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Modern Sissy!
TJ Ryder
Chapter 1
Mother's Little Boy!
http://www.sissytrain.com/
Scene! Midterm at Briarcliff Academy, a private school for
correcting bad boys by making them good 'gyrls'!
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Terrence, aka Terry, frowned as he sat on his bunk
looking at the open closet where he now had no male clothes yet.
Just dresses now; and his 4 drawer bureau only had feminine
underwear and some assorted blouses and skirts.
'This is going to be a problem,' he thought, considering
the request he got the other night from his latest girlfriend.
Amanda Pullings and he had hit it off on a double date
a couple of weeks ago, and as one of the 'approved' social
venues on the list at Briarcliff, it meant she was fair game for
going off campus or she could come on campus and pick
him up anytime he was free. That was not something to easily
dismiss at the rigid school for turning bad boys into good 'gyrls'!
As long as his grades were okay and his number of demerits
stayed below average he could see her anytime she wanted to.
The problem was he met her through a blind date with another
boy, Peter(Petra) and his mother Victoria. It was the
second blind date with Peter and his mom, the first not working
out too well. His fascination with Peter's relationship with
his beautiful dominatrix mother had even led him to accept a few
invitations to their large home in Ruxford. Now with this
new woman as his girlfriend, his friendship with Peter and his
mom, he was thinking as he idly stroked his cock inside his
sheer pink panties.
His femme roommate was wearing a tiny
frilly see-through smock and panties also, pretty much their only
clothing while hanging around the dormitory now. Dorian was
laying on his bunk reading a garish forbidden novel, as usual.
He could ask him what to do, and hesitated.
He got a lot of information from Dorian but he hated the subtle
putdowns the older boy/gyrl always managed to slip in, treating
him like a novice idiot. He might have been that a few months
ago when he dressed and acted like any other boy, but the
treatment of feminization and discipline, and
'approved' dominatrix older girlfriends had changed him to the
point where he was more comfortable in women's clothes than
men. He even swished a little when nobody was looking.
"Dorian, say, I have a question!"
(Sigh!) "Go ahead!" He muttered without looking up.
"I have no boys clothes left, they put them all in
storage!"
'Sure, its midterm you know. Even freshmen lose their
male clothes by now!"
"Yes, I know, but what if my girlfriend doesn't like me
dressing like a, well, you know, a girl?"
"She doesn't?" He looked surprised. All the 'girls' they
met at approved dances were screened very carefully by the
administration. Most were older dommes or mothers.
"Well I suppose one might negotiate some sort of indulgence if
you put it that way. Keep one change of clothes for dates
with her! Might be difficult though! By this time of the
program wer'e all in maid training pretty heavy!"
Terry rose from his bunk and went to his closet where two
different versions of maid outfit hung. One was severe black
and white, the other extremely frilly and pink/purple.
"Maybe I could wear the black and white one. It's a
uniform at least!"
"Mmmmm, why doesn't she want you in drag? I thought all the
approved mistresses did!"
"Oh, she likes me in panties all right, but well, she
wants me to call her 'mother'.
"Ah hah, and she's nursing, right? So she's not a domme!"
Terry blushed and nodded.
"Okay, no problem, just wear a raincoat over your
panties when she picks you up!"
"I guess that might work actually, but, that brings up
another problem, the demerits. Iv'e got 25 so far this week!"
"Hmmmm, let's see, not even Saturday yet, so your'e looking
at a good session. The dildo dykes will want to see a nice
striped butt on Monday for sure!" That's what they called
the pair of lesbian proctors who monitored the boys in
their wing of the dormitory.
"I know, but she doesn't do spankings. Doesn't like em for
some reason! I don't know!"
"So, have someone else do it! Would she mind that?"
He paused considering it. "I don't think so, but she
was very clear about me not having another girlfriend!"
"How about a boyfriend?"
"How would I do that? We haven't even had our first dance
yet with boys invited!" Privately he wasn't all
that sure he could even have a boyfriend, let along be spanked
by one!
"Sorry, for once you stumped the old master!"
"Okay, well, thanks anyway!"
He was talking to Peter the next evening in the boy's room
about it. The femme boy wore only a tiny nightie and a dog
collar.
"I don't know, Terry. Mother likes Amanda, and she helped breast
feed her son until he was 9 when his father put him in a boarding
school and made her stop. She really misses breast feeding and
all that stuff! She even breast fed me when mom wasn't
available. I mean theyv'e been helping each other babysit since
I WAS a baby!"
"I don't want to break up with her, but I'll probably have
30 demerits by Saturday!"
"Well, if you weren't so stupid you wouldn't have any!"
"Okay, that isn't fair! Just because you never have any!"
"Okay, sorry!" the boy turned away to put a different cd in
the player and Terry looked at his white buttocks with fading
stripes!
"Actually, that reminds me, you always have a striped butt
on Monday and you never get demerits!"
He smiled over his shoulder. "Youv'e seen my mother and
ask that? And my younger sister is actually worse!"
His gorgeous younger sister Brittanny appeared in his mind
at that moment!
"I only saw Brittanny on Saturday morning for a bit when
I came over to drop those cds off!"
"You should have hung around, they would have spent less
time on me! DIdn't you hear the noise!"
He did hear it, but thought it was a movie. "Who was that
screaming and begging?"
"Oh, mmm, was he older or like our age? Cuz a neighbor
lady friend of mom's sends her son over for discipline and
maid training a lot! I think Eric/Erica was there then!"
"Older I think!"
"Oh, that was just dad!"
"Your father!"
"Every male in my family is maid trained and disciplined
every Saturday night, in my house at least. It's quite common
in Briarcliff alumni!"
"Well, who, well, who was doing the, you know!"
"Brittanny probably, but sometimes we have another dominatrix
school friend of hers or even a friend of mother's pop in to help
out!"
He got hard thinking of the sweet excited flushed face
of Brittanny coming out of another room with an older male voice
sobbing and muffled pleading and feminine laughter, and
Brittanny smiling at him, arching her big breasts out in a
tiny see through peignoir nightie for him to gaze at.
The intense humiliation of such a scene made him flush and
he wondered if he could stand it!
Then he got a message from Amanda and went back to his
own room to return it. All the calls went through the central
telephone station and could be monitored, at least until his
final year.
"Hi, um, Amanda! I just got your note!" He winced as he
realized he didn't call her mother or mommy! There was a
slight pause, but she didn't sound like she noticed.
"Hello dear, would it be convenient if I dropped by
in an hour!"
Getting hard instantly, he arranged his boner in his
panties and sighed. He was thinking her big breasts were tight
with milk.
"Oh yes, 'mother'," he sighed, "that would be nice!"
"Good, and do you remember, about your clothes?"
"Yes mother, Iv'e been working on it, but my wardrobe
is limited!"
"Be a good boy and I'll pick you up in a couple of hours!"
He said goodbye, and then looked at himself in the mirror.
Continued in upcoming story!
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