Sexy Saturday: I Should Have Known Better (Fiction)

I should have known better.

Leah sat in front of the mirror, brushing her long, beautiful hair. I was envious of it, but not enough to go grow out my own hair. I always succumbed to the newest style, the latest fad. Right now, I wore my hair in an asymmetrical bob, black with blue streaks in it. Hers fell to her waist in gentle, auburn waves. “Should I wear it up, or down?” she asked.

“Up, with some curls hanging down,” I suggested.

“I’m not going to use a curling iron!” That was one reason Leah’s hair was so beautiful. No curling iron, no hair dryer, no harsh chemicals. She was always so gentle with her hair, despite being harsh with the rest of her body.

“You won’t have to. I’ll show you how to do pin curls,” I said.

I helped her put her hair up into a loose chignon, and then took the loose bits and wrapped them around my finger as I tried to remember how I did it during my vintage phase. My fingers brushed against her cheek as I worked, and I shivered.

I should have known better. She was my best friend, after all.

We were going to the opera together that night. Neither of us knew much about music, but we wanted an excuse to dress up. Leah had come over to my place early. She always came to my place to dress up, just as she had done since we were children together. It had been years since she’d stopped hiding who she was, but the habit remained.

“You look beautiful,” I told her.

“I don’t! I’m ugly! My boobs are too small.”

“Your boobs are perfect.” I said, and it was true. They were tiny, gorgeous little mouthfuls. I could just imagine running my thumb over them until they were hard.

“I just wish they’d go up to an A cup,” Leah sighed. “Or a small B. That would be perfect. That’s all I ask.”

“It’ll happen,” I assured her.

“I’ll have to get implants.”

“No you won’t. Besides, you haven’t tried the dress on yet.”

I should have known better. I knew her better than anyone.

No one would guess, looking at her in her underwear, that she hadn’t had surgery yet. It was expensive, and she was still saving up money, but she knew how to tuck and tape. I zipped up the dress for her and watched her face in the mirror.

“Oh, Sharon…” she breathed as she admired herself. It was exactly the reaction I had hoped for when I did the alterations. It was subtle. Just a little bit of fabric taken in here and let out there, to enhance some features and downplay others, and to give her some of the curves that nature had denied her. Surgeons weren’t the only ones who could nip and tuck to make a woman look beautiful.

I’d been there since the beginning, when the little boy next door would come over to play dress-up with me in secret. We’d cried together as puberty had turned both of us into self-loathing messes, had come out to each other first, had somehow reached adulthood intact.

“I wish…” she touched her larynx.

Sometimes she talked about facial feminization surgery too. So much cutting to make her body what it should have been all along. I kept hoping, for her sake, that once the genital reconstruction was performed, the hormonal changes would convince her that she was beautiful.

I should have known better.

“Tsk, tsk. Have more faith in your seamstress,” I said. I pulled out a silk scarf and tied it around her throat in a loose, fluffy bow. I had taken the dress to four different shops before I’d found the right scarf, that matched it perfectly.

Leah loved it. She hugged me tightly, and I hugged her back. That’s when I knew my mistake, and barely stopped myself before making another. I didn’t kiss her, no matter how badly I wanted to.

“I’d better get dressed too,” I said, and turned around to get my own dress. Turned around before she suspected anything was wrong. I’d been there for every step of Leah’s journey, and I intended to be there for all the rest. That meant I couldn’t act on the feelings I’d just discovered. I knew her better than anyone, and I knew why it wouldn’t work. If only I’d known me a little better.

I should have been more on my guard as she transitioned. I should have realized what was likely to happen as she became more and more feminine.

I should have known better than to fall in love with a straight girl.

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About silverdrop

Silverdrop and SilverHubby are a middle aged married opposite-sex couple living in the UK. Silverdrop is gender-queer and SilverHubby is pansexual. We use this blog to talk about our sex lives (especially our fanaticism about anal and pegging), share erotic photos, and offer sex toy reviews. Our [sex isn't always great], mostly because of our health problems, but we always write honestly about it. Our kinks include BDSM, gender-play, pegging, roleplay, fantasy, and lots and lots of anal.

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