Ben and his older sister’s control

The sun gleamed over an ocean blue swimming pool with boys and girls enjoying their casual summer days, relatives to be specific in a family gathering at one of Ben’s uncle’s mansion.

Ben is relatively shy and doesn’t speak much, and especially shy with girls.

At 18, 5 foot 8, dirty blond hair and no confidence he sits in his older sister’s temporary bedroom, Sophia, whose bedroom is used as a changing room for all, now Ben reminding himself of all his insecurities and coping that he is alright before building any courage to go out to the pool with his cousins and all.

He could hear the laughing of his uncles and aunts having their usual boring talks, and at this point Ben was considering he just doesn’t leave the room at all, now he has to think of an excuse.

The boy looks around the room and sees all the bags of everyone who has changed on the floor, and as curiosity builds up he “checks” what his cousins’ bags contain. Nothing much but a few extra shirts and a bunch of water guns that the other boys seem to have forgotten to bring out.

Now for the fun part was investigating his female cousins’ bags, the sight of them is already blinding with all the glitter and accessories that they have. But what caught his eye was his sister’s white and mysterious bag. Ben never really expected much but pushed himself to open it up.

Ben takes hold of the silver zipper and slowly slides the bag open remembering how his sister would bully him and how much worse it would get if she suspected him of getting close to her belongings.

“A bunch of makeup…a phone charger…and something hard?” Ben mumbled as his hand grasped something hard concealed underneath rags of clothing. Before digging in Ben decides to lock the bedroom door in case of any intruders. So he gets up and jogs to the door, checks if anyone is around then closes and locks it.

Ben glances back at the bag and quickly sits infront of it and plunges his hand through the piles of fabric and getting a grasp of the rigid object,

“Gotcha…wait there is two…hold up.” The boy says as he fishes out the first object.

“Oh…it’s a pair of wedges, Sophia really likes this pair but I wonder why she isn’t wearing them outside.” He questions. He now knows that the second object is probably the other pair.

Ben manages to pull out the other pair without messing up the bag’s insides too much, “How does she even walk in these things? They aren’t too high but still..” Ben thinks to himself.

The pair of feminine footwear is roughly 4 inches with black strapping ready to go all around the ankle and a little higher. And although Ben didn’t really care about them so much at first but the more he though of the pair the more he started to wonder how they would feel on his feet. Him and his sister have the same size of shoes, because Ben has small feet and is sometimes ridiculed by his sister for it.

“Little bro you might as well wear my cloth or something you small f*ck LOL, grow up and be a manly man would you?” His sister would mock him and it infuriates Ben to be downgraded like that.

“Well then I w-will d-do it! Fine!” Ben trips in his own words and decides to put on the pair of shoes. He picks them up and walks over to Sophia’s bed and sits on it, he hesitantly lifted his bare foot and slowly slid it into his sister’s prized shoes. Now to fixing the straps and tying a nice bow at the end of it to finish up the first pair. Now he picks up the second pair and reconsiders doing so, if he was to be caught or close to it the shoes wouldn’t come off quickly because of all the ribbons, but he decided to go with his fetishes’ desires and puts on the second pair and gently fiddling with the ribbons and fixing them in place.

Now Ben has calmed down from his small fit of rage he comes to his senses and looks at his feet now in his sister’s wedges. He blushed and was so embarrassed at what he had done, but to be fair he didn’t think he looked too bad,

“Nice…looks bad when I look at myself in my swimming shorts…I wonder if..” He whispers to himself as he plans to raid the white bag again for something else.

Ben gets up and tries to run for the bag but stumbles down to the ground. Ben now remember that he had a footwear that was exotic for his liking. But her continued to crawl over to the bag and he dug through it. He picked up anything he could find as there was too many pieces inside. The attire appeared to be a black open shoulder top and a white mini skirt with a black heart on the side.

“Quite the outfit huh?” Ben spoke to himself.

The boy picked up the two pieces and tried to stand up in the wedges, struggling he manages to pose straight up and to his surprise the shoes helped straighten his back making him feel a little taller, plus the height of the pair themselves. Ben walked pretty well in them towards his sister’s full length mirror. He sat down at a comfy chair first then pulled off his swimming shorts, now butt naked Ben takes holds of the white skirt, caressing his fingers over the soft fabric, he pulled the skirt down and lifted his feet up to make way for the skirt.

Pulling up the skirt Ben slowly stands up to fix it in place, it felt very weird for him but wanted to experience it now, experience being a girl.

The boy then picked up the top and quickly put it on, slides his hairless arms through the side opening of the top. The feeling of his shoulders’ exposed likes this is new and thrilling.

Ben looked at himself in the mirror not knowing wether to enjoy or to be ashamed of himself. He is already to deep in the rabbit hole so might as well go further down. He cat walked his way to the bag again and clawed out his sister’s makeup kit. The boy didn’t really care about anything in the box but the lipstick tubes. He chose the soft red one and took off the casing. The stick of coloring popped out of the tube and was ready for use, so Ben utilizing the mirror slowly painted his lips bright red. And to his surprise he did very well.

His lips puffed out like a girl’s would, Ben smiled at his reflection, but he couldn’t exactly recognize himself, he only saw a pretty girl.

Everything was quiet…too quiet and too good to be true. Ben thought of that but chose to ignore his mind and just enjoy the moment. He was too into it he couldn’t feel his dress attire twitch…