A Lesson for Lester . . . and Me

Chapter 4: moving things along

That second time I had Lester around, I put his hair into a girl's style. The third time (the next day) I started to put lipstick on him. He baulked and protested, "No, no, not that. I won't."

I stood back and gave him a hard frown. "Get out," I snapped.

"What?"

"Go. I can't be bothered with you."

"Kara, hang on . . ."

"You're too much trouble, Lester. Go on, piss off. I'll pass the video on and you can take your chances."

"No, Kara, no, no . . . please. Put the lipstick on me . . . it's all right. . . please . . ."

I was glaring at him. He was shaking, his face a picture of anguish.

"Please, Kara, I'll do whatever you want. I won't protest again . . . I won't, I won't. Please . . ." He was begging me, imploring.

That was how I wanted him to be - pleading and beseeching. I wanted him to be completely compliant. I kept my furious face on but took a big breath, "Very well, Lester. I will give you one more chance, absolutely your last chance."

I had one more session with Lester - hairstyle and lipstick only - before the term holidays started.

I left him alone during the break, except for giving him a lipstick and telling him to practise applying it until our sessions resumed. I could tell that he actually did.

Oh yes, I had him scared all right.

When school resumed, I began having sessions with Lester two or three times a week (at my whim). More make-up, different earrings, hairstyles . . . and I got him to wear some of my old clothes. I started with tops but moved on to shorts and jeans.

Lester was passively cooperative throughout it except for one small plea.

Tentatively he asked, "Kara, can I . . . can I ask you where this is all going . . . what is . . ."

"No," I snarled and he said no more.

I began taking photos of him when he was dressed up. He looked cute. Yes, I'd got it right. Lester had all the appropriate physical attributes; he was going to make a great sissy. Oh, this was fun.

I'd been teaching him how to apply makeup almost from the outset and he was getting quite good at it, but he still couldn't do his hair properly - maybe as it got longer.