to tighten the chains holding him to either side of the
van. Was he supposed to spend the entire trip like this? His knees
would be killing him afterward!
Bobby grunted in the woman's direction, not able to say anything past
his gag. The woman smirked at him as she pulled a large hood made of
rubber from the box. She pulled it down over Bobby's head. For a
second, he couldn't breathe, until she aligned the nose holes properly.
There was no mouth hole, so the gag was stuck in Bobby's mouth, and his
drool began to collect inside the mask. There were also no eyeholes; he
was effectively blinded.
"By the way," the woman said, "my name's Violet."
With that, Bobby heard her climb into the front of the van and the
driver's seat. Keys jingled as she started the engine and began to
drive away from the parking lot. The van shook as they went over the
curb and on to the road, but Bobby barely moved, the chains keeping him
in place.
He had a feeling that going home would be much harder than he'd
thought.
CHAPTER SIX
Bobby didn't know how long the ride to the School was, as he was
blindfolded the entire time. He was also gagged, chained, naked down to
his boxers, and covered in drool. He couldn't help but feel he had been
tricked somehow, and that he was not going to a School to help
transgendered people, but a very sick and twisted place where there was
no hope of escaping.
He didn't know how right he was.
During the trip, his mind wandered to every possible idea or thought.
He thought about the bondage he'd been forced to endure and how it
could possibly fit in with his love of tight-fitting clothes. He
thought about who he might meet at the School, and whether or not they
would be cool people. He thought about the woman driving him to the
School, and he thought that she was somewhat pretty, even though she
had tied him up. He even thought about how random thoughts are when you
have spare time.
Finally, after an immeasurable amount of time, Bobby felt the van come
to a stop. The tires screeched and he felt the slightest pressure on
his chains as he was tilted forward a minute amount. The chains did
their job, however, and kept him upright. He heard Violet exit the van,
could faintly make out the crunching of gravel beneath shoes, and was
glad when the back doors of the van opened.
Violet climbed into the van and took off Bobby's hood. He felt the
drool sliding up his face as the mask rubbed against his skin, and he
grimaced - well, he tried to grimace but failed, as he was still
gagged. He shot a dirty look at Violet, who only smiled grimly.
Looking behind Violet, all Bobby could make out were trees, tall pine
trees that seemed to stretch up forever and spread in every direction.
A small path wound their way through the trees, and Bobby guessed that
it led to the School.
"Okay, here's what I'm going to need you to do," Violet said, looking
Bobby right in the eye. "I'm going to take these cuffs and chains off,
and you're going to have to give me your word that you won't try
anything stupid."
Bobby looked at her for a second and then grunted into his gag, as if
to say, "How can I give you my word if I'm still gagged?"
Violet seemed to catch his meaning, so she removed the ball gag. "Do I
have your word?" she asked.
Bobby was silent a moment and then nodded. "Yes," he said, "though I do
have one question."
"Fire away," Violet said, surprising Bobby. Earlier, she'd hated that
he had questions.
"Why are you treating me like I'm a prisoner?" Bobby asked. "I came
here voluntarily."
Violet looked him in the eye. "I'm given a specific set of instructions
to follow when I pick up someone. You may have come here voluntarily,
but others won't have, and I need to follow procedure because I don't
know which group you fall into."
Bobby frowned, confused. "You mean there are people here against their
will?" he asked. "Like, held captive?"
Violet smiled. "You might say that," she said, "but I suggest you
don't. It might upset somebody."
Bobby could only stare as she moved behind him to undo his cuffs. He
swung his arms forward, in front of him, and flexed them to get rid of
some of the stiffness. He quickly made to take off the thick collar,
but Violet grabbed his hand before he could.
"That stays on," she said. To Bobby's questioning look, she added,
"It's part of your uniform here at the School."
"We have to wear a uniform?" Bobby asked. This was getting weirder and
weirder.
Violet, done with the chains, grabbed the ring on the front of Bobby's
collar and led him out of the van.
"Hey, what about my clothes?" he asked, not wanting to be outside
naked.
"Don't worry, you'll get new clothes," Violet said.
Standing him in front of the van's back doors, Violet once more cuffed
his wrists and his ankles and attached them with a loose chain that was
more to keep him from using his hands than to keep him from moving. She
also attached a leash - not a chain, but an actual dog leash - to the
ring on his collar. Smiling at him, she held the ball gag up to his
mouth.
"Oh, come on," he said, rolling his eyes. "Is that really necessa??"
Violet shoved the gag into his mouth, cutting off his question. She
tightened the straps before he could resist and he could feel drool
already beginning to slip out of his mouth. Closing the doors of the
van, Violet tugged slightly on the leash and began to lead Bobby down
the winding path through the forest.
They walked for quite a while, and Bobby was sweating by the time they
reached their destination. At this point, he'd been expecting a log
cabin with a wood-burning stove and a chimney. He was therefore
surprised to see a chain-link fence with barbed wire atop it blocking
their way. Beyond the fence was a large compound, the center of which
was a large slate grey building that was two levels high, and extended
back very far, from what Bobby could see.
Violet led him up to the chain-link fence and found a gate. Taking out
a key ring, she slipped the correct key into the padlock that was
keeping the gate shut. Opening the gate, she led Bobby through and
closed it behind them. Almost instantly, two more women ran up on the
other side of the fence and placed a new lock on the gate. Violet took
the lock she had and placed it in the buckle of Bobby's collar,
effectively trapping him.
With a sardonic smile, Violet led Bobby father into the compound. They
were approaching the building now, and Bobby could see that there were
spotlights fixed to the top of the wall every ten feet or so. There was
no way anyone was escaping this place.
Entering the building, Bobby saw that they were in some sort of atrium,
with a raised ceiling and hallways that led off to other areas. To the
left was a door that said, "Principal's Office". Bobby assumed that was
where Ellen was. Standing just to the left of the door was what caught
his eye, however: a boy was tied to the wall, bound in a similar
fashion to Bobby. He was wearing an odd outfit: a straitjacket kept his
arms to his chest, while a pair of shiny red hot pants showed off his
male bulge. Bobby stopped walking to get Violet's attention. He was
also wearing a similar hood to the one Bobby had worn on the trip here.
She turned around and he motioned with his head to the boy tied to the
wall.
"Oh, like I said, some people don't want to come here," Violet said.
"That boy's one of them. He was enrolled by a family member who decided
they'd had enough of him. An aunt, I think."
Shrugging it off, Violet resumed walking, pulling Bobby along with her.
Bobby continued to stare at the poor boy, who had started upon hearing
Violet's voice. Violet led him to the opposite side of the atrium and
up a large flight of stairs that led to the second floor.
Up here, the layout was different. There was no atrium, and the entire
floor was dedicated to housing for the students present at the School.
Violet led Bobby down a hallway on the far side of where they had come
up from the stairs. At the very end of the hall was a door that read:
"Kingsley". Violet opened the door, which was unlocked, and showed
Bobby to his room.
"This is where you'll be staying during your time here," she said,
walking Bobby over to stand beside the single bed.
The first thing Bobby noticed about the room was that it was awfully
pink. Everything, including the walls, ceiling, furniture, stationary,
and carpets was different shades of pink. It made Bobby feel somewhat
queasy. As he stood taking in the room, Violet undid his cuffs, both of
them, and took out the ball gag. As with before, the collar stayed
locked on his neck; he didn't even bother to protest.
Standing there in his boxers, Bobby suddenly became very self-
conscious; since his hands were now free, he proceeded to try and cover
up as much of himself as he could manage, but was unsuccessful. Violet
gave him an odd look and made to leave the room.
"What do I do now?" Bobby said, not wanting to be alone in this place.
"Someone will be along to get you shortly," Violet said, giving him one
last look. As she walked out the door, she said, "I hope you enjoy your
stay here."
Bobby stared at the door after she'd left. Yeah, right.
CHAPTER SEVEN
Bobby looked around the room, deciding what to do next. He figured the
best thing to do would be to get dressed so that whenever someone came
to fetch him, he would be ready for them.
The room had a pretty cool layout actually: to the right of the door
was a small, one-person bed. Opposite that was a dresser with a vanity
station on top. At the far end of the dresser was a closet that Bobby
assumed was filled with his clothes, and at the back of the room was a
raised section that had a table and chairs, along with some pens and
paper. A lone window let in sunlight from beside the table.
Bobby moved over to the dresser and pulled open one of the top drawers.
Inside was an array of black panties - thongs, to be specific. They
weren't regular thongs, though, as when Bobby picked one up to examine
it, he saw that the front section had a flap and the straps could be
adjusted to different lengths. After a moment's thought, he deduced
that the flap was for holding his penis and testicles, while the
drawstrings were to make his crotch appear flat. Excited by the idea of
such revolutionary underwear, Bobby hastened to try them on.
He took of his boxers and slipped into the thong. He carefully
maneuvered his penis and scrotum into the flap and reached around
himself to tighten the drawstrings. Pulling back an adequate amount
actually made it look like he had a flat crotch. A sensation of elation
flooded through him for a moment before he remembered that all was not
well here. This place was very strange.
Trying to keep his mind off things, a now flat-crotched Bobby closed
that drawer and moved to the one beneath it. This one had a collection
of yoga pants of all colors. Bobby's eyes went wide when he saw them,
as his mother's yoga pants had been his favorite item of clothing. He
grabbed the pair on top of the pile - a black pair with a wide pink
stripe at the top - and slipped into them. They were a perfect fit. He
guessed Rachel had given these people his sizes.
The other top drawer revealed many t-shirts, most of which were light-
colored. Bobby picked out one that was light blue and pulled it on over
his head. It was formfitting and showed off his body. Looking down, he
could see some signs of chubbiness that wouldn't go away, no matter how
hard he tried. He sat down on the bed, slightly depressed. Why was it
that whenever he was happy, he reminded himself of something bad?
Going through the second middle drawer somewhat dispiritedly, Bobby saw
an assortment of shorts and short skirts. He closed the drawer and then
sat down so he could get into the bottom drawers. What he saw shocked
him.
The left drawer held a collection of what looked to be sex toys. He saw
several dildos and a shiny, bulbous metal thing that looked like it was
supposed to be shoved somewhere he didn't want to think about. The
drawer on the right held an arrangement of bondage gear. He saw cuffs,
more ball gags, some colorful tape, and things that looked like their
main purpose was to restrict movement. Confused - and a little
intrigued - Bobby shut the drawers and moved over to his closet.
Opening the closet revealed several blouses, some nice pencil skirts,
jackets, and a pair of expensive-looking evening gowns. On the floor of
the closet were eight pairs of shoes, lined up according to their heel
height, from flats to platform shoes. As Bobby made to close the
closet, something caught his eye: a frilly skirt sticking out from in
between two others. He pulled at the hangar and saw a French maid's
uniform.
What the hell? Why on earth would he need to dress in a French maid's
costume? Here, of all places? There was nobody here he was going to try
and seduce and, quite frankly, he didn't think he could pull it off
anyway. Shaking his head in confusion, Bobby placed the uniform back in
the closet and lay down on his bed.
He had experienced so much confusion in so short a time. His head was
beginning to hurt, and he wanted to rest and take a moment to examine
his situation. He didn't get the chance, though, because someone
knocked on his door.
Groaning slightly, Bobby sat up and swung his legs over the edge of his
bed. He stood and walked to the door; expecting to find whoever was
supposed to come and fetch him, he saw instead a young girl about his
age standing in the hall, looking him up and down. It was a second
before Bobby realized that this was actually a guy! He must be one of
the students who'd come here to the School to cross-dress.
"Uh, hey," Bobby said.
"Hello," the boy/girl said in a decidedly feminine voice. Bobby felt
almost embarrassed by his low male tones. "I'm Sarah. Who might you
be?"
"I, uh, I'm Bobby," Bobby said, unsurely.
A disappointed look passed over the boy/girl's face. "Don't you have a
girl name yet?" he asked, his voice reverting to male, albeit in a
stereotypically homosexual manner.
Bobby shrugged. "I hadn't really thought about it yet," he said.
Figuring this was a good chance to make a friend here, Bobby let the
boy in.
Coming into full view, Bobby saw that he was wearing a miniskirt,
pantyhose, a long-sleeved t-shirt, and ballet flats, all in black. His
hair was somewhat long, which had helped confuse Bobby as to his
gender. He had very feminine features and was very slim.
"I'm Simon," the boy said as he and Bobby made their way to the table
at the back of the room. "Simon Brightman."
Bobby gave his name and they shook hands. There was a moment of awkward
silence before either of them spoke.
"So, how was your ride here?" Bobby asked, suspecting he knew the
answer.
"Very kinky," Simon replied, causing Bobby to raise an eyebrow in a
"Say what?" look. "I mean all those chains and that rubber hood and
gag; leather cuffs, too. Definitely something I could get used to."
"You mean, you like that stuff?" Bobby said.
"What's not to like?" Simon said. "Unless, of course, there's a crazy
person involved; then, I don't think I'd like it."
Bobby couldn't help it; he chuckled. This Simon was quite a character.
"So, how about you?" Simon asked. "Were you all chained and cuffed up?"
Bobby nodded, not wanting to relive the experience.
"We could do it some time," Simon said. "You know, together."
Bobby looked at him. Was he offering to tie him up? This guy was
strange.
"No, thanks," Bobby said. "I'd rather not do that again."
Simon looked dejected. After a moment, the talk picked up again and
moved to how they had found out about this place.
"I practically had to beg my Mom to let me come here," Simon said. "She
thought it would be too weird, me becoming a girl, and didn't want to
upset the neighbors or the rest of our family. I told her I didn't care
what they think, so she signed me up."
Bobby listened to Simon speak interestedly. The boy could talk quite a
bit, but he had some interesting stories to tell. They sat there and
talked for a long enough while that the sun was soon going down outside
of Bobby's window.
"What are you hoping to get out of coming here?" Simon asked.
Bobby thought about it for a while. He knew he was here to become a
girl, because he thought he was meant to be a girl, but he didn't know
why. He supposed it would become clear in time, just as his "girl name"
would.
"I'm here for answers," Bobby said. "I want to know who I am, and how I
become the person I want to be."
Simon nodded in agreement. Apparently, he found these good reasons.
A quick rap at the door interrupted their conversation. Bobby sprung up
out of his chair and skipped across the room to answer it. Standing
there was a blonde woman in an official-looking attire: a black pencil
skirt, a black blouse, nylons, and a pair of stiletto heels. She, too,
looked Bobby up and down, as though appraising him.
"Is there something I can help you with?" Bobby asked.
The woman waited a second before answering, seemingly to build the
dramatic tension. "We're ready for you now."
CHAPTER EIGHT
Ten minutes later, Simon and Bobby had followed the blonde woman along
the hallway, down to the first floor, and along one of the halls to the
far side of the building. They entered the room at the end of the hall
and saw that it was an auditorium, with several rows of seats rising up
from a small stage on the far side of the room. The woman directed them
to their seats.
"This is where you will sit whenever you are called in here," she said,
and left.
Simon looked around the auditorium at the other boys gathered there
already. They were off different races, colors, backgrounds, but all of
them were there for the same reason. He guessed that people all over
the world felt the urge to wear women's clothes.
He looked around at what the boys were wearing, and decided that some
had definitely arrived better prepared than others. The majority of the
boys were skinny and fit into their dresses, skirts, shorts, pants, and
the like very well; they looked very cute in their various outfits.
There were a few, like Bobby, that were either awkwardly built or a
little pudgy. Not that there was anything wrong with that.
As they sat there waiting for whatever the School's staff had prepared,
Simon looked over at Bobby, sitting a few seats away. Even though he
was kind of on the bigger side, he was also kind of cute, and his
roaming eyes were a wonderful shade of blue. What Simon liked about him
was that he seemed sort of nervous about something; Simon had noticed
it while they were talking in Bobby's room.
Simon had definitely freaked him out with his offer to play bondage
games; other than that, everything had gone smoothly. It was a pity
that Bobby didn't feel for Simon what Simon felt for him. Otherwise,
they wouldn't be talking in Bobby's room. Simon smiled at that thought.
His musings were interrupted as the lights in the auditorium went out.
Looking to the stage, he saw someone moving about, but he couldn't make
them out. Suddenly, a spotlight appeared onstage; standing in it was
the woman who had done them all the great favor of bringing them here.
*
Bobby had been looking idly about, and his eyes passed over one of the
ceiling lights the instant they went out. Unable to see anything at
all, he blinked several times in an effort to bring his vision back.
Thankfully, a light appeared on the stage, in the midst of which stood
Ellen. She was wearing casual clothes and had a pair of stiletto mules
on her feet. In her hand was a microphone.
"Hello, everybody," she said into the mike, smiling at the boys
arranged neatly before her.
A few people mumbled back a response, to which Ellen shook her head.
"That wasn't very good," she said. "In the future we shall have to work
on that."
She began walking back and forth across the stage, her eyes darting to
the different students. When they landed on Bobby, they lingered for a
second before moving on.
"Now," she said, "I am going to lay down some ground rules for you.
First off, the lovely women that you have seen around campus are to be
treated with utmost respect. The kitchen workers and janitors will be
referred to as ma'am at all times, and your Instructors" - she
gestured, and several women walked out on to the stage, including
Violet and the blonde woman - "are to be called Mistress."
This confused Bobby. Wasn't a mistress like a lover on the side? That
made no sense.
"Also, I am your headmistress," Ellen went on. "That is how you will
address me."
This sounded somewhat to a threat to Bobby, and he decided then that
Ellen wasn't the nice woman she'd pretended to be when visiting him and
his mother. She had a domineering personality.
"All School rules will be followed or you will be punished," Ellen
continued. "A list of School rules will be handed out to you after this
assembly, and you will take the time to read them. With that list, you
will be given your timetable for while you are here."
The next fifteen minutes were spent listening to Ellen and her ground
rules for living on campus at the School. When she was finished, the
lights turned back on and she walked offstage. Bobby and the other boys
took that as their cue to get up and leave. Sure enough, as they were
exiting the auditorium, several bored-looking ladies stood outside the
doors and handed out pamphlets and timetables. Bobby took his back to
his room. Simon came with him.
They sat down at the table again and began to look at the pamphlet.
Some of these rules were weird.
"What the hell is this?" Bobby asked. "'A butt plug or dildo will be
inside the anus of a student at all times during class'?"
"Hey, it's not as weird as 'The level of restrictiveness of a student's
clothing will depend upon what their Instructors have decided to
allow'."
Growing frustrated by the complex rules and apparent sexual play that
took place here at the School, Bobby put the pamphlet down and checked
his timetable. He looked at it and grew even more confused.
"It says here I'm on maid duty all week," he said. "I thought she said
we have janitors?"
Simon only shrugged. Looking at his own timetable, he said, "I have
etiquette classes all week. Maybe they split us up to keep the classes
small."
"Yeah, but what's maid training?" Bobby asked again. "I don't get any
of this."
He felt his frustration mounting and he took deep breath to calm
himself. "I need to go for a walk," he announced suddenly.
Simon looked up. "Okay," he said. "Do you want company?"
Bobby smiled politely at him. "No, thank you," he said.
Simon pouted, and Bobby turned to walk out the door. He slipped into
the pair of ballet flats he had worn before to the auditorium and
headed out of his room.
Walking down the hall, he passed by dozens of rooms, all of them with
different names printed on the front. There must be a lot of people
here, he realized. There hadn't seemed to be that many in the
auditorium; perhaps there had been more than one assembly. That's how
they'd done things at his high school.
He was ne