Michael's Journey

It's time

"Got any plans for the day sweetie?"

"No Mom. Just relaxing you know."

"Well that's great, because I had an idea. What do you say we go out for dinner today?"

"Sure, why not."

"Great! I heard about this new restaurant in the city which has stellar reviews, and I've already made a reservation."

"Sounds great."

"It does yes. There is just this one thing about your wardrobe that we need to discuss beforehand."

"You mean I need to wear a suit or what?"

"Oh no. Quiet the opposite actually." she said with a chuckle.

"Like sweatpants?" I asked confused.

"No. More like opposite gender."

"Wh-Why?" I muttered after freezing for several seconds.

"See Michael, at this restaurant nobody knows us, and you're growing up to be quite a man. So I thought you could dress more feminine so people don't get any wrong ideas about our relationship."

'Quite a man'. Me? I found this to be somewhat ironic given that I was wearing women's underwear and gym shorts in that moment. Hardly anyone would think I'm older than 13 right now.

"You mean people will think we're a couple? That's ridiculous!" I replied. "Plus I don't want people to get 'any wrong ideas' about my gender."

"I wouldn't have expected you to be this insecure after you've already worn women's underwear all week. Including mine!"

"Okay Mom. Before we continue I must insist that from now on we never bring that up again," I said managing to show some confidence.

"Oh I'm sorry sweetie it won't happen again. I was just getting a little frustrated."

"Well me too."

"It's alright Mikey. Maybe I was too pushy."

"It's okay... just out of curiosity. When you said 'more feminine', what did you have in mind?"

 Her eyes lit up when I said that, but she tried her best to stay calm.

"Oh nothing special. Just a dress maybe."

"A dress? I have never worn a dress, and I don't even own a dress either."

"You know I don't mind sharing," she said suggestively.

"Not again Mom."

"No no. I didn't mean it like that. I meant that you could try on an old one which I don't wear anymore."

The thought of wearing a dress certainly piqued my interest, but I could never wear that to a restaurant. People would stare at me. And I've had enough of that in school. She must have noticed my concerns.

"Am I right in assuming that your problem is the 'going out' part and not the 'wearing a dress' part?" she asked.

"Kinda." I replied with my cheeks getting red.

"Okay. Well, I see no reason why you couldn't try on a dress just for the fun of it. Sounds good?"

Still blushing, and slight anxious I agreed. After breakfast she led me upstairs into her bedroom. I don't think I've been in here in a long time. It was huge with a closet covering the entire length of the wall. She opened just one part of it where there were more dresses than I've ever seen before, even at the mall. I was in awe.

"Wow, so many dresses."

"Yeah, I probably should have donated at least half of them by now. But you never know if you're gonna need them one day." she said implying that today was that day. "Okay, you can take all of your clothes off besides your underwear, and put on a bathrobe."

What? I can't be standing there in front of my mother wearing a bathrobe with nothing but my pink panties underneath. I was terrified, but did as she ordered.

"Why did I have to take my socks off Mom?"

"Because you're gonna be wearing one of these," she said as she pulls out a black pair of tights. "And your socks would get in the way."

"I thought we were just trying on dresses. Why do I need tights?"

"Because your legs... in their current state they're not suited for wearing dresses."

"Okay," I gulped.

"Do you know how to put them on?"

"Yeah, I've seen it before."

"Great. Next thing you'll need is this," she says as she pulls out something that looks like a nightie.

"Is this the first dress?" I asked confused.

"No honey. This is a slip. You'll wear it under your dress to protect it from body oils and... perspiration."

"But I just showered an hour ago, and I'm not sweating."

"We'll see about that in an hour," she said with a grin on her face.

"An hour? Really?"

"Earlier you said that you didn't have any plans or did I mishear?"

"No, but..."

"Well then take your bathrobe off, and put these on," she says while handing me the tights and the slip.

I take them from her and head to the bathroom to get changed as she stops me.

"If you're going to the bathroom every time you change, it will take a lot longer. Here, I'll just turn around."

Once she turned around I take off the bathrobe. I was mortified standing there in nothing but my underwear, so i quickly pulled the slip over my head and let it fall down my body while the thin straps rested on my shoulders. At least my underwear was hidden now. Lastly I put on the tights by carefully rolling them over my legs, as to not damage the soft fabric.

"We can start now Mom."

"Not yet," she says after looking me up and down.

"What do you mean?"

"You see, I know you're not used to these clothes, but when you wear something this tight, you have to make sure everything is in the right place."

She was careful to maintain eye contact the entire time so I knew she didn't want to address it directly. Then it dawned on me. I once again forgot to tuck my private parts. Oh god, not in front of Mom. I quickly turned away from her while my cheeks started burning. I thought the tights would flatten the area, but nope. An unambiguous bulge has formed around my groin.

"It's not what it looks like. It's just a crease," I muttered unconvincingly.

"Don't worry honey. It's better that it happened now. You wouldn't want this to happen at the restaurant right?"

"At the restaurant? But you said we were just trying them on! I though I made it clear that I didn't want to go outside dressed like that."