Betty Pearl's Sissy Stories 20.1
Sissy Story Archives (older stories) => 2011-2018 Sissy Stories => Topic started by: DaraJaney on September 02, 2018, 02:07:37 AM
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One of Alan’s best friends, Monica, was getting married. He was having a drink with her the week before her hen party was planned. “You should come”, she told him. “It’s a hen party! It’s going to be all your girlfriends.” “Yes but you are one of my best friends, I want you there too!”
“I don’t think they would appreciate that”. “It’s my hen party, I should be able to decide. I’ve told them I don’t want any nonsense like themed costumes or stupid veils or L plates.” “I don’t know”. “Look, let me talk to them. I’m sure it will be ok.”
So Alan got a phone call from Hannah, Monica’s bridesmaid. “Seriously you should come. She really wants you there – and so do we.” So that settled it.
They booked into a hotel on the Friday night and spent it all in the bar having great fun telling old stories – mostly ones that had embarrassing outcomes for Monica. It was a late night but they didn’t have to be up early. When they eventually got up on Saturday morning they cruised the shops in town. Alan didn’t feel at all awkward – they were all nice to him and there were no silly jokes about him being the only guy.
In the afternoon Hannah suggested that they should all have a nap in preparation for the long night ahead. The other girls agreed but Monica and Alan didn’t feel the need so they just went for a walk. “Let’s all gather in my room at 6. I’ve got a bottle of vodka ”, Hannah suggested and they all readily agreed.
When Monica and Alan approached the door at 6 there was much tittering inside. “Sounds like they’ve made inroads into that bottle of vodka already”, Alan commented. They walked in and found the girls all dressed up in slinky, short, low cut, brightly-coloured dresses, high heels, big blond and brunette wigs and heavy make-up.
“Oh no!” Monica winced. “You promised there wouldn’t be anything like this!” Hannah stepped forward and pulled her into the room. “Come on it’s just a bit of fun! We’re …..” “TROPHY WIVES!” they all shouted and laughed. Alan cringed on Monica’s behalf. He knew she hated this.
“Come on!” Two of Monica’s friends grabbed her by the elbows to bring her off to another room. “Wait til you see what we’ve got for you!” “Oh no!” Monica protested. “And it’s not fair on poor Alan. He’ll feel totally out of it.” “No he won’t”, Hannah insisted and she and another girl grabbed him and tugged him towards the bathroom. “What the ….?”
When Monica returned to the room she was wearing a figure-hugging pink dress, high heels, a blond curly wig and make-up laid on with a trowel. Then Alan was brought from the bathroom. She put her hand to her face. He was wearing a tight very short scarlet dress. They had given him very big boobs – he had the biggest in the room she reckoned. His dress was not low-cut like all the others but continued up to a collar – presumably to conceal his prosthetic boobs.
They had him in large high heels. She wondered had they waxed his legs but realized that they had put him in tan opaque tights which were remarkably effective. He had a brunette wig and the same exaggerated make-up as the others – scarlet lipstick, false eye-lashes, copious blush. Flashy earrings dangled from his lobes. Long scarlet false nails had been glued on. This made it very difficult for him to tug his dress down which he was desperately trying to do.
“Where did you get all that stuff?” Monica asked. “My brother is a drag queen”, Hannah explained. Monica felt so sorry for Alan. She looked incredulously at his wig. He reached up to it self-consciously and his dress rode up. She saw his bright red panties. He desperately tried to pull his dress down again but the nail extensions made it very difficult to get purchase on the material.
She had expected to see a bulge in his panties but none was obvious. There was something else instead. She went over to him and pulled the front hem of his dress up much to his embarrassment. The panties they had dressed him in were specially designed to conceal his tackle and present the outline of a vulva instead. She couldn’t help laughing. Alan desperately pulled his dress down again.
Hannah handed him a handbag. “There’s a spare pair of panties and a spare pair of tights in there along with your lipstick and blush.” The others all giggled. Alan looked in terror at his spare panties as the full realization hit him that they were taking him out in public like this!”
“No please! You can’t be serious.” Another friend helped him on with a little jacket. “The restaurant is booked for 10 minutes time”, Hannah insisted. They all got their bags and coats. Alan cringed in his high heels but they were ignoring him. Monica hated this too but there was no stopping it now. She gave him a sympathetic smile.
Two girls grabbed his elbows and he was led into the corridor. When the door was shut behind them they let him go, confident that he had little choice now but to come with them. They headed for the lift but he remained reluctant standing in his heels. Then a door opened at the other end of the corridor and a man stepped out. Alan scampered after the girls, not wanting to be left alone in the corridor in his tight red dress and eye-catching boobs with this man approaching.
But of course his only refuge was in the lift which delivered them all to the busy hotel lobby. There were people waiting to get into the lift so he had to follow the girls out. He got some funny looks but then they all looked like drag queens anyway so he wasn’t as noticeable as he’d feared.
They all strode purposefully towards the hotel entrance except for Monica who lingered back to smile sympathetically at Alan who was struggling to keep up in his unfamiliar heels. Then he was out on the street. He shivered, whether from the cool air or exposure in public in a short dress, who knows, but he instinctively tried to pull his dress down yet again. Damn these nails!
There was no stopping them and he had to scamper down the street after them. The further behind he was, the more passing men tended to notice his extra large boobs. Many looked towards the hem of his short dress and he desperately hoped that his panties weren’t showing but couldn’t be sure. He tried to trot along faster to catch up.
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such a delicious DILEMMA to be found stuck in..if only it were me.. (sighs) :-[
locked out of the room and led by already woozy Women... The night just starting..
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DaraJaney, I don't know how you can be so creative and prolific at the same time. Particularly love that all the girls and Alan are dressed the same so he can't be singled out unless he messes up. I think the girls just want him to have the same fun they are having. Hope they don't undermine his friendship with Monica. Many thanks for all your great stories.
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They finally reached the restaurant. He was very relieved to get inside but it was packed with people staring at this mad group that had entered. Everyone laughed but he wasn’t sure if it was because they could see that he was a guy in drag or not. At least he was soon able to sit and get the weight off his heels and get his crotch concealed safely under a table.
“They were very naughty giving you those panties”, Monica sympathized sitting down beside him. “I wonder if the spare pair are the same”, he responded opening his handbag. He took out his spare tights and then his panties. He examined the pack. “Damn!” They had the same shape as those they had dressed him in.
The meal proceeded and much drink was consumed. After the main course, Alan leaned over to Monica. “I need the bathroom.” “I’ll come with you”, she insisted grabbing her handbag. They both tottered off giggling arm in arm. He was tickled by the idea of being one of a pair of girls going to the bathroom together.
He found a stall. The one advantage of his short dress was only having to pull it up a little to be able to pull his panties and tights down to pee. His tackle was relieved to be getting some fresh air. But he had no choice but to parcel it up again afterwards. He looked at his fake vulva and sighed. There was nothing he could do about it except go panty-less which he really didn’t want to do.
He emerged to find Monica touching up her make-up in the mirror. She encouraged him to fix his lipstick and blush again. She smiled at his fluttering eye-lashes as she looked him in the face to study his make-up. They had been expertly glued on – as had his nails.
The meal went on and then Hannah announced it was time to go on to a bar. Alan whispered to Monica that he needed the bathroom again. She was deep in conversation on the other side but acknowledged him with a wave of her hand.
He went to the Ladies alone. There was a queue. Typical! He thought. He got a lot of funny looks from the women in the queue – especially his big boobs and long legs. This was his first time away from the others so he did now stick out like a sore thumb. He thought the people in the stalls were taking ages but assumed that it just felt like that in his desperation to get away.
When he finally emerged from the toilet there was no sign of his group. He tottered over to their table as quickly as he could in his high heels. All the coats and bags were gone. “Oh no!” He scampered towards the door having to frustratedly zig zag between the tables. Every second counted. He went out on the street and looked up and down. No sign.
He cringed. He was out in public in a very short slinky red dress, large boobs, long seemingly waxed legs, high heels and heavy make-up. And he was alone. He no longer had the cover of the group. He tottered off towards what looked like the busier end of the street. There were a couple of pubs there. He heard a few cat calls behind him and tried to ignore them scamper faster while tugging his short dress again. Men stopped and stared as his boobs wobbled as he passed them.
There were no windows on the pubs and he couldn’t see if the girls were there or not. The pubs looked pretty down market so he doubted they would choose them for a drink. He went around the corner. A group of men in an unmistakable stag party approached. “Woah!” “Look at her!” “This must be our stripagram!”
He was terrified and cringed in his heels, once again trying to pull his dress down. The stag party group all moved towards him. He really really didn’t want to encounter this very drunk group dressed like a bimbo as he was. Then the door of a limo opened at the kerb. “Are you in need of assistance?”, a man in a suit asked. “Oh yes please”, Alan responded and climbed in. He looked down to see that his dress had ridden right up as he stepped in and his fake vulva was on display. He had to wriggle to pull his dress down again. The man was smiling.
“I’ve lost my hen party”, Alan said in as womanish a voice as he could muster, unsure if it was obvious that he was a guy in drag. If the man knew, he didn’t let on. “Oh dear! Benson”, he addressed the driver, “drive around the streets here and see if we can spot a hen party.” “Yes sir”, the driver pulled away from the kerb.
Alan squirmed in his tight short red dress realizing how vulnerable he was, sitting in the back of the car with this man. He scanned the streets desperately but couldn’t see Monica and her friends. “This club is popular with hen parties”, the man said, “Benson pull over here. We’ll go inside and you continue to search the streets.” “Yes sir”.
Alan tried to get out of the car in a dignified way in his high heels and tight dress but inevitably found himself trying to pull his dress down as he tottered in his heels on the pavement. The car pulled away and the man led him to a stairway down to a basement club. Alan clutched the handrail as he negotiated the steps in his heels. The bouncers looked up from the doorway and Alan wondered what they could see up his dress.
“Evening Mr Charlton”, they chorused and ushered them in. After a swift scan of the club, it was clear that his party wasn’t there. “Let’s have a drink while Benson continues to search”, the man suggested. Alan thought he was safer here than in the back of the car so he agreed and was led to a sofa. Mr Charlton ordered a bottle of wine.
Eric sank into the seat and once again struggled to pull down his dress because of his long false nails. The bottle arrived and was uncorked. Alan thought that there was little chance it could be drugged so he sipped his glass.
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Alan tried to respond to Mr Charlton’s small talk but really he just desperately wanted to be out of here. He really didn’t want to be in a nightclub in a short tight red dress, very large boobs, fluttering eye-lashes, long legs in tights, high heels and panties making him appear to have an inviting vulva.
Half-way through the second glass of wine Mr Charlton’s phone vibrated. Benson had found a hen party in another club. Alan struggled to his feet out of the sofa and tugged his dress down. He scampered up the stairs, all too aware of Mr Charlton looking up behind him.
They drove a few streets away to another basement club. Once again Alan tottered down the stairs, the bouncers welcomed Mr Charlton and Alan scanned the club. This one had dancers in cages on the tables. He spotted a hen party giggling in the corner but it wasn’t his. He sighed and shook his head at Mr Charlton who ordered another bottle of wine.
Alan sat on a mercifully upright chair at a table with an empty cage. He found that looking at the scantily clad dancers got a reaction in his panties that could prove awkward. At least there wasn’t one gyrating directly in front of them. He was stuck. He had no room card for his hotel. He had no idea when the girls would get back except that it wouldn’t be early.
He sipped his wine and after a while Mr Charlton asked if he danced. He wasn’t sure if he meant did he want to dance or was it just idle small talk. Alan shrugged to indicate that he did but wasn’t enthusiastic about it. Mr Charlton stood and took Alan’s hand. Alan assumed that he wanted to dance and looked around for a dance floor but couldn’t see any. But Mr Charlton helped Alan step up onto the chair and then nudged him into the cage on the table. The cage shut automatically behind him! When he turned around he couldn’t see where the door in the cage had been.
People looked up at him expectantly. This was going from bad to worse but he couldn’t create a scene. So he had no choice but to start gyrating to the music. He tried to discretely push his short dress down as he danced. The attention of his audience seemed to be divided between his very large boobs and the hem of his dress.
Mr Charlton had stepped back to observe and another man sat at the table. Alan felt very uncomfortable under this man’s gaze but had little choice but to continue dancing. After a few minutes the man nodded to Mr Charlton who came over to him. The man was picking through his wallet.
That’s it, thought Alan. He was going to be bought, tied up and gagged in a crate on a boat to be sold in Africa as a white sex slave! Just then he saw lots of bare legs through the basement window to the street. Could it be his hen party? Were they going to come in and see him dancing in a cage in front of a man with his wallet out?
They appeared in the door. It was Monica and Hannah and the rest! He waved desperately. Monica was astonished not just to see Alan dancing in a cage but to see him seemingly waving at them to get their attention. Hannah spotted the man with the wallet and quickly assessed the situation. She took out her purse and waved her notes in the air, pointing to Alan.
Mr Charlton realised that Alan’s party had arrived and played along. He took the money from Hannah and magically the cage opened. Hannah helped him down from the table. Then she went to the wall where various items of bondage equipment was displayed and took down a collar and leash. The girls cheered and giggled as she collared Alan and dragged him off to a back room.
Alan was dumbstruck when she threw him down on a sofa and climbed onto him. She pulled his panties and tights down and mounted him. It was amazing. She was clearly experienced in this area.
So Alan was saved and the girls had an amazing hen party story about how he was almost sold into prostitution. Alan was more than a little shook by the experience but had the consolation that Hannah wanted to see him again.
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Thanks so much for writing another wonderful story.
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Another exciting chapter,, LOCKED in the cage and almost sold.. I wanna have it happen to me too!
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Hannah invited Alan over for a home-cooked meal. They had barely finished desert when she led him into her bedroom. He wasn’t entirely surprised to see lots of bondage gear around but the room was entirely decorated in dark reds and pinks with a four-poster bed!
She started to undress him and threw him down on the bed to pull his pants off. She climbed on top of him. “I’m afraid I lied”, she told him. He looked perplexed. “I didn’t have all that stuff because my brother is a drag queen. It’s all part of my work”, she said. She reached over the side of the bed and picked up his strap-on boobs.
He frowned but she insisted and pulled them over his arms. She had his red dress again. Pretty soon he was squirming on the bed in his tight dress, tan tights, fake vulva panties and high heels, his lips painted scarlet. But she was clearly expert at satisfying a man and coaxed him persistently, knowing just when to touch him up and when to push him a little further. The sex was absolutely great so he let himself go with it.
The next time she wanted to dress him up as soon as he arrived. An hour later he found himself in a black maid’s dress which barely contained his big boobs, black stockings and suspenders , frilly black and white panties, white lace-trimmed apron, five inch heels, fluttering false eyelashes and straight dark wig with lacey headpiece. She made him dust the bedroom with a feather duster which involved lots of bending over and reaching up into the corners.
Eventually she pushed him down on the bed and he smiled realising that the sex was going to happen now. But she reached down the back of the bed and pulled out shackles which she quickly locked around his wrists. Within seconds his ankles were chained to the foot of the four poster and she was tugging on the chains pulling his stockinged legs further apart.
She paced up and down teasingly as Alan pulled and struggled against his restraints. “Resistance is futile”, she spoke in a movie-villain accent. He relaxed a little more convinced that it was a game. She climbed aboard and he enjoyed her teasing him for a long while before she eventually pulled his panties down and completed the job.
He lay there panting still spread-eagled on the bed. She disappeared into the bathroom to freshen up. She eventually released the ends of the chains from the bed but they were still locked around his ankles and wrists. “I’m not done with you yet”, she told him.
She led him towards the wardrobe and opened it. There were lots of sexy outfits on either side but the middle was empty apart from iron rings set into the back wall. She pushed him in and proceeded to lock his wrists and ankles to the wall. “It’s about time you saw what I do”, she told him. “You will have to be quiet”, she explained pushing a leather gag into his house and strapping it tightly behind his head.
She closed the wardrobe doors and he could see through the downward slanted slats. Almost immediately the doorbell rang. She smiled towards the wardrobe and went to answer the door.
So Alan had to watch as she undressed her client, tied him to the bed and performed just about every sexual act on him that did not involve anything penetrating her. Once he had recovered from his own climax he naturally got very aroused watching all this.
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DaraJaney,
I'm really enjoying this story and you are really pushing the right buttons on a number of my fantasies about being forced to dress as a maid and being chained under a woman's control.
I'm looking forward to reading your next chapter.
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The next time Alan visited Hannah she wanted to show him something else. She could see how he liked being teased – he didn’t disagree – so she locked his tackle in a chastity device. His pen-is was held in a small hard plastic tube which curved down to counter any erection. It was locked on with a plastic ring behind his testicles.
He was once more dressed in his maid’s uniform. This time she collared him and attached the collar to the wall beside the bed. She chained his ankles to a ring in the floor and handcuffed his wrists behind his back. As she gagged him she told him “this time you’re going to be part of the act”. It was too late for him to object, though his muffled whimpers could be heard through the gag.
She placed a leather blindfold over his eyes and strapped it tightly in place. “I won’t make you watch it though. Let’s leave it to your imagination.”
Then she took a tray and chained it to his collar and around his waist so that it rested beneath his big boobs and just above his apron. “Somewhere to keep our drinks.” He flinched and whimpered when the doorbell rang. She hadn’t been joking.
He heard her leave the room. He struggled against his restraints but he was securely attached to the wall by the neck and by his ankles to the floor and there was no give in his handcuffs. Her client was led in to find Alan wriggling, whimpering and squirming helplessly which Hannah was pleased about.
“This is my useless unemployed husband”, she explained. “At least he has plenty of time to do all the housework!” He heard the man chuckle. “Hold these for us dear.” She placed two tumblers of whiskey on his tray.
They sat on the bed. “Don’t worry, he can’t get any enjoyment out of this.” She lifted the petticoats of his maid’s dress and pulled down his frilly panties revealing his locked up bits. He heard another chuckle. She left his panties around his chained ankles.
Alan could only hear it but that made it worse. The last time he hadn’t seen her allow her client to enter her but it sure sounded like something like that was happening. His member pressed against his chastity device but he was denied any arousal. He continued to whimper and tug on his chains, not sure himself if it was real or if he was putting on an act.
The next time she chained him at the end of the four-poster bed with his wrists locked to the top of the posts and his ankles locked to the bottom. He was gagged but not blindfolded this time. His panties were pulled down his legs to show his chastity device.
“I want my useless husband to see how it should be done”, she told her client who was only too keen to oblige. This time there was no doubt that she was engaging in full sex. Alan tugged desperately on his chains in what was definitely not an act. However, she unlocked everything and gave him a good seeing to afterwards so he seemed to forgive her.
The next time the client entered to find him dressed in his maid’s uniform, chained ankles and wrists in the open wardrobe. A tube was attached to his pen-is which was vibrating away. “This is my useless unemployed husband. This way I get something worthwhile from him which I can sell to the sperm bank. I can’t bear to do what is necessary to him to extract this stuff myself but this nice machine does the job.”
Alan groaned through his gag as the tube pumped away on him. She held up the narrow plastic tube which led to a bottle about one third filled with sperm. “Just a few more times to fill it dear!”
After a few minutes he came and she turned the machine off. She looked after her client very well as Alan looked on, still panting from his orgasm. As her client was leaving, she turned on the machine again. Alan groaned in protest but was soon distracted by the pumping on his pen-is.
It took longer and longer for him to come each time. She’d leave him for an hour and come back and turn it on again. Despite his groans and pleas she actually seemed determined to fill the bottle. She picked it up and examined it. “You really need to produce more each time dear or we’ll be here all day”, she told him turning the machine on again and leaving him there chained up in the wardrobe groaning in protest as she left the room.
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definately different. Unemployed hubby should now be trained as a sissy maid. Made to answer doors maybe gagged...lol
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I feel like I've missed something, when did he become husband? I hate to sound critical, the situations are very good, but the story has felt rushed since the actual hen party ended. It's felt like a different tale.
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Any chance this story gets finished it was interesting
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i agree when did he become a husband? but i do like what she is doing to him. Lets him see that he is useless.
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Clarification: he didn't become her husband. She was pretending that he was her husband to give her customers a greater kick thinking he was a cuckold.