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Bossed Into Panties
by Karen Petties
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 fiancée 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. You'll be able to show everyone what a beautiful little bridesmaid you make in that gorgeous dress. Do you remember it honey? Yes, of course you do. That pretty pink dress and all those frilly petticoats underneath. You looked so cute in it the last time, didn't you? Oh I can't wait to get him into it."
"He'll be such a little sweetie, frou-frouing down the aisle in that flouncy dress" Fiona giggled.
"Oooh, you're going to have all those good looking boys after you today aren't you?" Cherie teased him some more.
"Yes, and little Fiona is waiting for you back at the house. She's talked about nothing else all morning. She's been going on an on about that girly dress and those oh-so-frilly panties" Sylvia laughed.
"Such a shame Debbie won't be there to see him."
"I know… but we'll take lots of photos for her won't we. I can't wait to show everyone at the office."
"I'M NOT GOING" he suddenly shouted in a defiant tone, and they all looked shocked.
Hearing his little outburst, Samantha Shepherd appeared at the door. "NOT GOING? Oh really? I don't think you've much choice in the matter, dear. My husband will be very annoyed if he finds you've let the girls down. I don't think you want to upset him now, do you? We've had this discussion before haven't we? It wouldn't be good for your prospects at work to upset the Chief Executive now would it? Surely, I haven't got to spell it out again… and surely not in front of the girls."
"And we've got a copy of your wedding video at work. Remember? There's some great action from the wedding night on it. I'm sure your family would be thrilled to see it" Sylvia threatened.
He hesitated but in reality he knew there was little choice. He'd been lulled into a false sense of security over the last few days but deep down he'd been dreading the thought of this day for weeks. The idea of having to wear the bridesmaid's dress again, and parade in front of Tracey's family and friends was too awful to contemplate. He nearly stood up to them…. but he didn't. He knew he had to do whatever it took to keep his job, and if he could just get through this last torture today, he'd have done everything asked of him by the girls in his office and he'd be free of their threats once and for all.
Mrs Shepherd saw his resistance was melting and piled on the torment. "That's better. The girls are going to make you into the prettiest bridesmaid and you're going to do Tracy proud when she walks down that aisle. Then afterwards you'll have a lovely time at the reception, won't he girls? All those boys…." and she giggled, "and they'll all want a dance." Peter looked up in shock. "Oh yes. You WILL dance with the boys… and you WILL let them kiss you… no, no you WILL kiss them" she repeated as he started to protest. "And DON'T you dare say you don't want to, because we all know you'll be loving every minute. Oh yes, I think you're going to be a big hit with the boys tonight."
Tessa and Mrs Shepherd watched from the front door as Peter was led by the group of laughing girls to the waiting car. His skirt bobbed and swayed around his thighs in the breeze as he fought to keep his skirts under control. They bundled him reluctantly into the car and stuffed his skirts inside. Tessa would have loved to have been there to see him mincing along in that bridesmaid's dress with its flowing skirt and petticoats spilling out underneath. Still, there'd be lots of photos.
At Lucy's house, it was complete mayhem. Her parents were running around panicking about the slightest thing and the house was full of giggling girls, some getting changed, and others wandering around with glasses in their hands, half drunk.
Peter was quickly taken upstairs to one of the spare bedrooms where he came face to face again with Lucy and her nieces, Christine and Carol. The two sisters were already dressed and looked disarmingly pretty and innocent in their long pink satin bridesmaid's dresses. They were far too angelic to be involved in this ridiculous charade he thought… at least he hoped.
"You took your time getting him here. Where have you been?" Lucy looked harassed. She still wasn't dressed and was wearing a satin robe that kept parting at the front to reveal little flashes of stocking tops and suspenders, sending Peter's heart racing.
"The traffic was just awful" Jan replied.
"Well, we've got to leave in an hour. At this rate we won't have time to work on his make-up or anything" Carol added.
"Oh dear!" he grunted.
"Well, it's up to you. You either have your make-up and hair done properly and pass as a girl, or you can just let everyone see that you're a sissy-boy in a dress. Either way, you're going to be paraded in petticoats. What's it to be?"
"Not bothered" he muttered.
"Pardon?"
"OK, OK. I'll have the make-up" he added sheepishly. "You'd better do a good job though. If anyone recognises me today…"
Christine smiled at his meek submission. "We'll get you dressed first, and when Sylvia's free she'll pop in to do your make-up depending on what time we've got left. Remember, the quicker we get you changed, the more time she'll have, and the more convincing you'll be. Right, off with your clothes" she said, as Lucy left the room to get into her wedding gown.
He was alone now with the two girls. What Christine had said, unfortunately made sense. He stripped off as quickly as he could, repeatedly telling himself he just had to do this one last thing to get them all off his back. As he finished undressing and stepped out of his boxers, Sylvia walked in without knocking.
She looked him over with a grin. He was stark naked, all pink and nervous. Her one time ferocious boss was trying desperately to hide his somewhat insignificant private parts with his hands. "I'll do your make-up as soon as you're dressed sweetie, but you'll need to hurry, the car will be here shortly" she said, and left as quickly as she'd entered.
His pink satin bridesmaids dress was hanging up on the door, and it was even more girlish and frilly than he remembered. He shivered as he took it all in. Short puffy sleeves, lacy bodice with a sweetheart neckline and the very full skirt with its pink chiffon overlay decorated with rows of pink edged, white lacy frills. Any normal male would have turned round and run a mile, but Peter was experiencing those all too familiar, tingling sensations in his loins. Naturally, he was afraid of what was to come but he DID so want to enjoy the feeling of that dress once again, that pretty, pretty dress with its glistening full skirt slithering around his legs and all the frilly petticoats to go underneath. He knew, that part of him ached to wear that dress again. It was so girlish, so gorgeously feminine… and he knew that Christine and Carol would add to the experience by dressing him so sweetly. A shiver ran up his spine at the thought of it.
He turned his attention to the bed, where the lingerie was laid out all ready for him. Once again, there were those dreaded frilly pink knickers, the knickers that screamed LITTLE GIRL… the knickers he was ashamed to admit… he'd had naughty wet dreams over. Then, the voluminous frothy petticoats. They were even more frilly than the ones waiting for him in the wardrobe of his girly bedroom. He remembered that they called the first one a base petticoat, and then there was the really fancy one that went on top, completely smothered in lace, frills and little satin bows. Finally, there were some shiny nylon stockings… but wait a minute… they'd made him wear pantyhose the last time.
Carol noticed his puzzled look. "Yes, we decided to change the pantyhose for some grown-up stockings. They feel so sexy when they're on" she cooed. "And look at this" she giggled, holding a pink satin suspender belt, beautifully embroidered with French lace, and with four ruched, lacy straps with shiny pink ribbons to hide the clips. "You'll love the way it tugs at the stockings and keeps them nice and tight. It's such a sexy feeling and wait till you see the boys reaction. They'll go ga-ga when they clock those suspenders."
"W…what?" he stammered.
"Oh I'll be telling them exactly what you're wearing underneath" Christine sniggered. "They'll be queuing up for a dance and a grope, you just wait" she laughed. "There's nothing to beat the feeling of a guy with his hand up your skirt" she added.
"Right. On with the panties then. Aren't they divine?" and suddenly he saw what was on the front of them. He couldn't help staring.
The letters P..E..T..E..R had been lovingly embroidered above a lace heart, and inside the heart in smaller letters, the words 'boys, boys, boys' had been added.
She sensed what he was looking at and giggled. "You'd better not let the guys get this far up your skirt or they'll all know your little secret, won't they?" she laughed. "Not many girls are lucky enough to have their names embroidered on their knickers are they? Mmm, and those darling little frills. They'll really make you feel like a sweet little princess, won't they?" She held them open for him. He hesitated and looked at her with pleading eyes. She licked her lips, urging him to hurry up. Reluctantly, he stepped inside, a shiver running up his spine.
She slowly pulled them up over his thighs. His penis grew stiffer as he held his breath, the ruffles of lace tickling his smooth legs and a strange dizzy sensation coursed through his body. "Mmmm, your very own pair of bridesmaid's panties. Don't you feel a little darling in them?" Stretching the elastic around his waist, she smoothed the lavish satin over his dainty girlish bottom. He clenched his buttocks in response and she couldn't resist giving his pantied bottom a little smack.
Sitting him down at the dressing table, Carol carefully bunched the gossamer thin stockings before pulling them over his feet and expertly rolling them up his smooth thighs. She then fed the garter straps inside his knickers and attached the be-ribboned clips to the lacy tops of the nylons.
The bra came as something of a shock to him. Up to now, he hadn't had to wear one. It too was pink and lace trimmed, and they had some squishy inserts to stuff inside, giving him a small but noticeable bust.
Suddenly there was a knock at the door. Peter froze. It was Lucy. "Are you nearly ready girls?"
"Heck no, we've only just started." Christine shouted. "We're just about to get him into his petticoats, and we're nowhere near getting his make-up on."
"Well you'll have to hurry up. We don't have much time."
"Right, let's get a move on" she told him. Christine quickly hoisted the base petticoat up round his waist whilst Carol fed the profusely frilled one, the one that would most definitely be seen, over the top of his head and tugged it down until it was stretched out across the first. A few minor adjustments were required to ensure the multitude of ruffled layers would act as one beneath the dress, and finally he was petticoated.
"There, doesn't he look sweet?" Carol purred. The silk taffeta layers felt soft and slithery against his stockinged legs and the loud rustling echoed in his ears, a constant reminder of the feminine confection he was encased in, and a taste of what was still to come.
"OH I've been waiting for this moment" Carol sighed and held the dress up. "I've dreamed of seeing you as a little bridesmaid again. Now, arms up." Beyond protest now, Peter raised his arms obediently, just like his little sister would do when she was being dressed by his mother. To Carol's delight, his breathing quickened and his face reddened while she fed each arm into the puffed sleeves. She pulled the dress down over his chest, settled it round his wait then zipped him up, finally encasing his body in sensual satin. She then only had to tie the sash into a bow at the back and pop his stockinged feet into the satin ballet pumps that tied with broad white ribbons around his ankles. "One last thing… an ankle bracelet. It goes on the left ankle… to show you're available" Carol laughed.
"There! How gorgeous is that" she squealed with delight. "Wait till Sophie sees you. She hasn't stopped going on about you since the last time she saw you in that dress." He was totally frilled up, trussed up like a little girl… in a very fancy little dress, and the thought of having to face Lucy's five year old niece once again, filled him with dread.
Christine opened the door and amidst all the commotion, yelled out to Sylvia that they were ready. Sylvia gave him a big smile as she entered the room. "Oooh, what a pretty little girl. And you're going to look even prettier once I've finished, aren't you? Oh just look at those cute baby blue eyes. We'll have to use plenty of eye shadow to really show them off won't we?" She sat him down and carefully went to work using pencils, mascara and a dark eye shadow to heighten his pretty eyes. Then there was pink lipstick and gloss to create full and sexy lips, blusher, and a coat of pink nail varnish. Finally, she used some curling tongs to give his wavy blond hair some more body before teasing out the soft feminine curls she'd just created. They put some large gold hoop ear rings in his recently pierced ears and gave him a girl's watch and a tiny pink satin purse for his lipstick and lace hanky. He didn't know it but the girls had also slipped a whole pack of condoms inside for a laugh.
"There, what a pretty girl."
"A real heartbreaker."
"A little darling?" Carol smiled, delicately pinning the lace headdress into his blond curls. "And in a moment darling, I'll show you how to pout, then you can really tease the boys."
"Yeah, and I'll show you how to snog them too" Christine laughed, spritzing him with her perfume.
At that moment the door opened and Sophie, the five year old niece swept in, followed by Lucy in her beautiful long satin bridal gown. "Oh he's precious, isn't he?" she laughed. "If you didn't know, you'd say he was a girl, wouldn't you?" she mused. "OK, we've just got time for one last rehearsal, girls. I want everything perfectly synchronised when we get to the church. You know what to do once we reach the altar don't you, girls? OK, so let Peter watch you first, then it's his turn. Pay attention now Peter. Just watch the girls and then I want you to copy what they do, exactly. I don't want any hitches, OK? Once Peter's got it, then all of you can practice together. Peter watched in horror for a moment then cringed at what was obviously to come at the church.
To be continued….
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