Crystal's StorySite


Sissy Trap - The Shopping Trip

by Josie Brian


"After breakfast we are going shopping. You are going to buy new clothes for your sister to replace the ones you stole. At the same time we are going to get your school uniform for next term and you had better take better care of it this time".

As Martin undressed for bed he thought about what his mother had said. Looking at the state of his school trousers he could see why she had been so annoyed. One pocket was ripped, the knees are stained and the hem on one leg had come apart. It had been a good fight and she should see the state of the other kid. He hung his clothes next to the green dress with the hoop skirt that he had to keep in his wardrobe. The dress his sister had specially made for him, it was easy to put on but he did not know how to get it off again. That's how she had caught him.

In the morning, Martin was relieved to hear that his older sister would not be coming to town on the shopping trip, he would be going with his mother.

Mum told him "Before we go, I need to see how Josie's clothes fit you. Go change into the leather skirt now and let me see how it looks"

Martin pulled the leather mini skirt on over his jeans and went to stand in front of his mother.

"Oh no, I don't think so. You can't wear your jeans as well, get them off"

Then his mother lifted the skirt a little higher on his waist and checked how tight the waistband was.

"Make him go to town wearing a skirt" Josie pleaded

But there was no need to worry about that, his mother had no intention of letting him disguise himself as a girl. Anyone who notices him today will know he is a boy buying girls clothes.

He was then told to change clothes again and wear the dress he had stolen from his sister.

Once again Mum inspected how the dress fitted. "It does not hang properly, do you normally wear a bra when you play with Josie's dress?" After admitting that he did, Martin had to put on a bra under the dress.

Satisfied that she knew what the correct size for Josie would look like on Martin, Mum allowed him to change back into his own clothes but he had to keep wearing the bra.

On the bus, Martin noticed a girl in another seat lifting her bra straps into place and suddenly realised how clearly he could see the outline of her bra through the t-shirt she was wearing. 'Is my bra easy to see? Are the people behind me looking at my bra straps and laughing at me?'

By the time they reached the fist shop, Martin was near paranoid that everyone was looking at him. In fact, the bra did show through his shirt but not really enough for most people to notice. Of course the staff in 'La Senza' would spot the obvious signs but would not say anything.

Entering the lingerie shop, Mum gave Martin a roll of bank notes and told him to pick 3 pretty bras and 4 pairs of panties for his sister. He would not have to try these on, just be careful to select the correct size. She made him change his choices a few times and spend nearly an hour browsing through the lingerie. Carrying the bras and panties on their hangers, Martin joined the checkout queue praying nobody he knew would se him. He quickly explained to the cashier "they're for my sister" but she just accepted the payment and said "Keep the receipt safe, the bras can be exchanged if you find they are not comfortable but we can't accept the panties back if they have been worn".

With him heart pounding and sweat running down his back; Martin rushed out of the shop to meet with his mother. Next stop would be JJB Sport shop.

In the sports store, his mother led Martin to the girls' swimwear section. There was a pink bikini very similar to the one he had taken from Josie's room. The trouble with bikinis is the sizing is not consistent. He could not just pick one from the shelf and buy it; he would have to try it on to see if it felt the same as Josie's.

Martin had been embarrassed in the lingerie shop, but had never felt so shamed when he had to ask the shop assistant for permission to use the changing room. The assistant gave him a disk marked "3 items" after counting the 3 pink bikini sets he was carrying.

Having chosen the bikini that fit best, his Mum gave him a pair of shorts to try, ready for the next school term. He came out of the changing room wearing the shorts to show his mother that they fitted ok. His mother quickly held 3 dark blue sports skirts to his waist and told him to try on the 3rd one.

Pushing the skirt away, Martin protested, "I didn't take any of Josie's sports skirts Mum. I don't need to get one of these"

Looking straight into his eyes, his mother said, "Go take those shorts off and put this skirt on now! The less fuss you make, the less people will notice you"

Returning to the changing rooms, Martin could hear one of the other cubicles was occupied. The voice answering a mobile call confirmed it was a girl. Martin rushed behind his curtain and put on the skirt, then hurried to show his mother before the girl came out. The skirt fitted well enough and Martin was very lucky to get changed into his normal clothes without attracting any attention from other shoppers.

Kelly Wilson met her friend Wendy near the running shoes department of JJB. She could hardly believe the amazing picture she had received while trying on a swimsuit earlier. If only she had not been completely naked when the message came, she might have seen the boy from her class wearing a netball skirt. Keeping a distance they both watched as Martin Brian carried a pink bikini, some shorts and a skirt to the tills.

Martin and his Mum made their way to Marks and Spencer and chose some new school trousers and shirts. Each time, he would present himself to his mother wearing the new item before being allowed to change again. Nobody had said anything to him in the sports shop but for some reason a group of girls were giggling like crazy when he wore a boys trousers and shirt. What he had not realised is how clearly his bra showed through a plain white shirt.

Then he was led to the girls' section of M&S to look for a leather mini skirt. It had to be red and no longer than mid-thigh. He picked up 3 skirts and took them to the boys changing rooms. Wearing the skirt he thought was most like his sisters, he stepped out of the changing room to show his mother. The skirt was very tight, as his sister is smaller than he is. His mother made sure it seemed the right fit, the same as the original skirt had earlier.

Just out of sight, Kelly and Wendy watched in shock – and took several pictures with their phones.

Martins' mother handed him 4 school grey skirts and told him to show her the best one. He started to say, "Josie doesn't need a school skirt" but realised he had better just get on with it. He came back wearing a very tight pencil skirt but his Mum told him to pick a larger size. On the third attempt he was wearing a pleated grey skirt, about knee length that fitted his waist comfortably. Thinking 'this skirt is too big for Josie' Martin realised it was meant for himself. On the way to the checkout, his mother dropped some girls' knee socks into the basket.

The final stop was Dorothy Perkins, where Josie had bought her denim dress. Used to the routine, Martin took 3 dresses to the changing room. 'This is almost over' he thought. Choosing the dress that felt just tight enough to fit his sister, he left the cubicle and walked straight into Kelly Wilson. She laughed so hard she fell to the floor. The noise caused every shopper in the store to look directly at Martin, very obviously a boy and most definitely wearing a blue denim mini dress. His mother rushed to his side and after a very quick check told him the dress was ok and he could get changed.

With his mother to order Kelly and Wendy away, Martin left DP in tears. At least he could go home now and forget about all that had happened – right?

Wrong! He had one final shop to visit – he had to replace the high-heeled shoes he had borrowed from his sister. She refused to wear anything he had touched. The shop assistant did not look impressed as Martin walked up and down her carpet wearing several pairs of stiletto heels. Looking through the shop window he could see two girls holding mobile phones, pointed towards him.

It was a huge relief when they got home and all the clothes he had bought met with Josie's approval. If anything did not fit or if she did not like it, he would have to return the item and chose another.

Almost afraid to ask, Martin spoke to his mother, "Mum, why did we buy a school uniform skirt and sports skirt? Please don't tell me I have to wear them to school, you saw how much I would be laughed at"

His Mum explained, "It's quite simple really. The 2 skirts are yours to wear to school. You don't have to wear them, ever – but if you rip your trousers or lose your football shorts like you did last term, the skirts are all you will have to wear; I won't buy you any replacement trousers or shorts."

The school rules on uniform had changed last year to allow girls to wear trousers, thanks to some international law case. The wording of the new uniform rules just says:

"Uniform for Boys and Girls between ages 11 to 16

Black or grey trousers (full length to ankle) or skirt (length within 2 inches of knees)

Blue or white shirt or blouse (to be tucked-in to trousers or skirt)

White knee socks or dark tights to be worn with skirts


Martin realised that if he were not careful enough to look after his uniform trousers and sports kit, the school would not stop him being sent to classes wearing a skirt as long as it matched their rules. He also realised that all the clothes he had replaced for his sister were now his. Along with the sissy-trap dress and the new girls uniform, all of these skirts and dresses and underwear had to be kept in his wardrobe. He was not allowed to wear any of them, and if he was caught who knows what might happen, but he had to see them hanging next to his normal clothes and mixed with his underwear every day.

Well that's not entirely true, from now on, he was told, he would only be allowed to use his fathers' computer to access the Internet, if he wore his school skirt and knee socks. This was his fathers' idea because Martin had been in the habit of inviting his friends into the house then spending most the night using the PC in the living room. His father guessed that Martin would not want to wear a skirt in front of his friends and locked his computer with a password. He explained to Martin, he would only unlock the PC when Martin was wearing a skirt.




© 2004 by Josie Brian. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.