Chapters tagged crossdress

by hush1223

Chapter 1

\*All characters are 18+\* "Fairfield Dance Costume Contest! Next Friday 6-9 p.m. Best Costume Wins a Grand Prize of $5,000 AND ONE YEAR of FREE TUITION at Fairfield Community College! Winner voted on BY the students!" Melissa looked at the flyer she picked out of her son,...

by hush1223

Chapter 2

Walking along the train tracks, Luke burped as he crushed the empty can of Budweisser and threw it over the small bridge leading out into the highway, not caring if that empty can would cause any damage to the cars driving below. He was with his two friends, Mark and Jacob, one o...

by hush1223

Chapter 4

Melissa sat patiently with her legs crossed on her couch facing the door. It was now 2:30 a.m. and her son still wasn't home. She was furious with him. Earlier before hitting the floor at work she received a call from a concerned parent of a girl at his school named Rebecca. Appa...

by hush1223

Chapter 5

"Ugh," Luke groaned as he was coming to. The sun was shining through his window and into his eyes, as the headache took over him. "I drank way too much last night," Luke thought. "How'd I even get home?" Luke rolled out of bed and almost tripped over himself when he noticed the u...

by hush1223

Chapter 6

"Oh my god, this is going to be so great," Melissa thought to herself. As soon as she heard the shower start running she ran into Luke's bedroom and quickly laid out the outfit she had gotten him. She had told Lisa all about the phone call she had received about what Luke did to...

by hush1223

Chapter 7

"No way bitch!" Luke screamed banging on his locked bedroom door. "I'm not wearing this shit." "Yes, you are young man... Or should I say young woman. You are going to learn how to behave and what better way to start than by doing some housework. Of course you can't do housework...

by hush1223

Chapter 8

Her son ran out of his bedroom like shot out of a cannon and she couldn't believe how absolutely girly her son looked from behind. The dress was even shorter than she thought and barely covered the top of the thong she made him wear. His butt and legs looked particularly girly be...

by hush1223

Chapter 9

"This is exhausting," Luke said to himself as he was dusting the top of the cupboards in his kitchen, standing on his, "itsy bitsy tippy toes," as his mother called them, knowing full well his pantied bottom was on full display. This was utterly humiliating. And to think he was g...

by hush1223

Chapter 10

"Okay, Lucy. Why don't you walk to the end of the hall one more time for me. And really swing your hips this time," Lisa said. She watched as little Lucy tried her very best to swing her hips like the bimbo slut Lisa had wanted to turn her into. She wasn't sure how far Melissa wa...

by hush1223

Chapter 11

Walking through the entrance of Victoria's Secret, Luke was already feeling humiliated. The butt plug felt heavy in his bum and he felt so exposed in the short skirt walking through the mall. The skirt was so short that it just barely covered the white of his panties. Wait, not h...

by hush1223

Chapter 12

Walking back into his home, with several bags in hand, Luke was drained. Spending all day at the mall with Aunt Lisa, putting on his best girly act was tiring. "Oh my gosh, honey. We completely forgot to get your nails done! Don't worry, we can do that now while we wait for your...

by hush1223

Chapter 13

"Gosh he's really getting into it, isn't she?" Melissa asked. "Yes, SHE is! Please think of her as your daughter, Melissa. It'll make it easier for you to deal with," Lisa said. She could tell her best friend was struggling with how to feel about all this. She saw the shocked lo...

by hush1223

Chapter 14

Melissa lay restless in bed thinking of her son-turned-daughter sleeping in the room opposite the adjoining bathroom. Her and Lisa had tucked the little one into bed the night before without a peep of protest from him. It's odd that he's taking it so well, she thought, but then i...