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Chapter 20 by Whiteskorpion
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1 Week Later
Kyle is sitting at a table in the cafeteria at school when Alex, Simon and Felix come to him and sit down at the table. Still unsure about his feelings for Alex, Kyle is a bit distant.
Felix: Hey Kyle, we got something for you.
Kyle raises an eyebrow as Felix hands him an envelope full of money.
Simon: We won! $300 for each of us!
Kyle looks at the three of them in shock.
Kyle: 300?!
Alex: Yeah! And that's not all. We also have tickets for the anime convention next week, I wanted to ask if you want to come with me?
Kyle starts to stutter.
Kyle: W-what d-do you mean? Just the two of us what about the others?
Felix: I have plans with the family, unfortunately.
Simon: I have an important appointment.
Alex: Then it would only be the two of us, what do you say?
Kyle thinks for a while and then nods.
Kyle: Alright.
Kyle: Cool. It'll be fun I promise you.
---Timeskip---
Kyle just got home, goes into the living room and lays his head down on the couch, his mom notices and looks at her son with concern.
Mom: Everything ok honey?
Kyle: Mom... I need help...
This surprises her, she walks up to the coach and sits on the floor and puts a hand on her son's back.
Mom: Are there problems at school?
Kyle: No that's not it... I told you I helped someone last week...
Mom: Yes, you did.
Kyle: I was helping Alex and his friends you know the anime club.
Mom: Yeah, I remember.
Kyle: They had a contest where you had to make a calendar and one of their members, the girl, was sick so I helped them out.
Mom: That means?
Kyle: I dressed up as 12 girls from anime, the problem is just it felt good. It felt good to be dressed like a girl. But then there's Alex, he helped me a lot with the cosplays and it felt so good that he took such care of me when he did my makeup. Also, my heart is beating faster and faster now when I see him. And now I've agreed to go to an anime convention with him next week, but I'm so confused...
His mother is silent for a few seconds before saying anything.
Mom: Honey please look at me
Kyle turns his head to the side so she can see his face, which is covered in tears.
Mom: Oh Honey.... Everything is okay with you, there is nothing wrong. I've had a feeling that you love Alex for a long time.
Kyle: Love? Why do you think that?
Mom: Your father, may he not rest in peace. He was an absolute asshole when things like this came up. You may not remember, but you and Alex were very good childhood friends and you always said you wanted to marry him someday.
This shocks Kyle.
Kyle: I did?
Mom: Yes, I always watched how you two got along well, but I always felt that there was something more. Wait a minute.
His mom gets up and pulls out a photo album, she flips through a bit and comes to a section where a young Kyle is wearing his mother's clothes.
Mom: You were so cute back then, you liked to dress in my clothes.
Kyle looks at his mother with concern.
Kyle: Don't you find that strange?
Mom: No honey, that's who you are. I can't hate that, I'm willing to support you completely with everything you do.
Kyle: Also would it be okay if I want to go to this convention as a girl?
Mom: I've never done a cosplay before, but I know how to sew. We're doing a cosplay that will turn his head. But the question is do we go for a cute girl or for a hot one? And which character?
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The Many Tales of Crossdressing.
Crossdressing Stories
Different stories about crossdressing
Updated on Sep 30, 2025
by Onyxdragon100
Created on Nov 30, 2022
by Whiteskorpion
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