Michael's Journey

All new

It seemed like a regular Monday morning in Michael's high school life. He was 14 years old and lived alone with his mother Kay. His father had passed two years ago, while his older brother was already in college. He was getting ready as every morning when he noticed that he ran out of clean underwear. It was not unusual that his clothes were still in the laundry room as his mother was very busy with work, thus occasionally neglecting the laundry. He went downstairs, but he could not find any clean underwear in there either. Out of options he needed to ask mom for help.

"Mom, I can't find any clean underwear. Can you help me real quick."

She looked everywhere, where i already looked, but to no avail.

"Are you sure you don't have any clean underwear in your room?"

"No, I already checked everywhere."

"Alright, let me think. We'll figure this out." She paused. "Okay, I have an idea. Don't call me crazy, but you could wear a pair of my underwear. I have some that are pretty gender neutral."

"No way! I can't be seen like that. You know how cruel kids can be."

"Nobody will even notice. Trust me. You don't even have PE today and in the restroom everybody is just minding their own business," she assured me.

"Didn't you keep some of Dad's old clothes? Maybe there's some underwear in there."

"You know I threw all of his clothes away Michael. I didn't want them in the house anymore."

I need to get out of this somehow. There is no way I'm going to school wearing my moms underwear. Even if nobody sees it, she's gonna bring it up in the future just to embarrass me.

"Can I just skip school today? It's only a day and Mondays are slow anyway," I pleaded.

"No." she said assertively. "You're not going to miss a day of school of something so minor. Plus, do you really think you're the first man to wear women's underwear? You'll get over it."

It was clear that she wouldn't budge. I had to reluctantly accept my fate. She handed me a pair of basic white panty briefs which honestly weren't even that feminine. Maybe Mom is right, and this will be a day like any other. After I took my shower, the moment of truth has arrived. It's just a piece of fabric I tell myself as I slide them up my legs. I quickly put on the rest of my clothes before I could see myself in the mirror with them. In school I was slightly on edge the entire time, but the first classes went by without any incidents.

That's when i had to use the restroom. The only place where I could theoretically get exposed. Just gotta use on of the stalls and I'll be fine, right? Nope, as chance would have it all the stalls were occupied and I had to use the urinal. As if it couldn't get any worse Tyler, the school bully and two of his friends entered the restroom. I was mortified. Before I could finish and pull my pants back up, Tyler already stood by the urinal next to me as he glanced over. He inevitably began laughing.

"Why are you laughing Tyler?" said Jake, one of Tyler's friends.

"You wouldn't believe what this guy next to me is wearing," he said while full on laughing now.

I finished up as quickly as I could and ran out of the restroom with my cheeks turning the darkest shade of red. It won't take long before they tell others to increase my humiliation. Fortunately my last class of the day was without any of them, so I would at least be spared until tomorrow. Back at home I tell mom about what happened.

"I'm gonna be the laughingstock of the school tomorrow! Why couldn't you just let me stay home one day?"

"I know you're upset right now, but it's not all my fault. It won't be as bad as you think. People forget. And in a couple of weeks you'll be able to laugh about it," she said trying to comfort me

"And in the meantime? What do you suggest I do when they make fun of me?"

"Well, there was this one kid in my school who accidentally wore his trunks backwards once. People were laughing, but instead of fixing it he just kept wearing his trunks backwards for the rest of the year. After a while nobody batted an eye anymore."

"Come on! There's no way my situation is even remotely similar," I replied.

"It's all I have Michael. Think about it and decide tomorrow. I'll make sure you got your own underwear ready as well."

I angrily headed towards my room, quickly took of the panties and threw them out of my room. Imagining how embarrassing tomorrow would be kept me up all night. After like 3 hours my alarm went off. Great. Time to get ready. As I got up I noticed a pair of panties on my chair. They were black lace panties with a bow on the front. Clearly more feminine than the pair I wore yesterday. She couldn't expect me to wear these. If somebody saw that, it would get even worse. I decided to hold them in front of my groin area, while looking in the mirror, to see what it would look like on me, as Mom walks in.

"You've got to get ready Michael," she said before turning around and leaving the room.

Shit! She saw that. Guess I've got to go through with it now.

*****

Did I see that right? Is he actually going to wear them? I expected him to ask for a different pair, but maybe he really likes this one. After all it was partly his fault that he didn't have clean underwear. I told him multiple times he needs to toss his dirty clothes in the laundry immediately. While he was showering I looked in his room and they weren't there anymore. That doesn't mean he'll wear them. He probably took a pair of boxer-shorts with him as well. When he came out of the bathroom, and headed downstairs, I asked him how he was feeling. No answer. Whatever it's probably just the nerves.