Looking Through the Glass
by Silvergunner

Sitting on the bed in her room, the teenage girl was deep in thought. Her room was neat, tidy, and decorated in a mixture of purple furnishings and decor. A large wardrobe held a selection of dresses, skirts, blouses and other fashionable feminine clothes. She felt happy the way she was now, but in the back of her mind there was a thought she couldn't get rid of. She wondered what it would be like if she wasn't a girl at all.

She was used with hanging around with friends of both genders. As well as her female friends at school who slept over occasionally, her older brother tended to bring home his male schoolfriends for the evening. They all got on well with each other, as he was very friendly and caring to everyone he met. She was indeed very close to her big brother.

Many girls her age were curious about boys and how they were different, but she didn't have that curiosity. She had seen her brother and his friends naked before, and seen her own female friends engaging in very naughty activities during their sleepovers. Like her brother and his friends liked to jerk off while watching a movie at their sleepovers, she and her friends masturbated together in the bedroom while telling each other stories at theirs.

She was especially close to her brother for another reason as well. She had not been a virgin for a long time, yet she had never had a proper boyfriend. The reason being that her real boyfriend was her big brother. She had never felt so much love for anyone but him, and after their first time together when she was younger their hearts were bound by their love for each other.

Although she liked been a girl and especially how it felt during sex, she did wonder what it would feel like to be a boy like her brother. When she was at her previous school she was called "Molly the Tomboy" by the other kids. Although they meant to tease her, she wondered if there was a hint of truth in it, especially after having these thoughts for a few weeks now.

The thoughts streaming through her mind were about how she could try been different for a day, and they had helped her in conjuring up a plan to do so. However she knew that if it went wrong, she would be in big trouble with everyone who could potentially get involved. As she sat on the bed, she looked in the mirror and saw her young, cute face adorned by her glasses staring back at her. Smiling, she made her decision and stood up. Pulling a fluffy pink dressing gown over her body, she left her room, ready to carry out her plan.

As Molly walked through the house with only her dressing gown covering her body, more thoughts flowed through her head. Thoughts of an obscene nature that she tried to suppress the best she could. But they were too tempting for her to ignore any longer, and they flooded her head as she crept quietly along the hallway. She had let her thoughts run wild that afternoon, and she imagined all the fun she was about to have as a result. And especially how naughty it all was going to be...

She felt that her big brother would be incredibly angry if he found out what she was about to do, and she hoped he wasn't in his room as she stealthily crept to the wooden door to his room. It was slightly ajar, so she pushed against it lightly so it swung open slightly, before taking a look inside as stealthily as she could. With sketchbooks piled on the desk next to his laptop, guitar magazines scattered over the bed, and clothes chucked on the floor, it was the typical teenage boy's bedroom. And more importantly, it was vacated. He had talked about a jam session with his garage rock band the night before, and Molly figured he must be there now. Breathing a sigh of relief, she walked in and shut the door behind her. She was about to try something so perverse, even she was surprised she had conjured it up in her mind.

She walked over to the far side of the room towards a chest of drawers where he stored all his clothes. Beside it however was a small pile of used clothes he had obviously worn the day before, and probably chucked to one side lazily before bedtime. Absolutely perfect, she thought to herself as she kneeled down and began shuffling through the pile.

After a minute of shuffling, she found a pair of onyx coloured jeans and a scarlet t-shirt with the insignia of a band he liked upon it. As if from instinct, she raised the clothes to her face and inhaled deeply. The essence of his body flowed into her nostrils, and she smiled as she imagined him lying next to her and cuddling her all night long, as she inhaled the scent of his warm, handsome body.

She snapped back to her senses and figured she had to move on quickly in case her brother arrived home earlier than normal. Standing back up, she moved over towards his bed. After taking the magazines and placing them onto the floor then placing the clothes upon the bed for a moment, she turned and gazed into the mirror hanging on the wall above the chest of drawers. She tugged at the belt of her dressing gown, spread her arms and let it slip off her body gently. Her naked body came into full view, and she giggled as she gazed at herself in the mirror. She was a slightly tubby girl, and the warm air flowed against her small developing breasts. She adjusted her glasses and gave a smile that complimented her beautiful face perfectly.

Taking the jeans first, she pulled them up over her legs and up against her tummy, before fastening them and pulling up the zip. They were rather loose on her and sagged downwards, but she was too focused on taking the red shirt and pulling it over her head to focus on the issue of her private parts been on public show when the jeans sagged. However the shirt resolved the problem to a degree, as it was several sizes too big for her and long enough to cover her loins and butt completely. Pulling the trousers up again, she looked in the mirror once again.

For a while she had wondered what it would be like wearing boys' clothes. As she looked at herself in the mirror, she smiled. She loved her own, more feminine selection of clothing. But been dressed like a boy didn't feel too bad either...

She had originally planned to go back to her room after trying them on, but more desirable things had come to her mind upon pulling the clothes on. She jumped backwards onto the bed and smiled as she laid upon the dark blue covers. She could feel her big brother's essence rubbing against her skin from the clothes, and it made her feel really happy inside.

After lying there happily for a few minutes, she couldn't hold herself back any more. She placed one hand against her breast, and began flicking at her nipple through the flimsy fabric of the shirt. Another hand reached downwards, and she pulled the zip of her jeans open before pushing her hand inside. As she was dressed like a boy, she may as well pretend to be one while masturbating, she thought to herself. As she began caressing her breast more with one hand, the index finger of her other hand began rubbing up and down between her vaginal lips. Her motions were more vigourous than normal as she was moving her hand in and out of the space between the zip, pretending to be a boy jerking as far as hand motions were concerned.

Downstairs at that moment in time, the backdoor swung open and a teenage boy walked through. He was tall and handsome, and looked a lot like Molly did. Walking in and closing the door behind him, Figlet Hudson sighed. Band practice had been rough that day, and he was glad to be home finally. Time for him to put his guitar away, lie back on his bed and chill for a few hours before his mom came home.

He walked up the stairs towards the bedrooms, lugging his guitar behind him. He hadn't used the toilet since that morning, and really needed to go. He planned to sling his guitar in his room first, before heading to the upstairs bathroom. As he walked towards his room, he paused suddenly. He could hear moaning coming from behind the door. Wondering what was causing the noises, he grasped the handle.

Molly was just about to push her index finger into her pussy when the door swung open suddenly. From behind it she saw her brother staring into the room, his eyes surveying it until they met the eyes of his little sister. She let out a cry of surprise when she saw he had walked into her with her hand slid under her clothes. Figlet himself looked surprised to see his little sister in front of him, caught halfway through masturbation while dressed in his clothes.

Dropping his guitar bag against his desk, he walked over to her. "Molly, why are you on my bed dressed like me?" he asked, giving her an inquisitive gaze.

Molly blushed, her hand retracting from between her legs. She tried to think of an adequate excuse, but none came to mind, and she decided to come clean. "I... Just wanted to know how it felt been in your clothes Figlet. How it feels to smell and dress like a boy..." she stuttered.

He smiled. "So I'm guessing you like dressing like a boy then Molly?" he asked her.

She smiled and nodded. "It feels really funny but really nice at the same time, Big Brother" she replied.

He grinned. "Well in that case... I'm going to have to treat you like you are a boy tonight then my little sister" he said to her. He walked over and sat on the bed next to her. Before Molly could say anything, he had leaned down and planted his lips upon hers. Molly felt him kiss her casually, not with the passion he normally kissed girls with. She giggled and returned the gentle kiss, as she let her hands begin to caress her body again. Figlet smiled and gazed into her eyes. "You are such a handsome young boy, Molly" he said to her.

"And you're such a handsome big brother" Molly giggled in response.

Her brother broke the kiss suddenly and stood up. Molly watched as he undid the belt on the jeans he was wearing, and slowly pulled both them and his underwear down. Into view came his cock, already slightly stiff from the thoughts running through his head. Molly made a really pretty boy, he thought, and he planned to show her how intimate two boys could be towards each other. He walked over to the edge of the bed and looked down at his sister. "I think you know what to do already, Molly" he said to her, smiling.

"Oh I sure do, Big Brother" his sister giggled. She flipped her body around so she was on all fours, then moved so she was facing her brother. With one hand supporting her, she used the other to stroke her brother's cock up and down the shaft a few times. She then shuffled a little closer and began licking at the tip gently before running her tongue up and down his steadily hardening member. Her free hand moved almost involuntarily towards her groin again and after sliding her hand through the zip, she began shoving her index finger in and out of her pussy. Both of them were getting incredibly turned on by the foreplay, both making slight gasps as she continued licking his penis while fingering herself.

Suddenly, Figlet chuckled and pushed his hips forward. The tip of his member brushed against Molly's lips, and she knew what to do next. She opened her mouth wide and felt Figlet's fully erect cock slide into it. She began sucking at it gently as she plunged three fingers in and out of her vagina furiously. Both were letting out light moans, and Molly smiled as she continued giving her brother a blowjob. She enjoyed doing this to him, because she knew how happy it made him, and how he would soon return the favour once he had reached orgasm...

Suddenly, she felt his cock slide out of her mouth as Figlet pulled his hips back. She looked up to see him smiling as his cock, slicker thanks to her saliva, appeared harder than ever. "Something wrong, big brother?" she asked him.

"Nothing wrong, it's just it's time to move on. It's time for you to get fucked just like a boy" he replied.

"Do you mean... In my butt?" Molly asked him. Figlet nodded, "Well in that case, I guess there are advantages to been a boy" she giggled in response. Reaching behind with her free hand, she pulled the jeans downwards so although her womanhood was still hidden from view, the rounded shape of her butt was in full view of her big brother. "Fuck me in the ass then, Big Brother" she whispered to him.

"Certainly my little sis" Figlet replied, grinning. Kicking his shoes, socks, jeans and underwear off his legs and against the chest of drawers, he clambered onto the bed and positioned himself until he was behind Molly. He used both his hands to rub against her butt softly, pulling her cheeks apart slightly so he could see her tight tailhole in front of him. He moved his hips around until the tip of his large cock was poking against her rear entrance. Breathing in deeply, he thrusted his hips forward, and his member, lubricated from his sister's saliva, slid into her butt steadily.

Molly let out a gasp as she felt her ass penetrated. She had tried anal sex quite a few times now, but her tailhole always seemed to remain incredibly tight. She felt her brother beginning to move back and forth and she began making loud moans as she felt his member slide in and out of her ass in a steady rhythm. Whilst her brother was pounding her backside, her free hand was now shoving four fingers in and out of her pussy furiously. She loved taking her brother's cock in her rear, and it was turning her on so much her whole body felt hotter than hell.

Feeling her warmth radiate through the skin of her buttcheeks, Figlet speeded up his thrusts. More and more of his cock slid into his sister's tight rear with a little difficulty, but as he speeded up it became slightly easier. Feeling close to orgasm, he pulled his hips back then slammed forward against Molly, all eight inches of his cock sliding into his sister's rear.

This was all too much for Molly, and her orgasm hit. She screamed as pleasure flowed through her body, and her pussy juices gushed out and soaked the jeans she was wearing. Her epic orgasm had made her tailhole tighten, and the extra tightness was enough to make her brother hit his orgasm soon after. He let out a roar as shock waves of pleasure surged through his body while his cock spurted his seed deep into his sister's behind.

As the two of them gasped for breath in the midst of their afterglow, Figlet suddenly felt a tinge of discomfort deep within his body, and he remembered he was distracted on his route to the bathroom earlier. He really needed to go, but was too tired to move. However suddenly, a wicked thought entered his mind as he recalled an incident or two that had happened in the past. Grinning, he breathed out and relaxed himself.

Molly was coming around from her orgasm when she suddenly felt even more warm fluids pouring into her ass. She turned around and saw Figlet sighing in relief. "Are you doing what I think you are doing, big brother?" she asked him.

"Well, you did distract me on the way in when I was heading to the bathroom, Molly" he grinned. Pee was shooting out of his cock and pouring into his sister's ass, with all of his eight inches still buried inside her. Molly let out a squeal of delight as she felt her butt filling up with the contents of her brother's bladder. She loved it when her brother peed inside her, either in her ass, her mouth or even her pussy. While her brother continued urinating inside her, she felt her stomach begin to bloat from all the liquid inside. By the time his golden stream had come to an end and he was depleted, her tummy was full to bursting from her brother's combined fluids.

Breathing in deeply as their afterglow subsided, Figlet slowly pulled out of his sister's behind. His cock eventually made its way through her tight rear and came out with a small pop. Molly gasped as her brother's fluids began pouring out of her stretched open rear, and into the jeans she was wearing. She bent her head downwards so she could see underneath her body, noticing how soaked the jeans were. "Oops..." she murmured.

Figlet chuckled. "Well, it seems you have ruined one of my best pairs of jeans, you naughty boy" he said to her.

"Oh, I'm not totally responsible. I didn't fill my own ass up with cum and piss" Molly replied, giggling. She let herself drop to the bed, and turned around so she was face up. Figlet laid down next to her and moved so they were face to face. They kissed each other casually on the lips again before breaking it and embracing in a hug. Figlet smiled as he felt his sister's chubby yet beautiful body in his arms, and Molly inhaled her brother's body scent.

"So..." Molly started suddenly. "You never told me you were into having sex with boys as well, big brother" she said to him.

He smiled. "Yeah, I've been bisexual for a while Molly. I've tried to keep it quiet though" he replied. Looking up at the ceiling he sighed. "I don't care about race or gender or anything like that. It's the person inside who I love" he explained.

Molly smiled at his words. She gazed at the ceiling too, and more thoughts entered her head. If Figlet was Bisexual, what if the reverse of what happened today took place. "How about you pretend to be a girl next time, and you can make a mess of my clothes instead" she asked him.

Figlet chuckled nervously. "Sure, I'll give it a go" he replied. "After seeing you dressed like a boy, I'm curious to how it would feel been dressed like and bonked like a girl..." he wondered aloud. In his mind he imagined Molly coming onto him with a large pink strapon dildo while he was dressed in a pretty dress. Crossdressing wasn't something he ever thought he would try, but it was a tempting idea.

"Well, next time I'll catch you in my room" Molly giggled. She hugged her brother again and they laid there together in embrace until tiredness got the better of them. They fell asleep together, Molly still wearing the soaked jeans, both content and happy. They both knew now a hidden part of themselves had been revealed both to them and each other, and it had unlocked a myriad new possibilities for the two of them to love each other.

- The End -