Happy Halloween

It was cool crisp October day when James Madden received the call on his cellphone that the package that he had ordered was finally in.
Rushing to his mailbox from his last class, grade 10 drama class, he was greeted by the clerk behind the counter.
Mickie smiled at the scrawny boy. at 5'5, and barley 120 pounds the boy had been to her store everyday after school for the pass three weeks, awaiting some sort of package.
"Hey James, did you break any speed records on the way over?" she teased, already pulling out the large brown box onto the counter.
the box itself gave away nothing of what was inside, and the paper work on the top named James as the receiver.
"No." Gasped the boy, panting and trying to catch his breath.
"Well OK. I need you to sign for this..and then it's all yours. though I gotta admit, I wanna know what exactly is it that's in here that's had you so excited?" She asked, handing over a clipboard.
In her 30's she was still fairly attractive, and wore her long blond hair in a pigtail, while James, having almost the same amount of red hair, wore his free.
"And I told you, I'm never gonna tell you" he said, blushing but smiling, as he signed the paper,and then took the box..and stopped to look at his book bag which wasn't going to fit said box.
"Aw crap.." he muttered.
"Problem kiddo?" She asked, with a knowing grin.
"Well, I didn't exactly bring something for this to fit into." He said with a sheepish smile.
"Well, if you don't mind waiting anther ten minutes, Tim is suppose to be here, I can use my break to drive you home." She offered.
"Really, you don't mind at all?" He asked, breaking into a big toothy grin.
"Nah, I've been to your place before, for your parents X-mas party last year remember? It's no biggie." She said, waving her hand as if to blow the question away.
"Thanks!"
"Just go have a seat, I'll nab you when I'm ready to go." She said.

A bare fifthteen minutes later, they were in her old beat up pickup truck, and driving towards his house. James could barley contain himself, and was bouncing around in his seat.
'Please let no one be home, please let no one be home..' He thought.
"Jeeze kid, lay off the red bulls." Mickie said, glancing over at him. "If it wasn't for the silly grin on your face, I'd think you needed to use the can!" Mickie joked. "Whats in there, some game system?" She asked
She knew the package was too light for that, and in fact had a hunch she knew what was actually in the box, But wanted to give the kid a out.
"S-Something like that." He stammered, trying to stay still, but almost started whopping when they came up to his house, and neither his parents car nor his sisters was in the driveway.
"Well, here you go. have fun with your game." Mickie said, a big grin on her face.
"T-Thanks." James said and got out of her pickup. "I'll see you around, bye!" He added, and then dashed towards the house.
"heh..cute kid. I hope he has enough sense to lock his door." She said, having received package from that company before. they were mostly discreet, but when you worked in the mailing business as long as she had..

James was breathing fast and fumbled with his key as he unlocked the door. Finally managing to get the key in the hole, his hands shaking, he rushed inside, slamming the door and run for his bedroom upstairs.
Practically driving into his room, he tossed the box on his bed, and kicked his sneakers off.
His room wasn't like most over teenage boys, Instead of a mess his room was neat and tidy, with blue carpet on the floor and white walls covered with posters of WWE wrestlers. truth be told, he wasn't exactly found of wrestling..but he did like seeing guys in tiny little shorts.
Striping down to his jeans now, he tossed his shirt in his hampered, set next to his computer against the back left corner of his room, and moved over to the box now.
"I can't believe it's finally here!" He practically squealed, feeling weak in the knees as he used his house key to slice the tape on the box, and open it up.
Inside the box was a pink pair of plastic panties, ruffled on the butt, and if that wasn't odd enough, considering this was a package for a teenaged boy, was also a light pink baby doll, with a big red heart on the chest. Underneath THAT was a pink adult sized pacifier, on a black string to be wore around the neck.
"Oh my god.." He whispered, putting a hand up to his mouth.
Looking over at the clock, he knew that he really should put all of this away, hide it under his bed along with the pack of attends he had brought a week ago. But he HAD been waiting sooooo long for this stuff to show up..Wearing it for a few minutes wouldn't do any harm. He'd hear his Parents or sister pull into the driveway anyways, so there was really no risk.
Biting his lip, James who had known for awhile he wasn't anything like most other boys, bent down and reached under his bed, pulling out the package of attends.

Ever since puberty he'd been noticing the boys, not the girls. he found himself thinking of odd things..Like being a pretty little girl. Confused but not wanting to talk to his parents about it, James used his computer to find out that he wasn't the only guy who felt like this. Waves of emotions had flooded over him, from arousal at some of the sites he found, to his relief that the wasn't the massive freak he had started to think he was.
He'd made a few like minded friends online,and it'd been one of them who'd helped him find a website to order the baby girl items he now had. It helped his parents had gotten him a pre-paid credit card, though he was responsible for putting the money on the card.
Buying the diapers had been nerve wracking, he'd been sure the clerk knew exactly who the diapers were for, and what his plans for them were. the smirk on her face, god, she'd been barely older than him by the looks of things! Thankfully he hadn't seen her around school,though it also helped that this was his second time in 10th grade.

Back in the moment, he had finished tapping up the diaper, and looked over at himself in his full body mirror. a smile broke out on his face, and he felt a rush go though him.
Wanting to look like some of the sissies he'd seen on the internet, he reached for some more diapers, stopping once he was triple diapered.
"Oh god." he lisped, in his best little girl voice, wiggling his bulging behind at the mirror,looking over his shoulder.
For awhile now, he'd been using lessons learned in drama class to help talk like the girl he wanted to be, and he thought he was doing a pretty good job.
with trembling hands, he picked up the plastic panties, glad he had ordered a larger size. somehow he knew he'd be thickly diapering himself, so he'd gotten plastic panties he knew were up for the job of fitting over them.
Still, it was a little bit tricky getting them to fit over, and he knew that at most, he'd be able to go 4 diapers if he wanted to use the plastic panties.
he almost stopped right there, cheeks burning as he looked at himself, and he was fighting the urge to go and take care of himself, knowing that after masturbating he usually lost his urge to wear. with a deep breath, he reached over and tugged the babydoll on, loving how it just started to come down and cover up his diapers.
Finally, he grabbed the pacifier, and slipping it around his neck, he the put the nipple into his mouth, and sucked a few times, looking at himself in the mirror.
'Ok, this is pretty cute.' he thought, though something was missing.
Snapping his fingers, he waddled towards his door, loving how his legs were pushed apart, and headed for his sisters room,to borrow some elastics.
'pig tails. I'm gonna look SO cute!' He thought, almost getting dizzy.
walking around his own house, diapered and dressed like a girl, he was going though a sissy overload. Like many sissies before him, he was in that state where really bad ideas sounded like fun. if he was thinking strait, he would of grabbed the brush and hair elastics before even starting, and would of waited till he could get them some time when he wasn't dressed like this.
Instead he opened his sisters door, and waddled over and grabbing her brush, and two purple elastics. again, if he was smart,or thinking right, he'd waddle right back out of her room, and go back into his.
Instead he looked at her vanity table, and smiled around the pacifier again, and sat down,starting to brush his hair.

Alice was having the day from hell. in 12th grade, she STILL didn't have a boyfriend,and it was starting to look like she never would. Her latest attempt to ask out Rick, the captain of the football team had ended with him laughing in her face.
"I don't date buff dikes." He had said.
it took all of her self control not to deck him right there, and on the flip side, not break into tears either.
Was it her fault that she was a towering 6'6? or that she liked to work out? Sure it left her with bigger muscles than most of the boys in her class, and she wasn't really into dressing like a girlie girl most of the time. but she still wore makeup, did her hair..And she was totally into boys NOT girls.
"Screw him, I'll find someone else." She said, pulling into the driveway, and got out of her car.

It wasn't until he heard the front door slam, That James realized that his sister was home. He only had one pigtail in but bolted up, and started to dash for her door.
'Please go and watch TV in the living room, Please go and watch TV in the living room.' James pleaded in his mind.
He opened the door, as he heard her call out.
"James, you home?" came her voice, from the stairs.
He bolted across the hall, trying to reach his room before she made it up the stairs, and just had his hand on his doorknob when he heard her.
"James are y-" he turned and looked at her, still on the stairs, looking at him in shock.
"What are you wearing?" she asked, a look of amusement breaking over her face.
The pacifier dropped from his mouth and James mind spun widely, trying to think of something,anything he could tell her.
"I-It's my..Halloween costume." he said.
"Really, you're going out, dressed like THAT?" She asked, coming up the steps.
Going out..oh crap, what had he just said!?
"Y-yeah. I uh, Thought it would be a huge test..of um..How far I've come with taking drama class..if I ah..Can play off a girl dressed like a baby for Halloween!" He said, stalling several times and praying that she brought it..it would be least humiliating than the truth right?
"Well, I have to admit, you do kinda look a little like a girl..but you need some makeup..and something to give you tits." Alice said,not buying his story for one second, but after the day she'd had, she was going to love this.
"O-Ok..I'll find something to work with." He said, getting his door opened.
"Nonsense little brother..or should I say sister.." Alice said, coming up the stairs, and firmly grabbing James wrist.
"After all, what kind of big sister would I be if I didn't show my little sister how to look pretty." She added with a giggle.

For the next hour, James sat in his sister's room, having her fiddle around with bra''s till she found one of her older ones that would fit him,and she stuffed it until even he had to admit, he looked like he had a rack.
Next came the make up lessons, followed by being taught how to do his hair the right way. in the end, it was kinda sad but James had to admit he pulled off a teenaged girl in diapers.
"Well, I've worked my magic." Alice said, patting his head. "now it's all up to you..if you wanna pull this off for Halloween." She said, a knowing tone in her voice.
"Y-yeah.." He said, in a very small voice.
'there has to be a way out of this.' He thought desperately.
though also truth be told, looking at himself like this..he was glad he was so thickly padded..because it hid his erection.
"What..what if i wasn't so sure about going out like this anymore?" He asked, poking his two index fingers together softly.
"Well, Considering how your dressed,I don't blame you for getting butterflies in your tummy." Alice said, coming over and reaching down to tickle her brothers stomach.
As he giggled, well like a little girl, she lifted him up, and carried him over to her bed, plopping him down and going on with her tickle assault.
"however, after all the work we've gone though..and the pretty penny you must of spent getting all of these supplies, I think you should go though with it. I'm sure mom and dad will agree when they get home."
"Bwhahahahah! W-Wait! heheheh M-mom and dad!?" He yelped/giggled. "I don't hahahaah! them to see me..me..like this! Hehehe!" He giggled, unable to get away from his sister.
"Well, how did you think you were going to get out of the house to go trick or treating otherwise?" She asked, taking a break.
"I-I don't know." He said, red faced and panting, on her bed..and slowly becoming aware of a warm wetness in his loins.
"A-Alice..I uh..Need to go..and change." he said..still red faced but for a whole new reason.
"What do you mean you need to..oh..OH!" Alice said, and then started to look sheepish herself.
"Did..did you um..Wet or.." Alice asked, rubbing the back of her head.
"Or what..oh!" James said, and then looked sheepish as well as humiliated. "No..I just..um..peed." he said.
A long silence went over the room, and then brother and sister locked eyes, and both burst out laughing.
"Well, This is a interesting moment in our family history." Alice giggled, and then they heard a car pull into the driveway.
"Mom and Dad!" James squeaked, going pale.
"Better waddle fast and get those soggy diapers changed..I'll go down and prep mom and dad for what your going to be wearing downstairs." Alice said.
James opened his mouth to protest, and Alice took the pacifier still handing around his neck,and poped it in his mouth.
"Listen, either you come down, like this but in clean diapers..or I tell mom and dad only what I saw, not the whole story." She said with a smirk.
James meekly nodded, and waddled back to his room, wondering what had he gotten himself into.