[continued from previous message]

that Donald could stroke her cheek. She stepped into him and pressed
herself against him and he enveloped her into his arms.

This kiss was also tender and gentle at first but soon their passions
ignited and Julie clung to him as he kissed her with raw passion and
desire. She felt safe and secure in his embrace; his toned body pressed
against her delicate frame. The root of his manhood thickening against
her as the kiss became fervent; mouths opening, tongues intertwining,
breathing haggard with desire. Julie was becoming uncomfortably
tumescent, her penis swelling, trapped between her buttocks.

"You are a beautiful little minx," Donald gasped when they finally broke
the kiss.

"Do you want to go upstairs," Julie sighed demurely, catching her breath.

Donald knew what that meant and yes he wanted desperately to take this
woman upstairs.

He followed behind her his eyes glued to her buttocks swathed in that impossibly tight skirt. The kick-pleat opened and closed as she
ascended, providing him with glimpses of her stocking-sheathed thighs.
He had developed a wet patch in the front of his trousers and he'd had
to adjust them to cater for the erection growing in his underpants.

Julie led Donald into the workroom and they began to take up where they
had left off downstairs; kissing each other, at first tenderly and then
as their passions built, more eagerly and lecherously.

Julie felt tiny in his embrace and Donald was scared that he might hurt
her but he wanted to hold her close. Julie nestled into him, fitting
into him like a jigsaw piece, perfectly aligned to his frame. He had to
lean down to kiss her and her head was tilted upward to meet his. She
felt like a damsel in a movie, being held by her paladin. Julie imagined
that she was the damsel in distress in one of the many books she had
read and Donald was her white knight.

She knew that it was a foolish thought. He was merely a man who had paid seventy pounds so that he could have sex with her but her imagination
was rife and if the illusion made it more palatable then let it be so.

Donald had rid himself of all thoughts of Julian; there was only Julie
ever since he walked through the door and seen her and he couldn't
believe how captivated he was by her. She fitted against his body
perfectly, one arm around his neck, the other around his back, holding
him close, one long leg hooked around his so that she was moulded to
him, her lips pressed to his. He smelled, he tasted her, he heard her
shallow breathing, but most of all he felt her and she felt wonderful.

He caressed her buttocks through her tight skirt, the fabric hissing
against her satin knickers, the contours of which he could feel with his fingertips. He desperately wanted to touch those knickers. Somewhere
deep inside his subconscious he knew that Julie would be different down
there; there were things in her knickers that weren't exactly womanly
but he wasn't repulsed. In fact he was inquisitive and excited.

Julie felt him squeezing her buttocks and she liked it. That's not
right... she loved it. Most of her punters played with her arse of
course and sometimes she liked it and sometimes she didn't but she was delighted with Donald doing so. He had a way of squeezing and caressing
her buttocks that was both forceful and affectionate. She slipped her
tongue a little deeper into his mouth and showed her appreciation by
wriggling against him.

She could feel the heft of his manhood pressing into her; his phallus
hard long and proud, generating its own heat; its own life force. Julie
wanted to touch it, to squeezed it, to stroke it, to put in her mouth
and suckle it and dare she say it... she wanted to feel it pressing on
her puckered bud. She'd be too scared to take it inside her; it was too
big and would tear her apart but the very idea of having that mighty
prong pressing dangerously on the entrance between her legs was what
excited her the most.

Knowing full well that she would never let him enter her made her feel
safe while she relished the fantasy of it.

Donald had moved his hand under her skirt and was exploring the welts of
her stockings and the delicate fair skin above them. This was Donald's territory and he caressed, tickled, stroked and manipulated Julie's
thighs in ways she had never thought imaginable. Her cock was rock hard
and trapped uncomfortably between her legs. It ached for release.

Donald had enjoyed immensely caressing Julie's lovely buttocks and of
course he had relished stroking her stocking-sheathed thighs. He adored
the feel of her silky hose on his fingertips. He'd traced the backseams
of her stocking with his forefinger; he'd stroked the dark bands of the
welts at the top of her stockings and had savoured the soft cool flesh
above the welts after spending time tinkering with the silver clasps of
her garters.

Now his fingers had found the lace trim on the legs of her knickers and
were about to explore further. This is where Donald thought he might
have a problem and Julie sensed his hesitation.

She had never ever wanted a man to put his hands on her knickers as much
as she wanted Donald to do it right now. To stroke them. To caresses
them. To slip his fingers inside them and find her penis hard and
bloated and pressed to her perineum.

Julie melted in his arms when he did exactly that.

Donald slipped his fingers inside the laced gusset of her full-cut satin knickers and found a perfect V in the front of them but of course there
was no mons or labia. Instead his fingers forged on and found her fleshy appendage hard and throbbing, trapped between her legs. He freed it and
the organ sprang forward and filled her knickers. Donald wrapped it in
the silky satin of her panties and stroked it.

Far from being repulsed, his cock began to throb. It excited him so hear
Julie gasp into his mouth, and writhe and wriggle as he pleasured her.
His own cock was demanding attention too.

A single tear ran down Julie's cheek when Donald freed her penis and
began to stroke it through her knickers. She was terrified that he would
be repulsed by what he found in her panties. She knew that it was his
first time with a transvestite and while some men were raptured by the
idea of being with a 'special girl', some of them were horrified by the
reality of it when they actually touched her genitalia.

But Donald hadn't done that. He was caressing her tender root, he was
kissing her harder, he was holding her tighter and she could feel his
cock throbbing against her. He was enraptured with her and she with him.

She sensed his urgency and she snaked a hand between their bodies and
freed his cock from the confines of his trousers. Her small hand could
just contain it. She felt the velvety softness of the thin dermis
covering the hard erectile tissue; she traced the veins with a
fingernail, sensing the blood coursing through them, filling Donald's
cock to make it into the hard, phallic weapon that it had become.

The pad of her fingertip circled his fraenulum while her other fingers
lightly caressed his glans. Julie heard Donald gasp and felt him shiver
with delight. Then Donald slipped his hand inside her knickers and
caressed Julie's penis in an almost identical manner and she began to
shake with the delirium of pleasure he was wrenching from her sensitive
organ.

She fell backwards onto the bed and Donald went with her, lying on top
of her, covering her with kisses. He pulled her hand out of the way and
hiked up her skirt and pressed his penis against hers. Both cocks began
to release pre-ejaculate. The feeling of their most sensitive organs
pressing and rubbing against each other ignited a flame inside them both.

Donald kicked off his shoes and managed to rip off his trousers and his
shirt with Julie's assistance. They achieved this somehow hardly
breaking their kiss. They clung to each other, grinding against each
other. Julie lay underneath his hard muscled body, feeling the raw power
in him, feeling his manhood pressing against her pulsing penis while he
kissed her, his hands alternated between squeezing her buttocks and
stroking her thighs.

She was still fully dressed with just her skirt hiked up and her
knickers pulled aside to expose her cock which was being massaged by
Donald's bigger, more powerful organ. They kissed and Julie wrapped her stocking-sheathed legs around Donald's torso and crossed her ankles
behind him and locked her hands behind his neck.

She rose up off the bed to meet his thrusts as they ground against each, rubbing cocks, kissing, caressing and experiencing a blissful sensory
overload. Donald mistimed a thrust and his cock lunged between Julie's
legs, it pressed on her perineum, the underside of his penis caressed by
the sleek satin of her knickers. It felt delightful for them both.

Julie was a little frightened when Donald's big cock began to press on
the soft smooth flesh between her legs, his glans dangerously close to
her sphincter. The harder Donald thrust, the closer his cock came to the entrance of her anus.

"You can't fuck me," Julie was able to whisper quickly before she
returned her mouth to his and kissed him deeply.

She had to admit that it felt glorious to be lying on her back with her
arms and legs wrapped around this strong, handsome, powerful man whilst
his turgid phallus grazed the sensitive space between her buttocks, his
penis sometimes pressing on her sphincter. Rings of pleasure radiated
from her groin, her mouth and her body.

Donald felt Julie's stockings rubbing on his flanks and it delighted
him, as did the feel of her heels grazing his back as they rocked
together on the bed. Her fingernails were scratching him but they were
lightly sensuous and produced a buzzing pleasant sensation that ran down
his back and linked with the gratification he was feeling as his cock
rubbed on Julie's tender flesh.

His penis was at full girth, ready to explode. His glans kept hitting
Julie's tight sphincter and he wanted to enter her even though she had
told him no.

He'd spied the tube of KY Jelly that Julie had left on the nightstand;
the same lubricant that Julie had used on the little dildo she had
inserted inside her back passage earlier in the evening. Donald's cock
was many times bigger than the dildo but Donald didn't know that.

He reached for the lubricant with every intention of greasing up his
manhood and piercing her and then he realised how selfish and cruel that
would be. It would be an act of betrayal and she would likely refuse to
see him again and he wanted to see more of this special woman... lots more.

Julie felt Donald's thrusts becoming more urgent; his glans pressed on
her sphincter and on one or two occasions it opened her just a little.
She would be lying if she said it didn't hurt when he did that, but even
her little dildo hurt at first when she used it. She wondered what it
would be like to be taken like a woman. What it would be like to feel
Donald's penis deflower her. She recalled the passages in The Story of O
where O finally surrendered her anal virginity to her master. She
shivered at the very thought of it.

Donald knew that he was being selfish by betraying Julie's trust so he
stopped trying to force his penis into her sphincter and instead
relished the feeling of his cock rubbing between her buttocks. He could
feel Julie's cock against his hard belly, leaking an almost continual
dribble of pre-ejaculate and he sensed that like he, she was close to
extremis.

Donald sighed and reached out to put the KY Jelly back on the nightstand
and just as he was about to release it Julie's hand clasped over his. He released the tube and Julie took it from him.

She looked up into his eyes, her own beautiful green eyes filled with uncertainty, devotion and also he thought, perhaps love.

"Be gentle," Julie whispered and squeezed a good dollop of the slippery
clear lubricant on her fingers and found Donald's erection and slavered
it with the salve.

She adjusted herself a little, raising her buttocks higher off the bed
until Donald's glans was nestled in her puckered bud. She locked her
hands behind his neck and scissored her legs on his torso and looked at
him one last time with devotion and trust in her eyes and then she
closed her eyes and kissed him hard and pushed upward and Donald's cock
slipped into her tight back passage.

It was as well that Julie was kissing Donald because it stifled her
scream as his huge penis split apart her tight puckered bud. Donald felt
Julie shudder with the pain of it and her smothered screams reverberated
around his mouth, her heels thrummed on his back and her body convulsed.

"I'm so sorry darling," Donald whispered.

He only had the tip of his penis inside her tight passage but he could
tell that the pain was excruciating. He attempted to remove the
offending appendage.

"No don't! I want it Donald. I want it so much. I want you," Julie sighed.

Donald's penis felt like a red hot poker had been pushed inside her
tight anus but the pain was tolerable after the initial sting and
tearing sensation and it slowly became a dull throbbing ache.

But there was something else.

Her stretched sphincter was radiating little sparklets of intense
pleasure. It was like when she used the dildo on herself but a hundred
times more intense. The feel of Donald's fleshy rod piercing her tight
virgin anus was indescribably pleasurable despite the accompanying pain.

"Let me, please," Julie whispered as she clung to Donald and leaned up
and kissed him softly.

He gazed into her emerald green eyes and saw the pain and watched her
wince and grimace, he felt her body recoil and shudder as Julie slowly
skewered herself on Donald's steely member. The feeling was
indescribably wonderful as her tight, greased hole opened up to envelope
and clench his turgid phallus. It was like his cock was being gripped
tightly by a velvet glove.

The feel of Julie's tiny body under him, her silken limbs grazing his
tender flesh, her slippery satin knickers tickling his scrotum, her soft
lips kissing him, the smell of her, the feel of her was overloading his
senses. His heart soared with something he had never felt before. The
sacrifice she was making in order to deliver to him the most intense
pleasure he had ever experienced was unimaginable.

Julie had never felt so affectionate and cherished as she did lying
under Donald Cooper. She sensed his distress for the pain that he was
causing her but she needed to make him understand how wonderfully
content she felt as she slowly speared herself on his long thick penis.
Every inch that entered her caused her immeasurable pain but at the same
time infinite and unbounded pleasure.

Julie sighed with contentment when she finally had all of Donald inside
her. Her sphincter had finally relaxed and the intense burning sensation
was replaced by ringlets of decadence and contentment; her anus felt
stretched to full capacity but it radiated a deep throbbing resonance
that was almost indefinable. The glans of Donald's penis was pressing on
her prostate which emitted pulses of rapture that coursed through her
body, lighting up her pleasure centres.

Julie's cock was pressed against Donald's tight belly and every little
movement he made amplified the satisfaction she was feeling. Runnels of pre-ejaculate oozed from the eye of it and Donald felt it pulsing on his
flesh and it delighted him.

He leaned down and opened his mouth and kissed Julie with a deep languid
kiss, his tongue slipping inside her mouth, exploring it as she clung to
him, her nails raking his shoulders, her stocking-clad legs clutching at
him, her heels digging into the small of his back, girding him on,
encouraging him to fuck her.

Donald began to slowly thrust himself in and out of Julie's tight
passage and she whimpered under him, shuddering with the ecstasy of it, encouraging him, rising up to meet his thrusts as he grasped her
knickered buttocks in his hands and drove his steely cock in and out of
Julie's tight, greasy anus.

They climaxed as one. Julie felt Donald's cock swell inside her and then
then erupt, depositing his issue deep inside her as she simultaneously ejaculated against his belly. Waves of pleasure enveloped them both as
they clung to each other like shipwreck survivors on a tumultuous sea.
They kissed and moaned and held each other tight as Donald drove his
cock deep into Julie's bowel and gave her his seed. He felt her scalding
semen on his belly as she orgasmed right along with him, her heels
drumming on his back; he stifled her screams of pleasure with his mouth.

end p4

They lay sated and still, neither of them fully comprehending the magic
they had illicited from each other. Donald had never felt such a rush of indescribable satisfaction. His cock was still deep inside Julie's anus
and was still fully erect and he could feel Julie's penis pulsing gently against his belly as the last dribbles of her spunk leaked from it. Far
from feeling repulsed, he felt satiated and delighted.

Julie was incapable of speech. She felt like she had climbed the highest
peak of a jagged and dangerous mountain range and overcome pain and
suffering to experience the most exhilarating pleasure. She could feel
Donald's cock still buried deep inside her anus but she was no longer experiencing pain, only a deep pleasurable pulsing. She tightened her
sphincter around his shaft and Donald smiled down at her.

"Was that deliberate?" he asked.

Julie nodded.

"I didn't know I could do that," she smiled up him salaciously.

"Do it again," Donald whispered.

She grinned at him and did it again and pulled his face to hers so she
could kiss him while she used her legs and heels to encourage him to
fuck her a second time.

Later they lay in bed smoking, Julie stripped down to her lingerie and stockings and Donald naked, unable to stop touching each other tenderly
and softly kissing as they talked deep into the night. Donald told Julie everything about him. Julie listened, taking sips of her gin and tonic
as Donald told his tale. When he had finished she said nothing.

"Where's Julian?" Donald asked.

Julie froze.

At that moment she both loved and hated Donald. She hated him because he
had brought up Julian and he was the furthest thing from her mind. She
loved him because he spoke about Julian as if he was another person;
which to Julie he was.

Julie explained her complicated life to Donald, talking about Julian in
the third person as if he was another entity and the only thing they had
in common was the bookshop and a shared body. Julie told Donald that if
there was any way possible that she could live her life as Julie and
sacrifice Julian's existence she would.

Donald ruminated on Julie's story and got out of bed to freshen their
drinks and bring more cigarettes. He climbed back into bed and Julie
snuggled up to him and playfully jiggled his limp penis and Donald
unashamedly jiggled hers as if it was the most natural thing in the world.

"I think I wore him out," Julie giggled and kissed Donald on the cheek.

"I think so. You too," he let go of her flaccid ember and kissed her on
the lips and then lay back and stared at the ceiling contemplating what
he was about to say to her.

"So I told you that I'm a lawyer. Without bragging I'm a pretty good one
and pretty high up on the judicial ladder. I know a bunch of judges, magistrates and government officials who owe me many favours. I also
have contacts in a few of the more notorious underworld firms who can do
things for me that can't be done legitimately," Donald began.

"So?" Julie was puzzled.

"What if I told you that I could make Julian disappear and make you a legitimate person; a real woman legally if not anatomically, although
there are some improvements I can organise for you if you would like
them," he continued.

Julie snuggled up to him.

"Go on," she whispered in his ear.

Donald and Julie - London, December 1964

Donald packed his briefcase and on the way out of his office he stopped
to kiss Gillian Snodgrass on the cheek and wish her a merry Christmas.

"Merry Christmas to you too and give my love to Julie," Gillian smiled
at him affectionately.

"I most certainly will," Donald returned Gillian's smile.

Gillian was one of a very small group of people who knew about Julie's past.

Donald left the law office of Donald Cooper, Esq - Attorney At Law. He
had not regretted leaving Cooper, Stanley, Price and Waterman and
striking out on his own, taking Gillian Snodgrass with him as his
personal law clerk. His practice was thriving and things could not be
better.

His divorce with Deirdre was settled amicably and she had left England
to live in France with some French aristocrat who treated her like a
queen and he was happy for her.

He whistled as he walked down Piccadilly Circus and stopped outside a
familiar establishment and looked up at the gilt sign above the door. Clifford's Books and Sundries it read. Julie Clifford Proprietor it said
in smaller writing below the main sign.

Donald looked through the window and saw the love of his life tending to
the last customer of the day. The customer left the shop carrying a gift wrapped book and Donald nodded to him and slipped through the door,
switching the sign from OPEN to CLOSED.

Gone were the wigs and costume jewellery. She was wearing a stylish and expensive skirt-suit, her hair perfectly coiffed, the diamonds
glittering on her neck and dangling from her ears were real. The
identity documents in her purse were real; well real to the extent that
her existence could be verified in the government offices of her
Britannic Majesty.

Julie broke into a smile and ran to meet him, folding herself into his
arms like she was always meant to be there. Donald, as always, relished
the touch of his common-law wife. Julie had not long returned from
America where she had undertaken mammoplasty surgery and was proud of
her new breasts which she pressed against Donald as she smiled up him.

"Thought I'd let you cop a feel of the Christmas present you gave me,"
she winked at him salaciously.

"Don't talk so crudely Miss or I might have to spank you," Donald chuckled.

"You'll have to catch me first," Julie bolted from his arms and ran into
the stacks of bookshelves.

Donald caught a glimpse of nylon-stocking-sheathed calf as she ducked
around the corner and was immediately aroused.

He locked the door and chased after her.

The End

Author's Note: Thank you all so much for enjoying my story and leaving
your comments. An intellectual once wrote: "Writing should almost always
be a communication between writer and reader, and therefore feedback is
the best way to sample how that communication is developing." Kisses and
hugs to you all and I wish you all the best for new year.

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Post as:Anonymous
23 COMMENTS
BiSuzy65BiSuzy653 days ago
Once again, Michelle tops the list. What a wonderful author of trans
erotica she really is. I rarely drop by literotica these days but when I
do, it’s Michelle’s name I look for first. Xxx

Danielle_CD58Danielle_CD5821 days ago
Michele I put off reading this work for a while but finally succumbed. I
LOVE your writing but over the last couple of years I've leaned more
into romantic stories of this genre. You kit it out of the park. I love
this story. It is fantastic. Your attention to details (I've been
looking up words all through the story - LOL). and the character
development are fantastic. The love scene was beautiful. Thank you dear
for another good read (and maybe a couple of wanks, LOL).

Anonymous22 days ago
Geat story; really enjoyed it.

Anonymousabout 1 month ago
Amazing story, thanks for sharing!

eljaybeljaybabout 1 month ago
You write beautifully and with sensitivity, thank you

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