Well this one got pretty out of hand. It's more than double the length that my captions usually are so instead of making the worlds longest picture I have decided to put to rest of the caption down below. Regardless, I hope you enjoy this longer one and let me know what you think in the comments section!

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Aiden had messed up big time. He was hanging out late one night with some friends when one of his friends got the idea to play truth or dare. There were all of the typical truths and dares to begin with, but as the night went on, they started to escalate. The final dare culminated in Aiden having to egg his rich neighbor's house in the dead of night.

Quietly, Aiden snuck out with a carton of eggs he had filched from the fridge in the kitchen. His friends followed behind, wanting to make sure he followed through. Aiden reached the house, hiding himself behind the hedgerows that lined the property. He opened the carton and grabbed a sizable egg from its pouch. He poked his head up over the hedge row and let it fly. It hit the side of the house with a satisfying splash of yolk and egg whites.

Aiden continued throwing eggs. He was nearly out when he shanked one too hard to the left, and it splattered all over his neighbor’s nice new Bentley Continental. The alarm sounded, and Aiden and his friends hightailed it back to their house. Exhausted and a bit nervous, they all went to bed.

In the morning, his friends left and went home. Aiden only got a few moments of peace before there was a knock at the door. He looked through the peephole and saw that it was his rich neighbor. She looked angry and impatient. Knowing what was probably coming, Aiden opened the door.

“Had some fun last night, did we?” she asked in an irritated tone

“What do you mean? I didn't have any fun,” Aiden said, playing dumb.

“My security cameras say otherwise. Your last little egg splattered my car and ruined the paint job. You owe me.”

“Look, I’m sorry miss. It was a dare. Is there anything I can do to make it up to you?”

“Actually, I have something in mind,” she said as a devious grin lit up her face. “I need a new housekeeper and you’ll do nicely”

“Sure, whatever you want.”

The next day, Aiden reported to her house to do whatever cleaning she needed done. Hopefully, it wouldn’t take long. He knocked, and the door swung open like she had been waiting for him.

“What do you need cleaned ma’am?” Aiden asked timidly.

“We’ll get to that, but first you'll need to put on your uniform.”

“Uniform?”

As soon as this question had escaped his lips, she produced a small pile of folded clothes. He took them in his hands and examined them. They were women's clothes!

“Hey, what’s the big idea?”

“All of my housekeepers have worn this uniform, and you will be no exception!” she snapped back, fury welling in her eyes.

“Okay, okay. I’ll put them on.”

Aiden retreated to the half bath located adjacent to the front door and changed into what would become his new clothes for the summer. The outfit consisted of a shiny black two-piece PVC skirt with drawstrings up the sides and a red lacy bra. He got the skirt to fit, but the bra was certainly oversized. Whoever had worn it last must have had giant tits. Aiden stepped out of the half bath to find his neighbor beaming at him with delight.

“It looks wonderful on you Aiden,” she said with a smile.

“It’s a bit big, don’t you think?” mumbled Aiden, trying not to make eye contact.

“Oh nonsense, you’ll grow into it. Here is a list of daily duties. Your living quarters are on the second floor in the east wing.”

“My living quarters?”

“Yes, this is a live-in position, Aiden. You’ll be living here until I can find a replacement.”

Aiden’s jaw nearly hit the floor. This was way more than he had thought he was signing up for. He took the small booklet of duties from his neighbor and glanced through it. This stuff would take ages. He probably wouldn’t be able to complete it unless he lived in any way. His neighbor turned and strode off to go do something, leaving him to his duties.

Aiden got to work right away, hoping to get enough done that some of his days would not have any tasks and he could relax. The oversized bra fabric kept getting in the way while he was trying to scrub the floors, but other than that, it was just basic cleaning work. Finally, the end of the day had come, and he decided to go to sleep for the night. Aiden found his room and began to look through it. The room was nice, but simple. He opened the wardrobe and found 7 exact copies of his current uniform. There was nothing to sleep in, so he opted to just sleep in his uniform instead of sleeping naked.

In the morning, Aiden felt well rested but a bit sore. He had done a lot of work yesterday, but his soreness wasn't in his arms or legs. It felt like his chest and ass were sore. He looked in the mirror and examined his chest. Maybe he was crazy, but it almost looked a tad bit swollen. He didn’t dwell on this thought long though; there was work to be done. The house was huge, and it was going to take all day to get the goal he had set for himself completed. The day went similarly to the day previous, with the only difference being the soreness. The day ended, and once again, Aiden went to bed exhausted.

Aiden woke up the next morning and found that his chest and ass were even more sore than they had been previously. He went over to the mirror to investigate, and to his surprise, he appeared to have boobs! Small ones, but they were definitely there. He poked one with his finger, and it jiggled. A small moan escaped his lips that sounded completely unlike himself. They were so sensitive and, dare he say it, kind of cute. Aiden really did not have time to waste though, and he got to work on his list.

After another exhausting day, Aiden retreated to his bedroom. His newfound tits had made him kind of horny, and he was hoping to jerk off before bed. Aiden undid the skirt and pulled it down. It seemed to get stuck on his ass a bit as he did this but he didn’t think much of it. He laid down on the bed and grabbed his cock that was already stiff. He stroked up and down, and with his other hand, he started to play with his left breast. It felt so nice to massage it and pinch his nipple. It was only 15 seconds before he sprayed cum all over the bed, more from the stimulation of his chest than anything else. Exhausted, he fell asleep.

The next morning, Aiden jumped out of bed and ran to the mirror. Once again, his tits had grown overnight and now looked to be C-cups by his estimation. He also looked down and noticed that his dick looked significantly smaller than usual. He tried to jerk it off a bit to get it hard, but it seemed like it didn't want to. It just hung there limply, measuring all of two inches. Aiden went and grabbed a fresh skirt to put on. He had to undo the straps quite a bit to pull it on. It seemed like his ass was growing as well as his chest. Wasting no more time, Aiden got back to work. Sometimes, throughout the day, he would massage his breasts for fun.

Another day down, Aiden headed back to his room. He was horny again and really wanted to jerk off. He struggled back out of his skirt and laid down on the bed like the night before. However, tonight his dick sat limply between his legs, not wanting to move at all. Undeterred, Aiden began to molest his own tits. He massaged them and tweaked his nipples in a steady rhythm. His cock began to leak precum as he did this. He went at it for another 5 minutes before he finally came. His cum leaked out of his dick with a half-hearted laziness that left a small puddle right under his tiny balls. Sleepy from the hit of dopamine, he fell asleep once more.

When Aiden awoke the next day, he found that he did not have to look in the mirror to see what changes had occurred in the night. He could feel them. His breasts were now easily E-cups, if not larger. Their weight pressed Aiden firmly into the bed. It was quite comfortable and Aiden figured he could easily fall back asleep. But alas, he had work to do. Examining himself in the mirror, he found that his dick had all but vanished in the night. What remained was little more than a slightly enlarged clit above a plump pink vagina. Well, it was official. Aiden was no longer a man and was now a woman. He had fully expected this after the events of the last two days, but there wasn’t much he could do about it. Aiden absentmindedly fingered her new sex and found that it felt much better than her cock ever had. Aiden once again struggled to pull the skirt over his ever-growing ass and got back to work. Her ass wobbled and jiggled with each step, making it very hard to focus while walking, and her tits kept getting in the way of the work she was trying to do. Today would be tough.

Finally, the day came to a close. She had gotten maybe half as much done today as she had the previous days. It was difficult to work in this new body. She even had to stop scrubbing the floor for a few minutes once because the scrubbing motion kept stimulating her tits and bringing her to the verge of cumming. Aiden wasn’t complaining, though. She had grown to like her new body quite a bit, and this job was pretty easy, all things considered. Aiden flopped into bed and began rubbing her pussy. It was one of the best things she had ever felt, and she massaged her massive tits while she did this. Within minutes, she was having an earth-shattering orgasm, but she didn’t stop. She kept fingering away until she had cum at least three more times. Finally, she had reached her limit and passed out.

The next morning, Aiden woke up and found that she was still growing. She couldn’t even guess what letter of the alphabet represented her tits now, and the lacy bra looked like it was a little past its limit. He turned and looked at the nightstand to find that there was a note tied to a silicone dildo with red ribbon. She plucked the note from the dildo and read it.

“I’ve really enjoyed watching you masturbate every night before bed. Here’s a little something to help you xoxo.”

Aiden looked around the room and spotted a security camera mounted in the corner. She had been so caught up with everything that had been happening, she hadn’t even realized she was being watched in her room. The old Aiden probably would have been upset and embarrassed, but Aiden found the idea of her new master watching extremely hot. She was starting to get wet just thinking about it, and she instinctively grabbed one of her massive tits. Now was no time to masturbate though. If she didn’t complete her tasks, master would be upset and might even take away her new toy. She would have to wait until later to take it for a test ride. Aiden went down to one of the many living areas and sighed, putting her hands on her hips. Aiden knew she should get to cleaning but all she could think about was if somebody would bend her over the couch and fuck her.