Jack-Jacqueline.

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Jack-Jacqueline.

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Jack Smith had just turned 18 and was sitting at home so forlornly. His growth hormone hadn’t kicked in. He had been to see a doctor who told him he needs to get some outdoor activity. They had done all they could for him and was hoping that exercise would encourage his growth. Because of his small stature, girls refused to look at him. He was only 5 feet 1inch and weighted roughly a measly 7 stone. He had tried but gave up looking at scales. He had a 25-inch waist and his chest wasn’t much more. Before he left school, all the girls in his class towered over him. They said he should have been a girl.

His mother despaired. How could never get a job. He would be no good at brick laying or any manual work. He needed to strengthen his muscles, but exercise seemed boring to him. Then things got worse. His father working abroad, had met someone else and was divorcing his mother. He blamed her for his short stature. His mother wept when she got the news. Jack did his best to console her. But it was no use. She was unable to stop crying. Jack suggested she phoned her sister Violet.

Jack last saw her when he was 10. She had three daughters. At the time they were smaller than him. He used to love it with his mates, playing cowboys and Indians and tying the girls up. Sadly, those days were long gone. He wondered what they looked like now.

Jack overheard his mother on the phone. “You were about to phone me?” Violet spoke but he couldn’t hear it, then Jack’s mum replied “Oh I am sorry hear that. I never got your phone call because the phone mast got broken in the wind and they only repaired it last week. I’d love to come up. Of course I will, you need support at this time. Okay, we will be there next week. Where can we stay?” Jack never heard the reply. His mum went on talking. “You have had an extension completed last month. Wow. That makes six bedrooms. It’s a mansion. Okay. I’m looking forward to coming up. It will take my mind off of things here. Love talking to you. I will talk to you later” Jack wasn’t listening when Pat gave Violet all Jack’s measurements.

Jack’s mum said Violet’s husband had died and left a lot of money. The funeral is in four weeks. You can catch up with your cousins” Scenes of his cousins struggling to escape their bonds while him and his friends danced around them came into his mind. She went on talking, “She lives in Scotland on a vast piece of land. Maybe there you can climb trees and go camping. The exercise might put things right”, but in the back of her mind she was worried what would he and his lusty cousins get up to when she wasn’t around.

The next day she phoned her sister and explained about her worries. Her sister said she had seen a way. One of her friends had told her that she put a chastity cage on her son. That caused the pair to laugh. But it put the idea in her head and she looked it up on line. A metal one would be best as it could remain in place for a long time. She ordered one and sent it to her sister’s address.

The week went by quickly. And on the day, they had to leave, Jack told his friends he wouldn’t be long. Little did he know what would happen. He said his goodbyes and went to the station with his mum. It was strange getting into a sleeping compartment. He wanted to look out of the window all night. But with the rocking of the train, it didn’t take him long to go to sleep.

When he woke up, they were already in Scotland. The train was just pulling into Crianlarich. “Come on sleepy head. Only four stops to ours” his mother told Jack. Jack got his wits around him and quickly pulled on his shorts and T shirt. A few minutes later and Jack had washed his face and hands. His mother was putting their stuff together when the announcement that the train was pulling into Corrour. “Here we are. I hope Aunty Violet is waiting for us. It looks desolate here” Jack had to agree. It was nice, but there weren’t any fun things to look at. “They must be hardy men up here to wear kilts” his mother said. Jack said nothing. She continued “Would you wear the kilt, Jack?” “No, I wouldn’t. I will not be seen wearing a skirt for anybody’ he said rather angrily. That was Jacks problem. He never listened to anything anyone ever said and then did his own thing. He never helped around the house either. That was something that made his mother, Pat, angry. If only he would do a little bit to help”

The train stopped and the door was opened for them. As she stepped out of the carriage onto the platform, there was Violet waving to her. She had brought one of her daughters with her. Jack looked at her and didn’t recognize her at first. “Hello Jack. You don’t recognise me, do you? It’s me Jane”

Pat sat in the front or the Range Rover with Violet. Jack and Jane sat in the back. “You’ve grown Jane. I had to take a double look at you” She was now a good 8 inches taller than him. The last time he saw her, he was a foot taller than her. “That is the life we lead here. It’s tough but we have fun as well. Do you remember how you and your mates used to tie us up in cowboys and Indians?” Jack said he did. He enjoyed it watching them struggling to escape. Jane went on “Rosie and Sarah are as excited to see you coming, like I am” “Why would you be excited to see me?” “Silly, we haven’t seen you for years have we” Jack was wondering how tall the other girls were. Jack noticed that she was wearing a very low-cut blouse, her silky white tits were very obvious. It wouldn’t take much to have her nipples slip out on display.

The car bounced over unmade roads, climbed steep hills, and dropped down into deep glens. Eventually they came to a made road and Violet turned onto it. “It’s a B road, but the way we came save a good 25 minutes” Pat answered it was certainly a memorable trip. Jack had been too busy watching Jane’s huge breasts bouncing up and down out of the corner of his eye hoping they would pop out of the bra and blouse. Even on the smoothish road, her breasts were wobbling like two jellies. Jack felt the stiffening between his legs. “Please don’t let her see it” he thought, covering his cock with his hands. Jane had seen his actions in the rear-view mirror and smiled to herself. She would get even before the week is out.

The road turned to the right and the occupants looked down the glen and saw Violet’s house. Pat gasped. It was beautiful to look at. “We have 10 acres of land over as far as that forest on the left there” Pat was astounded.

As the car pulled up, Rosie and Sarah came out of the house. Jack got out of the car just to find the shortest girl was still 4 inches taller than him. The girls rushed over and kissed him on his cheek. They picked up their cases and said they would take it to his room and meet him in the lounge.

Jack and his mum sat down and the girls brought the teas in. Jack thanked them which was a shock to his mother as Jack never said thank you. She said how well the girls behaved. “I wish Jack was like that” she said rather downheartedly. Violet smiled and her daughters gave each other a knowing look.

Pat said she would like a shower and suggested Jack did the same. He agreed. Off they went to the showers. Pat’s bedroom was ensuite, but Jack had to share the communal bathroom. Firstly, he was shown his bedroom. He was shocked. It was all pink. He moaned at Jane and she answered him, “What do you expect? We only have females around here. Only our friends come and they are girls as well. Mum can’t have the room redecorated just for you”. Jack agreed that made sense. Still once his eyes were shut, he wouldn’t know what colour the room was. He was clean and back in the lounge before his mother, mainly because he didn’t unpack but left everything in his case. Violet had gone to make them something to eat. Pat joined her in the kitchen.

The two women started to chat about Jack. Violet gave her the parcel Pat had ordered. Violet had no idea what it was. Pat told her, which made her laugh and want to see it. Violet said her girls would tame him. Pat doubted it. “Will you trust them to do it?” she asked “I’d give anything to see it” Pat replied, but how will they do it?” “They will get him to wear a dress and tease him. When I told them you were coming along with Jack, they jumped for joy. They said they finally had a chance to get their own back.”

His mother laughed at the thought and said he wouldn't wear a kilt let alone a skirt. Her sister said she could leave him there while she goes to Edinburgh to buy him a kilt. He will need that for the funeral and the Sunday church services. Pat thought about it and smiled. Violet gave her the money for the whole outfit. The list was 3 pair of socks 2 pair of shoes, sgian dubh, two kilts, one heavy weight and one medium weight, 2 jackets, two ties, 3 shirts, belts, kilt pins. “While you are there, get him some frilly panties. We can’t have him displaying all his charms can we!” “I can’t take all this money” Pat said. “Of course you can. It’s for Jack. It will make a man of him, or girl at least”

Pat looked at the £3000 that Violet gave her. “If you don’t go, I will” Pat smiled and said she would do it. Day one was soon over and Jack sat round bored. “There is nothing to do here. Can’t I go home? I’ll be with my friends” Day two saw him being shown all over the estate. But at dinner he said it was boring again. Later Pat cornered Jack in his room and ordered him to strip. She showed him the chastity cage and he asked why should he have to wear it.

“Because I don’t want your cousins getting pregnant and blaming you. That would ruin your life before it begins”. Jack begrudgingly said he supposed so but, in his mind, he was thinking of Jane’s soft tits.

Back in the lounge, Jane reminded him how they used to play cowboys an Indians. “We loved it. Fancy playing again?” “We are too old”. “Nonsense. We loved it and never had so much fun since” Sarah replied. “There is the forest and other places we can hide in. It will be new for you and an adventure. We still play it now and then to break the monotony” Rosie joined in.

Jack thought about it and said “I suppose it will be fun tying you lot up once more. Better than just sitting round here looking at the hills” Jack wasn’t aware of what was planned. “Every Christmas we have a Victorian Christmas. We all dress up in Victorian clothes. I’m sure Jack will fit into some of those clothes. They are not used these days. Thankfully, they were still in good condition for each of the girls to use as they grew up. They were used to hand me downs”

Pat asked “what about Jack?” “Well, we don’t have any boy clothes here. Think about it” Pat grinned. It was a chance for her to repay Jack for his laziness. Violet said she would tell the girls of the plan. When she did, the girls grinned. “If we can get our friends over to play with us, we can make sure Jack is out of the way when his mum goes to Edinburgh” Jane told her. That did it. The girls all phoned their friends and it was arranged.

The girls took some old blankets and stitched them up to make wigwams out of them. Pat said they were doing a great job. In the mean time Jack was exploring the area, looking for the best places to leave the girls and torment them like he used to do. He found a few places that was perfect for the job.

The very next day girls decided they would start playing again. “But we have a problem” Jane said. Jack asked what it was. “Well one Indian brave can’t capture three women, can he?” Jack said he could take one of the girls to be on his side as his squaw. “That won’t do. It would be hard two capturing two. We are stuck” Rosie said. Jack said they had better forget it. “There is a way” Sarah said. “Oh, and what would that be?” Jack asked. His curiosity now building up. “Well, no, forget it. You won’t do it" Jane knew that Jack could not resist a challenge. “Well come on then, what is it” Jane replied he wouldn’t do it. It was a silly idea. It would take someone of courage to do it”. Jack told them to run it past him and he would think about it. Rosie said, “We thought we could all change places. We become the Indian braves and you could become a woman trying to escape”

Jack laughed. “Me in a dress. Never” The girls called him a coward. “We will bet you that you can’t escape. If you do, we each pay you £10. If you can’t you will have to be a girl for another day”. Jack told his mother and she said it would allow them to play and it should be a laugh. Jack thought about what he would look like. He would look ridiculous. “Who will see you? There is only us here. Come on, don’t let them beat you over this. Show them that some silly girls can’t get one over a masterful man” Eventually, Jack caved in and said he would do it. He was thinking of the £30 he would get from the girls. The girls were delighted when she told them. But Violet had other ideas. “Is there anyone at home who could take a parcel?” Pat said there wasn’t but wanted to know why a parcel should be sent home. “I have a friend in Pitlochry. Shirley. She comes every year so owes me a favour. She will take it in. Let me phone her”

Pat still wanted to know what it was. “It’s Jack’s clothes. Once he is dressed up, I’ll take you to Pitlochry and leave his clothes there” Pat grinned. She was beginning to like the idea. That might knock some sense into him”.” We can buy his highland stuff there” Violet said. We’d only be gone a day. She is a teacher and a strict disciplinarian. Violet phoned her. Then told Pat that normally she comes by bus and it takes all day, but she could come back with us as it is school holidays” Pat laughed. The thought of Jack eating his words and wearing dresses and a kilt for best. No more trousers or shorts shot through her mind.

The girls spent all day making outfits to make them look like Indian braves. Jane became the Indian chief. Pat said they looked fantastic. They had attached long fringes to old sports bras, simply got some squares of material, sewn matching fringes on them and while wearing thongs, held the material up by putting a belt on and letting it fold back over the belt. Jack would get glimpses of their legs and bum cheeks. Finally, they tied scarves around their waists thereby covering the fold of the material.

Violet told them to be careful. “He is a male after all and is therefore stronger than you. It wouldn’t take much to rip those outfits off of you” Jane said everything was in place to keep them safe. Pat said she wished she was young again so she could wear those outfits. Jane said “that could be a plan. Make you the medicine man and mum the chief or vice versa” Violet and Pat said they would love to join in the fun. Violet phoned her friend once more to make sure it was okay and asked if she wanted to join in the fun. The woman Rachel, said “Just try and stop me. I have fancy dress outfit I could alter to make me look like an Indian brave.” All three women laughed once the information was passed on.

Jack got out of bed and took a shower. While he was in there, Pat told him his outfit was in his bedroom. When he went back in there, all that was hanging up was a long skirt. On the bed was a pair of full leg length cotton bloomers with lace trims at the ankle end of each leg, a waist scarf like a cummerbund, a full-length petticoat that was very slim, a corset and a further waist fitting petticoat that flared out and fitted with pretty pink bows at the hem. There were boots on the floor. He called his mother and she entered the bedroom. “I can’t wear these” Pat replied he could. He said he would do it and can’t break his word now. Jack had to admit it. It was true and he had never backed out of a dare yet. “Come on, it will be fun” she told him. “How do I put it all on then?” he asked. Pat said she would leave the room and he should replace his pants with the bloomers and then she would come back and help him.

Jack slipped out of his pants and carefully stepped into the bloomers. He eased them up over his bum and snapped the elastic around his waist. It felt strange. Although they were only cotton, they fitted him perfectly. It felt nice on his bum. It was tight, but not too tight. Just enough to let him know he was wearing them. The elastic on his ankles felt strange. They felt like handcuffs. Then he realised, there wasn’t a way for him to go to the toilet. Thanks to that chastity cage, he would have to sit like a girl. The cage stopped his cock feeling the cotton material of the bloomers. He started to get the urge but the cage stopped him short.
He called for his mother, but instead of her, the three girls came in. They never realised the bulge they were looking at was not his cock.

“Oh my. Very pretty” Jane said, “They suit you”. Jack blushed. Jane said “Come on girls we have work to do”. She held out a sleep bra and got Jack to slip it on. She put some huge balloons filled with jelly into the cups, Jack moaned they were too big. Jane said she thought he liked big breasts as he kept looking at hers. “I saw you sneaking a look” and then she got the full-length petticoat and slipped it over his head. Jane eased it right down to his ankles. She got some short nylon stockings and worked them under the ankle elastic of his bloomers. After that she put some boots on his feet and laced them up. She told him to stand up which he did. Rosie put the corset around him and the girls laced him into it pausing every while to allow the bones to relax.

He was told to step into the half petticoat. Once he stepped into it and it was pulled up, he couldn’t see his feet anymore. Jane asked him to walk towards her. He found he could only take small steps thanks to the first petticoat. Rosie got the skirt while Sarah got the blouse. The cotton blouse was pulled over his head and his arms through the sleeves. The high collar was buttoned up behind his neck and Jane did the other pearl buttons up enclosing his back. The blouse felt weird. It was ballooned at the top to near the elbow and then tight to the wrist. Sarah buttoned up the cuffs. Rosie got him to step into the skirt and she pulled it up. The three girls helped tuck the petticoat into the skirt.

They applied makeup, and Jack complained bitterly. “We might as well. It will make you laugh when you see yourself” Jane pipped up. Once the makeup was on, a wig was put on his head and a bonnet was tied under his chin. When Jack saw himself, he was amazed. “Come on Jaqueline, time to show our mothers what a lovely girl we have here” Rosie said.

“Jacqueline?” Jack cried out. “Well, we can’t call you Jake when you look like a beautiful girl can we!” Sarah said. Jake carefully walked own the stairs and into the lounge. Violet and Pat were there looking like a pair of Indian braves. “Wowee. What a lovely lady we have here” Violet said. “Give us a twirl” Pat asked. “Meet Jacqueline” Jane said, “Curtsey young lady” Jack laughed and curtsied as best he could. Violet got an apron and tied it around his waist. it went from his waist to his feet the same as the skirt and petticoats. Everyone was laughing by now. Jake asked how he went to the toilet. “You will have to pull the bloomers down like all girls do” Pat told him which caused more hilarity.

“Okay Jacqueline, you are a hunted woman now. Us braves are after you. You have a15 minutes start” Violet told him Jack left the house and found he couldn’t run that fast thanks to the tight petticoat, corset and the weight of the skirt etc. Another thing that got him was how hot the outfit is. He was sweating like he was leaking. It didn’t take him as long to get to the forest as he thought it would.

It took another 20 minutes for the braves to find him. He was gagged and ropes were thrown over branches and tied to his wrists. He was standing with his arms spread wide apart. He struggled but could not get free. The “braves” started to dance around him. Violet and Pat were on the upturned buckets that served as Tom Toms. The girls ran off and returned with a blanket and a picnic. They sat round laughing at the captive.

The girls kept lifting the skirt, “Lovely petticoats and those pretty bloomers, wow” Pat teased. Jack was squirming. “If you want to join us, you will have to escape by yourself” Jane told him. Jack mumbled something back. “Oh, she doesn’t want to be untied does our Jacqueline.” Everyone laughed. Jake was embarrassed as he had been caught by the girls and was unable to escape. Violet spoke next. Do you know Pat, our girl is so pretty, she should go to church in that outfit next Sunday. Pat and the girls all laughed but Jack was squirming. However, at the same time there was something that he was beginning to like.
These clothes were hot and comfortable. Eventually Jane asked if he wanted to be untied. He nodded he did so they released him. He sat eating the picnic food with the girls. He said he liked the outfits they were wearing but his made it too difficult to run. Jane told him not to worry as he would have to try again tomorrow in a different outfit. “What, I have to dress as a girl again?” “Of course you do. That was your bet. But the clothes won’t be like this” Sarah told him. Jack knew she was right but was hoping the next day would be shorts or leggings at least.

The next day saw him in panties and his sports bra with the huge balloons again, but this time it was a long hobble dress. It was zipped up behind him and he was told he had one hour to hide himself. Away he went. The girls looked at the clock. It was 8.30. Pat asked where the clothes came from. “The girls made them or altered what we had” Violet replied.

The phone rang. It was Violet’s friend. “Oh crikey, we have to pick up Shirley today. Run after Jack and tell him we have to go Jane” Violet said. “Okay girls, lets go” Jane said to the others. Once outside she said they were not to rush.

Jack struggled to get as far as he could. The three girls phoned their friends and they scrambled. Jack reached the forest and headed to where he thought he would be safe. As he went into a clearing, Ten girls jumped out in front of him. He panicked and by the time he got his wits back, his cousins were there behind him. “Okay girls, lets get our prisoner tied up” Rosie called out. Jack was grabbed, his hands tied behind his back. Then they cleave gagged him. A rope went around his waist and he was told the were taking him back to Violet’s place.

He was dragged and pushed by the thirteen girls. Jane told him he would be too hot in that hobble dress so should go and put a skirt and blouse on and report back for being tied up again. “Keep the gag in”. Jane ordered. He was grateful for that and in his room found a knee length cotton full circle skirt and a satin blouse. They quickly tied his hands behind a post and wound rope holding him tightly to it.

Jack saw his mother getting into Violet’s car. He tried to reach her but was stopped short by the girls. Pat told him she was taking his clothes, but he has plenty to wear. Jack’s heart fell. Clothes there were, but they were all girls’ clothes. He tried to scream that he should be released, but Jane said the girls will look after him. They quickly tied him to a tree and he had to watch as Violet and Pat drove away.

“Right girls, now we have a prisoner, let’s get stuck in” They lifted the skirt and pulled down his panties just to find his chastity cage. “What the hell is this?” Sarah asked. Through his gag he tried to tell them his mother had stuck it on him. Rosie suggested they pull down the skirt and panties and leave him. All the girls agreed. He stood there quite exposed while the girls went off and left him. Two hours later, Jane came back and lifted her skirt and rubbed herself along the shaft of the cock cage. She was soon moaning that she was getting hot but not enough to have an orgasm. Jack was moaning that he was getting aroused but that cage was stopping him.

An hour later, in the lounge Jane explained it was a nice feeling rubbing herself on his cage, him being locked up made it even more pleasurable. All the girls should try it. They all walked out to Jack. Jane did the talking. “Right Jacqueline. You have a choice. We don’t expect our mum’s to be back today, so we can either leave you here all night like you are, or you can agree to become Jacqueline for the length of time you are here. What is it to be? We can always tighten the ropes and add a lot more if you like”. Jack looked down at his huge breasts and said he would become Jacqueline. He didn’t know that Violet had sent off for some fake breasts and the glue they use for women that have had a mastectomy. She had told Jane and Pat and gave Jane the authority to open the parcel.

That turned up that afternoon. Jane opened the parcel lifted Jack’s blouse and bra and removed the balloons. She wiped his chest with some spirit and after a couple of minutes, spread the glue on the breasts and inserted them into the bra cups and put everything back in place. Brushing the satin blouse down Jane said “you must be randy. Your nipples are getting engorged”. All the girls laughed. Jack found the extremely large breasts rather heavy.
He was released an hour later as it was nearly six in the evening and it was time for dinner. “Come along Jacqueline. It’s time you learned how to cook.” Rosie said, tying an apron around his waist. Jack was halfway through cooking the meal when Pat, Violet and Rachel turned up. “Oh, lovely Jacqueline. You have got into the part already. You look very pretty, but that wig lets you down” Pat said.

After dinner, all the girls (the friends had gone home by then but promised to come back to play with Jacqueline) and the three women sat round. They said it was time to finish Jack off. When he had washed up he returned to the lounge to find they had set up a chair. He was tied to it while they set about painting his nails and applying make-up. Violet set his hair into a female style for him. It didn’t take long for them to finish the make-up.

“Right Jacqueline. We are off to church tomorrow and I expect good behaviour from you miss. Rachel said quite sternly, “Tomorrow, I will teach you how to cook and sew like a proper girl should do things” Violet said that the glue will take time before it gives up so for the while he is Jacqueline. Pat told him his Highland outfits will be here in a few days. If he is a good girl, she will let him start to wear a man’s kilt.

Violet turned on the television and pressed aa button. It showed Jack tied to the post and Jane massaging herself on the smooth cock cage.” Good job you put that cage on him. I didn’t realise it would be my girls who were randy” Violet said. Pat said “we were once” Violet had to agree.

Jacqueline was dragged to the church the next day. Violet had told all the villagers he was being trained not to be so impudent. All the kids already knew of Jacqueline’s plight. Jack was hoping the ground would open up and swallow him. The only thing he knew was, he had no male clothes except kilts which he wore to the funeral the following week.

Violet had to thank Pat and Jack for taking her kind off of her loss. Jane said Jack wasn’t to worry, they loved tying him up especially dressed as a girl. Rosie and Sarah grinned, “All girls together aren’t we” Violet offered to let Pat stay permanently and said she would have her barn converted. Pat agreed. Jack realised he was never going to see his old life ever again.

A few weeks later, Pat told him the truth, “You know your old jeans and underwear and shirts etc” Jack said of course he did. “Well Jacqueline, I prefer you like this. We never left your clothes at Pitlochry. I paid the grave digger to dig down another foot and I threw your clothes in the hole then covered them with dirt. They are under your uncle’s coffin if you want them” Jack realised he had been present when his clothes were buried. Jack started to weep when Rachel said it was time for him to put his apron on once more to do some more cooking lessons.

The girls were happy when their mother let them go on the pill and Jacqueline could have the cage removed. “I can’t wait to tie you to the bed in your nice pink baby doll nightie”, Sarah said, her lust building up after all the weeks of not being able to get at Jack. He was moaning how his huge breasts would not come off but was ignored.

Violet, Pat and Rachel were discussing about Jack. He needed a job. “Well, as he is doing well at the cooking, how about giving him the job of a maid?” Rachel said. Violet and Pat agreed. Jack had just found out although the girls wore shorts and jeans, he would never see such luxuries again. In his wardrobe was just dresses, skirts, blouses bras and lots of frilly panties of all colours. He complained and the girls told him they remember how he used to look at their knickers. Well now it is their turn.

Violet took Pat and Jack into town. Jane went with them. This time she was grinning as she looked at his huge breasts bouncing up and down.

Two years on and Jack shot up. He met a girl who he married. He thought his past life was over until she said, ""I'm buying handcuffs, more rope and getting you some more pretty panties okay. I wear the trousers here. You need new breast forms and some bras as well".

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JaniceNoyb
Tightly Hogtied
Posts: 204
Joined: 26 Apr 2019, 15:27

Re: Jack-Jacqueline.

Unread post by JaniceNoyb »

Very nice. Sure wish I had cousins like those girls!

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