Author Topic: Teenage Heiress (Read 42846 times)

DaraJaney · « **Reply #7 on:** September 24, 2006, 05:31:27 PM »

On the drive home he didn’t dare ask his mother if she was going to take Mrs. Frankfort’s advice seriously. He had dreamt the last few nights of wearing trousers again and couldn’t handle having his hopes dashed.

His mother parked outside their house. He jumped out of the car and ran up the footpath as fast as his heels allowed, clutching his skirt so that his stockings wouldn’t show. He could practically feel the cotton of the trousers brushing against his legs. He wanted to get into a pair before his mother could object.

He pushed open the door and headed straight for the staircase. But he was stopped in his tracks. “Surprise”, they all shouted with his Grand Aunt standing smiling in the middle of the family group. “Just look at you”, she gushed, studying his cerise outfit and high heels. She took his hands and pulled him into the middle of the room. Lesley wanted to cry but managed to keep smiling somehow.

When he finally got to the privacy of his bedroom he rushed over to the wardrobe and opened it hopefully. But there was no sign of any trousers – not even the girls’ trousers that he had before his Grand Aunt arrived. The wardrobe was chock-a-block with dresses and skirts and blouses.

Lesley threw himself on the bed and burst into tears. He was clearly going to have to spend even the Christmas break in skirts. Was he ever going to get to wear a pair of trousers again?

There was a gentle knock on the door. Lesley looked up, grabbed a few tissues to dab at his eyes, checked that his skirt was not askew and invited the person in. It was his mother. She saw the tracks of mascara on his face.

“Oh, what’s wrong dear?” she asked as she came over. “What’s wrong?” he repeated incredulously. “Only that I’ve spent six months wearing dresses and skirts and stockings and suspenders and slapping thick make-up on every day!” “Oh you poor thing”, she said as she smiled sweetly. He didn’t think she was taking this seriously enough.

“Can’t I even wear a pair of girl’s trousers for just a few minutes?” he begged. “It would only make you feel worse, believe me”, she told him. He sighed and realised she was probably right actually. If he got into a pair of trousers for the first time in six months he would never want to take them off again. “It’s much better if you just accept that you’ll have to wear dresses until you’re finished school. It’s only another …” and then she stopped when she realised this wasn’t much consolation.

Eventually Lesley’s tears dried up. “You’ll have to re-do your make-up dear”, his mother told him, “before you come down for dinner.” He heaved a sigh, stood up, straightened his skirt and plodded over to the mirror.

Going to Midnight Mass on Christmas Eve, he had to wear the outfit his Grand Aunt brought for him. He stood in front of the mirror and winced. There was no point in arguing about it any more with his mother. He had to wear it. With the red, hooded jacket lined with white fur, he looked like a Ms. Clause. He wore a tight red mini-skirt over white wool-knit tights and red high-heeled boots also trimmed with fur above the ankles.

His only consolation when they went out into the frosty night was that the wool knit tights were considerably warmer than the stockings he usually wore. Outside the church he tried to ignore the amused looks. He cringed as he saw his Grand Aunt stride all the way to the front pews. He had no choice but to scamper after her with his heels making a racket that made everyone turn to look.

His Grand Aunt had also brought a festive dress for him to wear on Christmas morning. It was Christmas-tree green with a pattern of red holly berries. There was a three-inch lace trim around the neckline and on the end of the sleeves. There were four-layers of cotton petticoat underneath, each with a broderie anglaise trim. Lesley reckoned it looked straight out of the 50s except that the hemline was well above the knee. His mother helped him freshen up his curls and insisted on tying red ribbons on either side for the day that was in it.

She left him to finish dressing. He sat on the side of the bed and rolled up a white stocking. As he pulled the stocking up his leg he caught sight of himself in the mirror. With his leg raised the four layers of lace-trimmed petticoats were on full view and together with all the lace trim on his dress he couldn’t have looked more sissyish.

He fastened two suspender straps to his stocking, took the other one and rolled it up. He stood as he fastened that stocking, desperately trying to hold up his petticoats with his elbows.

With his stockings done up, he held his petticoats up for a moment longer and looked wistfully at the bulge of his tackle in his silk panties. It was the only remaining sign of his manhood and when he let his skirts go it was quickly buried beneath the layers of white cotton petticoats and nobody could ever guess what was there.

He trudged down the stairs with his skirts swaying back and forth around him. His brothers had been eagerly anticipating his latest outfit. “My, what a pretty dress Lesley”, Roy sneered. Lesley made a face and stuck his tongue out. He looked just like a spoiled Mammy’s-favourite little girl and his brothers laughed even harder.

But as soon as he heard his Grand Aunt coming through from the kitchen he switched to a sweet smile. She practically squealed with delight at his appearance. His mother came behind her with a big smile.

Lesley clutched his skirts coyly and swished them about with what he hoped looked like enthusiasm. “Give us a twirl”, his Grand Aunt commanded. Lesley obliged, raising his arms to allow the skirt and petticoats swirl about him. His Grand Aunt clapped her hands with delight but then turned to his mother with a slightly disappointed look. “Does she not have any nice lace-top stockings?” Lesley abruptly terminated his twirl, pushing his petticoats down as he realised that he had been a little two enthusiastic. His brothers looked like all their Christmases had come at once.

DaraJaney · « **Reply #8 on:** September 27, 2006, 06:56:24 PM »

Back at school in the New Year, Lesley had struck up a friendship with the girl in the next room, Nancy. She was very bubbly and outgoing and it would be almost impossible not to like her.

One Friday towards the end of January Nancy told him she was planning to sneak out of the school that night and head into the nearest town for a dance. She insisted that Lesley come with her. He generally preferred the relative privacy of the school but it was very claustrophobic at the same time. Nancy wouldn’t take no for an answer and told him she would come into his room after lights out.

When she appeared, she brought an outfit for him. She had somehow managed to get the corset and five-inch heels that were used to dress recalcitrant girls as sluts. Lesley winced when she indicated that she wanted him to wear the corset. “You’ll need it to fit into the dress I have for you”, she insisted. He didn’t like the sound of that.

Luckily they needed to keep the light off to avoid being noticed, so Lesley was able to change without Nancy suspecting that anything out of place. He grasped the bed-frame as she pulled the corset tight. But even at that, the dress wouldn’t fit. Lesley was quite relieved actually because he didn’t want to wear it or the corset.

Nancy untied the strings on the corset but then said “just a little tighter”. Before Lesley could protest, he was silenced by a further tightening and she quickly tied a knot. He was still struggling to breathe as she pulled the dress over his head and down tightly over his hourglass figure.

Lesley was so restricted that she had to pull up his black stockings and attach them to the straps on his corset for him. She took the five-inch heels and, despite his pleas that the usual shoes would be fine, she strapped them onto his feet.

Nancy was determined that they were going to attract attention, so she applied his make-up in the dark. He couldn’t really appreciate the pink lip-gloss in the gloom or the heavily applied mascara.

As Nancy gathered her stuff together in her hand-bag, Lesley felt around the hem of his flared dress. It was very short but in the dark there was no chance of checking if his stocking tops could be seen. He would have to trust her on that. The material felt very flimsy and left him feeling even more exposed. She gave him a tiny fur jacket that didn’t look like it would provide much warmth.

They tip-toed down the corridor, which was relatively easy for Lesley since the shoes had him on tippy-toes to start with but it was incredibly painful. They climbed out a window at the end of the corridor. Lesley’s corset did not make such manoeuvres any easier.

It was a freezing frosty night but Nancy seemed to be unaffected. Lesley shivered and longed for a good pair of wool-knit tights.

The main gates were not an option since the gardener lived in the lodge beside it. Nancy made for a tree that overhung the six-foot wall. Lesley couldn’t understand how there was any chance of him climbing the tree and getting over the wall in the corset and shoes.

When they reached the tree, Nancy took off her shoes. Then she removed Lesley’s. He was momentarily relieved at getting his feet on the flat again but then he was distraught at seeing her throw both pairs of shoes over the wall. There was no going back now.

Nancy carefully climbed the tree, expertly avoiding any damage to her dress or stockings. This was clearly not the first time she had done this. Lesley followed and was amazed that despite his corset, he was actually able to climb and move out a branch over the wall.

They jumped down the other side and the only damage done was a little tear under his left foot. He wasn’t pleased though to have the five-inch heels strapped on again. It was half a mile into town and he was certain his feet would never be the same again.

They arrived at the dance and headed straight for the ladies toilet to check on their appearance. Lesley couldn’t believe his reflection. With his hour-glass figure, short red flared dress, glossy make-up and stiletto heels he knew he had the appearance of a woman out to get a man.

He didn’t want to leave the toilets for fear of what would happen out there but Nancy headed happily for the door and he had no choice but to scamper after her. She headed straight for two guys who were watching the dancers. “Hi, I’m Nancy and this is Lesley”, she said and fluttered her eyelashes. The two guys obviously couldn’t believe their luck.

Nancy immediately started chatting up the dark guy leaving Lesley standing awkwardly by the blond guy. They exchanged uncomfortable pleasantries. Lesley just wanted to be out of there.

The music changed to a slow song and Nancy pulled her guy onto the dance floor. Suddenly Lesley found himself being pulled out there by the blond guy. He wanted to resist but in the tottering heels had no option but to try to keep up.

He found himself in a firm grasp with the guy’s head already on his shoulder. His instability in the shoes forced him to hold on tightly, which was misinterpreted. The guy’s hands moved all over his body, clearly relishing the curves that his corset imposed on it.

Within a couple of minutes, Nancy was tugging her guy towards the exit. Lesley’s partner saw them go. He waited a while, clearly hoping that Lesley would be as proactive but quickly ran out of patience and pulled him towards the door.

Outside Lesley looked around for Nancy. He saw two figures in a dark corner. He could make out Nancy’s shape. She was on her knees in front of the guy and he was groaning.

Lesley found himself pinned up against a wall. The guy started kissing him around the neck and the hands wandered around his waist. Next thing they were down on his legs working their way up under his dress. The guy felt Lesley’s suspenders and emitted a satisfied grunt. When his hands went towards the danger area, Lesley slapped them away.

The guy went back to the suspenders and stocking tops and seemed to be satisfied with that for a while. But soon he was trying to push Lesley down on his knees. Lesley was having none of it and after a while they took a time-out. Nancy and her beau were similarly getting their breath back.

The two guys joined up and starting lighting cigarettes. Lesley and Nancy conferred a few yards away. “You are going to give him a blow-job aren’t you”, Nancy asked him showing concern. Lesley shook his head disapprovingly. “Listen honey”, Nancy explained, “these guys know we’re from the school and could make life very difficult for us if we don’t show them a good time. So you’d better get down on your knees and either give him a blow-job or pray that you won’t spend the next six months in that corset and in those heels.”

With that she headed back to her guy and a stunned Lesley was rejoined by the blond. He hoped that the guy wouldn’t try to push him down again but he did and Lesley had no option but to comply.

When the couples next met up again, the blond guy had a very satisfied grin while Lesley had a stunned look and was constantly wiping his mouth and swallowing hard.

It felt like miles back to the school as Lesley winced his way back with the shoe straps cutting into his feet, whitewash from the wall on his dress and half his lip gloss left on a guy’s dic-k.

DaraJaney · « **Reply #9 on:** October 15, 2006, 07:57:33 PM »

The following summer Lesley’s Grand Aunt returned from America to be with him during his summer holidays. He was pretty much resigned to the fact that he was condemned to dresses and skirts for the foreseeable future.

She told his mother that she wanted them all to visit some friends of hers. These were a very well-to-do family who lived in a country mansion. She took great care that Lesley dressed elegantly for the visit. She brought him for a fresh perm and manicure and bought him expensive earrings and bracelets.

He wore a powder blue jacket and a-line skirt with matching four-inch heeled court shoes and barely white sheer stockings. The family were very nice and a lovely dinner was laid on. Afterwards his Grand Aunt suggested that the son, Arnold, should bring Lesley for a walk in the garden. Lesley was taken by surprise by this but had little option but to consent.

During the walk it became obvious that Arnold was trying to flirt with him. Lesley noticed him sneaking glances at his legs whenever he thought he could. It was intensely uncomfortable for Lesley but he returned to the house somewhat relieved that nothing had developed.

However, the following week his Grand Aunt proudly announced that Arnold had asked if he could take Lesley out on a date. Lesley was shocked and looked at his mother hoping she would say it was impossible. But he was told instead that it would be rude to refuse.

He pleaded with his mother when alone with her but she was insistent that he had no choice. They couldn’t insult that family after they had been so nice to them. She advised him that a subtle way of showing Arnold that he had no interest would be to dress very casually for the date.

On the evening of the date, Lesley was helping his mother with the washing up. His Grand Aunt called from upstairs “Lesley it’s time you were getting ready for your date.” Lesley winced at his mother. “Go on. Just wear something very conservative and a minimum of make-up. Just show him that you’re going through the motions of accepting a date without having any intention of it going anywhere.”

Lesley went upstairs. His mother heard his Grand Aunt say “I have something special for you to wear.”

When she led him downstairs an hour later he was wearing a very tight red dress. He’d had to wear a corset to get it to fit. It had a really short pleated skirt and he had to pull it down as hard as he could to get it to cover his stocking tops. He’d already shortened his suspender straps as much as possible to pull his stockings up as high as they would stretch and he felt the strain with every step. He tottered along in five-inch heels.

His lips were heavily painted with scarlet lipstick which was greatly emphasised by a white-ish foundation on his face. As he stood in front of his mother he looked downwards in embarrassment and she saw the blue eye-shadow as his heavy mascara fluttered.

The doorbell rang and his Grand Aunt hurried to answer it. He looked desperately at his mother but knew that it was far too late for a reprieve.

Arnold was shown in and the grin on his face when he saw his date made it clear that he reckoned he was in for satisfying evening. He had a box of chocolates which Lesley accepted with an embarrassed smile.

After a little idle chit-chat Arnold suggested that they should be going. Lesley reluctantly took a few careful steps towards the door in his five-inch heels. Arnold stepped forward and took his hand firmly. He strode towards the door eagerly and Lesley had to scamper in his heels to keep up. He looked back despairingly at his mother, clutching his purse in his other hand. She saw his dress ride up revealing a thin line of lace stocking-top.

Arnold’s sports car was at the kerb. He opened the door for Lesley who was concerned that the car was so low. His five-inch heels did not help at all. He tried to hold the hem of his dress as he stooped to get in. Once he was seated, Arnold closed the door. Lesley looked down and the full lace stocking tops were visible as well as an inch or so of suspender strap. He was certain Arnold must have seen. He squirmed desperately in the seat trying to pull his dress down. Arnold had a very smug look on his face when he sat into the driver’s seat.

They went to a posh restaurant. Lesley only picked at the expensive food. The corset made eating uncomfortable and he was highly nervous anyway. He couldn’t wait to get out of there and was relieved as he was shown back to the car.

But Lesley became aware that Arnold was not heading for home. He was heading up into the hills overlooking the city. Lesley just wanted to get home to bed. He could hardly breathe in the corset. He was tired tugging on the hem of his dress and his feet were killing him.

But Arnold pulled into a viewing point at the side of the road. Inevitably he tried moving closer to Lesley who sat nervously clutching his purse on his lap. Arnold lunged to kiss him and Lesley tried to push him away. They struggled for a moment and Arnold managed to plant his lips on Lesley’s. He also moved a hand up his leg and felt around the suspender strap with a snigger.

Lesley managed to push him away but Arnold was not pleased. “Why did you dress up so sexy if you weren’t interested?” he protested. “I think you really want it”, he concluded and lunged again.

The next time Lesley pushed him away he said “do you fancy walking home from here?” Lesley was terrified of the idea of being stranded up in the hills dressed as he was. Arnold leaned across him and threw the door open.

Lesley felt he had no choice. There was only one way to get out of this. He put his hand on Arnold’s lap. Arnold lay back in the seat and closed his eyes. Lesley unzipped him and slid his hand inside. He massaged but felt Arnold’s hand on the back of his head pushing him down. He resisted but Arnold warned “it’ll be a long walk in those heels”.

Lesley allowed himself to be pushed down and he took Arnold in his mouth. Within a few seconds hot c-um was squirting into his mouth. He tried to withdraw his head but Arnold was pressing him down firmly and didn’t let go until he was entirely spent. “You’d better not get a drop on this upholstery”, Arnold warned. Lesley carefully withdrew his mouth and swallowed with a shudder.

It had done the trick. Arnold started the car and drove home without a word. He left Lesley at the kerb, realising that there wouldn’t be a second date. The car sped off and Lesley tugged his dress down for the umpteenth time. He took a mirror out of his purse and examined his lipstick. He had to touch it up. Then he painfully walked towards the door wincing with every step and still shuddering with the taste of the sperm.

DaraJaney · « **Reply #10 on:** October 19, 2006, 07:27:35 PM »

The next morning Lesley was getting dressed when his bedroom door suddenly opened. His Grand Aunt walked in and stopped in her tracks. Lesley had nothing on but a pair of pink frilly panties. His Grand Aunt looked at his flat chest and then down at the bulge in his panties. Lesley folded his arms across his chest – way too late.

They were in deep doo-doo. Any number of the family could go to jail, given the serious deception they had tried to weave. Lesley and his mother sat with red-faced shame as his Grand Aunt dictated to them what was going to happen now.

A few days later, Arnold’s family in the country house were surprised when his Grand Aunt begged them if they would take Lesley on as a house-maid. She explained to them that the girl was a brainless bimbo quite useless at anything else and they would be doing her a big favour if they could just take Lesley in for bed and board.

They were further surprised when she led Lesley into the drawing room. The five-inch heels did not really seem suitable for a full day of house-work. Also, his movement was considerably restrained by the size 12 corset he was tightly laced into. The eight layers of white fluffy petticoats under his black maid’s dress did not seem very practical either. The dress was so short and flared that if Lesley did manage to bend over in his corset to, say, plug in the vacuum cleaner, he was surely going to expose his underwear.

Lesley trotted over in front of Lady Waltham and clasped his white-gloved hands coyly on top of his skirts. His eyes were firmly on the floor-boards in front of her feet. “Lady Waltham will be your mistress now”, his Grand Aunt told him. Lesley daintily took the hem of his maid’s uniform between his forefingers and thumbs and lifted it as he curtsied giving a splendid view of his petticoats.

Lady Waltham had to suppress a smile - she couldn’t remember the last time she saw a maid curtsey. Still, there was no need to disabuse this girl of her archaic habits.

Lesley was told to report to the butler in the kitchen for instructions. He curtsied again and turned towards the door. Lady Waltham noted the perfectly straight seams on his black stockings.

As he minced over to the door, she expressed concern that his stiletto heels might be bad for the recently refurbished floor boards. Lesley stopped and bent over slightly to look down at the floor. Lady Waltham was treated to a view of his lace stocking-tops and his pastel pink panties with three rows of white lace on the bottom, all framed by the layers of white petticoats.

That night, Lesley stepped very gingerly towards his bedroom on the top floor. He had spent twelve hours in the five-inch heels and every step was torture. He made it to his bed and flopped down with his petticoats parachuting around him. After a minute or two to gather himself and tried to bend far enough to unstrap the shoes.

In the end he had to take off his dress and loosen the corset in order to be able to reach the straps of his shoes. He lay back on the bed, his feet still moulded into the shape of the shoes and gradually tried to ease his toes back into line.

When he had recovered sufficiently he explored the room. The wardrobe contained one identical maid’s dress that would not come near to fitting him unless he was squeezed into the corset. On the bottom of the wardrobe was another pair of black shoes with five-inch heels.

The chest-of-drawers contained a few pairs of seamed stockings and white gloves. The only variety was provided by a dozen pairs of frilly panties in various bright pastel shades.

The next morning he tugged and tugged at his corset strings for twenty minutes before he could squeeze into his uniform. He spent another hour with the curling tongs and make-up. His mood was not improved by the knowledge that he was going to have to serve as a maid in the household as long as his Grand Aunt was alive. She seemed hale and hearty to him and apparently her mother lived to be 95.

He brought a tray of full English breakfasts into the dining room. Arnold and his four brothers sat around the table. Their mother wondered aloud if they would have enough work for a maid. “Oh I think we’ll find things for her to do”, Arnold said with a smirk and his brothers sniggered.

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