How Looking Down At My Cock Made Me Fall In Love With Being A Girl

by Lana Louise

Her name was Layla. She was 25. Blond. Fourth grade teacher. Tiny, perfect tits. I swear I’m not making this up. There’s six of us in this warm, soft playroom surrounded by fresh baked cookies, pillows, blankets, dildos, Hitachis, gloves, condoms, and giggles. A nearly empty bottle of Jameson reflects the firelight. It’s my first real sex party and Layla, this lithe, hot little thing with hand-dyed red streaks in her hair (did I mention she was a school teacher?) is untying her corset and shyly asking if maybe…Um… Would anyone would want to try doing her with the strap on? Are you fucking kidding me?

My entire goal for the evening had been to avoid crapping myself in front of the hot lesbians. Seriously. I get awkward as hell around females. The first time I ever told someone I was bi was in the seventh grade, so the wanting girls thing is not new for me. Lusting for girls. Fantasizing. Awkwardly hooking up with one or two when I was hammered enough to make a move. Watching cheesy, fake nails, straight-guy type lesbian porn and masturbating furiously. The actually-managing-to-have-real-live-contact-with-boobs thing? Yowza; not so much. The reasons for this are probably a whole different essay, but I’ve just always had an easier time with boys (hint: boys are sluts). So when a terrifyingly hot, older coworker with a job at a sex institute for some inexplicable but blessed reason decided that I was her next prey, lets just say I did a lot of staring in the mirror and pinching myself.

As the women suited me up to give Layla what she asked for, I found myself startled by how powerful I suddenly felt. I’d never worn a strap on before and it felt better than I ever imagined.

I’ve had a bit of a hard time with the whole gender situation. I still remember the first summer that my mom explained to me why my brother was allowed to run around with his shirt off but I wasn’t. I’m big into board sports, angry music, and a whole lot of other guy-dominated type things. I used to hate being a girl, and that feeling has always come and gone. I knew relatively early that I’m not legitimately transgendered; it’s more like the boobs just piss me off sometimes. I never understood that whole “getting your period is beautiful and important” nonsense. My stomach hurts and my swim times are slowing down! Fuck you! Sometimes clothes are fun, I guess? [looks skeptical] As I got older I became a lot more comfortable in my body, and I got over a lot of the initial shock. I learned to flirt and tease, and to be more at ease in friendships with females, but a lot still lingered. I got in all sorts of “toughness” contests with everyone around me; I always felt the need to prove something. I hated feeling like I stood out at a jump park, like every trick I tried represented my whole stupid gender. I felt as though I had a bit harder of a time enjoying sex than my partners (sometimes I LOVED it, other times it just didn’t feel that great). But, and maybe I didn’t figure this out until I was eight inches deep in Layla (mmm….), one of the biggest reasons I was always jealous of guys was that they got to hook up with girls. Even when I was fucking a guy, on some strange level I was always kinda jealous of him. He got to run his hands along breasts and hips, and while sometimes guy muscles make me shiver with delight, other times they just don’t do it for me. I could never give up guys all together; I really do love the silly bastards. I just always felt sort of torn between genders inside.

A good friend of mine asked me afterwards if it felt as though I had gained some sort of strength or masculinity from the experience. “No,” I replied instantly. “It felt like finally getting to use something that’s been there all along.” As my mouth formed the words I realized how true it was, and how huge this new feeling had become. When I was fucking Layla, I knew exactly what I was doing. It felt amazing. I was strong, I was hardcore and masculine and badass and all the things I’ve always gotten shit for, and everyone in the room thought I was hotter because of it, not less desirable. Real lesbians, of course, figured this out a long time ago. But still. As girls, we get to have it both ways! I can do whatever I want! Knowing that I could play with my male side sexually made me about a thousand times happier in my feminine skin also. The next time I was with a guy I practically attacked him.

Every time I sleep with a guy, it makes me want girls a little bit and vice versa. Many poly people have described needing different sorts of things from different people, but for me there’s a little bit more than that. I walk a little taller around the rest of my life when I remember Layla’s orgasm. How many guys had ever lived out that kind of fantasy? I had been a woman, I’d been a man. I could fuck, get fucked, and stomp a 360. I was the hottest thing ever. Anyone who didn’t like it could go crawl in a hole.

So looking down at this massive silicone jutting out from my hips, still wet from the girl I had pleased, I couldn’t stop grabbing it and grinning.

“I have a dick!” I said softly, forgetting that everyone was watching me.

The girls burst out in loud laughter. My coworker looked at me with mischievous eyes and a massive smile. “And it’s big! And black! And it vibrates!!”

I looked back at her, eyes wide, and shook my new cock back and forth.

And I didn’t even shit my pants.