Initiation Nightmare (Part 4)

Silvy Richards

Ignoring his sister's call, Paul made his way to his room and while
passing the kitchen saw his mother preparing supper.

"Your sister wants to speak with you... Princess," she smiled as she
said his new name, "So, how was your first day? Was it as bad as you
thought it was going to be?" she asked, as she continued to mash the

"Worse!" he snapped. "I've never been so humiliated in my life!" Paul
stated defeatedly as he took a seat at the kitchen table. "The girls
were so cruel..." he started off by saying but then decided he did not
want to go into details, he finished his phrase with, "... you have no

Already having spent the previous hour chatting away with her daughter
as to what she was making the pledges do this year, Paul's mom finally
noticed the number thirteen written on his forehead. Knowing about it's
significance, she asked with fake sympathy, "I take it a lot of girls
saw your little ding-a-ling and laugh at it's size... is that it?" she
inquired with a smirk, wanting to know more of the nitty-gritty.

"Yes, many people saw it...", he said as he started to blush, "...and
yes, most of them did tease me about my size."

"Aww... poor baby!" his mom just giggled, as she continued doing her
thing getting the food ready, not really feeling any empathy for him.
"What did I tell you about 'sticks and stones' little man?"

"I know mom, but..." Paul paused for a second, "... I don't think I can
go through with it. I think I'm going to quit first thing in the
morning!" he put his foot down, hoping his mom would back up his

"You most definitely not quitting! That is not an option," his mother
let him know immediately where she stood. "I didn't raise quitters, and
that's final! Plus, I just spoke to your father not even two minutes ago
and already told him you were doing fine."

"But mom, you don't get it..." Paul decided to enlighten her as to some
of the days events, "... today after diving practice, we had to shave
our bodies... everywhere. Not only that, but we're going to have to keep
ourselves completely hairless for the next two weeks!" Leaving out the
part about the another boy shaving him and getting an embarrassing boner
in the process, he hope it was enough to make his mother see it his way.

"So you're going to have a hairless body for two weeks... big deal! I
have a hairless body all the time, you don't see me complaining."

"Yeah but, there's more..." not wanting to go there, but feeling he had
no choice, "... Lisa's going to make me wear... p-panties."

Laughing a little after hearing her son hesitate then stutter while
saying the word 'panties', she kept up with the same logic as she said,
"I wear panties everyday. What's so scary about that?"

"Come on mom, guys aren't supposed to wear... girls' underwear!"

"Of course they aren't, unless of course, like you, they're going
through some crazy frat initiation. Listen, a little satin and lace
won't kill you you know? Sure, wearing a thong takes a little getting
used to, but I'm sure you'll do fine," she tried to reason to him.
"Compared to Angie next door, I'd say you're getting off pretty easy.
You realise she's got to have her breasts pretty much on display
everyday! And you?.. you're complaining about the underwear that you'll
be wearing under your clothes?!? Trust me, a little lacy butt-floss is
the least of your worries," she said smugly as she recalled what Lisa
had told her what she was planning on making his wear to school.

"What do you mean the least of my worries?!?" as Paul began to grow

"Well I spoke with Lisa just before you arrived and she sort of put me
up to speed as to what had happened to you, the number on your forehead
and all, and where she was planning on going with this, in terms of your
future wardrobe for the next couple of weeks ," she lightly brought up
the subject with a smirk.

"What am I going to have to wear?" he asked not really wanting to know
the answer, knowing how evil his older sister could be.

"Just so you know, while you were out, I gave her permission to go into
your room and confiscate certain items of clothing. She apparently has
total control as to what you're going to wear for the next two weeks,
and well she boxed up a lot of your stuff, including all your
underwear," as she let the bomb drop, to an unsuspecting Paul.

"What do you mean she was in my room?!? She can't tell me what to wear
when I'm not in school!" he said in total panic, not realising how far
his sister was planning on taking this.

"Well actually, she can. According to the contract you signed at the
frat house, she showed it to me, it clearly states that the nominated
sorority sister that is in charge of a pledge can chose his entire
wardrobe for the entire duration of the hazing, including weekends and
weeknights, if of course she is willing and able to provide it all. Now
your sister has tons of extra clothes, and from what she told me, seems
like you're going to get quite used to wearing a lot of them pretty

Knowing how big Lisa's walk-in-closet was, and how many girly dresses
she had amassed in her lifetime, Paul almost peed himself on the spot.
She had been a bridesmaid at least ten times and a flower girl twice,
and he knew she still kept all those girly dresses as crazy momentos.


Nine hours later, it was almost three in the morning, and Paul has just
finally fallen asleep. Underneath the covers he had on the pink baby
doll with matching frilly panties his sister had sent him to bed
wearing, and was causing him the most bizarre dreams.

After his talk with his mom, Paul went to his room only to discover that
what his mother said was true. His underwear drawer and most of his
closet had been completely raided. All that remained were some of his
old suits that he rarely ever wore, and some winter clothes that were
totally out of season.

Paul really didn't appreciate the predicament he found himself in, five
hours later, as he was walking to school with Angie. Once again her
boobs were being showed off against her will, this time with an
undersized belly shirt that was so short, it exposed the bottom part of
her bare massive tits as they swayed from side to side without any

He on the other hand wasn't as chatty as the previous day due to the
circumstances he was in. His sister that morning had given him an option
for his first dress up day at school. Either a really short pleated
mini-skirt or a pair of his regular boy shorts. The catch was if he
chose his shorts, which of course he ended up doing, he had to agree to
wear an egged shaped butt plug along with them. What Paul hadn't been
told was that the butt plug came with a remote control that it could
make it vibrate at many different speeds at quite a long distance away,
and that Angie, who he shared most of his classes with, had it now in
her hands as they made their way to school.

Despise wearing an embarrassing top that left very little to the
imagination, Angie was quite in a good mood with the power that she had
over Paul, as she started away with her questions pretty much as soon as
the began their walk.

"So tell me... why do you have a that number thirteen on your forehead?"
she asked with a smirk, knowing full well why it was there.

Walking right behind them Lisa and Roxy giggled, as they overheard all
that was being said.

"You know what it means," he said as he blushed trying to walk normal
with butt plug up his ass but was having a hard time. The thong
crotchless panties he was wearing under his shorts weren't helping much

"Enlighten me," she said with an evil grin, as she gave the remote a
little zap.

"It means... my dick isn't very big," he sheepishly admitted, as he grew
redder and had to pause in his tracks for a second due to the zap she
gave him.

"And when I press this button..." to which she gave him another quick
zap, "... does it make it get bigger?" she devilishly asked, as the two
girls in the back went into sprurts of giggles.

"Yes... ohh..." he said as he let out a moan at the same time,  "...
just please stop ok?" he begged, as his penis stiffened.

"Since your cock is so small, does that mean you're wearing diapers? I
heard a rumour that some boys will be wearing diapers to school because
they have baby sized peepees. Are you one of them?" she asked with a
cheshire grin, again knowing full well the answer to the question, but
wanted to hear it from his lips.

"No, I'm not wearing diapers" he admitted, almost desperately wishing he
was. Instead, Paul was wear a tight black tee-shirt that had '3rd
Generation' printed on the front, and pair of his loose gray shorts,
that in normal circumstances required a belt. Under the sagging shorts,
Paul was wear a tiny pair of pink frilly crotchless panties, that had
lace all along the waist bands and a satin triangle in the back.
Covering his middle, thankfully for him, had a sweatshirt wrapped around
his waist, hiding them. His tee-shirt barely made it to his bellybutton,
and his shorts were ridding so low that without the sweatshirt he'd be
redder than he was already.

"So... what are you wearing then?" she pushed him to say it out loud.

"I'm wearing..." he lowered his voice, not wanting to be too loud,

"What was that? I didn't quite hear you," she asked, as she zapped him
again but this time with the number two setting which increased the
speed of the vibrations.

"Panties! Ok?!? I'm wearing panties! Are you happy?!?" he practically
yelled out, as they approached the school entrance. This time, Angie
laughed as loud as Lisa and Roxy who were giggling away, and still
walking steadily behind them.

"YOU"RE WEARING PANTIES!" she almost screamed as they finally made it on
campus, which a number of people turn their heads. Two of which happened
to be Christie and Trish. Paul wanted to shrink on the spot when he saw

"Well, well, well... if it isn't number thirteen, tiny Sweeny?" Christie
sang out, which brought a smile to Trish's lips, as Paul and Angie made
their approach.

"His new name's Princess," Trish corrected her, as she pointed to his
name tag.

Out of nowhere, Paul felt his sweatshirt being yanked and felt the cool
air around his sides, as his panties came into view. "You know what?"
his sister asked, as she waved his sweatshirt teasingly at him, "I don't
think you'll be needing this today," as she casually kept on walking,
wrapping it around her own waist.

Whistles from passing girls and nervous laughter from others followed,
as Paul wanted to crawl into a hole somewhere and hide from all this

"Hey Lisa! Mind if we replace his shorts with something a little more
appropriate?" Christie asked, knowing it was best to always ask
permission first.

"Be my guest," she smuggly said, as Lisa kept up with her pace with
Roxy, not even bothering to wait and witness his morning humiliation

After slowly pulling down his shorts, right there in the middle of broad
daylight , a mini short pleated mini-skirt was pulled up his legs and
zipped into place. Again his miniscule thong panties were showing, and
Christie pointed out, "There's not much material in those panties, is
there?" she playfully teased, slightly pulling at the sides.

"No," Paul mumbled, remembering thinking the same thing when he step
into them just this morning. They weighed nothing, and made him feeling
like he was wearing nothing. Especially since they were crotchless.

Thinking she might have noticed something out of the ordinary, Trish
lifted the back of Paul's new mini-skirt, and saw what looked like a
butt plug behind his thong. "Is that what I think it is?" she asked with
bulging eyes.

"Yep," answered Angie, who gave him a zap, and showed the girls the

"Cool! Let me see that," Christie ran over to her, took the remote, and
right away started testing out the speeds, as Paul squirmed on the spot.

In a matter of seconds, the front of his skirt started to rise, and when
he tried to hide it with his hands, the girls secured his arms behind
his back with handcuffs. Unable to stop his boner from flipping the
front of his mini-skirt, Paul stood helpless as more and more girls
started arriving for school and stopped momentarily to enjoy the free

Handing over the key to the handcuffs and the remote back to Angie,
Trish told them both to be right outside the main building after lunch,
the swim team were going to demonstrating free CPR lessons for the
public and they needed 'volunteers'.

Heading off to their first class, Angie playfully teased Paul when she
made him walk in front of her, "You lead the way... or point the way, I
should say," referring to his erection that still hadn't gone away and
that was still tilting his skirt upwards.


"WE'RE GOING TO NEED SOME VOLUNTEERS," could be heard out loud through a
megaphone. Trish and Christie had gathered up quite a crowd when Paul
heard his new name being broadcast loud and clear, "IS THAT 'PRINCESS'
PAUL SWEENY I SEE OVER THERE?" Pointing in his direction, Paul made his
way the the makeshift stage, as the girls snickered as he pass them.
Someone pulled at his thong, which only made him walk faster to his
unforeseen doom.

Once on the stage, he started to panic when he noticed that the dummy
that they were using for the CPR demo was a blonde blow-up sex doll,
instead of the traditional CPR dummy. Right away, he knew he was totally
fucked, and when he felt his vibrator being turned on, Paul also knew
Angie couldn't be too far, and that things soon were only going to get
worse. Turning around, he saw her in the front row smiling an evil grin,
as she waved the remote to him and winked.

All morning long she had tortured him in their classes, and in the
process gave him a real bad case of blue balls.

Minutes later after he preformed mouth to mouth with the blow-up doll,
Trish announced to everyone that a little 'thirty seconds' were called
for, since they had a third generation pledge here on stage at their
disposal. As his butt plug statred to vibrate, girls on both sides of
him grabbed his arms and held him in place as Christie came in front of
him waving a condom. With his skirt lifted and a fresh condom rolled up
on his tiny cock, the blowup doll was positioned in front of him, and
the girls started fucking him with it, right there on stage, in font of
the whole school.

Twenty five seconds later, Paul got a standing ovation when he made a
funny cum face and announced over the megaphone that had been brought
over to amplify his final embarrassing moan, "Oh God... I'm Cumming!"

People were wiping tears from their eyes from laughing so hard, and cell
phones were being put away, as the show came to an end and the students
started to dispurse.

Day two had ended just as bad as the previous day, if not worse, and
Paul ended up making his way back home only to be allowed to changed
into a red and white polka dotted summer dress. Made of cotton and
coming up to his knees, the seemingly weightless dress swished around
with every step he took. As he started to do his homework, he cringed as
he wondered what the next day was going to be like.

**to be continued**


  1. Giggles, does he not notice the changes cumming on??

  2. Princess Paul swore he would quit.
    But his mum would have none of it.
    "You have nothing to fear.
    Just wear girly underwear."
    It was frilly, Also it did not fit.

    But it certainly suited, Lisa, his big sister.
    She laid out duds fit for a Miss, not a mister.
    So, neath his shorts,
    Princess Paul sports
    Crotchless panties and butt plug up his keister.

    By remote control his butt plug would vibrate.
    Angie held the controls as well as Paul's fate.
    When the plug's activated
    Paul's cock got enervated.
    And with a blow-up doll Paul had a first date.

    'Volunteering' for a C.P.R. demonstration,
    Paul experienced the ultimate humiliation.
    With his butt plug vibrating,
    His cock began inseminating
    The doll. His cock got a 'standing' ovation.