When I Was a Girl
By: Guy New York
Tags: Short Story, Sexuality, Gender, Erotica, Fiction

“You don’t have to tell me,” she says. “But if you do, then I’ll tell you about being a boy.”

I sit up in bed, my wine glass nearly empty on the side table. I swallow the rest as I wonder where the hell that fear is coming from. It was a simple question, and I know the answer. Most people probably have fantasies like this, so what’s the big deal? Why all the fear?

“I don’t know why it makes me nervous,” I tell her.

“It makes me nervous too. Like I’m a fake or a weirdo, or I have some issue I’ve never examined. It’s scary. But scary is okay.”

“Sometimes it’s someone I knew, but most often not,” I begin. She sits up and covers her feet with the blanket. I continue.

“Most often it’s me, but not me. It’s some version of me that’s young and pretty with a body that’s almost familiar. I don’t have the nerve to picture her–me I should say–any other way. Besides, it’s a fantasy, right? I can be pretty if I want to be.”

“You’d be beautiful,” she says, touching my arm with ease. I blush but keep going because once I stop I might not start again.

“I suppose it varies from time to time, but it’s always someone a little older who wants me more than I can understand. He’s arrogant but cautious, and usually, he has a girlfriend as well. Maybe she’s my sister or just an older friend; it doesn’t matter. But they tease me and joke about how inexperienced I am as I struggle to convince them I know something.”

I take a deep breath and find myself holding her hand.

“And then they start pushing and teasing. She asks him if he likes me and they begin talking about me like I’m not there. Somewhere in the middle, she grabs my hand and puts it on his cock. ‘He does like you,’ she teases as she moves behind me. I don’t realize that she’s holding me and I can’t move until my shirt is gone and he’s feeling me up. She grips me tightly as his hands move everywhere, touching me as his cock springs free from his jeans.”

“It’s super hot,” she whispers, nodding at me to continue. My desire is overcoming my fear, but it’s still a potent combination of the two.

“Then it’s a blur because by the time the fantasy has gotten that far I’m so ready to come I can barely hold back. I take it slowly, focusing on all the little creepy fucking details until I’m sucking his cock as he’s pulling my ass open and fingering my pussy. It’s a blur as she pins me to the bed and rubs him against me, laughing at me as she tells me he’s going to fuck me.

“Half of me wants to beg him to stop and the other half not to, and then he’s fucking me, and all I can feel is small and consumed and overwhelmed by the feeling of being full. Somehow I can picture it too. I know I’ve never been fucked like that, but I can feel him inside me in parts I don’t have, and that’s the end of it. I cry out as he fucks me, uses me really, and then he’s coming and so am I and I instantly come back to my body the way it is now.

“I cover myself quickly because I’m embarrassed but still giddy. And as I lie there afterward, sometimes he’s there with me, touching my face and gently tracing his fingers over the lips of my pussy and through my pubic hair. His breath is warm, and my body is sticky and sweaty and aching for something I can never have.”

I take a sip of my empty wine glass, annoyed that I left the bottle in the other room. Without a word, she hands me her drink, and I wet my lips before I swallow. It takes me a while to realize she’s still holding my hand. I kiss her fingers and see that there’s a tear in her eyes.

“You big beautiful person,” she says, pulling me in for a kiss. “That was super hot and sexy and creepy and honest. And I love you.”

“Are you sure?” I ask, knowing the answer but wanting to hear it all the same.

“Of course,” she says taking a deep breath of her own. “But since I promised…”

“You don’t have to,” I say, pulling her closer. She nods and wipes her face, and then she turns to me once again, and all I can do is listen with as much kindness as she did.

“So,” she begins. “It all starts with when I was a boy…”