As Anne Golith looked at through her dresser drawers in her childhood bedroom and something immediately felt off, but she could not initially place it. She hadn't been in the dresser for over five years, but somehow everything in the dresser felt like it had been touched and rearranged recently. As she pulled out a layer of skirts and saw a very revealing thong she hadn't worn since she was still in college in her early twenties and back at mom and dad's on the weekend it clicked. Someone had been through the drawers. Everything felt off because it was off. Skirts and blouses weren't folded in the right manner, one of the skirts was one she was confident she would have hung up. The hidden underwear also tipped off the likely culprit. Her nephew Jack.
Anne's mind recalled a conversation she had with her sister Sally two years prior. Sally had noticed that she had a few less pairs of underwear and a couple of skirts that were too small for her were no longer in her closet. Like their parents Sally was never one to give away any clothes "just in case". Sally didn't think much of it, but allowed the fact to just nestle in the back of her mind. A few weeks after she noticed them missing she was putting clothes away in her teenage son's room and as mothers are wont to do she snooped a bit. In a bin under his bed she found her missing clothes, and some other personal items that a person might use to enjoy themselves. Sally left it all where it was, but also had to confide in someone, and so she naturally chose her little sister.
Anne was only thirty five, and Jack was now twenty. Jack and Sally lived about three hours from Anne and Sally's parents. But once a month Jack and Sally came up for a Friday into Saturday visit with the family. For years now Jack had slept in Anne's old bedroom, and apparently had made use of some of her old things. Anne went digging further, into her closet, into her old makeup cabinet, and found that Jack had used a lot of her things. Most of her dresses were hung crookedly, her underwear drawer had clearly been rifled through frequently. In the makeup cupboard were two new dark red lipsticks that could not have been more than a few months old.
Anne sat down on her old bed and worked through emotions. First she was just plain angry. The clothes were her things. She didn't know what Jack did with them, but there was no way it was no overtly perverse. Then she was amused. Jack was a fit, and affable guy. He was a track star and had a long thing body. He was at least five inches taller than Anne but in all reality his weight now and her weight fifteen years prior were about the same. She hadn't worn the clothes in forever, who did it really hurt if Jack liked to dress up like she had. Then Anne got curious. What exactly did he do? How did he look in her clothing.
Anne knew that this weekend was a visit weekend. So she decided to let some kind of curiosity out. Anne had a camera that she used to use in her backyard at night when she was trying to figure out which neighborhood kids were causing mischief in her shed. It would run for sixteen hours at a time before the battery needed to be changed or the memory card was full. It was small and easy enough to hide, and while it was not the best footage or audio it was good enough. She made sure she was visiting when Jack and Sally came. She made sure to sneak off to her bedroom before dinner to hide it and turn it on. Then she waited. Sunday could not come fast enough.
Friday and Saturday passed painfully slow for Anne. She enjoyed her time with her family as always, her Dad's delicious ribs for Friday supper, card games late into the night (where Anne noticed Jack excused himself early to bed), and all the joys that typically come with family time. But in the back of her mind curiosity was racing. Anne wanted to go pull her video. She wanted to see what the fuck was going on. She wasn't fully aware of it at that moment but Anne had started to feel a certain level of sexual excitement about it all. The taboo nature of her nephew and whatever he was doing, the naughty act of secretly filming someone else, all of it was slowly and subconsciously starting to turn gears in her mind.
The tape was way more than Anne ever would have expected it to be. Anne kind of just assumed her nephew would dress up in girls clothing and jerk off on the bed. Maybe he would use a pair of panties to aid himself along, she knew of guys who did that. What she actually saw was far more depraved than she could have ever predicted.
Once in the room Jack immediately stuffed a pillow by the door. He then stripped down to nothing. Anne was shocked by the fact that Jack had absolutely no body hair of any kind, he had clearly shaved himself recently. She also was shocked by the size of her nephew's dick. It was at least eight inches, and while not impressively thick it was still more than she imagined her string bean nephew to have. He went straight to the dresser and pulled out several skirts, panties, bras, and blouses.
"So Jackie, are you a slut tonight or demure?" He asked himself in a voice clearly designed to be more feminine
Jack ran his fingers over a black bra and panty set. She didn't hear what he said, but based on the outfit choice he clearly had gone for slut. The skirt was one of Anne's shorter ones, and on her taller nephew it left virtually nothing to the imagination. The blouse he picked was one of her favorites because it highlighted her C cup breasts and made them seem just a little big. Jack put two foam balls down his shirt to look like a full and rounded out woman.
Then Jack slipped into a pair of Anne's high heeled shoes and gracefully, really gracefully, walked to the mirror and put on the dark red lipstick Anne had seen. He kissed himself on the mirror.
As the kiss ended Anne heard him say "I love being a slut for my aunty"
Anne's jaw dropped. She skipped ten seconds back five separate times each time being convinced she would hear him say something other than "aunty". The sixth time she heard him say Aunty she let the tape roll on. She also became acutely aware that she was getting wet watching this.
Jack went on. He asked his aunty if he could worship her toes. He begged and pleaded to, and then simulated doing so. It was a this moment that he started touching himself for the first time. Not hard, just little soft grazes of his noticeably erect cock through the skirt and panties.
Anne didn't fully process it in that moment but on of her fingers had drifted below her own skirt. She was lightly tracing her clit through her own panties. Slowly the juices started to soak them, but it would take the next scene of Jack's perversion before Anne realized what she was doing and how much she liked it.
"Aunty can you fuck me please? Please I'll do anything." Came Jack's begging on the video.
"Yes really anything Aunty." Jack said again
Anne wished she knew what exactly the fake version of her was telling him to do. She was enthralled by the scene now, one finger had slipped underneath her panties and was now teasing the entrance to her slit.
"Yes Aunty of course I'll eat my mommy's sexy pussy if you'll fuck me please, please mommy let me pleasure you while your sister fucks your good little slutty girl."
As the last words left his mouth Jack flipped himself onto all force and inserted the back end of what looked like a hairbrush into his ass. In front of him was a pillow that Jack simulated giving oral sex to while pumping his arm back and forth. Occasionally his other hand would reach behind and slap his ass while he moaned out.
"Yes Aunty I love your fucking cock" Jack moaned "and I love the taste of my mommy's sweet pussy thank you Aunty."
Anne had now buried two fingers into herself. She was very aware of it. She was loving what she was watching. She loved watching her nephew fucking himself. She loved the scene he was creating. In that moment while pleasure was building she couldn't feel any shame about it. She just wanted to be fucking him. She looked at her hand and wondered how it would feel to bring it down onto his ass.
She rewound the scene just a bit. She wanted to ask Jack the question he was answering. So she went back to before his last answer.
"Do you like my big fucking cock Jackie? Do you like me fucking you while you pleasure your mommy?"
Jack responded on the tape "Yes Aunty I love your fucking cock" Jack moaned "and I love the taste of my mommy's sweet pussy thank you Aunty."
She repeated this twice feeling herself getting closer to the edge of a strong orgasm. Jack clearly was too. Anne watched his back arc and the next begging came.
"Aunty can I touch my little girl cock? Please Aunty please I want to rub my cock please!"
"Oh yes I would prefer your hand aunty please let me. Oh god yes yes yes Aunty please yes I love your perfect fucking hands rubbing my little girl cock."
