Confessions of a Sissy: Crossdressing, Feminization, First Time

By Amour

A sissy tells her story to a stranger she meets in a park. This story chronicles the transformation of a nerdy young adult into an insatiable slut.

• Language: English
• Publisher: Amour
• Release date: Jul 28, 2021
• ISBN: 9781005545505

Book preview

Chapter 1

The young man sat quietly on the park bench, with shoulders hunched. He rubbed his palms together every so often, to fight off the July chill. Out of the corner of his eye, he spotted a couple on a nearby bench get up, hold hands and walk away. When he was sure that the young woman was facing away from him, he turned and properly checked her out. She was about 5 feet tall, with a narrow waist, full buttocks and nice, shapely legs.

Lucky bastard he thought as he watched her boyfriend. He noticed that he was wearing a pair of the latest Air Jordan sneakers. Why do some guys have all the luck? he wondered as he continued to admire the girl. He was almost twenty, in fairly good shape, hip about all the trendiest things, yet he was still a virgin, and had never had a girlfriend. The couple he’d been watching walked some distance forward, turned a corner and disappeared from view.

He smelt her perfume first, then heard her. He turned as a woman, straight out of his dreams approached him and asked if she could sit on the bench next to him. Time seemed to stand still, as he stared slack-jawed at her. She had short black hair, pulled back from her face and tied in a pony tail at the back of her head. The lipstick she wore on her full lips was a dark shade of red. Everything he’d seen about her in those few moments seemed flawless. No, he replied in a raspy voice. He cleared his throat and spoke again. Go right ahead, I’m not expecting any company, he said as he gestured towards the bench.

Thanks! she said softly, then sat at the opposite end of the bench.

He nervously squirmed on his side of the bench, swallowed and reached into the front-right pocket of his jeans for his phone. She sat with her knees facing straight ahead, her purse resting lengthwise on her laps, and her hands resting palm-down on either side of the purse. She wore a green, khaki corduroy dress with an above the knee hemline, that showed of her curvy legs and her ankle strap thong sandals. As he went through the old text messages on his phone, he tried his best to covertly check her out. Every time he caught a glimpse of her sexy curves, he felt his heart leap with joy.

Do you mind if I smoke she asked.

Not at all.

She reached into her purse for a lighter and a slim cigarette and lit up. Even the delicate way she held the cigarette only made him want her even more. If only he could work up the courage to engage in a conversation with her.

Well, are you going to do it or not?

Pardon? he asked looking up from his phone.

Are you going to ask me for my number or not?

He gazed at her with a bewildered look on his face. I…​don’t understand.