Thursday, August 12, 2010

My First Time as a Girl

My First Date

I started dating when I was 13. But I’ve always presented as a boy. The other night I went on a date and presented as a girl.

The plan was to meet at her house, change, and then go to a restaurant. She’d be presenting as a boy.

It’d been planned for weeks, and the closer it got the more nervous I became. Several times I thought of canceling, but I pushed myself to go through with it.

I was especially nervous about my razor stubble showing. I’d bought some concealer and decided to try it out before I left my house. It took a while, but I was able to blend it in so it looked pretty natural. It covered most of the evidence that I could grow a beard, but above my upper lip betrayed “the truth” about what was between my legs.

After that, I tried on my outfit and showed off to my Mistress and my Miss. I wanted to drive over as a boy, but my partners convinced me to go over as a girl. Wow. I hadn’t planned on that. Alone, in the car, as a girl. But it made sense. So that’s what I did.

What I Wore

I have lots of slutty, fetish clothes. But “normal” girl clothes, not so much. And it was a casual date, I didn’t want to overdress. So I wore a fuchsia tank top, a pink bra (you could see the straps because it didn’t follow the contours of the tank), tight girl jeans, and pink Chuck high tops.

I also wore a light brown wig (thank you again Fetlife.com; I won the wig in their Christmas giveaway), dangly earrings, and a couple rings.

Before I left my Mistress and Miss gave me some advice. I felt like I was 13 and going on my first date all over again. They couched me on my voice (voice training in 5 minutes?) and I practiced a bit. My Mistress said, “Just don’t say much. It’s easy to be a girl; don’t talk and smile a lot.”

Then my Miss said, “Remember, even if he buys you dinner, it’s your body, you get to decide what happens to it.” I joked, “Not on this date; I think I have to put out.”

All advice received, I psyched myself up and . . . panicked several times before I made it out the front door. There was a neighbor sitting in her car in her driveway. Just, sitting there. What was she doing? Why didn’t she just drive off? Finally, she did, and I took a deep breath and went outside for the first time as a girl.

Driving Over as a Girl

I drove through Washington DC during rush hour, so, a lot of traffic. I stared straight ahead and tried to focus on driving. And of course there was cop right behind me. I had visions of being pulled over and having to talk to the cop. Or having to change a tire in my wig and makeup. Or hitting a car in front of me and having to exchange insurance information.

The reality was a lot more boring. Just a lot of stop and go traffic. Lots of construction. Lots of merging.

But even with all the merging the drive was fairly easy. I seemed to luck out several times; people kept letting me into their lane. Usually I have to fight my way into a merge and I get cut off a lot.

The third time it happened it struck me. The other drivers were seeing me as a girl and being nice to me. From the distance of one car to another I was passing just fine (I dubbed it “car passing”).

I’d anticipated a lot of reactions; violence, mumbled insults, jeers, people (waitresses, cashiers) ignoring me. People being extra nice was not a reaction I had considered.

What She Wore

She dressed in a casual shirt and jeans. She had a buzz cut and used makeup to draw in a mustache and beard line under her chin.We were quite a sight, I’m sure. (Yes there are pictures. No, you can’t see them.)

She, being the boy for the night, drove us to the restaurant. I felt a lot more relaxed being in the car with someone. We chatted about the usual first date stuff; her job, my family, TV shows we liked, shark week. I realized I was doing it; I was living like it was shark week!

She’d picked a restaurant she’d never been to. It was an Italian place just off the highway. Walking up to the door she asked if we should have a cover story, like that we were actors. I thought, now you ask this? I couldn’t really think straight; I just wanted to get inside so I simply smiled.

As we made our way through the parking lot I was worrying about my walk. Was I walking like a boy? Did I need to walk more like a girl? What did that even mean? If I was doing this to be like the real me, should I really be worrying about my mannerisms? Shouldn't I just be me? These questions that are still on my mind.

Dining as a Girl


The smokers outside the bar stared and then looked away. We went in the entrance for the restaurant and stopped just inside the door. It was as if we hadn’t thought about what to do after we got inside. It really was like being 13 all over again and not knowing how to get the hostess’ attention. Finally I suggested we go up to the hostess station.

The hostess didn’t even blink, just smiled and sat us. I sat with my back to the wall; I wanted to to see anything that might be coming at me. Of course, that meant everyone could see my face. I knew my body was passing just fine, it’s my face I was worried about.

The waitress smiled and made some bad jokes. I sensed she had a little banter she'd relied on for years. After she took our drink order I had a chance to size up our fellow diners. How shall I put this? They all looked like they’d had some hard living. And probably had a lot more hard living ahead of them.

And then a family (?) came in. It was five women, so I guessed a mom and her kids. They ranged in age from very young to mid-teens, and then the mom. One of the girls had bangs that stuck straight out and were dyed bright pink. She wore a sleeveless hoodie and bandeau top, with jeans that barely covered her crotch.

Another girl wore a belly shirt, her rather large belly hanging down over her pants. She had blue hair. I thought wow, we picked the right place! We fit right in.

The girl with the pink hair kept staring at me. I thought she was trying to tell if I was a boy. Later, my Mistress said it was probably because I was wearing a wig. “And you have to remember,” she said, “pretty girls get stared at.”

I didn’t do any staring. I just focused on my meal. And kept smiling. The rest of the meal was uneventful. We ate, chatted, got the check, and left. Just like a normal date.

After dinner we went back to her place and I sucked her strap on and she fucked my ass while her boyfriend sat in the next room working on his computer. Just like a normal first date, right?

Later, as we basked in the afterglow of my ass-fucking, my date mentioned she identifies as a gay male. Suddenly I had an overwhelming desire to be her gay boyfriend. I suggested we go out again with her presenting as male and me presenting as her twink boyfriend.

Driving Home as a Boy

I stuffed my wig and bra in my purse for the drive home. I’m sure my makeup was gone by then too. Ahem.

I realized I’d felt more like a girl in the beginning of the evening, but by the end I felt more like a gay boy. I think I was reacting to her male energy. Or maybe it was being naked and getting fucked in the ass. Hard to say.

At the same time, I was really wishing I had a vagina for her to fuck as well. I wish I could have rolled over and had her slide her strapon into my wet pussy. I wanted to stuff my panties into my purse on the way home because they were too wet from my excitement. I wanted to feel the lube sliding done my things.

And with a factory-issued vagina I wouldn’t have to worry about passing as a girl. I’d just “be” a girl.

Or is it really that easy, even for people assigned girl at birth?

I know I wasn’t really happy with how I looked. I wanted to pass better; to have no trace of my maleness showing. I have a big nose and angular face, but there are ways makeup can deal with that.

For years I’ve fantasized about being a woman and it was usually some cute girl I’d seen, or some movie star I wanted to be. This was about being the girl I am; not some idealized version of a girl I’ll never be.

And there are girls with big noses, and angular faces, and even Adam’s apples that stick out a bit “too” much. And girls with mustaches. Presenting in a conventionally cute and sexy way can be a challenge for many girls.

Waking Up as  a (?)

Going out as a girl was a huge high. It was amazing and scary and I told myself I’d never do it again. But by the next afternoon I wanted to go back out as a girl. I wanted everyone to see me that way.

My Mistress and I went shopping and I was excited to get some normal (not fetish) girl clothes so I could go out more often. But at the store I felt overwhelmed by the endless racks and wanted to hide again. It seemed like all the women in the store knew what they were doing except me.

After a while my Mistress helped me go through a rack of shirts, rejecting every single one as inappropriate, ugly, wrong for my body type, etc. And then I thought of my Miss, who hates shopping for clothes because it can be so impossible for a girl to find things that look good and fit right.

And I realized, maybe I’m a lot closer to being a girl than I realized.

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