My name is jester, i am 18 years old and i live in the west end of london. I was a student
studying Drama, Music and Dance at Oxford University and until recently i was your normal,
run of the mill, average guy.
THE PRELUDE
I had been away for six weeks studying and was on my way home looking forward to my
beautiful girlfriend meeting me off the platform. As the train pulled in at Charing Cross i
spotted her waiting for me and my heart skipped a beat. Picture this if you will, clad in
sexy pink hot pants with black leather heels and a small but revealing vest, it was enough
to make any male of the species pop their eyes right out of their holes. As i opened the
train door she beelined for me and nearly knocked me over, i was certainly standing to
attention i can tell you that. We made for the taxi rank and set off on the last leg of the
journey back to our west end flat, all the way back she was looking at me with great
curiosity and smirking every so often. "Whats so funny" i said with a smile, "oh nothing"
she smiled back "just something funny that happened earlier on today".
THE TEMPTATION
We got back to the flat around seven and we did the usual cuddles, how have each other been
etc etc had food, you know the usual stuff couples do when they havent seen each other for
a while. She then announced she had to go out for a few hours, she had a few errends to run
but she would see me later and make it up to me. Needless to say i was eagerly clock
watching.
I went in the kitchen to fix myself a snack when i noticed the dirty clothes hamper sat
next to washing machine. I opened the top and looked inside and it was full of her
underware waiting to be washed and i mean everything from a bra to panties to tights and
even a corsett with stockings. I spied through these items and looked at the clock, she
wasnt due back for at least an hour so what the hell. I had always been a secret
crossdresser and took every opportunity i could get to try on female clothing, my latest at
university was stealing my friends panties whilst she was taking a shower. I walked into
the bedroom and began to undress, i had settled on a pink lacey style bra with matching
panties and the knee high stockings. I slid on the bra and fastened the catch, then slid
the panties up my legs loving the feeling of the soft material against my skin. Then lastly
the stockings, they were like a touch of heaven, so soft, so smooth. I marvelled at myself
in the mirror even tucking my little friend back on itself so i looked flat.
I checked the time again she still wasnt due back for at least fourty mintues, so i pulled
on my own clothes over the underware and went to sit back in the front room. I did the
usual, watched some tv, stroked myself, played with my nipples when all of a sudden i heard
the front door open. "****" i thought, she shouldnt be back yet what am i going to do.
CAUGHT
I quickly threw on my trainers and pulled a jumper on hoping the bra wouldnt show through.
"Hi babes" she said "everything ok?" i must have looked slightly shaken but replied "sure
everythings cool did you get all your messages done ok?". She replied she had and that she
had brought two of her friends back who wanted to say hi. In walked Jen and Amy, now these
two were complete regulation hotties. Jen was blonde with a figure to die for and Amy was
brown and the same. "Hi Jester how was uni?" "fine, same stuff different day" i replied,
Jemma went off into the kitchen and my heart sank. "please please dont notice there
missing" i prayed, how would i explain to her that i stole her underware and am wearing it
right now. Jemma returned two mintues later looking a little confused but seemed happy
enough so i put it to the back of my mind.
Jemma looked at me and said "Jen and Amy are going to be spending the night their flat is
out of bounds at the moment due to flooding and they have no where else to stay" "but dont
worry" she added "you and me will still get our make up time" and with that she giggled,
slapped my ass and wandered off towards the bedroom. "you coming sexy?", both Jen and Amy
giggled at this, "Yes" i replied " i just need to goto the bathroom first". Jemma raced
back down the hallway and grabbed my hand saying "no you dont i havent seen you in six
weeks and im horny now". Meekly i allowed myself to be dragged into the room and she
started kissing me moving her lips around my mouth and neck. She pushed me back down onto
the bed, i tried to get up again making excuses about the bathroom but she was having none
of it. She was being oddly dominating which confused me as i was usually the dominant one
during our sex sessions. She moved my hands above my head still kissing my neck when i hear
a "click".
I looked up and saw my hands were cuffed to the bed. "What the hell are you doing??" i
exclaimed "relax baby" she replied "this is just to make it more interesting. She then
preceeded to cuff up my ankles as well but as she put on the last cuff she started staring
at my ankle with great curiousity. "Why are you wearing stockings???" she barked "er erm im
not i er" all i could do was mumble. She took my trainers off and just stared at the see
through stockings covering my toes, she then unzipped my jeans and pulled them down and
half screamed "What the fuck are you doing wearing my panties, again i could only mumble
unable to do anything in my current state. She then started to lift up my jumper saying to
herself "He cant be.....surely not" but i surely was she stood there open mouthed staring
at me in her underware.
REVENGE
Suddenly she got very angry and snarled at me "how dare you wear my clothing you perverted
little freak, you really think i want a sissy as a boyfriend" she went to her dresser and
pulled out a pair of scissors "im going to teach you a lesson to make sure you never do
this again". She started to cut down the sides of the jeans and up the sides of the jumper
and across the arms. She pulled the tattered clothing from under me now just wearing the
underware and stockings. "JEN, AMY" she shouted "CAN YOU COME HERE A MINUTE" i started
shaking "please jem im so sorry please i wont do it again please dont bring them in here".
Seconds later the door opened and jen and amy walked through, the both fell about laughing
at me handcuffed to the bed in Jemmas panties and bra. "Very sexy" exclaimed Jen, Amy even
came over and snapped the waist band of the panties. They then noticed how upsett Jemma was
and took her for a talk in the spare bedroom. "We will be right back" said AMY "now dont
you move anywere". They were gone for fifteen whole mintues and try as i might i couldnt
undo the handcuffs or even move.
Suddenly the door opened and all three of them walked in, Jemma had been crying and the
other two looked more serious now. "Right sissy" said Jen "we have had a talk and Jemma
here doesnt want to be with a sissy boy who wears girls panties. She has decided she is
leaving you and as you well know myself and Amy are lesbians and Jemma wishes to join us
in a three way relationship". "As for you we have decided what to do with you....as you
wish to wear womens underthings, and judging my your erection you are rather liking it, we
are going to completely feminise you and turn you into our own person maid". I looked in
horror at them, they couldnt be serious. "So i wore some female underware" i shouted "like
that warrants turning me into a girl". Jen walked over and slammed her foot straight into
my crotch, "I hate stupid little girly boys like you and its about time someone did
something about it".
Suddenly all three of them started searching around the room throwing various items onto
the dresser, i had to strain to see what it was they were searching for and my heart
completely dropped. There was makeup, hair straightners, perfumes, wax strips and the very
skimpy and revealing french maid outfit Jemma had worn for halloween two years previously.
They started out by plucking my eyebrows, they worked swiftly, for the amount they plucked
they might as well have taken all of my eyebrows off. I tried to struggle and again a swift
kick to the nuts subdued me, "If you stuggle again sissy i will cut your balls off" Jen
swung the scissors dangerously close to my face and i nodded in agreement. They then moved
off my eyebrows and preceeded to apply wax strips all over my body, and i mean all over
even my beard and parts of my pubic regions. After a few moments to let the wax set they
started ripping them off, i cried out in pain as each strip was removed. Evntually the last
strip was removed and i was rubbed down with a lotion that appeared to remove the last of
the wax. The stockings were then slid back up my legs "Hey sissy look down at your new
smooth body" i strained my head to look down and saw that i did in fact have no body hair
anywere, Jen then pulled down the front of the panties and i saw my pubic hair had been
fashioned into a heart shape. I started to cry, Jen slapped me and said "pack that in
bitch, there will be time for crying later, its now time for makeup".
I sat there watching them prepare the products, they seemed to be mixing it with something
which confused me as i had never seen Jemma do this with her makeup. Jen noticed me
watching, "This is a little technique i picked up doing drama classes, the makeup would
always run off in the heat of the lights and sweating." she finished what she was doing and
walked over with the makeup tray and started to apply foundation. After a minute or so of
coating my face she said "so what we do is we mix the eyeshow with a little superglue and
then apply it to your lids like thus". She dipped the brush in the tray and i saw the
eyeshadow was bright pink, it matched the panties, she then brushed it back and forth
across my eyelids and put the brush down. She then picked up some eyeliner and outlined the
lids, then finished it off with some mascara. "There we go" she exclaimed "sissy has
lovelly feminine eyes" i could see Jemma and Amy giggling at this. Jen then picked up some
hot pink lipstick and lathered my lips warning me if i moved what the consequence might be.
She then pasted some more glue over my lips and had me open my mouth until it had set.
"There you are your lips have such a nice shine to them now" i was red faced tho you
probably couldnt see it under all the makeup.
"Ok Jemma how far do you want this to go" jen asked "Er im not sure you know what f**k it
do what you think is best, make it hard for him to change back". Jen, Amy and Jemma went to
the corner of the room and started talking quietly. "Oh we couldnt do that" i heard one of
them say and they all started giggling. Jen walked back over and said "ok sissy we have
decided not only are you going to be our sissy maid but we are going to make you look like
as much of a girl as possible, and trust me once were done not even you will be able to
tell". Jemma handed Jen a pair of sillicon breasts and she started gluing them to my chest,
i started to struggle again and Jen grabbed and squeezed my penis making me cry out "im
sorry im sorry i wont move again please just let me go". Jen looked at me and said "oh we
will let you go but once we are done doing this, and trust me when we do untie you....you
wont want to leave anyway". Once she has finished gluing on the breasts she then started to
use foundation to blend them into my skin, working foundation all the way up my chest and
up my neck to blend in with my face. She then applied a little around the outside of the
breasts which i later found out meant they would stay looking blended in. I looked down
once she was done and saw that it did indeed look like i had a pair of real C sized breasts
sat on my chest. Jen then noticed that this had indeed turned me on and my penis was
struggling to be released from its lacey prison.
We have to do something about this, one its not very feminine and two it needs bringing
down a peg or two. Jemma said she would take care of this as a last present to me. She
started to lick her tongue up and down the shaft of my penis then inserted the whole penis
in her mouth. I moaned in pleasure and she moved up and down getting faster and faster
until suddenly i shot my load in her mouth. She removed her head and then came up to kiss
me. Not thinking i kissed her back when suddenly i had my own load of cum in my mouth. She
quickly backed off and clamped her hand over my mouth "swallow it sissy", i didnt have a
choice so i did as i was asked and swallowed my own semen. Jem then quickly started to dry
off my penis and with the help of amy started folding it here there and everywere. I
wondered what they were upto and all of a suddenly i felt a burning sensation in my crotch
area which got very painfull then dissapeared. "There" said Jen "now no one will be able to
tell you were even a guy". Worried i asked what they had done "Well if you push your balls
back up inside your body, then fold the penis back on itself, you can then fold the skin
the balls sit in over the penis and once glued it looks like a vagina, ok one with a large
clittorus but still a vagina".
I started crying again at this point and Jemma said "Well if you hadnt stole my panties
you wouldnt be in this mess would you" Suddenly Jen produced what i knew was a but plug,
she pulled the panties down and inserted it up my bum, she then turned on the vibrate
function which was very loud and made me squirm uncontrollably. Then out of the cupboard
Jemma produced a pair of her leather heels only these were huge, they must have been at
least 4 inches of heel and you might as well have been standing on your tip toes. "I dont
mind these getting ruined if you want to use them" said Jemma, Jen looked at them, looked
at me and said "I have an idea". She started to use lashings of superglue all inside the
heels and around the rims, she then slipped each one over my foot and then did the same
with the straps. Then lastly and finally came the maids outfit, they unzipped the back and
slipped it around me and zipped it up. They painfully spun me onto my side and ran a line
of superglue up the zip. This dress was the worst thing ever they could have put me in, the
skirt didnt quite cover the panties so you could see my pink crotch, the chest area had a
hole cut out so you could see my breasts, how was i going to get out of this thing and what
if someone saw me i was back at university in 4 days. Jen then produced a choker, it was
black and white and very frilly, again with the glue she attatched it around my neck.
The last things to be done were my hair being straightened, my nails being painted hotpink
and lastly a little maids bonnet tied around my head.....at last they had finished.
ADAPTING TO MAIDHOOD
I was un cuffed and for the first time in hours was allowed to move of my own free will. I
couldnt stand in the heels and the feeling of the breasts on my chest were so alien to me.
As i tried to walk i saw myself in the mirror i looked like a genuine female bar a few
small features like my nose which was distinctly masculin. Jen came up to me and told me to
put my hands behind my back, to which i refused and screamed "what the fuck have you done
to me you mad bitch, i look like a girl, im not a girl im a boy". She punched me straight
in the stomach which made me keel over onto the floor and then forced my hands behind my
back and handcuffed me once more. She then attatched a pink collar just above the choker
which had a lead coming off it. I was pulled to my feet once more and dragged by the lead
out of the room. I tried to resist but the heels were so high and the slippery laminate
flooring didnt help, no matter how hard i tried to stop i either slid along or lost balance
and tottered forwards anyway. I was so humiliated being led around the hallway, every step
i took made the skirt on the outfit rise up above my crotch, there was no way to hide the
pink panties i wore beneath. "Ok sissy" said Jen "you have two choice now, you either do as
we say and become our own personal sissy maid or i put you outside on the street with the
lead attatched to the lampost". I once again tried to resist and Jen started dragging me to
the door. "Ok ok" i cried "I will be your sissy maid just please dont take me out looking
like this". "Ok but before we start there is something you have to do wait here a moment"
and with that she tied the lead around the radiator and disappeared off into the front
room.
I could hear alot of giggling coming from the front room and seconds later they appeared,
un tied me and dragged me in. "Ok sissy we need a name for you first of all how about
Jessica?" Jen looked at me as if awaiting a response "My name is Jester not Jessica you
have had your fun now can you please let me go". This time is was Jemma who piped up
"Listen you little bitch this is your life for the moment either you accept it or we leave
you out on the street and who knows what sort of person might take fancy to a little sissy
thing like you". I thought about it for a minute and shuddered at the thought of the
perverted drunken men, who inhabited parts of this neighbourhood, taking fancy to me tied
to a lampost. I gave in "Ok fine Jessica it is", "Wonderfull" exclaimed Jen "Now to get you
used to seeing yourself like this and to calling yourself Jessica i want you to kneel down
infront of the mirror and read out what is on this card".
I knelt down as she asked and took the card and read "Hi there my name is Jessica, i was
once called Jester but my loving partner and her friends helped me become the sissy maid i
have always wanted to be. I love wearing my pink panties, i feel so sexy in them and i
never want to return to being the boy i once was. I want to be kept as a sissy maid forever
and be used as a sissy sex save, i will prove it to you by sucking a penis right now". They
had me read the card in the girliest voice i could muster with a lisp over and over until i
was able to face the mirror and recite the passage without aid. On the last go Jemma said
"I have a suprise for you sissy" i turned around and she was stood there wearing one of my
t shirts and a pair of my jeans. "Looks neat doesnt it....do you know what a strapon is?" i
looked fearfull as i did know what one was i had seen my fair share used in porn movies.
She unzipped the jeans and pulled out the most realistic looking erect penis i had ever
seen. "After you have recited that passage your going to turn round and suck this penis and
you better make it look realistic i have done it to you often enough so you should know
what to do". I stared with horror and tried to get up, to which Jen slammed her foot into
my crotch once more "This is your last warning bitch you try that again and your outside
and not our problem anymore now get on with it". Defeated i faced the mirror and read out
the verse trying to sound as girly and lispy as possible and then the penis was thrust in
my face. I hestated at first but i thought "fuck it if i do this it might satisfy them
enough to let me go".
I started moving my mouth up and down it, Jen tapped me and showed me a card which had
written on it "moan like a girl and act like your getting off on it". I started moaning and
rubbing the penis up and down getting faster and faster until Jen said "Ok we have enough
now". She went behind the mirror and pulled out a camera, my heart skipped a beat, "You
recorded that?". "Yes" she said "wana see" and with that she plugged the camera into the TV
and played back the last recording. They all laughed whilst i watched on in shame at my
performance which even i didnt think i was acting that realistic, then came the worst part,
Jemma thrusting the cock into my face. She was right she did look like a boy, the camera
was positioned so you could only see me and her lower half. "Just think what would happen
if i sent this to your university" she lauged at me "please dont please i will do anything
you ask please". She took the camera and left the house for ten mins, when she returned she
said "ok thats now safely in my car where you cant get it, we are going to untie you now
and any attempt to resist that video is going live". They uncuffed me and detatched the
lead "So Jessica are you going to be a good girl"...."Yes" i replied meekly. "Good i want
you to go fetch us some sandwiches theres a good maid". "Yes" i replied again, Jen grabbed
me and said "Yes what bitch". "Yes Miss Jen" i said, "theres a good girl off you go". I
stumbled to the kitchen my skirt riding up at every available opportunity and only now did
i become fully aware of the but plug, it rode around with every step making me squirm and
as for the heels i still had not got the hang of walking in them.
I prepared the sandwiches as asked and carried them in on a plate. Somehow in the time i
had been gone they had managed to get through a bottle of wine already "Oh thankyou jessica
how very nice off you, you know i could get used to having a sissy maid around" she smiled
at me and said "Jemma wants something off you". I looked at Jemma and suddenly her and Amy
started kissing and moving their hands down each others pants. "Jemma wants you to play
with yourself like a girl would whilst they have a little fun of their own and we want to
see it so drop your panties theres a good sissy". I lowered my panties and looked down, it
really did look like a vagina down there. I started to pretend to play with my clit whils
watching them, "act like a girl would jess" i started to moan and pretend i was really
enjoying it. Suddenly they stopped and Amy parted her legs "now your one of the girls i
want to see what your like in licking people out" by this point my penis was straining
against the glue and i was in alot of pain. Amy produced this black leather thing that
looked like a head restraint with large straps running off either side. She attatched these
around her waist and i was instructed to lean forward. My head was placed inside the
restraint and a third strap ran under her legs. Once this was tightened my head was pulled
in and my nose was resting on the lips of her vagina, my hands were once again cuffed
behind my back and my feet were cuffed to my hands. I was now balanced on my knees and
couldnt pull away if i wanted to. "Ok lick away and dont think of stopping your going to be
down there for a long time".
I started to lick away and after about twenty mintues my jaw was aching, Jen then uncuffed
my feet and lifted my legs up whilst Jemma slid a coffee table under me. My feet were
promptly cuffed to either side of the legs and my panties slid all the way down and the
plug removed. "Dont worry Jessica were going to let you know what its like to be fucked,
and with that Jemma inserted her strapon into my hole. I screamed out in pain at first
feeling every inch of my rear being stretched out, but that didnt stop her she pounded my
ass for what seemed like forever. "Oh" exclaimed Jemma "i think Amy has had a little to
much to drink" and true to her word Amy had passed out. Jemma removed the strapon from my
ass and then inserted what i thought was the plug but i was wrong. I realised immediately
what it was as it started vibrating and squirming around. She had inserted her rampant
rabbit dildo up there, she pulled my panties back up and said "dont worry babe the battery
will last until morning, me and Jess are going for some fun in bed now, dont you move and
we will see you bright and early". Jemma and Jess left the room and went upstairs, so here
i was completely sissified, tied to a table, penis on the verge of ripping itself appart,
vibrator in my rear and i was strapped face first into Amys vagina and i was stuck like
this till morning. Jemma popped her head around the door "I hope your ready for tomorrow
sissy, trust me your gonna be so humiliated....do you like diapers or sundresses...i think
we might like a little sissy baby girl for the day tomorrow". With that she left again
leaving me praying that this would all come to an end soon and just to add to it Amy's cum
was dribbling all over my face. Could this get any worse??
OK YOU GUYS DECIDED WHAT DO YOU WANT DOING TO JESS NOW.....PLEASE PLEASE PLEASE NO SCAT, NO
WATER SPORTS THIS IS A FORCED FEMINIZATION AND HUMILIATION IM NOT DOING ANY NAMBY PAMPY
BORING AS SIN STORIES OF LOVE AND DISCOVERY SO DONT EVEN SUGGEST THEM AS I WILL FLAME YOU
INTO YOUR GRAVE. "DISCOVERY" STORIES ARE BORING AND NOT HUMILIATING IN THE SLIGHTEST.
