Jack and Jill

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Jack and Jill

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Jack and Jill used to laugh at their names and the nursery rhyme. Jack always said he’d get a pail of water and throw it over her. Jill used to say that once he had finished tumbling down, she would wrap him up head to toe with vinegar and brown paper.

They had been going out for eighteen months before Jack proposed. Jill wanted to get married earlier but Jack insisted that they should get the house of their dreams set up first.
The months went by and the wedding drew closer. They decided to discuss their fantasies and lay down the ground rules for a successful marriage.

At Jill’s hen party she was tied up and dragged around the bars. Unfortunately she was wearing a cut down wedding dress and veil. Jill’s knickers were exposed when she was bent forward. Her hands were tied to her elbows behind her back so she couldn’t defend herself.

Jack found himself wearing budgie smugglers, and pulled by a chain fixed to a collar. His hands were cuffed by short chains to the collar as well. He could not protect himself either
All night the pair was dragged around. Both had sore bums from the continuous patting they got and Jack’s cock was as solid as a rock from the rubbing the girls in the bars kept giving him. When he started to complain, he was gagged.

The day they got married, they were both virgins. Everyone thought it was strange. As his best man said “you should always test drive a car first before buying”

As the music started up, Jack turned round to see this vision of loveliness walking towards him escorted by her father. The sun shone through the church window behind her and lit up her veil and the outline of her silk dress. She looked like an angel. Murmurs of “oooh” came from the congregation.

The wedding ceremony was over quicker than they thought. But they enjoyed the reception. As Jack took her for the first dance, he held her waist and one hand. Jack told her she looked beautiful and she felt lovely in that dress. Jill smiled. She said he looked handsome in his suit. But she would have liked him in a kilt. When he asked why, she simply said “Easy access” and smiled again. Slowly they waltzed all around the hall. Sadly the day ended all too quickly.

Once they got home, Jill went to take the dress off but Jack asked her to keep it on for a while. When she asked why he told her that he had been reading a book on how to please a female. Jill wasn’t sure about it, but sat down. Jack slid his hands under her dress and slowly removed her panties. That took Jill by surprise. She realised her fears he might be gay for waiting was unfounded.

Jack lifted the hem of her dress and eased himself up to her body. He put his mouth into a large O shape and gave Jill a gentle blow. That was the second shock Jill had. Slowly he kept licking around her sex organs and finally licked her clitoris. It was like an electric shock to Jill. Her back arched automatically and Jack kept licking and kissing.

Jill exploded into one almighty orgasm that sent shock waves throughout her body. She was trembling with excitement. Her waters gushed all over Jack’s face. When he withdrew from under the dress, he had to go and shower. Jill slipped out of the dress and Jack came back naked. Jill guided him into her body. Moans of happiness came from both their mouths. They lay there kissing and Jack slowly started to thrust his body backwards and forwards. Jill had another orgasm. Although she had a few self-inducted orgasms, this was a thousand times better.

Jill removed her undies and lay there naked with Jack. She loved the feeling she was getting with them spooning. Jack’s now semi erect cock was resting between the cheeks of her bum pointing downwards towards her feet.
They fell asleep and it was quite late when they arose. Jack made the breakfast for them. They had to get ready for the honeymoon. Soon everything was washed up and stacked away. The cases were packed and they had an hour to wait before the taxi would arrive to take them to the airport. A few drinks passed their lips which although didn’t make the drunk, it relaxed them.

Jill started the conversation. “Jack, you know on your stag night and my hen night, we were both tied up” Jack said it wasn’t something that could be forgotten in a hurry. Jill carried on, “I might seem a bit weird, but I enjoyed it” Jack agreed he did. Jill carried on talking, “Did you know they were going to blindfold us and tie us up together?” Jack said he didn’t know that, but it would have been fun. “Fortunately my maid of honour pointed out it would be unlucky for us to see each other”
Jack spoke next, “So what are you getting at?”

Jill looked a bit sheepish, “would you object to bondage”

“Thank heavens for that. I wanted to ask you, but was too embarrassed”, Jill laughed.

The honeymoon over and the pair went back to work. A few months later Jill came home to find a letter. She opened it: they had been invited to a fancy dress party. Jill was looking forwards to it. Jack was not sure. They didn’t have a lot of spare money to buy or hire outfits. Jill said she would think about it.

“You could go in your swim trunks” Jill told him. Jack said he would not do that. He was game for most things, but would not go through that again. They had time so they could think about it.

A few days later, Jill said she had been talking to the girls at work about the party. They suggested that she goes as the groom while Jack became the blushing bride. Jack wasn’t sure about that. He didn’t want to make himself look stupid. Jill said she would go under the dress and return the favour he had done for her on their wedding night. Up to that point, she was not interested in giving him a blowjob. But this did it for him. He agreed. Jill said she would get her friends around to fix them up. Jack was hesitant, but the thought of her under the dress was too much to resist.

The following Saturday saw Jill getting all her stuff from her wardrobe while Jack got his. The girls turned up. They said they should start on Jack as there was more to do. Jack was shaking with excitement at being forced into the dress and at the mercy of the girls.

He was handed the white panties and told to put them on and come back when they were in place. Jack did as he was told. A corset was put on him and he felt the strings being tightened. It eventually became hard to breathe and Jack moaned about it. Jill told him she had to go through it so why shouldn’t he?

One of the girls took some socks and put them in the cups. White stockings were rolled up his legs and clipped to the corset. “You should shave your legs to wear white stockings” he was told, It doesn’t matter this time as you are wearing a long dress. A blue garter was slid up his leg. The girl let it snap on his thigh.

He was wondering where Jill was all this time. The petticoat was strange to him. He had to raise his arms and it was slid over his head. The girls smoothed it down for him and splayed the skirt out. The dress was put over his head and pulled down. The dress had lots of tiny buttons on the bodice part. These were done up for him.

To his surprise another of the girls took out some white heeled shoes for him. He didn’t think they would fit, but they fitted perfectly. Fortunately Jack had got small feet. He looked in the mirror and saw himself. The dress reached the floor. It should have done, as he was the same height as Jill.

The girls started with the makeup and eventually some pearl earrings were clipped on and had to have a little glue to hold them there. The wig was put on him and the girls fussed and gave it a bride’s hair style. He was told he looked the part. Finally he was given the veil.

The girls said he looked beautiful. “Just like a beautiful princess. Princess Jacqueline” Once they said that, they called for Jill. She entered the room looking for all intents and purposes like a man. “Wow” she exclaimed, “He looks better in it than me”. The girls laughed that Jill had lost her wedding dress, but had gained a suit. Jill and Jack laughed with them.

One of the girls made them some coffee and they sat round talking about the party. They assured Jack no one would think he was gay. “Most cross dressers are straight. They just like the feel of the soft material” That made Jack feel better.

Jack said it was time to get changed again, but was grabbed and tied tightly to the bannister post. “You are the dutiful wife now. You do as you are told”

Jill was told that for the party it would be better if they swapped names. Jill agreed. Jack didn’t like the idea until he was told that people would think it strange for a bushing bride called Jack. To stop him talking they gagged him.

One of the girls suggested that at the party the vicar they had would be attending. It was obvious she would go as a vicar. But the church needed to raise funds. Jack and Jill could help.

Jill asked how and was told, “Well people like a laugh. How about for your first anniversary, you renew your vows except you go dressed as each other. People would pay to be in the congregation. Jack wasn’t sure, but the thought was in Jill’s mind. The girls all said they would love to see Jack in the dress once more.

When the girls left, Jill did as she promised and slid under the dress. Jack soon let go and she felt him go limp as his sperm shot across her face. Now Jack was hooked on wearing a dress as well. He couldn’t see her, but felt what she was up to.

At the party the pair was the talk of the night. Everybody loved the outfits and even the men admired Jack for doing it. The vicar said they looked beautiful. When Jack was out if range, Jill and some of the girls raised the idea that on their first anniversary they could renew their vows and get people to buy tickets to see it to raise money for the church repair. The vicar loved the idea. It was agreed with that it will happen even though at that point Jack had no idea.

The vicar said they were having a prom night; she would love them to go. Jack heard that one and agreed.

Jill hired a ball gown while Jack wore his suit. They had to wait another three months before they had their anniversary. Jill was worried that her wedding dress would get ruined with Jack keep wearing it, so she looked on line for a cheap one for Jack. She also found a man’s suit that she could alter to fit her rather than wear Jacks.

When they turned up, Jack asked why the wedding dress. “Because you looked so lovely in it and it turned me on”. Jack said he wouldn’t do it until Jill told him no more sex unless you agree. He agreed so they retired to bed for the session that day.

Jill altered the suit for herself with the aid of the girls. Now for Jack’s dress. This one was made of satin and had sleeves that buttoned up at the cuffs. It was tighter than Jill’s dress. Instead of being a flared but not quite meringue style like Jill’s dress, it was straight at the skirt.

Jack tried it on and Jill told him he couldn’t wear stockings and suspenders. They would have to be tights. Jack asked how they were supposed to stay up when his hips were the same size as his waist. Jill said she would think about it.

”If you wear stockings and suspenders, your manly bulge would show. The only way to get round that is for you to wear a panty girdle” Jack didn’t like the thought of that but Jill said she would get one that would hide his tackle and not show a panty line.

A week later, one turned up. When she got it out of the box, Jack could see it had long legs and a high waist. Jill said they should try it out. Jack went to put the thing on over his pants but Jill pulled him up. “Oh no you don’t. If you want to be dressed like a girl, you have to wear the panties” Jack removed his pants and put on some satin panties.

The tights went over that and the panty girdle was pulled up tight around his waist. The bra was put on him and some fake breasts were put into the cups. He put the dress on and Jill told him the dress didn’t hang right. He needed a petticoat. Another week and the petticoat turned up.

Once again Jack was transformed into a blushing bride. Then he asked what it was all in aid of. Jill told him, “It’s for our one year anniversary. We are renewing the vows, except this time, I’ll be the man and you will be the blushing bride” Jack went to object so Jill took his index finger and slowly sucked it. Jack knew immediately what she was getting at.

“But with all this clobber on, how can you climb under the dress and do it?” Jill replied it will make it more fun by slowing it down until the act came.

“So how does this make money for the church?”

“Because the vicar has been selling tickets to it and has got one hundred and fifty people all paying twenty pounds each for the pleasure”

“That’s three thousand pounds” Jill agreed with him and then told him there were also donations as well.

“Are you going to do it? I promised the vicar you would. The girls are coming round to get you ready again”

Jack said he would but was annoyed it was all planned behind his back. Jill was secretly smiling to herself. She had a few little surprises for Jack.

Came the day and the sun was shining. Jill had to go to her old matron of honour’s house while the girls got busy with Jack. He was already in the underwear when the girls turned up. “Oh, you look like a real lady in that girdle. No bulge to be seen anywhere. You sure you are not a girl?”

The petticoat went on and then the dress. Jack felt the zip being pulled up trapping him in the dress. He was handed some white gloves which reached to his elbows. “Saves putting false nails on and varnish as well” Jack was happy with that.

They put the wig on him and the earrings once more. The wig was given the bride style again. The shoes were slipped onto his feet. He was ready once his makeup was finished.
The girls slipped upstairs to put their bridesmaid’s dresses on. Or so they told him. They all came down wearing men’s suits. Jack went to complain but was handed a bouquet of flowers. As he went to take them, one of the girls slapped some handcuffs on him. “There, that should hold you. Jill has the keys so we can’t let you out”. They put the veil over his head once more.

The girls were ready to leave when the doorbell rang. Jack heard male voices and in walked all his mates. They were wearing the bridesmaid’s dresses. They told Jack the car would be there soon to take them to the church. Jack was stuck and he knew it.

Then he found the surprises Jill had for him. She had altered the dress so it was tighter in the leg area. He could only take short steps. Jack heard a click. One of his “bridesmaid’s” had locked the zip of the dress shut.

“Sorry mate, your husband has ordered you be locked into the dress” When Jack said he couldn’t take it off anyway because of the handcuffs, the men just shrugged.

Jack tried to back out, but his mates pushed and shoved him into the street where he was met by a crowd of people. He got into the car and his bridesmaids straightened his dress for him. “We couldn’t let you do this on your own, so we told the girls we would be your bridesmaids for the day”.

Jack walked into the packed church very slowly. He had no choice thanks to the alteration to the dress Jill had made for him. He looked straight ahead at Jill in her suit. Once he reached the altar, the vicar thanked him and told the congregation how much Jack’s efforts had made. Jack heard the round of applause.

Once the ceremony had been done, Jill kissed him. At their local pub, they had a party and Jack was made to dance with all the girls while Jill stood there laughing.

Back at home Jill wanted to remove his girdle but said she had lost the keys to his handcuffs and the lock on his dress. Jack went mad so Jill got some rope, lashed his feet together and told him to calm down. She knew where the keys were. Jack asked to be let out but Jill said she was enjoying it so much, she was going to leave him there all night.

She did relent and let him out of the dress. Jack was grateful as it was so hot in it. Jill agreed he did look hot, but in a sexual way.

They agreed that once a month, they should swap places and he became the wife for a weekend. Jill bought him all sorts of underwear and skirts along with blouses.

Jill’s favourite thing to do with Jack is to get him to wear a short skirt and tight blouse and either hogtie him on the bed or simply tie him to a chair. Either way, she got to see his panties and when she was ready, play with his cock until he was ready to cum, but then stop and leave him frustrated. She could play with him for hours like this. Or she would put him over her knee and spank him for being such a slut by exposing his panties.

Jack liked returning the favour. Except one night when he had Jill tightly bound and the lads turned up and dragged him to the pub. Jill was left struggling for hours. She was thinking she would kill him. Her friends could see she had the hump with Jack. So could his friends.

It nearly happened. One of the girls told Jill that she was having a party where each couple had to come identically dressed. Jack said she could wear her suit but the girls said it was more fun if they were dressed as girls. Men’s clothes are more boring. Jill got the order of the day. It had to be micro skirts and tight blouses.

The day of the party, they got a taxi to the house where the party was. Jill rang the doorbell and they were let in. The girl was in a schoolgirl outfit. As soon as they got to the lounge they were jumped on. Everybody was dressed normally. They tied them back to back, gagged them and then tied their legs together. The girl who let them in went and got changed.
All evening they stood there with everybody tormenting them. Jacks cock was aching by the time the party was over. They had not had a drink all night, but once they were released, they were given a bottle of Champagne.

Back home, Jack had one objective in mind. He pulled Jill to the bedroom and they spent some time doing the bedtime waltz. Both were well spent within the hour.
Jill said that she loved seeing Jack dressed as a girl. She wasn’t gay but for some reason knowing it is Jack really turned her on. Jack said he loved her in the miniskirts. He suggested he bought her a French Maids’ uniform. Jill said she would wear one as long as he did the same.

Looking sweetly at him she said, “Maybe we could throw a party and us two as the maids for the evening” Jack laughed. He thought she was joking, but when Jill went to bed that night, she dreamt of Jack walking about with her friends tormenting him. But that was for another time.
We have ways of making you happily suffer. You WILL enjoy yourself. That's an order.
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