Tuesday, May 19, 2026

Sissy Shopping Nightmare - Part 2 of 4

 

Sissy Shopping Nightmare

By Karen Singer

 

Part 2 of 4

 

Not knowing what else to do, Bruce wandered slowly toward the center of the mall.  Two minutes later, another message came in on his phone  A message with another picture.  He didn’t need the message to tell him what he needed to do.  That much was already obvious.  In fact, it had been obvious from the moment he had started looking for the socks.  The picture that came into his phone was a picture of a pair of shoes.  Black shiny shoes with a rounded toe and two straps that went across.  Shoes that looked like they would be perfect for a little girl, even though he already knew they would have to fit him.  Which meant that even though the shoes looked like they would be for a little girl, the shoes he had to find would actually be adult women’s shoes.  The short message said:  This EXACT pair.  Not something that looks like them.  We’ll know the difference.

 

Christie & Jill Lil Dahlia Toddler Girls Round Closed Toe Mary Jane Shoes | Black | Toddlers 8 | Shoes Mary Jane Shoes | Easter Fashion

 

The exact pair.  That didn’t sound good.  He realized immediately that he needed a shoe store.  But wait, didn’t the department stores sell shoes too?  Once again he turned around and headed back into the department store he had just left.

No, no, no!  Why did finding everything have to be so damn difficult?  He had checked each of the four major department stores attached to the mall and hadn’t found what he was looking for.  Oh, he found a lot of shoes that were similar, but not that exact pair.  They always had either a higher heel or the toe was pointed, or they only had one strap instead of two, or they weren’t shiny in the least.  And as a man looking so carefully through all of the women’s shoes, it had been a somewhat embarrassing task…let alone a man carrying a little girl purse in his hands.  So that left him now searching for the shoe stores in the mall that weren’t the big department stores.  No, they couldn’t make this easy for him at all, could they.  He went into two different shoe stores before he finally found the shoes he needed.

Once he found them though, he was faced with a new problem.  They were going to make him wear the stupid things.  The moment he stepped out into the concourse with the shoes in a bag, his phone dinged again and he read the message.  Yup.  No surprise.  Hating himself, hating the people forcing him to do this more than ever, he sat on a bench and removed his shoes.  He stuck the left little girl style shoe onto his foot and buckled it…to the scrutiny of all the people walking by, who also saw what kind of socks he was wearing.  The people who watched him buckling the right shoe onto his foot seemed to be watching even closer.    When he stood up and looked down, he could no longer see the embarrassing frills on his socks anymore, but the white socks stood out in stark contrast to the shiny black of his shoes, seeming to make them more obvious than they already were.

Knowing for certain that he was being watched closely, as per his instructions, his male shoes went into the trash along with the bags and the box from the shoes.  He felt like more of a fool than ever with his little girl purse, and now little girl shoes and socks on his feet.  What would be next?  He was afraid to find out, even though he was sure that whatever they wanted next, it would be something else that looked like it might belong to a little girl.

Stupid.  It was all stupid.  And very, very embarrassing.  Why were they making him do this?  It made no sense at all!

The moment his hands were empty the next message came in.  This one was far different from the previous messages.  Yes, there was a picture.  An embarrassing picture, but this message actually specified what store he needed to go to, and what to do once he got there.  The message read:  Go to Fine Feminine Foundations.  Ask for Claire.  She’ll tell you what to do.  The picture of course, was of a bra.

 

Sculptresse by Panache Dream UW Full Cup Bra Rose Pink | Lumingerie ...

 

He was sure he had passed the store somewhere, but he didn’t remember where.  He walked around until he found a mall directory.  There.  Shit!  It was practically on the other side of the mall.  Turning his steps in that direction, and hating what was in store for him, he hurried as quickly as he could to the specified women’s lingerie store.  Going inside, he noticed a few women in the shop.  He found the cash register and asked for Claire.  The woman he asked seemed to look him over carefully with a rather distasteful look on her face.  “Just a minute,” she finally told him.  A few moments later, a woman approached him.

“So you’re the monster,” she said as she walked up to him and stared him in the face.

“Monster?  What are you talking about?”

“You!”

“What did I do?”

“As if you don’t know.  You…and your damn son.  You both should be hung.”

“What?  What did I do?” he demanded.

“Shit!” she replied.  “Come along.”  She turned and walked away.

“What did I do?  I don’t know!” Bruce argued.  He got no answer from the woman at all.

She led him into a tiny room and had him remove his shirt.  In moments, she was measuring his chest.  No matter how much he tried to get her to tell him anything at all, the woman remained silent.  She left him in the room, then came back a few minutes later and fastened a pink frilly woman’s bra around his chest.  She carefully tightened all the straps.  Bruce noticed that even though the inside of the bra cups were empty, they were still stiff enough to stand out from his chest.  At least they didn’t appear to be large.  In fact, they were surprisingly small.

The woman had him put his shirt on.  Buttoning it up was weird with the breasts now underneath.  In fact, he was lucky he could button it over top of the new breasts he appeared to have.

As soon as he was dressed, she led him out to the cash register where he again had to reach into his little girl cat purse and pull his wallet out.  Two minutes later, he was back out in the mall concourse, this time with the little girl cat purse in his hand, shiny little girl shoes on his feet with frilly white socks, and now his chest looked like he had breasts under his shirt.

How much more of this stupidity were they going to pile on him?

Just a few seconds out of the store, his phone dinged again.  He’d really like to take the thing and break it.  Instead, he checked the message.  Shit!  Shit!  Shit!  The message said:  Find it and buy one in size 12.  Better hurry.  You’re falling behind.  Would you like a video of us hurting Jimmy to get you moving faster? 

Girls Dress Pink Flower Wedding White Princess Unique Bow – Sunny Fashion

 

The picture was of a white dress with pink flowers on it.  He was sure it was made for a woman, but it still looked like something a little girl might wear.  But his bigger problem was that if he didn’t hurry, they would hurt Jimmy again.  He began to run.  Where should he look first?  There.  A women’s clothing store.

Running with a purse in his hand was strange.  Especially that purse.  Running made more people notice him.  But still, he couldn’t let them hurt his son.  They had already done enough to him.

So…many…women’s clothes!  So many dresses!  There were thousands of them.  How was he supposed to find the right one?  It was impossible!  Purse in hand, he literally ran from store to store, searching desperately, and very much afraid that in his haste he had missed it.  What would he do then?  What would they do to Jimmy?  Hurt him?  Or kill him?  Either…or both.

Desperate, he ran into another of the big department stores, and right into the women’s section.  His eyes fell on a mannequin.  It was wearing the same exact dress.  Finally!  He found a rack of them and easily found one that said size twelve on the label.  He pulled it out and rushed with it to the checkout.

His rushing caught the attention of too many people, but it couldn’t be helped.  The checkout woman said nothing, but she certainly gave him a lot of strange looks as he paid for the dress.  As soon as possible, he was hurrying as fast as he could out to the concourse again.  It had taken him forever to find that dress.  Had they hurt his son again?  He could only pray that they hadn’t.

The phone dinged the moment he left the store, more proof that he was being watched.  He briefly looked around but couldn’t tell who it might be.  There were literally too many people looking at him.

He checked the new message on his phone.  No picture this time, just words:  Take your pretty new dress to the men’s room by the food court and put it on.  DON’T pee in there.  Someone is already there waiting to watch to make sure you don’t.  More when you get out.

Ugh!  He had been afraid they were going to make him wear the stupid thing.  Now he had proof.  The men’s room by the food court.  Where the heck was that again?  He had only passed it at least six times today already.  Was there a men’s room there?  And he couldn’t even pee when he got there because someone would be watching while he was in there?  Did they want to watch him putting the dress on too?  Although if he did put the dress on, whoever it was wouldn’t be able to miss it if they tried since he would have to walk out of there too.

Growing tired from all his rushing around, he hurried toward the food court.  The men’s room was easy to find.  It was also somewhat crowded since it was lunchtime already.  Having to search to find everything had taken him hours.

Really not wanting to do it, he went into one of the stalls.  He leaned back against the wall of the stall for just a moment to breathe a bit.  This was so hard, and it was getting worse.  But Jimmy.  He was doing all of this just for Jimmy.  What had Jimmy done that was so bad?  What had Jimmy done that his son hadn’t told him about?  Whatever it had been, it must have been awfully bad.  His son?  His Jimmy?  He still found it hard to believe.  He also found it hard to believe that he was actually going to put the dress on and wear it, not only out of the stall he was in, but all over the stupid friggin mall!

Before removing his clothes, he glanced down at the toilet.  Yeah, he could pee.  In fact, the more he looked at the toilet the more he felt like he needed to pee.  But the instructions…and someone was out there close enough to hear him if he did.  Sighing and wanting to punch someone from the frustration of it all, he began removing his pants.  His shirt went next.  He pulled the dress from the bag and pulled hard on the tags to break the plastic holding them to the dress.

He unzipped the back of it and stepped into it.  He pulled it up his body.  He realized the dress had two layers.  A thick white inner layer that couldn’t be seen through, and a white gauzy outer layer that was semi-transparent.  The outer layer was decorated with pink roses and green leaves.  The dress had no sleeves at all, just two semi-wide straps that went over his shoulders.  The waist of the thing seemed to come right up underneath the bra he was wearing, although the dress itself completely hid the bra, but not the bumps the bra created.  The waist had a pink and green band that went all the way around and ended in a big bow just off center under his “breasts.”  From just below the waistband, the skirt of the dress flared way out until it ended…far shorter than he thought it should.

He reached behind him to zip the thing up.  Just reaching the zipper was difficult.  He had to fight and stretch hard to pull that zipper up as high as it would go.  The dress began to squeeze his entire chest tightly.  Very tightly.  The darn thing was too small.  Why had they specified that it had to be a size twelve?  With one final effort, the zipper was up as far as it would go.  It was on.

His hands went down to his sides, and he realized he could easily grab the bottom hem of the dress with his hands.  It was that short!  Damn!  He hoped the stupid thing would at least cover his underwear.  He pressed in on the skirt.  Yeah.  It looked like it would, but not by much.

Now what?  He realized he had no choice but to leave the safe confines of the stall.  He put his pants and shirt into the bag that had held the dress.  He grabbed his little girl cat purse.  And he opened the stall door.  He did his best not to look at anyone as he walked purposefully out of the bathroom and into the crowded food court.  Yeah.  People were turning to look at him everywhere.  How could they not?

Halfway across the food court, the darn phone dinged again.  He read the message, and wasn’t surprised:  Very pretty, from top to bottom.  I hope you’re enjoying yourself.  Throw your pants and shirt into a trash can.  Make sure to throw them separately along with any bags you’re still carrying.  One of our watchers has been instructed to make sure you put your pants and your shirt into the trash.  You’re wearing a pretty dress now.  What would you need pants and a shirt for?

Bruce really wanted to hit someone…or cry.

 

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