Hikaru To Hikari: Hikaru starts off the story this way feeling this way about crossdressing, but becomes more comfortable with it as time goes on. By the time of the beach trip, he's become so comfortable with it Aya is surprised to see Hikari already in a swimsuit before she's even had a chance to help him get dressed for the trip. The 100 Girlfriends Who Really, Really, Really, Really, Really Love You: This is one of the few things that can make Rentarou flustered or nervous. They are definitely tighter than my boxers" I joked, trying to make light out of an awkward situation.

In the third-season Modern Family episode "Me? Jealous?", Alex and Haley decide to make up after one of their frequent fights by dressing up Luke as a girl, something they haven't done in a long time. Harry Potter and the Prisoner of Azkaban has a weird case involving a magical creature affected by your thoughts—the Boggart, appearing as your greatest fear, appears as Professor Snape for Neville. To defeat a Boggart, you must force the Boggart into a form that is "funny". When Neville faces the Snape-Boggart, his spell forces it into his grandmother’s clothing.He took the document and signed it without bothering to read it. If he had bothered, he wouldn't have signed it at all. After Alison signed the second document as well, she asked my Mom to read out the terms of the bet. Okay, I won’t tell them but from now on you have to do as I say.” She said. “Fine, just don’t tell them. I will do anything Jody, please.” I said hopelessly. “You better get changed now. Mom’s going to be home soon.” Jody said with a smile, knowing that I was completely under her control. Once he turned 17, we knew our complete control was coming to an end. So instead of reusing the same glue for his breasts, we used one that lasted ten years! That way, he would have to live as a girl during all university and the beginning of his career. His waist now was permanently slimmed, and his ribs would never return to their original position. His feet tendons got stiff from always standing in heels, so we don't think he could ever walk with anything else. Maybe if he slowly decreased the height of his heels, he could walk in normal shoes in a dozen years. Maybe.

DOUBLE K has Kamina forcing Simon into the role of the Dirty Harriet to bust solicitors. He's done this more times than he really should, according to Lord Genome. Oh hi" Em's mom said. I was unsure what to do. I sunk underneath the blanket, making sure only my head was visible. Em's mom came over to shake my hand. "Mom this is my friend from school, he walked me home after work" Em said. I proceeded to reach my hand out to shake Em's mom's hand. "Why is he wearing my favorite PJ's!!!" Em's sister shouted. I looked down, realizing that when I went to shake hands, the blanked slid down revealing the pajamas. I was frozen in embarrassment. As my wife I expect you to be wearing feminine girls panties from now on!” She said, adding. “All the time just like a real girl!” She smiled at me. “And whenever your home I expect you to be dressed like a sissy in a dress or skirt and blouse and a bra and panties and a slip, nylons and high heels!” She said, her stern voice not leaving any room for discussion.I looked at it and had no idea what to do. I started to slide it over my head, but realized that there were shorts sewn into the dress. Since you already took a shower a couple of hours ago, we will just get you dressed and do your hair and make-up."

I was nervous to speak at first but I finally told her that I kept having an urge to dress up as a girl and feel what its like. I could tell she was pretty surprised by what I said. After some minutes of silence, she asked me if I was joking? But I told her it was the truth.If you behave yourself over the next 9 months till you are 16, then the reluctance clause will disappear and the failing of total obedience will only result into the hormone treatment if I decide it. As part of the document you have given permission for the girls to glue breast forms onto your chest using any non-permanent glue that must last for at least a full year before needing to be replaced. What this means is that the breasts will remain fixed at least until 3 months after you're 16. If the hormones have started then they will not be replaced, but if not, then they will be. But before he had a chance to answer, we entered the front room. Our respective fathers stared in open-mouthed amazement. Something seemed to go pop in my head as I shyly looked at him, feeling an inner excitement. "I think the name Alice is very sweet, don't you?" I knew that I had spoken in a higher voice, but just felt that I had to. When Persona 5 was given an Updated Re Release, one of the minor changes was making it so the two Camp Gay men Ryuji encounters in Shinjuku do this to him instead of hitting on him and sexually harassing him.

Gender Flipped in Ouran High School Host Club when the boys are quite happy to dress up Haruhi (in men's clothing, making it this trope, as well as women's).

Examples:

She made me get up and as we walked towards the door, I begged her not to take me and meet her friends. She said she knew I would be scared for the first time to go out in public dressed as a girl but this would be a great chance for me to finally feel like a girl . I understood what was trying to say and agreed to go out.