Author's note: This tale continues the life of Christopher De Coursey,
whom we first encountered in "The Rehearsal." Although it is written as
a stand-alone story, the reader would benefit from reading the first
narrative.
Usual warnings apply: If you're too young, if it is illegal to view
this kind of material where you live, or you don't like stories with
cross dressing and transvestism themes, then kindly leave now.
Otherwise, enjoy, and remember; IT IS FICTION.
Two Halves
By Belle Gordon
Christopher.
The intercom made its irritating buzz. Chrissie pressed a button.
Alistair's tinny voice announced that they should leave now if they
were to get to the airport on time for her flight. She stuffed the
papers she'd been studying into her briefcase, stood and entered the
adjoining bathroom. She checked her appearance in the mirror. She'd
dressed with extra care this morning wanting to look her very best for
her meeting later with the chief executive of a big US company. She
wore her best silk lingerie under a beautifully tailored cream linen
suit matched with a chocolate silk blouse, tan hose and mid-brown court
shoes with comfortable 3" heels. Her hair, which she'd had washed and
set this morning cascaded over her shoulders in unruly waves. She wore
discreet gold earrings and a gold neck chain. Not bad, she thought
winking at her reflection; she looked every inch the elegant,
successful businesswoman.
Grabbing the briefcase she walked from her office. Alistair scampered
after her with her ticket and passport and held the door open for her.
They took the elevator to the lobby from her top floor office. The
doorman spotted her coming and scurried forward to open the doors. He
touched his forelock as she swept regally through, down the steps and
entered the waiting Mercedes. Alistair slammed the door behind her, ran
round to the driver's side, got in and sped off into the morning
traffic.
Pulling into the set-down area at the airport, she said, "Thank you,
Alison. I shall see you tomorrow. Now remember your instructions. You
know what will happen if you do not carry them out to the letter?"
"Yes Madam." He said. "Are you sure there's nothing else you'd like me
to do?"
"No. Just do what you've been told. Good bye."
Carrying her overnight valise she followed the signs for the Concorde
check-in. The necessary formalities were quickly completed and she was
ushered into the departure lounge. Travelling by the world's most
sophisticated airliner certainly has its advantages. There was minimal
delay with boarding; taxiing and takeoff went smoothly. The surge of
power as the beautiful aircraft took to the air was exhilarating. What
an awful pity that such a superb aircraft was soon to be withdrawn from
service. I was almost criminal.
The captain set his course for New York and accelerated to mach 2.
Chrissie accepted a complimentary champagne cocktail from the flight
attendant and settled back into the comfortable seat. Her mind drifted
back 16 years to the events that were to change her life.
Olivia.
When Olivia's mother died and she'd inherited her father's fortune they
had moved to Scotland to live on an estate she now owned. Christopher
was fourteen and was going through a difficult period. He was
discovering his feminine side and was more and more dressing and living
as a young woman. His mother didn't have a problem with this as she'd
always wished he'd been born a girl but she worried he might be suffer
some psychological damage if he wasn't carefully guided and advised.
When they moved to Scotland, Chrissie's school drama teacher, Salvador
DiMarco, had resigned his post and accompanied them. He and Sal had
become lovers whilst rehearsing for the end-of-year school play. Being
a transvestite, he had introduced Chrissie to the world of cross-
dressing. He had taught him all the techniques necessary to become a
successful female mimic, and encouraged him to develop his femininity.
Olivia was very happy with the situation. Chrissie was rapidly
transforming into a beautiful young girl. Now that they were living in
relative isolation, Sal had also begun to cross dress full time and to
the outside world they appeared to be three women living together, a
mother, her daughter and the child's governess.
Very soon after they were settled Chrissie made the permanent switch.
He watched with Olivia and Sally, as one by one they threw his
remaining male clothing onto a bonfire in a symbolic gesture of no-
turning-back. As the last items burned he exhaled a contented sigh and
a feeling of wellbeing spread through his body. He finally felt
released from the bonds that had invisibly bound him for the last
fourteen and a half years. Now he could become the person he deep down
felt he was, a woman.
For the first six months everything was fine. They all lived happily
together. Olivia was forming a close relationship with Sally and they
were spending a lot of time together, leaving Chrissie to look after
himself. He noticed that they'd begun sharing each other's clothes and
jewellery. They helped each other with their makeup and hair styling.
They went for long walks together and often talked intimately excluding
Chrissie from their conversations. He was beginning to feel resentment
towards Sal.
To celebrate their first six-months together they held a small party.
After a sumptuous dinner they sat in the drawing room before a roaring
log fire sipping brandies. To make the occasion a bit special they had
taken the trouble to dress up and each was wearing their best evening
gowns and showiest jewellery.
Music was playing on the stereo and Sally asked Olivia if she'd like to
dance. Chrissie felt a little envious at the attention he was paying
her. After all, he thought, we are lovers so why doesn't he ask me to
dance. He rebuked himself for being so petty and decided to be happy
for them both. As he sat watching them dance together he noticed that
Sally was nibbling her ear and was grinding his crutch against her.
Olivia responded by pushing back against him and kissing his lips. Soon
they were kissing deeply and swaying together, oblivious to Chrissie's
presence.
They didn't notice when he left the room. He decided he was being a
gooseberry so took himself off to bed. Some time later he heard the
tell tale sound of the stairs creaking and a door bang, followed by
drunken shushing. His curiosity got the better of him and, although he
knew he shouldn't, he got up and tiptoed from his room. Light was
spilling through the partially opened door of his mother's bedroom. His
bare feet made no sound as he crept to the gap and peeked inside.
Sally and Olivia were stripped to their lingerie, lying in each other's
arms and kissing passionately. Their groping hands exploring breasts
and buttocks, and as he watched Sally rolled on top of her, pulled
aside his panties, and slid his erect cock into Olivia's gaping cunt.
"Oh, yes, Sally, my darling girl, fuck me with your lovely dildo." She
breathed. "Fuck me with your girlie cock. It's so hard and hot. Fuck it
into me deep and hard."
Chrissie was shocked to hear her mother say such things, but she
continued murmuring obscenities as Sally ploughed deeply into her. He
could see her love juices shining wetly in her eager gash. The
spectacle of his wanton mother copulating with, as she imagined,
another woman was having a predictable effect on him. His cock had
risen to full, quivering erection and was protruding through the front
of his nightie. His small hand wrapped the soft silk of his nightdress
round his burning shaft and he masturbated as he avidly watched the
exhibition before him.
He matched his wanking hand with Sally's strokes as he plunged deeply
into his mother's liquid pit. Suddenly his humping hips stopped and he
lay still, buried inside her. Chrissie was afraid he'd been caught
spying on them, and his pumping hand froze. But they were only changing
position. Olivia turned Sally onto his back and quickly straddled him
directing his flaming cock back into her eager trench and began to ride
him.
"Ahhh. What a wonderful dildo you have, Sally my darling," she gasped.
"It feels so real ... so lifelike. I want it all inside me. It's so
much nicer than a man's penis. We girls know how to do it so much
better." She continued to maintain the charade of a lesbian coupling.
Somehow during this time Chrissie had had silently entered the room.
He'd uncovered his penis from the folds of his nightie and stood at the
foot of the bed masturbating furiously. His eyes momentarily left the
writhing couple on the bed and glanced into the mirror of the adjacent
dressing table. Reflected in the glass his eyes met those of a teenage
girl, wearing a silk nightdress that was rucked above her waist.
Protruding from a tiny tuft of pubic hair was an obscenely erect cock
that was being stroked by the dainty hand of the girl.
Also staring back at him from the mirror was his mother. He was shocked
into immobility. His beating hand flew to his open mouth and he wanted
to cry with embarrassment. To be caught brazenly masturbating whilst
watching his mother ride her lover's cock was almost more than he could
stand. More than anything at that moment he wished he could disappear.
Then he got a second surprise. Unable to tear his eyes from the lovely
face of his mother, he saw her smile and imperceptibly nod her head in
approval.
Their eyes remained locked together as she continued fucking Sally
beneath her.
"Ah yes darling girl." She said. "What a lovely cock you have. So big
and beautiful. Perfect for a pretty girl like you. How I love to feel
it inside me." All the while she was looking intently at Chrissie,
smiling and nodding her head. As if with a mind of its own his hand
again gripped his erection, which seem even harder, and began to
masturbate once more. "Yes, that's it. Do it for me. Show me you love
me and cum for me, shoot your seed for me." Although it appeared her
obscenities were meant for Sally it was clear they were directed at
Chrissie.
Just then Sally groaned loudly and thrust upward into Olivia's pounding
hips emptying his balls into her. At the same instance Chrissie's
beating hand achieved the inevitable result. His cum arched from his
twitching organ and splattered across his mother's back. Feeling the
hot liquid on her skin she quickly swivelled 180 degrees on Sally's
spear to face him directly as his second emission erupted. This time
his jism hit her in the face, throat and breasts. A third pulse
followed and this too hit her squarely in the face, covering her nose
and chin. She smiled broadly and licked her tongue round her lips
trying to reach the dribbling spunk; her hands smeared the gooey stuff
into her breasts.
After several minutes when his erupting dick had subsided, he quietly
left the room on shaking legs and returned to his bed. He was just
falling asleep when the door opened and a figure entered. Olivia sat on
the side of his bed and placed her hand on his cheek.
"Are you awake?" she asked.
He nodded, afraid to speak. "You are a very naughty girl to spy on your
mother," she said. "I should be cross with you; you ought to be
punished."
"I'm sorry, Mummy, I didn't mean to spy on you. I heard a noise and
came to see what it was. When I saw you and Sally something came over
me and I couldn't help myself. You looked so beautiful and sexy I
couldn't stop myself from masturbating." He started to sob.
"It's alright, honey. Don't cry. No harm has been done. In fact, I'm
flattered that you find me so sexy. Now give me a good night kiss and
we'll say no more about it."
She leant forward and pressed her lips against his. He could taste
Sally's lipstick.
Olivia.
Seven weeks after their little party, Olivia made two major
discoveries. The first was that Salvador DiMarco had disappeared:
together with the contents of her safe, totalling some two million
pounds in cash, bank drafts and travellers checks. He'd also taken
several of her nicest and most expensive dresses, a mink and silver fox
furs and ten pair of shoes. He'd loaded it all into the Mercedes and
gone.
The second discovery was that she was pregnant. Of the two the latter
was the most shocking. She could easily replace the money, the clothes
and the car, and as for Salvador DiMarco good riddance to him; but what
was she to do about her pregnancy. An abortion was out of the question.
Her upbringing and her religious beliefs were totally against it, so
she'd have no alternative but to carry the child to term and give
birth. But what then? Adoption was an option of course, but again she
was reluctant to follow that course.
She really did not want another child. She and Chrissie were very happy
together and she had plans to help him transform into the perfect
woman. She had already made appointments for him to have breast
augmentation and collagen implants. His laser hair removal treatment
was almost completed and the larynx reduction had been a complete
success. Now along comes this problem to foul up their idyllic life.
Over the months that followed, as her body bloated, her belly swelled
and her breasts became enormous; she made arrangements for the child's
care. She located another woman who was due to give birth on the same
date and was willing to act as a wet nurse. The thought of a child
sucking at her nipple repulsed her. She engaged a nurse to look after
its day-to-day needs and to take complete responsibility for its
welfare. She had decided that she wished to have as little to do with
the child as possible.
In the fullness of time the child was born. The birth was trouble free
and she was successfully delivered of a baby boy, weighing in at 7lbs
9ozs. She felt cheated that the child was male and saw it as the final
insult. Had it been a girl she would not have felt so miserable.
All her experiences with men had been bad ones. She'd married young,
given birth to Christopher nine months later and been reasonably happy
for the first six years. Then she discovered her husband engaged in a
homosexual menage-a-trois. She divorced him immediately and until the
unfortunate affair with Sal had had nothing to do with men, satisfying
herself with her vibrators and dildos.
They named the child Leon, but because of a clerical error during
registration DiMarco became Marcus. Olivia couldn't be bothered to
change it. The boy grew up in a separate wing of the manor house being
raised by a succession of carers. Olivia avoided him all she could and
only saw him when it was absolutely necessary. On his eighth birthday
he was sent to boarding school. He'd always been a sickly child
suffering constant illnesses. Perhaps because of insufficient
nourishment during his early years he grew up small of stature and
spindly limbed. He was unloved and lacked affection because of the
ever-changing succession of nannies and nurses.
Leon hated the schools he was sent to. All of them were boarding, and
always for boys only. He was bullied constantly and frequently ran
away, only to be returned to more hardship and punishment. At age
fifteen he dropped out. The school authorities did not object; he'd
fulfilled the legal minimum educational requirement. Deciding there was
no benefit to be gained by keeping him there he was sent home. He was
unruly, disobedient and disrespectful. Olivia did not know what to do
with the boy.
Christopher.
Alistair was dutifully waiting for her as she exited the arrival hall.
He took her valise and stowed it in the boot of the car then set off
into the traffic of the M4 heading into London.
"Was Madam's trip successful?" he inquired.
"Yes very, thank you, Alison." She replied. She'd begun calling him
Alison as a way of embarrassing him soon after they had met and it had
stuck. "Any news?"
"Your mother rang. She seemed to be in a bit of a state. You're to
phone her as soon as possible."
She sat in the front with him and noticed the new silk blouse he was
wearing. Over the years he had taken to wearing more feminine styles of
dress. Although not a true crossdresser he preferred softer fabrics and
often wore women's tops and underwear under his suits. He still
preferred his kilt although now they were tailored as skirts. He was
still very prone to blushing when embarrassed. His devotion to Chrissie
had not diminished over the years; in fact his life was now totally
dedicated to serving her. He had become indispensable. During the day
he was her p.a., running her office with consummate skill, her
secretary and also her chauffeur. At evenings and weekends he
maintained her luxury apartment. He cleaned and cooked, did the laundry
and ironing, shopped and did whatever other household duties were
required. She had allocated one small room for his personal use and he
was perfectly content to live there.
They had met many years previously when Chrissie had first moved to
Scotland. He lived with his aged mother in a tied cottage belonging to
the estate. Chrissie soon discovered she had enormous power over him
and that he would do anything she asked. She decided to subjugate him
to her needs and devised a test to see how far she could push him. On a
busy Saturday afternoon in the centre of Edinburgh she totally
humiliated him and he had been her virtual slave ever since. Only later
did she discover the full extent of his masochism and his need for
servitude. [You can read about this in 'The Fellmongers Apprentice' by
Belle Gordon]
Arriving in the underground car park of her tower block he parked in
her reserved space. The elevator whooshed them up to the penthouse
floor and he opened the door for her. He carried her bag into her
bedroom and set it on the foot of her bed.
"You can unpack my bag later, Alison. Pour me a G. and T. while I see
what Mummy wants."
She picked up the bedside telephone and punched in the number. She
noticed with satisfaction that her lingerie had been washed and
carefully ironed then put neatly into her vanity unit as she had
instructed him. Her dresses and shoes were all tidily hung in her
closet and the whole room was spotlessly clean. As she waited for her
mother to answer, Alistair brought her drink. He had removed his jacket
and had tied a white cotton apron with a ruffled border round his
waist. He carried the glass on a silver salver and placed it besides
her.
"I like your blouse, Alison." She said. "Is it new?"
It was white silk with a fine blue pinstripe, large Peter Pan collar
and double cuffs.
"Yes Madam. I treated myself. I bought it in Dorothy Perkins after I
dropped you at the airport."
Just then her mother's voice came on the line. "Hi, Mum. What's up?"
"Oh, Chrissie. I'm so glad you're back. I've a real problem. You've got
to help me."
"What's the matter?"
"It's Leon. He's been expelled again and sent home. They say they can
do no more for him and that as far as they are concerned his education
is finished. I don't know what to do. I don't want him here; you know
how I feel about the brat. He's too young to join the army so do you
think you might be able to find him something to do in your office?"
"I don't know, Mom. I haven't seen him for years, not since he was 7 or
8. I'm not sure I can find him anything to do. Alison pretty much does
everything I need."
"Please. I shall go mad if I have to keep him here."
"Oh, alright then. Put him on the overnight train and I'll have Alison
meet him. I suppose he can always make the tea."
"Thanks, darling. You're a pet."
After Salvador DiMarco had absconded with the contents of the safe,
Chrissie had begun to take an interest in the business. It had
originally been set up to more or less run itself with only a monthly
meeting between mother and her advisors. Chrissie began attending the
board meetings and was soon making investments of her own. She showed a
natural flair for trading in stocks and shares and had rapidly become
very successful. By the time she was twenty she'd made her first
million and had never looked back. Now at 30 she had increased the
family fortune three fold and was worth 20 million pounds in her own
right.
"Alison." She called, replacing the telephone. "We're going to have a
visitor. Leon is coming to stay. He'll have to go in the spare room.
What's it like?"
"Perfectly liveable." He said. "But the closets and drawers are filled
with your spare clothes. I'll make some room for his things and make up
the bed. When is he arriving?"
"In a day or two."
She wasn't too sure Leon would appreciate the d?cor. The Laura Ashley
designed wallpaper had pretty pinks roses intertwined with white mimosa
flowers. The curtains and drapes were soft pink velvet, the thick-pile
shag carpet was lilac, and the furniture was contemporary white wood
with brass fittings. Her interior designer had decorated it in the same
feminine style as the rest of the apartment. It would be impossible to
change now at such short notice, so Leon would just have to like it or
lump it.
He arrived two days later on the overnight sleeper and Alistair met him
at Euston station. Chrissie realized she was quite nervous as she
awaited his arrival. It had been many years since she'd last met him
and only had a vague memory of what he looked like. She offered a
silent prayer that everything would work out ok and his stay would not
be too traumatic. Eventually she heard the double ping of the elevator
bell, the signal that someone was on the way up.
The doors opened and Alistair entered, preceding a small figure
carrying a suitcase. She noticed he quickly surveyed the room as he
marched over to her, stood to attention, held out his hand and made a
small bow. She shook the soft limp fingers that he offered, and studied
him more closely. She was shocked by his striking resemblance to
Olivia. He had the same high cheekbones and soft jaw line. His nose was
the same pretty shape and his lips were also full and fleshy. His eyes
were the same startling blue as Chrissie's. Although she knew he was
fifteen she would have guessed he was at least two years younger. He
had the pre-adolescent appearance of a child. The skin on his face was
soft, smooth and white; his chin had no hint of a beard. He was
slightly shorter than Chrissie's diminutive 5'5" and weighed no more
than 100 lbs. His hair was matted, greasy, and reached to the collar of
his baggy, hooded sweatshirt. He wore a pair of oversize trousers with
many pockets, in the style favoured by skateboarders, and scruffy, worn
trainers. When he spoke his voice was high and piping.
"It's very nice to meet you again Leon, after all these years." she
said. "I hope you'll be comfortable with me." His presence was having a
disturbing effect on her. As he looked at him she was conscious she was
becoming aroused.
"Nice to meet you too, Chrissie."
"Alistair will show you your room and help you unpack, then you might
like a bath and a change of clothes."
Alistair unpacked his bag and stowed his few clothes away in the drawer
he'd made available. If Leon didn't approve of the d?cor he said
nothing. She watched him unobtrusively as he went about the business of
establishing himself in his new quarters; switching the TV on and off,
checking out the stereo system and CD collection. She was again aware
of the troubling feelings centred in her groin. He was amazingly
childlike, and she wondered how such a pretty child had survived at
school. She remembered her own days of endless taunts and bullying
because she didn't match up to the accepted norm for a boy, and felt
sorry for him.
After supper they played scrabble together for an hour then Chrissie
announced it was time he went to bed.
"Will you come and kiss me good night please, Chrissie."
"Yes of course." she said, a little surprised by the request. "Give me
a call when you're ready. And don't forget to brush your teeth."
Ten minutes later, in answer to his piping call, she entered his
bedroom. He lay on his back with the sheets round his waist. His bare
chest was smooth and hairless with small brown nipples. She caught her
breath when she saw him lying seductively on the lacy pillow, the pink
glow of the night-light illuminating his soft features. She bent down
and pressed her lips gently against his. He tasted so sweet and tender
that she was tempted to crush her mouth hard against his and force her
tongue into his mouth. Her hand stroked across the soft skin of his
chest her fingers brushing against his nipples. She quickly pulled her
hand away and stood up. What was she doing? He was her brother; she
shouldn't be feeling this way. But she couldn't deny the lustful urge
she felt for him.
"Why aren't you wearing pyjamas?" She asked, inhaling a calming breath.
"I'm sorry, Chrissie. I don't have any. I usually wear at t-shirt but I
seem to have lost it. It's Okay though, I like to sleep naked."
"Well you will have to wear something."
From the moment he'd entered the apartment an unbidden thought had
entered her head. Much as she tried to disregard it, it began to take
on a more definite form and would not go away. She became excited by
the idea of turning him into a beautiful girl. As she'd observed him
through-out the day the scheme had grown in her mind, and now, looking
so desirable lying in bed she decided to implement it. She would
introduce him to the pleasures of feminine dress. She intuitively felt
that he would accept the concept, but was surprised by the enthusiasm
with which he ultimately embraced it. Now she had a perfect opportunity
to easily initiate the first step. Going to her closet she found one of
her most feminine nighties. It was a pure-white satin baby-doll with
matching panties. It was gathered under the bust with a red ribbon, and
the bra cups were delicate lace. It had spaghetti shoulder straps and
was so short it barely covered her bottom.
Walking back to his room she handed it to him and told him put it on.
"I can't wear this," he protested "it's a girl's thing."
"I'm afraid it's all I have," she said "besides, who's going to see you
except me and Alistair? And you never know, you might like wearing it.
Now come along and put it on."
He held the nightie in one hand and the panties in the other and didn't
seem to know what to do next. "Do you want me to help you with it?" she
asked, she could see he wasn't sure how it went on.
"Yes please." He handed it back to her.
"Jump out of bed and slip these on first" she said handing him the
panties.
He threw the sheets back to reveal his naked body. Her breath caught in
her throat when she saw his wonderfully smooth, hairless child's body.
His penis and testicles were surprisingly large for such a slight frame
with just a tiny tuft of blond pubic hair. It flopped against his belly
as he bounced off the bed. He showed no reluctance at displaying his
nakedness and was completely unselfconscious. He stooped and pulled the
panties up his legs.
"Back to front." she said. He looked at her with a puzzled expression.
"You have the panties on the wrong way round. Take them off and put
them on with the lacy bit to the front."
He slid them down his legs, turned them round and pulled them on again.
This time the lace panel covered his cock and balls and the thong
nestled into the cleft of his bottom. She reached forward, gripped the
elasticised waist and gave them a tug fitting them snugly between his
cheeks. She slipped the nightie over his head and smoothed it down his
body. She adjusted the red ribbon that encircled it under the bust till
it was in the correct position then tied it in a bow. She gave the hem
a little tug downward and fixed the shoulder straps. It fitted as
though made for him. He looked absolutely divine. She could feel her
cock straining inside her panties as she gazed at the lovely image he
made. She longed to take him in her arms and kiss him but she didn't
want to alarm him. Slowly, slowly, she told myself.
She suddenly had an inspiration as to how she could stay with him a
little longer without raising his suspicions. "Did you brush you hair
before you got into bed?" She asked him. He shook his head in a
negative. "Well go and get your brush and I'll do it for you."
She watched him as he minced across the room, the baby doll swinging
round his hips, and return with his ivory-backed brush and comb. He
walked on his toes placing one foot in front of the other, with a
natural grace.
For the next twenty minutes Chrissie brushed and combed his long, thick
hair. Now that it was freshly washed and conditioned it was more
manageable. She tried out several styles and thought that with very
little effort she could create a very feminine style. In the end she
decided on a pageboy bob. She used scissors to snip and trim little
ends of hair here and there till she was happy with it. It was not
blatantly feminine but was a bit femme for a boy.
Finally she could not keep him from his bed any longer. Tucking him in
she kissed him good night again. This time her kiss was longer and she
couldn't resists snaking her tongue between him lips for an instance.
Back in her room she hurriedly stripped her off panties and lay back on
her bed. She gripped her throbbing member and masturbated to an
explosive orgasm, with the taste of his sweet lips still on her tongue
and the image of his sexily clad body in her mind.
Leon.
Throughout the following weeks Leon became totally devoted to Chrissie.
He confessed to her much latter that she was the first real friend he
had. No one ever took any notice of him or talked to him. A governess
had taught him to read and write at home during his first years of
education, and this was followed by a succession of private boarding
schools. He had been shunned and ignored by the other students who
found him stand offish and aloof. He was bullied unmercifully and
subjected to endless derision for his ineptitude at games. Quite how he
would manage in the world of work Chrissie couldn't imagine.
He followed her everywhere like a faithful dog, and she would often
catch him staring at her as she sat at her desk. In all truth he wasn't
a great deal of help to Chrissie. He couldn't type, didn't know how to
file and a computer was a mystery to him. He finally got the hang of
the photocopier and could make a reasonably drinkable cup of coffee.
She discussed his future with Olivia and they agreed that it would be
pointless trying to find him employment elsewhere, so it was decided
that he should stay and assist Chrissie and she'd teach him whatever
she could. Olivia didn't much care what he did so long as she didn't
have to do anything and he was safely out of her hands.
All these events suited Chrissie's plan admirably. From the first night
he had taken to wearing the baby doll nightie without a moment's
hesitation. She gradually alternated it with more and more elaborate
and sexy nightgowns and negligees. He loved to lounge around in the
silky robes and would often change into them as soon as he returned to
the apartment.
As part of his education and to help with the running of the apartment,
Chrissie ordered him to assist Alistair with the laundry and other
domestic chores. On a Saturday afternoon as she worked on some papers,
he had the ironing board set up in the kitchen. She glanced over at
him, saw him pick up one of her favourite silk bras, and gently fondle
it then rub it against his cheek. His eyes had a glazed, dreamy look as
he savoured the delicious item.
"Leon, what are you doing?" She asked.
Surprised and confused at being caught, he quickly put the bra onto the
pile of clothes he's already ironed. "Uh. Nothing, Chrissie." He
stammered.
"Yes you were. You were rubbing my bra against your face. I saw you."
"I'm sorry. I don't know why I did it. Something suddenly came over
me."
"Do you like my bra?" He nodded shyly. "How much do you like it?"
"I like it a lot. It's very pretty."
"Would you like to wear it?" A vivid scarlet blush suffused his face,
but he said nothing.
"Well? Would you?" She insisted.
He swallowed and slowly nodded his head. "Yes." he whispered.
"In that case you will have to ask me properly"
He hesitated for many moments, and then asked, "Can I wear it?"
"Not good enough." She said. "You must ask me nicely and say exactly
what you want to do."
Drawing in a deep breath and defiantly straightening his shoulders, he
turned and faced her. "Chrissie, please may I borrow your pretty bra to
wear?"
Chrissie's cock began to harden when she heard this young boy politely
asking for permission to dress in her sexy lingerie. "Of course you
can, my dear boy," she answered. "Is there anything else of mine you'd
like to put on?"
"I'd love to wear a pair of your pretty panties as well, if you'll let
me."
"Of course you can. Select the ones you like most and we'll go to my
bedroom and you can put them on."
Without hesitation he picked out a matching panty and bra in peach
silk; a bra with masses of lace overlaying the cups. He has obviously
admired these before she thought. As he led the way to her bedroom she
couldn't help noticing how slim and attractive he looked from the rear.
His longish hair, which she'd been grooming so carefully, swung against
the top of his shoulders and his hips swayed suggestively. He pulled
his tee shirt over his head as he walked in, then undid his belt and
dropped his jeans. She couldn't miss seeing his erection straining
against the front of his boxer shorts. He paused with his thumbs in the
waistband of his shorts and looked at her enquiringly. She nodded to go
ahead and he dropped them to his ankles. He made a half-hearted attempt
to cover his throbbing cock with his hands, and then decided that as
she was bound to see it anyway, there was no point. After all, he was
about to don a woman's bra and panties, with the consent and active
encouragement of the owner, so it hardly mattered that he was erect.
He quickly pulled the panties up his legs and trapped his cock with the
head peeking above the waistband. Picking up the bra he fumbled with it
ineffectually, unable to master the feminine complexity of donning it.
"You'll have to help." He said holding the frilly scrap out to her.
She inclined her head indicating he would have to be more specific and
polite. "Please, Chrissie, will you help me with my bra. I 'm not sure
how to put it on."
"Certainly, as you ask so nicely. Turn around." She put his arms
through the shoulder straps then stretched the two ends of the
elasticised band closed at the back, and hooked the clasp together. She
settled the cups onto his flat chest by running her finger under the
lower edge to ensure it was flat and correctly positioned. "It's a pity
you don't have any tits, this bra really suits you," she said. She had
a pair of breast forms that she sometimes used when she needed an extra
few inches, but decided she wouldn't reveal them just yet.
"Well, do you like wearing my underwear?" Chrissie asked. He was
standing in front of her full-length mirror, turning from side to side
admiring his reflection. "Do you like your new look?"
"Oh, Chrissie, they're lovely," he said, "They feel so nice and sexy. I
wish I was a girl and could wear them all the time."
"Well, you don't have to be a girl to dress in feminine lingerie.
There's no reason why you shouldn't wear them if you want to."
He suddenly turned and ran from the room into her bathroom with a cry
of "'Scuse me." It was several minutes before he returned with an
embarrassed look on his face. His erection had disappeared to be
replaced by a wet stain on the front of his panties. There was a
similar wetness in Chrissie's panties from the oozing pre-cum that was
leaking from her confined penis.
"I'm sorry," he mumbled. "I couldn't stop myself. That's never happened
to me before."
"That's Ok. It's very nice that wearing lingerie has that effect on
you. Now get a clean pair of panties and then carefully wash those
out."
For the rest of the day he pranced and minced about in her bra and
panties. Alistair raised a questioning eyebrow to her when he first saw
him thus attired, but she shook her head in a "don't ask" gesture. She
did ask him to cover himself but he said that if she and Alistair
didn't mind, he'd prefer stay as he was. And truthfully she didn't
mind. The sight of a lithe young boy clad in sexy lingerie was
extremely erotic. In the evening he did slip on a negligee while they
ate their supper.
At bedtime he called to her, and as had become their habit, she went
into his room for a goodnight kiss. He lay in bed, propped up on his
pillow with the duvet around his waist. He wore the nightie she'd given
him and she noticed he still wore the bra.
"You really shouldn't sleep in your bra, Leon," she told him, "sit up
and I'll help you off with it."
"Oh, please, Chrissie, let me keep it on, I do love wearing it so." He
pleaded.
"No, I'm sorry. You can wear another in the morning if you wish."
He sat up, raised his nightie over his head and leant forward. She
unsnapped the clasp at the back and slipped the bra down his arms. He
flopped back in disappointment. The bra had left red marks on his
beautiful white skin, especially where the bra cups had cut into his
flesh. She reached forward with a trembling hand and massaged the
impression that marred his chest, at the same time leaning forward to
kiss his lips. As their mouths met he groaned and squirmed sensually
under her caressing hand. Their kiss was more torrid that it had ever
been previously, and as her tongue probed the inside of his lips he
grabbed the hand that was teasing his erect nipple. She thought he
wanted her to stop, but instead he held her wrist and pushed her hand
down his body, under the covering and onto his rigid penis. She curled
her fingers round his hot shaft and slowly pumped the skin up and down.
Their lips mashed together and her tongue forced its way deeper into
his mouth. She lay beside him; her imprisoned cock fucked the bed. She
longed to release it and masturbate with him, but she was not yet ready
for the traumatic revelation that she was also a man. In a very short
time she felt his hips tense and thrust upwards to meet her pumping
hand and a moan escape his throat. He came in a torrent, covering her
fingers and palm with his hot sticky sperm.
At the same moment he was pouring forth his seed, the friction and
pressure on her cock caused a similar thing to happen to her. Her
panties and slip were flooded with the product her balls.
"You're a very naughty boy?" She teased. "Making me wank you off like
that. You should be punished."
She saw the look of fear pass across his eyes at her threat of
chastisement, but before he could protest she grinned at him and kissed
him again. Releasing his limp member she brought her cum soaked hand up
and held it before his face.
"What shall we do about this mess?" She asked. "You'll have to clean it
up." She paused, then said, "With you mouth. Lick it clean, every
drop." She ordered.
She systematically pushed each of her fingers into his mouth till he'd
sucked them clean, then presented the palm for his tongue to lick. When
all the cream had been removed she said, "Nice?" He responded by
licking his lips. "Sweet dreams." She said, rising from the bed and
leaving. She headed straight for her bathroom to clean herself up.
Christopher.
Leon's progress into feminism proceeded at a fast pace. She remembered
her own introduction to the wonderful world of transvestism at the
hands of Salvador DiMarco all those years ago. She too had been an
eager disciple to the pleasures of silks and satins.
Alistair was an enthusiastic assistant. Years previously when they had
first moved to London she had enrolled him in an evening college where
he studied beauty, fashion and hair care. He was now an expert with all
forms of make-up, hair cutting and styling; he was an excellent
manicurist and proficient at any other beauty treatments she might
need. It saved a fortune and he loved nothing more than to spend his
evenings fashioning new hairstyles for her or attending to her nails.
His hair was cut, styled and permed, and Alistair gave it a blond rinse
to highlight his natural fairness. Alistair also instructed him with
make-up and he soon became very adept. His mannerisms were naturally
feminine and he needed very little instruction on the finer points of
ladylike behaviour. Leon rapidly advanced from nighties and underwear.
Soon he was wearing either dresses or skirts. He took to high heels
like he'd worn them all his life. He studied dozens of fashion
magazines and talked for hours with Alistair about clothes, make-up
techniques, and the latest beauty trends. Since his introduction to the
world of femininity his whole personality had changed. No more the
surly, unresponsive curmudgeon: now he was happy, willing and eager to
please in any way he could.
One evening a few weeks later he came and sat beside Chrissie as she
worked on some papers. He wore pink, silk lounging pyjamas, a flowing
silk dressing gown and fluffy high-heeled mules. He'd found them in one
of her closets on one of his many sorties into her huge wardrobe. He'd
recently bathed and smelled of talcum powder and perfume.
"Chrissie," he said, "can I talk to you?"
"Of course, Leon. What's the problem?"
"Well you know how I adore dressing in all your lovely clothes and
wearing make-up and styling my hair and everything?"
"Mmm."
"And you know how much I like being a girl?"
"I had noticed."
"Well, it's just that, I wish I wasn't so flat chested. I'd really love
to have proper breasts." It came out in a rush. She had wondered how
long it would be till he realised that if he were to pass himself off
as a genuine girl he would need a bust.
"That's not a problem." She said. "There are lots of ways to create a
convincing bosom. We can get you some breast forms: the modern ones are
very realistic. Or you could get implants if you wish, but that would
involve surgery. We can also start you on a course of hormones but
these take quite a while before you see any effect."
"What I'd really like is some breast forms, please" he said, "Implants
are a bit radical at the moment. Perhaps I could start taking a mild
hormone too."
"Ok, we need to take our time with your transformation. No need to rush
things too much. A small hormone dose is a good idea. It'll help keep
your skin soft and hairless but they won't inhibit your sex drive."
She called Alistair from the bathroom where he was hand washing their
lingerie. "Alison, in the morning go to the 'TrannyStore' and buy Leon
a set of breast forms. I think a 36C should be suitable for a young
woman, and don't forget the adhesive."
"Yes, Madam."
"Make sure they are the finest quality and the most realistic they
have. Never mind the cost. Also call in to Dr Burnley's office and
collect a prescription for hormones. I'll phone him later and arrange
it."
"Of course, Madam. Will that be all?"
"When you have finished washing our undies, I'd like a manicure, then
you can wash and set my hair. I expect Leon would like a manicure too."
She ordered.
"You know," she mused, "now that you are getting tits and becoming a
grown up woman, we can't keep calling you Leon. From now on you will be
Leonora. What do you think Alison?"
"A lovely name, Madam. It suits her perfectly."
Leon
Leon couldn't wait for Alistair's return from his shopping trip. He had
been imagining how he would look and how the breast forms would feel.
He'd already carefully selected the clothes he proposed to wear, paying
particular attention to the bra. He'd decided on a tight fitting
cashmere wool jumper and wool skirt, dark tan stockings, and lowish-
heeled shoes. He would wear a brand new bra and panty in apricot satin
with white lace trim. He had bathed, and powdered and now sat waiting,
with mounting excitement, in one of Chrissie's negligees.
Alistair eventually returned carrying several boxes and bags. Leon ran
to him as soon as he entered the apartment.
"Did you get them?" He nodded. "Let me see them, please. I can't wait."
"All in good time Miss Leonora. Let me at least get through the door."
He said smiling at his eagerness.
He took an age unpacking the groceries; stowing things into cupboards
and the 'fridge, but eventually it was done. He said, "Ok, into the
bedroom and strip to the waist." Leon needed no second asking. "Lie on
your back please."
Carefully Alistair positioned the breast forms in exactly the correct
place and marked their position with a felt marker pen. He then mixed
to contents of two tubes together and applied the adhesive to the back
of the forms and to the skin of Leon's chest. When the glue felt dry to
the touch he placed the breasts on the marks and pressed them firmly
down.
"You mustn't move for five minutes until the adhesive sets properly."
The five minutes seemed interminable till Alistair told him he could
get up and look. Leon gazed into the mirror in spellbound silence. His
mouth fell open in awe, never had he dreamed of possessing such a
perfect bust. The forms were indeed the best that money could buy. They
had the weight and texture of real flesh; the warmth of his body heated
them to his natural body temperature. The nipples were prominent and a
brownish pink. When the forms were first attached they had a curious
opaqueness that gradually assumed the colour and tone of his skin, and
the edges were clear, allowing his own skin colour to show through,
thus hiding the join. After a few moments they became indistinguishable
for living flesh,
Slowly he brought his hands up and cupped his new breasts, squeezing
them softly. Suddenly he took his hands away and starred at the palms.
"I don't believe it, Alison," he cried. "I swear I can feel myself
touching them. It's as though they are real skin, and look my nipples
are getting hard."
"Yes, Miss Leonora, indeed you can. You see it's all in the adhesive.
It is a special formulation that allows the nerve endings in your skin
to bond with the artificial skin of the breast form. The same process
also connects your real nipples to the false ones allowing you the
sensation of feeling that they part of you. So for all practical
purposes they are real. And the glue is extra long lasting and will not
come unstuck under any circumstances. The only way to remove them is
with an antidote."
"Wow!" was all he could say.
"Now get dressed and let's see what you look like."
Later, when Alistair had left for the office, Leon spent the day trying
on various bras, dresses, tops and blouses. He'd leave several buttons
open and practised leaning forward to expose his cleavage. He would
stand side-on to mirrors and admire his new figure. He couldn't keep
his hands from caressing his breasts and marvelling in the exquisite
sensations he felt. He loved to stimulate his nipples so that they
became prominent and made an obvious bump under his clothes. He was in
a constant state of erection. Three times during the course of the day
he masturbated as he watched himself play with his new treasures. He
couldn't wait to show Chrissie when she came home.
Christopher
The sight that met Chrissie as she entered the apartment that evening
stopped her dead in her tracks. Standing in the hall dressed in a
little black cocktail dress, 4" strappy black sandals, a diamante
chocker and dangly crystal earrings was a living image of her mother as
she'd been when Chrissie was Leon's age. The similarity was uncanny.
Apart from the age difference they could be the same people. Her mind
suddenly flashed back to when she was a teenager and her mother had
owned a dress that was very similar to the one Leon now wore. It had
been her favourite and she loved her mother wearing it.
"Do you like it?" Leon asked, suddenly doubting that he had done the
right thing.
After a long pause and shaking her head in wonder she said, "Oh.
Leonora. You're beautiful. I never would have dreamed you could look so
lovely. Come here and let me kiss you."
They chatted excitedly while Chrissie showered and changed her clothes.
Leon explained about her breasts forms and how Alistair had attached
them, and how he'd fixed her hair and make-up so that he would make a
good impression when Chrissie got home.
"I hope you don't mind, but I borrowed this dress from your closet?"
"Not at all, you know you are welcome to anything of mine. So now that
you really do look like a lovely young girl we must go out and show you
off." Chrissie announced when she was finished dressing. "We'll go to a
swanky restaurant and get something to eat, then go on to a night club
I know. You look too good to hide away."
"Oh, I couldn't. I've never been out in public before. I'll be too
afraid someone will find out I'm a boy wearing girl's clothes."
"Nonsense! No one could possible know that you are not exactly what you
appear to be. I'll look after you. It'll be fun. Come on."
Telling Alistair to get the car she took Leon's hand and they followed
him from the apartment.
They went to a very discreet and expensive restaurant that she often
frequented. The Maitre D. was delighted to see her and seated them at
her usual table, presented them with menus and took their drinks
orders. Leon began to relax when he realized that the looks he was
getting were of admiration and not curiosity. When the headwaiter
complemented him on his appearance he almost purred.
"Marcel, I'd like you to meet my daughter, Leonora. Leonora say hello
to my good friend Marcel."
Chrissie could have bitten her tongue. What had possessed her to
introduce Leon as her daughter? Sister would have been better. Half
sister would have been better still. Although for complete accuracy
half brother would have been correct but it would of course be
impossible to go into that. Ah, well, too late now.
"Enchanted, Mademoiselle." He said, taking Leon's hand and kissing his
fingers. "But surely Madam is too young to have such a beautiful
daughter."
"Oh you old flatterer, you. She's has been away at finishing school and
has now come home to join the firm. So I expect you'll be seeing a lot
more of her."
They ate a wonderful meal starting with smoked brown trout, followed by
quail in aspic, asparagus shoots, and duchess potatoes, and finishing
with a delicious mint sorbet along with a bottle of Chateaux Palmer
'74.
They left to more compliments and admiring glances. Alistair, who had
waited in the car during their meal, drove them to 'Deceptions', a club
for crossdressers and transvestites run by two friends of Chrissie's.
She didn't explain to Leon the nature of the club but introduced the
owners, Emily and Pattie as two old girl friends.
They found a table near the tiny dance floor and ordered drinks, and it
wasn't long before a handsome middle-aged man approached and asked if
Leon would like to dance. He turned to Chrissie with a look of panic on
his face, but Chrissie nodded her head in encouragement and squeezed
his hand reassuringly. As she watched the couple dancing, a puzzled
expression came over Chrissie's face. She was sure she'd seen him
before somewhere. The more she looked the more convinced she was that
she knew the man. But his name would not come. She tried not to think
about it knowing it would be bound to come to her later.
Pattie sat down beside her and asked excitedly. "Who's your new
girlfriend? And don't give me your daughter bullshit, I know you better
than that."
Chrissie explained exactly whom Leon was and how he came to be staying
with her. She had introduced him as her daughter in an effort to give
him some confidence. It was his cross-dressed debut after all.
"She's divine." Pattie gushed. "I'd love to get my hands on her. Better
keep an eye on her though, some of the old queens in here will eat her
for breakfast."
"Incidentally," Chrissie asked. "Who's the guy dancing with her? I'm
sure I know him from somewhere."
"I'm not sure. He comes in every so often. Usually he's alone. I'll
find out and let you know."
Just then Leon and his partner returned. He bowed gallantly and thanked
him for the dance. Then turned to Chrissie and asked if she would
honour him with the next one. Leon quickly leaned across and grabbed
Chrissie's wrist and frantically whispered in her ear, "We have to go.
Please." He pleaded. "Take me home, it's important."
"Another time perhaps," she said to the man. "I'm afraid my daughter's
not feeling well and we have to leave."
In the car Chrissie asked with some concern, "What's the matter, I
thought you were enjoying yourself?"
"Oh, I am." He giggled, slightly drunk. "It's just that guy. I've never
danced with a man before and he had his hands all over me," he
hesitated, "and I could feel he was hard, he kept pressing it against
me."
"Are you surprised? You're a very desirable woman."
"No. That's not it. You see I liked it. It excited me. I enjoyed the
feeling of being wanted by a man. To know his erection was because of
me and that he wanted to fuck me." He was blushing furiously now, "I
was hard too," he confessed. "Is that a terrible thing to say?"
Before Chrissie could formulate a reply Alistair stopped the car in her
parking slot. They rode the elevator up in silence. Entering the
apartment Chrissie told Alistair to pour a nightcap for them, and then
he could retire.
Kicking off her shoes Chrissie sat on the couch and indicated for Leon
to join her. They sipped their drinks together for several minutes.
Chrissie half turned and faced the lovely young woman beside her and
said.
"It's perfectly natural for you to feel the way you do and it's nothing
to be ashamed of. If you want to act and live as a woman then you are
going to have to learn how to make love to a man."
"Yes I suppose so. I hadn't thought it through properly." He paused,
thinking. "Being held in his arms seemed so natural. It felt so right,
so perfectly normal. Having his strong arms around me made me feel safe
and secure."
"Come here." Chrissie said taking him in her arms and kissing him
tenderly. "I know I'm not a bloke, but I can show you how to please a
man. We girls have certain tricks and items we use. Would you like me
to show you?"
For an answer he only nodded his head. Chrissie took his hand and led
him to her bedroom. "Take off your dress and jewellery and I'll be back
in a second."
In the bathroom Chrissie stripped to her skin and lubed her anus with a
liberal quantity of KY jelly. She donned a heavy silk nightdress then
checked the mirror to ensure her erection wasn't visible through the
material. From a cupboard she took a strap-on dildo, several condoms
and new tube of lubricant. Entering the bedroom her breath was again
taken away by Leon's shear beauty. He stood in partial shadow beside
the bed, the startling whiteness of his lacy bra and panties standing
out. He'd removed his garter belt, stockings and shoes and appeared a
little unsure of what to do next. Chrissie held out her hand to him and
he walked round the bed and took it. She hugged him to herself and
kissed his mouth.
"I'm a bit nervous," he whispered.
"There's no need to be. I was too my first time, but don't worry I'll
be gentle with you. Do you know what this is?" she asked, holding up
the dildo by the strap. He shook his head in the negative. "It's what
we girls use when there are no men around. It's an artificial penis,
commonly called a dildo. It's very life-like; it has the texture and
warmth of the real thing and the testicles discharge at climax. Here
take it and feel for yourself."
He took the object from her, one hand cupping the scrotum and the other
grasping the length as though about to masturbate it. He looked at it
closely examining the head and urethra. He'd never before been as close
to an erect penis, real or phoney. His tongue wet his lips and she
thought he was about to put into his mouth.
"You handle it like you know all about it." she said. "Put it in your
mouth and suck it. Pretend it's the real thing and you want to give a
guy some pleasure." He did as she said. "Yes that's it. You're a
natural. Swallow it as far as you can. Try to open your throat and take
it all the way to the balls. Now pull back but maintain the vacuum and
work the tip of your tongue into the hole, men love that. That's it,
get lots of saliva on it, it'll make it easier to enter."
While she educated him in the art of fellatio she manoeuvred him over
the arm of the chaise lounge. Kneeling behind him she slowly lowered
his panties and removed them. Her hands caressed his bottom cheeks and
her thumbs spread them apart. She gazed in wonder at his beautiful pink
ring before invading the virgin hole with her tongue. She tongue-fucked
him for several minutes thoroughly moistening his tunnel. She could
hear him slobbering and moaning and judged the moment right. Standing,
she reached forward and took the dildo from his eager mouth. She raised
her nightdress, grasped her aching member and placed the head on the
spot her tongue had been a moment before. Easing her hips forward she
entered him and sank her full length into him in a single movement. She
was surprised by how easy it was. He must be totally relaxed she
thought and not expecting it. She felt his rectal muscle tighten and
grip her rod as she lay on his back buried inside his hot back passage.
"There that wasn't so bad was it?" she whispered into his ear. "Just
relax and enjoy it."
She slowly withdrew half her length then pressed forward again. She
felt him start to move against her. Her rhythm increased and soon she
was stroking her full length in and out of his rectum. His groans told
her he was not averse to being anally fucked so she quickened her tempo
till she was pounding his arse as hard as should could. Reaching round
his hips she gripped his twitching cock firmly in her hand, squeezing
it tightly. The touch of her hand was enough to trigger his climax. His
cock bucked in her hand and ejected a large dollop of white spunk. He
shrieked and spurted three more times. His ejaculation touched off
Chrissie's eruption. She climaxed pumping a huge quantity of sperm into
his depths.
It took several minutes for Chrissie to recover her breath sufficiently
to breathe easily again. She withdrew her dripping, flaccid cock from
Leon's arse then flopped onto the couch exhausted. She made sure he
wasn't aware a real penis had fucked him by covering herself carefully
and holding the dildo in her lap as though she had just used it. Leon
turned and sat beside her, his limp penis flopping onto his stomach.
"Oh, Chrissie," he gasped. "That was wonderful. I have never felt
anything so good before. Thank you."
"I'm glad you enjoyed it." She replied.
"But you didn't get enjoyment from it," he said, suddenly concerned
that he had had all the pleasure and she none. Little did he know. "Can
I do something to make you feel good?"
"You're very sweet," she said. "I'd love you to fuck me, but you will
have to do it the same way that I did it to you. You see I have my
period so I can't let you fuck my cunt." She lied.
"That's Ok," he said. "I don't mind. I just want to please you, but you
will have to help me, it's my first time."
She was amazed to see that he was hard again and eager to start. She
got onto her hands and knees on the couch, raised her nightie over her
waist and presented her luscious naked buttocks to him. She positioned
him between her legs and guided his rigid cock to her hole. She was
taken by surprise as he lunged straight into her burying his lust
filled spear to the full. She was glad she had lubed earlier because he
immediately began pumping into her anus. Plunging in and out as though
there was no time to spare.
"Slow down, Leonora," she urged. "Take you time. Stroke it into me
slowly. Pull out till only the head is inside me then push forward as
far as you can. Yes, that's good. Keep it going. Slowly out and slowly
in. Deep, long stokes. Mmmmm yes, that's lovely. Now you can increase
your speed a bit, not too much. Yes that's perfect."
She was impressed with his vigour and stamina. He continued to fuck her
as she directed for many minutes without any sign of flagging or
cumming. Her own prick was painfully hard again and she masturbated
herself as he ploughed her anal canal. As she felt her climax approach
she urged him into a gallop for the final furlong.
"Yes now," she cried. "Come on Leonora, fuck me hard. Shoot your spunk
deep inside me. Fill me up with your hot cream."
As she felt her bottom being filled with liquid her pumping hand
brought forth her own bounty, shooting it onto the seat of the couch.
Leon emitted a guttural scream from deep in his throat, thrust hard
against her, ramming the last millimetre of his cock into her and
collapsing onto her back, forcing Chrissie flat onto the seat. They lay
together, panting till they gradually recovered. Leon's dick shrank and
slid from her greasy anus. She told him to go and shower then dragged
her own abused body across the room, flopped onto the bed and slept.
Leonora.
Leon's confidence grew by the day. He now dressed as a girl nearly all
the time. He felt so much more relaxed when en-femme than when dressed
in boy clothes. The soft silky fabrics seemed to eliminate all his
aggression and surliness and he became a sweet natured, pleasant
individual. He loved the rituals of make-up and hair care, the dilemma
of whether to wear a dress or blouse and skirt and the endless trying
on of different outfits. With full access to Chrissie's extensive
wardrobe the daily decision of what to wear seemed to take forever. He
loved the pampering Alistair gave him whenever he was not working for
Chrissie. The manicures, pedicures, eyebrow plucking and the skin care
products he used on his face and body. He loved to parade different
ensembles for Alistair to inspect and valued his advice. Most of all he
just loved everything feminine and girly.
He had taken to venturing outside in the afternoons, walking a little
farther each day, exploring the world through girls' eyes. Chrissie had
left on one of her business trips so he was bored and restless.
Wandering aimlessly along a street he suddenly stopped before a shop
window and stared at the most beautiful pair of shoes he'd ever seen.
The black patent-leather ankle booties had fourteen tiny silver buttons
running down the inside leg of each shoe. The 5" stiletto heels had
silver tracery chased into the leather and the pointed toes were also
silver capped.
"Gorgeous aren't they?" a voice said.
Leon jumped in surprise. He had been so involved looking at the
footwear he was unaware of a person standing behind him. He turned and
recognized Pattie from the club they been to a few nights previously.
"Oh they're beautiful." He responded.
"Would you like to try them on?"
"I'd love to but I don't think I should. I'd be embarrassed."
"No need to be," Pattie said. "Come on I know the woman who owns the
shop."
Taking Leon's hand she led him inside. The place was empty except for a
smallish, grey haired woman who was folding clothes behind the counter.
Looking up from her task she said, "Hello, Pattie. Nice to see you."
"Hello, Mrs Pettigrew. I'd like you to meet Leonora Marcus. She came to
the club the other night with an old friend of mine and was a huge
success with all the men." She teased.
"Hello, Leonora, how can I help you?"
"She'd love to try on the shoes in your window." Pattie said before
Leon had a chance to speak.
Mrs Pettigrew moved to the window, lent in and retrieved the shoes.
"They are lovely," she said. "Here you are my dear sit down and let's
see if they fit."
Leon sat on the only chair and removed his loafers. Pointing his toes
he slid his foot into the opening, held the two sides and pushed. His
big toe made contact with the front before his heel slid down. They
didn't fit. He pushed and scrunched his foot into the shoe in a vain
attempt to force them on. No good.
"Oh what a pity," said Mrs Pettigrew, "but never mind, I have more that
I'm sure will fit you. Let me get them."
"No. It's quite all right; it was those that I wanted. Anything else
wouldn't do."
Pattie could plainly see the disappointment on Leon's face. "Never
mind," she said, "I've an id