Gender Bent

I keep glancing at my watch. It feels like it's been 4:59 pm for twenty minutes now. It's Friday night and the forms I have yet to enter into my company's enormous database will keep until Monday. I just want to go already! I've got plans tonight and I'm already feeling pretty stoked about it.

Finally! Five rolls around and I gather up my things from my small cubicle. Straight out of school I landed this job, and while I've been working it for a year and the pay is alright, it's definitely a beige sort of employment. I need color in my life, and that's what I save my nights for. Pulling on my black jacket and shouldering my messenger bag, I do a quick check at my desk to make sure I didn't forget anything. What's the rhyme? Spectacles, testicles, wallet and watch? Well, I've got them all on me, so I feel ready to check out.

The sensor beeps as I press my ID card up against it, and as I step out into the springtime air I feel invigorated after a long and dull day. A few of my friends are smoking outside already and I chat with them, as always refusing their offer to start up a bad habit. I get ribbed for it but it's all in good fun, and I'm invited to go out drinking with them. Usually I'd cheerfully agree, and we'd probably head out to somewhere with pretty girls and hot wings. Maybe even both. But tonight is my special night, and I have to turn them down and get home so I can get ready.

Back at my studio apartment I deal with my Tupperware from lunch, stuffing it into the dishwasher, same as my water bottle. My work clothes are stripped off and I take a refreshing shower. By now it's nearly 6pm. I've got a while; the club doesn't open until 9, and I still need to make some dinner. I pull out some fixings for a sandwich and inhale it. Sure I have a lot of time, but I have to do my nails.

This club is a special spot, a safe haven for alternative genders and expressions. Sure, I'm a straight man, but I also like to cross dress. Some people might call me a transvestite, and I suppose that would be accurate. I've found that labels only really divide folks in the end, so I just explain it like this - I pick and choose my moments to dress up, and when I do I look fucking awesome.

My genetics are the envy of a lot of my lady friends. While a little on the short side for a man at 5'8", I'm at the perfect height for almost all women's clothing. My build is slim and fit due to a blinding fast metabolism coupled with the occasional bike ride on the weekend. I've got great nails and even better eye lashes, full and dark. Without mascara they don't stand out, but with it on? And eyeliner and shadow? I love it. And all that tends to be either black or dark purple - those colors seem to help my gray eyes stand out the best. My facial features are on the more feminine side, though I can downplay that a bit at work with the clothing that I wear and the way I pull back my hair.

And speaking of: I love my hair. It's just long enough to brush against my shoulders, and normally I wear it in a loose and roguish ponytail. Tonight I shampooed and conditioned it with the good stuff, and even wet I can feel how glossy and full it's going to be once it's dried. Normally a dark brown, the increase in sunlight from the changing of the season is bringing out an almost copper highlight in it.

The process of painting and lacquering my nails, both on my fingers and toes, is carried out as I watch the hockey highlights from the week. Back when I was fourteen and just realizing that I liked to dress up like this, I always thought it was strange that I wasn't gay or bisexual or transgendered. It was only in college that I was able to divorce the concept of simply enjoying wearing pretty clothing from feeling that I was the wrong gender, or wanting to engage with my own gender sexually. I guess Eddie Izzard said it best. I'm sort of like a male lesbian.

It takes about an hour or so to do all twenty nails in white, but once they're done I'm very pleased with the look. Usually I wear black polish to the club, but under the UV bulbs my hands are going to jump out, which might help me meet a few people tonight. That's the thing about the club I go to. While I get the opportunity to dress to the nines, it's hard to convince others that I'm only interested in dating women. They see a dress and assume I like cock, which I think is a little small-minded. Honest, I've got no issues with guys who like guys; I'm just into the ladies. Sorry fellas.

Tonight's look is going to be centered around my most favorite black dress ever. It's a light little linen thing in black, strapless and comfortable. The back laces like a corset, and while sometimes I pad my chest, with this dress I typically don't bother. With a slim belt in black leather at my waist, the rest of the skirt flows from that dip down to my mid thighs. Not to brag, but I've got killer legs, and after tonight's shower they're nicely shaved and smooth. I might have gotten a bit enthused with the razor, because my cock and balls are hairless now too. Though with that area all smooth it gives me a few options for underwear.

I have to wear something. The last time I tried to go commando to the club, I was flirted with pretty heavily to the point where I was pitching a tent through my skirt all night. I mean, I ended up getting laid that night so it turned out alright, but if I can avoid having to lean over the bar all evening then I'm going to do what it takes. With my nails dry, I wander to the other side of my studio and open up my IKEA wardrobe. I have a few drawers devoted to dressing up, and half the hangers support my dresses and outfits.

Standing in front of my full length, wall-mounted mirror, I pull on a black thong and I immediately feel kind of slutty. Still... it's a nice look, and given how my torso's naturally hairless and smooth, I want to show it off nicely. You know, if the dress ever happens to come off. I pull on the dress and lace it up in back, turning this way and that to admire how it clings to my chest and waist. Nice. The skirt flows down around my thighs just enough so that when I walk the dress moves beautifully without getting in my way when I sit. There's the tiniest pair of bumps in the outline of the linen over my stomach, revealing the belly button piercing I have. It's a guilty pleasure that I can wear at work without anyone noticing.

The ultimate choice between comfortable feet or gorgeous heels has to be made, and tonight I try to shoot for something half way between them. My feet are fastened into a pair of strappy sandals with a slight wedge heel. I don't like the look of a gigantic man in a dress without any sense of proportion. Everyone's gotta work with what they've got, after all.

Right! Now, I'm all dressed, and my hair's dry enough to style. I use clips on the right side of my head to bind the hair close to my scalp, directing most of it to flow over towards the right. It's a cool, almost trashy look that I've taken a liking to lately, and I seal the deal with lipstick in a dark plum, black mascara, eyeliner, and straight up ink black eyeshadow. I look at a special little skin stamp I have and figure what the hell, and soon enough a little collection of stars lingers by the outer edge of my right eyebrow.

Last but not least, I crack open my jewelry box and pull out a handful of slim silverish (what, I'm not pulling in that good a paycheck) and black chains and necklaces. This is what I use to hide my lack of tits, and it typically works in a dark club. For the hell of it I pull on these gaudy as hell flower rings in black and gray and slip one onto each middle finger. There. I am officially looking fine and ready for a night out.

I get to the club in good time, which for me is about 9:30pm. It lets the place populate for a while so I'm not strutting about a ghost town, but it gets me there before the place gets packed. I have nothing to hand over at coat check. The nice thing about this club is that it's 21+, so there's no need for bar scars or tape bracelets or any of that. With a strappy purse holding my wallet, keys, and enough cash to get just buzzed enough to make things interesting, I stride into the thrumming, dark, smoky atmosphere.

My friend Paula is tending bar tonight, and once she's done handing over a screw driver to a group of college kids she jogs over and hugs me over the bar. "Oh my God, Dani, you look amazing tonight!"

"I dunno. You think so?" I ask with a saucy smile. I know how fucking good I look, and I get a swat in the arm for it.

"Bitch, you look great. What do you want?"

I hand her a few bucks and receive a glass of sex on the beach, and like always I stuff a buck or two into her tip jar. That's how we got to be friends in the first place. That, and I'm not a giant asshole who's trying to get her to fuck me all the time. I mean... it'd be nice, but I'm cool with us being friends. It makes coming here a lot more comfortable to know that one of my friends is a regular.

While Paula wanders off to take care of a few more people, I nurse my drink and dick around with the little paper umbrella I got along with it. With my lips pursed in thought while I twirl it in front of my face, I hear a smoky voice to my left say "Babe, I think that's a little too small for you."

My eyes roll with all the petulance I can muster as I turn to the speaker, expecting some bitchy guy to think he's flirting successfully by being a dick. Though as I slide my eyes up along his tall body I realize that he is a she. The black bandaging is clearly visible over her chest through the lapels of her black sport coat. Her hair is short, but her features are that sort of androgynous that pulls off the ensemble perfectly.

I have no idea what to say. Christ, she's beautiful. Hot. I have no idea what the right word is. Oh please like men. Shit, does she know I'm a man? Fuck, I really hate having those conversations. While I'm worrying about all sorts of things as once, Paula comes back over and beams at this stranger. "Rose, this is Dani. I told you about him."

Roxanne just keeps looking at me as if she's drinking me up with her eyes, and I'm sure mine are like saucers by now. Her pale lips pull into a smile and she glances over at Paula. "You did. Pretty Thing's at a loss for words, though."

"I so totally am..." I hear myself say, nibbling on my purple lip.

Paula just snickers and gets back to work, and Roxanne invites me to one of the couches lining the walls overlooking the dance floor. We chat for a long while about this and that, and I find that she's remarkably easy to talk to and very funny. And good God can she flirt. I know that there are a lot of people in here checking her out, but while she might politely greet people she knows or thank strangers for compliments, her attention is completely on me at all times. I feel spoiled, especially since she seems fine with taking me at face value. It makes me feel so normal, and that's not a feeling I often have, sadly. I like myself and I've accepted who I am, but I've never really felt normal.

Our conversation takes us through a few drinks and a few glasses of water, and when I finally excuse myself to hit up one of the unisex bathrooms (I totally love this place) I'm a bit unsteady on my feet. With my skirt pulled up and my dick fished out of my thong and resting in my hand, I have an oddly philosophical moment about the nature of gender and identity, but it's gone almost as soon as it's arrived. Though maybe it was there for longer than I thought, because Roxanne slips into the bathroom and locks the door.

"Hey Doll Face" she says with a grin, her cheeks a bit flushed.

I blink up at her and tuck myself back into my undergarments, smoothing down my dress. "I am a doll face" I assert haughtily, and step aside for her to take care of business. But that's not what she's here for. Before I know it, my back is against the painted brick and her lips are on my neck, trailing kisses that may well leave hickeys. And... yep, there goes my dick. The thong, for the record, does nothing to trap my erection.

"Oh shit, yes..." I moan, my hands sliding into her coat to caress her waist and hips. Her back dips beneath my touch, and her hands slide down to my hips and grip at my skirt.

Whispered beneath my ear, I can hear her say "Go down on me, Dani, and I'll do the same for you."

I have never fallen to my knees so fucking fast before. Roxanne turns so she can lean back against the wall, and I'm right there in front of her, unzipping her pants and tugging them and her boxers down to her knees. The carpet matches the drapes and she's neatly trimmed, which is kind of an afterthought since my cheeks are currently shoved in between her slim thighs. I've been complimented before on my skills, and I watch her as she tilts her head back and luxuriates in it.

And I'm luxuriating in it too, to the point that both of my hands are on her thighs as I taste her and tease her. Oh, my cock is painfully rock hard but it can wait. This is all about her. Soon enough I curve two of my fingers and slip them inside, my white nails disappearing into her flushing pink pussy.

"Oh fuck, Dani..." she gasps, her hands both moving down to grip me by the hair as her hips grind into my face. I can feel her quiver inside and I know she's nearly there, so I start to thrust my digits into her quickly, taking no prisoners. Soon enough she claps her hand over her mouth and groans into it, trying to stay quiet as she tenses and cums hard. Her hot, delicious nectar flows over my knuckles and I wince a little as I withdraw my fingers from that crushing embrace, sucking them clean with obvious delight. I'm sure my lipstick is smudged, but I can fix that.

I give Roxanne a little while to enjoy her orgasm while I wash my mouth and reapply my lipstick. It's just about finished when I see her, pants all pulled up and refastened, as she moves up behind me and gropes me in a reach around. I'd just capped my lipstick when it clatters in the sink basin as I grip the counter top, flushing and closing my eyes as her hand starts stroking me off.

When I'm lucid enough to look forward at the mirror, I can see her looking at me, watching my expression. Her eyes are smoldering and I'm entranced, my breath catching in my throat. "I promised oral, Pretty Thing, but you did such a good job that I think you deserve a few more options. You got a condom on you, baby?"

My hips squirm and I nod, blushing like crazy. It's hard to keep my hands from shaking as I root through my purse to look for one of the three Trojan singles I keep in there, but soon enough I've got it and I'm ripping it open with my teeth. Roxanne plucks it from my fingers and rolls it on, and I'll be damned if she doesn't even make that sexy as hell. Soon enough we trade positions, and I'm behind her as she braces on the sink. Again I tug her pants down, and after lining up everything I sink into her. Both of us groan lewdly. I'm just a little above average when it comes to girth, and she's... oh god she's tight.

"Rough baby. Do it" she commands, and I oblige. The slapping of my hips on her ass is quick and sharp, and when she shuts off the light to the bathroom somehow it feels even more amazing. My hands roam all over her back only to feel that she's pulled the jacket off. Her skin is so smooth, and I can feel the lithe muscles beneath it writhe as she grinds back against me. In the back of my mind I approve of how she's bound her breasts - I can't feel any of the bandages cutting into her flesh, which is a mistake a lot of people who bind their breasts make. Roxanne clearly knows better. She must do this a lot, like me.

At this pace I don't take long. With one last hard thrust I grit my teeth and whimper as my cock throbs, the condom's tip filling hotly. Feeling carefully, I keep the edges of the condom pinched to the base of my cock as I pull out, careful to remove it as I withdraw. There's nothing worse than losing a condom in a lady friend. Roxanne reaches over and turns on the lights, and we both grumble as our dilated pupils fill up with the fluorescent lighting of the bathroom.

I'm just tying up the rubber and tossing it in the trash when I see her with my cell phone, typing up something. I feel so relaxed right now that I simply tug my thong back up and lean my butt against the counter to watch what she's typing in. It's her contact information. She hasn't even bothered to pull up her pants yet. With a shrug I do the job for her, buttoning and zipping the fly before handing her back her jacket.

We trade, jacket for phone, and I smile as I check out what she's entered. She doesn't live all that far away. As discretely as we can we slip out of the bathroom and wander back into the club. By now it's getting late, and we both wave to Paula as we head out to the parking lot. As we'd been making our way out I send Roxanne a text with my contact info before stuffing my phone back into my purse in exchange for my keys.

"You're still ripped, Dani" she scolds, and I pout. I know she's right. Her arm circles about my waist and she shrugs. "Come on. I keep a two liter of water in my car on club nights. Do me a favor and keep me company so I can be sure you're alright getting home, okay?" I nod, and she takes me by the hand and leads me away to her Honda Civic.

We spend another hour in her car, drinking water and talking about everything and nothing. I feel so comfortable around her that I cozy up within this wonderful feeling in her passenger seat. As I flex my fingers I realize that we're holding hands, and my cheeks hurt because I'm smiling so much. By the time we're both more than sober enough to get home, she walks me to my car and scritches at the back of her head. "Hey uh... um. Are you free this weekend? To maybe go get coffee? I don't want to sound clingy or any..."

I don't let her finish. I was bound and determined to ruin my lipstick one last time, and I do so as I wordlessly assure her with a kiss that she's being perfect. "How's eleven tomorrow, down at the Starbucks on Main Street?" I ask, a little breathless.

She grins, touching at the purple I've left on her lips. "It's a date."