Hi, so I did write a story on here ages ago, but can't even remember what it was called (or what name I used). It never got finished anyway though, so here's something new, and it works quite well as a stand alone tale.
I decided to do something a little different with this, and set myself a bit of a challenge; I wanted to do a fairly sweet coming of age tale, something without overt sexuality in it, but that was still focused on a sissy. If that makes you want to not read this, well I think (or hope) you'll be pleasantly surprised.
We all know most sissy stories usually end up with some combination of forced-fem, incest, humiliation, overt sex, underage sex, bondage and so on. These are all the things I wanted to avoid.
As I said, I was aiming for a fairly sweet, coming of age, self discovery, kind of tale, with only a minimal mention of anything related to sex at most, and this is what I ended up with. I hope you enjoy it.
"Mum, I'll be fine, seriously. I'm old enough to look after myself for a few hours; and you'll be home well before dark anyway." David had been pushing to be allowed to stay home alone ever since he started high school, and now he was on the cusp of getting his wish. His Mum had finally tentatively agreed, as long as he cleaned his room. David had, of course, agreed instantly; a few chores were a small price to pay for not having to sit through a day of everything football with his Uncle Josh. Now if he could just get his Mum in the car before she changed her mind again.
Georgina "Georgie-don't-call-me-Gina" let out a long suffering sigh at her growing boy's push for independence, and after checking again that he had the phone numbers for her office and mobile, as well as for his Uncle, she gave him one final hug - which he didn't quite squirm out of - and got into her car. She waited till he closed the door before pulling out of the driveway, certain there was an eye roll involved, then headed off to work.
David closed the door then watched through the stained glass panels as his Mum pulled out and drove off, he waited till the sound of her car had completely faded away into the distance, then turned away from the door. With a shiver of excitement, he practically skipped down the hall to his sister's room, his hands shaking as he looked about her den of utter femininity. This is what he'd been waiting for; the chance to try on her things without the risk of getting caught, and he had hours till Mum would be home!
He wasn't entirely sure when or how he'd started wanting to crossdress, but he'd been taking chances for years now. A skirt from the laundry here, a pair of high heels in the entryway there; stolen moments of girly delight. The opportunities had increased when his sister, Beth, had moved away to go to university; she'd wanted to be a nurse for as long as anyone could remember, and continued to work hard to achieve her dream. David however was the artist of the family, he didn't know what he wanted to do with his life, but right now he just wanted to be pretty.
There was no question about what he was going to wear, not this first time, after so much planning, dreaming, and sneaking through Beth's things to see what she'd left behind. With a squee he didn't know he had in him, he threw open the wardrobe doors and started to reach in, when he stopped. He was positively bouncing with excitement, and his palms were sweaty; which was what made him pause. He didn't want to spoil any of the lovely girly things, he wanted to be able to wear them again and again. "Shower first," he told himself, and with a nod went off to the bathroom.
He took the time to enjoy the shower and calm down, scrubbing himself as clean as could be, and even using some of his Mum's flowery bodywash to help set the mood. There was a pack of razors there, and he so wanted to shave his legs for the right feel, but couldn't risk it with his school shorts. He took a razor anyway, and removed the few hairs from his underarms; no one would notice that. Stepping out of the shower fresh and clean, he dried himself off and wrapped a towel around his body the girly way, as he'd seen his Mum and Beth do, then padded softly toward his sister's room.
The shower had relaxed him, so he was no longer shaking, and the new scents clinging to him had helped set the mood. Taking his time, he gathered what he was after, starting with underwear. The panties were brand new, he'd found the unopened pack of three hidden in a bag in the wardrobe during his explorations a while back; they were soft cotton, obviously nothing too expensive, but a light pink with just a hint of lace around the legs. They were perfect, and better yet, there was a bra that matched them near enough perfectly. The lace tickled the light hairs on his legs as he pulled them up, it was a nice feeling, but he really wished he could shave; that must feel so much nicer. He positioned his boy bits in just the right spot as he settled the panties around his waist; too far back and it hurt to sit on them, too far forward and there'd be an ungirly bulge. His penis had stiffened a little, but he'd found that just helped hold it in place.
With the panties on, he slipped the towel off and hung it over the rail at the end of the bed, then picked up the bra. It wasn't quite the same shade of pink as the panties, and the little satin bow between the cups was a different colour to the one on the front of the panties, but they still matched pretty well. It took him a little while to get it on and done up, then he had to take it off and adjust the straps before twisting around to get it back on again. Satisfied, he filled the cups with some padding he found in one of the drawers; remembering how quickly Beth had grown boobs, and smiling at now sharing her secret.
The second drawer of her dresser had tights, pantyhose, stockings, and socks in it. He'd searched through it in advance to find the perfect pair; the tights weren't too thick, but also not so thin that his leg hairs - sparse though they were - would be noticeable, plain white without any prints, but with some sort of shimmery glow to them that he loved the look of. He'd seen his Mum change some torn knee-high stockings before, so tried doing what she'd done by bundling them up into a ball, and gradually pulling them up his legs. That seemed to work, and felt even better sliding up his legs than the panties had. He got his right leg up to his knee, did the same with his left, and then came a lot of careful pulling and prodding to get them up to his waist. He ended up having to take them back down to his knees and try again, as somehow he'd got things all twisted around and just weird feeling, but in the end he got them on without tight spots or oddly twisted seams.
Taking a moment to rest and sit on the bed, he wiped the sweat off his forehead with the towel. Who knew girling up could be such hard work?
Having caught his breathe, he went back to the drawers and got a pair of socks, sat back down, and pulled them on. He didn't think real girls wore socks and tights at the same time, but he wanted extra girly; and the soft ruffled lace around the top of the socks was exactly that. He thought about shoes for a moment, then decided it'd be easier to finish with the clothes first, he just hoped his idea worked.
Skirts and tops were all very well, and some could be super cute and girly, but nothing was as distinctly feminine as a dress, according to David. The one he pulled from the wardrobe was perhaps not as fancy as some, be he loved the colour; a light girlish purple that probably had a name all of its own that he'd have to learn some day. The neckline was high enough that it didn't make his lack of real boobs obvious, and the sleeves were light fluttery things with a triangular shape to them. The bodice continued down fairly plainly to the waist, where the skirt part suddenly erupted in layers that fell to just above the knee, with a shimmery top layer that matched the sleeves, and went perfectly with the shimmery tights. But David thought it could be made super girly with one addition; carefully laying the dress on the bed, he reached into the back of the wardrobe and pulled out another hanger. This held a petticoat made up of masses of soft fabric that would puff the skirt of the dress out in such a blatant display of girlish softness that he couldn't possibly go without it.
Now he just had to work out how to put it all on. He wasn't sure if you were meant to step into the dress like you would a skirt, or pull it over your head like a t-shirt. He'd never be able to step into it with the petticoats on, so was that meant to be added last? Deciding to try pulling the dress over his head first, David soon discovered that wasn't going to work, stepping into it worked much better. Pulling it up to about the right place, he slipped his arms into the sleeves and pulled the dress the rest of the way up. Much twisting and pulling and grunting followed as he tried to zip the dress up, it was the bra all over again! He got it after a little while though, then sat on the bed again to catch his breathe.
A few moments later he reached for the petticoat, unclipping it from its hanger, before trying to work out which was the front and the back. There didn't seem to be much difference besides the tag, so guessing that went to the back, he stepped into it. It was so puffy! He had to bunch the dress up around his waist, hold it up, and pull the petticoat up, a third hand would have helped. But he got it before too long, then gently pulled the skirts of the dress back down and into place.
This was brilliant! He spent a few moments just bouncing and twisting, feeling the soft puffy skirts bouncing and fluttering with his every move; it was everything he'd dreamed of. Well, almost. He wiggled his toes deep in the tights, the lacy socks, and the plush carpet of his sister's room, and then went looking for shoes.
They had to be high heels of course, and his little stolen moments with the occasional pair had taught him he could walk in them, even if he was still a little wobbly. Luckily in amongst the mass of shoes his sister owned, she'd left behind just the pair he wanted. Again they were a light purple, though perhaps slightly darker than the purple of the dress, the heel wasn't too thin, so he could walk in them easy, and an ankle strap would keep them from falling off; he wasn't sure how you got shoes to stay on with just the toe straps. Not that these were strappy, other than the ankle strap they seemed like normal high heels, whatever that type was called; he had so much to learn. So the back and sides were closed in, and the front covered his toes with no hole in the front for his toes to stick out of, he didn't really like the look of those toe hole ones.
He stepped into them like he'd seen his Mum do, balancing himself on the wardrobe door as they angled his feet, shifting him up and forward. They were a little tighter than he'd expected, probably the tights and socks, but they still fit well. He'd sit down to do up the straps in a moment, but first he took advantage of the extra few inches of height and reached for a box on the top shelf. He set the box down on the bed, walking carefully so as not to trip on the loose straps of the shoes, then sat in the room's only chair - taking a couple of tries before he worked out how to do so in the puffy skirts and petticoats, smoothing everything down under him and lifting the sides a little as he sat. The straps on the shoes were a little trickier than intended, he had to do them up blind due to the puffiness of the dress and petticoats getting in the way.
Turning away from the mirror for now, he reached for the box on the bed and lifted the lid off with a grin. The box was just an old shoebox, but inside was a mass of pink, purple, and blue hair; the wig from Beth's once-off experiment with cosplay. He'd had no idea what character she was meant to be, but had thought she'd looked awesome anyway, and had told her so. It was just what he needed to top his look off. He lifted the wig out carefully, and brushed it and the two ponytail bits with an old brush that Beth had left behind till it looked as good as new. Also in the box were a couple of flimsy half-stocking looking things, that he knew were meant to be put on before the wig; his hair was fairly short, so there wasn't much to keep out of the way, but he picked one up as he wanted to do it right.
He pulled the wig on, which was easy enough as it wasn't too long, but it tickled his eyebrows, so he took it off again, laying it carefully on the bed. There were some odds and ends of make-up he wanted to try, just mascara and lip gloss, and didn't want to mess up the wig. The lip gloss was easy enough, it had a little foam brush sort of thing under the lid for painting it on, and being the artist he was it wasn't too difficult to put it on; he chose a glittery pink from the few available to him, and loved the look and feel of it. The mascara however was nowhere near as easy to apply. It took several tries, a poke in the eye, and a dash to the bathroom for some tissues, before he could get it on without painting his eyelids or cheeks.
Turning back to the wig, he pulled it on again, adjusting the little straps inside it that would keep it on his head; this at least was easier than the bra. He then spent a while with the two pony tails which clipped on, getting one behind and above each ear, having to move them around a bit so they weren't lopsided. But he got them right, and sat looking at himself in the mirror.
He wasn't sure he really looked like a girl, it was all a bit over the top for a start, but he certainly looked girly, which was just what he wanted. With a growing smiled he jumped up, feeling the puffy skirts flounce around him, and nearly skipped over to the full length mirror on the wardrobe door. He spent a while just looking at himself in fascination, he looked girly alright; probably more so than even his sister, and it was all her stuff!
There was no guessing how long he spent in front of the mirror. He flounced, and twirled, blew himself kisses, and even tried a curtsey - though he didn't quite have the balance for that, ending up having to grab onto the bar along the foot of the bed too keep himself upright. But eventually he decided that was enough. Oh he wasn't getting changed, he didn't want to do that till he absolutely had to, but he didn't want to confine himself to this one room either. Deciding to get a drink, he stepped out into the hallway and froze.
He really was home alone, wasn't he? Standing absolutely still so as to keep his skirts from rustling, he strained to listen for anything that meant he wasn't the only one here. But beyond his thudding heart, the house was silent. After a moment he took a deep breathe and continued his trek to the kitchen; he was fine, paranoid, but fine.
He calmed down on the short walk, and got to enjoy the swish of his skirts, and the clip clop sound his heels made on the kitchen tiles. After pouring himself a big glass of juice - Mum didn't like soft drinks at home, but he could have as much juice as he wanted - he grinned at the pink lip gloss left on the glass. He wiped that off with a paper towel quickly, not wanting to risk forgetting to wash it off before his Mum found it. Then his eyes bulged as he stared frozen at the clock on the microwave.
Had it really taken almost two hours to get dressed?
A glance at the dining room clock to double check revealed that yes, it really had. That meant he didn't have as long as he thought, though there was still a few hours till his Mum came home. But, he decided, he'd need to allow at least an hour to get himself ungirlified, if it had taken so long to get dressed. Plus he'd want to do that early enough not to risk being found, and he still had to clean his room as promised, so that meant he had maybe half an hour?
Opting for a quick sandwich for lunch, so as not to waste too much time, he tied his Mum's white cotton apron around his waist to keep his clothes clean, and again got to enjoy the swishing and clicking as he walked about the kitchen fetching bread, butter, and fillings, to make his lunch. Eating didn't take long, and as he started to clean up the little mess he'd made, he realised the obvious solution to more girly time was to just clean his room while dressed; besides, it might make it more fun. He'd just have to keep an eye on the time.
Deciding to keep the apron on, as he really didn't want to ruin the dress, he walked with renewed vigour to his room. He made a quick check in Beth's room, in case there was anything he needed to clean up in there, but there was just what he was wearing, plus the hangers on the bed; that could all wait. Taking another look at himself in the mirror he blew himself another kiss, and this time managed a curtsey without losing his balance. With the apron added to his outfit, he looked like some super girly anime maid, he liked it. So adding a little more lip gloss, after noticing that eating had wiped some of it off, he headed out to start his promised chores.
Over the next hour, things were put away, dirty clothes were taken to the laundry, and - figuring he might as well - the washing machine was started. The floor was cleared, books and magazines were put in shelves, and clean clothes hung up or folded and put away. All in all it was probably the cleanest his room had ever been. David discovered that tidying up was ever so much more fun in a puffy dress and high heels, and before he knew it, he was done; and with time to spare. Wanting to hold onto the feeling a little longer, he fetched the vacuum cleaner from the hallway cupboard, and vacuumed his floors.
After putting his just washed clothes into the dryer, he went to put the vacuum cleaner away, but decided to do the hallway as well. Walking about, skirts swaying and high heels quietly clip clopping on the carpet he'd discovered a rather pleasing feeling. His penis had stiffened again in its panty prison beneath girlish lace and skirts, but this wasn't at all like the feel of quickly jerking off. That was hard and fast, and trying not to make too much noise, but this was soft and slow, warm and cozy; no mess, just niceness. Wanting to keep the feeling as long as possible, he vacuumed the entire house, enjoying the swishing, clip clopping, and occasional little tingles down below as he walked about.
When there was no more to do, he put the vacuum cleaner away, fetched his clothes from the dryer, hung and folded and put them away. There really was nothing more to do, and there was only about an hour before he expected his Mum to come home. He went and had another glass of juice, washing the glass when he was done, and heading back to his sister's room.
He just stood in front of the mirror again, really needing to get undressed, but wanting to savour the last few minutes. With a sigh he sat down, unbuckling the shoes, taking off the wig, piece by piece disassembling himself - or herself? one of those - and putting everything away where he'd found them. Keeping the panties on crossed his mind for a moment, but he dare not risk it. A few minutes later he tromped naked to the bathroom, flat feet feeling strange after hours in heels; he wondered if the slight ache was from wearing high heels or taking them off?
Never mind, he washed his face thoroughly, checking and rechecking that he got every last trace of make-up off, hiding the last remnant of his girly day. He looked like David again, he looked himself over in the bathroom mirror, and wondered who he looked like before, if he only looked like David now. The name Susie popped into his head for some reason, bringing a warmth with it which he savoured for a moment. Yes, he thought, I hope I get to be Susie again soon.
His Mum arrived home less than an hour later to find him sat on the couch playing a game on his play station. "I hope you remembered to clean up, and haven't just been playing that all day." She accused, but looked around and noticed things rearranged here and there as he protested.
"I said I would." He informed her, but she was halfway up the hall already. He paused his game, and went to follow, hoping he hadn't missed anything.
"Wow David!" Georgie exclaimed, "this looks amazing!" She turned to her son as he came up to her, looking a little uncertain. Pulling him into a hug she reassured him "you did great." She pulled away and looked at him with a small teasing smile, "And you vacuumed the whole house, are you sure you didn't hire a maid while I was out?"
"Mum!" He protested, turning away as he felt a blush cross his face.
But his mum just giggled at him, gave him a peck on the cheek - his blush grew - and said "I'm proud of you sweetie. A little alone time does you good, huh?"
"I guess." He agreed, looking at her in hope.
She tussled his hair and wandered off to get changed. "Well, keep this up and you can have Saturdays to yourself from now on then."
He bounced in place, and a little of that squee from earlier crept out again. His Mum laughed, but he didn't care. More Susie Saturdays were going to be awesome!
If you liked this post, you can leave a comment and/or a kudos!
Click the Thumbs Up! button below to leave the author a kudos:
And please, remember to comment, too! Thanks.