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."
