Indentured
by Peg Thebois
Day negative
You Bastard,
I can't tell you how surprised I was to receive your emails. You
wanted to apologize, to beg my forgiveness but how could you understand
everything I have been through. How could you ever understand what it
was like to have the father of my unborn child just up and run away on
me, abandon me and disappear? How could you appreciate the fear and
loneliness of going through a miscarriage with no-one there beside me?
Your first e-mail did nothing but dredge up all the pain and anger that
I had tried to move past, I didn't respond because I didn't think you
were worth the emotional investment it would take to write back. Your
second email I thought you were asking forgiveness and to be allowed in
my life again just because of my position of money and importance now
that I have made partner. With the third and fourth emails I noticed
you honestly seemed contrite and one statement you made over and over,
you wanted to make it up to me, how could you make up for something
like what I went through alone? You said it again and again, you said
you would do anything to make it up to me, anything you said. I have
my doubts that your dedication will even approach what I consider
'doing anything' but since it is so important to you that I forgive you
I think I may just give you the chance to earn my forgiveness and yes
even earn yourself a place in my life again.
Think carefully before you accept this the contract I have included for
you, I doubt you will understand it after all you are certainly no
lawyer so let me layman this out for you. If you sign this document
you are agreeing to enter into a one year term as my employee. You
will perform whatever duties I assign you without question. You will
work for room and board as well as a wage conducive to your
performance, this wage will be held in trustee by myself for you until
you have completed the year of employment. At that time you will have
my permission to leave my employ with your wages, should you desire to
spend any of your wages during your employ on personal effects not
provided as part of your board that will be at my discretion. Should
you accept these terms the breakage of contract fee involves the
forfeit of any wages accumulated to date and repayment of the costs of
room and board.
I want to be clear I harbour much anger toward you for my abandonment,
I plan to make sure by the end of this year I will have worked past it,
I will have had retribution and your penance will have earned you the
forgiveness your guilty conscience craves. To accept my conditions
present yourself one month from today's date at the Starbucks on the
first floor of my firm's building at exactly noon, have these papers
with you signed, you will not need anything else but the contents of
your wallet for the duration of your employment with me.
Sincerely,
Jessica
Day 0 May8,2014
Dear Bastard,
If you are reading this that means you were at the appointed place at
the appointed time. I imagine you were pretty surprised when I just
handed you this envelope and walked out. Did you wait until midnight
before opening it like it says on the outside? I do hope you didn't
open it early and spoil the surprise.
So everything is signed and you are bound to the conditions of our
deal, time for you to begin your penance. I felt humiliated and afraid
as I waited for you to come back so that is the first experience I want
you to go through to understand what you did to me. Tomorrow morning
you are to go to Lilith's Garden as soon as they open at 10:00. There
you will buy yourself a suitably pretty corset and panties, a garter
belt with fishnet stockings and a pair of high heeled shoes. Once you
have paid for it all you are to use their change room to get changed
into it all, I suggest you will probably need some help with the
corset, you may wear your own clothes overtop. Before you leave you
are to ask to pick up an order that was paid for and is being held; the
name on the order is Flora Allyson Grant, that is your new sissy name,
do not expect you will be addressed by that other name you have now
until you are released from my service. I do hope you noticed your new
initials.
You may then take a taxi to my house, I expect you to arrive before
noon, if you are late there will be some extra severe punishments for
you. When you arrive remove all your male outer clothing and throw
them in the garbage can at the end of the driveway, dressed only in
your new lingerie and heels you are to walk up my driveway and ring the
front doorbell one time. Do not worry I will hear it, but you will
wait patiently for me to acknowledge your arrival, do not grow
impatient and ring again or I will add to how long I plan to leave you
standing on my doorstep.
See you soon,
Mistress Jessica
Day 1
Dear Flora,
I could have told you this in person but I enjoy getting these things
out on paper with time to process my feelings. I could tell your feet
were hurting and your face was still red in humiliation from standing
on my doorstep in corset, panties, garter-belt, fishnets and stiletto
heels for 2 hours and 37 minutes precisely before I opened the door,
that is 157 minutes, one minute for every week that it took for your
guilty conscience to push you to write me. Were your arms sore from
holding the package from Lilith's Garden the whole time?
I do hope you enjoy your new accommodations, there isn't much to it
except the bed with it's frilly pink satin sheets, and cement walls
also painted pink; princess meets prison cell. Take off your new
maid's uniform, put your curly blonde wig on the wig stand and hang the
dress and petticoat up in the closet, no doors to it so you can admire
your pretty dress any time you want to. You will no doubt have also
noticed the baby doll nightie hanging in your closet, leave your corset
on and dress yourself in that before you continue this letter.
You are locked into this room at night so I don't have to worry about
you running away, there is a container under the bed if you need to
tinkle. This pink laptop computer is set up to receive e-mails but not
send, likewise all browser functions are disabled, but there is a large
selection of recipes stored on here for you to learn to cook for me.
Notice the doggie door, this is so that you can be brought food and any
other fun surprises I may want to leave you, go there now and you will
find something special.
Now that you are sufficiently puzzled at finding an ice cube tray let's
turn our attention to your entertainment center. That TV can not be
turned off, 24 hours a day it will play a selection of pornographic
movies, but none of the typical stuff you used to enjoy. It will all
be pretty sissies getting spanked, beaten, humiliated, and fucked by
both men and women. You aren't quite at that pretty sissy stage yet
but you will be soon. Before you go to sleep for the night I want you
to pleasure yourself while watching the TV, pleasure yourself as many
times as necessary to fill at least two of the ice cube moulds in the
tray. Then put the tray out through your doggie door and then you have
my permission to sleep.
Good Night,
Mistress Jessica
Day 2
Dear Flora,
I can already tell you are going to be great fun, If I play with you
every morning before I go to work I feel sorry for anyone opposing me
in the courtroom because you bring out my mean aggressive side. Having
you bent over the table baby doll hiked up around your waist was a very
nice view. Even though you were blindfolded I could tell you knew
exactly what it was when I popped that come-cube into your mouth and
like an obedient girl you let it all melt without swallowing. I was
very impressed you took the initiative to go beyond my instructions and
fill a third mould, I had said at least two. You made the cutest faces
when come-cube number two went into your sissy pussy; That is what I
will call your asshole from now on. Even those expressions were
nothing though compared to the ones when all three come-cubes had been
used and I inserted three more cubes. The fear of what might be in
those cubes was well warranted Flora but have no fear those were not
come-cubes from some other man they were my frozen piss. That is
right, at this moment, held in place by that butt plug I inserted after
the cubes your pussy is sloshing with a mixture of semen and piss. I
left your chore list in the kitchen so I won't bore myself repeating
them here when I get home tonight I will relax in my study for thirty
minutes during that time you may empty your pussy and wash your plug
and set the table with dinner for two.
Now I must go to court,
Mistress Jessica
Day 2
Dear Flora,
I do hope you didn't get the wrong idea when I told you to set the
table for two, you looked surprised when I walked in the door with a
man. That was my boyfriend James, did that used to be your name too, I
had never thought about that, and you shouldn't either, you are Flora
now. Should James ever speak to you I expect you to refer to him as
Master James.
I have a special treat for you, something different from the fat-free
milk and oatmeal gruel with soy-beans that will sustain you while you
live here. Your dinner should be right outside your door now, go get
it.
That is right it is canned dog food, there is still a bit of the dog
that you used to be in you I can tell but we'll soon get rid of that,
replace it with bitch. I expect you to eat that like a proper dog
Flora, but before you do it requires proper seasoning. I expect from
now on anything you eat must first be topped with a dose of your own
come. If you do not do this I will have to start having someone else
season it for you, would you rather have Master James treat your food
with his come before you eat, no I doubt you would at this point.
I plan to have a get together for some other ladies I know with similar
lifestyles and I want to have you properly attired, you maid outfit
will not do for this we need something special. James said he would
give you a ride to the store and save you the trouble of getting a taxi
dressed like a woman, there is an outfit for you to wear when I send
you out in public in your closet now, had you already noticed it?
That denim skirt is cute but isn't that "your boyfriend gave me
herpes." T-shirt a laugh? You can't go out without make-up so I also
left you enough of that to get you started and some teen girl magazines
to give you some tips, better practice tonight so you don't keep Master
James waiting tomorrow.
Goodnight,
Mistress Jessica
Day 3
Dear Flora,
So much to talk about here. James told me that you balked at your new
outfit when you saw it at the store, that was completely without
reason; once you were dressed you looked adorable in your playboy bunny
costume, all my guests tonight said so. I know it wasn't so much the
outfit that you objected to but the bunny tail butt-plug that
frightened you, it was a lot bigger than your first one wasn't it?
James told me his analysis and I could not agree more if you are
frightened about having things in your pussy then we need to train you
more often to get past that fear so the new plug that James had you buy
and put in before you left the store will be in place for the entirety
of your working day from now on..
I am hoping after last nights show stopping finale you can appreciate
why I've been loosening you up. I have several different dildos for my
strap-on harness, do you remember how heavy the parcel you brought from
the shop was on the day you arrived? That is what was in it. A
harness for me and all those dicks for you, the one I took you with
last night was the smallest of the lot. You did make such a noise as I
took your pussy virginity, that was why I had to give your mouth
something else to do, that big cock you were gagging on was one of my
larger dildos but not the biggest. After I finished fucking my bunny
several of the other ladies there expressed an interest in buying you
off of me, don't worry I would never do that but June and I did agree
at next month's get together we are going to swap toys. You will
belong to her for the whole day so she can help you get ready and I
will be playing with her boy Mike. He has never been in a dress before
either so it'll be fun to introduce him to our feminine world, just
like I've been doing with you.
Sincerely,
Mistress Jessica
Day 38
Dear Flora,
It is hard to believe it has been a month already, and you are coming
along so well. I hardly feel any resistance when I grab your hips and
pound my thick rubber cock into your pussy, that is except for my
thickest dildo, but we're working on that aren't we Flora?
I had so much fun last night I simply adored reading your detailed
description of your day with Mistress June, all the things she bought
you were her gifts to you, isn't she so nice. I can tell it wasn't
cheap to get your hair dyed and those weave extensions are top quality
too, you do look so good with that thick curly mane of deep red hair,
but you better learn to properly take care of it. A shame it hides
your pretty new earrings, maybe once they've healed will get you some
nice big easy-girl hoops.
I would not have thought you had the nerve or the body to pull off that
wet-look latex minidress, but I guess halter-tops are good for not
revealing the fact that your breasts are only a couple bags of silicone
in a bra; so many other girls are that way too, they just have theirs
implanted.
I had fun transforming Michelle, he made quite the french maid didn't
he, but Michelle wasn't like you, it was quite obvious he was a guy in
make-up and a dress. Over the last month and a bit you have become
quite adept at walking in your heels, your demeanour has become very
ladylike, I am very proud that you take this process so seriously
Flora. I suppose how thin you've been getting on your sissy-chow diet
helped a fair bit. I wonder which of you has it worse, Michelle can be
easily spotted as a man in drag, you can pass but for you the
humiliation of discovery might be more, Michelle can claim he is too
much of a man to masquerade as a woman, but you are not so much of a
man as that.
Did you know Michelle didn't even read you at first? When we ordered
you to start making out he thought he was getting lucky with a woman,
that was why his hand drifted up your leg, are you glad we stopped that
action before he found your bulge?
Still he saw it when the two of you were getting fucked side by side, I
hope June wasn't too rough on you she's never taken an ass before, her
positioning was so great, taking you on your back with your feet over
your head, I think I came when she had you jerk yourself off all over
your face. Maybe I should take that photo of your come-covered
slutface and set that as my phone ID picture of you. Would you like
the idea that should you have to call me anyone I am with would see you
like that on my screen? Don't be a silly sissy I would not risk
embarrassing myself like that.
In Satisfaction,
Mistress Jessica
Day 66
Dear Flora,
These parties with my friends are getting to be the highlight of my
month, I am a bit disappointed I didn't have anything new to show off
with you my little sissy, aside from how pretty and slim you've gotten.
Everyone is so impressed with your flat little belly, tiny waist and
how well you walk in your fuck-me heels.
I'm going to have to have your maid's uniforms taken in, so tomorrow
that is another trip to the mall with Master James, and he has a very
special surprise for you too. I want you to put on that frilly ruffled
denim miniskirt and the pink baby-tee I bought for you, the one that
says 'panty boy' on it in glittery purple writing. I wouldn't want
anyone to mistake you for a girl after all, you aren't good enough to
be a girl, you're just a sissy. Maybe you best leave out breast forms
too, just in case.
When Master James arrives I want you to tell him you have so many
pretty panties you just can't choose and ask him if he will pick for
you. I can't wait to hear his description of your day tomorrow.
In Anticipation,
Mistress Jessica
Day 67
Oh Flora,
I was a bit disappointed in what I was told of your behaviour but
delighted at how things turned out in the end.
Did Master James really make you wrap your slut red lips around his
finger and give him a finger blowjob before he would pick your panties
for you? I am still giggling at the thought, especially from his
description of your face when he just thrust his hand into the pile of
panties in your hanging clothes organizer and tossed you the first
thing that he grabbed, a frilly red thong. Did you really expect a man
to carefully deliberate on underwear choice, silly sissy.
I also didn't expect him to hang around at the seamstress while you
were getting your maid uniform taken in, he's a real man and needed to
go somewhere manly as a counterbalance to spending the day with a
mincing sissy like you. He says you were so good at that point and
waited kneeling on the floor for him to come back as he had instructed
you. A shame you couldn't just keep behaving, but then again maybe I'm
glad you didn't.
Master James tells me you looked fit to wet your panties just
approaching the body mod parlour. Was it the way he did all the
talking and just left you standing behind him that got your resistance
up? The way he said, "My little slut here wants to get a pretty little
belly button piercing,"
I can't believe you tried to refuse! You just made it worse on
yourself didn't you? Master James wouldn't have bent you over the
counter and spanked your ass right there in the store if you hadn't
raised a fuss about your new piercing. I hear one of the other girls
in the store commented on the base of your butt plug, thongs aren't
really good for covering those sorts of things are they? And she even
asked to help with disciplining you, how did it feel having Master
James hold you to the counter while a sixteen year old girl you had
never met before spanked your ass with your Master's belt.
I quite agree with Master James, a reminder of who you are was in
order, you'll never forget again will you? Not with your new vines and
roses tramp stamp tattoo it even says Flora Allyson Grant on it, so if
you forget who you are in the future, anyone can just look at the small
of your back and tell you.
So between your new tattoo and your new piercing I hope you don't toss
and turn in your sleep Flora.
Vindicated,
Mistress Jessica
Day 89
Dear Flora ,
It has been three weeks now your tattoo should be pretty much healed
time to show it off. You have been a particularly good girl lately
you've earned yourself quite a nice little bank of wages, I think it's
time you bought yourself something with them. Now we don't want you to
spend all your money, I know how sissies can be with their money so we
will give you a budget, I think $100 will suffice, and I want you to
get as close as possible to that, in fact I think I might punish you
for every dollar in your purse at the end of the day, not having a
receipt means I will count the money as still in your purse so better
hold onto them. Of course I need to approve all your purchases so I
want you to take your cell phone with you. If you wish to buy
something I want you to send me a picture of it. Master James won't be
accompanying you but don't worry the price of the taxi won't come out
of your spending money.
Have Fun,
Mistress Jessica
Day 89
Come now Flora,
Your shopping trip is starting off so disappointingly. At least you
were smart enough to not ask for male clothing but all the things you
asked for were completely inappropriate for you, a Tom Clancy novel?
Call of Duty for your laptop? Seriously? I think you need to think
about things more carefully, go to the nail salon get them to give you
a set of gel nails chose a really girly colour and decoration. When
you are done that I want you to go back to the same stores you were at
and think, how can you make your earlier choices more appropriate?
Mistress Jessica
Day 89
Dear Flora,
I am glad to see you managed to think things through a little better.
Swapping that ugly violence filled game for Cooking Mama was a great
choice and I definitely Approve of '50 Shades of Gray' that is an
appropriate book for you to be reading. Those new earrings! Are those
darling dangling hearts covered in pink rhinestones? adorable, I hope
you put them in right away. So I see when you got home you still had 5
dollars in your purse. I think you probably could have found something
else to buy for that I wonder if you desired to be punished? I
preparation for tonight's party I want you to go out back and cut 5
nice branches off of the willow trees, a little thinner than your
pinkie finger and roughly two feet long. Remove any smaller branches
and smooth the shaft as much as you can. When you are done that set
them in the bathtub with just enough water to float them.
see you tonight,
Mistress Jessica.
Day 89
Dear Flora,
I'm not sure whether to be disappointed that you were such a noisy
little bitch last night or not. The squeals and screams that came out
of your pretty little mouth were such a distraction when all I wanted
to hear was the sound of those willow switches you cut on your soft
tender ass. But if you hadn't been so noisy I wouldn't have had to gag
you by stuffing that big thick dildo into your mouth. That took it
from an annoying distraction to a delightful addition, hearing you
choke and gag as you tried to cry out but that mouthful of cock stifled
you. After the third switch finally broke I could tell you wanted to
spit the cock out, you wanted to have your mouth free to scream, maybe
even to beg for mercy, but you are a smart little bitch and instead you
soothed your pain by sucking harder on that dildo. I've been told by
several of my friends that watching your cheeks and throat work on that
cock, sucking with fervour as tears smeared your mascara down your face
was quite inspiring. Finally after you felt the fifth and final switch
break against our ass I watched the exhaustion in your form as you let
yourself go limp on the bench.
Wasn't it nice of Master James to rub antiseptic cream on your ass?
There were a number of places where I had broken the skin that needed
to be soothed, and it was fun watching you squirm as a real man grabbed
and fondled your buttocks. He is such a powerful man, such a real
alpha male that at times even I feel just a little submissive to him,
but these feelings are faint and seldom.
Tonight you have seen the beginnings of what will happen when you
displease me, best you avoid it in the future.
Sleep Soundly,
Mistress Jessica
Day 94
Dear Flora,
Did you notice last night how many of my friends commented on your
lovely new decorations? Of course that was why I had you serving me
all night wearing only a bra and panties. Oh the scene you caused with
Warren, Master Warren to you, was decidedly not entertaining. He was
only calling you by the words spelled out by your initials miss Flora
Allyson Grant, for you to get defensive and insist you are no fag was
unnecessary and embarrassing for me as your owner.
Fortunately for me Warren felt I was adequate in my punishment of you.
After the beating I lay on you earlier in the week it did not surprise
me you could take the assortment of paddles and belts I had with me. I
wonder if you might even enjoy the sting of corporal punishment, maybe
that is why you are such a bad girl so often when around men. If this
trend continues I may have to find new ways to punish you.
Be a good girl now,
Mistress Jessica
Day 129
Dear Flora,
I am conflicted after last night, I tried so very hard to get you to
misbehave, it would have given me an excuse to punish you. Still I had
my fun the things I made you do just waiting for any type of back talk
were a load of fun. Mistress June commented how cute you were on all
fours wearing nothing but your bra, panties, garter-belt and stockings,
and of course a leash and dog collar. I might take her advice and get
you a puppy tail butt plug if we do that again. Watching puppy lick up
the coffee I spilled on the floor gave me a bit of a ladyboner I'll be
honest. I wonder if you still have marks on your back from the girls
who used you as a footstool while getting their heels tied.
Also I'm not sure if you were aware, the panties that were slipped over
your face for over an hour? Let's just say the only pussy that was in
them was you. I'm sure you've noticed in the past you are not the only
sissy at these parties. Maybe I might have gotten a reaction from you
by telling you that you were sniffing ballsack sweat that entire time.
Also I may have to start looking for a new dong for my strap-on since
even my biggest slides right on up your sissy pussy now. I wonder if
you can take my fist.
Proud to be disappointed,
Mistress Jessica
Day 133
Dear Sissy Flora,
I have some very special plans for you tomorrow, I wish I could be
there myself but I am due in court. I have to help a woman take her
absent husband to task for his financial obligations to her which he
has been neglecting. Maybe I will show her how to really get the most
out of her ex like I do, and often into you as well. Since I can not
be there Mistress June and Lady Thunder from our monthly get-togethers
will be helping you, be sure you thank them both thoroughly. I'm sure
you remember Lady Thunder, she's the full figured one, the sort of
women you used to call all sorts of repulsive names. Yes her boy
Giselle is even prettier than you, do you remember how you thought he
was really a girl until saw her strip his panties off and rail his
asshole?
I know when you usually do your make-up you are not really subtle but
for tomorrow I want a very specific look for you so I downloaded you a
couple of tutorials here and attached them to this e-mail. Oh but
forget the pink lipsticks they use I love the look of your super glossy
ruby red lips so use that instead.
Hmm are they both called "porn star" make-up looks? Well spoiler
alert, that is what you will be doing tomorrow. When you first came
here I said you weren't quite at the pretty sissy stage like the
sissies in the videos that play in your room 24 hours a day? Well
after tomorrow you will be. Make sure you sign these papers, you know,
more boring legal stuff., they are your release forms for any footage
you record tomorrow so I have ownership over the recordings and their
content.
Good Luck on your Big Day,
Mistress Jessica
Day 140
My Precious Porn Star,
I got the videos back from the editor today, you will be seeing them
over the coming weeks as they have all been added into the regular
rotation of the files playing on your TV. I wonder if you will notice
right away when one of yours starts to play or if you will just blend
in with all the other whores begging for the strap-on cock.
You did such a great job of playing what the scenes called for. When
you were playing the innocent cheerleader, cornered by the girls from
the ladies football team you really conveyed distress at being spit
roasted between their pounding cocks.
But when you were the delicate virgin in your prom dress I truly
believed you wanted that cock that Lady Thunder had in the pants of her
tuxedo. I haven't seen you gag like that in a while, that was a lot
bigger than what you've worked with so far. She made it a present to
me, so you will be taking it again.
And when you were pretending to be a typical guy dragged out into the
middle of nowhere and forced to wear that Little Red Ridinghood dress
you must have been pulling that humiliation from the past because I
never see you acting embarrassed about dressing like a sissy anymore.
I liked the costume Mistress June was wearing almost as much as yours,
that furry bathing suit and wolfears headband was adorable. I think
she felt a little embarrassed too because she pounded you more
furiously there than any of the other scenes. Had you ever seen a
dildo shaped like a dogs dick before? Apparently there is a company
that makes them, and more than just dog. I will have to place an
order, watching your ass swallow that big knot was almost frightening
and I can not wait to do it myself, maybe while you have a fake horse
cock in your mouth.
If the knot on the dog dong didn't convince me you could take a fisting
the next scene I saw did. That alley set is uncanny, it is an exact
replica of the alley behind the studio, right down to duplicating the
graffiti. You nailed the streetwalker strut and watching you get on
your back on those boxes and take two dildos in your ass at the same
time, just wow babygirl. my wrist is thinner than the combination of
those, it would just be a matter of getting the widest point of my hand
into you. Soon.
How did you enjoy the first blowjob you have had in over four months?
I can see you didn't want to come from it but couldn't help yourself,
it felt so good didn't it? Well now you see why Giselle's name has the
word jizz in it, he is as good with cocks as he is with clits. Were
you afraid if you came you would have to reciprocate? That you would
be forced into a sexy sixtynine with your matching babydoll nighties in
pink and lavender sucking on each other's pathetic sissy cocks? Now
Giselle hasn't had anyone suck her cock in years, I wonder if she would
even know what to do?
And no sooner do I get these videos but tomorrow I have something even
bigger planned for you. I want something big for our October party in
a few weeks, and since Halloween is just a couple weeks after our party
I have got such an amazing costume for you, I can't wait for you to see
it. There is only one problem, it is very revealing, and I want that
something special for you to wear it. I have made this appointment
long ago and now it is time. You will be seeing a cosmetic surgeon
tomorrow and I am getting you the biggest set of implants that are
offered right now. Sadly the truly enormous ones are Polypropylene
which hasn't been legal in more than a decade. I don't think I would
want to see you with something cartoonish like an O cup anyway, but we
should be able to get you upto a C, maybe even a D cup.
So excited,
Mistress Jessica
Day 140
James,
This is the only time I will ever call you that again. I had expected
when you read my last e-mail you might want to enact the exit clause of
our contract. I had hoped you would surprise me but alas. Before we
make this official I want to review a couple things with you.
You e-mailed me. You contacted me, wanting to make it upto me, wanting
to do anything to get my forgiveness. I can not forgive easily your
abandonment. Everything I have done to you started off as revenge, but
I think I am turning you instead into something I can treasure. You
promised you would do ANYTHING I asked, now you are walking out on your
promises again.
I suppose now the only thing I will have to remember you by are the
videos from last week. I suppose since I own those I might put them on
a couple websites, I just need to decide if I want it to be a pay site
or if I want them to be free for anyone with a search engine. Maybe I
will put red ridinghood, your scene with Giselle and the streetwalker
scene on some paid site because those are the premium videos, the rest
I might spread like seeds to the wind to advertise the three.
This is not a threat, I don't have to threaten anything, I have signed
release I don't need your permission to do whatever I want with them.
So I guess it is time for us discuss the financials of your exit
clause. I have been calculating your wages at $25 a day so to date you
have $3,500 minus the $100 you spent on your little shopping trip. But
per the terms of your exit clause you forfeit your wages, so in fact
you owe me $100 for the advance you took on those non-existant wages.
But really that is change, literally a penny on the dollar. Because
your exit clause also states that you retroactively owe me for 140 days
room and board. The contract dictates that it will be calculated based
on comparable services, well as it happens there is a bed and breakfast
in California that features a BDSM theme, which is essentially what you
have been experiencing, they charge $250 a night, literally one hundred
times what you would have been earning, so that brings the total you
owe me to $35,100. If you can pay me that then you are free to walk
away, but I know you cannot because I've seen your bank balance, I've
had your mail forwarded to me, that was part of the paperwork you
signed before you came here. Oh before probably would have been a good
time to tell you, the storage unit you put all your stuff in, something
happened with the paperwork, only the first payment cleared, you had
ninety days to make payment before the locker went up for auction, That
would have been about three weeks ago.
So when you leave here you have nothing but the wallet in your pocket,
and no pocket to put it in, remember your guy clothes went in the trash
when you were standing on my doorstep in your frillies. I won't be a
total bitch though, I'll let you take one outfit with you, which one
should I chose? The outfit you wore to the mall the first time? Maybe
for symmetry the outfit you were wearing when you arrived on my front
door 4 months ago? No, I will send you away in more than your
underwear. I know, your everyday outfit, you can walk away with the
french maid uniform on your back.
Let me know if you want to go ahead with your exit, otherwise be ready
tomorrow morning to leave for your appointment with the cosmetic
surgeon.
Remember I Own You,
Mistress Jessica
Day 141
Flora,
I imagine you are still feeling a little nauseous from the anaesthetic,
I can hardly wait to see your new titties. I hope the presence of
those bad girls reminds you where you stand. There really is no
getting out for you anymore, not until your year is up. At that time
you can walk away if you think you will still have any desire to be
anything but my bitch. You will even have $9,000 in your pocket, as
long as I don't decide to give you another shopping trip.
On that topic, being the considerate Mistress I am I am going to give
you a present to celebrate your new girls. In a day or two when you
are feeling upto it we will take a trip to the mall and I will buy you
a few new bras with matching sets of panties, and I won't even use your
money to buy them. I got you a new T-shirt to wear with your little
denim miniskirt. It says, "No, they aren't real, but thanks anyway."
Isn't that hilarious.
We can take your maid uniforms and have they retailored, good thing
you've lost more around the waist, which will help make up for the
expansion upstairs.
You're the Breast,
Mistress Jessica
Day 146
Dear Flora,
I got a call yesterday from our favourite seamstress she says your
uniforms are ready, the last few days of cleaning in just your
underwear are over. So you can throw on the same outfit you wore when
you dropped them off and taxi your little 38D self down there to pick
them up. And while you are there you can get a final fitting check for
your hot new costume for the pre-Halloween party.
You'll Look So Pretty,
Mistress Jessica
Day 157
Dear Flora,
It was a unanimous decision last night that your costume was the best
one there, I adored watching you strut around in your knee high boots
with the five inch heels, with your sexy red and black bustle skirt
down to the tops of your boots in the back but showing off your panties
in the front. the matching underbust corset left your new tits on open
display, except for the nipple covers, you were such a sexy burlesque
dancer, one of the girls suggested a place I could have you start
taking lessons in how to actually do burlesque dancing, I look forward
to seeing that.
The bag of clothespins around your waist was another fun game which
even you weren't aware of the ramifications of. All of the other
guests knew though, Each person got one clothespin, they could either
stick it on your new breasts or reach down into those crotchless
panties you were wearing and clip it onto your cock and balls. Were
you glad more people chose your breasts than your cock and balls? I
don't think you will be for long. Whichever body part got fewer votes
will be getting punished. If it had been your breasts I would have
gotten you nipple rings to go with your new titties. But your breasts
were the star of the evening, you only had four clothespins downstairs,
two on the shaft and one on each ball. That means the gift certificate
you won to Lilith's Garden will be spent on a brand new chastity cage.
On the good side this means you won't have to come on your meal every
night anymore. Don't worry, I will not have anyone else come on it for
you, I may just start treating it with a sprinkling of my own urine
instead.
Have a Boobiful day,
Mistress Jessica
Day 170
Dear Flora,
I have some exciting news for you, starting in two weeks and going
every Wednesday night and Saturday afternoon you will be attending
Burlesque classes for four weeks to master the basics. Don't worry,
you will not be alone, three of the submissive girls, and Mama Tiger to
my surprise, have all signed up too, and Lady Thunder has signed up
Giselle so you won't even be the only sissyboy there, and with the
girls I think you might even be sissier than Giselle now, at least
whenever she doesn't have a cock in her mouth.
You can wear yoga pants and a sports top, I wonder if your cage will
make the bulge in your pants even more pronounced, but at least it will
keep you from getting a hardon once all the girls start doing their
sexy moves.
Still you have two weeks before that is a concern, I have more
immediate plans for you. This year, Halloween is on a Friday so many
bars will be having Halloween parties the whole weekend. I have picked
three bars, one for Friday, one for Saturday and one for Sunday and you
will be going in your sexy Burlesque costume, just with a couple
adjustments. Your bustle skirt included this optional satin miniskirt,
I decided to leave it off for our party but for a night at the bar it
is essential, also you should wear a regular pair of panties
underneath, no-one needs access to your little prisoner here, wear the
red thong you wore when Master James took you to get your tattoo and
belly button piercing. Now since your cage might create a bulge in
your skirt I have a solution, I will leave you a new butt plug with a
chain attached, a very short chain which will clip to your cage and
pull your weenie back between your legs where it will not show.
The rest is fine, yes even your breasts being uncontained by anything
other than your nipple pasties. I know people at all of these bars so
I have already checked the rules. I will give you fifty dollars each
night and you are not allowed to come home with anything. It would be
too easy for you to get in and out in a hurry if we didn't have any
rules though.
First Rule: You are only allowed to buy alcoholic drinks, no pop, and
no food.
Second Rule: You may only tip between $1 and $2 for each drink
Third Rule: You can offer someone a drink by asking him (it must be a
him) "Buy you a drink, Handsome?"
Fourth Rule: You must enter any costume contests the bar is running and
must stay till the end.
I trust you will remember what happens if you come home with money left
in your purse, but I may have to improvise since the branches on the
trees have lost their sap and would break easily.
Party Hard,
Mistress Jessica
Day177
Consolations Flora,
I enjoyed reading your description of the Halloween Night festivities
very much. I can only imagine the looks on the faces of all those guys
who had been feeling you up and grabbing your titties all night when
you got called up on stage as first runner up for best female costume.
I am proud of your honesty in correcting them and telling them that you
are not a female, letting all those guys know that they had been
feeling up a fellow man. Of course this disqualified you and cost you
your prize but I think it was worth it to have such a dramatic coming
out in front of everyone.
I have to commend you on your sharp money skills you managed to come
home with not a single dollar in your purse, well done. I was hoping
to catch you with at least a dollar or two in your purse at the end of
the night, each night. of course when I mentioned I knew people at the
bar I didn't mention at this particular bar I know the bartender, and
he told me how you did it. Ordering water and tipping on it to get
through the last once you could no longer afford a proper drink. I
will allow it this time because I did leave that loophole, but for the
next two nights I expect you to play fair, you cannot tip more than the
cost of the drink in the case of free drinks of drink specials where
the drink costs less than $2.
My friend also tells me you were sloppy drunk by the end of the night.
I hear one of the bouncers had to stop you and give you back one of
your nipple pasties because it fell off and you didn't even notice that
you were just walking around tit out for everyone to see. Not that the
pasties cover much of your boob but it is an important distinction
between nipple covered and nipple exposed.
I wonder if you passed out in the taxi on the way home. I wonder if
the taxi driver pulled over somewhere and jerked off to those big
beautiful boobs of yours while you were out. You don't have any
strange tastes in your mouth this morning do you? Oh yeah you are so
used to the taste of semen that you probably would even notice someone
else's. Oh don't drive yourself crazy thinking about it Flora, I am
only teasing you, surely nothing like that happened.
And just think you still have two more nights of these sorts of
parties.
Pace Yourself,
Mistress Jessica
Day 178
Good Morning Flora,
Did you have fun last night? I suppose you know now that Tiffany, the
waitress at the club you were at was my friend. While many people
would have wanted to verify your claim when you made a point to specify
that you were signing up for the men's costume contest, but only
because she knew that you are my property did she chose to verify it by
sticking her hand up your skirt. She was intrigued by the feel of your
penis cage.
Wasn't it nice of her to lie to them saying that your boobies were
fakes that had been glued to your chest? Maybe you owe her a favour
some time in the future. If the judges had known your boobies were
implants they might have chosen to disqualify you, men do not have real
breasts after all, only girls and sissies like you have them. and you
would not have been able to win the contest if you had been
disqualified. who would have thought you would win a $250 cash prize
for showing everyone your pretty legs and your beautiful boobies? Now
since you could barely drink $50 worth without getting sloppy there was
no way you could have handled six times that amount. I'll bet all that
money was hard to get rid of but of course I know it was, Tiffany told
me all about the fun of watching you go up to men and offer to buy them
a drink with the phrase I told you.
I'll bet some of them were pretty reluctant to accept from you, given
that they had just seen you win best men's costume so they knew what
you keep in your panties. After all, what straight man would want a
sissy like you coming up to him and hitting on him, yes it was my
intention to make it look that way to anyone who didn't know you were
being forced to say it. Although I also heard about what happened to
you after you offered to buy a drink for one guy you had already bought
one for.
How was he, when he grabbed the sides of your head and rammed his
tongue down your throat? How did it feel having him pull you against
him and grab hold of your ass? Did you feel his cock against your
belly? Did he get hard? Maybe you might have even got hard if your
cock cage hadn't kept you locked up and soft.
Did you really thank him? Oh my, I am so proud of you sissy Flora, I
didn't even have to tell you to do that, but I would have if I had been
there. Maybe tonight you will have another man want to have his way
with you, and maybe you won't be able to stop him.
Keep on Partying,
Mistress Jessica
Day 179
Dear Flora,
Oh my, was I mistaken last night, was that club not having a costume
night? well of course they weren't it was already November 2nd, who
would still be wearing their Halloween costume. How embarrassing that
must have been for you to be the only person there still dressed up all
silly. And it was no accident, by the way, that you were at a gay bar
last night. Sure some of the guys there were so gay that even the idea
of breasts put them off, but many others loved the idea. I imagine
they were all thinking about looking down at you between your titties
jerking your cock as they rammed theirs into your sexy painted red
lips. Or picturing you sitting into their laps, their cock
disappearing up you dirty little sissy pussy as they reached around you
one hand on a booby and one hand on your cock.
I guess it is a good thing both your ass and your cock were locked up,
the only hole of yours that was really at any risk last night was your
sexy little mouth. I offer you congratulations on managing to keep
that virginity intact though, at least yet.
I was particularly impressed you had no money left in your purse when
the taxi driver carried you inside, after all that club was having a
special, anything on tap and all mixed drinks were just $2 every Sunday
after a holiday, and so that meant you had to have drank nearly twice
what you did on Friday, but guess what Flora, I know you didn't drink
that much, My bartender friend told me you only ordered 9 drinks. At
$2 each, even if we add a $2 tip per drink that only comes to $36. You
would have had 14 dollars left, did you try to throw the money away
thinking you could fool me, or did the taxi driver maybe empty out your
purse? You know what, I don't care what happened to the money. I am
going to punish you as though you had $14 left, and in fact I am going
to punish you double once for the money you didn't spend and once for
losing the money whether it was through incompetence or deceit.
I do hope you don't enjoy sitting down because you may not be doing
much of it after next weekend.
Disappointed,
Mistress Jessica
Day 185,
Dear Flora,
Yesterday was a big day for you wasn't it? Your first class in
burlesque dancing. Had you even seen it before? Did you make the
mistake of thinking it was little more than stripping? Oh no sissy, I
hope by now you understand it is more about the performance than just
the body. It is a story you are telling, and it is about comedy.
Fortunately you have it easy in that regard you are already a joke. I
mean just imagine what everyone you used to know just a short 6 months
ago would say if they could see you today, wouldn't they laugh at you
in your silly french maid uniform, manoeuvring flawlessly in your
highest heels being careful to not have your big bouncy boobies pop out
of your top as you bend over to retrieve something flashing glimpses up
your miniskirt in the process? Can you imagine what any of your other
ex-girlfriends would say if they could see your cock now, locked in a
cage and covered up by the girliest of panties?
And then of course there was the party, watching your face as I
explained my plan. I was going to punish you for the $14 you didn't
spend by choosing 14 implements and the 14 dollars you lost by giving
you 14 blows with each. watching your pretty little mind wheel as you
did the math, yes 196 blows is what I rained down on your lithe little
body last night.
First there was the flogger, a good simple way to begin, it gets the
blood flowing to the surface and believe me, it makes the following
punishment easier to take. If you don't believe me we can start off
without it next time. After that came the leather belt, Master James'
leather belt in fact, the very same one you had applied to your pretty
ass in the tattoo shop.
The ping pong paddle was the first of many paddles you would face in my
wrath, I kept a pretty rapid volley speed going didn't I, but it seemed
fitting to me. After that I brought out the first curt implement, a
standard bamboo cane. I let you lay there, hearing the swish as I
swung it through the air, remembering the sting of the willow branches
you'd had before. Once I started swinging it was clear this didn't
hurt any less.
The second paddle was the more standard wooden spanking paddle, the
type you see frat boys holding in movies, I wonder if any of them know
what it is like to really put one to use. I would see the jarring
impact making you rock forward a little bit on each blow, kind of like
watching someone get fucked doggy style. And after that I loved seeing
the relief in your eyes when I picked up the flogger again. Even
better was watching that relief fly away when I turned it around and
tapped my palm meaningfully with the big ball of leather that makes up
the handle, it is as hard as a ball of wood, isn't it Flora?
But another flogger was next, marking the half way point, my rubber
flogger. You really screamed when I delivered that first blow, I had
been just waiting for a reason to ram another one of my big fat rubber
dildos into your mouth to gag you. I had to a giggle a bit, this was
hardly the first time you've taken rubber to the ass and rubber to the
mouth at the same time but this was a little different. To begin the
dark side of your punishment I picked a neat little number you have
probably never even seen, it was certainly hard for me to get my hands
on. It is a carpet beater, used for the old days when vacuum cleaners
weren't what they are today, you would take your rug out and hang it
over your clothesline and do to the rug what I did to your ass last
night, do you think I managed to beat all the dust out of you?
Then it was a nice leather slapper, it looked like a flyswatter didn't
it? I didn't show you the other side which is decorated with small
metal nubs between the holes. I gave you seven without the metal then
seven with. And back to paddles, another wood one, but this time even
bigger with three speedholes drilled through it, just the thing to cut
down wind resistance and let me get faster blows.
By this point I could hear you blubbering, even around the dildo in
your mouth. It reminded me of all the nights I spent crying myself to
sleep, missing the feeling of the life growing within me that was no
longer alive. Maybe that was why I went harder on you with the next
two implements, I bet you were probably expecting a riding crop at some
point, it is one thing that even those who are not initiated in the
lifestyle of BDSM are familiar with. By this point I know your ass was
plenty tender but it needed just a little more. Don't feel bad about
not knowing what I was hitting you with until you saw it, no-one has
ever recognized my meat tenderizer on feel alone.
The last two implements confused you at first. After beating your ass
with so many things that pinkie thin fibreglass rod must have not
looked like much, but had you ever heard of bastinado before? Who knew
you could make someone howl the way you did just by such a simple tool
applied to the sole of the feet. I don't know why you cried so much,
after all that punishment was typically used for women and children who
were jailed. I wiped away those tears and showed you the last
implement after taking the dildo from your mouth, you seemed relieved
again when it was nothing but my bare hands, but I saw a caution in
your eyes, you had by now realized I was not going to make anything
easy for you.
I haven't seen that sort of defiance in your eyes in a while as I did
when my first open palmed slap landed on your cheek followed by a
backhand to the other side. I loved commanding you to look at me after
the third blow when just kept your head turned the way it had gone
giving in to the force of my slaps. Was it humiliating being slapped
across the face like that after everything else I had done? At least
that was the end of last nights torment, I hope for your sake that you
don't earn another punishment before next month's party as enjoyable as
I and the other guests find them I am sure you don't agree.
Stay Cheeky,
Mistress Jessica
Day 199,
Dear Flora,
Oh tomorrow is a big day, 200 days that you have been here, serving me
and I have something special in mind for you, it is another video
session, let's get those beautiful titties of you on film so you can
watch how they flop around while you get fucked. I will be there this
time but will only be in a few of the scenes, mostly ones that require
two women for you to service, I have a couple special guests to take
you through the other scenes. One of them I think you will like but
one of them I think you will not. Remember how I said you would have
to do something nice for my friend Tiffany from the bar, the one who
helped you get into the costume contest that you won? Well tomorrow
you will pay her back, she will be in all of your scenes, including one
that she laid out all the details for herself. She is not new to porn
herself but is looking to branch out into new types, which is why the
scene she planned will be going on her subscription fansite.
And just think, that is the guest I thought you would like, now I will
give you a choice of who the other guest will be, I have someone in
mind but if you refuse we could always have Master James come on and
fuck you instead.
You are so funny Flora, I can see you shaking your head even as I write
this, well don't worry I'll give you another choice. Remember the day
of your first video session how I could not be there because I was in
court? Well I did show that client some of the pictures of you and
told her what I had already done and about how I planned to get you
implants. She was intrigued and wanted to see when they were done,
after seeing photos of you at Halloween she even asked to be in a
single scene with you, again one of her own design, you may call her
Goddess should you need to address her. The reason you might not be
jumping at the chance to be in a scene with her is I recall the rude
and insulting things you used to say about bigger women and she
certainly is bigger, you know how your dress size is a size 10? I
don't know if you ever noticed that with any of the things I have
brought you, well Goddess is twice that number, a dress size twenty.
She probably weighs in the neighbourhood of 250 pounds, but I'm sure
even that is preferable to a man.
If I am wrong and you would prefer Master James shove his python (that
is what I call it, the man is huge) down your throat and up your ass in
every scene just let me know by tonight.
Lights, Camera, Action,
Mistress Jessica
Day 201
Dear Flora,
I will bet you just came home and collapsed in exhaustion after the day
we had yesterday. I was pretty tired myself or I would have written
you right away. I am eager to get the edited videos back so they can
be inserted into the rotation of your 24/7 sissy porn feed. I swear
pretty soon there will be as many videos of you getting fucked as any
of the other beautiful sissy boys that get fucked on there now, and you
are far prettier than most of them.
I enjoyed getting to strap-on that some dog cock shaped dildo that you
played with last time. Did you think I was kidding about getting one
shaped like a horse cock? You were almost like a snake watching your
mouth open wide enough to take it in, although there was no way that
would fit down your throat, it was all mouth action. I could tell
you weren't expecting it when Tiffany pulled the horse cock out of your
mouth and it started spraying that horse jizz all over your face, there
was so much of it, you looked like you had dunked your head in a tub of
yogurt. Don't worry though, that was all it was, watered down yogurt
to get the consistency of cum, not real horse cum,or even human but I
know you were worried.
After you got all cleaned up and your make-up redone, we had several
more scenes to film, I loved watching you sit on Santa's lap, wasn't it
nice of Lady Thunder to find that Santa costume with her big fake
beard. You made such a cute little santa's sexy helper, after all
Christmas is only a month away, you looked so lovely bouncing on her
lap, that big thick dildo sliding in and out of your ass as you did all
the work fucking yourself on her, your skirt sometimes popping up as
you rode giving glimpses of your own locked up little treat decorated
with a ribbon flower like a present. It wasn't by accident I chose a
strapless helper dress for you, it was also just a bit too small, I
wanted to make sure we got that shot of your tits popping out and
bouncing up and down as you rode the cock.
What was the next one we filmed, was it Tiffany's scene? I'm pretty
sure it was. As used to high heels as you are you had never even seen
ballet heels before had you Flora, they were a struggle even for you to
walk in, was it helpful to have Madam Tiffany there with her carbon
fibre cane to correct you if you faltered or slowed down too much? I
don't know if it was but it made things entertaining. The ballet boots
were bubblegum pink and made such a great accessory for your pretty
pink tutu. I know it hurt a lot more to be caned across the point
where your thighs meet your ass than across the ass itself, I hear
caning aficionados call that 'the sweet spot' because that is where it
hurts most. Tiffany told me she is adding a version of your video to
her free previews, a version that shows the caning and the ballet
boots for a few minutes right upto where you beg her to be allowed to
sit down for a minute and she brings out that chair with the monster
dildo Lady Thunder gave us affixed to the seat. if they want to
actually see you work that huge thing into your ass until your but
cheeks touched the seat they will have to subscribe to her page. I'm
sure you will get lots of hits for her. If this gets popular she may
film some more scenes of her dominating you, you could be a regular
little porn star, and of course any money you earned would be added to
your wage account, but at least for now you are working for free. I
guess that means for now you are not a porn star, just a slut who gets
filmed being fucked.
I love the look of you in your babydoll nighties, especially now that
we get the visual of your boobies through the gauzy material. I liked
seeing you face on the floor, ass in the air with Tiffany working your
ass with that strap-on, such a great position, and once you were warmed
up, like you hadn't been warmed up by a whole day of this, she started
lubing up her hand. I knew after last video session that you could
take a fist up your ass, and her hands are not much smaller than mine
so I imagine this might be something I could do to you whenever the
desire hits me to. I was so turned on watching your hungry little
fuckhole swallow her hand, I can't wait to watch that one back.
Finally after watching all those other scenes Goddess was ready for her
scene with you. It all built up to that final position which is what
she first envisioned, with you on your back, wearing your maid uniform,
as she straddled your face your head between her thick thighs your face
being smothered with her juicy pussy. Her holding your legs under her
arms so that your asshole was open for me to fuck your ass. since it
wasn't at a good angle for a strap-on I just had to make use with a
handheld dildo, I like the control I get that way but it doesn't feel
as visceral as grabbing you by the hips and pounding you that way.
Goddess covered well on film but afterward she was so embarrassed by
what happened, apparently her ex-husband had never gone down on her and
in fact never given her an orgasm, she had no idea she was an orgasmic
urinater and that when she comes she goes as it were. What a position
for you to be in when she found that out with your mouth being
smothered by her. I told her it was okay and that you drank my pee
every day, which is true but I didn't tell her you've never had such a
big dose at once.
Don't be Pissed Off About Being Pissed On,
Mistress Jessica
Day 216
Dear Flora,
Today was your last burlesque class, by now I've been told you girls
each have a solo dance ready, as well as a big group number, well guess
what before the play party this weekend your troop will be putting on a
show. I can't wait to see it. But after that we have a special event,
both you and Giselle are going to be dressed so pretty in your
frilliest, sissiest lingerie and you are going to have a peg race.
You probably have never seen one before so I'll tell you what to
expect, there is a bench with six wooden pegs sticking up from it.
Each one is taller and bigger around than the one before it, don't
worry, they are lacquered so there will not be any splinters. You will
each have a big bottle of unflavoured edible lubricant, but you can
only touch the pegs with either your ass or your mouth. I suggest
getting a good mouthful then get the peg as deep in your mouth as you
can, once you feel the peg is slick enough you may straddle the bench
and lower your ass on the peg, once your ass meets the bench you can
call for a judge to verify you have taken the peg and count to ten,
then you can progress to the next peg. The first sissy to take each
peg in order is the winner.
Let me explain just how much you want to win this contest Flora, the
winning sissy gets a blowjob from the losing sissy. Remember how I
said that no-one has sucked Giselle's cock in years? It isn't because
she didn't want it sucked, Lady Thunder has not allowed it, Jizzy is
the cocksucker not the cocksuckee, as badly as I think you do not want
to suck a cock is how badly I think she wants to get her cock sucked.
Good Luck,
Mistress Jessica
Day 220
Good Morning Flora,
I loved watching you last night, you were gorgeous and sexy but still
very cheeky doing your burlesque routine to Santa Baby. I still love
that outfit for you, maybe you should wear it for Christmas morning,
after all, it is only 11 days away. Master James and I both have
presents for you, and I ordered something for myself and paid for it
out of your wages, I'm sure I'll love the gift you bought me.
You continue to make me proud but disappointed with you on occasions, I
was so hoping you would lose the peg race but you were clearly
dedicated to win last night. I suppose after everything you have taken
up your sissy pussy you had no real trouble with the thickness of any
of those toys it was just down to the length of the last two, I've
never seen you take anything that deep. I still got enjoyment out of
seeing Lady Thunder's face as you raced past her sissy who has been
getting fucked in the ass for years and you were virgin just over seven
months ago. Giselle looked so crushed as she gave you your victory
blowjob, I've seen her suck a fair share of dicks over the years but
never have I seen her so upset about it.
Maybe Lady Thunder will find someone to give her one for Christmas, but
i doubt it. The woman is a true sadist, if there isn't someone
suffering and being truthfully tortured she can't get off.
11 More Sleeps,
Mistress Jessica
Day 231
Merry Christmas Flora,
Master James had to take me off and give me a rough fucking, he got so
turned on watching you with your pretty face and sexy womanly body in
your cute little slutty santa's helper dress crawling under the tree to
get the presents at this back he had to do something about it with me.
Did you like your presents from Master James and I? I know you have
taken bigger dildos than the one he gave you but that one is special,
one it is yours and you may keep it in your room and use it whenever
you wish, or maybe it will it using you. But the more important thing
about that dildo is that it is an exact replica moulded from a cast of
Master James' cock, so when you deep throat it you are deep throating
him, and when you shove it up your ass it is his cock in your ass,
remember that. Since you can take that you could certainly take him
should I ever see fit to order you to do so, but so far I am enjoying
the game of giving you ways around it and watching you reach for those.
One time you may fail to reach it.
My present for you is also for you to use whenever you wish, many girls
consider a hitachi magic wand their best friend. use it on your balls
or on the base of your new dildo while it is in you and you might just
be able to ejaculate without removing your cock cage.
Thank you very much for the lovely necklace, the meaningful nature of a
key necklace delighted me so, and in platinum with all those diamonds!
It looks very expensive, I'll bet it must have nearly cleaned out your
wage account (here's a hint; it did!) Enjoy your new presents and
we'll have some fun soon.
Merry Christmas,
Mistress Jessica
Day 238,
Happy New Year Flora,
Last night was so fun, I love getting all dressed up in my fancy dress,
it is so slinky and shimmery, it just makes me feel so sexy, did you
notice I was wearing your necklace? No you didn't, did you? You were
just so concerned with you were wearing that you didn't pay attention
to anyone else. Big deal you were wearing a diaper, so were a dozen
other people last night. And just think most of the people there were
regular people not even our kink friends. None of those guys were
aware of the secret hidden in that diaper, you should be glad you
managed to hide the fact that you had wet yourself from them, I'm not
sure how they would have reacted to seeing your caged up little cock
when they went to change you.
All of you little babies were being fed special bottles full of beer or
champagne to get all you babies drunk, but also to encourage your
bladders so you could have to be changed. I saw how you choked
unexpectedly with the first sip on one of your bottles, that sure
wasn't beer or champagne was it? And want to know the most fun thing?
It didn't come from me or Master James but it did come from someone who
knew exactly whose bottle they were filling.
Happy New Year Baby,
Mistress Jessica
Day 247
Good Morning Flora,
I have made a special arrangement tonight for you at our monthly play
party, you will be on loan to Sir Eric, you know him, his submissive
Darlene is in your burlesque troop. Well as it turns out Darlene's
birthday is in a couple days so as a treat he wants to give her the
feeling of being pampered and having every single inch of her body
worshipped and licked.
That is of course what your job will be, if a Master was to lick his
girl it would be because he owns her not in her service, now that will
include the nice places like her pussy and her breasts, but it also
includes her asscrack, her armfits and her feet. every inch of her.
If he was feeling particularly mean he would fuck her first and spray
his spunk all over her for you to clean. I know you would hate that,
maybe even try to refuse but I think we both know in the end you will
do what you are told.
See you Tonight,
Mistress Jessica
Day 248
Bad Girl Flora,
I arrange what should have been a pretty enjoyable experience for you,
a few body parts not-withstanding. How often, even before you came to
serve me, did you get a lithe young body to minister to completely?
And what did you do, you insult her. Even she noticed you cringe away
when you got to her back. And then you proceeded to ask her all sorts
of stupid, insensitive questions about her brand. It is the mark of
her sir, engraved on her body even more permanently than your tattoo.
There are procedures to remove tattoos or they can be tattooed overtop
of if you find you simply do not like it anymore. Brands are burn
wounds and those are much harder to get rid of, there are skin grafts
but even those leave their own marks.
Since you were so nosy maybe next month I should leave my mark on you
again. Should you leave me in a few months when your term is up you
can get the tramp stamp removed, you can take the piercing out and your
belly will heal, you can even have your implants removed. Maybe some
time I will have Sir Eric brand you with a mark of my choosing.
Be Afraid,
Mistress Jessica
Day 282
Happy Valentines Day,
I will not be going to the play party with you tonight. This is a very
special day and I will be spending it with James, Master James to you.
Don't worry though I have made arrangements for someone to do things
with you in my absence. No it is not Master Eric, you will not be
getting branded tonight, that comes next month. Instead you will be
with my friend Wicked Wanda who has no-one to spend Valentines day.
She wants you to get all dressed up in a sexy red negligee and your red
thong panties and she is going to be dressed like cupid. She plans to
shoot you with her arrows, not literally though, Wicked Wanda is
awesome with a needle and she will be sticking her needles into you,
stabbing them through your skin and surface flesh. I think that will
be fun, I wish I could see it but James has such a lovely evening
planned for us.
Don't Fall in Love with Cupid,
Mistress Jessica
Day 300
Good Morning Flora,
It is scary that in just over two months you will be making your
decision, do you want to leave or will you stay and be what I have made
you. But save that decision for another day, today you need to decide
on a design for your brand.
Oh what is that, you thought I was only teasing you? Well we'll see
what you think when that brand touches your skin, if you believe it
then. As far as a design I have narrowed it down to these three; a
lotus flower, a female symbol or your initials.
I can just imagine if you leave here in two months, you going to the
gym and in the shower, turning your back to the big buff guys and them
getting an eyeful of the letters F.A.G. on your ass. Would he see that
as an open invitation, could you fight him off if he did, after sending
a year here slimming down, losing muscle mass, turning into a skinny
little bitch?
The female symbol would be much the same situation, walking around with
that they will want to use you like a female. If you went out to a
bar, you pick up some pretty girl, you take her home, take off your
ugly guy underwear and she lays eyes on the raised scar, marking you as
a woman. I doubt she would stick around to see how you actually
perform.
The lotus, while it is still a flower and therefor a reference to your
name, would be the least humiliating for you. Look at the intricacies
of it, though, there are so many lines and it would have to be bigger
than either of the other two. The bigger and more detailed design
would take a lot longer to brand and thus would be a lot more painful
for you.
You have until a week from this Sunday to make your decision.
Choose Well,
Mistress Jessica
Day 311
Good Morning Flora,
Oh I wish you could see your own face last night. Once upon a time
there was still enough man in you that you would have chosen the more
painful but less humiliating option, when you chose the female symbol I
was so proud. You looked liked a condemned man walking the last mile
as you approached his table, watching the small flame heating the metal
large metal ring which would be used to create the large circle for the
top of the symbol. I could swear you were about to cry when I
explained how it would be performed and how the top of the circle was
not closed because a closed circle brand could lead to the skin inside
the circle dying and scaring up as well.
It was necessary to strap you down so you would not thrash around as we
were trying to work, likewise the blindfold helped prevent you from
panicking as the hot metal came near you. And once you were blind
folded we opened up the tool kit and took out two additional but
necessary pieces of our game. An ice cube and a raw porkchop. They
say human tastes most like pork so it makes sense we would smell like
it too.
Then as Master Eric pressed the burning hot brand onto the porkchop I
pressed the ice cube against your ass. The body often has difficulty
telling hot from cold and when you see something hot then hear the
sizzle of meat and even smell the charring of meat, it is hard to
convince your brain that what you felt was cold and not hot.
I was pleased to see your dedication to obeying me, but also to seeing
the relief in your eyes when we brought out the mirror to show you that
your ass was still pristine. Oh what a fun game that was, although I
may still have the female symbol tattooed on you somewhere. Perhaps I
will save that for if you remain as my sissy after your year is up.
Playfully,
Mistress Jessica
Day 339
Oh Flora,
Last night was the last of our monthly parties that you will be
required by our contract to attend. Your term will end the day before
our next party. Sometimes it seemed we would never get to this point,
this is the time of your greatest decision. Having done anything and
everything I have asked to earn absolution for what you did years ago,
you have less than a month before you will be free to go if you
choose.
We will have a ceremony and at the conclusion of that ceremony you will
either leave here and we will probably never see each other again, you
if you choose to stay you will belong to me, truly and forever.
I will go into more details in the coming month.
Not Much Longer,
Mistress Jessica
Day 365
Good Morning,
Two doors lie before you. Today is the day your life goes one way or
another.
Tonight you will be brought to a special location and let into a room
prepared for you. There you will find two outfits, both tailored to
your exact measurements and Giselle and Darlene to help you dress.
They are forbidden to speak until the conclusion of our ceremony so
they can not influence your decision, even if you ask them. Your
choice of outfit will indicate your choice of where life will go from
here. Once you are dressed you will join myself and Master James in
the main hall. I will be there in my leather corset and black thong
panties with my thigh high stiletto heels and Master James will be
wearing his tight leather pants.
The first outfit you can choose is a very expensive suit, you will not
be able to do up the jacket right now, but should you get your implants
removed it should fit fine. This choice indicates your desire to
return to the life you had as James. Should you choose it we will both
sign the release portion of your contract on two copies, one for you
and one for me. Then both Master James and I will shake your hand. I
will give you the key to your cock cage. A car will be waiting for you
out front with the possessions you had on you at the time you arrived
and the balance of your wages account, just under $5,000. I am ashamed
to admit I misled you several months ago when you asked for your
release. There was a problem with your storage locker that much is
true, but what I did not tell you is that I dealt with the problem, all
your belongings are safely waiting for you. The car will take you to a
hotel where I will have a room waiting for you. I will pay for a plane
ticket home for you and if you want you can even see the same surgeon
who gave you your implants, he has agreed to give you a special
discount on having them removed.
That is your first choice. The second choice, which I hope you make,
will indicate your desire to stay here and remain my Flora Allyson
Grant, my pretty flower.
The outfit is a wedding gown, but a very special wedding gown. The
bodice and extremely flared ankle length skirt are both completely
sheer. The bustier and panties you wear underneath will be easily
visible. The sleeves are not sheer and are capped at the shoulder with
an exaggerated balloon style puffed shoulder. On your feet you will
wear a pair of white ballet heels with an 8 inch stiletto heel. if you
come down the isle in that outfit you will kneel between Master James
and myself, you will kiss my ass as I present it to you, then you will
turn and kiss Master James right on the bulge in his leather pants.
Both of these are a promise of how you would be using your mouth later
this evening. There will be no games no way out, choose this and you
will be sucking Master James' cock and eating my asshole tonight. but
before we go to the hotel room for all of that I will collar you, a
steel collar with white gold trim has been made for you and it will
never be removed if you pledge yourself to me.
Now the choice is yours.
Please,
Jessica
******************************************
"Good Morning Jessica, how are you today?"
"I am fine, thank you doctor, I feel so much better these days."
"That is good to hear, how do you feel better?"
"I just feel at peace, I think the journal is really helping. Writing
all the letters exactly as I wish I could send them to HIM."
"Is it therapeutic? That's good to hear. Now Jessica, I hope you
truly are recovered, you have been with us here just over a month, I
really hope you are ready to go home."
"Oh absolutely doctor, there will be no more problems for me."
"No more attacking people, no more throwing things?"
"No doctor, that is all behind me."
"It is fortunate for you that your co-worker agreed not to press
charges if you sought treatment."
"yes doctor, I am very grateful for him. I understand now just because
he has the same name as my ex-boyfriend, he is not the same man."
"And which name is that Jessica?"
"James, doctor. My ex was named James, and so is my co-worker, well
former co-worker. But they are very different men, I realize that
now."
"Very good, I see no indication of agitation or resentment when you
speak about James, that is a very good sign Jessica."
"Now I want to try adjusting your medication to a much lower dosage,
and if you continue to make this sort of good progress you will be
going home in no time."