Caught In The Act [Private]
 

Leo Marquez lived for moments like these, even if they made him so nervous it probably shaved a month off his life every time the moments came along.

A couple minutes ago, Leo had seemed quite engrossed in a very big book, barely even noticing when his mom had told him she needed to go out for a while and run some errands. Still, he'd acknowledged he'd heard her, promised he'd hold down the fort while she was gone, and gone back to his book in the way that always suggested correctly she'd come back to find him still there, still reading.

Typically this wasn't the case at all, but Leo had worked hard to maintain the illusion, anyway.

His mom was one of the best parents a shy, intellectual boy like Leo could ask for. Being a dainty-looking and sadly rather pretty instead of handsome, Leo's long blonde hair and deep green eyes and delicate frame had gotten him a fair number of compliments from girls, but also far more than his fair share of teasing and the occasional outright bullying. It wasn't much of a surprise someone like that might end up with their mom as one of the only friends they had in day-to-day life.

Having a good brain and a good understanding of his mom meant Leo had a lot of freedom when "errands" came up. She was never gone so long she missed dinner, but his mom would be otherwise occupied for a good two hours at least in Leo's reckoning, more than enough time to himself for Leo to indulge a guilty pleasure or two.

First it was up to his room, where Leo got rid of his pants and boxers, pulling out a secret package in his closet and fishing out a few supplies. After a minute or two, Leo blushed and sighed contentedly as he stood up, now wearing a diaper...odd enough already, but even more strangely, it was a pink Disney Princess diaper with blue highlights on it, something no boy in their right mind would be caught dead anywhere near!

Taking off the rest of his clothes, Leo went into his Mom's room, guiltily starting to poke around in her closet for a dress to wear.

He felt bad going through his mom's things and wearing her dresses when she wasn't at home, but this time to himself was the only time he could wear what he really wanted to...and get the wonderful happy feeling that doing this gave him.

With two hours to kill, he'd probably put on a couple new dresses he hadn't tried yet, but first Leo immediately put on one of his mom's old pink dresses, one that actually fit him pretty well and went perfectly with the color of his favorite kind of diaper.

Sitting at a red light Renee was seconds away from beating herself unconscious on the steering wheel of her little Audi 4-door. The traffic in town was terrible, and at this rate she was never going to be able to make it to her client's perspective house. Renee was a successful real-estate agent in business for herself and she was now almost late for showing the house her clients. She looked at the clock on her dash; she had no hope to make it. Renee frowned, thinking of her son stuck at home alone... she was almost his only friend. Suddenly she had an idea.

Three phone calls later she had a co-worker on her way to show the house, her clients aware of the new plan, and best of all a pizza waiting to be picked up. She thought to call Leo, but she wanted to surprise him.

Leo, completely oblivious to his mother's decision to come home and surprise him, was just finishing tying a pretty pink ribbon into his hair in front of the mirror. He blushed, smiling at his reflection; hair bows were so nice, but nobody wore them anymore except little girls. It was such a shame.

As he often was, Leo was tempted to experiment just a little with his mom's makeup, but he knew better than that. No makeup, no nails, not ever. Leo never wanted a careless clean-up to give him away and end his little moments forever. Leo had been able to play dress-up by himself the last two years or so by adhering to very careful rules to make sure he wouldn't get caught.

Unfortunately, Leo had gone without playing dress-up so long, he'd forgotten one of the more critical rules to playing was to make absolutely sure he'd closed the garage door before he went upstairs, so he could hear when a car was about to pull in.

Renee picked up the pizzas on her way back home. The traffic was just as bad, but somehow she couldn't help but smile. She and her son would have a chance to bond over pizza and a movie. Soon though she was rewarded with the sight of her driveway. Strangely the garage door was up, as much as she hoped Leo would find steady friends, she hoped he hadn't left the house. "I guess it wouldn't hurt if he had" she thought to herself, as she pulled into the garage.
Renee walked inside without shutting the garage door as she was preoccupied with finding out where her son was. She set the pizza on the counter and walked upstairs to his room. "Hey! I got us some pizza why don't w..." she began as she opened the door "What are you doing with my dress, young man?" she asked sternly, but there was not a hint of anger in her voice.

The bottom dropped out of Leo's stomach.

Oh, SHIT.

Leo just stood there like a deer caught in the headlights, staring at his mother in shock. He didn't even realize he was starting to cry already.

He'd been so careful all this time not to let anyone ever find out or see him like this, and now one little slip-up he hadn't seen coming had brought it all crashing down.

Leo tried to run through one excuse after another, but couldn't even manage to get the first little peep out of any of them. All he could do was turn red and look at the floor in shame, his vision blurred by hot tears.

Renee sighed, "It's okay sweetheart" she said walking over to him and put an arm around him. "Don't feel bad hon, I wouldn't have thought you liked to cross-dress, but it's not something to be ashamed of.... and I'm NOT mad at you." She slowly rubbed her sons back. "Why don't you just give me my dress and get changed? We'll talk about it over some pizza"

"O-OK..." Leo sniffed, still feeling like dirt. He grew more worried as he realized getting changed in front of his mom was going to show off the one secret he had left.

"C-Can I change in private, though?" He asked weakly. His mom had already seen him in a pretty pink dress, he didn't want her to see what was under it, too!

"Okay sweetie, just hand me the dress and I get out of your hair." Renee said still standing in front of him

"I-I will, j-just..." Leo mumbled, stepping back.

There was one trouble to concealing what he was wearing; cutesy as they were, the diapers Leo wore were also pretty thick and tended to crinkle a little with his movements. As such, the quick step back he made was rather awkward-looking due to the thickness, and it produced a loud crinkling sound under the dress and a guilty expression confirming that the noise was, in fact, important and not something Leo had wanted his mom to hear.

Leo wondered if he had sinned horribly in some past life to get all of this happening to him now.

Renee heard the diaper Leo wore and pulled up the dress. "What is this???" she shouted "Why are you wearing a diaper???" she asked, bewildered. She ripped the dress off leaving him standing there with nothing on but the pink diaper.