Seduced with Logic

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How a transgirl seduced me with my own words and logic.
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This was the last thing I expected on my business trip.

My name is Levi, I was 30 years old when a chance meeting in a hotel bar changed my life forever. After college, I had bounced around a few different jobs before I finally found one nine months earlier that fitted my liking and education.

I was a Product Manager for a Surgical Device manufacturer and would travel on a quarterly basis to local Trade Shows to meet with Surgeons and Operating Room staff. My job was to gather feedback on our existing products and discuss ideas for new ones.

I had been looking forward to this Trade Show for the past three months. This one was outside of my assigned Midwest territory, it was in Honolulu, and I would be covering for the West Coast Product Manager who was on Maternity Leave. Lucky me!

I had checked into my hotel, unpacked, showered, and headed down to the bar for dinner and a few drinks. I always felt uncomfortable sitting in a restaurant by myself, I felt more at ease and at home sitting at the bar. Especially at the end of the bar where I had a better viewpoint.

I had never been to Hawaii, I was looking forward to some beach time and looking at beautiful women when I wasn't at the show. I even used up a couple of my few vacation days as a new employee to stay on after the show ended.

As I sat there enjoying my local draft beef and cheeseburger with pineapple, I noticed the diverse mix of the people in the bar and restaurant. It was quite different from the small Midwest town that I grew up in and the big cities that I traveled to in my territory.

I could go days back home without seeing an Asian person, everywhere I looked, at least half the people here were Asian. Many were locals, but many also appeared to be tourists from Asia. I thought the women looked both exotic and erotic.

The bar was filling up and the only seat available was right next to me. Out of the corner of my eye I saw a beautiful Asian woman enter the bar and walk down the line of occupied bar stools. I thought to myself, "This is too good to be true." I planned to casually look up and make eye contact with her as she approached the vacant bar stool, and let her know it was available.

She took notice of the open seat, glanced at me and smiled slightly, and continued on past me. My hopes and spontaneous erection faded. I was right, it was too good to be true.

I finished off my burger and ordered a second beer. I continued to scan the crowd, hoping to see another attractive female looking for an open seat. To my surprise and delight, my mystery woman returned and asked, "Excuse me, is this seat taken?"

In my effort to appear chivalrous and charming, I responded, "I've been saving it for you, I was hoping you would come back." Then I added, "I had to beat off three guys just to keep this seat open"

She gave me a sly smile and said, "Really, you beat off three guys in the last five minutes, please forgive me if I don't shake your hand."

"Wait, what, that's not what I meant," I stammered, as she caught me off guard with her quick wit.

She smiled as she sat down and said, "I knew what you meant, I was just messing with you."

The bartender returned with my second beer and without hesitation she reached over and grabbed it and said, "Thank you, that was so sweet of you, why don't you order one for yourself."

I looked at the bartender who seemed to be enjoying the interaction, and said "I guess I'll have another beer when you get a chance."

I was immediately both impressed and smitten. Beautiful, sexy, and funny. She was of Asian descent, about 5' 4", brown bedroom eyes, maybe mid-twenties, smooth brown skin, and a mischievous smile. What's not to like about that?

I guess she changed her mind about shaking my hand, she offered her hand and introduced herself, "Hi, I'm Alex, nice to meet you. Thank you for whatever you did or supposedly didn't do to those three guys to save this seat for me."

I pretended to wipe my hand off on my pants before I said, "Hi Alex, I'm Levi, very nice to meet you. I really told those men that I was saving the seat for my wise-ass date."

I tried to be a wise-ass myself and said, "So Alex, I take it your parents were wishing for a boy."

Without missing a beat, she was successful at being a wise-ass, and replied, "Well one of them did. So Levi, I take it your parents were wishing for a pair of jeans."

The bartender returned with my beer and we clinked glasses to our new acquaintance. I told her that I was there for a Trade Show and then I would be staying a couple of extra days to be a tourist.

We made the usual small talk, family, where we grew up, where we went to school, what we do for a living. She was 25, Japanese, grew up and went to school in Honolulu, and worked in Human Resources at one of the Hospitals that used my company's products.

Our conversation flowed freely, it never felt like an interview, or an awkward first date. I was mesmerized by her beauty as well as her sense of humor and ability to talk about any subject. It was like hanging out with a guy friend, having a few beers, talking shit, telling stories, yucking it up. Well except for the fact that she was a beautiful and sexy woman.

At one point in our conversation, she caught be staring at her face, taking in her natural beauty. She snapped me out of it by asking, "Is there something on my face?"

"No, not at all, just a pretty smile," I said as I tried to recover. "But I must admit, I was drawn in by the beauty mark in your left eyeball. Cindy Crawford has nothing on you."

She looked both surprised and happy as she said, "Thank you, that is the first time someone has referred to that as a beauty mark, usually I get asked if there's something in my eye."

Then with a wink of her eye, she added, "And that's not all that I have over Cindy Crawford."

"I'm sure it isn't," I quickly agreed. I surely hoped to find out.

"I'm impressed that you noticed the spot in my eye, most guys are too busy looking at a woman's cleavage."

Trying to further distance myself from "most guys", I looked at her straight in her captivating eyes and tried to pretend that I would never do such a thing, and said, "What cleavage."

She pretended to be offended by my remark, and responded, "One minute you tell me Cindy Crawford has nothing on me, and the very next minute you imply that I am flat-chested and have no cleavage. I'm afraid of what you might say next."

"That's not what I meant, I wasn't referring to you," I shot back. "But if I were, I would say your cleavage is perfect."

I was going to say proportional, but perfect sounded better. I had previously noticed her minimal, but still eye-catching cleavage. I just figured being petite and Asian, her breasts were proportionally perfect.

"I knew what you meant, just messing with you again. And yes, they are perfect," she said.

Hoping to get some sort of response out of her, I said, "I guess I'll just have to take your word on that." Her only response was a roll of her eyes.

She then shifted the subject and asked, "So what do usually do when you are away from home on business trips, besides talking to strange women in hotels bars and beating off three men?"

She just wouldn't let it go, I liked that about her. I told her, "First off, I wouldn't really call you strange, maybe a little different and quirky, but not entirely strange. And secondly, the only man I beat off is myself when I go back to my hotel room alone and watch porn on my laptop."

I thought I finally caught her off guard with that remark, I said it as if I were kidding, but we both knew otherwise. She laughed for a bit and came back with, "So tell me Levi, what kind of porn do you watch while you are beating off a man again?"

"You know, the usual stuff. Great storylines, sexy women, a lot of sucking and fucking." What I said was true, only if your definition of the "usual stuff" includes bukakke, cum kisses, pegging, spit-roasting, and threesomes. Two of my favorite categories for searching were always "Asian" and "Small Tits". But I wasn't going to tell her that, at least not yet. It was too close to home.

"Alright, so you usually watch the usual stuff. What's the unusual stuff that you watch? If I went to your room and opened up your laptop and went through your search history, what unusual porn would I find that you have watched?" she asked with her mischievous smile and bedroom eyes.

I didn't want to scare her away with anything from the list above, so I told her, "Well as a 30 year old guy, I kind of like watching a younger guy with an older, more experienced woman. Milfs, not Grannies."

"You can do better than that, how is that unusual for a horny 30 year old guy to lust for a Milf," she said, somewhat exasperated.

Faking my own exasperation, "Well if you would let me finish, I will tell you," I said. "One day as I was scrolling through the porn categories looking for Milfs, I saw the category Ladyboys and mistakenly thought it meant Mature woman with younger guys."

"You're either lying or you really are a rube from the Midwest. So tell me, did you hit the back button right away and return to your usual stuff?" she asked in a sarcastic tone.

"Actually, I watched quite a few of them, I was amazed at how beautiful and sexy they were. And to be honest, I have watched them since. Do you have any more questions Detective?", I answered in a matching sarcastic tone.

"Well now that you are being honest with me, I have one more question. Since you enjoy Ladyboy videos and you already beat off three men today, do you also watch Gay videos?"

She was as entertaining as she was beautiful and sexy. I smiled at her comment and said, "Yes, I do enjoy Ladyboy videos, and no I don't watch Gay videos. And once again, I didn't beat off three men today, I was lying before. It was only two men."

She laughed at my response, but quickly asked one more question. "Why don't you watch Gay porn? You watch Ladyboy porn so I assume you are intrigued by their cocks."

She assumed right, I was more than intrigued by their cocks, I was mesmerized by them. At first I would watch the videos with the Ladyboys sucking the man's cock and the man fucking the Ladyboy and would imagine that I was the lucky man.

But after a short while, I would watch the videos with the man sucking the Ladyboy's cock and the Ladyboy topping the man. I imagined myself to be that even luckier man.

That was more information than she needed to know. She already knew that I was attracted to her, and she seemed to reciprocate the feeling. I didn't think that telling a woman whose pussy I wanted to lick and fuck that I fantasized about sucking a Ladyboy's cock.

I responded to her question, "I don't watch Gay porn because I'm not Gay."

She shot right back, "Do you consider the men in the Ladyboy videos to be Gay?"

"I thought you had only one more question Detective. They may be Gay, but I don't think being with a Ladyboy requires you to be Gay."

I already knew there were more questions to come, I was actually enjoying the give and take. I could never be this open with a girl from back home. Nor could I ever be with such a pretty and sexy girl back home either. And I definitely couldn't imagine any of the girls back home asking me these questions.

She proved me right by asking, "So you enjoy watching Ladyboy videos and you don't consider the men in the videos to necessarily be Gay. Does that mean you would be open to being with a Ladyboy? Or do you just enjoy beating off to Ladyboy videos?"

Talk about loaded questions, that sure was one. I've known quite a few women who ask questions that are actually traps. And this felt like one of those trap questions.

I answered her honestly and said, "I think I would be open to being with a Ladyboy, but I'm not sure I could go through with it. But I also know I would be very tempted to do so."

"I applaud you for your honest answer," she replied. "Would you hesitate because of the Ladyboy's cock? Maybe you would prefer a post-op Ladyboy, I'm sure you've watched some of those videos before, now haven't you?"

"Yes, I have watched some post-op Ladyboy videos, and was attracted to their beauty and sex appeal. However, I would watch only one and then go back to watching the Ladyboys with cocks videos. But it just might be an easier first step to be with a post-op Ladyboy."

Her analysis was, "So you like the pre-op Ladyboy videos better, but you would be more comfortable with a post-op Ladyboy. It sounds to me that what you are curious about is also what you scares you."

"I wouldn't say it scares me, it would just be different. On the other hand, although I imagine being with a post-op Ladyboy is different than being with a born female, it just might not be different enough."

She gave me her wicked smile and said, "You've weaved around this one long enough, are you going to answer my question or not?"

I couldn't believe I was telling this to a woman who I wanted to sleep with, and reluctantly answered, "If I were to take a walk on the wild side, I would take a giant step, not a baby step. I would choose to be with a Ladyboy with a cock. But I'm still not sure if I could actually do it."

"Once again an honest answer from Mr. Jeans," said the girl who had one parent that had wished for a boy.

"Now let's play a game called "Is this Gay?"

"I take it I don't have a choice at this point," I protested.

"Not really, unless you are bored with me and want me to leave," she said with a her mischievous smile.

"How could I possibly be bored with you? You're quite entertaining and actually kind of pretty," was my answer to another trap question. I had made it a point to not comment on her looks up till that point. Beautiful women hear compliments all day long and become immune to them. Maybe not all of them.

"Why thank you for the over the top compliments, you surely know how to make a girl blush. I'm not blushing am I?", was her response.

"Okay, first question. A girl is giving you a blow job and reaches up and plays with your nipples. Is this Gay?"

I looked at her and pretended to ponder the question before I said, "Not Gay, final answer."

She rolled her eyes and said deadpan, "This is not 'Who wants to be a Millionaire,' you're not going to win any money here tonight. Next question, a girl is giving you a blow job, reaches up and offers her finger for you to suck, and then slides her finger up your ass to stimulate your prostate. Is this Gay."

"Only if she has long fingernails," was my not final answer. "Otherwise, no, it is not Gay."

"Alright next question, a girl is giving you a blow job, and instead of her finger, she reaches up and offers puts her slim vibrator in your mouth to get lubricated before she slides it inside you to stimulate your prostate. Is this Gay?"

"I would say that it would be an extra $50, maybe more," was my wise-ass reply.

"Okay Mr. Happy Ending, how about an honest answer now," she said as she shook her head.

"No, it's basically just replacing her finger, I don't consider that to be Gay," I answered.

"Now let's take the same girl giving you a blow job, but instead of her slim vibrator, she puts a realistic looking dildo in your mouth to lubricate it before she slides it inside you. Is that just replacing her finger and slim vibrator, or is that Gay?"

Damn, these questions were getting harder, and so was I. I was trapped by her question and my own words, and the blood rushing from my brain to fill my cock didn't help matters.

In my mind I was thinking, "Yeah, that's kind of Gay," but logically, it was just replacing her finger and slim vibrator which I had already stated wasn't Gay.

I had backed myself into a corner, or maybe she had done so with her game. I answered firmly, "No, that is not Gay, it is merely replacing her finger and slim vibrator." I thought that might be her last question. I was wrong.

"Well Levi, I must say for a rube from the Midwest, you're more open minded than I suspected," was her backhanded compliment. It was also the first time she called me by my name.

"Now let's see just how open minded you really are. Now the girl stops giving you a blow job, and just focuses on playing with your ass with her cock-like dildo, is this Gay?"

Once again, I was trapped by my own words and logic. I answered, "Well it wasn't Gay when she was giving me a blow job, therefore, no it still isn't Gay."

I was more than ready for another drink, and asked her if she wanted another one. "I'll have another beer, and let's both have a shot of Tequila. I think you might need it to finish the game," she replied with her ever-present mischievous smile. Well almost ever-present, other times she had a seductive smile. At least in my mind.

I couldn't believe how lucky I was, sitting at a bar in Honolulu, with the most beautiful woman in the place, and enjoying her strange but intriguing game.

The bartender returned with our beers and shots, and I followed her lead of licking her hand and shaking salt on it. She raised her shot and said, "To my new friend Levi, welcome to Hawaii." As she raised her glass with one hand, she reached out and touched my forearm with her other hand.

I toasted her back, "To my new friend Alex, I can't imagine a better welcoming party. You are something special."

She looked at me with her mischievous smile and said "Yes I am special."

"I am sure you are," were my words. My thoughts were, "I hope to find out just how special you are."

Then I asked her a question that was running through my mind, "What's the purpose of this game, are you trying to determine if I really am the type to beat off three guys? I already told you that I'm not Gay"

"It's nothing like that you big dope," she said with a smile. "In my job in HR, I work with many members of the LGBTQ community. Also, I have some friends and family members who are part of that community. I'm just trying to determine if you would fit in with them should I decide to be your Tour Guide during your stay."

That was the first time she said anything about spending more time with me beyond our happenstance meeting at the bar. This was too good to be true. I actually had a chance with this gorgeous woman, I sure hoped my answers would make me a good fit for her and her tribe.

We knocked back our shots, and she announced, "Let the game continue. Next question, the girl who is playing with your ass also wants to kiss you, but she can't do both. So she puts her toy in a harness and wears it around her waist and now she can kiss her stud and play with his ass at the same time. Is this Gay."

That was a hard one, and it was making my cock even harder. I had watched a few Pegging videos before, and had been turned on by them. I hadn't previously confessed that to Alex, but then again, I hadn't confessed it to anyone else either.

Also, how could it be that different from using her hand to guide the realistic looking dildo inside me? Plus, I would get the bonus of kissing her at the same time. I always enjoyed kissing while I was getting laid, I had just never thought about being the one who was getting fucked.

With those thoughts in mind, I answered, "It's getting closer to being Gay, but I would say to you that it still isn't Gay. I'm not so sure that I would say that to my friends though. But hey, what happens in Hawaii stays in Hawaii, right?"

"You dork, that's Las Vegas, not Hawaii. We're coming down the homestretch here, just a couple of questions left. Would your last answer be any different if the girl wearing the strapon cock was a post-op Ladyboy? Would that be Gay?"

I had already told her I thought the post-op Ladyboys in the videos were beautiful and sexy, and I just told her that getting fucked by a woman wearing a strapon wasn't Gay.

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