She Made Him Her Pretty Teenage Step-Sister

She Made Him Her Pretty Teenage Step-Sister

Written by Karen Jensen – Illustrations by ENEG

She-Made-Him-Her-Pretty-Teenage-Step-Sister-00a It had been a tough year for Norman Malone. His mother had died when he was an infant and his father had just remarried the beginning of last year. He had moved to another town to live with his new wife and left Norman with friends to finish the school year. When summer arrived and school let out, Norman also moved, leaving his friends behind. He was there just a few weeks when his father suddenly died of a massive heart attack.

Now he was living with his step mother and step sister Andrea, who at 17 was the same age as Norman. He felt like he was living with two strangers. His stepmother was nice enough to him, and tried to make him feel welcome in her home, but Andrea made no pretense of liking him at all and looked upon him as an intruder in her life. She went out of her way to make his life miserable and it seemed that no matter what Norman did for her, it was not enough.

It was a couple of weeks after the funeral. His step mother had gone away for the weekend to try to get over her grief. Norman was downtown having a soda, also trying to forget his sorrow. He felt a tap on his shoulder and looked up to see Lois, his sister’s friend, a girl Norman developed a crush on the first time he met her.

“Hi, Norman. I’m really sorry about your dad. Is there anything I can do for you?”

“Oh, uh, no thanks Lois. I’m just drowning my sorrow in a soda. Can I buy you one?”

Lois sat down and they talked for awhile.

“Look, Norman, no one is home at my house. My folks went away for the weekend. Would you like to come over and go swimming with me?”

“Yeah, I’d like that.”

It was a short walk to her house. Norman’s spirits picked up immediately and he considered himself to be very lucky to be spending the afternoon with a beautiful girl like Lois. “Just go into the bathroom and get undressed. I’ll get you a swim suit and hand it to you through the door.”

Norman was really excited and in no time at all was standing there naked. Spending time alone with Lois was more than he dared dream.

“I have a suit for you, give me your clothes and I’ll hang them up while your changing.” She took his clothes, and gave him what she had, and went to put away his clothes.

After he did as he was told and she handed him the bathing suit. He was stunned when he realized she had given him a girl’s bathing suit. It was a one piece purple bathing suit with little pink flowers on it.

“Hey, I can’t wear this. Don’t you have a boy’s suit?”

“None that are clean. Who’s gonna see you besides me. I think you’ll look cute. Why don’t you try it on and see. I promise I won’t tell anyone” Norman was at a loss. He really wanted to be with Lois and she seemed pretty anxious for him to put on the bathing suit. He was embarrassed at the prospect of having to wear a girls swim suit, but he knew he couldn’t very well walk around naked.

“Hey Norman, what’s taking so long. Come on out. I promise I won’t laugh.”

Reluctantly he slipped on the girl’s swimsuit and shyly stepped out of the bathroom.

She-Made-Him-Her-Pretty-Teenage-Step-Sister-04 “Wow, you do look really cute”, Lois exclaimed. “Let me give you some finishing touches, so you’ll look better in it. I am going to put some water proof eye makeup on you and this bathing cap. This way if anyone does come over, they will think you are a girl.

If the neighbors see you, they won’t think I had a boy come over alone and tell my parents.”

She put her water proof mascara and eyeliner on his eyes, and a touch of eye shadow on his eyelids. She adjusted his bathing cap, and then quickly applied a coat of light red glossy lip stick to his lips, making him look like a real attractive teenage girl with sensual kissable lips. She inserted a pair of foam shaped pads into the top of his swimsuit and adjusted the cups so they looked natural in appearance on him if he were a real girl.

Norman was shocked at her moves and her suggestion but offered no resistance. What she said made some sense to him, and wearing the suit wasn’t so bad after all. In fact, though he wouldn’t admit it, he kind of liked the way the it felt.

The two of them played and swam, and Norman was less aware of how he was dressed. He winced when she started calling him Nancy, but as she explained, if anyone did come over, they would hardly think he was a girl with a name like Norman. They were enjoying themselves so much that they were unaware of the passing of time when they heard the gate open and looked up to see Andrea staring at them.

“Who is your new friend, Lois? I don’t believe I have met a girl like her before. Why it looks like my step brother Norman in drag”, she laughed.

Norman was mortified. If Andrea told his stepmother about him wearing girl’s clothing, she might throw him out of the house. And then where would he go?

“Look, Andrea, I can explain.”

Ready to start your training?

Submit your application today!


rosemary anne

I’m one of your loving, grateful sissies…..You have given me the gift of knowing I’m not alone.

Notify of
oldest most voted
Inline Feedbacks
View all comments