Mommy s Dirty Sissy Slut part 1
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Mommy's Dirty Sissy Slut Part 3 free porn video
Mommy's Sissy Slut part 3 by dirteesissy
Please read parts 1 and 2 before enjoying this instalment.
Chapter 10.
The last hour and half had been the most unpleasant and painful of my
life. The cr?che nurses had a fully functioning dungeon in the back and
had taken great pains to have me sample each of the instruments of
discipline.
My bottom was not just red, but bruised and covered in welts. At the end
of proceedings, I was cleaned up and made up, before being led back to
reception. I could barely stand, but I knew that sitting down would be
agony, so I stood next Ella, as she smiled at my discomfort.
"Be sure to drop in any time, Odette. Me and the girls know how to treat
sissies like you, no coddling or messing around. Hooded and strapped
down, your diapers around your ankles and beat that horrid bottom till
you scream in pain and shame!"
I knew that I had passed out at one point, but I remember screaming for
all my worth. I got on my knees and thanked Ella for my punishment. I
began to lick her shoes in supplication, a sissy true.
"I see Odette has learned her place, Ella. I hope she was a good sissy
and didn't play up to much?"
Alicia and her confederates entered the room, shopping bags in hand and
took in the sight of me at Ella's feet. Ella told Alicia I'd been a
darling and she should feel free to drop me off any time she was at the
shopping centre.
Lisa took my reins and pulled me to my feet, before checking out my new
panties.
She pointed out the writing and everyone agreed I was a "DIAPER LOVER".
I nodded my head and everyone laughed at me.
I was led out in the shopping centre proper, heading for the main
entrance and the street beyond. It took some minutes again as the
shoppers once again stopped us to question my clothing.
More than one of the ladies present commented that there husband,
boyfriend or son, could benefit from being dressed as a girl. The males
that were with these particular ladies looked at me in fear as they
contemplated there future if they didn't book up there ideas.
After a deluge of sympathy for my sister's choice and many pitying
glances from the ladies, we left the crowds behind and headed for the
lingerie shop.
"Did you enjoy my sister's punishment, sissy? Is your bottom all red and
throbbing? Never mind it's time for you to try on some nice silky
lingerie! That will make that bottom feel much better won't it? Pretty
lingerie for a pretty little girly!"
We crossed the car park to a series of honks and catcalls from passing
drivers, but that was nothing to what happened as we hit the main road.
Within moments traffic was bumper to bumper, as the road users took the
opportunity to pour scorn on me.
I was called every name under the son as my ladies looked on with
amusement, but when they heard sirens in the distance, they quickly tied
my reins to the nearest lamppost and told me to join them when the
officers were finished with me.
The onlookers made a hasty retreat, as a Police van pulled up alongside
me and 2 officers got out. I recognised the first as the female officer
who had fingered my freshly fucked bottom, yesterday at the police
station.
The second was Sargent Jenny Collins who had sentenced me to my buggery
and who had taken satisfaction in my humiliating ordeal. I was quickly
frisked by the junior officer, before being untied from the lamppost.
"Well if it isn't the little sissy from yesterday. All prettied up and
causing a disturbance on the high street! I think you need to be taught
another lesson, as the last one seems to have failed. Let's get you into
the van and see to you, diaper boy!"
I was manhandled into the back of the van, after the Sargent unlocked
the outer door and the cage inside. I was quickly handcuffed facedown to
1 of the benches in the back and my diapers and panties pulled down.
The Sargent left to get something from the cabin and left me alone with
the Constable. She introduced herself as Louisa Lytton, she smiled at me
and asked what I was up to. I explained that I was on my way to get some
lingerie for a special occasion this evening.
When I explained that I was too shown off in all my feminized glory to
my Mommy and certain select friends of my sister, she looked astounded.
"I bet your looking forward to seeing your Mommy this evening, all
decked out in your best dress and some lovely new lingerie underneath.
Not many sissies are lucky enough to have a sister like yours willing to
put up with your strange needs and desires!"
I blushed and thanked the Constable, just as the Sargent reappeared. She
passed a cane to the P.C. and told her to make me cry.
My bottom was already a sea of fire from my previous punishments today,
so as I was caned, I quickly began to blubber.
After the 13 stroke, I was uncuffed and made to kiss the cane that had
stroked my behind. Constable Louisa Lytton helped me back into my diaper
and panties, before they sent me on my way.
Chapter 11.
I entered the shop to a round of applause from all the ladies present.
The other ladies there consisted of the owner, Miss. Belluci and her
assistant, Emily. I'd been in her more than once buying my own lingerie,
but telling them it was a gift for my girlfriend.
I could tell at once that Alicia had explained my history to the owner
of the shop and her assistant, and were gleefully waiting my arrival.
"Your right Alicia, he does look divine in that dress! A sissy through
and through, if he'd only told me of his predilections, I could have
spared you the effort of feminizing her. I've got 3 sissies at home
right now, in French Maids dresses, doing my housework and waiting for
my return to be punished for my pleasure!"
I begged Alicia's leave to lick Miss. Belluci's shoes and she consented.
She was dressed in the most figure hugging red dress, her magnificent
bosom almost spilling out. Her legs, as always, were covered with the
most sheer of silk stockings, white, they were clearly held up by a
garter belt. Her dress made that obvious.
I knelt at her feet and began to lick her shoes in adoration. They were
white pumps with a 3" heel and I thought they looked delightful. I
looked up into her eyes, as she asked what I needed today.
"My Mother is meeting this sissy later for the first time and I want her
to look her best. Something sexy, but girly, maybe some Rigby & Peller
or Agent Provocateur. You see I promised that I'd dress him in his
favourite outfit from his favourite sissy story, a Bridesmaid, but you
only come out once to your Mother, so I've bought him the most lovely
brides dress to wear. Nothing but the best for my sissy brother!"
I turned away from the shoes of Miss. Belluci and thanked my sister with
genuine love. At that moment I felt the most honest and joyful emotion
for my sister.
We spent the next hour with me naked in front of these delicious woman,
trying on item after item of the most yummy lingerie ever. Bras,
Basques, garter belts, panties and hosiery, all were tried and in the
end Alicia decided to buy the lot.
"After all you'll need plenty of undies in the future. I've been talking
to Mrs.
Gilmore about the option of returning to work next week, as you'll need
an income to pay for your addiction to female clothing. She said you can
replace Lolly as her secretary and she can have your old job. How about
it Lolly? Fancy bossing this sissy around at work?"
Lolly was eager to agree and as we left the Pretty in Pink lingerie
shop, multiple bags over flowing from my grasp, she began to describe in
detail what I was to wear and do as her new secretary.
I was to wear the shortest of skirts and the tightest of blouses, to
show off the lingerie I would be wearing underneath. At the beginning of
each day I would submit to a underwear inspection in main reception and
if I was deemed to have not put in the desired thought to my outfit, I
would be disciplined on the spot.
All regular work would be carried out first, but if there's time
permitting I should offer to help any of the other women around the
office.
I would be allowed only 1 toilet break per day and must ask her for
permission to go. All lunch breaks will be supervised and I could only
eat the leftovers from everyone's lunch time meals.
At the end of the day, I would be appraised on the quality of the day's
work and if I had been unsatisfactory, I would be servly punished. As I
couldn't be trusted to make my way home safely on my own, Lolly
suggested that Lisa might collect me and babysit me until my sister
returned from work.
"That sounds perfect Lolly. I'll contact Mrs. Gilmore and set up the
particulars. Home time girls! Let's get ready for tonight's
festivities!"
I was dragged across the road and bundled into Alicia's car. Tonight my
old life would finally be over and my new life as a full time sissy will
begin.
Chapter 12.
When we arrived at Alicia's home the preparations for tonight began in
earnest.
I was sent to the kitchen, whilst the ladies went upstairs to bath and
prepare themselves. I spent the next hour and a half cooking and make
the house tidy for the party.
So busy was my workload, I didn't notice when Lisa entered the living
room. She called out to me and I turned to a vision in black. All she
wore was her undies and her high heels. Her face was made up like she
was about to star in a porno flick.
She wore a black lacy Basque decorated with flowers made of red lace.
Her panties were barely there, just covering her sex, before becoming a
string that disappeared in between her bum cheeks. Silk stockings were
held up by garters dangling from her Basque.
"Put down that cleaning stuff it's time to ready you for this evening.
Come with me and prepare yourself. A sissy bride for Mommy!"
I was led upstairs and quickly disrobed, and my butt plug removed before
being led into bathroom. Inside Lolly was running a bath for me, bubbles
were frothing up and it smelt so feminine. Lolly wore even less than
Lisa, just a pair of red panties and red push up bra.
Covering her was a rubber apron protected her body and a pair of latex
gloves covered her hands. She stopped the water and had me stand next to
her a she smeared my body with hair removal cream.
After waiting a few minutes, she had me enter the bath and proceeded to
scrub me head to toe, taking special care to fondle my cock. She then
has me get on all fours before soaping up her fingers and fingering my
gaping hole.
"That butt plug has done the job perfectly. Your wide open and ready for
anything! Let's get you out, dried and made up."
After towelling me dry and adding perfume to my special places, she had
me enter the bedroom once more. Lisa re-joined us, her outfit complete.
Dressed in a tight calf length skirt made from black taffeta, she made
my jaw drop in surprise.
She wore a red silk blouse that was half unbuttoned, revealing her
cleavage and the top of her Basque. A little pill box hat was perched on
her head with net half covering her face. She looked like she was ready
for anything and my cock rose in apprceation of her look.
"Have to take care of that in a bit, after your make over. Hop on the
bed and let's varnish your nails!"
For the next hour Lisa made me up look like a bride. Subtle tones and
carefully applied colours made me look almost angelic. From the choice
of the blush to the application of false eyelashes nothing was left to
chance. So when Lolly re-joined us as Lisa was finishing, she
congratulated Lisa on a job well done.
Lolly had opted for a more fetishistic outfit. A simple latex dress, but
the rear had been cut out to show Lolly's magnificent behind. She wore
no panties and by the looks of it no bra either.
Lolly's first task was to get rid of my hard on by the simple act of
flicking my balls until it shrivelled. Once this was accomplished she
took a black silk stocking from the bed and covered my tiny cock in its
sweet carress. Next she took a pink silk ribbon and tied it around the
base of my penis.
"Locked away for the day, sissy! If you dribble any of your nasty come
in to pretty panties we'll be able to see very easily. Let's get some
stockings on you, boy!"
Lolly took great care to roll up the sheer white silk stockings. First
the left leg and then the right, they felt like nothing I'd ever worn
before. The shoes came next, an open toe sandal in white leather with a
diamante encrusted bow.
Next came a sheer white Basque decorated scallop white lace, it was
boned and panelled to give me a slimmer figure. As I was squeezed into
this exquisite item of lingerie I asked Lisa where Alicia was.
"Lolly's been helping her get ready. Her outfit is a surprise for you
later.
You'll cream in your panties when you see how she's dressed! Speaking of
panties, it's time for yours!"
A matching pair of white thong panties appeared and were soon covering
up my cock. Garters were threaded through my panties before being
attached to my stockings. They felt taut and incredible as Lisa pulled
the tabs tighter.
Lolly left the room for a moment and returned with a big white box. When
she opened it a bridal petticoat spilled out, goose bumps appeared on my
arms and legs as I took in the sheer size and scope of my wedding
petticoat.
"It's got 2 hoops to make it stand out and 13 layers of tiered net.
Everyone's going to be able to hear you coming from miles away, listen
to it rustle, Odette. Lovely isn't it, but let's get it on you dear!"
I stepped into the petticoat and almost swooned with pleasure. The net
tickled in between my thighs and I my cock rose in my silk prison.
Lisa tied the ribbons around my waist, petticoating me, before taking my
hand and rubbing it all over my body so I could feel every little piece
of my silk and lace outfit.
I knew the moment had arrived when Lisa swung open the wardrobe doors
and there hung a garment bag, waiting for me. Lisa unzipped the bag and
pulled out the dress.
It was made of the most exquisite off white tulle material was divine,
but what made it the perfect dress for me was the full skirt, I now knew
why I'd been dressed in such a full petticoat.
The bodice was shoulder less and form fitting, with tiny barely pink
roses sown into the material and diamante shimmering.
"Come on then, sissy. Time for your wedding dress!"
Chapter 13.
After I was helped downstairs by my 2 dressers, I was having trouble
breathing.
Each item of clothes seemed to be making me hyper ventilate and Lisa
took my gloved hands in hers, before lowering my veil.
She squeezed my hands and looked me in the eyes, a deep smile of
satisfaction on her face. She let go of my hands and took a bouquet of
white and pink roses from Lolly, giving them to me.
"It's time, Odette. Through that door are a few of your sister's
friends, I want you to enter and curtsey to all the ladies present. Come
on now, off we go!"
I opened the door and entered the room. I felt very shy and feminine, I
just hoped I wouldn't be ridiculed too much. Sitting in the living room
were 3 woman, all of who had seen me dressed before, but I'd never seen
them dressed in this manner.
First was my boss, Mrs. Gilmore, dressed like a sissies wet dream. She
had on red latex thigh high boots, a tiny pair of red latex panties and
nothing else.
She held a very fierce looking riding crop that she tapped against her
thigh.
"You look divine sissy boy! I could munch you all up, but that would
spoil the fun. Give us a twirl, girly!"
I twirled slowly as I took in the next of my witnesses today. It was
Lisa's mother, Chief Inspector Smith. She wore a full body rubber cat
suit, but it was made up to resemble a police officer's uniform. The
only thing out of place were the 5" stiletto's she wore on her feet.
"I've hearing all sorts of stories from my daughter and fellow officers,
so I thought it was about time I witnessed one of your displays. A sissy
bride about to meet his Mommy!"
The final member of the group was Lolly's sister, Ella. She'd dressed in
her old school uniform, but I had never seen such a blatantly sexual
costume. The skirt was so short her red silk panties were visible and
her stockings were clearly on display.
"Been looking forward to this all day. Time you showed the world what a
sissy you really are!"
I looked round for my sister, but Lolly informed me she would be joining
us presently. The doorbell rang and I heard Alicia's voice call out from
the kitchen.
"Answer the door for me Brother dearest, and be sure to greet my guests
properly!"
I headed to the front door, shame filling my heart, as I tottered on 5"
stiletto heels. Not the usual footwear for a 20 year old man, buy I
couldn't have looked less like a man dressed as I was.
I swished my way to the front door and curtseyed to the arriving guest.
I looked up into the face of my Mommy, she was smiling as she took in
the sight of a man dressed as a bride.
"Your sister has outdone herself this time. She told me she'd finally
caught you dressed in her clothes, but I didn't think she'd be able to
get you dressed as a sissy bride for your Mommy. Don't look so shocked
I've known for years that your nothing more than a pansy!"
I was in complete shock as, my Mommy, explained that she'd been laying
traps since I was 12 to catch me dressing in her clothes, but that I'd
always been lucky enough to get away with my shameful desires.
Mommy took my hand and led me into the living room full of women anxious
to meet her. She introduced herself to each of the ladies in turn,
before remarking she was a little over dressed for this gathering.
"Come here, son and help me with my coat."
I helped my Mommy remove her long coat, but I nearly died of shock when
I saw what she was wearing underneath. Or should I say what she wasn't
wearing. A pair of black hold up stockings and her stiletto heels. Her
sex was on full view to all present, as she flaunted herself.
"I'm dripping wet, son! I've been so turned on since Alicia suggested
that we expose you for the sissy you are, but this is the last chance.
After this there's no going back, you'll have to live like this until
the day you die! Think about it carefully, son. You have 60 seconds!"
I stood there wide eyed as every one of these strict woman watched me
make my final decision. If I said yes I would be committing to a
lifetime of humiliation and servitude, but in the reverse I would never
know the feel of silk and satin next to my skin.
In the end it was no choice. I bowed my head and offered myself to these
woman, mind, body and soul.
"Couldn't help yourself could you, eh? I think a nice punishment is in
order don't you, sissy boy? Ladies if you would be so kind, as to help
him with his gown and petticoat."
I was soon bent over the back of the sofa, my petticoat and gown over my
head and my panties around my ankles. I heard Ella whisper into my ear,
to get ready, but nothing could have prepared me for the agony I
experienced in the next few minutes.
A spanking hurts a bit, but it's the humiliation that really does the
damage.
With a caning, it's the agony of stripes crossing over each other and
making the pain twice as bad.
What my Mommy inflicted on me then was a whipping. She showed after that
each of the 8 prongs of the whip had metal balls attached to the end. I
took 16 of her lashes before I fainted, but when I woke my final
humiliation would commence.
Chapter 14.
I came round a few minutes later, only to find myself, hogtied on the
floor. My ankles and wrists were tied together, with my now panty less
bum on show for all to see.
I looked up to see Mommy and Alicia in deep conversation. My sister was
a mirror image of her ever youthful mother, but instead of black
stockings and heels hers were white. They looked down at me with utter
scorn.
"Time for you to pop your cherry, brother dearest. I see your hard in
your silk prison, but you won't be needing this pathetic cock. No its
time for you to get fucked by a real man!"
Stepping into sight was Brad from my office. He was buck naked and
sporting an impressive 7" cock, he was masturbating it slowly as he took
in my outfit and demeanour.
He grinned wickedly as he knelt down at my bottom and began to trace a
ring around my hole with the end of his dripping cock. Round and round
it circled, I felt sick as he took his time with his virgin bride.
"Here you go Brad, some lubrication for your cock. We sure don't want
you to be uncomfortable as you screw my son silly!"
My Mommy was rubbing her pussy juice all over Brad's cock, making it
ready for my deflowerment, but it was my sister who drove me over the
edge. She used her pussy covered fingers to lube my asshole, all the
while finger fucking her own pussy.
Alicia was sitting on my right and my Mommy on my left, as I lost all
reason and begged Brad to fuck my sissy ass. He winked at me and slowly
began to ease his cock up my virgin bottom.
I glanced around the room as I felt the first inch enter me. Each of my
tormentors looked on to my ultimate degradation with glazed features.
Lolly, Lisa and Ella were openly masturbating as Brad eased another inch
up me. Mrs.
Gilmore was busy strapping on a dildo, whilst Chief Inspector Smith,
unzipped the crotch of her cat suit.
"How does it feel, son, to be fucked like a woman? A virile man parting
your thighs as he enters your innermost place? Take it. Go on Take it
and show everyone here what a Sissy you really are!"
I was beginning to feel very full as Brad now had 4 inches in me. He
slowly drew almost all the way out before slowly, but powerfully pushing
deeper inside me.
Brad began to build a rhythm as he fucked me. In and out he took me in
the missionary position, my silk covered legs touching his broad
shoulders. I began to grunt as he got even deeper into my hole. I cried
out that I couldn't take anymore.
"Plug up that sissies mouth with my panties. None of us want hear his
useless cries for help!"
Ella threw her bright red silk panties to my sister, who quickly stuffed
then into my mouth. That taste was unmistakable, Ella's panties were
dripping with her juice. I began to suck wildly, as Brad continued his
assault on my virgin ass.
He once again withdrew his cock from my bottom, before ramming it back
in as hard as he could. For the next minute or so he pounded me as hard
as he could, before withdrawing completely. Mommy laid a hand on his arm
and stopped him from entering me again.
"I can't let this carry on anymore. Brad's cock is obviously too big for
Odette's hole! Maybe if we encourage the sissy boy here to stretch a bit
more maybe Brad can really open him up!"
The suggestions came thick and fast, Ella suggested a caning to
encourage my compliance, Lisa suggested that I should be made to lick a
toilet seat to put me in the mood, but it was my own sister, Alicia, who
noticed my raging hard on.
"I think this sissy bride needs a milking, while Brad fills his bottom.
A nice rub to make his bottom open and take every inch of Brad's cock!
Now who would like the honour of helping out Odette?"
Both Lisa and Lolly quickly raised their hands and I began to nod my
head yes, but Alicia said I wasn't ready for such attention from pretty
girls. I would soon start thinking I stood a chance with other girls and
forget my place.
Mrs. Gilmore offered her services next, but Alicia said she should carry
on fucking the Chief Inspector. She screamed her thanks as she orgasmed
all over my bosses rubber cock.
"Wait I now the perfect choice, the only woman here who only wants the
best for this sissy and the only one who can make it into a real good
for nothing else sissy, my Mother!"
Mommy looked at Alicia with shocked eyes, but when she looked down at my
tiny hard cock, twitching in its silky prison, something came over her
face. She bent down and whispered in my ear if I wanted this.
I looked at all the watching faces, as I tried to make this decision to
become a total pervert. I shivered in shame as I sealed my fate by
nodding, but Mommy said that wasn't enough.
"I want you to beg me to milk your tiny cock, while your fucked like the
slut you are! I'm no touching that maggot until everyone here knows what
you're really capable of!"
Alicia pulled Ella's panties from my mouth and sat me up into a more
sitting position, as time slowed down and every ear strained to listen
to my humiliation.
"Mommy will you please rub my tiny cock, please? I need Brad to fuck me
silly, but his cock's too big for my virgin hole. I promise to be a
slutty sissy bride for everyone's amusement, but I need some help from
my Mommy. Please milk me?"
The hole room erupted in laughter as I debased myself. Lolly told me I
was nothing and I deserved every one of my punishments for being such a
pervert.
Alicia put me back into the best position for Brad to fuck me and
whispered in my ear, that she was very proud. I asked why and she said
she always knew that I'd be a cock hungry whore like my Mommy.
"Mommy just loves cock, she doesn't care who's, she just loves to fuck.
I remember watching when I was a young girl as she fucked all comers,
taking each spurting cock into her willing pussey! You're the result of
one of those couplings, sissy! A bastard boy dressed as a bride and
taking cock just like his Mommy!"
Brad pushed his meat back into me much more easily than the first time
and quickly began to fuck me hard. Mommy's hand began to search for my
cock as the ladies that had started watching from the seats, came ever
close so as not to miss a single moment of my milking.
"Where's your cock son? I can't find it under these frilly petticoats!
Oh wait I've found it, let's just pull off this stocking and see what's
stirring!"
I almost shot my load there and then as Mommy began to pump her hand up
and down my shaft. Slowly at first, but quickly building up pace. Ella
shouted out that I shouldn't be allowed a release until Brad had come.
Alicia agreed and quickly explained the rules to me, but I was on
another planet now as the twin sensations of Brad buggering me and Mommy
milking my cock.
"You know son you shouldn't be ashamed about the size of your cock, I
mean many boys have smaller ones than this. Not any over the age of 6,
but cocks like Brad's don't grow on trees!"
It was at this moment that my bottom opened up completely and Brad's
invading monster sunk all the way in. I cried out in surprise and Alicia
asked what was wrong. I answered nothing, as I felt Brad pull all the
way out of my bottom before plunging all the way back in.
I began to sob as Brad fucked me like the slut I was. Each thrust robbed
me off my remaining manhood and I wanted nothing more than to feel like
this forever. I turned to Mommy and thanked her for this moment.
"My pleasure, sissy. I think it's time for Mommy's big girl to milk!
Brad looks like he's ready to come so off you go, girly!"
I felt Brad's cock begin to twitch and he thrust one final time, deep in
my hole, before emptying his load into my waiting ass. It was all too
much and I came right then as Mommy pumped my tiny cock.
I wilted for a moment, before coming round as Mommy forced her come
covered fingers into my willing mouth. I licked and licked as all around
me the women in my life orgasmed.
The end. (For Now.)
Rowan
- 31.07.2022
- 41
- 0
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