Family Secrets (Smutty McPlot&NightDagger)

[NightDagger]

When Natalie first discovered her little brother was going to go to an all girl's school. Well she did what any older sister did; she'd laughed hysterically and then took him shopping for girl cloths like any big sister would. Especially for their....little sister's first day of school. Then she'd patiently taken it upon herself to teach him how to act like a girl and how to hide his...less then feminine parts. How did she know that you ask? Well tall busy Natalie had some less the feminine parts of her own.

Now after a summer of teaching him how to sit, act, dress, put on make-up and talk he was more feminine then she thought he would be. She'd even made him grow out his hair. Now if was finally time to begin school and the first thing they did was head to the dorm mistress to get her younger sibling a room. "Good afternoon Ms. Wilson, I was wondering if I could get a room assignment for my sister." Natalie smiled at the older woman dressed flawlessly in her school uniform. Always smart to make a good impression.

"Ah yes that's right your sister is joining us isn't she now? Lets see here....ahh it appears you don't have a roommate Ms. Johnson. Well I think it would be a shame to separate you. Go on and take her bags to your room, you two can share for the duration of your stay. Now here are your class lists, meal colanders, list of free weekends and everything else you may need. Enjoy you're school year ladies." and she turned away leaving the two to make their way to the dorms.

It took a good 15 minutes but eventually Natalie came to her dorm. It was in the newer wing of the school, a perk to having a history of female family members attending. She unlocked the door and stepped inside walking to the left bed and setting her suitcases on it. A boarding school dorm was not unlike a collage dorm. There were three rooms in all. A private bathroom, a small kitchenette and then the main room which, while quite large had two beds and two desks and flat screen TV. The walls were a dingy white and the floor was nicely worn oak. One window dominated the spaces between the beds a large bay window that overlooked the school garden.

"Welcome to our home away from home." she said lying out on the twin bed. "Ohh feels like they got new mattresses nice. How are you holding up brother of mine? Enjoying your first day as a girl?" she turned her blue eyes gaze to him curiously and grinned.

 

[Smutty McPlot]

Dylan had always had a bit of a feminine side being raised by his mother and sister, as well as the occasinal babysitter when they were younger. In fact, he had secretly been sneeking opportunities to dress in some of the clothes his sister had left behind while at school and their mother was working. He blamed it on being given a boy/girl name, their mother having decided to play it safe when choosing after having her daughter. It was the only real secret he'd kept from them, though when his mother made the announcement that he would be attending school with his sister and all that entailed. He finally broke down and admitted what he'd been doing.

Of course Natalie had laughed, he'd expected nothing less. But then she'd dragged him immediately off to the mall for a shopping spree. Of course, he felt like a doll at first, and had wondered if Nat had always been disappointed in having a little brother instead of a sister. The more he tried on the clothes, admiring his slender frame in the mirror. The more he'd grown to enjoy it. And over the course of the summer a closeness had developed between them that had never really been there, something he'd always attributed to that one thing that made her different from other girls.

He'd practiced everything from walking to talking, having to rethink the way his entire body moved, and had spent hours of most days dressed in his new persona. Dylan hadnt even needed to change his name, almost as if their mother had planned this all along. The long trip out to the school had taken them all day, and they'd stopped in town briefly for him to make any neccesscary touch ups before the real test began. His black hair, now glossy from the special conditioners he'd begun using had always been somewhat long, but at Natalie's urging he'd grown it out further this summer. Now it hung in thick glossy waves nearly down his back, adding to the illusion. The breastforms stuck to his own slender chest, and held in place by the bra he'd finally grown comfortable wearring all day long gave him the accent of a simple B cup bust beneath his school uniform. His older sister had made sure his appearance was as flawless as hers, and he was ready to do anything to keep from embarassing her.

He'd stayed quietly nervous once they arrived on campus, a bit surprised and completely relieved that he was going to be sharing a room with his older sister. It meant that he could actually relax a bit in their room, and not worry about his roomate finding out. His own paperwork from the office included a map of the school grounds, which he studied as natalie lead him to the dorm. The atmosphere changed once they were in the building, and Dylan's eyes widened a bit at the sight of the girls wandering back and forth from room to room across the hall in various states of in and out of uniform. Once in their room he took a deep breath, closing the door behind them and leaning against it to breathe a moment.

Dylan reached down to tug up the front of his skirt, slipping a hand into the simple pair of cotton panties that were regulation with the uniform. He had to loosen the straps that bound his male anatomy against his body to prevent it from causing a scene in the front of his skirt a bit, seriousy fearing that he might break something. He let out a sigh of relief as the pressure on his sensitive parts loosened up a bit, groaning a bit at his sister's question. Carefully he smoothed the skirt back into place, looking down to make sure he hadnt loosened the straps too much. "I think I'm going to hurt myself Nat... I saw at least two girls out there wandering around topless!" He picked up his bags once more, carrying them over to the remaining bed. Setting them down as he sat down carefully, shifting his hips slightly so he didnt have to reach down and visibly adjust. "I so cant do this for an entire school year..."

 

[NightDagger]

"Hmmmm? Yeah they do that in the dorm wing. It's not monitored for privacy reasons. Occasionally you'll catch a few running around in only their underwear." It didn't seem to affect her that much mainly because she wasn't interested in girls. She was straight in the female sense, but gay in the male. Peculiar really, she wasn't certain how many people could say they were gay yet at the same time straight, without being bisexual.

"Eventually you'll probably get used to it Dylan, if not you can always get some relief once we're in the dorm for the night." she let her eyes skim along his false female form. Every since they began to grow closer at times she found herself having less then innocent thoughts about her brother. Granted she chalked it up to hormones but if anyone would be comfortable with her male anatomy, it would be her own brother. Or so she'd like to think.

"I should probably tell you tonight is the beginning of the school year party. The richer girls sneak alcohol in and there's dancing and a lot of girl on girl action. I don’t usually attend for obvious reasons, but you're going to be for one hell of a night." she chuckled softly and sat back up on her bad after loosening her own straps a bit. Opening her suitcase she pulled out her laptop and set it on the desk followed by a lamp, printer and several photos and small little collectable stuffed toys. "Might as well get situated, school doesn’t actually start until this up and coming Monday. They usually give us three or four days to readjust first."

 

[Smutty McPlot]

Dylan groaned further at the thought of some of these girls parading down the hallway in their underwear, so well in fat that there was almost a noticable twitch beneath his skirt before he shifted his hips once more. Carefully he leaned down to open his own suitcase, following her example as they began to add their own little touches to the room.

Shocked a bit that the girls engaged in such activity, he shouldnt have been surprised really with all the stories that circulate on the internet. He'd always just chalked them up to erotic fantasies from a gifted immagination. Now however, he wasnt so sure. "But you dont attend, so it would make perfect sense for me to be just as prude as my older sister, right?" He grinned a bit at the joke, looking over at her a moment. "I couldnt imagine trying to get through something like that without you there to make sure I didnt mess up Nat..." Not to mention how painful the night would be all strapped up tight. With all his clothes on he'd stick out like a sore thumb if it was anything like what his older sister was describing.

 

[NightDagger]

"For most guys it would be a fantasy come true to see a bunch of girls making out. However given the circumstances, you know you can stay with me. I'm sort of an outcast anyways, I have a few friends mind you but most of them are in the scholarship dorms in the other wing. They're not as....rebellious as the girls in this wing tend to be. If your daddy has enough money you can get away with anything. Especially if they donate money to the school."

She turned towards him and smirked. "There was this one girl, that was not only training female sex slaves but she was whoring them out to the all boys’ school a few miles from here. She managed to get out of expulsion and jail time because her Dad's money built the entire library after the fire about 10 years back." she laughed softly and hung up a wolf poster over her bed.

"We can watch a few movies and makes some popcorn tonight if you want? It'll keep up occupied and it'll drown out the girls in the hallway. Believe me I've had practice in drowning out their wild parties." she chuckled softly.

 

[Smutty McPlot]

"You're right, under any normal circumstance it would be a dream come true. And maybe by the end of the year I could get away with it with a few girls... But right now, I just dont wanna risk it. She didnt even ask, but he moved over to her bed to help her hand gup the poster and get it straight. "Mom paid a lot of money to get me in here, and I dont wanna fuck it up Nat. So I guess it's best if I hang out with the good girls too..." He didnt want to accidentaly run across a girl like that, who knows the mess he could end up in.

Dylan grinned a bit hopping down from her bed to walk over to his own suitcase. Without thinking he bent over to rummage around. The back of his skirt rose enough to offer Natalie a view of his white cotton panties and the very obvious bulge strapped tightly to his body. He stood back up with a smile as he pulled out his PS3 with the expanse of cables clutched firmly in hand as he walked over toward the wall mounted flatscreen. "Too bad we're not bad girls..." He chuckled, setting the video game system on a small stand beneath the television. "We could sneak out and go back into town to go to see a new movie."

 

[NightDagger]

"Thanks." she responded as she finished hanging up the poster before turning her attention back to him. "I know Dylan, I was just giving you a hard time. Do you think I want you kicked out anymore then you want to get kicked out?" she raised an eyebrow her eyes drawn to his panty covered backside with quite a bit of interest before moving away when he stood back up and working on trying to thumb tack a dream catcher to the wall above her bed.

"Hmmm just because I said we were good, dosen't mean we have to be angels. I sneak out all the time, I know just the route to go." she bounced off her bed and slipped her shoes back on tightening the strap much to her dismay and familer discomfort. "Come on we can finish setting up later. Tighten your torture device and lets go that new action flick starts in 30 minutes." Making sure nothing was showing she grabbed his hand and yanked him outside locking her dorm room.

They made thier way through the packed halls and no one noticed a thing and the two slipped out the back and into the parking lot. It was a 15 minutes walk back to town but they traversed the near silent road and got the to theater just in time. After the move she went into the liquer store and came out with three bottles of various alcohol. "The guy that owns the store has a soft spot for me." she murmered. "Now you lead the way back and lets have a party of our own tonight what do you say?" she held up the bottles.

 

[Smutty McPlot]

"I know Nat... If you didnt want me here, you wouldnt have done such a great job at making sure I made the perfect little sister." He shrugged a bit, making sure the cords were all connected correctly. "The rest is up to me." He grinned a bit at her suggestion that they slip out to go see the movie he'd been dying to see. For weeks now he'd been disappointed after learning that it opened this weekend, and they would be stuck at school for a while before being able to leave campus. His own suggestion had been little more than wishful thinking, but now.

"He groaned a bit as he retightened the straps, wincing as the bindings pulled his still hard erection tightly against his body once more. Taking Natalie's hand, they were off. His heart beating rapidly as they slipped out of the dorms and off down into town. Dylan memorized the route, knowing he was going to want to do this more often.

He was on the edge of his seat for the entire movie, and when the left, he was a bit confused when Natalie decided to stop in a liquor store. He waited outside, every so often glancing in through the window to watch as his older sister flirted with the clerk. He'd had a happy grin on his face all evening, and it only broadened when she returned a short time later with the three bottles of alcohol. He didnt know what they were, nor did he really care, never having any experience with it before. But that was obviously soon to change.

"A soft spot... in his butt?" Dylan smirked as he ducked out of range of her hands after his joke. Ever since they'd become closer and he'd learned that she wasnt interested in girls, and in fact was attracted to boys, he'd been teasing her about it. It was never anything hurtful, in fact, he wanted her to find a guy that would accept her for the beautiful, intelligent hermaphrodite she was.

Carefully however, he lead the way back to the campus, darker now it was harder to spot the landmarks he'd noted on the trip out. It took a bit longer than their rush to town had been, but at least he'd learned enough to make it back safely. In the Dorm, the party was in full swing, and Dylan clung to Natalie's arm both in an attempt to keep random drunk girls from dragging either of them off, but to hide the liquor bottles between them as well. His eyes however were roaming into the various open doorways as they passed, whimpering a bit and biting his lip at some of the things he saw. Things that would be imprinted in his memories for years to come as the straps became painfully tight once more, causing him to cling tighter to his older sister's arm.

 

[NightDagger]

"Ha, Ha." she responded as the two of them headed away and she grinned softly. "Nah he just thinks I'm a cute school girl, doesn't know a damn thing about my extra equipment. I'm quite apt at flirting without making them think I want to sleep with them you know." she nudged his side before the two of them headed down the main street to thier school.

Sneaking it was about as easy as sneaking out, all they did was go through the back and use the emergency stairs which lead straight to the paying dorms. As expected the part was very much in Swing when they finally arrived. Girl danced against one another wearing nothing more then skimpy underwear. In a few of the open rooms it was obvious there were less then innocent things going on and often it involved three or four girls. Natalie rolled her eyes and unlocked her dorm before pushing Dylan inside and shutting the door.

"It gets worse every year I swear." she murmered. Turning on her radio she put on something to drown out the god awful music they were listening too. "There now I for one want these goddamn straps off for a little bit." Slipping into the bathroom she stripped out of her school uniform and by default the straps that kept her anatomy hidden and pulled on and over sized shirt and a pair of boy shorts before re-emerging. "You can take yours off too. Now we have whiskey, vodka and tequila by the looks of things. Which one do you want to try first?"

 

[Smutty McPlot]

By the time Natalie had emerged from the bathroom, Dylan had already removed his own straps. As well as the simple white cotton panties worn beneath his uniform. His back was to the bathroom door with the front of his skirt hiked up as he inspected the marks left on his member by the binding straps. The action incidentally pulled up the back of the skirt as well however, showing off a hint of his firm young rear.

He nodded a bit before snatching up an oversized t-shirt of his own, and tugging the skirt back down in place. It did little to hide the large bulge as it tented out the front of his skirt. He shrugged a bit with a grin as he nearly skipped to the now open bathroom door. "I dunno what any of them taste like, so I'll let you surprise me..." He giggled a bit before disappearing iinto the bathroom to change.

It was only a few minutes before he too emerged from the bathroom, dressed in similar fashion, an over sized tee-shirt. Any other time he would have taken longer in the bathroom trying to relieve himself, but the straps had left him sore. Thus the lack of boy shorts that still lay on his bed, in the hopes of relaxing a bit. Without the bra or the breast forms, it left him in a nearly dangerous state between looking like a girl and looking like a boy trying to be a girl as he flopped down on his bed with a slight groan.

 

[NightDagger]

((Sorry for the wait, the holiday week was a nightmare.))

"Poor baby." she said when she noticed the marks on his poor tender cock. Almost as much as she was admiring him fully hard, it was quite interesting to see how comfortable he'd grown around her. She supposed it was nessicary given she had to teach him how to put on and take off the straps. The entire activity had required alot of touching and stroking so he'd grown used to her touching him there.

By the time he exited out of the bathroom she had poured several shots glasses worth of the various alcohol. After pausing for a moment to admire his ass she sighed softly as he laid out on his bed. "Well if you weren't straight as an arrow half nude girls wouldn't bother you so much would they?" she teased. "Here down a couple shots it'll make you feel better." she pushed two towards his side of the shared end table with a smirk before downing two of her own and sighing as the alcohol burned her throat.

"Your turn." she winked at him playfully before moving to his bed and nudging him in the leg. "We can't have a party without getting drunk first." laughing she nudged him again her hand squeezing his upper thigh gently. It was a surprisingly sexual movement but it was so brief that it was likily he didn't quite catch onto it.