The Long Game. Part 1.

A young boy is caught crossdressing.

The long game.

My step sister would intentionally pose provocatively, knowing I was watching.

I was twelve years old when my step sister caught me.  I was in her room, returning her panties. She was older than me, a beautiful 19 and fully a woman. I stood in her room, guiltily holding her red silky panties.

Inside I could feel the tears welling up. I was confused, and had been taking her panties now and then, unsure why, but enjoying pulling them on and posing in front of the big mirror in my mother’s room, when the house was empty.

“I should tell your mommy, you know. It would break her heart, of course,” she said condescendingly. “You wouldn’t care about that though. Why would you care for other people’s feelings, if you think it’s ok to creep around taking their clothes.”

Stephanie was calm, self assured and absolutely confident. She’d grown more confident in the last year or so, as she’d realised the power should held when it came to men.

There had been one or two boys at school, but she’d swiftly dropped them. Her interest lay in older men, who could hardly resist the firm young curves of her exquisite body. She knew how to parade herself to good effect, how to bend over to pick up something on the ground, sure to attract the attention of every male in sight. She knew how to manipulate with a smile, a mock gasp, and a giggle.

I had caught sight of her stepping out of the shower more than once. There had been an occasion when passing her door I’d heard the electric hum of what I knew to be a vibrator, and her heavy breath. Once I had even seen her pleasuring herself, through a partially open door. I’d watched, fascinated, and unseen.

When I think back, I wonder if maybe she’d left that door a little open intentionally. And then there was that horrible moment she walked in unexpectedly as I was retuning her panties after taking them and playing with them in that confused, guilty way.

I’d sneaked silently from my mother’s room to hers, holding the offending garment. As I reached for the draw she stepped from her walk-in closet, where she’d been quietly doing something. I had thought her downstairs, watching something on television.

Well, I was wrong. I expected to be lashed out and berated. She’d done that plenty of times, after all. After she and her father had moved in with my mother, she left no one in any doubt about who ran the house. She controlled her father, as he answered her every whim – and her father controlled everything else.

So, when the harsh slap didn’t come I was surprised. When the shouts and hair pulling failed to materialise, I felt even more confused.

“Do you look nice in them,” she asked.

“I didn’t do anything with them…  I just had them, that’s all!”

“Oh, Michael,” she said softly. “Don’t lie to me. Not unless you want me to tell your mommy.” She drew out the words, leaving no doubt about the menace behind them. Then more softly she continued.

“I think you wore them, and you did so because it feels nice.”


Part 2 is HERE.

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One Reply to “The Long Game. Part 1.”

  1. Got this message in my inbox today and basically ended up wanting to put on panties and just couldn’t resist l had stopped but after your message auntie I love it when you tell me what I should be doing ❤️Linda

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