Captioned Images Series: Trapped

Created: 06/03/2023

Alone in the house, his head propped up by pillows laying on his back, Jackson stared at the screen of his iPhone. There were various sounds of crashes, various pops, and music emanating from the game. Jackson didn't care about the score. He simply enjoyed playing.

No game lasted forever, inevitably the video game concluded. He had scored higher at another time. He had also scored lower. It really didn't matter; he was just wasting time.

He put the phone down beside him on his bed and forced himself into a sitting position with his legs hanging off his bed. He stood up, noticing the outline of his body on the comforter before turning to the door and exiting his room. He walked down the hall and entered his sister's room. She wasn't there of course, except for himself, the house was empty.

The decor of Jamie's room was off-white with peach highlights. Jamie's full-sized bed had a round headboard in an intricate pattern and is covered with a peach-colored print comforter, yellow print duvet, and stacked pillows including a heart-shaped throw pillow. To the bed's left was a circular night table that looked like an upside-down waste basket. On top of the night table, were a yellow lamp, a ceramic cactus, and a colorful corked jug. Small pictures of flowers and abstract art hung on the walls. The wall-to-wall carpet was in a neutral gray. There was also an area rug in front of the night table, parallel to the bed.

Jackson ignored the bed, he headed to the wall opposite the window in which stood a bureau of drawers in the off-white color. The drawers were over three feet across and four and a half feet high. On top of the bureau were pictures that were dear to Jamie as well as other knick-knacks.

Jackson bent down and opened the bottom drawer. Inside was Jamie's lingerie. Jackson had never opened this drawer before. He had never wanted to. But today, he did so. Jackson looked over the scores of panties and other feminine finery which belonged to his sister. Seeing them excited him. He didn't know why they should excite him on this day when they hadn't any other day. He didn't care.

"I shouldn't be doing this," Jackson whispered to himself. He ignored his own words as he looked over the lingerie.

He decided to pull the drawer out farther so he could look at more of his sister's intimate apparel. All the underwear in his room was all white. Jamie had panties in dozens of colors and patterns although most were either white or black. Jackson reached into the drawer and picked out a pair of panties at random. He made sure to remember where the pantie had been so he could return it seemingly undisturbed later. The garment felt very soft in his hand.

He brought the pantie to his face and rubbed it on his cheek with his open hand. The pantie felt even softer against his cheek than it did against his hand.

"I shouldn't be doing this," he told himself again. He didn't stop.

On the other side of the drawer were the bras. He selected one. The bra didn't feel as soft as the pantie. It felt a bit stiff to him in comparison due to the molded cups. Jackson wasn't concerned if the bra matched the pantie. He didn't care what they looked like. He wasn't thinking at all. He was mostly moving on autopilot.

Once selected, he put both the bra and pantie into one hand and then closed the bottom drawer. He opened the above drawer and saw a drawer filled with pajamas, nightgowns, socks, knee-high stockings, and pantyhose. From this drawer, he selected a pair of flesh-colored pantyhose. Those were the ones he found most appealing. With lingerie in hand, he moved to the bed. He put them down on the bed and then pulled his own shirt off. He wasn't wearing shoes, so next, he unbuttoned his jeans, unzipped its fly, and pulled it down to his knees. He had to sit on the bed to remove his jeans. Next to be removed were his white athletic socks and then he stood up again to take off his male briefs. He was completely naked in his sister's room. This had never happened before in his life.

He reached for the panties. He stepped into the panties with his left leg first. He pulled them to his knee, and then balancing on one leg, he stepped into them with his right leg. He pulled them up to his thighs, then over his penis, and placed them on his hips. They were high-cut briefs. The fabric hugged his penis in a semi-V-shape. His cock had been hard for over four minutes without him noticing.

The bra was next. Jackson put his hands through the arm straps. Then he used his hands to put the straps over his left shoulder, then the right. He tried to reach behind him to fasten the clasps. It was harder than he thought. He pulled the back band down to the small of his back. He wasn't concerned about stretching it out. After a few seconds, he got one hook into one of the eyes of the closure. But he was sure it was the wrong one. He had to unfasten it and try again.

"How do girls do this!" he mumbled.

It took about a minute of fumbling around before he got the bottom hook correctly hooked. Once the first hook was in the proper eye, the second was easy. The back snapped into place. But the cups were too high on his chest. He yanked down the front of the bra until it seemed to fix correctly. He looked and saw his empty cups. Walking back to the drawer, Jackson decided what he needed to fill his bra cups with. Pantyhose was his choice since they were bigger, but it only seemed right to fill the cups with panties. He placed two pairs of panties into each side of his bra to fill the cups out.

Back to the bed again, Jackson sat down to put on his pantyhose. He started with his left foot again. He pointed his toe and snaked it down the leg of the hose. He pulled on the right side and then the left until his toe hit the seam. The seam wasn't aligned with his toes, so he twisted it to the right until the seam was in the right place. He did the same thing with the left foot. The hose was three-quarters the way to his knee. He pulled it up past his knee and then stood up to get it to his hips. He finally stretched it as high as he would go to his waist as he stood up.

"What am I doing? What am I doing!" He pleaded with himself, but he wasn't going to stop.

Jackson opened the closet. He wanted to wear a dress. He didn't have any interest in a skirt and blouse. He definitely didn't want to wear a pair of jeans. He wasn't sure if his sister's jeans would fit him regardless.

As with the lingerie, Jackson didn't have a specific dress in mind to wear. He hadn't planned on anyone seeing him dressed like this. The dress he wanted (for no particular reason) had to be no longer than knee-length and have some sort of sleeve. He looked down the line of dresses. He started at the far end of the closet and headed toward the middle. He looked at each dress for a second before moving to the next. Finally, he selected a puff-sleeve sequin plunge pull-on dress. He didn't select it because it was a pull-on or had a plunging neck. The dress simply appealed to him. He took it hanger and all from the closet. He held it up in front of himself and then twisted his fingers so he could see the back of the dress. The dress was high in the back and had an elastic waist. It was in a fit-and-flare silhouette, not that he knew or cared.

He pulled the dress over his head and let it fall into place. The bra front of the bra could be seen in the gap that was the plunging neckline. It clearly wasn't the right bra for this type of dress.

Jackson walked over to the closet again in search for another dress. He didn't know what type of bra went with this dress. Jamie wouldn't wear a bra with this dress. But Jackson preferred to wear a bra.

Jackson didn't hear his sister enter the house. It wasn't until she got closer to her room that he heard her footsteps. He looked out the door and saw her heading to her room.

Instinctively, Jackson closed the door.

"Hey what are you doing in there?" Jamie yelled. She ran to her door and tried to open it. Jackson held the door shut not letting her in.

He was completely dressed in her apparel. His own clothes were scattered on the floor of her room. There wasn't a lock on the door to keep her out. There wasn't anywhere he could run, nor could he take off her clothes in the split second it would take her to open her door when he released it.

HE WAS TRAPPED.

End