Unfamiliar Territory

*** This is a work of fiction, all characters are over eighteen years of age.

She had seen me watching her several times. This last time she didn't quite smile, she grinned.

"Fuck dude, just go get her number, it's like watching a kid drooling over an ice cream cone..." Ian said. We were sitting in a newly opened bar, one of several that had similarly opened in the area, as rich real estate companies had somehow marketed the area as 'charged'. He was referring to the raven-haired woman behind the bar.

"Yeah, I mean I'm busted anyway so..." I said as I walked from our table to the bar, taking a breath and calming myself. The worst that could happen would be for her to tell me to fuck off and I'd survived that in the past so what did I have to lose?

She saw me coming and moved down the bar to meet me. Imagine piercing blue eyes, surrounded in dark whatever they call the various kinds of makeup around her eyes. Her lips were full and colored in a kind of matte red, she had little metal feather earrings dangling and short jet-black hair that tapered from nothing upwards to what I'd imagine may have been 3-4 inches curled at the top of her head. Her pointed chin seemed to direct my attention to her long, slender neck that quickly gave way to creamy white tits that struggled against the dark purple tank-top she wore. As I leaned against the bar, I could see she had on some kind of black, stretchy yoga pants that ended mid-calf, the clean white jogging shoes gave a stark contrast to the outfit.

"Something wrong with your..." She looked at the pint glass in my hand. "draft beer?" and then gave me that grin again.

"No, it's fine. I just wanted to come over and let you know I'm not a creep or anything. I mean, I know I was kind of staring at you."

"Oh, I see." She said, then tilted her head in a way that I suppose may have suggested that she was expecting more.

"I'm Tyler." I said and held out my hand. She shook it lightly for a moment. "It's a new bar and we check out new places that open in the area, so when we,"

"I'm Maya... You were saying you weren't a creep." She said, interrupting me and still grinning.

"Look, I know the place just opened and I'm sure a bunch of guys have already asked, but let me buy you a drink."

"It's against the rules here." She answered with practiced ease.

"Then someplace else."

Her head tilted over in the opposite direction and the grin widened.

"I don't understand, Tyler."

"I mean, let me buy you a drink, somewhere else like, after you get off here, or another night, you know?"

Her head moved back to it's natural position between her shoulders and she asked "How old are you Tyler?"

"Twenty five."

"How old do you think I am?"

"I don't know, old enough to serve alcohol. Beyond that it's just a number."

She watched me for a moment, the grin had turned into something else, I couldn't read her expression but she leaned forward towards me, but looking slightly away and paused there, midway across the bar. I leaned forward a bit and wondered if she was going to tell me to fuck off. I figured I was getting shot down one way or the other.

"Do you ask many Trans woman out Tyler?" She asked quietly, then leaned back toward her side of the bar. She gave me just a moment and then that damned grin of hers returned and she turned to check on a couple seated near the entrance.

After my initial shock at what she said, almost immediately afterward, I had the most confident feeling in the world that she used that line to scare guys like me away. Sure, there was a chance she may have been Trans, but that seemed very unlikely. Her shoulders were slender, clearly visible from her outfit, she had no adam's apple that I had seen, but then I wasn't looking for one. Her hand was definitely smaller than mine when we shook hands, I'd guess she was maybe an inch, possibly two shorter than me and I'm 5'10", her tits wouldn't have been a factor, obviously many Trans women get breast surgery, but just everything else about this woman seemed very unlikely to have once been a guy.

As I walked back to our table, Ian was looking at me with a wild-eyed smile, he spread his hands a bit in the typical 'Well?' expression.

"She smells like cinnamon dude and those eyes are fucking kryptonite." I sighed.

"Struck out huh?" Ian nearly laughed.

"Not yet." I answered. This is where things get complicated. I have this way of attempting to analyze things more than what I suppose many others do. So while I tried to pay attention to Ian, I'm asking myself if I could actually date a Trans woman, especially when she looks as good as Maya does. I have the obligatory 'But I'm not gay!' thoughts, but I'm just seeing this very beautiful, possibly bratty woman that seems very at ease in her skin. I skip ahead and imagine her naked and I can't shake the image of a dick hanging between her legs. But then I wonder if she had it removed. More selfishness, hoping she did, just to make me feeling less confused. But after all of this mental nonsense, I shook my head and finished my beer, then looked at Ian and offered a 'yeah dude.' I had no idea what I had just agreed with, but he seemed to agree as he nodded as well. I took his glass and went back to the bar for a refill.

"Two more?" Maya asked as she approached.

"Thanks." I said as I watched her refill the glasses. I figured it would be best to go down in flames instead of a whimper.

"I think you use that line to scare guys off, but even if it's true, I don't care."

"You sure?" She said as she pushed the glasses across the bar.

"Mmhmm." I offered in response with a nod.

"I don't work tomorrow night, I know a new place that just opened with excellent service." She said as she made a scene of looking all around the interior of the bar, then looking back at me. "Seven tomorrow night?"

"I'll be here, say... What's your favorite flower?" I asked, I'm sometimes an awkward romantic.

"I'm not much of a flowers kind of woman Tyler." She said and that grin returned. Shit, I really hoped she was just fucking with me.

~

"I haven't gone out with anyone as young as you since I was... eighteen I'd guess." Maya said as she sat across from me, at a table that was near to the one I'd been sitting at the night before.

"That means I'm special, I'll take that as a compliment." I said as I sipped my beer.

"It's a warning, if you start carrying on about whatever video game your playing, I'm leaving." She sipped her rum and coke, then grinned.

"It's not polite to ask a lady her age." I commented, but was very curious.

"I'm going to be thirty this year, have you made up your mind if I'm a lady Tyler?"

"You're definitely a lady."

More grinning.

Our conversation felt like we were avoiding the elephant in the room and so I figured I needed to find out, one way of the other, truthfully. At the very worst, spending a few hours and buying her a few drinks wasn't a big deal if she had a dick.

"So, be honest." I started "I'm nearly convinced you said that yesterday as a shit test, to see if I'd still be interested."

She grinned.

"I said 'what', exactly?"

"You asked if I asked many Trans women out."

"Oh that." She sipped.

"How many other Trans woman have you gone on a date with?"

"Just you." I said, facetiously.

"That means 'I'm special' too, like you."

touche.

"But here we are, so if it was just a line, it didn't work. so now what?" She asked and sipped her drink.

"And I'm younger than guys your normally date, so I guess that makes me 'extra special' huh?"

"I don't know if I'd go that far." She laughed.

"Seriously. Is it true? Before you answer I only want to know so I'm not wondering for the rest of the night."

"I'd manage somehow if you got up and walked out." She did that tilted head thing "But to answer your question, it's true."

I still didn't believe her, even after she had said as much, several times.

"Wow, well at the risk of repeating something that might be cringey for you to hear, I mean this in the most complimentary way... I would never in a million years have guessed."

"That, Tyler, is the goal." She answered, in a tone that sounded like she was talking to a child.

From there, the conversation relaxed and while I had decided that in spite of how she looked, I'd never be okay with having sex with her because of my insecurities.

As we talked, more people began filtering in and anytime a guy would walk past our table to use the restroom, they'd check Maya out. It was like all of them were subliminally saying 'Dude, she's fucking hot!, Whats wrong with you??!!'

But I didn't need any help realizing that. She had all of those things you want in a woman. Gorgeous, great sense of humor, smart and she had this way of flirting that made me feel like a horse with the proverbial carrot dangled in front of it.

I couldn't shake the thought of her having a dick, it was like a cruel joke.

We finished up a bit after 10:00pm with both of us having a bit of a buzz. I held the door open for her as she stepped into the cool night air and like any conscious male, I gazed at her fantastic ass as she passed.

"Where are you parked? I'll make sure you're safe." I offered.

She gave a soft laugh and said that 'safe' didn't apply to her. I could tell. "I live around the corner, I walked. Before you get your hopes up, I'm not going to invite you over. We just met and you still have to figure out how you feel about me. I suppose I still need to figure out how I'm feeling about you."

"I'll walk with you, if you'd like." I offered.

"You don't have to." She answered, and maybe for the first time that night, at least to my ears, she sounded a tiny bit vulnerable.

"Sure I do." I quickly replied and held my arm out to her, she surprised me by taking hold of it. It was nothing, but it somehow made me want her in a desperate way.

When we stopped in front of one of the old office buildings that had been converted into apartments, she turned and said "Well, this is me. I had fun, thanks Tyler." She watched me with a calm that I wished I could have matched.

"Let me buy you dinner, I want to see you again." I could have just said that I enjoyed spending time with her, I could have made a clean break and maybe that was exactly what I supposed she was waiting for me to do, but that's not what I did. Asking to see her again, was telling her that I didn't care that she was Trans, and in truth, I didn't care, it was just that issue of her potentially having a dick that was complicating things.

"Take a few days to think about it." She stepped closer and asked "Want a goodnight kiss?"

It felt like all of the air seeped out of my chest and I needed to breathe, but all I could manage was a 'Yeah.'

Her hands moved up to my shoulders and she took the final step towards me as I stared at her and hoped that I didn't look stupid.

"Close your eyes." She nearly whispered, a moment after my lids shut, her lips were on mine, warm, moist, soft. My body immediately screamed for more.

Instinctively, my hands were on her hips and then I felt the tip of her tongue lightly glide across my lips, it lasted less than a second, then with a quick final kiss, she stepped back and said goodnight.

~

I don't remember driving home, but I got there and it wasn't because I was drunk. I just couldn't think of anything besides what had happened. It seemed like, I had to face the reality that the beautiful woman I'd spent the evening with had a penis, to complicate things, I wanted to see her again and I wanted her mouth on mine again.

I've never considered myself homophobic, I've always believed in 'live and let live', but I've just never been interested in sex with a guy. This was far more complex that that though. Clearly, obviously, painfully so, Maya was not a guy, there had been nothing at all she had said, or done that gave me the slightest indication that she had been born male. She had kissed me goodnight and I suppose in some circles, some people would consider that two men kissing, but I promise you, that wasn't remotely what it actually felt like.

That thought sobered me up very quickly, if kissing her felt perfectly natural, would anything else that might happen between us also feel perfectly natural? In the back of my head, I saw no reason to think it wouldn't.

But what else did I want? What if we went to dinner and enjoyed ourselves again? What if I asked her out again? It was difficult to rationalize things beyond simple attraction, thinking too much more about everything else made me less sure of what I wanted. I suppose for me, it was like stepping out of a space ship on a new planet and realizing it had fresh air. There was certainly that part of me that had just never imagined I'd ever even want to date a Trans woman, but Maya had kind of turned that on it's head. It would have been stupid to keep wondering if she was Trans at this point and instead I needed to figure out if that was something that I could deal with. In that moment, I knew that she was very beautiful and that her kiss had been unexpected, but I wanted more of them. It took all of a fraction of a second to realize that having kissed her, didn't result in me spontaneously turning gay, so it seemed safe to continue seeing her.

Would it be okay to do more than kiss her? Would I be fine with her offering to blow me? Would she want me to do that to her? What if she wanted me to do more than that to her? What if she wanted to do more than that to me?

My dick was in a confused state of stiffening,and deflating. I pictured her kneeling between my legs as I lay in bed, stroking my dick, I imagined her soft lips moving easily up and down the length of my erection, but her eyes would remain riveted to mine. From her position between my legs, I could marvel at her tits as they hung heavily towards the bed. This all quickly became a scenario that I accepted as something I could get on board with. I just fantasized about her sucking my dick and instead of a dick hanging between her legs, I imagined nothing, smooth flesh, like a doll. That was easier to reconcile. It would be fine to imagine her turning away from me and slowly impaling her ass on my dick, and then with the grace of a gymnast, rolling her hips to massage a tremendous load of semen from my balls.

When I came, it was like I'd been hit by lightning.

The next day I slowly talked myself into caring less about who she was born as and more about who she had become. It may have been that I had dated too many of the same kind of woman, and that's not to say that I've had a lot of bad experiences, only that I could see a pattern had developed and while all of the women I had dated had been their own unique individuals, I had to admit that there hadn't been a single one I would have seriously considered spending the rest of my life with after a month or two of seeing them.

In all likelihood that was a reflection on me more than anything else, but I had always imagined when I found the 'right' one, I'd know and so far, that hadn't happened.

Now, to be clear, I wasn't imagining walking to the alter with Maya, only that it may do me some good to step outside of my comfort zone and so that's exactly what I decided to do. To be clear, Maya wasn't an experiment, it felt like she was simply 'not the same old thing.' First, I needed to see if she would go out with me again, but she had made it sound like that was something I needed to decide. After work, I stopped at the bar she worked at and some guy I hadn't seen before was tending bar. Like any other guy that was messing around with an unexpected attraction to a beautiful Trans woman, I embarrassed myself by not being able to just ask the guy when Maya was working, and if she was working tonight. After a beer, the guy came by to check on a fresh pint and I asked if Maya was working that night.

"Are you Tyler?" he asked, his face seemed almost uncaring and that was fine with me.

"Yeah."

"She left her number, hang on." He turned and found a post-it note somewhere below the bar and handed it to me.

I finished my beer and left. Sitting in the parking lot I figured I'd call in case she wanted to grab dinner, I'd be close enough to be at her place in a minute or so.

"Hello?" Her voice seemed a bit different on the phone.

"Maya, it's Tyler."

"Are you at the bar Tyler?"

"I'm in the parking lot, yeah."

"So, I'll bet you argued with yourself all day before you decided to see if I was working, huh?"

"Yeah, I guess."

"You get points for being honest, I appreciate that."

"Does that make me an asshole?"

"It's too soon to tell, so do you want to ask me to dinner? Or are you calling to see what it's going to take to get me into bed."

"That's not why I'm calling." I answered immediately, I wasn't expecting her being this forward.

"Are we just going to be friends then? You're kinda cute, I don't know if I could just do the 'friend thing' with you."

"You're fucking with me." I answered and questioned if calling was a good idea.

"Not yet."

"Not yet, as in, we're not fucking yet, or you haven't started fucking with me yet?"

"What do you think?"

I didn't know.

"Ready to have a grown-up conversation Tyler?"

"Yeah."

"Still in the parking lot?"

"Yep"

"I have vodka, if you want any of that cheap beer you were drinking in the bar, you'll have to bring some. Call me when you're at the door to my building, I'll come down and let you in."

I decided to just walk to her place and leave my car in the bar's parking lot. When I was close I called and she was at the door a minute later. She had a crop top on and a dark pair of those shiny cycling shorts, it's fucked up, but I gave the place between her legs a hard look, but couldn't see anything like a bulge.

"Do I get a kiss?" She asked and gave me one of those grins of hers that felt like a drug.

It was soft and too fast, just like the last one. Then we were on our way up an old elevator and she led me to her apartment, opening the door I nearly choked as the very first thing I saw was a poster hung on the wall, it was a frontal shot of a guys torso with beads of water splashed on it and below a shaved pubic area, what may have been the largest dick I'd ever seen and it was limp.

I must have given myself away.

"You like?" She asked, and for the first time I heard her giggle.

"Just surprised is all." I answered, trying to play it cool.

"Something to drink?"

"Sure, whatever you're having."

"I'm having a screwdriver and I like them strong."

"Sounds good to me."

I sat on her sofa and caught myself looking at the poster again.

Naturally, she busted me immediately.

"An old friend sent it to me, she said she knew I'd like it. It seems we have similar tastes."

"I'm not into guys." I said shaking my head and drinking the powerful cocktail.

"It's important that you understand that I have one of those between my legs too, so if we're not going to just be buddies, you need to get to terms with that." She said, it wasn't that her tone was harsh, but it was definitely unapologetic.

"I swear I still think you're saying that to scare me off." I answered, it felt like I kept circling back to not believing her, even though she had just told me, once again, that she had a dick. Only now, I couldn't shake the thought that she had a huge dick, like the guy on the poster, that started a chaotic series of thoughts to race through my head.

"I haven't lied to you Tyler." Her answer may as well have been commenting on the weather. It didn't seem like a big deal to her.

I nodded, and drank again.

"So... what are you expecting to happen, between us." Her voice held a bit of curiosity, but I wasn't ready to start celebrating. Her question made perfect sense, and maybe I just hadn't entirely thought this through, in fact I knew I hadn't thought it through.