High School Dilemma Parts 3 4 5

June 8, 2011

Parts 1 and 2 here: High School Dilemma

“Well Sissy you are definitely a girl. Girls often have accidents so get use to it. It’s something to do with the length of your urethra to your bladder. Don’t you wish you had a penis?” Sean taunted me.

“Yes Sir,” I answered.

“Yes Sir what Jill,” Sean taunted.

“Yes Sir I wish I had a penis,” I answered.

That’s when Sean began telling Uncle and Tiny how I really didn’t have a penis but instead a slightly enlarged clit.


Date: Tue, 24 May 2011 19:47:10 -0700 (PDT)
From: lauren westley
Subject: High School Dilemma Part 3 – Lauren Westley -TG

(Authoress’s note: of course all disclaimers are still in place regarding
characters etc. This particular episode is very XXX with pee scenes etc. I
suggest those who don’t like this kind of story not to read on. I know I
make both grammatical and punctuation mistakes. I promise all of you I will
try harder every time to get it right. Hey what else can a submissive do?
However, I do know many parts of my stories will not appeal to all of
you. I only wish there is enough to make each of you happy. To those who
have given me constructive criticisms as well as those with praise
thanks. Lauren Westley. (fundipity@yahoo.com)

High School Dilemma

Part Three

By Lauren Westley

Walking with Sean was an ordeal I was so filled with cum and pee and the
butt plug pushed even harder on my bladder. I didn’t know where we were
going until we got to the kitchen.

“Where are the glasses,” Sean asked?

I pointed to the cabinet. Sean walked over and found one of those big beer
glasses. You know the kind they give you at a brewery. This one had
“Budweiser,” etched into the glass

Sean said, “Perfect, ” as he took the glass and instructed me to get four
more beers from the fridge for the guys. Then he walked out of the kitchen
with the glass leaving me to my misery.

I opened the refrigerator door and saw what remained of the beer Jimmy had
brought over. It was on the lower shelf and I had to bend down to get it. I
didn’t dare deep knee bend so instead I bent at the waist and felt my skirt
ride up and the plug trying to push out of me. Walking back to the living
room with the tray of beers I felt the pee inside me sloshing around. I
worried about an accident and also felt emotionally like crying. Joe’s cum
was drying against my balls and tiny penis.

I heard Joe on the phone in the living room saying, “Sure, come on
over. The more the merrier. We have a great little cunt bitch here for fun
and games.”

So quickly had I sunk into depravity? I didn’t even hear Sean when he
called me over. He was standing there with his flaccid cock hanging out
through his zipper.

“Come over here Jill,” he beckoned me with the glass in one hand.

As I waddled over wondering what the other guys were thinking when they
looked at me Sean lowered the glass and dangled his penis into the
glass. Sean started peeing a good steady stream and the glass turned from
clear to dark yellow with foam forming at the top of his piss. In horror I
watched knowing what would come next. My throat was dry but not from

When I got over to where Sean was he was almost through peeing. The glass
was full with piss and suds to the brim. Paul commented how it looked like
dark ale. Sean handed me the glass saying, “This Bud’s for you,” and then
commenting how since the toilet was full there should still be room in the

My long fake pink nails wrapped around the warm glass and my stomach

“This is the finest filtered lager Jill. We drink the beer and then we
piss it out for you, our little slut sissy girl. So smell the brew and then
drink it down,” Sean mockingly said.

The pungent odor stung my nostrils as I inhaled.

Sean put his hand on my tummy saying, “There’s plenty of room in here

I brought the glass to my quivering lips taking a little sip but Sean told
me to take a gulp. The acrid taste coupled with what it was going in my
mouth made me nearly puke. My tongue piercing clanged on the glass

“Drink it all down right now,” Sean said, “or I’ll put a shit floater in

Scared, frightened and terrified I drank. Sean’s piss was washing down over
my tonsils and drowning my throat as I was coaxed to chug-a-lug. Down,
down, down burning a pungent path into my stomach. I felt bloated. My
stomach began to tighten against the waist of the little black skirt I was

Even though earlier I so wanted to empty my bowels I wasn’t allowed to but
for the next half hour or so they didn’t bother me either. Sean’s piss was
working its way through my system into my bladder, which pressed against by
the other pee inside me. Inside their, “toilet.” Who knew how perverted
these guys were? I can’t imagine what they plan.

That’s when the doorbell rang and Joe told me to, “Waddle over there and
see who’s at the door Jill?”

I was sobbing as I walked to the door. The little bars through my nipples
ached under the pink spaghetti strap camisole. And I had to look down so as
to not fall down in the black open toe heels I wore. My pink toenails and
pink fingernails visible. Inside I hoped the tattoos were done in washable
ink. At least Sean had said they were something that would wear off in a
week or two. And as soon as this was over I’d remove the tongue bar and the
nipple piercings. The pierced ears I could either remove or simply wear
them since guys did that now. My urge to pee was growing dire.

With my hair blond and curled coupled with my diminutive size I felt like a
girl as my hand turned the knob of the door. Talk about shock and awe. I
opened the door and their standing on the stoop was an old fat guy and a
midget. The fat guy was carrying two cases of beer and the midget had a

The fat guy said, “You’re the little sissy girl my nephews told me about

I tried to stammer “yes,” but words wouldn’t come out.

As they walked inside Joe called out, “Is that you Unc?”

“Yeah, it’s me and Tiny,” his uncle replied.

Tiny put his hand on my thigh and I started to back away.

“Joe, I thought this sissy girl was trained. She just backed away from
Tiny’s touch,” his uncle called out, as the three of us were so close to
each other in the small vestibule Joe’s uncle’s belly grazed against mine.

Joe screamed out, “Bitch you let Tiny do whatever he wants and anyone else
or you will find these past hours to be a walk in the park.”

Tiny reached back under my skirt. I was frozen in place. Uncle pushed his
belly past pushing me a bit into the wall as he walked into the living

Tiny’s hand came around touching my butt plug that caused me to moan from
the urgency to need to pee. He directed me to walk into the living room as
he handled the plug. I was mortified.

“Hey Joe why does the sissy have her pussy plugged,” Tiny asked?

Almost at the same time Unc was picking up my piss glass from the coffee

Joe said to Tiny, “Ask her Tiny.”

“So sissy why did you plug your pussy,” Tiny asked me?

He had let go of my thigh and was now right in front of me. I was
hesitating answering out of extreme embarrassment when Jimmy walked up to

Pulling my hair so my ear was pressed against his lips Jimmy whispered in
my ear saying, “If you don’t answer every question asked truthfully and in
a sissy voice I’ll shit down your throat and sissify your larynx into
submission. Now answer the man.”

I tried to answer but my throat caught all the words and what came out was
barely audible.


Jimmy slapped my ass hard whispering, “Start your answers with ‘Sir’.”

I felt the pee sloshing inside me as my ass stung from Jimmy’s hard hand
slap across my ass. I wondered if Jimmy could feel it? What did the other
guys think? Who am I?

“Sir, my ass,”


“You don’t have an ass anymore pussy girl,” Jimmy snarled in my ear.

“Sir,” I said to Tiny feeling the roots of my blond curled hair being
pulled taut by Jimmy holding my head to his mouth. It felt like a thousand
bee stings, “My pussy is plugged because the men fucked me and filled me
with their cum and pee until I was full.”

“So your pussy is full with man piss,” Tiny asked?

Jimmy whispered in my ear what I should say and also reminding me at each
step that my voice should be a submissive sissy tone.

“Yes Sir,” I answered with a sissy sound from my mouth.

Continuing as Jimmy instructed I said, “My pussy is also a toilet. My
toilet pussy can only hold plenty of cum but only three man loads of piss
so until I learn to hold it without leaking I need to wear a pussy plug for
training. Someday I’ll proudly carry three man loads without a plug.”

My heart was sinking as the thought of many times being filled with pee
would be a reality for the next two weeks.

It was right about then Unc held my glass up and asked, “Whose glass is

Jimmy was still instructing me what to say.



“Sir,” I answered in my new sissy lilt voice, “it’s my piss drinking

“So you like to drink piss too,” Unc asked?


“Yes Sir, man pee is tasty beer to a sissy,” through my tears I answered.

With more prodding from Jimmy I continued, “But I can only hold two full
glasses of pee in my girlie tummy at this time.”

“I’ll bet you have a magic marker somewhere around here,” Unc said and then
he instructed me to go get it.

Jimmy let go of my hair and slapped my ass one more time. More of a slap
you’d give a girl when she was sent to go get something so it wasn’t very
hard just a light sting but it was humiliating.

I started to waddle off to get the marker when I heard Larry say, “She
walks real sexy. Do you think it’s the piss or the plug?”

Sean answered, “Well it’s probably both right now but I’ll bet when she
outgrows the plug and has a good filling she’ll have a great sexy sway.”

I was crying inside. Scared of doing what they wanted but more scared of
Jimmy’s threat of shitting down my throat I walked to the kitchen to find
the marker. Inside I knew I had now traveled to far down this road to
escape and it was only the first day.

In the kitchen I found the marker. Leave it to my Mom to have bought a
magic marker in ‘hot pink’. Carrying it back I knew someone would make a
wise crack about it.

Paul didn’t talk as much as the others so I was a bit surprised when I was
walking back to hear his voice directed at me.

“The best way for you to walk girl is to put one foot in front of the other
like a runway model but not so pronounced. That will help you both from a
feminine perspective and also if you squeeze your vagina tight you’ll be
able to hold our cum and piss without leaking.”

I handed Unc the magic marker.

He handed it back to me with the glass saying, “Now print this neatly on
your glass.”


I knew the consequences but I was also in too deep. I handed the glass back
to Unc with the words as neatly printed in hot pink.

“Joe, I think our little sissy girl should be clearing the empties and
properly serving us,” Unc said.

“Great idea Unc,” Joe replied and then he turned to me saying, “Jill while
you aren’t being used you should be serving and cleaning up. Sweep the
floor, clear and wipe the table. But stay busy.”

This was my own house but now I was the maid as well asÿtheir slut. My
panties were stuck to my balls. Joe’s cum had completely dried. I hadn’t
even thought about the loads of piss and cum still deep in my ass. The plug
was becoming second nature. But my need to pee was also becoming more
urgent but still I wasn’t given permission to use the bathroom.

I cleared the empty bottles, wiped the table and brought the guys
beers. Tiny had brought a handle of Wild Turkey in the brown bag. The guys
were getting drunker and I was having all sorts of feelings. The chain
linking my nipple bars had just the right movement and weight to remind me
of my nipples nearly all the time. I wondered if that’s how a girl felt.
When I came back into the living room I noticed my glass on the table
filled with dark urine. I cringed inside.

Unc noticed my face and then said, “Go ahead girl drink up.”

I didn’t want any ‘shit floater’ or whatever else Jimmy had in mind so I
picked up the glass. Again I could feel how warm it was. I knew I was
supposed to sniff it so I did and it was even more pungent as the glass

Unc asked Joe where I had learned that to which Joe replied, “Oh that’s
just something she likes to do. She wants to become a ‘piss
connoisseur’. Several of the guys guffawed over that comment. Tiny
mentioned I should keep a journal of the smell and taste of piss.

As I tilted the glass back and I could see some of the magenta print, “Piss
in Here, Jill.” I was ashamed as the men watched me but the most
embarrassing moment came as I was drinking the glass of pee when Tiny
quizzically asked, “Is your pussy leaking sissy?”

Unbeknown to me since I was so distracted by everything else my bladder had
started uncontrollably leaking pee out of me.

“I asked you sissy are you leaking,” Tiny asked more stridently.

Jimmy glared at me.

“Yes Sir,” I quickly answered in a voice strange to me but now the only one
I was allowed.

Although I couldn’t see it I was now aware of the pee dripping through my
cum filled panties and puddling on the floor. Once it started I couldn’t
stop it. I just peed. The flow became more constant. A steady stream

“Keep drinking sissy,” Sean said.

So the warm piss washed down my throat as I peed. I wanted to vomit but
instead I simply dry heaved into the glass of piss making it so much worst.

Fortunately I wasn’t on the carpet when I lost control of my bladder but
instead standing on the wooden floor.

“Well Sissy you are definitely a girl. Girls often have accidents so get
use to it. It’s something to do with the length of your urethra to your
bladder. Don’t you wish you had a penis?” Sean taunted me.

“Yes Sir,” I answered.

“Yes Sir what Jill,” Sean taunted.

“Yes Sir I wish I had a penis,” I answered.

That’s when Sean began telling Uncÿand Tiny how I really didn’t have a
penis but instead a slightly enlarged clit.

“Girl we have to see that,” Unc said. Then he continued with, “go get some
towels to soak up your accident first.”

Now I’m sure some of you are wondering why I didn’t just run away by now
but remember this humiliation had begun a week ago and it just seemed to
progress beyond my brain thinking of any alternative other then Jimmy’s.

I found some brown towels in the linen closet and brought them back.

“Just drop them on your pussy juice,” Tiny said.

A few minutes later I was standing there on the edge of one of the towels
with my panties to my knees holding my skirt up as Unc and Tiny examined my

“Wow that’s small,” Tiny said, “and you say it doesn’t get much bigger then
a pinkie when it’s erect?”

“Yep that’s right isn’t it girl,” Joe said.

By now I knew I need to answer quickly and more then just a yes so I said,
“Yes Sir my clitty is just a nub.”

I had read that some girls call theirs a nub. I wasn’t sure of the complete
meaning but it met with approval. And at this point I was beginning to try
to win approval since I thought it would mean an easier circumstance.ÿ
However the next moment proved otherwise.

“Hmmm…those towels are perfect,” Sean commented. “Kneel down on them and
stick your pussy up in the air Jill.”

I didn’t think I had hesitated but Joe slapped my face almost as hard as
the first time a week ago when he said, “don’t” when he was peeing on my

I knelt down.

“On your elbows, face in the towels,” Joe said.

My naked ass was high in the air and my face was in the pee soaked
towels. Pee from two men and a sissy.


Two hard slaps across my bare ass got my attention.

“We are going to remove the ‘toilet plug’ girl,” Joe said. For a nineteen
year old man he was quite sexually deviant. “Don’t let the toilet overflow
no matter what,” he said mockingly.

I felt the plug slowly open my hole as the fat end started to be pulled
out. I felt like I was going to explode.

“Remember, squeeze those vaginal muscles as your pussy plug comes out,” Joe

PLOP! it was out and I was squeezing my sphincter or as Joe said ‘vaginal’
muscles closed when suddenly someone started slapping my ass. Harder and
harder they slapped. I started crying and then I couldn’t hold my hole
closed anymore and all the pee and cum just shot out of me.

“Stop that girl,” Joe said.

I tried but I couldn’t I cried and cried and felt relieved. Finally I had
stopped flowing pee and cum.

“You’ve been a good girl,” Joe said, “go clean up this mess. Wash
everything. Take a nice hot bubble bath and when you come out we’ll see
what you should wear for tonight.

I picked up the heavy towels and sulked away. Shortly after the washer was
churning the towels through detergent and I was naked in a warm bubble
bath. As told I left the door open to my sister’s room and her bathroom
door. I was not allowed to close doors. I could hear the deep male voices
downstairs. Though I couldn’t hear what they were saying I wondered if it
was about me.

Date: Thu, 26 May 2011 16:44:46 -0700 (PDT)
From: lauren westley
Subject: High School Dilemma Part 4 by Lauren Westley TG

(Authoress’s note: of course all disclaimers are still in place regarding
characters etc. This particular episode is very XXX with pee scenes
etc. However, I do know many parts of my stories will not appeal to all of
you. I only wish there is enough to make each of you happy. To those who
have given me constructive criticisms as well as those with praise thanks.
Lauren Westley. (fundipity@yahoo.com)

High School Dilemma

Part Four

By Lauren Westley

A bubble bath is one of the truly feminine moments one can have
privately. I luxuriated in the hot water cleansing all my earlier
sins. When I lifted my leg out of the bubbles I noticed how very feminine
the curves on my calves were. I had never paid attention to that
before. But with my blond hair now gone from my legs it seemed as if a
woman had attached herself to me.

Lathering the soap in my hands I rubbed my leg and the smoothness was

I don’t know how long I bathed but it seemed like forever. When I washed my
ass I thought back to what was earlier inside there. For a moment it felt
like I was rubbing my pussy. That’s what they had said it was. And now I
had two weeks to be what? A pussy? A TV? A TG? I wasn’t sure anymore only
that there were a number of men downstairs who got hard playing with me and
liked to cum in and on me. In one brief moment I felt there was power in
making a man cum.

Distracted I hadn’t noticed Joe standing in the doorway watching me.

“I see you are beginning to enjoy this,” he said.

When I turned I found I instinctively slid deeper into the bubbles.

“Anyhow, when you are done you will find a pair of panties and heels on the
chair by the bed. That’s all you need to wear tonight. Make sure to make
yourself extra pretty and don’t forget what you’ve already learned,”

Joe said.

Then he left. It was almost a dream except I was in my sister’s tub and I
knew the past day, the past week, was real.

I got up and drained the tub while drying myself. There was a full-length
mirror where I looked at myself. Except for my tiny cock, now just a large
clit, I really looked like the girl next door. Also it seemed as if the
tattoos were already fading. I wondered if it was my imagination or that
Sean had told the truth.

Looking in the mirror I saw the small writing on my left breast saying, “I
love to lick ass” and the chain connecting the two nipple bars.

Sticking my tongue out the tongue bar looked so gay. I couldn’t read the
ankle writing but it was easy to read “Sissy Clit” just above the base of
my penis.

Getting the hand mirror I focused on my back. The little butterfly with the
words written in a half moon above said, “Pull My Panties Down.” Not far
below and just above my ass crack were the words, “Piss & Cum” on the
horizontal with “IN HERE” below with a stub arrow finishing just in my ass
crack. Lower down on my left cheek in large script it said, “Spank” and on
my right cheek, “Me.”

Well my reddened ass simply verified the words.

I held me ass open to see if I had any damage. There was none. It looked

In the bedroom I found the white satin panties. The front was shiny satin
and the inside crotch was cotton. I wondered why as I held them up.

Turning them around I could see the backside was very sheer. See through
actually. Sliding them up my legs it felt sexy. My clitty (I needed to
focus on that if I didn’t want to get in trouble) hardened a bit and that
made my cheeks flush.

Back to the bathroom and the small vanity I went, I sat down and looked at
the 10x mirror on its stand. A touch of a button and a ring of soft light
shined on my face. Gosh it seemed weird how big my pores were. I had sat
here earlier but this time was different. I’m not sure exactly why but it
was something along the lines of, `been there done that.”

The chain pulled my nipples just a bit each time I moved. I thought of
Joe’s words, “make yourself extra pretty,” as I started to put foundation
on watching myself change to even more girly. The hardest part was the
eyeliner pencil. The second hardest was getting the lipstick right.

Fortunately my sister had some index cards with what to do. She was always
impeccable in how she looked and I guess this helped her get ready. I
hadn’t used the mascara before or the funny thing to curl your lashes. But
I figured I’d better do everything really well or else Sean and Jimmy would
do something worse to me. Finishing up with the lip-gloss I stared in the
mirror. It was a transformation. When I finished brushing my curls there
was no way some the neck up someone would think I was a boy.

Perfumed and in heels, pink toenails and fingernails, all dolled up I
walked out of the room and headed downstairs. If was night and I could hear
the men laughing and talking. The TV had some sort of game on but as I came
downstairs a couple of the men turned from the TV and whistled. I had
arrived for their pleasure tonight.

There in the room was Joe, Sean, Larry, Paul, Jimmy, Tiny and Unc, oh and
of course me.

“Hey Jill clean up this place and get us some more beer,” Sean said.

Just the word `beer’ made my bowels growl.

Now my house isn’t one of those immaculate places but still the empty
bottles in the living room was a bit of a mess. At least they had me stay
on top of it so I didn’t mind cleaning up and bringing them beers. Turned
out they were watching a baseball game. Was only the second inning but they
were engrossed and they didn’t bother me when I brought them their
beers. The refrigerator had whittled down their stash and it was nearly
nine pm so I figured they’d be going home soon or at least when the game
was over. Besides the beer I only had some celery and carrots in the
fridge. I hadn’t gone shopping yet. I was hungry and figured I’d ask if I
could eat something.

“Sir,” I said to no one in particular, “I’m hungry may I get something to
eat from the fridge?”

Sean answered, “What do you have in there? We’re getting hungry too.”

“Sir, there are only carrots and celery,” I replied.

“Haha, real girl food. Go ahead and help yourself,” Sean said.

As I went to the kitchen I heard Sean ask the other guys something about
Pizza. When I was in the kitchen eating celery and carrots Joe’s voice
echoed in. Joe has a deep penetrating voice. I thought I heard him ordering
a Pizza. This meant they’d be here for a while.

I had finished eating my celery and carrots when the doorbell rang.

“Sissy go answer the door,” Sean commanded My stomach churned again
thinking it was the Pizza delivery guy.

Someone who came to our house regularly and here I was in just white
panties and heels. The bell rang again.

“Hurry up Sissy it’s our Pizzas,” Sean called out.

I knew I’d better do it. I had done so much already what choice did I
have. I walked to the door with one foot in front of the other knowing my
ass was swaying for the men to see. But at less I was empty and no plug

Opening the door I gasped for air. It was some guy holding three boxes of

“Hey Jill take these,” he said handing me the pizza boxes I carried them in
with the smell of pizza wafting through the house wondering how he knew my
name. And almost as soon as I had put them down in the kitchen the guy at
the door was in the kitchen too with two 24-can packs of Budweiser.

“So Jill you’re the sissy cunt my nephew was talking about,” he asked?
Without hesitation I answered, “Yes Sir.”

“Put these in the fridge,” he said pointing to the beer.

While I was putting the beer away I heard Joe talking to him.

“Jim, you rock.”

As soon as I was through I went back into the living room.

“Spin around girl. Let’s see what you’ve got,” Jim said.

There were hoots from the guys as I spun around and when I was finished Joe
pointed to a spot where all the men could see me and told me to dance like
I was a stripper till I was told to stop. Now I was a pretty good dancer so
it wasn’t too hard for me to mimic stripper dancing. While I was dancing
Jim opened a paper bag and I saw some papers and a bag of weed fall onto
the table.

“Give us some crotch action, Show us how you want dick in your pussy. Tease
us,” Joe instructed as Jim began rolling a joint.

It was then I remembered what I was here for as I spread my legs and pushed
my hands between my thighs pushing them out and dancing like a whore
stripper. Jim lit up the joint and brought it over to me. Jim was about

medium build with long brown hair in a ponytail. He had me take a hit.

“This should make tonight go better for you, ” he said.

A couple of hits and I was stoned. The third hit instead of me puffing on
the joint Jim leaned into me kissing my pink lips pushing his tongue into
my mouth and when it opened exhaling into my mouth. I was stoned. A man had
kissed me and it went from repugnant to interesting in just a few seconds.

Jim stayed with me as the other guys started lighting up joints, drinking
beer and hooting about Jim kissing me.

Looking into Jim’s grey eyes and pretty face I was lost until he said,
“You’re going to fuck the shit out of me tonight girl.”

It brought back the comment of Sean’s about a `shit floater’ and Jimmy’s
`shit down your throat.’ All the talk of shit just made me cringe inside
and act more girlie outside.

He took my hand and placed it on his crotch. I could feel his balls and

“Bet you’d love to suck this cock and have a hot rod in your pussy. Right?”

Didn’t take much but that word shit to get me to answer in my sissy voice,
“Yes Sir I’d love to suck you cock and feel it cum in my pussy.”

Jim pulled gently on the chain and my nipple pulled out a bit.

“So you like my cock right now. Right Sissy?” he inquired.

“Yes Sir,” I answered “Then unzip my fly,” he said.

My fingers gripped his zipper. The metal purred as I unzipped him.

“Reach in and find the man your lips were made for,” Jim said.

As I fished his cock out of his pants Jim put a hand on my head pushing my
blond curls sending a signal to my knees and I folded to the floor.

When I saw his cock I was amazed how it had a small mushroom head “Lick

I did but as my tongue surrounded his mushroom head the thought of anything
like this being in my ass, I mean pussy, was frightening.

Jim played with my ears saying, “Nice earrings Jill. Now make love to my
cock. Close your eyes and suck me off because you want my cum. Oh, and
don’t pretend because I know the difference between a girl who loves cock
and a faker.”

Well I was pretty stoned so I closed my eyes and started to suck his
cock. I thought about a Popsicle but his dick wasn’t cold. I thought about
a bratwurst (it was thicker then a frankfurter) but no one sucks a

And then something happened. I felt his cock throb. It was a completely
different feeling. It was alive and in my mouth. My mind wandered for a
moment in a trippy sort of way but when his fingers ran through my hair the
reality came back. I was sucking a man’s cock. I had done this already
earlier today, several times. But unlike earlier this was gentler. I didn’t
mind it. Was I becoming a girl? His cock grew larger in my mouth and I was
expecting him to cum but instead he pulled up with his hands stopping
me. When his cock came out of my mouth he held the joint to my lips. I

His voice fell from above with the words, “You are going to stand up, dance
sexy for my cock and slowly remove your panties. Then you’ll use some lube
and fuck my cock. I want you to learn how much your pussy desires cock.

All cock. Every action from you will be a demur bitch in heat. That’s all
you will think about tonight.”

He raised me up slowly saying, “you will play with your pussy when you fuck
me and have a good clitoral orgasm at the same time my sperm is swimming up
inside you.”

Someone had put on Suzanne Vega “As Girls Go,” I took another hit and
started dancing. My maleness was fading away as I wooed the boys with my
moves. But most I was teasing Jim. Grinding into him. Rubbing his cock with
my panties. Where the music had come from I don’t know but if you heard the
lyrics, “You make a real good girl as girls go. Still kind of look like a
guy I never wondered why. What happened to you to make you more girl then
girls are”

“Go ahead girl. Wiggle that ass.

Jill if you are going to make it through the next two weeks as a girl you
need to use your girl brain. You know how girls wiggle their butts and then
use their thumbs to pull their panties down don’t you,” Jim said as I

When you’re in the deep end of the pool you can only swim so I answered,
“Yes Sir,” and continued dancing.

“You’re in store for plenty of cock over these two weeks Jill. All of us
have friends whom you’ll meet and fuck,” Jim continued.

Another hit on the joint and I was so high my mind twirled as I spun like a
girl and wiggled my ass bending over like I had seen girls do in porn


It wasn’t too hard a whack but it did sting.

“Girls like you enjoy having their ass spanked a bit. Right?” Jim

I didn’t know if it was a rhetorical question or not but I didn’t want to
take a chance so I squeaked out a “Yes Sir.”

The other guys were remarking Jim on his training methods. I bent over
again wiggling my ass as instructed.


It was the other cheek. I don’t think it’s what Jesus had in mind.

“A little slap here and there should make your ass tingle and your pussy
wet for dick Sissy. Right?” Jim asked.

“Yes Sir,” I answered.

This went on for another 10 minutes while Jim would either slap my ass or
feel my ass. I couldn’t figure out why girls liked to be spanked. For me
the humiliation didn’t feel very sexy. However being stoned I was really
feeling girlie as I danced and even more when I was bent over lowering my
panties. I guess even Jim noticed because fondled my ass and I felt his
cock touch my ass.

I lowered my panties a bit more and felt Jim’s finger go to my crack. I
wanted to pull away but at the same time Jim said for me to do the
opposite. A moment later he had me palming my ‘clit.’ The odd part about
all this, and perhaps because I was stoned, was my little penis started to
get hard. I thought it was from the satin panties but in between my stoned
thoughts I realized the panties had a cotton crotch so it couldn’t be that.

Jim’s fingered rubbed down further and as I rubbed I lowered my panties
more still rubbing either on Jim’s finger or cock. He was using both and
also giving me hits every now and then. I couldn’t remember how many. It
was like all the time but of course it wasn’t. Also Jim was treating me
differently. He was rubbing my neck, lightly pinching my ears, stroking
through my hair. All the things a guy would do with a girl. His hand
touched my thigh once and it was electric. I also could feel his size
versus mine. I was drifting into being a girl for him. It was so much
better then earlier in the day.

And I was most surprised when he leaned down and said for me to keep
wiggling because he was going to get some lube since I might be a bit
dry. The kindness made me want to be more feminine.

I knew my ass was facing the other guys but they had another baseball game
on. It was a night game. Pizza and beer aroma filled the air. I was still a
bit hungry. Jim returned and had me only pull my panties down enough to
“expose my pussy” for him. I felt this cool lubricant and his finger
rubbing my ass.

“This is ‘Glide’ Jim said in whisper leaning over to my ear. “All girls get
dry so I’ve brought a bottle as a gift for you.”

A ‘gift’ for me. Thoughtful.

Then I felt his finger enter my, oh well stoned and Jim, my pussy. He began
to fingerbang me and slowly added another finger and another stretching me
until finally his cockhead touches my hole.

“Now girl fuck me,” Jim said.

Well he didn’t have to say anymore. I slid my ass back gently feeling him
entering me. He gave me another hit and his cock went deeper.

“Like a good ponygirl Jill you will ride my cock and when I feel you need
to ride a bit faster I’ll spank your ass,” Jim said as his dick finally
reached so far in I thought he was in my tummy.

So here I was riding a cock like a girl.

Fucking him. And every now and then when I slowed down he’d spank my ass
and I’d speed up.

“Good little sissy,” he’d coax me.

“Rub your pussy on my cock,”

he’d state.

The whole time he didn’t move. He just was standing there while I did the
work. I was fucking him. I wanted his jism he’d say to me. And then just as
he was about to cum he cracked something and put it under my nose telling
me to inhale. My heart started racing. I wasn’t sure of anything other then
Jim’s cock deep inside me and the warm wetness his cock was oozing into
me. Oh and me pushing hard back onto his balls as he came.

But something else happened at the same time. My hand had been rubbing my
nub during the whole process. I didn’t even realize it until I felt wetness
in my palm. Amazed and sort of to myself but I was so stoned I said it out
loud, “I came.”

“Good girl,” Jim said.

His cock still in me he grabbed my hips and held me tight to his cock
whispering again in my ear as his dick began to soften, “Now I understand
you’re the type of girl who enjoys her hole filled with piss. Is that

Shamefully I answered, “Yes Sir.”

And just as I was finishing the word he began to pee in me. It was a warm
full flow mixing with his sperm. Jim gave me a final toke as he peed in
me. I was so relaxed I his flow felt like it was going to some deep dark
region in me. He peed and peed. More then any of the guys earlier. I didn’t
have a plug.

Jim’s final whispers in my ear were, “You are a good girl Sissy. Now when I
pull out I want you to pull up your panties and walk over to the other
men. Proudly tell them how much you enjoyed my cum and piss. Ask Joe when
you are given permission to empty yourself you would like to go in your
glass since you want to drink it down. Don’t forget to animate ‘proudly’
when you go over to the men. Jiggle. Wiggle.

He pulled back out a bit. He mushroom head still in me and then he peed a
bit more.

“Squeeze tight now honey and hold it all in. Don’t leak any.”

As his cock head pulled out I was squeezing down both ashamed and sated. I
pulled up my panties sticky with my cum now washing against my balls. I had
never had a better orgasm in my life. I could tell from the amount of sperm
in my panties it had been my biggest load ever. It coated my clit too.

And so the next part of the evening began as I walked the short distance
over to the men who had been watching.

“I told you she was a she-slut,” Joe snarked.

Larry saw my eyes looking at his tented khakis. “Yes girl, I have a load in
my balls for you,” Larry said. I’m not the lover Jim is. I like it rough
and degrading and I think you like it anyway you can get it. Am I right?”

My heart sank as I remembered there were eight men in the room, nine cocks,
and how many sexual permutations impossible to discern.

“Yes Sir,” I answered in my stoned sissy voice.

Now my sissy voice was definitely an octave higher then anyone here but at
the same time it didn’t have the tone of a real girl. The only similarity
was ending the last syllable on an up note.

“Well why don’t you start answering with more then just a “yes sir.”
Instead repeat a bit of what is asked of you,”

Larry said. “Go on.”

I tried to think what he meant. My head was swimming from the pot and
poppers but I struggled out in sissy, “Mister Larry, I like it anyway I can
get it, Sir” The `Sir’ at the end of the sentence just slipped out having
heard a girl in my class once talk to a teacher that way.

“That’s a great idea Larry,” Sean said.

Joe agreed and then they all did. I had a new directive. Answering with
Mister whomever and ending on Sir with some thoughts in between.

“So tell us about sex with Jim,” Tiny asked? “And elaborate.”

What could I say, “Mister Tiny, Mister Jim taught me girls like me enjoy
being spanked while fucking a cock. Mister Jim also taught me sissy nubs
could get excited. Mister Jim (I figured I’d better not use he) taught me
how to love a cock in my pussy Sir.”

“Hey Jimmy, when you wife left you a few months ago didn’t she leave her
wardrobe?” Unc asked.

“She sure did and I think pussy girl here is about the same size as she
was. She had tiny tits too. Double AA. I think sissy here maybe bigger up
there,” Jim said.

“How about we go over their guys? There’s more room and bit more
secluded. Plus we won’t have to worry about any neighbors’ accidently
showing up. Isn’t that a great idea Sissy?”

More then a little worried I started to say “Yes Sir” when someone slapped
my ass.

“Mister Unc, I,”


“You are not an I,” Paul said. “You are a `sissy girl.”

Besides the fear of the floater nine fairly mean looking guys surrounded
me. Outnumbered and outgunned I replied, “Mist Unc, sissy girl would love
to go to Mister Jimmy’s house, Sir.”

“Then it’s settled,” a chorus echoed.

I wasn’t even asked to clean up just to make sure everything was back in
order. So I checked all the rooms. Put the towels in the dryer and met them
back in the living room. They had cleaned up everything.

“Sissy girl wiggle your sexy butt out to Jim’s car. He has it all warmed
up,” Joe said.

So in high heels, white panties, pink nails, tit bars and chains, lot of
tattoos and earrings I headed out to Jim’s car. The men followed. There
were three car loads of men as we left my home. I was sitting in the back
seat middle between Joe and Sean with Jim driving. Unc and Tiny were in
another car and the rest of the guys in a big SUV.

As we started to drive away Joe turned to me, “Look what I brought,” he
said showing me the glass. “Didn’t want our girl forgetting her Jim
cocktail. It was then I remembered the cocktail that was gurgling up inside

(part 5 to follow)

Date: Sun, 29 May 2011 03:19:15 -0700 (PDT)
From: lauren westley
Subject: High School Dilemma Part 5 by Lauren Westley TG

(Authoress’s note: of course all disclaimers are still in place regarding
SCENES AND EXTREME HUMILIATION. This is only a fantasy story XXX+. I only
wish there is enough here to make each of you happy. To those who have
given me constructive criticisms as well as those with praise
thanks. Lauren Westley. (fundipity@yahoo.com)

High School Dilemma

Part Five

By Lauren Westley

As the car bounced around on old shocks I felt Jim’s deposits swirl inside
me. I actually had a weed induced thought of whether it would look like a
smoothie when it came out. I know, how disgusting of me to think that. but
Jim’s kind way of having sex with me made the thought of drinking it less
then horrible and then my mind tried to make it into something acceptable.

Thinking back to barely a week ago when I kissed Kelly, Joe’s
girlfriend. We were eye to eye. Me 5’5″ and Kelly 5’5″. I may have even
weighed less then her. I had overheard her once in the hallway saying she
weighted 120 and girls don’t make up stories about weighting more then the
do. Instead it’s the opposite. I was more like 117 but I wanted to be
bigger so I told everyone 120 when they asked. I wanted to be taller too so
I tried to say I was 5″ 6 ¼” but I was barely 5’5″.

I hadn’t ever had sex with a girl. Actually only one girl had ever seen my
penis and she had laughed so hard I ran out embarrassed. My penis was the
size of my little finger. At least it wasn’t the smallest penis in the
world. I had once checked and the smallest penis was 5/8″ mine was a good 1
3/8 inches when erect. I guess when it wasn’t it was probably 5/8″ or
less. It was embarrassing only to me since the incident with that girl
until earlier today when Joe and Sean laughed.

Now I’m sitting between Joe who is 200 lbs of muscle with plenty of dark
body hair and scraggly black hair on his head and his brother Sean who
isn’t much smaller who sported red body hair, a freckled face and a marine
boot camp red hairstyle I wondered about their lineage. Trying not to think
of the circumstances I’m in I imagined they had an Irish mother and
different fathers. I even wondered, since Sean was the youngest, did their
Mom take a trip to Italy, get pregnant, come home and birth Joe finally
settling down with a nice Irish lad in her neighborhood?

Of course all I’m wearing are my sister’s white panties stained with my cum
drying against my `nub’ and her open toed high heels. My pink nails
contrast the femininity of my smooth, hairless white skin. The blond curls
on my head make feel girly after the way Jim pulled his masculine fingers
through them as I fucked him. Though I can’t see my curl hair right now I
do know how they look. Other then that my body is girly smooth moisturized
by various creams including man-cream. But it’s the tit bars and chain that
hang between them that make me a slut bitch. And the thought of all those
disgusting tattoos horrify me.

I take the ride as an opportunity to raise my hand hoping this way I can
ask a question.

Sean puts his hand on my thigh and says, “I like that sissy girl. You
should raise your hand whenever you want to talk. We may or may not ignore
you. But this time what is your question?”

“Mister Sean, will these tattoos come off Sir?”

“Well Jill if you are a good girl they will fade over the week. They should
be gone in ten days but if you aren’t then we’ll just have to make them

“Mister Sean I promise I’ll be a good girl Sir.”

“Jill, a good girl will do as she is told,” Sean finishes.

In my mind I realize there isn’t really any choice and I’ll know in ten
days if Sean is telling the truth. Also they did seem a little lighter
earlier. Or was that just my imagination. We enter a highway and I wonder
where Jimmy’s house is. And I also wonder what Unc is going to want from
me. He’s so big and fat and not my type. MY TYPE. What am I thinking?

Sean’s hand moves up my thigh and I can’t believe my clitty starts to have
feelings. I hope it doesn’t show. I try to concentrate on something
else. Look at the signs I say to myself. When I look up I see we are about
to exit the highway. The highway exit sign says Pearl Rd. This is where
trailer parks and shanties are located. It’s about 20 miles from my house
and I’ve never been here since everyone in my neighborhood knows it’s the
rough and dangerous part of the city.

We are now driving on dark streets and Sean is still fingering my thigh
near my crotch when we stop. I see the stop sign through the front
window. There’s a street to the left. The only illumination seems to come
from our headlights. I can see decaying old brick buildings and some trash
littering the streets. On Joe’s side there appears to be one of those
alleys where you pick up the trash behind buildings.

Sean looks at Joe and as if they had spoken to each other Joe looks at me
and says, “Sissy would you like to be allowed to empty yourself without
drinking it and no more piss tonight?”

I can’t believe what I just heard. I’m ecstatic as I reply, “Yes Mister Joe
Sir. Yes.”

“Well Sissy this is what you’ll have to do. Down the alley there lives an
old bum who has been there for years. You have to go up to him and convince
him to let you give him a blowjob. Then you must get him to cum in your
mouth. Either during or after he cums in your mouth you can pee out what’s
in your pussy and come back here. Show us his cum in your mouth and finally
swallow it.”

My mind is considering the exchange. Not sure which is worse but not having
any more pee in me is the better idea.

“This offer ends in five seconds,” Joe said.

Within two seconds I mumble out the words, “Yes.”

I don’t get reprimanded for not saying it the right way and Joe opens the
door. Joe makes me climb over him and my eyes lock on the glass he’s
holding in his hand. No way I’m not coming back with a mouthful of cum, I
think. Fortunately it’s a warm late spring night. Cautiously I look around.

“Hurry up girl,” Jimmy says, “we don’t have all night.”

I strike out down the alley and you know what I’m wearing. What I must look
like! My heels click on the concrete. It’s very dark. I can’t see anyone
and I begin to wonder if this is just another humiliating joke.

“Mister,” I call out weakly not sure if I want him to be here or not. Not
even sure I want him to hear me. My voice is a bit squeaky. I’m getting
use to being in this sissy octave range.

I hear some rumbling by the garbage near me and then a hand comes out and
grabs my ankle. Scared I nearly pee myself.

“Whatcha want girl?” comes from a gravely bass voice as the papers move
away and lying there slowly getting up is an old black man.

“Mister would you like a blowjob,” I blurt out.

Now his eyes have adjusted, better then mine.

“You no girl are yu?” he says obviously looking at my flat chest.

“No Sir.”

“Are u one of those kin-kee puss-boys?”

“Yes Sir.”

“An u wan to wrap your lips on my banger?”

“Yes Sir”

Well it didn’t take long for him to agree. Next to him he lights one of
those small electric camping lights. He maneuvers himself with his back
against the dumpster and pulled me by the leg reaching up and grabbing my
wrist and pulling me down.

“I got full nuts,” he said as I went down.

Instead of having me kneel on the cement he had pulled out an old rag and
placed it for my knees but as I came down near him I could smell the

“U make a cute puss-boy,” he says, the dim light illuminating my
face. “Give here Mr. Sam a kiss fore yu git sum my hon-eee.”

He pulls me close by my cheeks to his lips and the dim light shows how big
they are just before his lips smother mine. I am shocked as he pushes his
tongue into my mouth and licks my tongue washing his taste all over my
mouth. His saliva drools into my mouth and then he pulls back pushing my
head down between his wide spread legs. Taking one hand off my head he
unzips his fly and his dick pops out. No underwear.

“Now git yourself some nut-juice puss-boy,” he coughs out.

As horrible as this sounds part of me felt if anyone deserved a blowjob
Mr. Sam did. So I got to work thinking I was probably doing a good deed. I
tried to breathe as much as I could through my mouth but often I had to
inhale the stench around me. His cock wasn’t too big and since I couldn’t
really see it I tried to imagine it was one of those Tootsie-Roll
pops. Also he didn’t hold me but instead leaned back and would say things
like, `nice lips puss-boy,” none of which were said meanly. I’m not sure
how long I was sucking his dick when I felt his legs extend a little bit
and he seemed to lean back harder against the dumpster. With just a moan he
began pumping my mouth full of his jism. And here’s another thing. His jism
didn’t taste bad. It washed over the foul saliva from his earlier kiss
coating my tongue. Mr. Sam’s load was bigger then any I had had earlier. My
mouth was full. I had accomplished my task. No pee for the rest of night.

“Show me puss-boy,” as Mr. Sam’s hands lifted my head up. “Open dat puss.”

He held my face as I opened my mouth. It was full of his man juice.

“Good puss-boy,” he said. “Now swallow my nut-juice.”

Swallow! I couldn’t believe it. I didn’t want to go back to the car with an
empty mouth but Mr. Sam did something that made me swallow his nut-juice
into my belly. With one hand he held my mouth closed and the other he
pinched my nostrils till I swallowed it all. Then he let go of me.

“You come back puss-boy, anytime,” Mr. Sam said as I got up.

I walked back to the car with a hobo’s nut-juice in my belly instead of in
my mouth with my high heels clicking away in the dead of the night. The car
headlights glowed ahead like a lantern to hell. I wondered how could I feel
sorry for a bum and then even like the taste of his cum. I wanted to
cry. Even the thought of crying was humiliating but the tears came and
flowed down on my cheeks as I reached the car.

“Why are you crying,” Joe asked as he opened the door and looked up at me.

“Mister Joe, the hobo did cum in my mouth but he made me swallow it,” I

“Is that why you are crying,” Joe mocked.

“Mister Joe, that and also how humiliated I feel.”

I climbed into the car sitting between Sean and Joe. I had been so upset I
had forgotten about letting Jim’s cum and piss cocktail out. They asked me
to tell them about my `adventure’ as they called it. I told them everything
about how he called me `puss-boy’, about `nut-juice,” etc. as Jim continued
driving. There were comments about how bad I smelled and laughter about the
rag on the ground for my knees.

“Well you were a pretty good girl Sissy,” Joe said, “but you really didn’t
accomplish your task. We’ll have to see later what a proper response will
be. BTW, did you get to let your pussy pee?”

Stunned, I had forgotten all about that when the shock of having to swallow
wiped my mind clear. Jim’s piss and cum were still deep inside me. I guess
because I carried three loads for such a long time Jim’s hadn’t made the
necessary demand on my system.

“Mister Joe I did not get to pee. I forgot Sir,” I answered.

Not a word was spoken as we drove on through the dark streets. Although the
main street was called Pearl the district was known as the black pearl. Not
because of rarity but because of the darkness of life here.

I smelled some pot wafting back from the front seat and a few moments later
Joe was holding the joint to my lips. I inhaled and the high kicked in
again. I flashed back to my house when I fucked Jim’s cock. How he came in
my pussy and my own orgasm. As repulsed as I was it was equally
exciting. More exciting then any sexual experience I had ever had.

We pulled into a driveway. I was thankful it wasn’t a trailer home. However
with the old rusty car on the front lawn I wasn’t expecting much.

“We’re home,” Jimmy said.

There were no other cars in the driveway as we walked from our car to the
back porch. The back porch had two, sorely in need of repair, steps with an
old zinc coated dented garbage can next to them. The porch itself was very
small with one of those funny little dormers over the door. You know they
look like a tiny roof with shingles. A small café table and one chair used
the space not needed by the door opening and to walk down the steps. The
white painted metal door was dented. I could only imagine the quarrel that
must have taken place here. How dangerous was Jimmy. I had gone along with
this since I didn’t want to be hurt and had continued out of both
embarrassment coupled with all the men who could have simply raped me. But
I hadn’t thought of how violent things might have been. Now I did. I
cowered even more as we walked in and I saw a couple of holes punched into
the sheetrock. I decided fulfilling their demands would be the best course
of action and if the tattoos didn’t fade away in 10 days I would run away
and never go home.

Walking through the house I noticed how nice this home must have been at
one time but certainly hadn’t had a woman’s touch in awhile. Although the
kitchen was fairly clean empty bottles and a few plates stuck with food sat
on the counter. The cabinets were made of cheap pine. They were pre Home
Depot probably the original cabinets in a 1960 tract home.

Some of the walls had blank areas where pictures must have hung at one
time. Before I saw more of the downstairs Jimmy took the lead and said for
me to follow him to my quarters. As we walked upstairs he told me he had
moved all his ex’s stuff out of his room into what had once been his
daughter’s room. He said his daughter had died when her School bus had
skidded over the side of the road, flipped over and over and crashed
killing several including Sarah in the worst fatal School bus accident in
the State. It had been the blow that ended his marriage. He was a bit
melancholy about it as he talked and I actually felt sorry for him.

The room was decorated for a seven-year-old girl except a few things were
different. There were some boxes marked Alana, his wife’s name and the
closet had Alana’s clothes hanging. One box was marked lingerie and another
blouses. There was only one small chest of drawers and a multi-tier of
empty shelves. A vanity sat between the two windows. The wallpaper was
Disney Little Mermaid, Sleeping Beauty, Cinderella and the single bed had
been painted pink with pink and white striped sheets.

When we went downstairs again I was in for a big surprise. There was just
Joe, Sean, Jim and Jimmy. Sean called me over.

“Sissy we have decided the following as your punishment and what you will
do. For your punishment each of us will give you ten whacks on your ass and
as you know there’s no screaming here either. Then if you haven’t leaked
your precious cargo you may go upstairs and go to bed exactly the way you
are dressed now. Finally if you wake up tomorrow morning and you haven’t
had an accident you may use the toilet. Then shower and find something
appropriate to wear. You’ll make breakfast for Jimmy and have it ready for
him by 7:30am. Instructions for your day will follow.”

I was going to be free of this nightmare for the night. Then I remembered
school had ended on a Thursday so tomorrow was Friday that meant these guys
probably had to work but worse it also meant the weekend was around the

“Do you think you can handle that Jill,” Sean asked?

Almost in girlie glee with a little up and down movement clapping my hands
as if I was now a trained seal I answered, “Yes I can Mister Sean. Yes I
can Sir.”

I took my spanking fairly well. I was crying through the last half but I
didn’t scream and I didn’t leak. Finally sent to my room with my sore ass
full of piss and cum I lay down on the bed squeezing my sphincter and fell
asleep crying.

6 Responses to “High School Dilemma Parts 3 4 5”

  1. Lauren Westley Says:

    thanks so much for posting my stories…I really appreciate it. Hugs Lauren Westley

    • riana987 Says:

      Thanks for writing them! I’m a huge fan of your stories – will post more of your old ones soon and look forward to your new ones!

  2. sissygirl Says:

    love your sissy site, being a femme girklyboi I really like how you have captured these men taking care of their sissies


  3. Thank you so much for taking the time to write such kind words. You put a smile on my face

  4. lee Says:

    now i have to wipe the screen, AGAIN, because of you:-)

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