Jay was unsure what was with his mom. As they were walking through the aisles, of women's clothing, he started to think. The last time he went clothes shopping with his mom, he couldn't have been past kindergarten. Of course, now he appreciated the thought that his mom would try on some new clothes, and she might even show off a little more. Combine this random shopping trip with his mom's obvious uneasiness with her constantly checking her phone despite it not receiving any notifications, he could only assume something was up with work.
"Hey mom?" Asked Jay. Samantha stopped as she put a variety color pack of panties in the cart, next to some packs of socks and a few bras. Jay was carrying a bag of clothes that they had bought for him earlier so that the cart could hold more clothes for his mom. She told him women love clothes and she would probably need it.
"Yes dear?"
"I don't know if there is something bothering you, but if there is, I hope it works out for you."
"Oh. Thank you dear, I appreciate that."
His words stung Samantha, as he had no idea the gravity of her situation. Still, she really did appreciate that he noticed something was upsetting her, showing the caring side she tried to instill in him. Chris let her know before they left the house, that he was going to be listening through her phone and to stay ready for instructions. After hearing Jay ask about her, he decided to start sending Samantha her tasks.
Samantha jumped at her phone's vibration, despite trying to ready herself for whatever sick game he wanted to play. Reading the first text, she was confused, but quickly turned to Jay.
"What are your favorite colors again honey?"
"Uh, I guess I like purple, red, and uh..." He thought back to the panties he took from his mother that's given him some newfound joy. "Blue."
Another phone buzz, and Samantha went wide-eyed once she looked at her phone. She started to type when it vibrated again. Jay heard her let out a heavy exhale, and watched as she dropped her phone back on top of her purse. They finally moved down away from the underwear section and into the clothing section of the store. A text message flashed on Samantha's phone.
She took a second to read it, then turned to Jay, uneasy.
" Your generation is more in tune with fashion right? How about, if you like what I try on, I'll trust you and get it ok?"
Jay was confused at this proposal. He didn't really know a thing about fashion. He wore whatever was comfortable, be it T-shirts, gym shorts, etc. His mom had even questioned his outfit choices on this trip several times, ranging from the colors of the clothes themselves, to the combinations between hoodies and gym shorts. Besides, he thought, if she put on those revealing clothes for her run under the idea of "trying something new", maybe she would be open to leaving behind her business casual wardrobe. She was currently wearing a nice beige sweater and a nice pair of black pants, something she's worn countless times to her meetings. It'd be nice to see his mom just wear normal clothes. Especially if she shows herself off a little more. As long as he likes it, she'd get it.
Jay agreed, and through the aisles and stands he walked, while Samantha stood by the dressing rooms. While the doors left about a foot of space between the ground and the bottom of the door, she was going to have to put up with it for now. He kept in mind the clothes she usually wore, and at first, he just grabbed a couple sweaters in her size. He liked the brown one, but not the green one he had grabbed. He took the green one before he noticed the green one in a smaller size, deciding to have his mom remodel. She was confused when he returned with the green sweater she said no to, but had to indulge him since Chris was listening on the phone. She pulled it on in the dressing room, noticing it was tighter to put on. She checked herself out in the mirror, seeing the sweater clung to her sides more, and it made her breasts stick out more.
Uncomfortable, but it wasn't her call. As she stepped out, Jay took only a second before he said it's a good fit. "I just wanted to double check," he said. After putting that in the cart, Samantha's phone buzzed. She let Jay know she would wait at the dressing room while he goes and gets clothes for her, and she stepped inside. Jay went to check out tops for her. He grabbed a couple office shirts, with the plan of saying yes to those regardless to satisfy her old style of wardrobe. Then, he would grab tops he actually wanted to see her in. He grabbed a pink button-up blouse, a couple tank tops, and even grabbed a crop top. He realized the last crop top was a size smaller than she wore, but kept it anyways. Hopefully his mother would keep her word.
As he came back to the dressing room, he could hear heavy breaths coming from inside his mother's stall. He held up his hand ready to knock but stopped to listen a little more. What was she doing, Jay thought as the breathing continued. "Surely she isn't masturbating?" His mother was always conducting herself in a professional manner, she wouldn't even have time to masturbate with her workload. But then he remembered that the only man in her life was him.
When was the last time she even went on a date, let alone had a boyfriend? The breathing getting heavier, Jay knocked on the door. He saw her shadow from underneath the door spaz out for a second, as if she was repositioning herself on the bench inside.
"Hey mom, I got a couple shirts and stuff for you to try."
The door opened, Samantha looking bothered about something. She smiled at her son extending out the office shirts for her to try, still trying to catch her breath from the masturbation Chris had made her do when her son stepped away. She could only hope he hadn't heard a thing and knocked as soon as he got back.
"Thank you, Jay."
Samantha closed the door with the office shirts in hand. She was hoping that Jay would inadvertently help her out and just keep her wardrobe virtually the same. The sick fuck could just make her get any clothes he wanted whenever he wanted, she thought, but at the very least it could be delayed. Especially if her son wasn't around when that happened. She put on the first office shirt, a simple black collared shirt with long sleeves. She opened the door for Jay, only to see him on his phone. When she asked how it looked, he only glanced up for one second and said "sure." Well, she thought to herself, maybe this trip will be easy for me after all. She went back inside and took it off. She heard her phone buzz, with the blackmailer telling her to set her phone down at the base of the mirror, giving him a view of the whole changing room. She thought it was weird but had dealt with worse from him. She put on the same style of shirt, this time a tan color. She stepped out once more, with a disinterested confirmation from Jay. She had a feeling he wouldn't be all that interested in shopping with her. What son his age wants to go clothes shopping with their mom? However, she became slightly bothered when Jay handed her the next tops to try on. He gave her a few tank top style shirts, one white, one yellow. The tank tops showed more skin than she would like, as she only had shown more skin in her workout clothes, especially in her new clothes she had to wear. She shut the door and threw on the yellow tank top, actually thinking it looked nice on her. Jay agreed when she showed him and went to put on the white tank top. Once she threw on the white tank top however, she hesitated to open the door.
The white tank top was thin enough that the yellow of her bra could be slightly seen in the light. Knowing she couldn't keep Jay waiting, and definitely not Chris, she opened the door. Jay was caught off guard when he rose his head, and Samantha was certain he could see her bra underneath, hoping he would say no to save her embarrassment.
"I think it looks good on you mom."
"Oh, are you sure? It's not too much?" Samantha said trying to get out of it.
"Mom, you said you wanted to try different things the other day."
The words hit her hard, as that very reason was an excuse to a mess brought by some twisted individual, but set up by her actions. Her son tried to hand her a nice pink blouse, Samantha hoping that her clothes would go back to what she wanted. Before she could grab it, her phone buzzed, and she shut the door. While she was reading her phone, Jay looked at the buttons on the blouse. He still had the sight of his mother's bra through the tank top in his head, and he got an idea. He ripped off a few of the buttons when he was certain no one was looking, and just as he pocketed the buttons, the door opened back up. She apologized for shutting the door on him, and took the blouse out of his hand. She started to shut the door, but hesitated before she left the door slightly cracked open. Jay noticed but decided not to let her know about it. He repositioned outside the door to see if he could get an angle. The crack let him see the mirror, showing his mom's back on the opposite end of the room, right on the other side of the door. Jay also noticed the phone at the base of the mirror, thinking she was just trying to take pictures to see how she looked from a different angle. He held his breath, watching as his mom lifted the tank top over her head and depositing it in the "yes" pile, which were all the clothes so far. He could see the back of her yellow bra and her defined back. He appreciated the passion his mom had for maintaining a good figure, and he was certain other men did too, if they somehow ever saw her. He figured himself lucky. He quickly snapped a picture on his phone of her undress, even though he knew it was wrong and not even that special. Samantha was intoxicating to him, and he hoped he could get more. His mom slid the blouse over top and began to turn around towards the mirror, messing with the buttons, causing Jay to slip away from the door.
After a minute, Samantha spoke from the other side.
"Jay, honey, are there any other blouses where you got this?"
"Sorry, mom, that was it. Why?" Jay replied, thinking back to the full rack of blouses.
"I think its's missing some buttons is all."
