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SEX: MALE[]FEMALE[]
TJ Ryder
http://www.sissytrain.com/
Chapter 1 Registration
Jan Sterling knew he was in trouble with the new school,
just not how much. A thoughtful and resourceful white boy
who had been necessarily so because of a series of family
complications, he frowned at himself as he
got ready for his new school registration. When his divorced mom
took a job out of state and he went with her for his senior
year, he had already been the 'man of the house' for the last
2 years. He did her taxes, took care of all the billing
and paperwork and was used to registering himself, but
with the poor economy his mom had to take a low end job
out of state and move into a mixed neighborhood.
That was okay; he got good grades wherever he went, and this
new area, all he had to do was get through his senior year, take
the SAT's and get a scholarship out. He was already legally
an adult in this state so he could leave anyway, but he had
little money and his mom needed him.
Registration day at Martin Luthor King High, a giant inner
city school of thousands of students, of which only 30 percent were
white, the rest mostly black. Big and Black! Like his father
he was slim and smallish, he wore his blonde hair long because
that was the style and he didn't like paying for haircuts,
and as the boys around his age grew bigger, here the blacks were
much bigger. And some were kind of pushy. More than pushy!
One fat black boy on the bus saw his registration and smiled
and shook his head. "Awmann, yo gwine have a time, whiteboy!
They gwine love you!"
Jan looked him in the eye, trying to be friendly and neutral.
"What do you mean?"
'Mann, donchu know? King is a magnet school for super jocks
and badasses, and you smart an poor white kids, course ah'm only talkin
about white boys. Dey lahk de white gals jus fahn, but yo boys gwine
have to pay up big time! Only way a white boy get away with it
here is being big, mean and varsity. Sheeit, ah thought ah had it bad bein
fat!"
"What do you mean?"
"Cmon, boy, wiseup. Yo betta have at least 5 bucks a day
or you won't make it out of the first mens room or stairwell
you go into!"
"Who wants it?"
"Well, you a senior? The gangs! An don be botherin the
principal neither. They rat you out!"
"Maybe I should transfer!"
"Good luck on dat, takes money or a two hour bus ride or
even worse, get sent to one of dose charter schools where it's
all gang members or retards!"
Jan smiled ruefully, "thanks for letting me know the score!"
"No problem man, but lahk ah say, ah cain't talk to you outside
this bus, you know!"
Jan nodded. When he got to the school and even though it was a week
before it actually started and had only a fraction of students,
it was all he was warned about.
Told about a dozen times by thug wannabees what the
rate was, and who to pay and when to pay, plus a lot of physical
and verbal threats and reminders of what happens to squealers and
holdouts. The only time he didn't get threatened was when he was
with a couple of cute white girls who giggled down the hallway
and because he was wearing a purple shirt from Goodwill and his
hair was long he got nothing but smiles.
'Shit,' he thought as he stood in line to register, 'I don't have
25$ a week, number one, and I don't have the temper to put up with this
crap either! I either have to carry a gun and use it once or I
can't do this! What will I tell mom?" She'll feel so guilty about
putting me in this spot!' Standing with the application, and being sent to
fill it out at a table with a dozen others, he just sat there trying
to figure a way out. 'Just one year! That's all I need! Break it down!
I come to school, ace the classes, take the SAT's and I'm gone!
He had already filled in the name and address and previous school and
his pencil point was over the box SEX: MALE [] FEMALE[].
'What if I was a girl? ' He laughed and smiled at the thought, 'yeah right.'
Then a crazy idea came up! Turning to a very nervous looking white
boy filling his registration out he asked him if there was a mandatory
phys ed in the senior year.
"No, that's an elective!"
"For boys and girls both?"
The youth looked at him with a questionable expression.
"Sure, why not?"
"Just wondering!" He was thinking it through. All he had to do
was pass during the school hours. 'That'd be easy. No phys ed
or locker rooms, my real name is Jan, after I ace the SAT's I just
tell the college it was a clerical error that they thought I was
a girl, happens all the time actually. I get here at 8, leave at
3 pm, nobody hassles me or takes money I don't have! ' He looked
up and saw his reflection in a office window, and there were
a couple white girls beside him in the back.
'Shit, I could be prettier than they are. I'm only 5'5, 125 lbs,
no beardline, long hair, nobody knows me! But how?' He realized he
needed to hurry up and think this through!
When his mom wasn't away on a business trip
he'd have to change somewhere else, and change into what? Well,
Goodwill is nearby, looking around he saw a lot of trampy looking
girls in high skirts. All he'd need is a padded bra, a few skirts
and tops, maybe putting his hair back in a ribbon. That's just
details, he decided, the plan is the only alternative that worked.
This whole year is just a ticketpunch and I'm gone with a full
ride scholarship to some southern college. He checked the
FEMALE box, stood up and stood by the slot to put it the form in.
He was Jan Sterling, White Female!
If he didn't need confirmation on his decision he got it as he went
through the thug gauntlet on the way out,
"Catchoo next tahm boy! Don't forget de tollcharge!"
while he got pissed about it, he also smiled, this is the last time
you'll be seeing this white boy!
With less than 12 dollars he found one complete outfit
at Goodwill, one short skirt, wishing the style was longer,
one sleeveless blouse, matching green almost, and one pair]
of girls sneakers that fit. But as he tried them on in the
unisex bathroom, he realized that the skirt was so short
someone might notice his boy's underwear. They don't have
underwear at Goodwill. He groaned, while he did the wash
usually, he could not bring himself to wear his mom's panties!
Back home and his attractive late thirties mother won't be
home for hours yet, he decided to look in her underwear
drawer, just to know what size he should look for. He couldn't
go into a real store and say he's looking for panties for someone
and not know the size, they'd think he was a pervert right away!
While he did the laundry and had folded her panties before
he felt like a sicko opening her drawer. They looked
too big as he took a lavendar pair out. He had put it there
the other night but now held it in front of himself.
He looked at the size, and then, groaning, slipped his pants
and shorts down and slipped them up, blushing but also
excited. 'This is too perverted' but something also triggered
an erection. Sure he had seen his attractive mother naked
a few times, sharing one bathroom and all, but was this normal?
But he was glad he did, he needed a smaller size, his hips
weren't as big. So now he knew, but how to shop?
And where to go from? He also knew that he couldn't be
coming and going from the apartment as a boy one time
and a girl another. While few people knew him now or his
mom either for that matter, they were there for 8 months,
people would notice. Looking down the street, he saw
several stores with bathrooms, plus a subway entrance
and that had a public bathroom. Yeah, but he needed
a bathroom he could enter as a boy and come out a girl
and right, reverse it on the way back from school,
unless, wait, he did it near the school!
He was thinking of having to ride the bus every day, and
thought of maybe getting a bike. Be a twenty minute ride!
It was an option, nahhh, he thought. He'd have to lock
the bike up at school, and that means he had to change
back and forth inside the school, that wouldn't work.
If he stood out front on the corner every day and caught
the school bus, he'd meet the same people, his mom could
look out the window and see him, wondering who the girl
was and where he was! Nope, but wait, why did he have
to wait at that stop, the bus had a dozen stops, some just
a block away. Right! Change on the next block, go
to still another block, get on bus there, and reverse it
on the way back.
"Dress Rehearsal!" he smiled, excited by the idea now.
One bag for his alternate clothes as he put his new
Goodwill purchases, and he walked out on the street with his
secret identity in a bag. He decided based on the looks he
got from the street it was a good idea he changed a block away,
people already were taking notice, or he thought, but in any case
if you live in an area long enough you do notice what's out of
place. The next block was unknown and undiscovered territory
but he saw a few discount stores and went in one, the
women's section had all kinds of underwear and he cursed because
he hadn't even thought of a bra yet, let alone a padded bra
but of course they had them, had all kinds, he was swamped
and overloaded by choices. A middle aged man was among the
few women in the area and noticed and smiled at him. Some
faggot he thought. He got the panties on sale, although they
were bikini, two pairs, green and purple. But he was stumped
at the bras. When they were alone, the man came by, and he noticed
he really was kind of faggy, wearing eye shadow and a ring on
one earlobe.
"I really would not recommend that one!" he said softly as Jan
picked a package up!
"Excuse me!"
"I'm sorry but I just wanted to save you some time and money!"
He turned away and Jan realized he couldn't try on underwear from
a sign on the wall. It was expensive too, all he had left for his
allowance practically.
Seeing the man move away, he stopped him. "Wait, what did you
mean?"
The man smiled as he turned, "Well, for one thing, theyr'e not
your size, or style! And no returns on undergarments!"
Jan blushed, caught already! But he knew a resource when he saw one!
"So, um, what would you select?"
Feeling more in control the older faggot smiled, looked over
his body and then at the shelves, and asked him how busty he wanted
to be and how much money he had! AFter Jan stammered and told him,
he immediately selected a padded bra for teenagers in his size.
"It's going to take practice getting it on and off, dear boy,
believe me!"
Jan did, and thanked him, but after ten minutes of cursing in
the changing room, he was about to give up when he heard the man's
voice softly again.
"Try this, hook it up first, and then slip it over your head!"
Jan gasped, already sweating in the small booth, that was easy!
"Thanks!" he whispered.
"Do you have the rest of your outfit with you?"
"Um, yes!"
"Try it on, theyv'e very tv friendly here and I might be able
to offer some advice!"
"Well....!" he hesitated, but why not! He can always never come
back to this store and this was a chance at getting some knowledgeable
opinions, better than screwing up for real!
In the mirror he had to admit he looked pretty hot, but the
sleeveless top showed a part of the bra! His legs were kind
of muscular but there were lots of athletic girls. He decided
to keep his sneakers on, but when he opened the packet and put
on a pair of bikini panties, once again he groaned, getting an
erection! Aw mannnnn! What the hell is going on!' Concentrating
on clipper ships, his main hardon reducing image, he was down
enough to hesitantly emerge, fortunately the section of the store
was deserted except for this curious man who looked at him sardonically.
"Very nice! Especially for a first timer. Much better than my own
but of course I don't have your bone structure and was much older!"
"My bra straps show though!"
"Not too important. Must shave the legs though and use some accessories!"
Looking down he realized his legs had fine blonde hair that he didn't
even think about. "Yeah, I guess, and accessories!"
"Are you going to tie your hair back?"
"Oh yeah, I forgot! I have a pair of girls sneakers too!"
'You don't need them, but definitely ponytail, and do bangs!"
"Bangs!"
"Just draw a line across the front and have some hair on your
forehead, in a line! Is this a full time or part time deception?"
"Oh, I have to change back every day!"
"Ah, well, and take the same route every day too I suppose, well
now, that's different. And for how long if I may ask?"
Jan sighed, frowning, "a whole school year!"
"Yes, I assumed so. I'm afraid looking fem is just the tip of
the iceberg. People remember you by more than just a blouse
or a haircut!"
Jan swallowed, "Can you help me?" He tried to keep the
desperation from his voice. "Um, by the way I'm not gay or
anything!"
The man smiled softly, "I'm not coming on to you, dear boy,
my interests are, elsewhere, and I'm not making assumptions either!
But, well, I really shouldn't be offering advice anyway!" He turned
and Jan watched him move away.
He grabbed up his bag, now with his boy things in it,
and walked out, catching him on the sidewalk as he was walking
to a nearby park. In a store window, the man noticed him and
turned and smiled.
"If you want, we can talk further on that bench over there,
right out in public, because I see your desperation!"
"Thanks!" Jan was relieved, he had been expecting a discreet
invitation to a nearby apartment where he expected to see a naked
old man with a hardon in a dress. The man sighed and sat down
breathing in the air, looking up at some pigeons.
"A lovely day indeed! I'm by the way, Thomas Sidewell, retired!"
'Retired from what,'Jan thought, seeing how he spotted him instantly
in a store window. Jan told him his name.
"Ah yes, real name, yes? Convenient, very! It's very difficult
to find a good feminine for Thomas!"
"Excuse me, sir, but when did you...?"
"Decide to pass, oh, in my forties, after my marriage of
15 years, and I was a ridiculous spectacle let me tell you, but I
was at least myself, or thought I was. Before I offer any advice
may I ask a few questions? What brings you to this,
my boy?"
"A high school run by black thugs! I just have to make it through
June!"
"Ah yes, interesting! Wouldn't it be easier though to just pay
them off?"
"If I had the money! I don't! Besides it would piss me off!"
"Hmmm, pride, a handicap definitely, Live with your parents?
Please tell me if I'm getting personal!"
"Mom's divorced! Look I just want to finish my senior year
and get a scholarship to college!" There was a pause as the old man
pursed his lips without expressing his thoughts.
"I see, this neighborhood isn't for the rich, but how much
would it actually cost to pay these hoodlums off? It's just
business you know. I mean passing as a female is much harder than
it looks and you are already spending money on that!"
Jan paused, considering it. "I, well, I don't have the
temper to take shit like that every day at school. I'd probably
fight back and that would be, well, dangerous!"
"Yes, I believe it would be!" he agreed with a nod. "But
girls, even t-gyrls as I prefer, take shit, take even more shit
in some ways, and the prettier the girl, the more attention she
gets, and, my boy, I would do anything to look like you at your
age!"
Jan smiled, "thanks, you know, I do see pretty girls getting
hit on, and I think it would be justice for these bastards if I'm
the one controlling it!"
"you must be careful there, but yes, there is a subtle power
to becoming a female! It is exciting isn't it?"
"It's like, imagining a superhero, from a different perspective!
But what is it you said about being able to pass, like an iceberg?"
"Oh yes, let me put it this way, from about 20 feet away, without
you moving and sitting in a more neutral pose, legs together,(Jan frowned
and closed his thighs together), you can pass to a complete stranger
who's never seen you before. Your voice is masculine although high
enough range so that if you speak more softly it might work.
Your mannerisms are all masculine, but more important you are talking
from the male point of view. Judgmental, action oriented, decisive,
risk taking, logical. That's the area to focus on!"
'Yeah, right, and how do I do that?"
"Dear boy, you already know, we all do, or you wouldn't be
sitting here wearing a padded bra and panties with an erection!"
Jan opened his mouth in protest and shock and then arranged
himself.
"Um sorry!"
"That's actually quite simple, use a pleated skirt, in fact
learn some sewing and do some basic alterations. You'll want
a ribbed panty front to contain your equipment. But mostly
you want to slip into that other you. Or more accurately,
slip out of the 'outside you' and reveal the 'inside you!'
"And that's, how exactly!"
He smiled, become the other person in your head first, think
of how she feels, how she would react, because that is you!
And by the way, where is your wallet and keys right now?"
"It, well, it's here in my bag!"
"Where would that be in school?"
"In my locker? Oh gosh, I need a purse or something!"
"Purses can be snatched or forgotten, especially for someone
who never carried one. Sew a pocket on the hip of every skirt,
use a thin wallet with just what you need in it!"
"I never thought,..., thanks!"
"What does your driver's license look like?"
"What! oh mannn, I look like a boy and it says Male on it!
I can only show that when I'm a boy, can't I?"
"That and a hundred other things! But it's easier for you,
I had to learn to walk in heels, makeup, some cosmetics,
hair styling, lose so much weight and firm so many parts up!"
"I'm beginning to see what you mean! What would you do?
You see my plan now. If you were me, what would you do?"
"To carry out your plan? Well, first I would have a very
different plan but you are committed to this one, yes? very well!
He looked at him for several minutes!
"Large square horn rimmed glasses. You say scholarship, must
look scholarly, plain clear lens. Go well with your oval face!
You can get plain colored contact lenses at a gift shop! You
have almost black eyes now, make them light green or blue, that
will help immensely but some people have difficulty with contacts.
Where do you plan on changing back and forth?" Jan was taking note
in his mind and told him.
"That's actually pretty good, very good, you don't really have
much choice. Pick a block further away for the first few weeks
so when you make a mistake you can not go back there!"
"Gosh, this is really good, lucky I ran into you! But back to
the other self bit. How do I get into that?"
"You need a trigger, that's what I recommend. Must be sexual
too, because it never goes away and it has a powerful memory!"
"Sexual?" Jan was getting a little worried now about this man,
'here it comes' he was thinking.
"Yes, suppose a big black high school thug was looming over
you with an intimidating expression, that young man by the corner
for example who is checking out your legs!"
Jan looked over and frowned.
"No, no, Look at you, you frown, your chin is jutting out, jaw muscles
are firm, you fists tighten! Now go opposite!"
"What, how...!"
"Disarm him completely, smile softly at him, arch your back a little
and show those padded boobs, cross your legs!"
'I don't know, well, like, (he tried to act a little coy, and smiled
in the big thug's direction! The brute's expression changed, his whole
body language changed, his hand instantly moving to his groin, and he
broke into a big grin. Jan was amazed.
"It's like having super powers, I never did that before!"
"Yes, if he didn't think you were sitting with your father he
would be right here besides you, and then what would you do?"
Jan paused, avoiding the black man's look now, realizing that power
has consequences. "Wow!" Imagining what he would do if that
brute was sitting right there hitting on him.
"I think your'e beginning to understand. Play men carefully.
You will be approached constantly so choose carefully. I would not
be dating for a while were I you!"
"Dating!"
"Yes, it's an excellent cover. Choose the biggest and baddest thug
but with something inside that you think you can deal with.
The problem really is when to disclose your true self
and that's the dangerous part. If he talks you have to change schools!"
"I'm not dating...!"
"Better to use an intermediary, need to find a young stud deep
in the closet! Hmmm, I have a dear friend who's a teacher at King if you
like!"
"You do? But I'm not ready to date, in fact I'm not dating at
all!" Then he realized what he offered. "Wait a minute here, your'e
talking about dating another boy! I get it and I guess that's a big
deal though, your willing to get your friend to help!"
"Welcome to the community dear boy, we don't have much but
we do try to help each other out!"
*********************************************************** **
Chapter 2 Opening Day
At home later with his new sewing kit, he had already poked
himself once as he got the hang of it. A pleat on his skirt,
a little side pocket, not perfect work but nobody would notice.
Using a hair removal product on his legs, letting it settle in
before wiping it off. And his knees were a little rough, skin
softener from mom's medicine chest. Looking at himself in the
mirror, he picked up his mother's reading glasses and imagined
green or blue eyes. The door opened and his mom came in. He
ran around gathering up all his new stuff and only then cursed himself
because he didn't think already of a place to hide it all except
under his bed.
"Hi mom, tough day?"
"Hi, honey," the woman said, sighing as she sat down in the
main room of the small two bedroom unit, shaking off her sandals,
'a long day, not many sales! How did registration go?"
"Oh, fine," he said breezily, sitting down in his shorts across
from her on the couch.
"When do you start?"
"Another week, I, hate to ask this, but I need some money!"
She nodded as her eyes rolled, "I expect that, books and things!"
"Yes,' he said, feeling a little guilty because it was for more than
that, and she worked hard for what she got. One day he would be on top and
support her!
*******************************************
Reading at night, he took out a book he hadn't read for a long time,
and something about what Thomas said made him reach for it. A 19th century
romance written by a woman, about a woman and her first love! There
was something about the character of this young woman that made her so
fascinating. She was firm and direct, but also soft and feminine.
Such a luxury to be like that on the hard streets. A boy would be
beaten up, girls were prized for it! But like in the novel, if she
gave the wrong signal to the wrong person, a lot of complications
that could have been avoided. That's what thoughtful women did who
at the same time attracted men all the time, they sent the right
signals, mostly polite but firm rejections of further interest.
How long would that last, he wondered, days and weeks and months,
until June?
"Jane Austen, he thought, Jay Austen,' he smiled. Yet as he
thought of Jane Austen's heroines, they were always polite
and outwardly non assertive, but in the end prevailed.
He did two dress rehearsals the next week, and even though he
was looking for that old man again he was also kind of glad not to
see him. Made one mistake at a restaurant and avoided that block
for a while.
"Jan, did you already leave for school?" His mom yelled
from the kitchen as he was packing his secret identity bag.
Hmmm, he wondered, as he slipped on his panties, and boys
clothes on top.
"No mom! On my way!"
"Better take a granola bag, I'm gone, see you tonight!"
"Okay, bye!" he yelled. If he never wore boy's underwear
they'd never need washing, and he has to wash out his girls stuff,
plus get at least another dress, but he wanted to see what the
'other' girls wore first.
Dressing in a unisex stall on platform 21, looking around
and finally taking a deep breath and stepping out, upset as usual
by the different looks he always got, especially by males,
but it seemed fine. Nobody gave him more than a second look
and just one whistle on the school bus, which was mostly white.
"Who's the new girl?" one girl asked another, "Don't know!"
Walking up the steps past the grinning and crotch grabbing
bruthas, smiling politely but not making eye contact, he merged
in with two other packs of kids, and took a seat at the back
of the first class, the homeworm. Looking around, most of the
blacks coming late, the white boys especially nervous, wondering
how many would last, he got a grin from a brutha on the right
and some curious looks from two cute white girls.
"Hey babe, aint seen you befo?"
He smiled, "First year at King!" The girls heard that and a
bitchy blonde frowned, "From where, Beverly Hills Goodwill?"
He was surprised by the hostility but gave her a catty smile and
the finger, getting a laugh from the other kids. Some already didn't
like him much and he knew he had to watch himself,
but at the same time, he wasn't taking any
shit either. By the end of the day, just one teacher took a second
look at him, his math teacher, a middle aged stocky woman. Mrs. Alda
Lipschitz, which of course gave rise to the usual imitations.
"Your'e Jan Sterling?"
"Um, Yes ma'am!"
"Somehow I thought you were a male!" he tensed up at that until
she smiled.
"Blondes don't normally have your Math SAT scores!"
He breathed easier, they were buying it! At lunch time he
sat by himself but was invited over to a girls table and recognized
one of them in math class, a slightly overweight brunette. Most of
the girls were white, and what he figured were the outsiders table,
not too cute but not too stupid either.
"Hi Jan, this is Tanisha, Hillary, I'm Heather, and this is Joanie!"
He smiled and tried to remember.
"Never mind what Pammy said, she's a cheerleader bitch you know!"
as if that explained it all.
They all laughed at that.
"Actually she has her period today but had to come on the first
day of school! So she's twice the bitch she normally is!"
He was thinking he didn't know much about that but gave a sympathetic
shrug. Another thing to know about. What if some girl asks if he
had something for it and he had no idea what she was talking about.
"I guess she didn't like my clothes!"
"Forget her, your'e into retro that's all!"
A week later there were no real problems except getting hit on by
some thugs but at least they weren't extorting money he didn't have.
And to his surprise he was pitched for a cheerleading spot which he
smiled and said he had schedule conflicts. The girls seemed truly
disappointed but there was no way he could pull that off. By the third week
he was beginning to realize he couldn't be too standoffish with the bruthas
too long, some were beginning to think he was a dyke so he slipped a suggestion
that he had a boyfriend already, and that of course led to who he was, and
he cursed because that was a temporary story, not something that would
hold up for a year. He figured it bought him a few weeks and then what?
"Dear, how's your new school?" his mom asked at a rare time when they
shared breakfast!
"Good, mom, actually easier than my last school!"
"I know its inner city, is it hard being a white boy?" He didn't want
to say it would have been impossible for a white boy but he said he
was managing okay.
"Oh, and I have some college scholarship mail for you!" She handed him
a thick manila envelope from the college he was mostly interested in.
"Wow, great," as he tore it open. Grades were fine, that's good,
SAT's are already acceptable if he improved just a little which he knew
he would, and then, he saw it. Black space for the name of his
high school advisor, preferable a teacher or administrator for his
personal recommendation.
"Everything okay, honey?"
"Um, sure mom, ah, they want me to name my faculty advisor for my
scholarship application!"
"Oh, well, didn't you say your math teacher likes you?"
"Yeah, right!" All his teachers considered him a girl now. Could
be anyone in administration or faculty though! Someone who would give
him a recommendation and also cover for the male/female misunderstanding
if it came to light. IF he didn't have that this whole plan was just
a waste of time, the whole year was wasted, and this was a one time
chance at a scholarship! This ain't good, he said to himself.
This, plus the bruthas and the girls think I have a mystery boyfriend
and that isn't going to last long either.
************************************************
Chapter 3 Snags and Solutions!
It took a day for him to come with an idea, and it went back to that
old advisor in the dress shop! Awmannnn! Hitting that shop again,
he decided to ask an employee who looked pretty faggy if he knew him
and while the man was really interested in him, he told him he was
usually at the local public library as a part time job.
He was working on a card catalog in the back stacks and looked up
and cocked an eyebrow.
"Well, and how is school going?" he said softly with a trace of smile.
"Ah, well, I have a couple of problems actually. I wonder if we could
talk if you don't mind helping me further!"
He sighed, "this is a volunteer job, just to pass the time. I can
break when I want! Want to step outside?" Jan nodded, and
sitting on a stone bench by a back garden he told him about the needed
advisor.
"I wouldn't have come but you did mention you had a friend at King High!"
"Yes, I do," he said thoughtfully, and Jan wondered again what he would
have to do for the introduction.
"And how else is school going?"
"Well, you were right about my getting hit on. I had to tell them I
have a boyfriend! That isn't going to last long either!" he frowned.
"No, that's the problem with a secret life, keeping the stories
straight! Well, my boy, I can give you an introduction to my friend
Marcus but you realize if he is asked to say you are actually a boy
he would be taking a little risk there!"
"Um, yes, hopefully he wouldn't have to!"
"Well, I'm sure he will be hoping that too, but if he does act
as your scholarship advisor and make a recommendations, and he has
many friends in higher education, you'd have to do your part as well.
Get good grades, high scores, be a credit to his reputation!"
"Oh, well, of course I would!"
'And probably you and he will have to deal with all of that!
I'll call him tonight and fill him in if you like!"
Jan smiled gratefully, "Thanks a lot!"
"But, you'll have to do favors for him too, you know! He's always
looking for volunteer tutors because he does remedial classes as well
as being an advisor for the Senior Class!"
Tutoring didn't sound too bad so he agreed.
*********************************************************** ******
Chapter 4 New Questions!
He found out the next day Marcus Wilson was a Social Science teacher,
a slush course that was an elective and he didn't bother with, 30 years
with the school system and had a doctorate, unusual for a high school
but what really surprised him was he was an advisor on so many clubs.
And the one that caught his eye was the Gay, Lesbian, Bisexual, Trans
club, which had maybe a hundred members. Surprised to see that in a mostly
black high school but it had a few thousand students so he figured it fit
in somehow.
Standing outside his office after school, knowing he would miss the
school bus and have to take a subway transfer ride, he saw the pudgy
balding male with a huge brief case shuffle up the hallway, and he
was disappointed to see he had several kids talking to him as they
followed him along. Marcus caught his eye though, and he felt like
he was recognized immediately.
"Excuse me guys," he said, "I have an appointment. And Tyrone,
no more trouble!"
"No suh!" As they left, Marcus looked at Jan with an amused expression.
'Very nicely done," he smiled, "come into my office, 'Miss' Sterling!'
"Thank you sir," and when he sat on the wooden chair as Marcus
settled behind his paper covered desk, he couldn't even cross his legs.
"All right, I got filled in, and Alan was right, he would kill to
look like you do, but it is already unravelling isn't it?"
Jan sighed, happy to confide in someone at school. He nodded.
"And it's not just the scholarship which I will help you with if
you keep the grades up by the way. If they try to fire me for being
party to a ruse I will threaten to break the story of how a white boy
has to put on a dress to survive in King High school and threaten
to sue everyone and that will bring enough clout in to get you into
many excellent colleges, maybe not the one you want though!"
"I really appreciate what your'e doing, doctor!"
"Oh, forget that doctor bit. I'm a teacher. I'm more concerned
about you, Jan, a teen white boy in a dress making very complicated
plans and big decisions when he should be just enjoying his youth and
exploring his own life and interests!"
"Well, since Mom divorced I have had to pick up a lot of other
things to take care of!"
'Your'e not alone, Jan, many of the boys here practically have no
mothers or fathers and some are trying despite more obstacles than
you can imagine! Did Alan said I need tutors, volunteer because
there's no budget for them?"
"Yes!"
"Hmmmmm, let's do a two for one. You need a pretend boyfriend
correct, from what I hear! Hardly an original problem for me, since
you have no doubt checked and found out what clubs I was advisor to!"
"Yes, um, and of course I don't want be on any of those club
rosters, Doctor, um, Mr. Wilson!"
He frowned, 'no of course not, your'e very ambitious and a little
bit ruthless aren't you, Jan? Qualities! Making them work, hmmm!
Jan I have to ask you personal questions here, to make this work?"
Jan shrugged and he continued.
"I wonder how honest you are with yourself! Alan said you liked
the power of attracting big black males!"
"Well, I mean I get a different treatment than a skinny white
boy here, that's what I like!"
"Yes, and now you say you need a pretend black boyfriend! And you
think a tutoring gig would do it?"
"Well, I mean, um, wouldn't it? I mean its not like it's anything
you know!"
Marcus looked at him for a while, and lit his pipe, taking a long
suck and filling the air with a pine tree fragrance.
"What if, let us say, that we have at this school other boys,
big black boys, who have a similar problem, and maybe you could
help each other out!"
"Wow, you mean there are other boys in drag here?"
"No, I don't think so, but urban black youths, especially athletic
heroes, well, they can't come out gay, not in this school! If I knew
a boy like that who needed tutoring, and also needed someone to call
his girlfriend, then neither of you would represent a threat or revealing
his secret, would you?"
Jan sat there considering this, something he realized he probably
should have considered. "I think I see what you mean, Mr. Williams!"
"It has built in security on many levels! If you chose the right
person, both of you that is, you can help each other get through the
last year of school!"
"That would be nice," Jan admitted!
"But, how to choose!" Marcus opened a file cabinet and took our
a half dozen snapshots of students, all black and all male!
"This," he smiled, "is what the CIA people would call the MLK Knock list!
Do you know any of these boys. None are in any of your classes but you
might have seen them around?"
Jan shook his head, they were all big and some looked kind of brutal.
"You don't go to any sports events do you, no, I didn't think so!"
"I, um, they all need tutoring I suppose!"
'Mostly, although not necessarily in academics, some just need socialization
that doesn't begin with sex and end with violence! Most black boys
especially, aren't thugs, despite what you see! However they have a role
and the only civilizing influence they may ever see in their lives is
that of a 'girlfriend', but unfortunately many of their peer girlfriends
reagard them as 'baby daddies'! Jan was realizing how frank Marcus was
and where this might be going.
"And we have a young white boy, smart and opportunistic, flexible with
his sexual identity or at least his public one. Frankly Jan, you could
do some good here, have you considered that?"
"Your'e suggesting, exactly,... what?"
"Most of my work in these clubs are with sexual orientation and
dysfunctional social behaviorsd, Jan, but I can tell you right now
this course could be very dangerous if your'e not up front with yourselves
and what you want!"
Jan sighed, "It isn't like something I hadn't considered, being,
well, maybe bi or something!"
"I'm sure, everyone does and everyone is, but here, we have to talk
about survival in your case. You should know that if you pretend to
be a girlfriend to one of these boys you should be able to carry it
off. Let's take it in stages. Could you pretend to be affectionate?"
Jan picked up one of the pictures, looking into the eyes of a big
powerful black athlete. "You mean like holding hands or, well, kissing?"
"IF this was a suburban private white school, I would say yes! But here,
I'm talking about everything. Here casual relationships involve
heavy makeouts, handjobs and oral sex!" Jan gasped at that and Marcus
smiled, nodding. "More than casual is unprotected sex, and my main
concern is not morals in a school like this, Jan. Its about pregnancy
and disease and jealousy fueled gunfights. What I said about survival
to bring a middle class whiteboy who looks like a hot girl into this
arena!"
"Oh myyyyyy!"
"Exactly, I have some literature I want you to read, I give it out
to everyone. I am not advocating sex activity, but sexual safety!"
"Yes sir!"
"And here is a disc that is for sexual identity questions, and
don't let anyone know you got it from me!"
"No, I mean yes sir!"
"Come back when you have come to a decision about progressing further!"
That seemed to close it out, and Jan walked out with two cds that he
figured would change his life if he played them. And he had to wait until
Friday night when his mom wasn't home. When he got to the part about
oral sex techniques, he put his pants and panties down around his ankles
and had to force himself not to masturbate until he finished.
The next morning as he slipped his panties over a hardon, vaguely
remembering the disturbing dreams, he frowned at his reflection, half
boy and girl because he hadn't touched up.
'Maybe I am bi and more submissive than I thought, but so what?
It's a game, the only game I can come up with,' he decided 'there's no
choice, no real choice, and what's the harm anyway? I'll do my job!
Then get my scholarship, back into pants and life actually begins!'
*
Chapter 5 First Boyfriend!
MEMBERS, do you want this story completed next or the SEX Dommymommy? Email me and let me know!
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