Note: This story was dynamically reformatted for online reading convenience.
 
 Licking My Mother's Boots 2 It is my 14th birthday.  I have spent the last
year being my mother's boot slave.  Everyday my job is to gather up
whatever footwear she has worn that day and clean and polish them.  I have
gone through 3 stages in this process.  The first stage was one of absolute
bliss.  To be told to get down on my knees and lick my Mother's boots clean
was the most wonderful thing that had ever happened to me.  The second
stage was disgust when I discovered that this was pure drudgery.  Even
without all the other housework I am required to perform, licking one pair
of boots is fine but licking multiple pairs of different styles of shoes
and boots is quite another thing.  But that stage only lasted until I had
caught up with my duties.  Once I was back to one pair a day, stage three
was acceptance.  No that is not accurate either.  Stage 3 is delight.  I do
not know what may happen today but Mother has summoned me into the living
room for what she says is something special for my birthday.  Entering the
living room I notice that there are several wrapped packages set on the
floor by my Mother's booted feet.  As is my custom I immediately get down
on my knees and crawl to her and pay homage by getting on my belly and
begin kissing her boots.  "Jeremy you may rise to your knees.  After all
today is your birthday.  Before you open the gifts I have here, I have a
special gift.  Your aunt Rose is going to take you into town for a complete
makeover.  That will include having your hair curled, your nails done and
your body waxed.  I want you to feel pretty on this special day.  And then
she is going to take you shopping to get a complete feminine wardrobe.  How
does that sound." Well, I had always wanted to dress up like a girl so what
could I say but that sounds wonderful Mother.  By the time that Rose
arrived I was in a state of sexual excitement, anticipating what we were
going to do together.  Rose immediately told me to get undressed as she
suspected that I might embarrass myself otherwise.  I had no idea what she
meant.  I was though thoroughly embarrassed as she made me strip down until
I was naked from head to foot.  My cock was sticking straight up in the
air. "That will never do." She said pointing to my dick.  She walked over
to the side board and came back with a ruler and a roll of tape.  I had no
idea what she was planning until she took the ruler and slammed it down
across my erect cock.  I tried to block the next blow by covering myself
with my hands but that did not deter her.  She just brought the ruler down
again this time on my knuckles.  This caused me to pull my hands back and
that left my cock exposed to another blow.  Well it was not long before I
lost my erection.  She then forced my cock back between the cracks of my
ass and using the tape she secured it in place.  She then produced a pair
of very tight stretch panties and made me put them on.  The result was that
no matter how excited I might want to become, my bulge would not show.  I
was then allowed to put on a pair of white shorts and a t-shirt and a pair
of sandals.  Looking at me no one would know that I was not a typical
teenage boy.  But hopefully before too long I would look like a typical
teenage girl.  Our first stop was the wax salon.  Rose introduced me to the
woman technician and pointed to a flat bench like table.  She then told me
to remove all my clothes and the technician laughed when she saw the tape
job Rose had done to keep my organ out of the way.  "I am afraid you will
have to re-tape him.  I was instructed to wax that area as well." "That
will not be a problem.  I still have my ruler in case he gets another
hardon." "Oh I am sure he will get hard when I start working on him, but
usually they lose their ardor when I start pulling the wax off of them."
She was right of course.  Having a woman applying wax to your body may be
exciting, but having it ripped off taking the hair out by the roots is not.
An hour later I was as smooth as a baby's bottom from my neck to my feet.
Rose had no problem re-taping my penis.  And once I had the stretch panties
back on, there was no fear that I could attain another erection.  The next
stop was the hair salon.  My mother had insisted that I allow my hair to
grow out and it had reached my collar.  I loved the feel of having it
washed, trimmed and curled.  While that was being done, my nails were being
taken care of as well.  I was given a complete pedicure, including the
brightest shade of red polish.  I now knew that when I left the shop there
would be no hiding the fact that I had received some feminine treatment. 
The nails on my hands were accentuated by adding plastic tips so that they
extended about an inch and a half beyond the tips of my fingers.  I
immediately recognized that I would have to really practice to be able to
use my hands for even ordinary tasks.  They took a long time working around
my eyes.  Of course I could not see the result but I could feel my eyebrows
being plucked and something being applied to them and my lashed.  Cream was
applied to my face before a layer of makeup was added.  And then the
finishing touch was a bright shade of red lipstick.  When they finally
allowed me to look in the mirror I did not even recognize myself.  I could
swear that a beautiful young girl was staring back at me and my heart
swelled with pride.  Rose looked at me and bent down and gave me a kiss on
the cheek.  "You are truly lovely.  If it wasn't for the flat chest you
would have every boy in the mall drooling over you.  But don't worry by the
time we are finished you will have a nice rack to go with your other
attributes.  Before leaving she purchased the cosmetics they had used on me
so that I would have my own set.  She put them in her purse until such time
as she could buy me one of my own, which she did at the first department
store she came to.  At first I felt a little funny carrying the purse over
my shoulder but that was only until I convinced myself that it didn't
matter as I was not likely to meet anyone I knew and even if I did they
would not recognize me.  The next stop was the lingerie department.  A
young saleswoman helped Rose to pick out the perfect matching bra and panty
set for me.  I was allowed to put them on and then breast forms were added
to the bra.  Of course the saleswoman knew that I was a boy but she did her
best to keep her giggles to a minimum.  Even when she saw the tape job, she
just snickered a little instead of an outright laugh.  I was feeling pretty
humiliated by the time we left though.  Our next stop was the girls
department where Rose purchased a beautiful ivory blouse and a plaid skirt
for me.  I was kind of disappointed as I was hoping for something a little
sluttier but Rose told me I was a proper girl not a whore.  And besides the
skirt did come above the knee so I could show a good amount of nylon
covered skin.  "Now all we need is some new shoes." Rose announced.  "I am
dying to see you wobbling on high-heels but that will have to wait for a
little later.  Right now I think a nice pair of open toed sandals will do
fine." I too was disappointed in not getting the heels but I did my best to
hide it from Rose.  After all she had spent a small fortune turning me into
a girl I could be proud of.  More Presents Both Mother and Father greeted
me when I walked into the house.  They spent a long time looking me over
from head to toe and spinning me around to examine me from all angles.  My
Mother gasped when she saw how much I resembled what she would have liked
for a daughter and Dad said he would have a hard time keeping his hands off
of something as lovely as me.  Of course that made me blush and look away.
Mother ushered us into the kitchen and had us sit down at the table.  She
fed us a light lunch of sandwiches which we washed down with plenty of cold
milk.  When we finished she again directed us to the living room.  She
handed me a small gift wrapped box.  When I opened it I found a strange
device made of steel rings.  One end had a fairly large ring.  It was
connected to a smaller ring which was connected to a smaller ring etc.  I
stood looking at it trying to figure out what it could possibly be.  And
then Mother said.  "I thought it was time to get you a chastity device. 
You are fourteen now and it is time you stopped playing with your penis.  I
know you will love it once it is in place.  And she proceeded to put it in
place.  Of course Rose did have to administer a couple more hard blows with
the ruler before it would slide all the way on.  Mother then locked it
securely in place and put the key down her bodice.  No mention was made of
when if ever I would be released.  The next box contained a thick butt
plug. I had spent enough time on the Internet to know what it was for and I
asked why they thought I would want such a thing.  "Jenny, I think we will
call you that from now on.  You have to stretch your hole out a little bit.
Once you get a boyfriend he is going to want to use that and you don't want
it to be difficult for him to get his cock into your hole do you?"

   "Mom, I am not a queer." "Of course you are Jenny.  You just don't
realize it yet.  Once you learn to properly suck cock and please another
boy by letting him fuck you everything will become clear to you.  I fixed a
nice enema for you.  Go up and clean yourself out and insert your plug. 
Once it is seated it will stay in there quite well." I thought of arguing
but I notice she had her riding crop leaning against her chair.  So
obedience is better that being whipped.  When I came back I was walking
funny.  That plug was really thick and it felt like I was trying to walk
with a corn cob pushed up my ass.  "And now here is one more present," mom
said as she handed me a long box.  With almost fear I carefully removed the
wrapping and opened that box.  And for the first time since I had returned
from the shopping spree I was really excited by something I had received.
"I know how much you love high-heel boots.  Mom said.  "I thought it was
time you had a pair of your own." They were absolutely gorgeous.  Made of
black leather uppers that came just to my knees.  The leather was so soft
that I could hardly wait to caress it with my tongue.  But first I was
going to have to wear them for a while.  And that would be a challenge
since they had heels that were a good five inches and came to a pencil
point.  "Go ahead, put them on." My father urged.  "I can't wait to see you
walk in them." And so with a huge smile on my face, I sat on the floor and
began pulling them onto my nylon clad feet.  They fit perfectly and once
they were zippered shut they molded to my legs as well.  Around the top was
a leather strap that when tightened made it impossible to pull the zipper
down again.  With difficulty I got to my feet turning my ankles several
time before I became steady.  Mother insisted that I walk across the floor
and back and laughed every time my ankles would turn.  "It is going to take
me some time to get use to walking in these." "Come over here," Mother
demanded.  I did as she instructed and then she told me to lift my right
foot up and set it on the front of her chair.  This was tremendously
difficult as I was now teetering on just one thin heel.  She produced a
small padlock and locked the strap of my boots so that it could not be
opened.  She then made me raise the other foot and did the same thing.  "I
suggest that you start getting used to your new boots, Jenny.  They will
not be coming off for the rest of the day and you have guests due to arrive
any minute." "Guests, what do you mean?" I said with trepidation.  "Why all
of your friends, of course.  This is your birthday and we wanted everyone
you know to come and share your new persona especially Kimberly.  She is
the girl you were wanting to ask out wasn't she?  And of course your best
friend Tommy will be here as well." I hung my head.  I wanted to run away
but even walking was difficult.  "How could you do this to me?" I cried. 
"I will never be able to face them again once they see me looking like a
pansy." "You seemed perfectly fine the way you looked a few minutes ago. 
If your family can see you dressed as you truly want to be, then I see no
reason your friends should not take part as well." Rose I think you may
have to help Jenny refresh her make up and make sure her lips have a heavy
coat of gloss.  I bet Tommy is going to want to give Jenny a big kiss." I
was totally humiliated when the first guests started to arrive.  My Mother
made me stand out by the drive and welcome each one of them and introduce
myself as Jenny formerly Jeremy.  All the girls giggled when they saw me
and all the boys wanted to pinch my fake breasts.  Tommy bent over and
whispered in my ear.  "If I had known you were a fag I would have fucked
you in the ass a long time ago.  Everyone laughed when the last of the
guests had arrived and I started teetering my way back towards the house.
Tommy pointed and said loudly.  "Look at the faggot, he can't even walk in
his own boots.  I think we should allow him to spend the rest of the day on
him knees." "And just what would you do with him on his knees?" My mother
asked with a sweet smile.  "Well, I can't really say when you are in the
room Mrs.  Wilson." "Why is that Tommy?  I am sure you don't know any words
that I haven't heard before." "Well, I don't know about the girls, but we
boys could find something for him to do on his knees." Kimberly laughed a
little.  "I am sure glad I didn't let him take me on a date.  I am not a
lesbian." "Well, after we open her presents and have some cake, I am sure
your kids can find some type of game you want to play.  But don't forget
before you leave each of you have to give Jenny a birthday paddling."
"Apparently everyone had been informed of the joke on me in advance because
as I started opening my presents I found that every one of them would have
been ideal for a young girl.  I received makeup and vanity mirrors and a
beautiful hair brush.  I even received quite a few pairs of panties in very
frilly material.  I blushed when I opened them and had to show everyone
what they were but deep down I couldn't wait to try them on.  When the cake
was cut and everyone had eaten a piece, my mother took me into the yard and
secured me to the laundry pole.  She then pulled down my skirt and help up
wooden paddle.  "Who wants to go first?  She is 14 today so she needs 14
whacks.  Since there are 7 of you each one needs to give two strokes" I was
surprised when Kimberly was the first to volunteer.  She bent over and
whispered in my ear.  "This is for you thinking that I would ever go out
with a queer." And she swung that paddle with more force than I could
believe she had.  Each of the girls took their turns and then paid their
respects to my parents and left to go home.  All except Kimberly that is.
The boys now had their turn with the paddle and none of them held anything
back.  I was sure my ass was black and blue before the last one put down
the paddle.  The boys then started to file out.  Soon I was left alone with
Tommy, Kimberly and my mother.  Mother unfastened me from the pole but
before I could do anything she wrenched my hands behind my back and secured
them with leather cuffs.  Tommy you said something about wanting Jenny on
her knees.  I am going to leave you kids alone to play whatever game you
want.  If you want privacy there is a furnished room in back of the house.
I will help you take him there if you want.  And with her on one side and
Tommy on the other and Kimberly trailing behind they half led half carried
me into that room.  Mom then blew me a kiss and left me alone.  "Did you
bring you video camera, Kim?" Tommy asked.  "I know that everyone in school
is going to want to see Jenny perform." "I sure did.  Do you want to leave
his girly clothes on or do you want him naked?" "Let's let everyone see him
as he is right now.  Slut get over in the corner and get on your knees. 
Kim set the camera so that he is framed and then you and I can enjoy
ourselves over on the bed.  We don't need to be in the pictures." Once I
was on my knees Tommy tied my ankles together and then pulled my hands down
to them and tied them in place.  Now I could not move unless it was to tip
over on my side.  "Look, you have had your fun.  i Why don't you just untie
me and go on home?" "That isn't a very nice thing to say.  I haven't even
had a birthday kiss yet." Announced Tommy.  "Well come on over here and I
will give you a kiss then." I figured that would put him in his place. 
Instead he went over and looked through the viewfinder on the camera. 
Apparently satisfied that it was pointed where he wanted, he came and stood
beside me and pulled down his zipper.  He pulled out his rock hard cock and
pushed it firmly against my lips.  "Now give me my kiss." He demanded. 
"And don't forget to use your tongue." Kimberly chimed in.  I tried to move
my head away but he grabbed a hold of my hair and pulled me back in line
with his cock.  Kimberly was laughing and egging him on.  "Make him suck it
and get it nice and wet for me." I could not believe what I had just heard
her say.  Why would she want Tommy's cock wet?  "I am going to stick my
cock in your pussy mouth." Tommy declared.  "And if you even think about
biting me, I swear to God, I will knock every tooth out of your head and
then fuck your face anyway." He said it with such vehemence that I believed
him and so when his cock touched my lips again I opened my mouth and let
his meat slide over my tongue.  Kimberly was laughing and urging him on. 
"That's it fuck his face.  Drive that magnificent cock down his throat. 
Make him gag." And of course Tommy followed her instructions.  I mean who
wouldn't.  Kim was a fox.  And then Tommy pulled his cock from my mouth and
said.  "That will do for now, pussy boy.  I think Kim has a better use for
this piece of meat.  The two of them made their way to the bed.  Kim was
now totally naked and she lay down with her legs spread wide directly in
front of me.  I knew I should look away but I had never seen a pussy with
the exception of mothers and Kim's was truly beautiful.  "You know this was
going to be your birthday present from me, Jenny?  But then when your
mother told me that you were queer, I figured I might as well give it to
someone who would appreciate it.  I hope you enjoy the view as Tommy gives
me his cock." And give it to her he did.  As I watched it was obvious that
neither of them had any idea what they were doing.  And from the sounds Kim
made I think she was more in pain than in ecstasy.  The whole fiasco took
maybe three minutes before Tommy began to grunt and thrust forward
forcefully before he finally lay still.  I imagine he would have stayed on
top of Kim and went to sleep if she had not physically pushed him off of
her.  When she was free of his body she got up and spread her legs and
tried to view what if any damage had been done to a tender area of her body
that had never been used before.  When she noticed a small amount of thick
white matter starting to seep out of her she smiled and walked across the
room to me.  Should took me by the hair and forced my head back and then
straddled my face.  "Your mother told me how much you like eating cum out
of a fresh fucked pussy so her is another present from me to you.  Open
your mouth and clean me out good." Dying of humiliation I obeyed.  True I
had licked my own ejaculate off of mother's boots in the past but eating
someone else's out of a girl I loved was a whole new level of torment. 
When she was satisfied that I had gotten about as much as I was going to
pull out with my tongue, she stepped back and motioned for Tommy to come
forward.  "Now make him clean your dick for you.  I need to get going home
before my folks come looking for me." "I will just wipe it on his face and
lips and then I will walk you home." They left me there without even bother
untying my hands.  I don't know how long I was there on my knees but I do
know that when my mother came to release me my legs had cramped and I had
flopped over on my side with tears streaming down my face.  Mom untied my
hands and feet and massaged my cramped legs for a few minutes before
helping onto my feet.  I was still wearing the unfamiliar boots and it was
a struggle even with her help to get myself into the house.  Once inside
and seated on a high stool so that my legs did not need to bend again,
mother insisted I tell her everything that happened with Kim and Tommy. 
"How could you do this to me mother?" I asked.  "You know that I am in love
with Kim and then you ruin any chance I have by telling her that I was
queer.  She was going to allow me to make love with her today before you
lied to her about me." "First, young lady, you best not be calling me a
liar.  I told the girl exactly what she needed to know to avoid heartache.
She was under the misguided assumption that you were on your way to
becoming a man.  And we both know that is not the case.  Kim would never
respect a bootlicker and that is exactly what you are.  I knew from that
first day when I found you with my boot heel in your mouth that no woman
would ever want you for a real man.  So I wasn't going to allow Kim to
throw away her virginity on the likes of you." "Why do you hate me so much?
If you had told me these things, I would have stopped licking your boots.
And I would never allowed you to turn me into a sissy boy." "First, you
could no more stop licking my boots than you could stop breathing air.  It
is what you are.  I saw the look on your face when you opened up your
package and saw that pair of boots you are wearing.  I saw how you caressed
the leather and licked your lips in anticipation.  What was the very first
thought you had?  Wasn't it that you couldn't wait to get your tongue on
them?" I hung my head in shame because she was exactly right.  "Still you
didn't have to ruin everything between me, Kim and Tommy.  Now neither of
them will ever want to see me again." "Oh, you are wrong about that.  She
told me how much she loved forcing you to eat Tommy's cum out of her pussy.
And she said she loved watching you suck his cock.  I know for a fact that
Tommy will be coming by regularly to have you service him orally.  And the
young lovers will come by often to use the bed in the shack.  And of course
you will be tied just like you were today to watch and do clean up duty. 
It will be great practice for you for when I find a woman that will take
you as her cuckold husband.  The end.  If you like this story let me know.
mailto:bootslover4u@yahoo.com