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Sissy Roomate (Private with Cute Little Kokiri Girl)


Lavellan

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Rachel unlocked the door to the apartment she shared with her long time friend. It had been a long day, but she was finally on a break for a little while and looked forward to relaxing. Walking quietly to her room, she set her stuff down and laid down on her bed looking up take out menus. Seeing there was nothing of interest, she decided to cook instead.

 

Rachel was what most people would call a pretty girl. Not really a blonde hair blue eyed barbie, however. Instead she had shoulder length curly brown hair with hazel eyes to match. She was tall, even taller than her roomate by a few inches and she had taken up sports in high school. Volleyball being her favorite. While she was pretty, she never really dated much. The boy's in school were just too hypermasculine. Always wanting to be the alpha male in a building with hundreds of people. It was annoying.

 

But her roomate wasn't like them. It was partially why she had decided to get an apartment with him. He was small, pretty nerdy looking to be honest. And it was strongly rumored that he was gay in high school. Rachel didn't like to assume, but she could see how that was the case. Her roomate could easily pass as a twink in most circles. But she never asked him for details on his sexuality.

 

Standing up from her bed, she called out to him. He was most likely in his room and she walked to his door. "I'm coming in!" She announced suddenly.

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Elliott smiled as he looked in the mirror in his room at the dress he was wearing, it was one Rachel had worn, a pink one she had to wear at her wedding, she hated it but he had loved it. Elliott was shot man with blonde hire and blue eyes and boyish/girlish feachers, something that got him bully a lot in school.

He was sweet and kind hearted, but all timid and a big of a scaredy cat. He all very smart being very good fixing all kinds of pc's and the like, so he did need to go out  for work. He and Rachel had been friends ever since they were in diapers, she had all ways be the brave one keeping most of the bully's away.

So it was nice to get a place together. Ever since Elliott tried on that pink girly dress Rachel had, something just felt right, he even got old school bloomers on amazon too. He did not hear Rachel come home as he was listening to dancing queen on his head phones dancing with a stuffed unicorn had got one day. He was so into the song he did not even see Rachel come in.

 

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Rachel barged in expecting to just see Elliott on his computer or reading a book or something, but was shocked to see none of that. Instead she saw her best friend in her dress (one that sat in her closet so long she didn't even notice when it went missing)! Not only that, but she could see the ruffly bloomers underneath everytime the dress swayed up. That paired with the soft looking unicorn painted the whole picture for her. 

She wasn't quite sure what it was, but something inside her felt like an awakening. A realization. This...was cute. One of the cutest things she had ever seen in fact. Elliott was always shy and timid. But here he wasn't. He looked happy and carefree. Her chest warmed as she leaned against the doorway and watched her friend dance happily like a little girl. And that made her happy too. 

"Elliott." She said softly as she walked over and tapped him on his shoulder. 

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When Elliott was dancing a feeling of needing to pee hit him, but just as he was about to stop, when someone tapped him shoulder. Elliott let out a sharp eep as he turned around and their looking right at him was Rachel.

"RACHEL." Elliott yelled stumbling backwards and falling on his butt. Elliott pulled off his head phones looking at her. "I-I-I C-C-CAN I-I WHAT ARE Y-YOU I-I." Elliott tried to say as hew felt his heart racing as he cursed himself for not locking his door.  

"RACHEL. I-I C-CAN E-EXPLAIN Y-YOU SEE I AHHHHHHHHHHHHH." As Elliott was trying to explain himself when all was a sudden he started to wet himself. "NO NO NO NO I-I-I-I WAAAAAAAAAAAAAAA." Elliott soon started to cry like a baby as warm pee socked his ruffly bloomers, Rachel's dress and the bed room floor.

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Rachel was surprised as her friend jerked back and fell. She felt bad seeing the panic on Elliott's face seeing as how she was the one who interrupted his privacy. Sure, he wore her dress, but it wasn't like he was ruining it. It even looked cuter on him. "Hey, Elliott it's okay-" 

She was stopped as her friend began wet himself. Soaking through the ruffly panties, into the dress, and dripping to the floor. "Oh Eli..." She cooed gently as he started to cry. Crouching down next to him, away from the wet pool, Rachel wrapped him in a hug and pulled him to her chest. "It's okay. Shhh, calm down. I'm not mad, yeah?" 

She rubbed his back, pet his hair, kissed his forehead, and muttered constant reassurance to try to get him to calm down. "We'll get you cleaned up and it'll all be okay." 

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Elliott could not believe what was happening, not only did Rachel see him wearing a dress. But he had all so wet himself in front of her too. Tears and snot ran down his face as Rachel  put her arms around him, even as he tried to push her away, she did not let go.

Elliott's face went red as Rachel as she treated him like a small child,  rubbed his back, petting his hair, kissing his forehead, muttered constant reassurance and even lightly cooing at him. But the worsted for Elliott came when he was getting a hard on.

It was not like this was a new thing, when he first but on the Rachel's dress he had gotten hard, when he put the ruffly bloomers and it touched his dick he had gotten a hard on. But this, this was knew. Elliott did not know what was making hard, was it wetting his bloomers like a small child, was it Rachel finding out was it the way Rachel was treating him like a child, he did not know.

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Rachel held Elliot close until his tears lessened. "There we go, no need to cry." She praised as looked at the boy. "Let's stand up now and get to the bathroom alright?" 

She coaxed him up, and only noticed his hard on as she straightened out the now wet dress. "Oh...?" She was unsure of what caused it. She had heard of men getting boners when scared or humiliated, but didn't want to assume. Maybe it was the girly clothes. Or maybe Elliot liked her comforting him.

Deciding to deal with it later she used her finger to grab Elliot's chin to look her in the eye. "We'll talk after you get in tub." 

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After Elliott's crying had eased up and as Rachel took him to the bathroom, Elliot all most started to suck his thumb as he was led like a child to the bathroom, but fought had not too. After getting into the bathroom, Elliot watched Rachel turn on the water and added the bubble bath soap to the tub.

Elliot watched Rachel making the bath feeling very turned on, hoping to rub one out after Rachel left. But after the bath was ready, Rachel went over and soon started to undress him. "WAIT RACHEL ST-STOP I." Elliot said as the dress was taken off, showing off his light pink bloomers.

But then when Rachel got a hold of the bloomers, Elliot yelled out for her to stop, but it was to late as Rachel saw to her shock Elliot had no hair down their. Elliot could not take it, or more to say his dick could not take it as it soon prematurely ejaculated on Rachel's face.

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Rachel flinched as the first spurt landed on her cheek, the subsequent ones landing on her neck and chest. When it seemed he was finished, Rachel sighed and stood up. Grabbing a wad of toilet paper and wiping it off as best as she could. She wasn't mad. Maybe a bit annoyed, but not angry. Her shirt was stained though, so she just took it off leaving her in a sports bra. 

"Get in the tub, Eli." She ordered gently.

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Rachel gently took the bar of soap from him and kneeled beside the tub. "Relax. Let me help you." She said as she took a wash cloth and soaped it up. She started with his chest before going to his arms. Carefully soaping him down. 

"Mind telling me why you wore my dress?" She asked him as she continued cleaning. 

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When Rachel said she was going to clean him, Elliot started to protest only to be shhed by her. As Rachel gently cleaned Elliot like a child she kept on looking at how hairless he was down there, it was like looking at baby. She continued cleaning him she asked about the dress.

Elliot thought hard on what kind of reason way he was wearing girl clothes, but each reason each lie he thought of would fall flat as he squirmed getting clean cleaned. "I-I just wanted too."

Elliot said as he tried not to cry again.

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