High School Dilemma

February 22, 2011

“Spread you legs and hold them open and close your eyes. If you move I’ll give you a spanking so hard you won’t be able to sit in school tomorrow and everyone will know,” Joe taunted.

So, I sat with my legs spread apart as he towered over me. “Remember, don’t move,” he warned. And then he unzipped his fly, pulled out his cock (I didn’t see it, but I sensed it), and before I realized it he was peeing on my jeans right between my legs. Soaking my jeans and underwear and I could feel my balls warm with his pee as he loudly said, ” I claim you for my property and thus mark you with my piss as proof forever.”

As I started to move away from his pee he leaned over and slapped my face and said, “don’t.” So, there I was sitting splayed and letting him empty his bladder on balls. I was so humiliated. When he finished he shook his cock and some pee droplets flickered on my nose and eye. He laughed.

Looking down at me as he zipped his fly he continued with the following. “As you punishment for the next week you will get a pair of panties from your sister. They had better be satin. You will wear them everyday this week. If you don’t wear them I will spank your ass red. Do you understand?”


Date: Fri, 26 Jan 2001 22:22:28 -0500
From: fundipity
Subject: High School Dilemma Part One (TG) by Lauren Westley

High School Dilemma

Part One

By Lauren Westley

I should have known better. It was such a stupid thing and it
didn’t even work out. Here I was graduating from High School. I had just
turned eighteen and it was the last week of school. How could I have done
it? Why did I take the chance? Kelly was probably the prettiest girl in
school. Her hair was long and blond. Not much different then mine. Actually
we were both about 5′ 5″ and weighed around 120 pounds. But, Kelly was
Joe’s girlfriend. At least she had been for the last two years until the
school Prom a week ago.

Joe on the other hand was huge. He was nineteen and had been
the star defensive end of the school football team. Well over six feet tall
and weighing somewhere north of 200 pounds with a mean streak he was
someone to avoid at all cost. Stories abounded about how he had beaten the
shit out of some kid who had gotten in his way. Or had gotten into a brawl
during the weekend. His older brother Sean had been the meanest kid the
school had ever known. He had graduated three years ago. Someone had said
he was at least twenty when the school sent him on his way. Apparently he
had been in a correctional facility since then for a melee at a local
bar. Why Kelly went out with Joe was beyond everyone. But as she had said
at the prom Joe just wouldn’t let her leave.

Anyhow, at the school prom last week we had all had a bit to
drink and was having a great time. Over the years every guy had fantasized
about Kelly and at the dance she was the knockout of all time. She wore a
beautiful green sequin dress with a matching headband. They accentuated her
hazel eyes. Similar to mine except mine were a bit greener. Soft white skin
and red lips just beckoned to be kissed. There she was standing by herself
near the punch bowl when the liquor convinced me to go over and talk with
her. Me with no muscle tone and white skin, the class poet and by luck had
avoided being the class wimp by going home right after school had walked
over and said, “Hi Kelly.” She had had a few drinks also and was very
friendly. Before much time had elapsed Kelly and I were back in a school
hallway and had started kissing. I still don’t know why she had kissed
me. It had seemed to unfold so naturally and her lips were warm and tongue
sweet to the taste.

But suddenly, there was Joe. He was red and furious. Kelly
turned to him and told him to be still and that she was no longer his
girlfriend and that she preferred me. I stood dumbfounded and scared but
Joe just yelled at Kelly and stared ferociously at me and then left us. I
took Kelly home that night and we kissed some more at her house and held
hands. The next day at school Kelly avoided me all day and when we finally
met up she said I just wasn’t her type and asked it we could “just be

Well, I didn’t like the outcome, but what could I do. I asked her whether
she was going back with Joe. She said “no way. I’m glad this happened. Now
I’m rid of him and can have a fun summer and be free at college next year.”
I looked at Kelly so pretty in her pink sweater and gray skirt and thought
to myself at least I had had a moment with her.

That was last week and all through that week Joe would scowl at me every
time he saw me. I wasn’t much worried since we lived in different sections
of town and Joe was so caught up in sports that he had practice everyday
for something after school. So I left at the bell and went home. There was
only one week to go and then summer. We would never meet again. At least
that was what I thought until yesterday afternoon. The last Monday of the
last week of High School was yesterday and now things had changed.

I had left school just after bell. Wearing jeans and sneakers I walked the
trail through the woods to my home. I had been doing it for as long as I
could remember. The woods were about hundred acres of underbrush, trails
and huge oak trees that separated the school from the north side of
town. It was on the north side that the socio-economically well off
lived. Joe and his brother lived south of the school in a project. I had
never even been to that part of town. Apparently there were empty
dilapidated buildings and trouble. Not a place I would ever travel to.

So, there I was about halfway into the woods when all of sudden I felt
someone knock me down and start punching me. He punched my face, my stomach
and before long I was crying. When I looked up I saw Joe. He looked down at
me and with spit shooting from my mouth he yelled at me for breaking up his
relationship with Kelly. I sat up and he yelled at me that I’d better not
get up, unless I wanted to really get my “ass kicked in.” So I sat there on
the ground in the woods as he continued his tirade. I saw him looking at me
and then he called me a sissy girl because I was crying. I was about to get
up and try not being a sissy when he punched me again. He said that I had a
choice. I could be the sissy he knew I was and not show any macho
stuff. Then he said if I acted like a sissy, he wouldn’t punch me but
instead would slap me like he would a girl. Or else, I should get up and he
would beat me silly.

I was in such pain and no match for him I just sat there simpering. He
laughed a little and then called me Jill. My real name is Bill. He taunted
me calling me JILL, JILL, JILL. I sat there thinking I’d rather be thought
a sissy than being punched silly. Let him have his moment I thought. School
would be out soon. It would all be over. Then he smiled and told me if I
didn’t do exactly what he said right now he would beat “the shit out of me
everyday this week.” So I sat there.

“Spread you legs and hold them open and close your eyes. If you move I’ll
give you a spanking so hard you won’t be able to sit in school tomorrow and
everyone will know,” Joe taunted.

So, I sat with my legs spread apart as he towered over me. “Remember, don’t
move,” he warned. And then he unzipped his fly, pulled out his cock (I
didn’t see it, but I sensed it), and before I realized it he was peeing on
my jeans right between my legs. Soaking my jeans and underwear and I could
feel my balls warm with his pee as he loudly said, ” I claim you for my
property and thus mark you with my piss as proof forever.”

As I started to move away from his pee he leaned over and slapped my face
and said, “don’t.” So, there I was sitting splayed and letting him empty
his bladder on balls. I was so humiliated. When he finished he shook his
cock and some pee droplets flickered on my nose and eye. He laughed.

Looking down at me as he zipped his fly he continued with the
following. “As you punishment for the next week you will get a pair of
panties from your sister. They had better be satin. You will wear them
everyday this week. If you don’t wear them I will spank your ass red. Do
you understand?”

In a squeaky voice I answered yes.

He seemed pleased with himself and looked down at the dark pee stained
crotch, laughed and then left me there. After I was sure he was gone I got
up. He urine smelled so strong. As I ran home ashamed, holding my hand over
my pee soaked genitals, the earlier warmth of his pee turned cold. I
managed to get home and upstairs to my room without anyone seeing me. But I
had to wash his deep yellow urine out of my white jockeys and also my
jeans. I could smell that odor all night even when it was gone. So fearful
of him was I that I managed to get a pair of white satin panties from my
sister Jane. Jane was two years older then me but we were about the same

I put the panties on the next morning and went down to breakfast. I was so
nervous. I thought everyone could tell. I was thankful that Jane was gone
for the next 8 weeks. She was a counselor at a camp in North Carolina and
had gone there a week early to set up for all the kids that would come next
week. She loved being a counselor at camp but she was also very
feminine. During the rest of the year she dressed very hot. When I got the
panties from her dresser I was amazed that they were the only white
pair. She had all sorts of things like thongs etc.

Mom and Dad were sitting at the breakfast table when I came down. Dad
started the talk. “Bill, next weekend Mom and I are going to go on a two
week business/ vacation. I just talked you Mom into going. I convinced her
you can take care of yourself and will be responsible. We are going to be
on a sailing cruise in the Caribbean and will call you when we have a
chance in port. Since this is a real outback sort of adventure we don’t
know when we’ll reach you so be sure to change the message on the answer
machine each day. That way we will know you’re ok.”

Mom smiled at me and asked whether I’d be ok. I forgot about wearing the
panties and told them to have a great time and that I would be fine. Mom
also told me she had called the Mr. Weingold who ran the local grocery
store and had advised him that I would be alone and that I could charge
what I needed at the grocery store. “Also, Sid (Mr. Weingold) said he would
check in on you at some time next week. He’s going fishing for a few days
and will call or stop by when he gets back,” Mom said.

Mr. Weingold was a fat slob I thought to myself. I had never been nice to
him, but my parents thought he was a nice man. Dad sometimes mused as to
why at 48 he had never married. I knew why. Who would marry a 250-pound fat
slob who was unkempt and dirty?

I assured them everything would be fine and went to school.

So, here I was sitting in class with satin panties over my ass and Joe
keeping an eye on me. However the day went by without incident until I went
to my locker at the end of the day. There was a note inside. I opened
it. All it said was I had gotten by the first day and could go home
safe. But in order to be safe the next day I would have to wear the panties
and shave all the hair off my body. If I left any hair except for a proper
little patch I would be beaten tomorrow. There was a cut out of a girl who
was shaved except for a patch over her pussy. In deep blue ink written on
the top right of the picture with a pointing arrow were the two words, LIKE

At home that night I thought to myself it was a lot better to do what Joe
wanted then to get beaten. Also, he hadn’t even bothered me. Perhaps I
would get through the week ok. So, I shaved my body that night and made the
little patch above my dick. As I did so I wondered how big my dick was
compared to Joe’s. I hadn’t seen his as he peed. I had my eyes closed. Mine
was a good four inches when hard and not very thick either. I hadn’t seen
anyone else’s since freshman year. I had finished my required PE that year
and had avoided all things that would require group showers. I thought, I
bet he’s smaller then me. They always say big guys have small dicks. And
that made me feel better as I drained the tub and dried off.

The next morning at breakfast my parents told me they would put everything
I needed on the refrigerator and in the drawer next to it. They would be
leaving Saturday morning early so they could fly to Florida and catch their
ship. Dad was really excited about getting away. Again I assured mom
everything would be ok and went to school wearing the panties and fully
shaved. I wore a long sleeve shirt and kept it buttoned up. Joe looked at
me and smiled. But again the day went without incident except when I got to
my locker. Again there was note. This time I was to find a pair of my
sister’s pantyhose and wear them on Wednesday with the panties underneath.

Well, none of this bothered me much since I wasn’t getting beaten and no
one knew what was happening. It was easy to comply. The next day I sat in
class shaved, pantied and panty hosed. The silken panties made me squirm
sometimes and I would nearly get hard but nothing I couldn’t
handle. Another note said for me to take a nice bath with my sister’s bath
bubble and wear a piece of scotch tape on both my nipples.

I got through Thursday and thought only one day left. School would be out
and this would be all over. What I thought was the last note came in with a
little box. It said I was to open the box that night and wear everything
plus what was in the box for Friday. If I did this, there would be only one
last thing and I would get that in my locker when I cleaned in out Friday.

That night at home I opened the small box and saw a butt plug in it. I was
shocked. A little note said “PUT IT IN NOW!” I had made it through the
week. This was so humiliating but only one more day I thought as I pushed
it up my ass and went to bed.

The next morning sitting there at breakfast my parents giving me last
minute instructions I felt my cheeks go red. Mom asked if I was sick. I
said no and hurried out to school feeling the plug move in my ass as I

I sat in class squirming a bit as Joe looked at me and smiled. At the end
of the day I went to my locker and cleared my stuff. There was one more
envelope. It said to be opened as soon as I got home. I hurried home
figuring that it was over and Joe would simply give me a note laughing
about what he had made me done. I rushed upstairs to my room and sat
down. I didn’t even take the plug out because I wanted to read the note

The note said, “Your final act of humiliation will occur tomorrow. You’ve
come through the week so don’t mess up now. At 10am meet me in the same
place we were last week in the woods. Make sure you’re wearing a bra and
perfume and everything else you wore this week. OR ELSE.” I was afraid as I
read this but again I thought I could handle one day even if he peed on me
again. Then I would be safe at home away from Joe forever.

Saturday morning my Mom opened the door to my room and said, “bye Bill, see
you in two weeks. Are you still sick? If you are, call Dr. Jones. The
number is on the refrigerator. Also we’ve left reminders like the changing
of the message each day.” I told her to have a great time, not to worry and
would seem them in two weeks. She left the room. I looked at my clock it
was 7 am.

By 9:30 I was sitting in the kitchen with the plug up my ass. Panties and
panty hose on and a white cotton bra covering my scotch taped
nipples. Twenty minutes later I put the perfume on. Something called
“Opium” and went to meet my fate with Joe. I thought as I walked to the
woods that in an hour I would be home and this would be over. He would
either beat me silly or let me go.

When I got to the site, Joe was there. He said, “hello Jill, everything
ok?” I smiled meekly and nodded yes.

“Okay honey, he said, now just take off what’s covering everything. Tell me
what you’re wearing and fashion show it to me. Tell me about the perfume
etc and what the whole week was like and we’re through. Okay.

I asked him if I had to and he slapped my face hard and demanded, “YES.”

As my face stung, I removed my jeans and shirt and stood there in
everything telling him about the week. When I was finished he told me to
take off the panty hose. As I removed them he told me to make sure that I
turned and bent over so he could feel if I was wearing the butt plug and
that I should make my voice sound as feminine as possible. Since I had sung
soprano in the school choir and my voice had not really gotten deep yet, I
was able to comply.

Standing there in the warm early June sun I turned wearing the bra and
panties with my skin shaved. He rubbed my ass as felt the plug (I felt my
penis stir a bit as he did this. I didn’t know why) and grunted an
affirmation that it was there and then slapped my ass as I stood and turned
facing him again. He asked me what perfume I was wearing and I said in my
most feminine voice, “I am wearing the Opium perfume.”

“It smells very nice and feminine,” he said. “Now show me how you shaved
your crotch and explain what you did.”

I pulled my panties open and showed him the patch of pubic hair that
remained while explaining how I shaved myself. My voice was falsetto and I
could hear how I sounded very girlish. As I stood there with my panties
held open a cool breeze and my nervous soon found my dick harden a bit
more. He smiled and laughed.

He picked up my jeans and shirt and threw them about 10 feet away. “And now
for the final thing. So that you never, ever, try to take a girl from me, I
want you to unzip my fly and jerk me off into your panties.” As I started
to protest, he slapped me again and said that he would take my clothes and
leave me here if I didn’t. He also said I was to talk to him as I jerked
him off asking, better yet, he said, “begging him to cum on my little
clitty.” I was trapped. I was about to say something but he slapped me
again. I thought, it would be over soon if I just do this now. At least I
don’t have to suck him off or anything. I can do this.

As I unzipped his fly he instructed me to hold my panties open and jerk him
off with the other hand. Taking his cock out I realized how wrong I
was. Soft it was at least 5″ long and thick. I couldn’t believe my eyes.

“Quite a beauty isn’t it,” he asked?

I held it in my hand ashamed as it began to grow. I wondered how big it
would be hard. As if he could hear me think, he said, “eight inches and a
handful thick.”

Holding his cock and pulling it I realized he was tall enough that his cock
actually higher then my navel. Jerking him off he smiled as I told him how
“big he was and how I wanted his cum in my panties.”

He felt my ass and played with the plug and petted my hair and head, as he
grew larger and larger until his manhood was tremendous. He started to
grunt and I knew he would cum soon. I looked down just as he shot his
precum up and hit my face. The first load of spunk also shot up to my nose
and dripped down eventually falling into my panties. I pushed his cock down
and jerked the rest of his spunk down into my panties washing my ‘clitty’
with his cum. Actually it covered my little dick and a puddle formed in the
cotton crotch. He moaned a bit more and finished cumming.

I let my panties go and they closed his cum around my balls and he
whispered in my ear to finish by licking the head of his cock clean and
then thank him with a comment and a curtsy.

Since it was just about over, I did what he said and leaned down and licked
the last droplet of cum from his cockhead.

And then I let go, he stepped back a few inches and I curtsied saying,
“thank you Joe for letting me have your cum in my panties.”

I asked if I was finished and he said yes but one last thing would be
perfect. Then he took his hand and rubbed my cum soaked panties against my
balls and told me to mix my cum with his so would we “be united as one in
this ordeal.”

Unbelievably my little cockette hardened and before long I sighed as I shot
my load into his load in my panties filling them with a soggy cum mess.

Sighing, I asked, “Can I go now?” (I was still using the feminine voice.)

The next thing I heard was Joe calling out, “Sean time to come out.”

Sean came out carrying a video camera. Embarrassed I tried to turn but Joe
grabbed my arm and told me to just stand still. Then Sean showed me the
entire event. Nothing that Joe had said was filmed. Only his chest and
below was shown. But everything I did was very visible and culminated with
me shooting in my panties filled with Joe’s cum. I started crying.

Joe put his arm around me and softly said, “Stop crying Jill. You know that
Kelly dumped me last week. There’s no way I could get another girl and the
summer is here. So Sean and I thought you’d make the perfect ‘Summer Girl’
until someone comes around. You see, I like to cum three or four times a
day. Kelly use to handle that for me and now you can.

He picked up my clothes and told me to put them on and they would walk me
home. I said it was okay I could go home by myself. He slapped me and said,
“Do you want a spanking? Just remember to say yes to my questions and act
like a good girl and everything will be fine. Otherwise I will publish this
flick on the Internet and email it to the whole school and send a copy to
your college. So, put on your clothes and we will walk you home. I want to
know exactly where you live so I can pick you up when I need you.”

So, I put on my jeans and shirt and walked with them. The cum squished
inside my panties as I walked and Joe made sure I kept talking (very girly
like) about how it felt and how much I liked it and how I looked forward to
his three or four loads a day. Sean just laughed as we walked through the
woods to my house. They were amazed as they came to my house. We were on
six acres of land. You couldn’t even see our neighbors. The lot next to
ours was empty and the next lot was still under construction. The other
side of the house backed up against the woods and wetlands. “Fuck,” Sean
said, “this is much better then where we live. So this is how the rich

When we got to the kitchen door, I was saying goodbye when Sean said he had
to, “take a leak.” I let him in forgetting about my parents and everything
and showed him the bathroom. As I did so, Joe stood in the kitchen
waiting. I walked back into the kitchen and saw Joe reading the note on the
refrigerator. I turned ashen white as he said, “Alone for two
weeks. Hmmmm.” Just as I started to protest Sean came back into the kitchen
and Joe explained the note to him.

“Take your jeans and shirt off,” Joe said.

“Please go,” I said forgetting my feminine voice.

“Now you’ll get a spanking as well for answering back and not using the
right voice. NOW TAKE THEM OFF..NOW!” He slapped me so hard a fell against
the refrigerator and landed on the tile floor. The cum oozed as I landed.

“Well,” Sean said, “We are just going to be staying here the next two weeks
so you’d better get use to it or be dead.” His eyes showed the mean fire of
intent. There was nothing I could do about it.

“Now get up and take your jeans and shirt off and lie over my ass for a
spanking,” Joe chimed in.

“You’re going to be our live in girlfriend for the next two weeks,” Sean

Crying I got up and removed my jeans and shirt.

“Oh look Sean, Jill has a puddle of cum that has stained her panties,” Joe
snickered and then slapped his knee for me to lie down for my spanking.

Both my cheeks were stinging hot as I stood there in the cum puddle filled
satin panties and bra my soft white skin exposed and the two big brothers
enjoying themselves. As I walked over to Joe my hips swayed as I moved with
the butt plug and the cum puddle sobbing as I did.

“I like that walk Jill make sure you sway all the time. Make believe your
knees are tied closer than your ankles,” Sean chided. “Gosh, she sure is
pretty Joe. I think this is going to be great.”

I stood in front of Joe as he snickered and tapped his knee and then lay
down in my bra and panties. “I think we’ll just pull the panties down a
little in back so you can enjoy the spanking and the cum at the same time,”
Joe said as he pulled my panties down over my ass but left them on. Then he
began to spank me HARD. Over and over again his hand smacked my ass and I
cried out and then started sobbing uncontrollably.

When he finished he said, “There you are Sissy, now stand up and thank
me. Tell me you’re sorry and will do your girlish best to be pleasant to me
and my brother.”

I got up. My ass was burning from the heat. I knew my goose was cooked. So,
in a quivering little girlish voice I thanked Joe for the spanking and
promised to be the best little sissy girl he had ever met. I would try to
meet all his feminine needs.

“Ok, Jill, that’s enough. Now show Sean and I around this mansion.” We
walked from room to room. Through dining room, living room and then into
the game room that had a pool table and a card table when Sean said it
would be great to have some friends over to play cards and pool. Joe agreed
and said Saturday night was a great night to have friends over and since
this was Saturday he would call some friends to come over later.

“That’s ok with you Jill, isn’t it,” Joe said without expecting a reply. I
asked it I could talk and Joe said Ok. So, trying to be very feminine and
not get another spanking, I said how much trouble I would get in if there
was mess or anything was broken. Joe simply replied that I would be in
charge of cooking, cleaning and cum. “You know all those little girly
things. That will make you a happy sissy. You can do all the housekeeping.”
Sean interjected that I would also do the wash. But that he expected his
shorts to be hand washed and ironed since he was now on the right side of
the tracks. Joe loved that idea and told me to do the same thing.

“Now, show us the rest of the house,” Joe said as he put his arm around my
waist and then lowered his hand to rub my ass as we walked upstairs. I
showed him my parents bedroom and my bedroom, the guest room and finally my
sister Jane’s room. When we entered her room Sean immediately asked, “So
this must be your room?”

I looked aghast but before I could say anything Joe demanded I show him all
my things. Joe opened one drawer that had lots of sexy colorful panties and
bras and asked if they were mine? I meekly replied, “Yes.” Another draw had
stockings and under them there was an electric vibrator. Sean laughed and
wanted to know if I used it at night when I couldn’t get some real COCK. He
reached out and touched my scotch taped nipples and continued. That was the
first time he had touched me and I shivered as I thought about it.

“What’s in here,” he asked as he opened Jane’s large closet. One section
had a whole bunch of slutty clothes. “Yes, these will fit you fine,” Joe
said as he rearranged the closet and told me I should wear what was on the
left side unless told otherwise. Then we went into her, or as they said, my
bathroom. There was a magazine rack with some girl magazines and
Playgirl. Joe looked at it and told me to “be sure only to read such things
from now on.”

Sean came in carrying a pair of red heeled shoes and told me to put them on
and to learn how to walk before tonight. There was a vanity with make-up,
curling iron, rollers etc. On the right was a magazine opened to a page
that showed how you could easily curl your hair. It was a step-by-step
comparison with everything there that was needed. Obviously Jane had
intended to try it out. There was a bottle of L’Oreal hair dye that was
lighter then my own color. Both Sean and Joe smiled and told me that the
first thing I should do when they gave me leave was to do my hair, nails,
and face.

Opening the drawer on the left proved filled with packets of glue on
nails. There were red nails, pink nails, clear, white and others. “I think
pink nails and don’t forget your toenails with matching lipstick should be
good. Oh, and use these.” Sean handed me a box that had a pair of false
eyelashes in it.

Joe and Sean said they would look over the rest of the house. Since it was
before noon, I was to take the next three hours and get myself looking real
good. “Leave the panties on, we’ll tell you when to change them and don’t
sulk. You don’t have time and if you aren’t ready by 3pm I’ll bring my
three Doberman’s over and let them fuck you till you cry. Now, get ready
honey,” he said as they walked out of the room and closed the door.

As much as I just wanted to cry or run away I knew that if I left the house
would be trashed. The pictures would be published. My parents would disown
me. The only thing I could do was what they wanted and hope when my parents
got back I could leave and go away for the rest of the summer: the rest of
my life. With my panties stuck to my, what did Joe say I should call
it. Oh, yes, either my ‘sissy stick’ or my ‘sissy clit.’

They had left the door open and could hear them using the phone. I heard
them call the market and place an order to be delivered. Then Sean was
taking to some friends. I heard 7pm and my address.

“Are you getting ready Sissy,” Joe called up from downstairs? While I
followed the instructions and dyed my hair and then curled it, I didn’t
know that Sean had used the Jeep in the garage and gone home and
returned. Putting on the nails and painting my toe nails I though back to
just a week ago as I sat on the ground and Joe peed on my crotch. I should
have known right then but of course I didn’t. As dumb as I thought Joe was,
it was obvious that his talent lay in sexual domination.

My panties stuck as the rollers did their thing, I pulled them out and then
when I put my hands to my head I could smell his cum. Gosh, he had only cum
one time today so far and I didn’t know what Sean could do. The only thing
I knew was that I was their ‘sissy cunt’ and would be such for the next two

Because of the smell of Joe’s cum I splashed some more perfume over me. It
was nearly 2pm when I removed the curlers and brushed my lightened gold
hair. The whole thing had worked. I looked in the mirror and saw a feminine
outline to my face. Then I put on the eyelashes, some powder and I had
found on the page of the hairdo a bullet telling me to turn to page 32 for
make-up tips with this hairdo. Again, Jane had everything I needed and
since I had been in school plays and was a fairly good artist, I was able
to copy what it said and by 2:30 my face and hair was a feminine as any
girl. I stopped and was admiring my work and didn’t notice Sean standing
there. He smiled when I saw him and said he was pleased that I liked being
their girl. I looked ashamed as I heard him. But then he said for me to
close my eyes and not move. Before I knew what had happened I felt two
punches on my left ear. He told me to be still and then I felt one on my
right ear. He said for me to keep my eyes closed for another minute and
when I was allowed to open them I could see two gold studs in my left ear
and one in my right ear. There was nothing I could do.

“You didn’t know I did piercing did you Jill you lucky girl,” he said. Joe
walked in amazed and walked over to me looking into the mirror from
behind. Our eyes met in the mirror. “You’re prettier then Kelly,” he
said. “Now one more thing,” he said as he held my shoulders. Sean used
something to open my mouth and hold it open. They were so strong I couldn’t
fight back and again before I knew it my tongue had been pierced and a
silver ball with pin and screw on ball had been placed through my tongue.

“Perfect,” Sean said. “Usually I get a couple of hundred dollars for this
but you can pay me back somehow later. Ok, Jill?”

Joe reminded me as he said for the last time by whispering in my ear and I
thanked Sean for taking such good care of me and making me pretty.

“Now don’t forget with that pierced tongue,” Sean said, “you can drive a
guy crazy by rubbing it on his dick or when licking his asshole. A guy
knows when a chick is doing her best and our friends who are coming over
aren’t very nice to chicks that don’t do their best. As a matter of fact,
Jimmy likes a girl who knows how to lick asshole so make sure you don’t
fuck up with him or anyone else.”

The next thing I knew was Joe had lowered my bra and held me again while
Sean pierced my nipples and put bars through them that held a chain that
hung down. I was so shocked as I saw myself in the mirror. But before I
even had a chance to think about all of this Sean and Joe told me to get up
and lean over the bed. I was so submissive at this moment I went to the bed
and leaned over right way.

“Good girl,” Sean said as he gentle slapped my sore ass cheeks. He rolled
down my panties and said to Joe to hold me. Before long he had put a tattoo
on my left ass cheek, on my right ass cheek and one above my ass
crack. (Later I learned my two cheeks said spank me and the words above my
ass crack said, Piss & Cum In Here, with an arrow pointing down.) By 5pm a
band of tattoo surrounded my ankle in a geometric pattern that actually
repeated the word, “SISSYJILL.” Just above my pubic mound was in small
block letters–sissy clit.

Also in small letter on the back of my thigh below my panty line was the
words in the wings of a butterfly and in color saying, “Pull my panties
down.” I would learn later what I couldn’t read. And finally over my left
nipple was the words, “I love(in the form of a heart) to lick ass.”

I couldn’t believe it. Joe and Sean had put some clothes on the bed and
told me to be ready downstairs by 6pm. Joe whispered in my ear just before
they left that he still had at least 3 loads of cum for me tonight.

I stood looking in the mirror at my ear studs; titty clamps with chain and
then opened my mouth and looked at the silver ball through my tongue. Gosh
in less than 7 hours look where I was. I went to the bed and saw what they
had put out for me. There was a pink spaghetti strap camisole that no
matter how I tried would not cover up that heart. The skirt was a skimpy
black silk that didn’t even cover my entire panties so that little design
with “pull my panties down” was quite visible. A pair of white socks that
had a frilly overhang and didn’t cover my anklet tattoo. Also, I had never
see socks like this because they were cut out so my pink toes showed. A
black satin choker and black open toed shoes with thin straps up my feet
with my toes showing. The shoes had heels but weren’t as high as what I had
been practicing in so I was able to walk in them.

There was Jane’s tennis bracelet that I also put on and a pink butterfly
clip for my hair. When I looked in the full-length mirror on the closet
door I couldn’t believe the slut I saw. Anyone sitting down could easily
see my panties.

“Are you ready Sissy,” Sean called from downstairs. “Come to the game room
as soon as you are,” he continued. I wasn’t ready as a person but I had no
choice but to go down. As I entered the game room Sean was filming me
walking in. The skirt although not real tight felt like it would tear off
if I took big steps so I was very careful as I walked in.

“WOW!” Joe stammered. “You are one fucking great looking cum magnet,” Joe
continued and then said harshly I should always be polite when a guy gives
you a compliment. He raised his hand and I knew it was a signal. So, not to
get smacked I turned to Joe and said, “Thank you.”

“Ok, I love to get a good blow job right now,” Joe said, but Sean said it
would mess me up so soon before the guys arrived. Instead, Sean said, “why
don’t you give her a fresh load in her panties.”

So there I was in my house totally different than earlier in the woods but
doing the same thing. This time he had me use some Vaseline as I jerked him
off. While I was doing this Sean put on some music and Joe’s cock got hard
as a rock. He wanted me to smell it and lick it a couple of times and then
he held my skirt up and pulled my panties out. Sean just watched and Joe
kept telling me what a good “little cum slut,” I was.

The next thing I knew he was blowing another thick load of cum on my sissy
clit and down into a puddle in the cotton crotch, which was filled with dry
cum from earlier. As if on cue, as soon as he had finished and I had pulled
up my cum filled panties tight against me the doorbell rang.

“Go answer the door Jill,” Sean said. As I walked Joe’s fresh load of cum
slathered against my balls. I got to the door ashamed of my predicament and
opened it. There were 3 guys standing there. In my pretty girl voice I
said, “Hello, won’t you please come in.” One guy was nearly six and half
feet tall. He was the last to walk in and he walked over to me, put his
arms around me and said, “Hi Jill, I’m Jimmy.” And before I could do
anything he leaned down and started to kiss me on the lips and then pushing
his tongue into my mouth. I could feel his massive cock against upper
chest. I he was standing erect his cock would be almost mouth high. As he
kissed me he played with my ass and then rubbed the front of my
panties. The cum oozed around as he did that and he stepped back and with a
smile said, “hmmm looks like you get wet easily.” Then he saw the little
heart over my left breast and said, “Well Jill, I love to have my assed
licked so I guess we’re going to have a great time together.”

So, this was the Jimmy they had talked about earlier. The other two guys
had walked in and were talking with Sean. Both seemed pretty fit, perhaps
early twenties.

To be continued

Contact: fundipity@mediaone.net

Date: Sat, 15 Sep 2001 11:12:47 -0400
From: fundipity
Subject: High School Dilemma Part 2 (TG)

High School Dilemma

Part Two

(final chapter to follow)

By Lauren Westley

Jimmy told me to get him a beer. As I turned to go to the kitchen Sean
called out that I was to curtsy and say, “Yes Sir” when a man was talking
to me. I turned back to Jimmy and curtsied saying, “Yes Sir.” But, again
Sean called out and reminded me that a proper curtsy was with my fingers
holding the hem of my skirt and pulling the skirt out a bit. So again I
curtsied and said “Yes Sir.”
Just then Joe chimed in and told me that since I wasn’t a ‘proper’ girl
that I should do a different type of curtsy. This he said would entail
holding the hem of my skirt a little towards the front and when I
curtsied I would pull the skirt up showing my panties and I wasn’t to
rise back up until the man gave me permission by either tapping me on the
head or a verbal acknowledgement.
So again I curtsied but this time I held the front of my black silk
skirt showing my cum soaked white satin crotch. My pink spaghetti strap
camisole hung in such a way I knew Jimmy could see the chain going from
one nipple to the other.
“Hey honey your pussy is really wet,” he said as he grinned. And since I
couldn’t rise until he said so I found myself teetering on the red
high-heeled shoes. Nothing seemed to match except for the sluttiness.
Finally Jimmy said I could get up and get him that beer. While I walked
to the kitchen passing one of the other guys (I found out later his name
was Paul) he stopped me and told me to raise the back of my skirt so he
could see my tattoo better.
It was at this point that I finally found out what was written. Out loud
Paul read the words pull my Panties down.
“Great tattoo Sissy Jill,” he said. (Obviously he could read my ankle
tattoo as well). Then he proceeded to pull them down as I held my skirt
up. First he read out loud the words “piss and cum in here,” with the
arrow pointing to my hole and with enjoyment said he would be “glad to
later.” Then he pulled them down some more and read the two words, one on
each ass cheek, saying, “Spank me.”
“Absolutely,” he replied, “but just a little later.” He began to pull my
panties back up when he said to his friend, “Larry do you think I should
keep her panties rolled down in the back so we don’t forget what she

Larry replied with a quick “Yeah, sure Paul that’s a great idea.”
And then Paul rolled my panties down over my ass and left them in front
with the puddle of cum against my “peni-clit” or “puny-clit” I’m not sure
what he said.
“Get me a beer also Jill,” Paul said. So I turned and curtsied with my
bare ass against the black satin skirt and my white cum filled panties in
the front waiting for him to give me permission to get up. He took his
index finger and put it under my chin and suggested I should smell his
crotch before I got up. My nose touched the fabric of his trousers at the
base of his balls. “Sniff it boy-cunt,” he demanded. When he wasn’t
satisfied with my nasal inhalation he grabbed my hair and pulled it and
then I sniffed hard and long. I could smell masculine sweat, stale urine
and a bit of a hidden musky odor.
“Ok, now you can get up and get me that beer. I just wanted you to get
use to the smell of the perfume that should turn you on. When you smell
this you can’t be far from good spunk.” Paul pulled my hair and I knew to
get up. My curtsy finished I walked to the kitchen my bare ass being
rubbed by the black silk skirt as my four-inch heels made my ass sway
back and forth.
“She’ll do nicely,” Jimmy said to Joe as I turned into the kitchen. I
started to cry as I got the beers. Four beers and four glasses I counted
as I put them on the tray and started out to the living room holding the
“No, No you twit,” Sean yelled when he saw me. “You are waitressing us
so carry the tray in one hand as they do at a bar.” It was so difficult I
thought I’d drop everything on the beige living room carpet but by taking
smaller steps and going slower I was able to continue on. “Very sexy
walk, I like it,” Joe said.
For the next hour or so I just kept going from the kitchen to living
room serving them as they watched a football game. Each time I served or
picked up empties I had to bend over (the only way I was allowed), which
made my skirt slide up over my ass revealing the writing on my ass.
The half came and I was serving Larry when he started to rub my ass
saying, “Cunt, do you know how to fuck a cock?” I heard him ask Joe if it
would be ok for, “the cunt to fuck the jism out of him?”
Joe said, “sure” and the next thing I knew I was walking with Larry
holding my hand to my bedroom. As we walked Larry kept sliding his hand
under my skirt and rubbing his finger in my crack. By the time we reached
the stairs his index finger was pushed up my hole. He told me to grind on
his finger since I was going to “fuck the jism out of him” and should
show him how much I wanted it.
Walking up the stairs was so precarious. Once I teetered a bit and slide
down on his finger to his knuckle. He said, “good girl.” We got to my
sister’s room and he complimented me on the pink and girly decorations.
As he closed the door he said I was going to fuck him and he began to
take his belt off. Holding the belt he continued that he would use it if
I didn’t smile and fuck him good. He turned on the radio next to bed and
told me to dance a little and then come and feel his balls and when he
was hard enough I was to fuck him. If I was “lucky he would both cum and
piss in me.” He got up on the bed with his pants removed and only his
jockey’s on and his shirt. The belt was by his side curled up like a

Nervously I began to dance and turn, bending over and showing him my ass
as he rubbed his crotch. I looked at him and he said, “cunt just look at
the prize, my cock is full with a feminine present.” He was very hairy as
I continued to dance. After about five minutes he removed his shorts and
told me to climb up and “suck him and fuck him.”
I climbed up on the bed between his legs my eyes watery from the
humiliation I felt. His hairy legs rubbing my soft hairless skin as my
face rubbed in his balls. He was very musky smelling as I started to suck
“Good little cunt,” he cajoled as he stroked my hair. My red lips
sliding up and down on his shaft as his cock began to harden. He wasn’t
very long. At most 6 inches but his cock was as thick as a late summer
cucumber. The corners of my mouth ached as I bobbed up and down as his
cock hardened.
“Okay cunt now is the time for you to ride the rocket,” he said with a
smirk. I began to remove my panties but he slapped my face and said,
“whore just leave your panties the way they are and fuck me.” So with my
panties rolled down in the back and cum filled in the front I held his
cock and guided it into my (he made me say) ‘pussy’.
Slowly at first his cock head began to push into me. I felt like I was
being fucked. I felt like a cunt as his cock slid up my hole filling me
with pressure and heat. He put his hands on my hips and said, “ride
cunt.” I was bouncing up and down on his cock my own ‘clitty-cock’
jiggling in Joe’s cum puddle. Before long he started to breathe heavier
and moaned, “fuck it out of me cunt. AHHHHHHHHH” and then exploded load
after load of white-hot jism up my bowels, deep inside me.
He held my hips after he shot. His face was flush as he held me on his
cock. “Just one more thing I need to do cunt and if you are the girl I
think you are you’re going to love it. He rolled me over with my face in
the pillow. About a minute later, his cock softened but was still thick,
he began to pee a torrent of urine up inside me. He rubbed my belly and
told me this would be the first of many times he would “fill-her up.”
“Now cunt when you get up don’t spill a drop because if you spill any by
accident, without permission, then your ass will be as red as your lips.
Do you understand?” I nodded I understood. “Now when we walk back in the
room I want you to look girlishly satisfied and have your fingers on my
crotch. Everyone had better thing you are one happy little cunt. Oh, and
fix your makeup before we go down. You need more lipstick.”
I got up and felt his full load of piss and cum in me as I started to
get off the bed. “Hey cunt, tongue wash my cock clean,” Larry commanded
as he slapped my ass. So I turned and saw his messy cock and moments
later I had given him a tongue bath with my pierced tongue and now my
mouth tasted like a sitcom and piss sauce.
“Ok now get some lipstick on and we can go downstairs,” Larry said

A tear fell from the corner of my eye as I applied the lipstick and
tidied myself up. I turned toward Larry and he said, “Smile.” So, I
smiled and we walked out of the bedroom. I had to keep my ass cheeks
squeezed as we descended the stairs. I could even feel myself slosh a bit
inside. Larry stopped me on the stairs and then he pulled my skirt up in
the back so he could see my ass. “Just to be sure you don’t spill any,”
he said with a satirical tone. So we began down the last half of the
staircase. Larry put his hand on my ass rubbing my cheeks and telling me
how proud I must feel to be carrying his load. And then he had me put my
hand on his crotch as we entered the living room. As we walked into the
room I wiggled a bit to hold in Larry’s pee and cum cocktail.
Larry said he liked that and I should get him another beer.
The game was back in progress so the other guys were sitting around the
TV but I noticed Joey smile as he looked at my hand on Larry’s crotch. As
I walked to the kitchen Joey turned to me and asked if “Larry was a good
fuck.” I said “yes” and then politely asked permission to go ‘potty’.
“Larry,” Joey called out, “did you take a leak in Jill?”
“Sure did Joey and I told her she’d get a spanking if any of my piss or
cum leaks out.”
“Well Jill, Larry wants you to keep it in until he says so, so get me a
beer also,” Joey said.
During the next half- hour I waddled along carrying beers to the boys
feeling Larry’s wetness inside with every step I took. I held it in. Then
while I was serving Joey another beer he started to rub my ass and said
with a cynical leer that he ‘need to use the toilet.’ With that he took
my hand and we started walking out of the room when I heard Jimmy and
Sean said they had to ‘piss’ also.
“You lucky cunt,” Joey said as he turned and made me walk to the sofa.
He had me bend over the arm of the sofa with my pee filled ass exposed to
them. I heard his zipper as my face was in one of the pillows. Next he
grabbed my hair and I felt his cock push into my ass.
“Larry so piss is so warm, I can feel it around my cock. I’m getting so
hard. Jill is going to be so lucky because now I have to cum first. And
with that he began fucking me while pulling my hair. Before long I heard
him sigh and then start grunting, “here it comes cunt.” And with that I
knew he had shot his load.
After a few moments, with his cock still hard I felt his pee torrent
into me. He continued to sigh, “AHHHHH” as he peed.
Then Jimmy with his massive cock did the same. I was so full my tummy
pushed hard against the sofa’s arm. When Sean started to fuck me he told
the boys I was too full and Joey gave him something. He said when “a dike
is full, plug it.” And then he laughed while I cried. Just before Sean
came he pulled out and stuck something in my ass. Later I realized it was
a butt plug. He shot his load in my ass crack and told me to pull up my
panties and follow him.

3 Responses to “High School Dilemma”

  1. vic Says:

    such incredible humiliation.. wow!

  2. dennis Says:

    she is such a lucky girl wish i coud be so lucky

  3. sissyboydanni Says:

    Such a sexy story it made my little 4″sissycock so hard! When I was reading it I only had on heels,nylons,a garter belt & bra. So while masturbating my neighbor walked in caught me! After reading what she caught me reading she called her boyfriend telling him come over and fuck her neighbor the sissyfag . Which he did….

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