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The Sissy-boy Middle School Slut
February 20, 2011

The stories posted here have all reached certain standards of readability and content. I focus on collecting stories that involve humiliation of a young, feminine submissive by a dominant male. As a rule, all the stories posted here are X rated, but they involve more than straightforward non-consensual sex. Instead, these stories will pay attention to the emotional and psychological humiliation of the submissive. More often than not, there is a training or feminization scenario through which the sub learns to submit to and please "real men".

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Riana's Collection of Sissy Humiliation Stories



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A collection of sissy humiliation stories I've read and liked, with strong emphasis on dominant males and submissive boys or sissies.
“How many dicks have you taken in here Samantha?” he asked
“What? I uughgh I haven’t ever had anything in there Sir!”
“Good you were saving it for me …from now on this isn’t your asshole this is your pussy do you understand me?”
He started to bang my pussy with his two fingers slowly at first then faster and faster. He turned me sideways so he could get a better angle on me and continued to finger fuck me as he asked me some more questions and told me what the new rules were going to be.
“Your pussy belongs to me now you sissy queer. And that means whenever and where ever and whoever I give your pussy to to use …you give it to them no matter what! you understand me ?”

Note: This story was dynamically reformatted for online reading convenience.
The Sissy-boy Middle School Slut (M/b, b/b, MMM/b, pee, scat, diapers,
humiliation, gangbang, prostitution, pedo) by Jill Jordan
My mom had let me sleep in this morning partly because it was a Saturday
and partly I think because she had gone out on another date with her new
boyfriend Max, and I think she wanted to have the extra rest as much as I
did. She and my dad had split up about 10 years ago when I was only 2 and
she hadn’t really dated that much that I could remember for most of it even
though she was a total babe! At least thats what my friends always said
…at least the two friends I have Bruce and Doug both said that they
wouldn’t “kick her out of bed for eating crackers!” It had just been my mom
and me for as long as I could remember, she always said that we didn’t need
anybody else in our lives besides each other, and that was the way it was .
I have always been real little for my age, even now at 12 yrs old and a
sixth grader I was the smallest person in my class; smaller even then most
of the girls. I was constantly teased and picked last for teams because of
my small size. I didn’t even weigh 90 lbs soaking wet! How do I know ?
Well I used to weigh myself every morning when I woke up usually wearing a
soaking wet diaper that I was required by my mom to wear because I was a
bed wetter. No Beu I didn’t have alot of friends guy or girl but my one
bestes friends Doug who was 4 years older than I am I don’t know when
things happened in my life that made me the way I am, mom was convinced
that it was because I didn’t have a ‘male role model’ around like a dad to
instill in me that tough guy part of my personality that liked girls and
wanted to work on cars and stuff like that. I was raised by my mom and was
basically never shown how to be a boy and then later a soon to be teen.
One of the things I got teased about alot was always sitting down to go to
the bathroom even if it was only pee; just like my mom had always done .
We neve had much money at all so I wore alot of clothes that mom was able
to get for free from our church, and that included for some reason almost
all girls clothes. Our pastor said that all they were getting in were
girls clothes because all of the boys clothes for boys my age were usually
totally worn out because boys were so active at my age. So from about age
4 thru age 11 i had two sets of clothes: one set of one or two pairs of
pants and a couple of shirts were my ‘school clothes’ and a dresser and
closet full of skirts and blouses and dresses and panties which is what I
wore just to hang around the house. I always sat to pee because it was
always so easy just to lift my skirt or dress up and pull down my panties
and go versus trying to go like the other boys did standing up. At night
my mom would come into my room and help me change out of whatever girls
clothes I was wearing and into my night diapers and my girls ‘Nightie’.
Then the next morning I would lie in bed usually in my soaking wet diaper
and plastic pants until she came in and got me undressed and dressed agian
for the day. She always made such a big deal about how pretty I was as she
went through the ritual of undressing me and then redressing me just like
she did this Saturday morning.
“Alright are you all ready to get changed and get out of bed dear?” She
asked all to enthusiastically “Oh my!! … were these panties in the last
box of clothes we got from the church Sam?”
I nodded my head up and down to a yes. Since she had gone out with Mr.
Wonderful last night early she had left my humiliating changing ritual to
the babysitter; a girl only 4 years older than I am who lived down the
street about 5 houses. Mom hadn’t seen that she had put me in a pair of
pink girly plastic pants that matched my nightie we had just gotten in our
last box of cast downs from the church.
“These are so darling!! you look so sweet in them with their pink
little bows all around them and their satiny looking material! I have
always told you how cute you looked in pink panties but even I had no idea
how cute these would look! Would you like me to save them out so you can
wear them later today? I nodded yes
” I think I am going to leave you in diapers for the day Sammy because
Max stayed over last night and I need to take him back to his truck so you
will be here alone for an hour or two and I don’t want any accidents like
we had last weekend ok?”
“Now lets get you changed and then I will fix us all some breakfast ok
Sammy?”
“But mom!” I pleaded “I don’t want Max to know I wear diapers still!”
“Don’t be silly Sammy Max knows all about your accidents I told him last
night in case you came and tried to get in bed with us”
“It’s ok honey he understands ….I also told him that the only clothes
we had been getting from the church lately were hand me downs from families
with only girls and he’s ok with that too. He said alot of kids have to
wear girls clothes …’you got to wear what you got….a boy can’t go
around nude’ he said. So don’t be silly he is like a part of our family
now… and who knows maybe someday he will become a real part of our
family and his son Rod would be your new big brother!” she said as she
finished changing me and pulled up and snapped the waist band around me of
my ‘new’ pink plastic pants.
“Now come on into the living room and you can watch cartoons with Max
while I cook up some breakfast. Words cannot describe the feeling of total
and utter humiliation as I walked out into the living room with my mom
dragging me by the hand wearing my short pink nightie and matching plastic
pants to where Max was sitting in the chair.
“Oh my she…I mean he is pretty in those girls clothes Jackie” Max said
as he motioned for me to turn around so he could see the entire ensemble.As
mom twirled me around he let out a long wolf whistle as my whole body turn
red with shame.
“Hey Jackie I called and talked with Rod and he said he would be able to
come over and watch Sam for you while we are gone this morning if I let him
take my truck tomorrow. So he should be here in about 30 minutes”
“Oh Max that’s great news!! Thats great news isn’t it Sammy? You get
to finally meet Rod today isn’t that great ? I’m sure you two will become
the best of friends! “Breakfast went by quickly and before I knew it Rod
was knocking on the door to our trailer.
“Sammy that must be Rod will you go let him in?”
“Mom I can’t let him in dressed like this!”
“Max honey can you let Rod in and kind of fill him in on Sammy for me
while I finish getting ready?
“Sure thing Jackie…Don’t want the boy to have a heart attack do we”
hahahaha he laughed as he let him in.
“Hi Son thanks for helping us out today…there is a couple of things I
didn’t tell you on the phone…lets step outside here on the porch and I
will fill you in on…..” I couldn’t here what else he was saying so I
quietly snuck over to my open window and listened quietly as Max and Rod
had their talk about me.
“What didn’t you tell me dad?” he asked
“Well its like this son, Jackies boy Sam….well the boy is a little
fairy. He is 12 years old but he doesn’t look it and he prefer to wear
frilly girls clothes and still has to wear diapers because the little
faggot wets the bed. Right now you won’t believe it but he’s wearing a
short pink night gown with little satiny bows all over it and a pair of
matching plastic pants over his diaper. I don’t mind saying either son
that he’s an awfully cute little thing in that outfit for being a queer ”
“He wears girls clothes and a diapr? Daaaaddd what have you got me
into?”
“I haven’t gotten you into anything……. and after you see him you’ll
want to get into him …especially if the boy can suck a dick as well as
his mom…come in and see for yourself”
“OK if you think it’s ok?’ I quickly jumped into my bed as they came
back inside the trailer and pretended I was asleep.
Max knocked on my door and opened it as he said ” Sammy …?? Sammy…?
Rod is here and your mother and I are leaving come out and say hi to him
before we leave!”
“Alright Sammy I know your not asleep if I have to come in there and
drag you out I will make you go to school Monday in that outfit!”
Those were the magic words for me, because while I didn’t mind having to
wear girls clothes around the house when I was home from school and to bed
and stuff …in fact I actually kind of liked it . There was no way I was
going to go to school dressed like this and my mom always made good on her
threats. I slowly got out of bed and walked clutching onto my mothers
waist and trying to hide behind her into the living room to meet Rod.
“Hi Sam my name is Rod” he said extending his hand. I peaked out from
around my mom and peeked at him and put out my hand too. Max was in a big
hurry to get out of there so at that he grabbed my moms hand and yanked her
out the door as they both said the normal things moms say when they are
leaving their child with a sitter. “We’ll be home this afternoon” and
“make sure he eats lunch” and “There are more diapers in his dresser if he
wets the one he has on now” Ouch that last one hurt.
I heard them peel out of our gravel driveway and head towards town.
Rodney motioned for me to join him on the couch. Which I did .
” So do I call you ….Sam….. or…Sammy…or Samantha?”….he said
laughing I just sat down and shrugged my shoulders ‘OK then Samantha it
is!…Look Samantha I can imagine how embarrassing it must feel to be
dressed up like that..not to mention being a fag and all. But you don’t
have to be afraid of me or nuthing …I mean just as long as you do what I
say and stay out of trouble and stuff we will get on just fine. ..OK?
“Man dad was right your are about as cute of a girl a I have seen in
along time Samantha…why don’t you come sit over jhere by me so I can
check your diaper and make sure its not wet and you and I can have a talk ”
“Well I’m just glad to see that you can talk, but unfortunately since I
am responsible for you and all I need to check it for myself …ow get on
over here now!”
“But Rod…” Smack! I didn’t even see his hand coming before he had
smacked me in the head so hard that it made my ears ring and my head felt
like ir has been caved in. I started to cry as I stood there in front of
him with my head down in quiet humiliation.
“You dont want to test me girl because that was just a love tap compared
to the next one you’re going to get if you back talk me again and don’t do
exactly what I say and when I say”
“You Understand ??….now put your hands in the air …thats right
staright up there while I check out you diaper” With my hands help up as
straight as I could get them Rod pulled down my pink plastic pants and slid
his hand down the front of my diaper. I shook alittle as his hand came
into contact with my dinky and then as he figured out what he had done he
gently grabbed it with his hand and started to slowly pump it and rub it
and feel my sack with his fingers.
“Your right” he said as he slowly continued to masturbate me “You feel
dry to me right now!” By this time my dink was as hard it can get and I let
out an audible gasp….”You like that little girl dont you? Youv’e got a
little stiffy from this don’t you faggot boy.”
Who wouldn’t have one after a minure or two of him and rubbing their
privates.
“mmmmmmmm” …I moaned softly as he continued to feel his way around
down there with his hand.
“OK now turn around hands on your ankles and keep them their or you will
not like what I do if I have to smack you again!! Are we clear…faggot?”
I nodded dumbly and turned around and bent over and grabbed my ankles hwile
he lifted up the back of my nightie and once agin pulled down my lastic
panties and then slid down my diaper about halfway to my knees.
“Ok now this won’t hurt at all if you do exactly what I say ok
Samantha?”
“CRRAACCCK”! His open hand smacked one of my ass cheeks.
“WWHHHEEEE” I cried out reaching back to grab my lit up ass.
“Not so fast faggot now bend over and grab your ankles and if you so
much as move 1 inch i will take off my belt and give you the thrashing of
your young girly life …now when I ask you a question I expect that you
will answer me with respect…I want to here you answer ‘yes sir”do you
understand me you queer little diaper girl?
“That’s better now back to your position” he ordered pushing me down to
once again grab my feet.
“I need to see if you still have your cherry” he said as he started to
work his finger into my rectum. He was finding that it wasn’t a very good
fit because it was so dry. I think he must have been thinking the same
thing because he reached over onto the table and scooped some margarine up
with his finger and spread it onto my asshole. That made all the
difference in the world as he easily slid one then with alot of pain and
discomfort two fingers into my virgin ass.
“How many dicks have you taken in here Samantha?” he asked
“What? I uughgh I haven’t ever had anything in there Sir!”
“Good you were saving it for me …from now on this isn’t your asshole
this is your pussy do you understand me?”
He started to bang my pussy with his two fingers slowly at first then
faster and faster. He turned me sideways so he could get a better angle on
me and continued to finger fuck me as he asked me some more questions and
told me what the new rules were going to be.
“Your pussy belongs to me now you sissy queer. And that means whenever
and where ever and whoever I give your pussy to to use …you give it to
them no matter what! you understand me ?”
“Yes Sirrr” I gasped as the intense pounding his hand was giving ,my boy
pussy was starting to make me feel real funny down there and I couldn’t
stop from panting like I was hyperventilating.
“You like having someone fucking your little pussy don’t you sissy boy?”
“Yes Sir” “aaagghgghhhhhhh ooohhhhhhh yyyeeeooowwwwww!!” I couldn’t help
it my body just sort of took over and I started shaking and this wave of
incredible heat swept over me from head to toe and I could feel my
asshole..I mean pussy contracting on his fingers as he pounded them in and
out of me.
“You just had your first orgasm sissy boy had did that feel?!
“Great …really great wow that was soo freeking kewl” ..”Ah Sir”
“Good Girl” he said as he not so gently took hei fingers out of my ass
“now turn around here and face me and get on your knee” I did as I was told
stopping only to pull my diaper and plastic pants back on and kneel down in
front of him. “Do you know what we are going to do next sissy”
“No sir” I answered unsure of what he meant.
“Do you mean to try to tell me that you’ve never sucked a guys dick
before?” “Dressed the way you dress and looking the way you look?”
“Um no sir I haven’t before ..no one has seen me dressed like this
before except my mom”
” Well one of ,my favorite things in the world to do is to have my dick
sucked by girls or pretty little fairies like you. I like them so much
that from now on I not only own your pussy but I also own your mouth ..you
go that sissy? and no matter what else you are doing or no matter where we
are if I say sammy suck my dick you are to stop everything you are doing
and drop to your knees and undo my belt and take out my dick and suck it
until I tell you to stop. And that’s not all since I own it if I tell you
to suck anybodies dick who I am with or one of my friends ..then you drop
to your knees and suck his dick until he tells you you can stop
understand?” I nodded that I did with my eyes staring down at the floor. I
knew that from now on my life had changed. Maxes son Rod was the devil and
I had just sold my soul.
“Ok Samantha suck my dick! and you better not let me feel your teeth
even once or I will knock them out so I won’t have to worry about feeling
them again. ” Slowly with my eyes down I groped for his belt and then
unzipped his zipper. As I got it down Rod stood up a little to let his
pants slip down his legs to give me full access to his dick.
“Go ahead sissy this is what you want isn’t it” “a nice big dick to suck
on and a mouhful of my cheese as a reward for a job well done …well fag
start earning it”
I reached into his boxers and slowly took out the biggest dick I had
ever seen. I mean I grabbed this thing with both hands around it like a
baseball bat and still had room for more. Now granted my hands aren’t very
big but neither was my mouth. Now I knew why they named him “Rod”. He
pushed my head towards it and kept the pressure in it and said “kiss it
…you will need to show it and me the proper respect ..sucking my dick is
the only thing you are good for and the only reason we won’t toss yer ass
out to some orhaned faggots home when my dad and your mom ge
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