Initiation Nightmare (Part 5)

Silvy Richards

As the days followed one another, Paul was forced to submit to countless
different forms humiliation. Lisa was relentless with her drive to push
his limits, and never tired in seeing his face blush up almost to the
point of explosion.

On day three, she had sent him to school dressed completely as a
bridesmaid, with all the fancy matching bridal lingerie underneath. With
everything made of either silk or satin, combined with his hairless
state, Paul couldn't help but be sexually turned on by all the soft
fabrics caressing his body. For the first time ever, instead of wearing a
thong, his sister chose for him full bottom panties made of pure satin.

As soon as Angie had seen him that morning, she had passed her hand along
his back and rubbed his full slip through his dress, confirmed he was
wearing a bra, and teasingly asked him if he liked wearing such a girly
clothes, as her hand paused and started massaging his pantied ass. Even
without the vibrating butt plug, that was left behind that morning, Paul
still managed to get an embarrassing erection thanks to Angie's playful

"Looks like you do," Angie mockingly sang out, as a bulge slowly started
to appear beneath the dress.

Then, right after his second class, that same morning, he and Ryan, the
other newbie on the swim team, were rounded up and force fed a few Jell-o
shots. Spiked with Viagra, Paul and Ryan embarrassingly showed up at
practice an hour later supporting enormous boners under their towels,
totally unable to will them away. Ryan, going first for the lottery game,
ended up picking a string bikini to wear for practice, where as Paul on
the other hand had the misfortune of choosing a blank piece of paper and
had to lose his towel right there and then on the spot, in front of an
even bigger crowd than from Monday.

If practicing his dives completely naked, totally hairless, and having an
embarrassingly erect during the whole time wasn't bad enough, a
watermelon was presented to him at the the end of practice, with the
warning that his daily thirty seconds of humiliation was due.

The swim team that day had covered a watermelon with vaseline, dumped it
in the deep end of the pool, and had all the new recruits try to bring it
out. After the exercise was over and it had finally been brought up,
Trish and a couple of other senior girls came up with an evil plan.
Cutting away a small hole and greasing the opening with the left over
vaseline, they called Paul over and pretty much ordered him to fuck the
giant piece of fruit.

"I say he cums in thirty seconds," egged on one of the girls.

"Twenty bucks say he doesn't," challenged one of the senior boys from the
swim team.

With bets being placed, and a stopwatch being brought out, Paul was given
a countdown telling him when to begin. Once 'Go!' was yelled out, he
closed his eyes and penetrated the watermelon praying he wouldn't cum and
that the thirty seconds would just fly by.

Guys were shouting at him to be a man and not to cum, where as the girls
were doing the complete opposite, wanting both to win the bet, but also
for the sheer pleasure of seeing Paul ejaculate into the giant melon.

With Angie practicing her front flip on the three meter diving board
right in front of him, Paul couldn't help but look and get turned on as
she she bounced up and down in order to get enough height. Having picked
Pauls' baby blue speedo during the lottery game, she did it much more
justice than he had, especially with her gigantic boobs jiggling up and

Thirty seconds of watermelon fucking and watching Angie in the background
putting on her show, Paul made his trademark fuck face and started
cumming the second the melon was removed. Long strands of cum flew in the
air, hitting some of the girls, who didn't seem to mind at all, having
just gotten richer thanks to his performance. Instead, teasingly
congratulated him and sent him off the showers and asked him if he needed
any help putting his dress back on.

Telling them it was okay, that Ryan was going to zip him back up, just
like had embarrassingly unzipped him when he got there earlier, which of
course the girls found funny and began teasing Ryan relentlessly.

Thursday the DPD sorority held a tea party after school, where all the
male pledges had to server them all, wearing only bow ties. Everyone
except Paul. All he wore was a garter belt, seamed stockings, and a pair
of poofy three inch mules. The event was to repeat history, after Lisa
heard her mom tell of her story, which finally turned into a huge

That day at school Paul had worn a very short flower girl's dress that
barely covered his stocking tops. Sitting was difficult for him, as well
as simply walking around, not being used to the heels.

Friday was was pure hell for Paul, due to one of the school's oldest and
most perverse traditions. Both Fridays during the initiation weeks were
also known as 'Underwear Day', where all the pledges showed up at school
wearing only their underwear.

Along with creme coloured satin bikini panties, Paul was made to wear
stay up thigh-highs, three inch heels, and a very lacy bra. Shocked that
for the first time he hadn't been given a training bra, but instead a bra
that had rather large cups, Paul was even more shocked when he saw the
box of breastforms sitting on his desk.

Seems Lisa had a friend that worked in a sexshop, and with the help of
Roxy, they got him a pair of state of the art breastforms at a very low
price. They came with medical adhesive, so right after his morning
shower, both his mom and Lisa glued them in place. Jiggling with every
move he made, it took him quite a while to get used to them.

That day at diving practice Paul slipped into a string bikini and looked
so feminine, thanks to his new boobs, that the girls decided he was going
to have to wear a bikini for the three remaining practices they had next
week. Instead of making him pick during the lottery game, they would have
him put on one of the three other bikinis they had in their arsenal.

During the entire weekend Paul had to endure wardrobe changes to keep his
sister happy. She had him in skirts, summer dresses, cocktail dresses,
slinky dresses, tight fitting dresses, party dresses, not to mention all
the sexy sleepwear that she had outgrew, and had filled his drawers with.

With all the modeling that Paul did, Lisa picked out the four his was
going to wear that week and hung them in his closet. All four were
extremely girly and made Paul cringe knowing he was going to parade
around school wearing them.

His new designated panty drawer was also filling up rather quickly, much
to his dismay. He had a good mix of bikinis and thongs, all made of
either satin, nylon, or silk. All of course had little girly bows, hints,
if not full lace decorating them. Each time he opened it, he almost
wanted to jump back. He knew his sister was adding way too many, and
knowing how their mother was about not throwing away clothes that hadn't
worn away yet, he was afraid he was going to inherit them for good.

With all the feminine dresses Paul wore to school that week, had all the
appropriate undies that went along with them, including of course his new
rack. On his small frame, the fake boobs made him easily a D cup. And
just like the previous week, his sister always left out makeup or any
type of wig. She wanted people to know his face, and so far Paul was
almost a star at school, considering all he had endured so far.

Leading up to Friday, the big day, Paul's anxieties grew to their highest
as final day was finally in his sights. Besides being another 'Underwear
Day', and last diving practice that included hazing, it was also the day
of the pledges had their final challenge: 'Strip Poker Night' at the DPD
sorority house.

Not only were the male and female pledges playing against each other for
their clothes, once naked, the losers were going to have to put on a sex
show for the winners. It was a way to ensure many virginities would be
lost. In the past, a lot of boys and girls ended up popping their
cherries after the game, with the winners there as an audience cheering
them on. On occasion some girls had been forced to go down on each other,
to the great delight of the boys watching, but so far, no two boys had
ever been forced to engage with each other sexually. So far.


Arriving at the sorority house wearing a big poofy prom dress made of
pink satin, Paul felt pretty confidant for once, knowing he was a pretty
decent poker player, and that if he played his cards right, he would
finally get his first blow job ever, and that it would be from one of the
hot sorority girls he'd been lusting over for the past two weeks.

Names were picked out of a hat where two girls and two guys were assigned
to one of the many poker tables scattered around the house. Paul's heart
skipped a beat when he saw Angie already sitting the same table he had
been assigned to, and immediately started fantasizing her on her knees in
front of him, shutting her up by forcing his dick into those smug lips of

Ryan was also at the table, as was Melissa, a gorgeous red head he had
seen in his classes, and who had a body that was absolutely perfect.

Having only lost his heels and stockings in the first half hour, Paul
started getting cocky with his chip lead, and started losing hand after
hand, as well as more and of his girly attire.

Twenty minutes later the game was almost over and the competition was
incredibly fierce. Melissa had lost everything and had been forced to go
down on Angie who only had her panties left. Hearing Angie moan as
Melissa ate her out over her panties was such a turn on for the boys that
both of them had sat with their mouths open and got instant erections as
the girls' three minutes of shame clicked by.

With Paul being the only other person wearing an article of clothing, a
pair of pink polka dotted bikini panties, and Ryan losing his diaper the
previous round, it was down to the last hand.

Melissa, having already performed her embarrassing forfeit, was only a
bystander for the final hand and cheered Angie on, as she took on the two
boys in this winner takes all match.

If Paul were to win this next hand, he had already decided prehand that
Angie would be the one sucking him off, an he was going to make Ryan eat
out Melissa. If Ryan won, Paul figured it would be vice versa. If Angie
were to win... Paul didn't want to even speculate on that one. As the
cards were delt, and all three of them getting good starting hands, it
wasn't long before everyone's chips were pushed in the middle.

As other poker games were finishing, and blushing teens who had just lost
their virginity were exiting their rooms, not to mention all the senior
sorority girls who were checking up on each individual game, quite the
crowd amassed around their table to witness the final outcome.  

"Re-raise..." announced Paul with confidence, as he made his straight on
the river, sure in his heart that Angie hadn't made her flush with the
same card, he moved "...all in". Ryan could only wait there squirming,
wondering if his three of a kind was good enough to beat Angies hand.

"CALL!" screamed Angie with an huge smile on her face, as she laid down
the the nut flush. This of course made all the girls jump up and down in
joy all giggly, knowing they were finally going to see some guy on guy

"Looks like someone going to get a blow job after all" announced Angie,
as the other girls were now giggling non stop, all anticipating the
inevitable outcome.

"SIXTY-NINE! SIXTY-NINE! SIXTY-NINE!" the girls chanted over and over, as
Angie turned to the two blushing boys with a smirk and said, "I think
that's an excellent idea! Hop on the table boys... NOW! Ryan, get on op
of Paul, I want him on the bottom, and don't start until we tell you," as
a stopwatch was produced.

After clearing the chips and cards out of the way, the two sheepish
looking boys climbed onto the table and positioned themselves into the
most awkward situation they had ever found themselves in their lives.
Which each of them having each others dicks just inches away from their
faces, both of them simultaneously mentaly said 'fuck it' and started
sucking each other off the second "GO!" was screamed out to them.

"Wow... check it out, they're both getting hard!" squealed a pretty
blonde who had noticed their growing erections right away.

"That's it... fuck his face," encouraged Lisa who had just arrived along
with Roxy, as she saw her little brother in the most compromizing
position of his life.

"Look at them go," mocked Roxy as she got closer.

"Is he doing a good job princess?" asked Lisa teasingly as she looked him
in the eyes, just as he was reaching the point of no return.

"Geez... it's been two minutes and it looks like they're already cum,"
egged on Angie, which made the crowd of giggling girls chant anew, but
this time it was the word 'CUM!' the screamed over and over.

With both of them grunting and approaching orgasm, both Paul and Ryan
increased their pelvis motions, until finally they couldn't hold on any
longer and started unloading in each others mouths. With a couple of
final humps given by each of them to each other' mouth, the boys were
ordered to swollow each others cum, and to make sure their little peepees
were completely licked clean.

Technically speaking, as Paul got off the table, the initiation was
supposed to be over, and no more could be asked of him. But because he
was a third generation pledge and all, they sent him home without his
dress. Not only that, but they also refused to give him any his lingerie
back. They wanted him to make his trek back home completely naked. And to
add salt to the wound, they even handcuffed his hands behind his back,
and tied to a string, they put the key to the cuffs around his neck.

Heading back home, Paul couldn't believe he was walking down the sidewalk
without a stitch of clothing on, and totally incapable of covering
himself up. Hiding behind trees when car lights appeared, he finally made
it home and had to ring the doorbell with his nose, praying to God his
mom wouldn't make a big deal out of the whole situation.

She almost fell on the floor with laughter when she opened the door, and
in doing so, she blocked the way, which left Paul still standing outside.

"Come on mom! This isn't funny!" he whined as he waited to get in.

"No, actually it is," she went back into her giggles before continuing,
"I mean... you do realise you're naked right?" as she returned to laugh a
little more before finally letting him in.

"So tell me what happened? I want to know all the juicy details!" she
inquired as she shut the door.

"I''ll tell you all about it in the morning, ok? I'm just glad it's all
over... if you could just take the key that's around my neck and uncuff
me, you have no idea how grateful I would be," Paul pleaded in his mind,
as he finished his sentence, that she wasn't going to prolong his agony.

"First, you're going to tell me all about it... NOW!" she almost yelled,
"And stop fidgeting around, I know you have a small penis. I mean it's
right in front of for God's sakes!" she snapped, as Paul finally
straightened up a bit, which made his mom let out a small giggle.

"Wow, it relly is small, eh? Even smaller than your fathers. I'm sure
he'll be happy to hear that. Even without any hair, instead of making it
look a bit bigger, it looks prepubescent," she mocked a little further
before demanding to know about the details of his last day.

Telling her about most of the embarrassing events that occurred to him
that day, just leaving out the conclusion of the poker game, she finally
uncuffed him and congratulated him for finally making it into the
fraternity, and sent him to bed with a playful slap on the ass.

Entering his room, Paul immediately went to his calendar and crossed off
the final day of his initiations. He had previously highlighted his two
weeks of hell just before it began and had been checking off each day as
the weeks progressed.

So tired and exhausted, he went straight to his bed and opted to sleep in
the nude. Knowing he was only going to get his regular clothes back in
the morning, instead of putting a pair of panties and nightie, Paul
decided to sleep in the buff.

**to be "slightly" continued**


  1. I remember reading this when it came out. I wish it had went on longer. Like maybe making him attend an entire semester as a girl.

    Annabelle, have you ever read the story College Girl? I cant remember who it is from but that is about a boy entering a sorroity as a girl and attending college as a girl.
    It starts out just as a challenge for equal rights. He wants to enter a sorority
    He doesnt really expect them to accept it but they do and tell him that he must follow the rules if he is to really do this. Now he issued the challenge, he cant back down so he goes along with it and has lots of fun.
    It isnt really forced or humiliation, he has fun with the girls engaging with them as a girl in college. Its a fun story and I think its on Erins Big Closet site.
    Its a very long story but you may like it.

  2. Sorry of like Buffy n can't think of other one where two guys couldn't afford rent n college, unless they joined the girls sorority. Can't remember the sitcom.

    But back to your sorry. Very nicely written. Think he should have gone full time, as think he was starting to like it

    1. I'm glad you enjoyed the story! Humiliated on Halloween by this same author is another you might enjoy.

  3. On his bed, Paul found girly gear laid.
    Festive and dainty clothes he was made
    To wear with giant falsies,
    Designed to better please
    Not a bride, but always the bride's maid.

    For Ryan and Paul swim team hazing
    Proved exciting and quite amazing.
    Viagra-spiked Jello-shots
    Energized their cocks lots.
    Naked Paul dove with his cock raising.

    What followed, I blush to be tellin',
    Was a game with a greased watermelon.
    Paul's stiff cock filled
    A hole which was drilled
    Humping it, 'I'm cumming' he's yellin'.

    Now Princess Paul was a sight to see
    At the Strip Poker Night at D.P.D.
    With make-up, wig, and falsies
    Paul was sure bound to please
    As many pledges lost their virginity.

    For the rules meant when you lost a game,
    Your virginity would be forfeit the same
    That is, lost to those
    Whom the sorority chose.
    Paul hoped Angie would be the one named.

    But games of chance demand more than luck.
    It depends on who at the table you're stuck.
    When Paul shouted 'All in!'
    Angie called with a grin.
    Ryan and Paul, each others cock had to suck.

    On the table each boy was made to recline.
    Naked and erect, they performed sixty-nine.
    All the girls had fun
    Watching the boys cum
    Swallow and lick to make their cocks shine.

    Their hazing was officially at an end.
    But Lisa decided it okay that they append
    Even further humiliation
    On Paul, third generation.
    Homeward nude and bound, him they did send.

    This was an excellent tale, I'm sure all agree.
    It shows humiliation can exceed mere nudity.
    Most girls love to deride
    A Sissy's feminine side.
    For nude boys with tiny wienies are fun to see.