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Aunt Samantha learns not to lose in this game anymore.

She'd mused for a while on the best way to attempt this and decided it was best to lie on her back. The first toy picked up was the plug; it was slimmer at the tip and flared out to the width of a couple of fingers. A little lube was smeared over the plug and then on the tip of her finger which she rubbed around her tight rear hole before placing the tip of the plug there. A deep breath was drawn in, eyes closed, and a thought of now or never and she pushed, gasping a little as she felt a bit of stretching and accommodating about two inches of the plug in. Kat paused, calming herself as she adjusted to the peculiar feeling registering in her brain. It wasn't all unenjoyable, it was just weird and so once the feeling subsided a bit she pushed another inch in which brought the first twinge of pain. Just a light feeling and not unexpected nor enough to slow her down now, being so close to the end she pushed the remaining inch and a half in, groaning at the stretching of her rear. Fingers were pressed at the base of the plug to keep it within her.

A smile crossed her lips; she had taken the plug in and allowed a little giggle at the dirtiness of it all. That was about the first time that she realized her wrist felt wet, it had been resting against her pussy and she had become rather soaked. Her hand drifted over and caressed her clit, body jumping at the feeling. It was about then she realized it had been quite some time since her last orgasm and proceeded to rub her clit with her fingers. It somewhat surprisingly didn't take long till her body was racked with orgasm. As Kat lay panting on the bed she felt a slight ache from having them plug in her rear, very worth it in her mind. Perhaps this anal thing wasn't so bad she thought.

Over the next couple of weeks she played with the toys as often as she could, excusing to herself that she was just getting used to the idea but truthfully she had come to relish her time alone with them. The first few days she had to tell Jack that she had slid on the stairs and that's why she was walking funny. Soon enough she found herself on the toy stores site again, this time looking for toys that were closer to Jack's size and once those had been added to the cart curiosity caused her to click on the vibrators tab. She saw a hard plastic one that was a few inches long and glowed purple and added it to the cart. This time she giggled in anticipation of them arriving and counted down the days. She'd noted other benefits to this already, a major one being more adult time spent with Jack. He had commented several times that he didn't know what had come over her and certainly wasn't complaining.

As Valentine's Day approached Kat was becoming more and more comfortable taking the toys in her ass, having taken up doing household chores with one of the plugs in place. It just gave her a feeling of being naughty while walking all over her home and sometimes greeting her neighbors when she needed to venture outside. Once even she had it in while shoveling snow, that was an interesting experience as the physical labor made it hard to keep the plug in place. She found herself on a clothing website, clicking through various forms of lingerie and debating back and forth carefully over what would be just perfect for that night. She finally settled on one and a few accessories for it and wiggled in her chair in excitement.

The big day approached at a rapid pace and that morning she sprang out of bed giddy as could be.

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