Prisoner in the Mall
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Prisoner Or Maid free porn video
Olga eyed the new inmate with a sly smile. She slid her baton over his
slim body.
"Have they told you what to expect?"
Norman cringed. He stared back at the uniformed woman who seemed to
enjoy his fear.
"Yes," he breathed. "I'm not sure I can take it?"
As her beady eyes ran over his body he examined her with a warmth that
surprised the grey-haired matron. She was a big woman and her brown
uniform shirt strained against her massive breasts. Her heavy stomach
was held in check by a broad leather belt that glistened in the dim
cell's light. Her brown boots creaked as she moved.
Norman swallowed nervously as the woman's breasts touched his chest.
Their eyes met. He experienced a weak-kneed desire that puzzled him. But
she saw his excitement.
"Like big girls do we?"
He shivered. "I'm sorry..."
Her smile made him squirm. Her double chin wobbled and her dough-like
face became pink. "Don't apologise. I like girly-boys."
They walked along a brick-walled corridor and he became cold with fear.
The talk in the holding cells had been of rape and brutality.
At first he thought they'd made a mistake.
"This is the Women's section," he said with a smile.
Olga just stared at him and then replied, "Would you rather spend the
next five years of your sentence in a man's prison? You want to be raped
by strangers?"
He frowned, hope filed his mind.
"You mean I have a choice?" he asked in disbelief.
She smiled, a knowing, wicked smile. "I've read your file. You were an
actor, a good one ... you once played the part of a woman. " She stated
flatly.
His face went red. "But that was just a play," he answered.
She grinned. "But you were very attractive ... could you do it again ...
in here?''
The question hung in the air ... once more they stared at each other.
Once more he felt that incredible sexual attraction. And suddenly he had
an idea of what she wanted.
He licked his lips and whispered, "What? What exactly do you want from
me."
Olga wasn't shy. She knew this youth had no chance of surviving in a
male prison.
"We have a program for the women prisoners - we trained them to be
domestic servants, to help them get employment when they are released.
If I can convince the new Governor that you are willing to be trained,
you could stay here."
Norman couldn't believe it. He had a chance to escape the torture of a
man's prison - but could he really pass as a female?
"And how would you convince her?" he asked warily.
Olga sighed and pushed him into a white-walled room. "Be totally
passive. Humble. Wear something that demonstrates your willingness to
learn."
His mouth dropped open and he went a deep burning crimson. "You want me
to - to wear skirts?" He asked faintly.
Olga closed the door. He heard the lock turn. "Not at first - but that
is the impression you must give her. I suggest a blouse, velvet
breeches, ladies shoes and hose - we need to show you could be a
houseboy or something!"
He licked his lips. He suddenly realised that his fear of being
feminized almost equalled his fear of being sent to a man's prison!
"But what if ..... I mean she might want me to wear skirts, you said so
yourself?" he asked.
The woman moved close. "Would that be so bad? I could look after you.
Better than being in prison."
"I'll do it," he muttered.
The clothes weren't so bad. The soft sateen blouse made him blush, and
the sheer nylon stockings made him nervous - but the pants were OK. As
she screwed his feet into shiny buckled shoes he agreed with Olga, this
was better than prison.
It was only as they waited outside the Governor's office he became
really scared. His knees buckled as the door opened and a uniformed maid
ushered them inside. Norman watched as Olga whispered into the
Governor's ear.
He glanced sideways at the two uniformed maids. They were grinning. He
felt his face grow hot.
"Thank you Olga. That will be all."
Olga winked as she left him alone facing this grey-haired woman. Mrs
Black was more like a Headmistress than a prison governor he thought. He
felt her eyes run over his costume.
"I run a very special training program," she told him. "I turn
aggressive felons into submissive and obedient servants. Olga believes
you would benefit from such a course. Do you know why there are no male
prisoners on the course?"
He shook his head. "No Ma'am."
"Take a good look at Sally," she told him nodding towards the maid on
his left.
Norman obeyed. The girl was pretty even in the ridiculous maid's outfit.
"Sally is wearing a uniform," she told him. "Her clothing tells the
world that she is submissive and obedient. It tells everyone she meets
that she is a servant. But more importantly it tells sally that she is a
servant! Sally accepts that uniform because she has decided that her
future is in domestic service. She will never again be aggressive. Sally
will submit, sally will obey!"
Norman felt a cold chill settle over him. He knew what she was going to
say next.
"Men find it difficult, impossible even, to submit. Aggression is
normal, obedience unnatural. But occasionally we meet a man who is
capable of surrendering his masculinity. Take you for example. You have
willingly dressed yourself in a servant's clothes - does that mean you
are willing to serve? We can control your aggression, we can even force
you to be obedient - but what we cannot do is forcibly remove your
masculinity. So - I have one question for you Norman. Are you prepared
to legally and officially change your status in this institution. If you
agree you will be entered into the training course as a female prisoner.
You will be, not Norman, but Norma."
He felt the blood drain from his face. His knees trembled and he felt
light-headed. He could feel their stares. He tried to think. Twice he
opened his mouth. But words wouldn't come out.
The older woman smiled sadly. "I understand - take him away girls."
"No!" he gasped. Taking gulps of air he tried to compose his words and
thoughts. "It isn't easy but Olga was right. I can do it. I want to do
it."
Mrs Black looked doubtful. "Are you sure? Once you enrol you will not be
allowed to change your mind - or your sex."
He met her eye. "I'm sure Ma'am."
She shrugged. "In a minute that door will open and a Doctor will examine
you. If I show her your application forms she will accept you as female
and you will then enter the main part of the prison complex. You will be
given prison clothes. Female clothes. And you will wear them. If I
don't, she'll send you to the man's prison. Make up your mind."
"What do I sign?" he asked firmly.
Sally produced a typed form. "You sign as Norma."
And he did - for the first time he signed his name as a woman.
The Doctor was a thin, pale woman with a mean mouth. She raised an
eyebrow when she saw the man facing her.
"He's rather pretty - but he's not a woman," she said calmly.
Mrs Black glanced at Norman. "Is she right Norma?" She whispered, 'are
you a man? Have I made a mistake?"
Norman held his breath. Both women watched him, both enjoying his fear.
"My name is Norma," he told them softly. "And I'm a woman."
His face grew hot as they both grinned. And hated himself!
"Take him away sally - tell Olga I want to see Norma when she has been
processed."
::
After congratulating him on his 'success' Olga shoved open the double-
doors leading to the main complex. Norman viewed the long table
anxiously. A second warder was piling prison clothing in front of him.
"Two cotton underpants, two cotton bras, two waist slips, two pairs
nylons...."
Olga nudged him with her baton. "Pick up your clothes Norma."
In a daze he picked up the clothes noting that the uniform consisted of
a plain black dress that buttoned down the front. His dress! He cringed
as the second warder smiled at him. "Two uniform aprons - one waist, one
bib!"
He cringed as he held the pile of clothes - his clothes!
Olga drew a thin curtain around them at the end of the room.
"Hurry up. The sooner you get into your uniform the better!"
He shook his head wearily.
"I can't do it. I'm sorry."
She prodded his chest with her baton. "You don't have a choice. Get
undressed!"
Norman couldn't move.
Shaking her head with resigned anger she hissed. 'I'll make you pay
dearly for this Norma." And he was marched into Mrs Black's office!
A tear rolled down his face as he faced her.
"You were warned Norma." She told him calmly as she got up from her
desk. "There is no turning back now. You are a female prisoner. And you
will obey me. And you will wear the right uniform!"
And she unbuttoned his shirt!
Norman raised his arms and both maids moved close. He felt their hands
on his wrist, and surrendered!
He was quiet and subdued as she undressed him. But his face burned when
he stood before all four women naked and frightened.
When Olga handed him the white cotton panties he was only to eager to
step into them - at least they covered his genitals! The she slipped bra
straps up his arms! It was an old-fashioned full-cupped garment with
smooth nylon straps and high elastic sidebands. He gasped aloud when he
saw how it forced his chest into a full round bosom.
"Be still!" she barked.
Norman froze and minutes later he was wearing a skirt! A lovely lace-
trimmed and full-skirted petticoat. And it occurred to him that the
atmosphere had changed. Mrs Black couldn't keep her hands off his new
skirt and bust. Olga was flushed with excitement. And even Sally was
aroused!
Norman experienced a sense of panic as the transformation continued
relentlessly. A dress! A wig! And the sexual tension in that room
increased to fever pitch!
Mrs Black made the first move. An awkward attempt at kissing him.
Confused he moved away from her.
Olga cuffed him. Mrs Black frowned. "That's alright Olga, Norma still
has a lot to learn. Why not take her to her cell. She can spend the
night with jenny."
Sally's mouth dropped open. And Norman was scared!
Mrs Black moved close. "You can call on me at any time Norma. But the
next time you reject me I'll have you whipped." She whispered in his
ear. "now run along, I'm sure you and Jenny will enjoy each other's
company!"
He followed Olga out of the office carrying the rest of his clothing.
"This is your cell," she told him as the reached the lower floor. You
can sleep here tonight, or, if you ask me nicely, you can sleep in my
room." Olga told him.
Norman felt himself pushed into a small cell. And then he saw his
cellmate! A huge gorilla-like woman.
Olga grinned. "Jenny - meet Norma."
Norman heard the cell-door being locked behind him. He experienced a
moment of sheer panic.
Jenny snickered. "So they've brought me a sissy-girl to play with have
they?"
Norman felt his knees buckle as the grey-haired and toothless woman
caressed him through his thin dress.
"Please! Don't ....!" he stammered as her fingers began opening his
dress.
Her slap was casual but brutal! Smack!
Norman was knocked sideways. His head reeled from the sudden blow. He
leaned against the cold brick wall and meekly allowed the middle-aged
crone to open his dress.
"Are you going to be nice to Jenny?" she crooned. And her hand squeezed
his breast through his bra.
"Yes. Please don't hurt me," he replied.
Jenny kissed him. Her soft wet mouth closed over his and he gagged. Her
thick tongue forced his lips open and rudely explored his mouth!
The sound of the cell-door opening saved him. Jenny reluctantly moved
away. Norman gasped like a fish out of water as he slowly and clumsily
fastened his dress.
Olga raised an eyebrow. "Am I disturbing you Norma? Should I come back
later?"
"No!" he whimpered.
"Would you like to stay with me tonight Norma?"
"Yes!" he told her eagerly. "Oh yes!"
"You'll be .... nice ... to me?"
He paused. Cast a quick glance at the slack-mouthed Jenny. "Yes."
She marched him towards the staff quarters as though afraid he might
have a change of heart.
After Jenny's assault he was calm and still when Olga unbuttoned his
uniform dress. He didn't care. He could still taste Jenny's probing
tongue and he felt sick! Olga gazed at him for a long moment. "You've
tasted life with Jenny - do you want to spend five years sharing her
cell?"
He shook his head. "Never!"
Olga moved close. "I could take you to the men's section right now - I'm
sure they'd know what to do with a she-male."
A cold fist gripped his innards. Meet male prisoners in a dress?
"You wouldn't. You couldn't!" he whispered.
Olga leaned forward, her nose touching his. "I could. And I would!"
Norman clenched his fists. "Just tell me what you want."
Olga took his hand and placed it over the front of her tight linen
skirt.
Norman frowned - and then felt it. He froze and tried to pull his hand
away. Olga was wearing a dildo!
"No!" he whimpered. "Oh no!"
Olga pulled him close and kissed him. Norman sagged weakly against her,
his hand still on her thick hard 'penis'. As her kiss became feverish,
as her tongue invaded his mouth he found himself exploring the length of
it through her skirt.
She dressed him for her bed in an old-fashioned nightdress - a long
front-buttoning gown of soft cotton lawn. And Norman watched as she
unbuttoned her uniform shirt. His eyes widened at the sight of her
jutting bra-covered breasts. He became hot with lust as she unbuckled
her shiny leather belt. Blushed as she pushed her skirt and waist slip
over those incredibly wide hips. He stared at her bulging corset.
"Touch it," she breathed. And he obeyed. Her 'penis' seemed to throb in
his grip! As Olga eased him onto her bed their eyes met.
"Tell me you want me," she hissed.
Norman didn't hesitate. "You know I want you. But please, don't hurt
me."
Olga hesitated. It suddenly occurred to her that this she-male actually
was excited.
"You do want me ... she really do want me."
Her dildo jutted obscenely from between her meaty thighs. It bobbed
ludicrously as she slid onto the bed beside him.
Norman moaned with a girlish excitement as this huge woman settled her
soft body on top of him. Her pointed bra cups bruised his chest as he
felt the first impatient prod of her 'penis'.
Norman slipped his arms about her broad shoulders. His palms explored
her Lycra corset as she nudged his trembling thighs apart. And
incredibly - as she thrust her groin into him - he raised his hips and
buttocks in sluttish and wanton invitation to her dildo!
Olga speared him with a swift jerk of her wide hips. Norman gasped in
pain as fire invaded his body!
He clung to her back with clawed fingers and bit deep into her shoulder!
He felt skewered! Violated! And fulfilled!
Olga slammed into him repeatedly, in and out, in and out. She bucked and
heaved on top of him with a wild abandon, a feverish excitement that
thrilled him.
And Norman urged her on! He whispered in her ear as she slammed her
groin against him.
"Oh yes, oh yes, harder darling, oh harder harder harder!"
He felt her hand paw his breast - felt his nipple sprout. Her mouth
found his and he eagerly and sluttishly sucked her tongue deep inside
his mouth. For a long time the only sounds her heard were the creaking
of her bed, the slap of her naked flesh on his and her heavy breathing
as she rutted contentedly on his feminised body!
The next morning she gave him a simple choice.
"Stay here - as my maid, or go to the men's prison."
"I want to stay .... Mistress Olga," he told her truthfully.
But his first duties were not as a servant. As she dressed him he
suspected as much. The clothes were soft and pretty in nylon, satin and
lace.
He was hardly aware of the satin and lace bra she drew lovingly up his
arms. And he was almost indifferent to the lace garter-belt and matching
nylon panties! The flimsy nylon blouse, pretty though it was, didn't
bother him - although he was only too aware of the fact that the thin
nylon allowed his bra to be seen through it. It was only as she helped
him into the frothy waist slip he belatedly realised what was happening.
The skirt was of a similar material. Very thin and lightweight red
nylon.
"Sit," she said. "Roll these up your legs, don't ladder them."
His face burned as she helped him place the first of the seamed fully-
fashioned stockings on his toe. He ran the nylon through his hands and
slowly unravelled it along his foot, his ankle and along his legs.
Olga showed him how to fasten the nylons to his garter-belt. And her
fumbling at his groin produced a stunning erection that made her giggle!
"I'm sorry - I can't help it."
Olga kissed him softly. "Now I know you want me. Tonight I'll make you
mine."
He shivered.
She was much more confident now, 'I want you to meet some of my staff.
The off-duty ones are waiting for you. Understand this - you must do
anything they ask of you. You are still a prisoner. You have no rights
here. Remember that. Anything!"
Norman, walking awkwardly in his four-inch heels, entered the staff
room! He was full of weak-kneed fear - and was immediately relieved to
see only two girls present. They were both attractive, and smartly
dressed in flowered silk frocks and high-heeled shoes.
Olga introduced them as Sally, and Wendy. "And tell them your name..."
She said to Norman.
Norman flushed ... and then went bright-red when he heard the two girls
giggle.
Olga jabbed him hard and he answered with a whisper, "My ... my name is
Norma."
Wendy, who wore a wide-skirted frock of yellow silk, grinned saying,
"Welcome Norma, or is it Norman? What do you think Sally ... is this
really a girl?"
"Only one way to find out," laughed Sally, "lift up your skirts, let's
see what you have under there!"
Olga smiled ... and backed out of the door.
"Come on," the two girls shouted, "raise those skirts and petticoats!"
Full of fear and confusion Norman pulled his skirt and petticoat above
his knees. "Higher!" they squealed.
Feeling a sting of tears at his eyelids Norman lifted the skirt high
showing the top of his stockings and suspenders.
Sally got up from the couch and stood next to him. Her hand went under
his skirt ... after a bit of fumbling she found his panties. Gripping
him tightly through his nylon panties she squealed with delight!
"Wendy .... it's a boy! Come and feel!"
Norman could have screamed with utter despair as she dragged him,
painfully to the couch!
Wendy stroked his thigh saying, "He has very nice legs for a boy. Why
are you wearing panties? Are you a sissy?"
"He's a pansy!" screamed Sally.
Norman felt tears trickle down his cheeks.
"No! He can't be a real boy; look he's crying like a big soft girl! Is
that right, are you a big soft girl pansy?"
Norman sobbed as they teased him unmercifully. Sally fondled him rudely
through the silky sheer panties ... and as he became excited - her eyes
gleamed. Now her other hand went under his skirt and cupped his
buttocks.
Wendy unbuttoned his blouse and slipped a hand inside. She gripped his
breasts through the satin-cupped bra, "But he must be a girl, boys don't
wear bras. I love your breasts darling ... why don't you feel mine, go
on, do as I say, feel my breasts!"
Norman reluctantly placed his palms over her large round breasts. He
squeezed gently .... it felt very nice. He cupped them in his hands
enjoying the weight heavy in his palms through the smooth silk of her
frock.
"I don't think its right," she muttered crossly, "a boy wearing a bra!
It's shameful!
"And panties!" said Sally. "He's wearing women's panties!"
Wendy stared at him with a mad gleam in her eye. "I think you should be
punished."
"Are you going to beat him?" Sally sounded very enthusiastic.
Wendy nodded, her eyes still on Norman. "Yes. I'll spank him... and you
can watch!
Horrified, but completely helpless... Norman felt himself manhandled
across Wendy's ample thighs.
Sally took her time arranging him along the couch and over the other
woman's bared thighs. She drew his skirt and petticoat up over Norman's
buttocks with sniggering comments about his female underwear.
Norman sobbed quietly. A tremor passed through him as Wendy caressed his
buttocks through the nylon panties, her hands pulled his thighs apart -
and she slid a hand between them. "What gorgeous buttocks!"
Sally was impatient now. "It will look even better when it's all red and
sore, go on, hit him!"
Wendy brought her heavy hand down smartly across Norman's bare upper
thigh. He squealed in pain. His wriggle seemed to inflame Wendy. She
took a firm grip of his waist with one hand and began vigorously
slapping and spanking his panty-covered bottom.
"Pull his panties down! Beat his bare bottom!" Sally too was excited!
Tears of rage and humiliation coursed down Norman's cheeks as the two
women drew his panties down over his thighs. SLAP, SPANK, SLAP, SPANK,
SLAP!
The sight of his bottom turning a fiery red brought Sally's lust to
fever pitch. She ripped off his blouse, and pulled his skirts down.
Norman fell in a heap at their feet. They roared with laughter when he
struggled to pull his panties back up his legs.
"See how he loves his panties!"
Norman looked up. Wendy, breasts heaving magnificently, raised her
skirts. "Get your head under here!" she muttered thickly.
Crawling on all fours Norman ducked under her silk skirt. The smell of
her lust was unmistakable.
Sally kicked him hard saying, "You know what to do under there ... kiss
her legs!" Norman swallowed nervously ... then placed his lips against
the smooth inner thigh. He felt a shudder race through her body! She
reacted as though he had prodded her with a reed hot poker! Her body
jerked and convulsed as he kissed her ... and her thick meaty thighs
held him tight! The two girls took turns to be serviced and Norman spent
hours on his knees at their feet ... and between their legs!
He was sobbing hysterical when Olga returned. And was only too eager to
follow her - to her bedroom.
Trisha
- 14.09.2021
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