Bossed into panties - Part 6
Chapter 18
Honeymoon cuckolding
It was a long journey through the night to the Caribbean. Debbie,
travelling with Henry instead of her husband Peter, finally reached the
hotel and collapsed into bed around lunchtime. Whether it was the jet
lag, the shock of the events of the last twelve hours, or Henry's
constant attention, Debbie couldn't sleep. She stood staring out of the
open window, admiring the beautiful blue ocean and the fine sandy
private beach, wondering what Peter was doing right now. He should have
been with her of course... but thank God he wasn't, not after what she'd
discovered on their wedding night. She yawned and stretched. The short
wispy chiffon nightdress hugged her full breasts and the light sea
breeze caused it to flutter sensuously around her pale pink bottom,
revealing tantalising glimpses of exquisite loose-fitting sheer pink
panties.
Henry sat up in bed, blearily opened his eyes and observed the
magnificent sight before him. He licked his lips and felt his manhood
stir. There was nothing like seducing a girl on her honeymoon, he
smiled. He approached her luscious body from behind and wrapped his
powerful arms around her waist, pulling her to him and kissing the soft
warm skin on her neck. He began to massage her breasts, toying with her
nipples through the filmy chiffon until he'd brought them to full
erection, then moved down to play with her clitoris through the lace
trimmed panties.
"Mmmmm," she purred. She could tell he was naked. His manhood was
pressing urgently into her bottom, enjoying the feeling of the silky
panties pressing against his sensitive glans. "This is paradise, isn't
it Henry?" Little did she know that it happened to be Henry's home town
as well. "Oh Henry! Surely not again darling, I'm exhausted. Ooooooh I
can't get over the size of your cock, it's huuugge... mmm.... are you
black guys all the same," she laughed.
"Wouldn't you like to know," he laughed.
"Oooooh God.... mmm I could never go back to white after this.... oooh
that's lovely." He'd already made love to her three times since they'd
arrived. Neither of them had had much sleep, and they'd had little to
eat since leaving the UK apart from airline food. Once again, he was
ready for her, his stiffening cock working easily up inside the loose
fitting panties, searching for that warm tight cleft between her
buttocks. She loved the way his cock teased her bottom, but this time
there was to be no foreplay. He was on fire and quickly at the entrance
to her sex. She was nicely lubricated from their repeated lovemaking and
with one slick movement, he slipped inside her and thrust his hips
upward, taking her weight with his powerful arms and lifting her fully
six inches clear of the floor.
"Oooooooooh," she yelled, impaled on his engorged member. He'd taken her
breath away and the sheer depth of his penetration was mind blowing. Her
leg muscles tensed and her toes pointed down to the floor as she moaned
softly and danced about on his sex. He let her down gently and withdrew
a few inches of his manhood but as soon as her feet touched the ground
he was once again thrusting deep inside and lifting her clean off her
feet. "Ooooooh," she yelled. "God, you're such an animal.... ooooooh....
Peter never took me the way you do."
"Isn't it better to be enjoying your honeymoon like this, than with some
panty loving sissy, flouncing around in a dress?" Henry groaned,
thrusting his black shaft deep inside her.
"Oh yessssssss," she cried out with the pleasure and release of several
weeks of pent-up frustration. Her fianc?e Peter, had no idea when it
came to pleasing a girl in bed, and prior to the wedding she'd been
without sex for so long that she was desperate to make up for lost time.
She could feel herself cumming but it was far too soon. She begged him
to slow down.
"Ooooh Henry, I don't think I could ever get tired of feeling you inside
me but I want to make it last, darling. Let me get into a more
comfortable position, please."
Giggling like a little schoolgirl, she slipped her panties down and
kicked them away. Then, reaching for the window sill, she bent over and
thrust her milky white bottom up into the most compliant and submissive
of positions for him. She giggled softly as she wiggled her buttocks,
sensing the effect she was having, and positively inviting him to take
her. He hardly needed the invitation, wedging his powerful thighs
between her long legs and splaying them wide. With his strong hands, he
gently prised her buttocks apart until she was presenting her smooth,
nicely lubricated, and very obliging cunt. It was prominently displayed
and the perfect height for his probing weapon. He teased her pussy lips,
testing the entrance with his glans as her wriggling movements spurred
him on.
"Oooooh yes, make love to me again Henry," she pleaded. She loved it
when he took her from behind, it was so base and animal like.
"God I'm so horny. Take me slowly, and give the bride a lovely, deep
fuck.... ooooh.... ooooh that feels soooo good," she cried as he sank
his thick root, deep inside her.
He loved to hear her begging for it and began a familiar slow rhythmic
sawing into her pussy, as she pushed back to meet every thrust. Her eyes
closed in ecstasy and she barely noticed he had her nightie up round her
neck. Her breasts sprung free of their restraint and dropped into the
palms of his hands allowing him to tweak the hardening nipples. She
moaned softly and closed her eyes as his powerful thrusts gradually
propelled her toward the window. The top half of her body was literally
hanging outside with her huge breasts swinging freely in the warm air.
"Oh you're such an animal," she gasped.
"Oh Henry... mmmm.... ah.... ah.... ah.... ah... oh that's wonderful....
mmm .... oooh." Then as she opened her eyes she stopped in her tracks.
"Jesus... Henry! Henry, there's people outside on the beach... looking
at us.... stop it! Henry, STOP IT!" she shrieked.
Less than twenty yards away, there were two local boys, strolling along
the deserted and private beach. They were lean and well muscled, and
wore the tiniest of swimming trunks, little more than a thong. They
stared at the white girl leaning out of the window, her fabulous breasts
swinging appetizingly back and forth, and in the shadows behind, a tall
black male taking her forcefully from behind.
"That must be the honeymoon cottage then," one of them laughed.
"Yeah, and that must be the bride! Oh man look at those big white
melons! That's a sight for sore eyes," the other laughed, as they
watched the look of panic on the girl's face as they approached.
"Henry, stop it... they're coming this way. Look! I'm not kidding!" she
shouted, struggling to break free of his firm grip.
Henry waved and beckoned the young lads toward the cottage whilst using
his powerful thrusts to move her forward until her thighs were wedged
firmly against the wall, and her naked breasts were swinging freely
about a foot above where the boys were now standing. She was trying to
use her hands to cover her breasts but Henry grabbed her wrists and
pulled them back, providing even greater leverage for the shafting he
was giving her.
One of the lads reached up and grabbed a pendulous breast as if he were
picking a juicy apple. Debbie yelled. She was struggling like crazy but
Henry seemed determined to finish what he'd started, and he was still
slamming into her ass when the door opened and the two boys casually
walked in.
"Hi man, how you doing." They smiled and went for high fives with Henry.
They obviously all knew each other and the young lads weren't in the
least surprised to see Henry making love to the girl. "Meet my younger
brothers," Henry panted. "We're all family here," he laughed at her look
of shock.
Henry came inside her with one final thrust and let his cock slowly pump
another batch of fresh semen toward her womb. "Oh babe," he groaned
contentedly. "Man, I needed that. She's one hot bitch," he told the
boys, suddenly showing her no respect whatsoever. "Can't get enough of
it, can you babe?" Henry withdrew his large weapon and introduced his
brothers. Debbie was dumbstruck. One minute he could be so tender and
caring, the next he was inviting his family in to watch them make love.
"So this is the bride then. All hot and sexed up for your honeymoon are
you?" Leroy, the elder of the two boys chuckled as he looked her over.
Debbie nervously pulled the hem of the baby doll down, trying to hide
her sex, and placed her hands over her breasts. She was terrified. "You
sure she ain't pregnant? Look at the size of those titties," he said
incredulously, reaching out to touch them. Debbie quickly slapped his
hand away. "Man, they're huge... especially for a white girl. Yeah,
they'll do very nicely," he grunted, pulling her hands away. As she
struggled to fight him off, he began to maul her through the wispy
material.
"Get lost. Get your filthy hands off me," Debbie shouted, pulling away.
"You touch me once more and I'll scream the place down." They were some
way from the next cottage, but the boys immediately shut all the windows
and Henry carried her kicking and screaming toward the bed..
"Sssssh babe, there's nothing to worry about. We're all part of one big
happy family here. Share and share alike, especially on your honeymoon,
that's the tradition out here."
"So how was the wedding night?" Leroy asked as Henry settled her onto
the bed, still struggling.
Henry laughed. "You should've been there, man. What a sight. The bride
and groom on their big night," he laughed. "I was giving Debbie a good
seeing to and right next to us on the bed was her sissy husband. You
won't believe this. They had him all dolled up in Debbie's big white
wedding dress and all this frilly stuff underneath."
"No shit! He was wearing her underwear?"
"Oh yeah, you should have seen it. Petticoats, stockings, the whole nine
yards... he was even wearing your sexy little see-through panties,
wasn't he babe?" Henry grinned.
Debbie suddenly felt very red and embarrassed. After all, it was her
husband they were talking about and it made her look a complete idiot to
have married him.
"So there they both are, the bride and groom kneeling on the bed. Me
giving her a nice length, and right next to us there's her husband with
the skirt up round his waist and this guy pounding his ass," he roared.
"And the funniest thing.... he was getting off on it too. Inside her
flimsy little panties he had a raging hard-on. Can you imagine... having
a hard-on while some guy rams his dick up your ass?"
"Oh man, that's evil," Leroy burst out laughing. "Well the wedding night
ain't finished for you yet sweetie," he laughed at Debbie. "I hope she's
fertile?" he asked his elder brother.
"She came off the pill before the wedding, didn't you darling? Yeah,
she's ripe for breeding alright," he laughed as she lay pinned under his
strong arms. "Hot and broody, and ready for plenty of cock. Just how we
like ?em, eh boys?"
She looked up in total shock as the boys giggled and slid their tiny
trunks down, revealing good sized black cocks, nothing to rival Henry's
but bigger than average and obviously from the same stable. Each of them
ran a hand along his length, as if to show her how well hung they were.
She struggled as she saw the hunger in their eyes but Henry held her
down on her back. The youngest boy ran his hand up her thigh. Her long
slender legs quickly scissored out in one last desperate effort to
escape their co-ordinated assault. He grabbed her discarded panties and
put them to his face.
"Mmmm, still warm, and there's a sweet smell of sex about them. They're
a bit sticky as well, you bad girl. She's so hot for it, she's been
creaming her panties before we even get started," he laughed. "You know,
there's only one thing better than a bride..... and that's a slutty
little bride who's gagging for it."
"Nooooo," she screamed again as he slid his hands up the inside of her
thighs. "Get off me you black bastard," and she aimed a kick into his
chest.
"Oh sweetie, you got some spunk, I'll give you that," and he grabbed
both her ankles and began to pull them apart.
"Don't you dare... don't you even... mmmph."
Leroy stuffed the flimsy panties into her mouth. "There, that's better,"
he smiled.
She looked up in horror as he went back to work on her legs again.
Holding her ankles high above her prostate figure, he was able to simply
push her legs apart and then backwards until her knees were pinned to
the bed either side of her face, where Henry held them firmly. She was
in the most vulnerable and exposed position, her pink swollen pussy,
open, lubricated and waiting.
"Hey look at this. She's even shaved her pussy, the way they do in porno
films. You dirty little whore. Shaved your pussy for me did you? Man I
can't wait to try this," he smiled. He knelt on the bed and placed his
stiffening cock at the smooth and hairless entrance to her oozing sex.
"You're really hungry for cock, aren't you girl? Bet you can't wait to
have that pussy filled again, can you?" He ran his fingers over the
outer lips and occasionally tested the slimy and cum soaked channel. She
mumbled into the gag and shook her head. Leroy leaned forward and
positioned his black cock at the mouth of her vagina, then roughly
grabbed her tits.
"Here it comes, darling." She could feel it entering her and she gasped
into the gag as she felt him opening her up. She wriggled and squirmed
as he sank further and further into her but she was so stretched and so
wet that it easily slid in to the hilt and he immediately began to hump
her.
"Ooooh yeah, that's it babe," he muttered with a satisfied smile.
She let out another muffled squeal as his rigid member slid in and out
of her with long powerful thrusts and the bed smacked rhythmically
against the wall.
Debbie mumbled into the gag. Looking up in fright at Henry's smiling
face, her body squirmed provocatively in response to the young boy's
cock. "How's that feel babe? Your second black cock and it's still only
the first day of your honeymoon. I wonder how many more you'll have had
by the end... what do you think?" he laughed.
She wasn't listening to him. She was desperately trying not to respond
but she'd been at the point of orgasm with Henry and couldn't hold back
much longer. She moaned into the gag as the electric sensations from her
body began to overwhelm her. Writhing and jerking uncontrollably, she
suddenly came. Her eyes closed tightly as her muscles clamped down hard
on Leroy's young cock, her pussy flooding and convulsing into spasm.
Meanwhile, the young lad on top of her was concentrating hard as he
thrust deep inside her. "Oh yeah, you're loving this aren't you babe?"
he gasped breathlessly. He only managed to last a few more strokes
before erupting inside her. "Oh fuck... oh yeah," he gasped. "Oh babe,
we're gonna have you so pregnant by the time you go home," he laughed.
"Now, what's that pussy of a husband gonna say about that, eh?"
Danny was next up, and quickly on the bed to take his place.
"She's all yours boy," Leroy urged.
"Man, I don't want no sloppy seconds. Now this looks much more
interesting," he laughed, eying up her little pink rosebud and testing
the entrance lightly with his finger.
"Mmmmph," Debbie bumbled and squirmed beneath Leroy's searching fingers.
"Does she take it up the ass?" he asked his big brother.
"She loves it, don't you babe? Couldn't get enough of it up there last
night could you, eh? Come on man, she's gagging for it, what you waiting
for?"
Danny licked his lips and placed his manhood at the tight and puckered
opening. Debbie let out an embarrassed little squeal. She felt so
ashamed. He was going to fuck her in the ass and she would have to watch
him doing it. She couldn't even hide her face. How humiliating and
degrading. She squirmed about, rocking from side to side but it was all
in vain. He forced his black cock inside her dainty pink rosebud. "Ooooh
fuck! Oh yeah! Oh yeah! That's a tight little ass you got there girl.
Come on, open up for me," he insisted. "Seems you need a little more
encouragement," and he gave her ass cheeks a succession of stinging
slaps. Her buttocks jerked in response and her anus clamped tightly
around the tip of his weapon. "That's it," he encouraged as she started
to relax after the onslaught. It was enough for him to force an inch or
two of his manhood inside her anal ring. "Oh yeah, how you liking it up
there babe? Filling you nicely ain't it? You're just a dirty little slut
aren't you? Must be if you're letting me fuck that asshole. That's
right, it's just dirty little whores that take it in the ass."
"That's it. Stretch her out, boy," Henry urged.
Debbie looked away in complete shame as she felt herself involuntarily
gripping his thick cock. She couldn't stop it and she knew the tighter
she was the more he'd enjoy it.
SLAP... SLAP... SLAP... SLAP... SLAP... SLAP. "Come on sweetie, still
some more to go," Danny insisted.
"Mmmmph," she mumbled with her eyes tightly closed. Danny was still
firmly plugged inside her and after a few more stinging slaps, he was
able to slide the remainder of his manhood in very easily. It was as if
she'd just inhaled his cock and he was deep inside her to the hilt. She
really did feel no better than a whore now, taking his cock up her ass
like the filthy little slut he kept telling her she was. She felt so
disgusting, so depraved... yet so loving it!
Henry held her tightly as her whole body rocked gently back and forth
with his brother's thrusts, his balls slapping noisily against her warm
rosy pink buttocks. "That's it babe, just lie back and enjoy it. You've
got two whole weeks of honeymoon fucking ahead of you. I'll bet you
can't wait to get back and tell the girls in the office all about it,
eh?" he laughed.
"Yeah, she's just like all the rest, struggling like a little virgin but
loving it like a slut, and afterwards she'll be all over town bragging
about all the cock she's had, won't you?" He sawed in and out of her ass
whilst playing with her clit, which she obviously enjoyed from the look
on her face. There was no mistake, it was hard and swollen. In spite of
all her protests she was turned on and he knew it. He continued to play
with her, toying with her until he sensed she was ready.
"Uuuugh.... mmmmmph... mmmmmm," she groaned.
"Oooh yeaah, you're loving this aren't you babe, getting fucked up the
ass? Dirty fucking slut bride aren't you? Yeah, let's hear you loving it
shall we?" and he yanked the sodden panties from her mouth whilst he
continued to pound her ass.
"Ahhh.... ahhh.... ahhh.... ahhh.... ahhh.... ahhh.... ahhh.....
ahhh..... ahhh.... aaaaaahhh," she groaned as her pelvis bucked hard
against him, and her second orgasm ripped through her like a tidal wave.
"Oh yeah, you needed that didn't you babe?" he grinned as the pressure
in his swollen cock reached the point of no return. "And now, I'm gonna
shoot up your sweet ass...... ooooh yeah," he yelled, jerking inside her
and filling her with his hot black seed.
Chapter 19
Debbie meets the family
Two days later, Debbie was a changed girl. The shy, slightly haughty
young English bride had been replaced by a wanton young nymph with a
craving for sex and a willingness to try almost anything.
She stepped out of the shower and dried herself. The freshly laundered
nylon baby doll nightie floated down over her breasts and she tugged the
sheer panties up to her waist. She freshened up with her favourite
perfume and gently played with her nipples until they were poking out
the front of the nightie like two cherries. Henry had told her she would
be meeting two of his young cousins and she was determined to look her
best. She giggled as she remembered him telling her they were only
fifteen and to go easy with them. Mmmm, the thought of doing it with a
couple of young innocent boys was making her very hot. With a bit of
luck it would be their first time. There was a knock at the door and she
opened it a little nervously, not really sure what to expect, but hoping
they would at least be good looking.
"Oh! Um... I er..." She was shocked to find two young girls standing
outside, wearing skimpy T-shirts and the shortest of skirts.
They giggled at her look of complete surprise. "We're Henry's cousins.
I'm Susie, this is Diana," they explained and walked in past her without
any invitation.
They seemed so young, especially as one had her hair in bunches and the
other had a ponytail
"Right, I suppose I thought that.... well I mean...."
"You thought we were going to be boys didn't you?" Susie giggled
mischievously.
"No... no... I just...."
"Boys with big dicks?" Diana teased.
"Of course not. Look I told you, I..."
"Yeah, that's why you're wearing all this isn't it?" she said, lifting
the hem of Debbie's nightie. "All ready for bed you naughty girl. Mmm,
so pretty.... the guys just love all that sexy stuff don't they? Bet
you've got loads of pretty underwear with you. I'm dying to have a look
through your panty drawer," she giggled
"Henry says you haven't stopped shagging since you arrived," Susie
smirked. "I suppose you were just hoping for a couple of nice young boys
with stiff little pricks to come and fuck that white pussy and play with
those titties? Hmmm?"
"Leroy says you prefer making out with boys in dresses," Diana teased.
"I DO NOT!" Debbie protested.
"Maybe she just can't make her mind up.... or maybe she wants the best
of both worlds," Susie laughed.
"Maybe we've got everything you need," Diana put her hand to her crotch
and pouted.
Debbie saw they were staring at her and nervously put her hands to her
chest. They were fascinated by the sheer size of her breasts which were
poking through the front of her short nightdress.
The girls looked at each other and giggled, then unashamedly began to
strip off their T-shirts and unzip their mini skirts.
"Um... excuse me... er what do you think....."
They stood before her wearing nothing but their cute lace panties and a
smile.
"So you thought you were going to be fucking some boys did you?" Susie
giggled once again. "Well, we don't need no boys, do we Diana?" and then
Debbie saw they were each holding something she recognised from her
wedding night. They each had strap-on dildos, and were fixing them in
place around their waists.
"Oh my God. Oh look girls, I don't think...."
Susie stood right up close to her. The dildo bobbed gently in front.
Diana sat down and patted the bed, "come on sweetie, no need to be
afraid," she smiled, sporting an even larger dildo than her sister.
Susie led her to the bed. Debbie was feeling a little unsure of herself
but the girl put an arm around her as if to comfort her, and her other
hand cupped one of her large breasts. "Mmmm, you wait till you feel
Diana sucking and nibbling these. She loves big tits don't you honey?"
Debbie tried to pull away but they held her tight and squeezed gently on
her breasts. "Come on sweetie, don't be shy now," and Diana brought her
hand sharply down across Debbie's barely protected bottom in a stinging
slap.
"Ow!" Debbie protested. Diana's hand rained down onto Debbie's fleshy
cheeks, which wobbled seductively and began to turn an even deeper shade
of pink than the translucent chiffon panties she was wearing. SLAP...
SLAP... SLAP... SLAP... SLAP... SLAP. "Owwww!"
"Get her tits out," Diana yelled excitedly," and Debbie quickly found
herself on the bed with both girls giggling and tearing at her baby doll
top and grabbing her large white breasts. She tried to fend them off but
they were more than used to a little street fighting and were easily
able to overpower her.
"Let's get you out of those panties Debbie."
"Nooooooo," she squealed but by this time her resistance had become
nothing more than a token gesture.
"Mmmm, I've never had a bride before, especially a white one," Diana
teased. As her sister eased the bride's panties down, Diana was stroking
her dildo, letting Debbie see what she had coming. "Ten inches of
fucking heaven," she laughed.
"Oh God, no."
"Best get used to it girl, you'll have Henry's Daddy to contend with
tomorrow night. Yeah, if you think Henry's a big boy, well you just wait
till you see Big Daddy," she giggled. "Girl, he's hung like a horse,"
she declared.
"Like a horse," Susie agreed. "And Big Daddy fucks like a stallion too.
All the girls agree he's the best on the island."
"Noooooo....." Debbie screamed.
"Oh and a word of advice, girl. You make sure you're on top, riding
him... at least to start with. That way you'll get used to it in your
own time, if you know what I mean," Susie giggled. "Once you're all nice
and relaxed down there, that's the time to let him go on top and take
that monster nice and deep. Am I making your eyes water, honey," she
laughed out loud.
"Mmmm, I can't wait to see him breeding this one," Diana giggled, "he'll
go crazy when he finds out she's on her honeymoon."
"Noooooo....." Debbie cried again
"Yeah, a white bride. Should be a packed house, eh Susie?"
"What...?" Debbie looked up in shock.
The young girls laughed at her look of absolute horror. "Oh yeah baby,
we'll all be here, wouldn't miss it for the world. Big Daddy fucking the
white bride... should be quite an audience for that little show," she
laughed.
"Noooooo. Oooooh God," Debbie cried as they played with her breasts. She
tried to relax. There was no point trying to fight them. She knew she
had another ten days of her honeymoon left, ten days of sex, and ten
days without any thought to contraception. She would be well and truly
pregnant by the time she got back on that plane, no doubt about that at
all. How would she explain that to her parents? She lay back and opened
her legs as Susie climbed on top and eased the black dildo into her
sopping wet pussy. "Mmmmmm...." she murmured, closing her eyes and
wondering just how big the man they called Big Daddy really was. At the
same time, Diana was straddling Debbie's face and lowering her bottom.
"Oh God no... please...."
Diana stretched her pussy lips apart. "Come on girl, get that tongue
out.... come on now."
"No... not that... no.... mmmmph," and Diana's pussy sank onto her lips.
"Mmmmm," Debbie gasped, easing her tongue into the slippery sex.
"Mmmmm."
It was the bride's first taste of pussy and she lapped at it hungrily.
Chapter 20
Back in the UK
Peter woke up slowly and stared out through the heavily frilled net
drapes around the four poster bed, to the pastel coloured decoration of
the room beyond. The lace curtains were heavily flounced, the walls were
full of posters of boy bands, and the bed he was in, had white satin
sheets and lace trimmed satin pillowcases. In the corner, a girl's
frothy pink tutu with a satin bodice was draped across a chair, and the
dressing table next to it was crammed with jars of creams and fancy
bottles of perfume. It was most definitely a young girl's room, a room
that no self respecting male would want to be seen dead in, let alone
sleeping in.
Peter had spent a number of days at the house, or rather the mansion
that his boss owned. Days that he could barely remember. It seemed an
age since this had all started; when he'd woken up that fateful morning
at Sylvia's house, caught wearing one of her nighties. What a disaster
that was, and since then so much had happened. He felt as if it had all
been a very bad dream.
He shook his head. He felt muzzy. Since arriving at the Shepherd's
house, he hadn't been well and they'd had their private family Doctor
out to him on a couple of occasions. It didn't seem too serious, mostly
shock and nervous exhaustion and at last he was starting to feel a bit
better, though he still felt drugged and very lethargic. That wasn't
surprising, as he was indeed still being drugged. His boss's wife,
Samantha, had seen to it that his drinks were laced with the same stuff
that Sylvia had given him on his wedding night. The side effects made
him feel tired and spaced out but she knew it would help him to grow
accustomed to his new surroundings without too much resistance.
"So, how's our little girl today?" Peter looked up at the pregnant young
woman standing at the foot of the bed. He knew it was his boss's wife
from the pictures in Shepherd's office, he could remember that much. She
was young, barely in her thirties, and looked even more attractive than
her photo.
"OK, I suppose," he answered groggily, thinking he wasn't hearing so
well either. "What am I doing here?"
"Don't you remember? You haven't been very well have you? We've been
looking after you until you're ready for work and er... everything."
"Work? Oh my God", he panicked. "Christ, I need to get up," and he made
an attempt to slip his legs out of bed.
"Now don't be silly. You're not well enough yet. Besides, the Doctor has
signed you off for a while, and they're not expecting you back yet."
"Yes but.... there's stuff I need to get on with... budgets and..."
"It's all been taken care of. There's nothing for you to do at work
right now and they'll tell you all about the new arrangements when you
return."
"New arrangements?" he queried. Peter sat up, still feeling very
strange. He scratched his head and found... curlers in his hair! Then,
looking down he saw that he was wearing something very filmy and
delicate that also felt very silky against his skin. He looked under the
bedclothes. Oh no! Not again! It was a short, girlish, puff sleeved,
baby doll nightdress that barely covered the matching silk chiffon
panties with their contrasting lace trim around the legs. "Jesus," he
exclaimed, touching the ribbon bow tied at the neck. "Pink..." he
muttered in disgust, as if a boy wearing a girl's baby doll was alright,
as long as it wasn't pink! "But I'm wearing a.... a....."
"It's just a girl's nightie," she said, thinking how sweet it looked on
him. Admiring his slim figure and the long hair framing his pretty face,
she wondered just how this delicate creature ever imagined he could
compete in a man's world.
"It's one of my daughter's actually though she won't wear it now. She's
getting to be a bit of a tomboy. Says it's too girly and frilly for
her."
"Your daughter," he looked shocked, slithering back under the bedclothes
and enjoying the slippery sensation of silk on satin.
"Yes. Both the girls are away at boarding school so they've had to leave
most of their girly stuff behind. You're about the same size as Sally
Anne and we didn't really have anything else when you arrived. This is
her room by the way, pretty isn't it? You'll be using it for a while."
"Oh hell! I'm sorry Mrs Shepherd but I think there's been some kind of
terrible mistake here. Why have you put me into your daughter's nightie?
This is... well... I mean... it's... it's girl's stuff."
Samantha laughed at his expression of horror. "Listen, we all know about
you and your dressing up."
"What?"
"Well I'm not really surprised. Just look at you... high cheekbones,
long lashes, full pouting lips, slim waist, and the least body hair I've
ever seen on a boy. I bet you just love pulling on a dress."
"No..... NO!"
"Ah, you're blushing.....you're not a little sissy boy, are you Peter?"
and she burst out laughing. "Anyway, they were going to fire you at work
until my husband stepped in."
"Oh God! And what about the Doctor... he didn't see me, did he? Not like
this? Oh shit, he did, didn't he! Oh God," he cried, with genuine tears
in his eyes. "I want to go home. Why can't I go home?"
"Well, it's very simple. My husband has been very understanding....
considering what you've been up to with your staff... and then caught
dressing as a girl. So in return, you're to help me out with some duties
here at our house and it's best that you just accept things as they are
for the moment... unless you want to start looking for another job?"
Apart from a few sniffles, there was silence.
"No, I thought not. You can thank James personally, when he gets back
from his business trip, alright?"
He was starting to sob as she continued. "Now, stop that silly baby
stuff. I've got another little surprise for you." She called out and a
young girl in her late teens appeared in the doorway. It was Tessa, the
cocky little black girl he'd met at Lucy's house a few weeks ago.
"Oh no."
"Well if it isn't my little cutie-pie bridesmaid," she laughed.
"Wh... what are YOU doing here," he cried in an anxious voice.
Mrs Shepherd replied. "Tessa is our Nanny. She helps me with the girls,
but when they're away at school she does a lot of other things instead.
Now, I've asked her to take care of you, make sure you're bathed and
properly dressed each day, that sort of thing. I just know you're both
going to get on like a house on fire," she smiled.
"Like a house on fire," Tessa agreed, licking her lips.
"Well I'll leave you two to get re-acquainted. Then perhaps you can get
him washed and freshen him up with some nice smelly stuff, Tessa. He's
still quite weak, so pop him back into bed afterwards, OK?" Peter was
all alone with the young girl now.
"Hell, where are my clothes?" he demanded.
"Well, actually, they did bring all your things round yesterday so you
can change into something different if you'd prefer."
"Thank God for that. I'll do that in a moment but I still don't really
understand what's happened."
"Don't you remember? Your wedding? The wedding night..... you in that
dress.... no? Oh dear. I can see I'll have to let you see the wedding
video later, or should I say the ?wedding night' video," she said with
raised eyebrows. "Mrs Shepherd and I had a good look at it the other
day. Looks like everyone had quite a time," she said in a mocking tone.
"I'll put it on later and we'll see if it jogs your memory."
Unfortunately, it was already starting to come back to him. "Oh my God!"
he exclaimed. "Debbie? Where's Debbie?"
"Oh don't you worry about her, she's fine. She's enjoying her honeymoon
in the Caribbean. That was really nice of you, you know. Mrs Shepherd
was saying only the other day... she didn't think she'd ever come across
such a kind, generous and understanding young man."
"What...?"
"Yeah, Sylvia told us all about it, your wedding night. I mean it
couldn't have been easy, finding out you that couldn't satisfy your
bride, especially with it being your wedding night. What a shock, and a
hell of a disappointment, eh? Most men would have been devastated but
you were so unselfish and only thinking of her weren't you?"
"But... but..."
"Yes, you're a real gentleman, especially the way you found that
absolutely gorgeous hunk and got him to take care of Debbie on her
special night. I saw him on the video. Mmm, he's quite a guy isn't he?
How did you get him at such short notice? Anyway, I can't think of any
other young man who would be so unselfish. And you know what was a
really nice touch? That fact that you stayed the night to make sure he
paid attention to all the little intimacies that you'd have wanted to
give her yourself. How sweet. And it says something about Debbie that
she appreciated what you did and wanted to make sure you weren't left
out of it."
"What?"
"Yeah, you're lucky to have a wife that's so understanding about your
little... er... bedroom problem, someone who doesn't complain about you
wearing her wedding gown and bridal lingerie. Hell, she even arranged
for that nice young man to take care of you on your wedding night. It
looked like you enjoyed it, too!"
"Uh....."
"And Sylvia said you were so grateful for what that nice boy did for
Debbie that night, that you insisted he take your place on the honeymoon
as well. I was a bit surprised at that, but you'll be pleased to know
that she's having the time of her life even if she's not getting much of
a tan," she laughed. "Well, you know what guys are like... especially on
honeymoon. Mind you, I bet she can't keep her hands off him either.
Pretty difficult to resist a hunk like that," she laughed. "Anyway, I'm
sure she'll tell you all about it when she gets back."
Peter was so shocked, he mentally switched off to her incessant
ramblings. "Look, I want my clothes right now, if you don't mind."
"OK, well Sylvia brought your clothes over yesterday. I think you'll
find she's thought of most things you'll need. She's been a very busy
girl you know," and she pulled back the sliding doors of a huge
wardrobe. "What do you think/"
Peter's eyes were agog. He must have been looking at his boss's
daughter's stuff, surely.
"Aren't they gorgeous?" she said, casting her eye up and down the rail
of spectacular dresses, maybe twenty in total, spilling out of the
confines of the wardrobe. There were pinks and blues, satin and silk,
polka dots and flowery patterns in a rainbow of soft feminine colours.
"This is your new home, and these are your lovely new clothes. Special
little dresses for a special little girl. A dress for every day and a
dress for every occasion," Tessa announced in mocking sing-song fashion.
She pulled a few out to show him. They were all very similar in style,
short silky confections, lavishly decorated with frills, ribbons and
lace. The humiliating child-like style dictated they could only be for a
little girl, but the size meant they'd been designed with a rather grown
up little girl in mind!
"That girl made every single one, especially for you. It must have taken
her every spare minute she had and it's certainly cost the Shepherd's a
packet."
Peter's mouth fell wide open.
She picked one out at random. It was made of white bridal satin. Ruffled
white lace generously encrusted the bodice and sleeves. Three tiers of
beautiful lace-trimmed white tulle provided a dramatic overlay. Pale
pink rosebuds dotted the stiff satin skirt. Frilly, dainty, and lacy...
were the words that just about summed it up. She returned to the bed,
holding the rustling frock by its pink satin hanger. She sat down next
to him and arranged the dainty dress over his body. "When I was a little
girl, I loved wearing pretty little dresses like this and my Mother
always had me in oodles of rustling lace petticoats underneath. Those
little dresses were so short. I couldn't hide my petticoats no matter
how hard I tried. Oh it's so cute isn't it," she reminisced, examining
the pretty lace. And I bet I know what you're thinking," she laughed
softly.
"W-w-hat? What am I thinking," Peter guardedly asked.
"You're thinking that you'd love to try it on, aren't you?" she laughed.
"No....NO."
Fingering the lace- trimmed tulle, caressing the shiny bridal satin, and
in her best, feminine, girly-girl voice, she whispered. "Oh I think
you'd love me to pop it on you Peter. Just think, a real little girl's
dress. You'd look so pretty in it wouldn't you? Oh you're blushing again
Peter," and she burst out laughing, imagining it on him.
"Look, what is it with all these clothes? Why have you got me all this
girls' stuff for God's sake?"
Tessa tried to make some sense of it for him. "Well. What do you think
of this dress? Do you think it's a pretty dress?" she asked gently,
touching the lace and fluffing out the frills
"Well... yes, it's OK," he replied watching her.
"And do you think a girl would feel nice wearing it," she asked, taking
his hand and making him touch the buttery soft satin.
"Yes, I guess," he said, his mouth going dry and his heart beating
rapidly.
"It's so pretty, I think it would look cute on a boy as well, don't
you."
"Um... maybe," he replied, feeling faint.
"Do you think it would look nice on you," she asked, pulling it up
around his neck and spreading the skirt out.
He licked his lips. "Well... perhaps."
"OK. Now be honest. Are you saying you don't want to try it on... see
what it looks like, and how silky it feels?"
There was silence. Tessa smiled.
"And don't tell me you haven't got a stash of girly clothes at home, or
that you never tried any of your girlfriend's stuff, or went through her
panty drawer?"
Silence again. Peter looked downcast, a little shamefaced.
"See. You're desperate to try it on. And that's why Mrs Shepherd has got
you all these lovely things. She's done it for you, sweetie-pie. OK?"
He seemed to accept what she'd said even though he felt so confused. And
it was a conversation they would have again and again, but he would
always end up hearing that they were doing it all for him.
Returning to the chest of drawers, she said. "Oh yes... and Sylvia made
most of the lingerie too, though we did have to buy one or two things,"
and she pulled open one of the drawers to reveal a sumptuous collection
of feminine finery. She was spoilt for choice but selected at random, a
pair of lemon frilled panties to show him. "Aren't they cute? There's
every colour you could wish for, and every single pair is beautifully
decorated in pretty lace and feminine frills. I used to wear panties
like these. I used to call them my church panties," she giggled. "Mmmm,
all those girlish little frills," she said, picking at the delicate rows
of lace across the back."
"And in the other drawers you'll find stockings, suspender belts, slips,
petticoats, nighties, plus a load of scrummy baby wear..... just in case
we have to resort to that," she laughed. "And they're all yours,
sweetheart. Now, don't pretend you don't like them. I know you're going
all goosey. You're such a lucky little boy aren't you? There's no
guesses for what you'll be doing under the bedclothes the moment I leave
the room," she laughed.
Peter tried to clear his head. It was like a bad dream but what could he
do? He really did feel weak. He had no clothes, at least none he could
be seen outside in, and he couldn't even talk to his boss about it! He
decided he'd have to wait until he was feeling better, return to work
and sort things out with HR. At least they would be able to help. In
fact they'd be shocked at what was happening to him!
Tessa sat down on the bed again, this time with a sickening smile on her
face. "Now you've got your very own panty drawer to rummage through
haven't you, cutie-pie? Hmmm?" She slid her hand under the bedclothes
and found the front of his silky panties, the panties that belonged to
his boss's daughter! He flinched, but before he could stop her, she was
caressing him through the silky chiffon.
"Oh God, no," he protested, clamping his legs together, but he was
already growing hard and she could feel it. If he wasn't careful, this
dreadful girl was going to make him do something very embarrassing,
something he didn't want to do in front of her. He should have stopped
her... but the truth was that he didn't want to. "Hell." She was going
to make him do it in his panties. "Please.... no," he protested limply.
"Shut up. You know you love it, and if you're a good boy and don't give
me any trouble, I'll give you a really nice wank in a lovely little pair
of girly satin panties... every morning." Peter closed his eyes and
relaxed his thighs, allowing her hand to slip inside the panties and
explore, searching for his erection. He gasped as she took his penis in
her hand. He was completely gone now. "There, you see. You boys are all
the same. You just love getting a nice rub, don't you? Now then, look
how hard it is already and we've only just started." It was true, his
little penis was as stiff as a board as she closed her fingers around
him and stroked up and down the length. She smiled. He was responding as
she'd hoped, and just like she knew he would.
The pace of her fist travelling up and down his penis increased and she
whispered in his ear, "that's it, keep those eyes closed and imagine
your pretty bride all decked out in her finest, frilliest lingerie. And
that gorgeous hunk, fondling her big breasts, licking her pussy, and
filling her with that huge cock.
"Do you remember how it was on your wedding night? He was in her mouth,
inside her pussy, even up her tight little virgin ass, wasn't he? Mmmm,
did you enjoy watching her being shagged... on your wedding night? He
was a real stallion wasn't he... just what she was needing... and now
he's on honeymoon with her and I bet they're at it day and night, eh?
What a guy," she sighed, stroking him ever faster.
"Yes, you're a bit envious aren't you... thinking about him lying next
to your bride every night, screwing her senseless? It's only natural.
You've every right to feel jealous. I bet you'd give anything to change
places wouldn't you? Just imagine yourself in that romantic honeymoon
suite, peeling away her sexy honeymoon lingerie. You'd be on that bed
quick as a flash. Mmmm, you'd be so hard and ready for it wouldn't you?
Mmmm, and that monster of a cock," and Peter suddenly opened his eyes,
causing her to giggle.
"No, not yours silly... the one he's pushing between your bottom...
ready to pound that sweet little ass," she laughed. "Sounds good doesn't
it, hmmm?" He was completely under her control now, closed his eyes
again and groaned loudly, close to orgasm.
"Well?" she whispered, stroking him faster. "Would you like that?"
"Ooooh yes," he muttered.
"Yes that's right. Well, maybe you won't have to wait too long," she
smiled knowingly. "Now then, just relax and cum into Sally Anne's little
panties, that's a good boy." He lay back to enjoy the moment as she
brought him to a shuddering, sticky climax, pumping away until Sally
Anne's panties were soaked and he lay limp and lifeless.
With a satisfied look on his face, Tessa led him unsteadily down the
hall to the bathroom. She put the nightie and soiled panties into a
hamper of dirty washing and helped him into a hot bath. Telling him to
wash himself thoroughly, she left him to get on with it. Alone at last,
it was only then that he realised he'd lost the blond fuzzy hair around
his penis and balls. He put his hand down there as if to check. He was
silky smooth, like a baby's botttom. It was a bit of a shock, but then
it actually looked quite sexy, and now it was gone there wasn't anything
he could do about it anyway. He had a nice soak in the warm water.
Feeling a bit more relaxed, he had a wash, got out of the bath and was
just starting to dry himself when something very feminine hanging on the
bathroom door caught his eye.
It was a beautiful peignoir set. It looked expensive and presumably
belonged to Mrs Shepherd. His towel dropped to the floor as he took the
floaty negligee off the hook. There was absolutely no weight or
substance to the luxurious material and it felt divine. He carefully
explored the beautiful matching nightgown. The shimmering and delicate
pink chiffon adorned with expensive French lace and dainty ribbon bows
literally trickled through his fingers. It evoked images of those
vintage Hollywood glamour years, an age of innocence, femininity and
romance. He buried his face in the soft heavenly material and the sweet
smell of her delicate feminine perfume wafted around him, invading his
senses. At the same time, the filmy material slithered against his body
and tickled his small rigid penis that was already twitching in arousal
and expectation. It felt like paradise and with no sign of Tessa
returning, he couldn't resist.
Shaking with nervous anticipation, he pulled the dreamy nightgown over
his head and felt it flutter gently over his naked and slightly damp
body until the ruched, embroidered waistband settled around his tummy.
He then eased the heavenly full skirt over his protruding penis and let
it cascade down his thighs to leave the six inch frilled hem fluttering
gently around his ankles, tickling his feet. Glancing in the bathroom
mirror, he noted that even the double layered skirt did little to
conceal his modesty, his boyish masculinity unashamedly tenting the
front of the nightdress. It certainly wasn't a nightgown for the shy or
faint hearted! Licking his lips, he pulled the slippery material tight
around his thighs, emphasising his engorged penis. Mmm, what a sight, he
reflected. There was nothing like a penis straining a set of intimate
and feminine, silky lingerie. And this was no ordinary ensemble. These
little dainties were not for wearing in bed on a cold winter's night,
and they certainly wouldn't have been worn for the purpose of sleeping
in. No, this was boudoir lingerie, adored by sexy mademoiselles and
reserved for those romantic and intimate nights of passion with their
young, virile and insatiable lovers.
The matching peignoir was even more elaborate, consisting of yards of
sheer nylon chiffon layered over shimmering silk. Its purpose was not to
conceal but to entice, tempting and teasing the eyes of a male admirer.
Something like this would have been worn only briefly, undoubtedly
removed no sooner than it had been put on. And to complete the
delightful set, there was a pair of matching satin tap panties, lavishly
finished with beautifully embroidered net lace around the legs, and pink
ribbons intertwined with lace and tied into darling little bows in
front. "Oh my God," he moaned softly. They were the sweetest, most
feminine of panties for the girliest of girls. But could he be that
girl?
Holding the peignoir, he slipped his arms inside the voluminous, puffed,
elbow length sleeves with their elasticated and frilled cuffs, and
secured the bodice by tying the long pink satin ribbons at the front
into a large bow. He swished the long skirts around his legs. The
delicate peignoir revealed everything underneath so beautifully and it
felt divine. Yes, he was made for lingerie like this. Mmm, he imagined
sweeping into an elegant room in a cloud of perfumed chiffon, making the
most dramatic of entrances. The room was full of young, red-blooded
males. Ooooooh, he was practically swooning at the thought of it.
Laughter and discussion quickly turned to hushed silence. Every pair of
eyes immediately trained on his revealing lingerie... and the small yet
tantalising protrusion in front. Jaws dropped and lips were
involuntarily licked as Peter flirted and teased them. He slowly
caressed his prettily disguised masculinity. They couldn't stop
themselves. Their eyes were glued to his boyish equipment and his round
girlish bottom. With much fidgeting and nervous clearing of throats,
hands quickly began to slip into trouser pockets. Peter was in heaven,
he had them all by the balls... literally! He walked toward a group of
three particularly good looking boys with tell-tale bulges in the front
of their trousers. Suddenly they picked him up, carried him to a chaise-
longe and were followed by the others. The three young men quickly
stripped off. Naked, gorgeous, and erect. They looked at him
purposefully. He knew they would be the first to take him, and that
would just be the start of it!
Reluctantly returning to reality, he held the panties up. "Mmmm, French
knickers, my favourite," he muttered quietly to himself. "They're
gorgeous. Little darlings," he added, examining the intricate lace
detail. They would be the last vestige of protection for a young lady's
modesty, simple for her lover to ease down, or maybe pulled to one side
if he was in a hurry, and roomy enough to slip his truncheon inside,
before entering her pussy.
Peter felt he was going to explode at any moment. He looked nervously
toward the door. No, he couldn't. This really would be chancing his
luck... what if Tessa returned and caught him? No, it was too much of a
risk, she'd be back soon. He decided to take everything off, carefully
put it all back as if nothing had happened. But then.... his straining
penis persuaded him to think again. This final piece of lingerie was
playing havoc with his judgement. He simply had to wear it all. "Oh
shit," he muttered. He stretched the lightly elasticated waistband of
the wide legged panties and looked at the inviting lacy pink chiffon
waiting to envelop his boyish manhood. Lifting the hem of the nightdress
and negligee out of the way, he carefully stepped inside the oh-so-
pretty panties and slowly raised the cool slippery satin up his legs
until the lacy waistband closed around his middle. As the nightie
fluttered back down his legs, he looked at the reflection in the mirror.
The knickers were just visible underneath the nightgown and the
peignoir. He couldn't have looked or felt more girlish if he tried!
"Jesus, look at me," he murmured. "Oh God I'm so pretty, so girly. I
just need a good looking boy.... to... to..... oooooooh," and he closed
his eyes in bliss as he stroked his penis through the soft, sensual
chiffon, savouring the heady scent, and the sweet sensation of the most
feminine of lingerie that ever teased his masculinity. He was so close
to orgasm... but... at that very moment he was rudely interrupted by the
sound of Tessa's voice.
"Are you ready in there? Sweetie-pie? It's gone very quiet, what's going
on?" Holding a container of scented talcum powder she suddenly pushed
the door wide open.
"Holy shit! What are you doing in that?" she laughed, shaking her head.
"Jesus, wait till Mrs Shepherd sees this."
"No... no, please," he begged, realising she wasn't joking, but she
pushed his hand away from his groin and made a grab for the outline of
his penis, still tenting the expensive negligee.
"Get off," he demanded, but she was holding it tightly.
"Come on sweetie-pie, out you come," she smiled, leading him forcefully
by his boyish penis out onto the landing.
"Mrs Shepherd," she yelled at the top of her voice, firmly gripping his
equipment. "Have you got a moment," she added, pumping her fist up and
down his erection whilst he half heartedly struggled to break free.
"What is it? I'm busy," the voice replied.
"I think you should see this, Mrs Shepherd," she smiled, as she
continued to wank his boyish member whilst he continued to thrash about.
"Oh, alright," she tutted and seconds later, Tessa stopped her
manipulation just as Peter was confronted by the young woman. She was
annoyed at being disturbed, but absolutely furious at the sight of him
in her expensive nightwear.
"MY GOD! That's my lingerie you're wearing! The panties too! We went to
the trouble of getting you all those pretty things of your own, but you
just couldn't resist could you? Do you realise how much that set cost my
husband? It was a tenth anniversary present. It's a 1950's Vanity Fair
negligee set. It's so fragile I hardly dare wear it myself. It's kept
for um... well for special occasions," she said, suddenly feeling a warm
glow as she recalled how it gave her husband an immediate erection the
last time she wore it for him.
"If he finds out about this, it'll be the end for you. You know that,
don't you? After all that nonsense you've been up to, the only reason
you've still got a job is down to my kindness, and his charity."
Peter's face was crimson. "I'm.... um.... er... sorry.... Mrs Shepherd.
I was just trying.... I didn't realise. I mean... I um...." he stumbled.
Despite his shame at being caught in her precious lingerie and the fact
that Tessa was still holding him tightly, he was as hard as a rock.
Tessa suddenly let go of his penis, giggling at his predicament and
whispered into Mrs Shepherd's ear whilst Peter's manhood twitched and
rose up and down like an old fashioned railway signal.
"Yes... thank you for that Tessa," she replied curtly, glancing down
below his waist. "I'm well aware that he's got a disgusting little hard-
on... in MY negligee. He's completely stretched the panties at the front
and he's starting to ooze that nasty boy stuff all over them...ugh!
They'll be ruined," she said with disgust. "Right. Get him out of my
lingerie this instant. Get everything washed, dried and ironed and see
what you can do to remove those creases and the stretch marks in the
panties. And as for you," she hissed at Peter, "you step out of line...
or into my lingerie... one more time, and I'll be telling my husband all
about this little incident," she threatened, angrily. "Then it'll be
curtains.... OK?"
"Yes, Mrs Shepherd," he said apologetically, just as he was consumed by
an involuntary release from the erotic stimulation of the pretty
lingerie and Tessa's helping hand-job. "Oh shit," he gasped as his whole
body convulsed and his penis went into spasm. Samantha Shepherd's jaw
dropped. Peter tried in vain to control himself but it was far too late,
and a dark wet stain quickly spread across the front of the panties,
through onto the nightdress, and finally across the front of the
negligee.
The two females simply stared for a moment in disbelief as his quivering
body slowly came to a halt and the full extent of the damage was
apparent. "Oh dear," Tessa exploded into laughter.
"RIGHT! Get him out of my sight," Mrs Shepherd shouted, and she was
still ranting as Tessa ushered him back into the bedroom and closed the
door.
Chapter 21
Bridesmaid Revisited
The next few days passed relatively quietly and uneventfully. Mr
Shepherd was still away on business and Peter gradually recovered his
strength, spending all of his time in the sweetest of dresses. Mrs
Shepherd had arranged for a beautician to visit the house to pierce his
ears, advise Tessa about his make-up and to style his hair. He'd needed
a haircut for some time, and his hair was now long enough to give them
several options for a new girlish style. Everything was agreed with Mrs
Shepherd before the girl gave him a cute fringe that just covered his
eyebrows and curls that flicked up at the back.
Every morning, Tessa went through the routine of selecting his girly
clothes for the day and the only time he actually resembled a boy was
when she bathed him first thing in the morning. Mrs Shepherd was
delighted with the progress of his transition. She took great pleasure
in watching each day as Peter gradually became a little more at ease
with wearing a dress in front of them, and more accustomed to being
treated like a girl. His resistance was melting away fast and although
there was still a long way to go... so far, so good!
A few days later, Peter woke to the normal "Wakey-wakey," as Tessa
pulled the curtains back and let the sun stream in to the room. He
screwed his eyes up and yawned. He was completely used to the young girl
getting him up, making sure he bathed and shaved, drying him off, doing
his hair, make-up and perfume, then getting him dressed.
"It's a lovely day," she beamed, "and we've got a special surprise for
you this morning so I want you to look your absolute best. She looked
thoughtful for a moment as she always did when trying to make up her
mind about what he should wear. "Yes, I think we'll have you in...
yellow," she announced thoughtfully, taking a pale yellow satin dress
from the wardrobe. It was one that he hadn't had the pleasure of wearing
before and his heart skipped a beat as he took in the white lace across
the bodice and the very full skirt, a fairly typical party dress for a
little girl. She also picked out a ridiculously frothy white petticoat
to go underneath. "So simple, but so, so cute," she teased, laying it
all on the bed for him.
She pulled the bedclothes back and led him away for his bath. Afterwards
she teased out the curls in his hair and gave him a cute ponytail, tied
with a little yellow ribbon. For once though, she didn't do his make-up
and he even asked her why not, which amused her no end. Back in the
bedroom, she was ready to get him dressed. "Now then, here are some
hold-up stockings and oh yes, the pretty matching panties," she said,
reaching into a drawer and taking out a pair of gleaming yellow satin
panties covered with little girl frills across the back and an
embroidered rose on the front. "It's a short skirt so you'll definitely
be needing these, and I know how you simply adore your frilly panties
these days," she giggled.
As usual, he stood there demurely whilst she dressed him from top to
toe. Under her watchful eye and expert direction, he was becoming quite
accustomed to his new life and beginning to discover the girl within. If
truth be told, he enjoyed her consuming attention and rarely complained.
She reminded him of his youth and the days when his mother and his aunt
would ooh and aah as they dressed his little sister and his cousin in
their girly dresses and frilly knickers. In those early days, he was
especially interested in their knickers, they were so intriguingly
different from his own underpants. Of course, he would pretend to be
engrossed in something else but he was actually watching it all
intently, feeling jealous of their pampering, and resentful that he was
always left out of their girlie dressing up sessions.
Maybe it was the yearning of that little boy all those years ago, to be
the absolute centre of attention, to experience women fussing over him,
transforming him into their pretty little darling, that now made him so
strangely compliant.
Or, perhaps it was because throughout his youth, he'd been denied and
deprived the feminine delights of those sensual silks and satins, lacy
frills, and soft girlish feelings that no normal or self respecting boy
would ever dare to admit to.
Or maybe it was just that he happened to be one of those boys that
dreamed of a pretty girl dressing him up in a gorgeous dress and dainty
underwear.
Whatever the reason, right now he was in heaven. He was used to her
dressing him, and he was still in a trance and trying to make sense of
it all when the doorbell rang.
"Oh that sounds like they've arrived," she sounded surprised. "Now then,
we've got some nice girls here today and I want you to show them what a
delightful and dainty little girl you can be."
"Girls? Here?" he panicked.
She teased out the final layer of the fluffy petticoat, then arranged
the skirt over it with the lacy white hem just visible beneath. She
stood back to admire her work. "Yes, very nice. Yes, I think they'll be
well impressed, don't you?" Peter still hadn't really taken in what she
was saying
He suddenly recognised the voices downstairs. He was mortified. The
girls were from his office... Cherie, Jan, Sylvia and Fiona, all making
their way up the stairs.
The sight of their boss brought them to a halt. He'd been transformed
into a darling little girl with a cute ponytail, an outrageously
feminine yellow satin party dress, and frothy white petticoats peeping
out below the hem. It brought a momentary lull to their excited chit-
chat, then prompted wholesale giggling.
Jan, his ex-girlfriend, was the first to speak. "Oh, that's such a
pretty little dress you're wearing Peter, and I love your perfume, mmm.
Girls, isn't that a darling dress? Where did you get your cute dress
from, Peter?" she asked in a juvenile voice, with no response.
"He's gone all shy on us," she laughed. "So, how often do you dress him
like this, Tess?"
"Oh, we keep him dressed in something pretty all the time. He loves all
his new outfits, don't you cutie-pie?" Tessa smiled, raising the hem to
show off the lavish lace and girly frills underneath. Peter felt
crushed.
"Hey, he's all dressed up for a little girl's tea party..."
"Or a school dance..."
"We could even enter him in a pageant."
His eyes were downcast. He looked all pink and embarrassed, and pushed
the hem of his dress back down, then began fiddling nervously with it.
"Ahhh, he's blushing, how cute. Are you wondering what we're doing here,
sweetheart?" Jan asked her former boyfriend, lifting his chin. He was
horrified as well as puzzled, but when he saw how they were dressed, the
penny dropped.
"I think he's realised," Sylvia laughed knowingly.
"You were hoping we'd forgotten all about it weren't you?" Fiona added.
"Have you guessed, sweetheart?" Jan teased, stroking a few stray hairs
from his eyes.
"Lucy's getting married today. Remember? She's going to be wearing a
beautiful white gown and all the little girl attendants are going to be
wearing their prettiest dresses."
"He still looks a little confused, doesn't he," Sylvia smiled. "It's
bridesmaid's day," she explained. "We're going to take you to her place
and get you into your very own bridesmaid's dress with all the dainty
undies. Then it's off to the church where everyone is simply dying to
see you."
"Yes, it's going to be your big day as well as hers.