Seven Days With Stepmum - Chapter 4 (Patreon)

In fact that was exactly what she had in mind with him.

“I can’t leave you home alone Charlie, what kind of guardian would I be?”

Charlie tensed up. “B…But I’m an adult I can be home alone, I look ridiculous you can’t make me please.”

Anna looked down at the begging boy; it was a rather pathetic display.

She sighed. “Fine give me a moment then, would you I’ll be right back.”

When she left the room Charlie took the opportunity to examine himself in the mirror. He did look a sight with his lanky hairy legs sticking out from under the dress. It really didn’t go well together it made the whole look even stranger. He cringed when he realised he was picturing the problem being his leg hair and not the fact that a young man his age had been forced into a girly dress. That was the true problem focus on that, he told himself.

Anna soon returned after making a quick phone call from the living room.

“Alright I sorted you out, Denise will take you.”

“Huh, who’s Denise?” He asked perplexedly

“She’s my next door neighbour; if you’re adamant on not going with me then she will look after you.”

Charlie gasped. “Wait that’s just as bad, no one else can see me like this.”

He was really starting to get on Anna’s patience now. “She’s a kindly older woman and you will get along just fine, she’s had plenty of experience babysitting fussy children so you won’t be a problem for her.”

“Come on Anna you can’t be serious right now.” He whined

“CHARLIE.” Anna raised her voice. “Do you want me to call your father right now? Because I will have no problem telling him about your behaviour and the reason being you don’t want to be seen out in public in your pretty dress.”

That made Charlie squirm, he desperately didn’t want anyone else he knew finding out about this especially his father. Surely spending a short time next door with a stranger was the lesser of two evils.

“Alright fine I suppose, just don’t say anything to him please.” He reasoned.

Anna’s cheerful smile returned and she slid on the sandals from before and buckled them over his feet. It looked a bit unusual wearing them with socks but she didn’t want his feet getting cold it was a bit nippy outside. The thin dress probably wasn’t the most suitable thing to put him in but there weren’t a lot of suitable options. With both parties dressed and ready they walked together hand in hand out onto the front yard.

Charlie turned frantically hoping that no one would be out driving passed and see him dressed this way. Thankfully he finally managed a small stroke of luck when they seemed to be the only ones out at the time. His hopes were dashed when he saw an old woman standing on her porch watching them with keen interest. Anna waved as she walked over to her, Charlie quickly realising that this was the woman he was being pawned off onto. She was going to always see him dressed this way but it didn’t make him feel any less uncomftable or exposed.

“Denise thank you so much for this.” Anna said giving the older woman a hug.

“Oh it’s no problem at all, now this must be Charlie.” She said giving him a good glance over.

“That’s a very pretty dress you’re wearing sweetheart.”

He didn’t know what to say, he was trying to rack his brain to think if this woman really thought he was a girl or just a boy in a dress. There was no telling though surely, his hairy legs and stocky frame plus a lack of any breasts she surely had to know.

“Charlie it’s rude not to say anything when someone speaks to you.” Anna said interrupting his thoughts.

“Sorry, ummm thank you Denise.” He quickly replied.

“Please, call me Nana, Denise sounds much too formal.” She responded.

Charlie looked at her; he could see both women watching him expectantly.

“Oh right, thank you Nana?”

That seemed to be good enough for them, Denise smiled and took Charlies hand.

“Don’t worry Anna he will be in good hands.” She said giving his a squeeze.

Anna smiled. “I know Denise, you were always so good with Dani, just make sure he behaves himself.”

She walked over toward her car and turned back before stepping in. “Oh and Charlie make sure you tell Denise if you need to use the potty, he’s had a bit of trouble since he got here.”

Charlie blushed crimson, what the hell she made it sound like he was some kind of potty training toddler. He had one close call it wasn’t like it happened regularly; he couldn’t even dispute it because Anna had already shut her door. She waved goodbye before driving off down the street.

Denise turned her attention back to Charlie. “Alright, let’s get you inside it’s not really the best weather for your outfit today.”

“My clothes are all in the wash.” He explained.

“What all of them? You didn’t have a thicker dress or cute jacket you could wear over the top?”

“No Anna picked this, I don’t wear girls clothes.”

He followed her inside and down a rather quaint looking hallway adorned with vintage décor. She still adamantly held onto his hand refusing to let it go.

“Oh Anna has been dressing you, well isn’t that sweet, I think it’s nice you guys have such a loving relationship, she was always a lovely mother.”

Charlie was ready to explain further, annoyed that she seemed to be glancing over the fact he was a guy and wouldn’t wear these clothes normally. But he was already being pushed inside the bathroom.

“Why are we going in here, I don’t have to go?”

Denise smiled. “Anna made it clear that you seem to be having trouble with the loo.”

She pulled up his dress before he could stop her or say anything, exposing his willy to the room.

“Where are your training panties Charlie?” She asked sincerely.

“What the hell, I don’t wear them let go.” He demanded, pulling his dress down.

“Not training panties? Then where is your diaper, you can’t be walking around nude.”

Charlie stepped back from Denise before she could grab his dress again. “I don’t wear diapers either I’m an adult, I’m a boy can’t you tell that?” He said in a rather nasty tone.

“I’m well aware of that Charlie, its ok to like girly things I’ve never been one to judge.” She sighed.

“Well why we’re in here we may as well sort that out before we deal with your underwear situation.”

She gestured towards his legs before she retrieved a razor and some cream from the basin cabinet.

“You’re not shaving me.” He told her bluntly.

Denise shook her head. “I don’t put up with this sort of behaviour on my household Charlie, Anna will want a full report when she comes back, and do you want me to tell her you’ve been a good girl or a bad boy?”

He gulped, this was bullshit did he really have to go through with this or risk it all getting back to his dad.

“Whatever fine.”

Denise stared straight at him. “That isn’t what I asked was it Charlie.”

He looked back at her expectantly.

“I said…. Will you be a Good girl or bad boy?”

This was so awkward, he paused he was going to tell her he would be a good boy. But he knew that wouldn’t be good enough and pissing off this woman any further wasn’t going to do him any good. It’s only leg hair it would grow back, he would just stay in jeans and summer was far away anyway no one would find out.

“I’ll be a good girl.” He said in a hushed whisper.

It was satisfactory enough for Denise who beamed at his submission.

“Good, that’s much better, now stand there it hopefully won’t take me too long.”

It actually did take a rather long time removing all his hair. There was no clock or any way of knowing how long he stood there but it would likely have been almost half an hour. The whole time he was unmoving as she made sure not to miss a single patch of hair. It got to a point where his dress was in the way and he was made to completely unclothe himself in front of her. He didn’t resist, it was pointless this way it was better to get it all over with quickly. She checked his body over removing the small patch of hair on his armpits, the rest of his body was mostly hairless. But finally she rested over his genitals removing the fair thin hair from around his groin and scrotum. He didn’t dare flinch as the razer drew dangerously closer to his most sensitive areas. It was such a surreal feeling having her handle his manhood as she shaved him then again when she washed him over with a cloth.

Finally the humiliating ordeal was over and he stood completely hairless neck down, suddenly looking more like a girl than before.