I was in New York for work and work was going bad. I needed to get out of my mind for a bit and remembered the hotel I was staying in had a rather large bar in the restaurant. I sat down toward the end of the bar and ordered a double whiskey neat and began drowning my sorrows. My phone kept buzzing. Another work email. I scoffed it off and kept drinking. A few more ignored emails and what was the beginning of a second whiskey neat, I saw her.
Petite, barely five feet tall and no more than a hundred twenty pounds. Long multi-color dyed hair pulled up in two buns on top of her head while a few strands fell on both sides of face framing her piercing blue eyes that sat above her precious freckled cheeks. She wore hardly any actual make-up, but a lip gloss that made sure everyone knew just how luscious her lips were. An e-girl for sure, with a video game t-shirt that's a size too small accentuating her perky b-cups and plump nipples. Tattered jeans so tight they seemed painted on lifting her adorable small round ass.
She looks right at me and says "Hi!" as she walks by. I was shocked and could barely speak. "Yeah!" I said awkwardly as I felt she had caught me checking her out as she came in. She smiled confusingly and furled her brow to question my response. As soon as I knew she wasn't looking, I found myself gawking again. She looked back after sitting at the other end of the bar and definitely caught me this time and revealed the slightest smile before turning back to her acquaintance she came in with.
I continued to look this girl up and down any chance I could get and quickly began fantasizing about all the naughty things. I had finished my drink but didn't want to leave. I was much more intoxicated by this woman than the alcohol so I had to stay. I ordered another whiskey and began nursing it while trying to come up with an opening line.
She stood up. I thought I lost my window, but it was just her friend she came in with who was leaving. When she hugged her friend goodbye she looked directly at me. This was my chance. She sat back at the bar, looked at me, smiled and raised her glass. I couldn't have asked for a better opening, lifted my glass and gave a nod to the bartender and then the girl to let him know where I was moving. He gave a quick nod to confirm and then I saw him release a small laugh and slightly shook his head back and forth.
I asked, "May I sit with you?"
"You may," she said laughing, slightly mocking my politeness.
She eyed the bartender and I asked, "What's that about?"
"Oh don't let him be a bother. He's just the jealous kind." she said in what I guessed to be an Irish accent I hadn't even noticed before.
I wanted to comment on it but figured it was probably what everyone tells her.
"I'm Jacob" I told her, extending my hand for hers.
"Teagan" she replies, giving me her free hand.
"I really like your look," I said, lifting my glass to take a sip.
A brief pause and she squishes her nose and face up, pulls her shoulders in to express pretend bashfulness while letting out an "awwww".
"Precious and adorable too!" I blurted before continuing, "I love your hair."
"Thank you. Though it is a bit to maintain," she responded.
"I believe you. I used to have long hair and while I've cut it off, my beard has become my maintenance nightmare," I said, relating our experiences.
In my head I was blowing this entirely despite each exchange not getting shut down but encouraged instead.
She giggled again but this time she seemed concerned. She shook her head similarly to how the bartender did before. I noticed it, but figured I'd let it go.
We flirt a bit more and eventually she continues to laugh with concern so much that I can't help but ask, "Did I say something wrong?" continuing "I can't help but notice you're not laughing quite the same as before."
She quickly shifted her posture in her chair while inhaling and then exhaled and said, "This is always difficult. I don't want to upset you."
I interjected while pretending to laugh, "Ha. Ha. Ha. Let me guess. You're a lesbian" while in my head I was certain it could be a number of things. Married. A hooker. An undercover cop. All of which I'd have believed.
She genuinely laughed hard and replied, "well, no, while I do enjoy a woman's company on occasion, I definitely prefer men," she said while looking me up and down, "you're also actually not too far off."
I was extremely confused. She saw the blatant facial expression I was giving her as a way to ask what it could be.
She leaned into the bar and insinuated I do the same with a small "come here" nod.
"I'm a trans woman," she said bluntly.
I quickly saw her sincerity and knew she must be feeling rather vulnerable so I quickly responded, "Pshh. Don't want to upset me?" laughing and leaning back up in my chair, "I thought you were gonna say you were married."
She leaned up and began to smile. "This doesn't bother you?" she said.
"Bother me? Girl, I'm even more interested now" I responded in a tone of sarcasm in how she would question otherwise.
"So you're into trans women?" she asked.
"Well I'm bisexual so I've been with men before. And while I've never sought a trans woman, I'm definitely into this trans woman in front of me." I said while eyeing her body up and down.
She makes a shy face gesture but follows it with a slight "mmmm" and licking of her lips while cutting her eyes at me.
At the point she started licking her lips at me, I sorta lost control. My eyes widened and I just stared at her mouth. My mind was racing. All the things I wanted to do to that mouth now.
I snapped out of it and said exactly what I was thinking. "So I said I was bisexual, but in fairness I've never had the desire to kiss the men I was with. I enjoy being with men because... well, because we know better than most women how best to please a man."
I paused and she looked at me with a peculiar look.
"Sorry. Let me finish. What I mean to say is, I actually would very much like to kiss you, which is a fascinating revelation I'm having." I said, instantly thinking how that might have made her feel awkward.
I felt her place her hand on my thigh and say, "That can be arranged."
We both seemed to be making the other blush a little while also getting turned on. We only continued to encourage the others' behavior which helped to dissipate the awkwardness and blushing. We were soon speaking much more openly once we both fully realized we were interested in the other.
"So are you staying here in the hotel?" she asked me while removing her hand from my thigh.
"Yeah. I'm on the..." I paused as I looked at my key card I pulled from my inside jacket pocket, "thirty-second floor."
"That must be a nice view of the city," she said.
"I prefer the view right here", I smiled and quipped back as I reached down and slowly ran my hand up her thigh.
She grabbed my hand as I moved closer to her inner thigh so I began to respectfully pull back.
"No wait." she said quickly under her breath almost as a whisper and pulled my hand further toward her crotch until she was certain my hand was pressed firmly against her extremely hard cock.
My eyes lit up and I smiled so big that she in turn began to reveal the same kind of naughty smile.
"Oh my. Now that's a hard cock," I said, readjusting my current seated position and continuing while glancing down at my crotch, "and now we have two hard cocks."
