My most spiritually, sexually, and mentally disruptive first date left me questioning myself in deep and profound ways. It set me on a path of examining dimensions of my fantasies I had never even considered before…

I arrived at the Seattle waterfront about thirty minutes after leaving my house, one final check of my lipstick and teeth in the rearview. I couldn't help but admire my jawline as well, a feature I've been complimented on so many times I've come to accept it as one of my best features. Not bad.

"Please don't fuck me over on this one, Mary," I said to myself as I got ready to meet him for the first time.

The texting was light on flirting and more of a logistical conversation. Mary had sworn that we would hit it off, which must have been awkward for him to hear at the end of his first date with her. But I enjoyed receiving the recommendation, which is as close as a girl can get to meeting a guy organically these days.

Walking to the restaurant’s entrance, every step made me feel more and more confident in my choice of outfit. Men pretending to be looking at something and quickly glancing in my direction as their desire dry-humped my impenetrable aura. A white button-up blouse with just enough cleavage showing and a bold black bra peeking through underneath. A gray pencil skirt added an extra touch of sophistication with my black chucks to embellish a factor of questionable sanity, which, of course, was put over the top by my square-boxed Oliver Peoples glasses. As I strode, pride brimming through the sheen of my hair, I realized that I had no idea what my date even looked like. I was briefly overwhelmed with how much faith I had put in Mary.

"He's just your type."

I hadn’t the presence of mind to even question what that meant. Had my battle against desperation betrayed an easy opening that made me lose my wherewithal? I shook my head, realizing that the question was the answer... And well, in a few seconds, I would see just how far off the mark she was.

As I walked in, I checked my phone one last time to ensure I hadn't missed any details. He said he'd be at the corner table by the window. His instructions were bare but sufficient.

He was staring out the window as I walked up to him. I was absolutely stunned by how unremarkable he was. Cute profile, but just on this side of handsome. Slightly worn. A haircut that was not overly neat but not overgrown. He didn't use hair product. Plainly dressed in a neat black t-shirt and gray pants. This is ‘just my type’?

He wasn't even on his phone, so I couldn't tell what his Instagram reels were made of. He did have a traditional analog watch, not a smartwatch, which was a little refreshing and different. Not one to judge based on appearance only, I had to get over the first impressions and quickly pushed them out of my head just before my alarm bells began to tingle ever so slightly.

His gaze slowly turned from the scenery out the window toward my direction. A seemingly innocent wander of his look from the exterior to the interior and then to me. An aloof expression that turned to an endearing focus the moment our eyes met. It was too slow a motion. It was too perfect timing. It was as though he had spotted and knew it was me the second I walked into the restaurant and began staring out the window as a ruse.

Something was off.

"Hi...! James?" Of course, it was him, but what else could I have said?

As he stood to give me a hug, I prepared myself for a waft of cologne. But nothing. Except... Christ, was that Irish Spring? We had not spent a moment together, and I was already confused.

"Rachel! It's so nice to finally meet you!" His hug was so formal, neither warm nor abrasive.

But God, was he fucking polite. Who pulls out the chair for their date these days? But as he went to sit down, my Spidey senses went into high alert once more upon noticing his shoes. They were very nice dark brown cordovan leather loafers. They immediately threw me back to my childhood, eight-year-old me peeking from the top of the steps as my father talked with his friends, smoking Padron cigars, drinking Pappy Van Winkle, and every single one of them talking about where they got their cordovan leather shoes from. James' shoes made everything about him seem much more intentional, wolfish, maybe even predatory. He was trying to understate everything about himself while giving anyone who would notice fair warning that he operates with intention.

"The calamari here is the best in Seattle," he says.

"Oh? Is this where you take all the girls?" I laughed in my most perfect 'admire my jawline' laugh, and this fucker doesn't even look up from his menu.

After a pause, his completely ordinary lips parted to one side, and he smiled, looked up from his menu to me, and said, "This is where I took your friend."

"Ok..." I thought, “It's probably best that I check out and see if I can get a nice free dinner out of this.”But you know what... I just couldn't help but double down. He was not catching me off guard. I'm the one keeping him on his toes.

"Well, from what I understand, you didn't fuck her after coming here, so you might want to think about switching up your game." God, that sounded mean... Hopefully, it came off as playful… as I intended.

Immediately, his expression turned sheepish, "Well, I only went on that date with her to get to you."

Cheesy, but I gave it to him.

Before I even looked at the menu, the waitress came up and poured a glass of water for us.

"Do you know what you would like to drink?" Why did that question always seem like a challenge?

He asked me, "Do you know what you want?"

I felt my typical rum and sprite was a little too mundane. Cordovan leather shoes... Who was this guy?

"Do you have Pappys?" I asked.

He perks up.

"I'm sorry, we don’t." Her rehearsed expression of sorrow was blatant. I felt James’ gaze upon me in expectation of what I thought to be second best.

"No worries. Either Blanton's or Bib and Tucker then, whichever is cheaper," I said.

"That'll be the Bib and Tucker today," She smiled, "And for you, sir?"

"I'll actually do the Blanton's." A satisfied smile was packaged with his delivery.

"So, you're a bourbon girl?"

I've always hated being called ‘girl.’ But the battle against what I felt was a pejorative, and I felt tired at this point, and I certainly didn't want to take it up at that moment.

"My dad and his friends would always talk about what they considered the finer things in life. So, it was inevitable that I picked up a few things along the way. But one can never go wrong with a good bourbon."

"I completely agree," he replied. "And thank you for choosing the cheaper option. After trying to order a $100 shot, most women aren't that considerate."

And this was the problem. The sarcasm seemed like bait. But those shoes threw everything off. Was he genuinely grateful? I wished I could have seen his car. I did not want to judge him by it, but to provide a deciding context clue on how I should respond. Going with my gut that this is the first and only date, I laid it on thick.

"Well, if you're looking for something longer term, you’ll have to get used to splurging on the finer things when we go out."

I beamed my most playful smiles, not too aggressive but noticeably not as cheery, and he retorted, "Ok, so you're the kind of person that likes to be in control."

"Doesn't everyone want control?" I asked.

"Not me," came his response as he leaned back, stretching, and looking out the window at whatever he was pretending to look at before. "I'm very much a go-with-the-flow kind of person. The universe allows you to take control when it serves you and leaves it up to you to let go when it doesn't. The key is being able to feel what is right and when."

Was he too metaphysical? Is that why Mary couldn't go for him?

"Ok," I tried to reign it in, "how about on first dates? Don't you feel like you need to exert some sort of control? Over the experience, the location, the interaction, first impressions?Something...?"

"Nope," his calm response annoyed me because I assumed he was lying. "I am a victim in all of this and perhaps even an unwilling participant. Look at the shirt you're wearing. I appreciate the display of supple and gorgeous cleavage, but I don't know how you want me to react to that. And the obvious mismatch of a black bra under a paper-thin white blouse? You're not saying, 'Look, but don't touch.' You're saying, 'Admire this shit and pray you get lucky.'"

Well, I supposed he wasn't wrong. "Alright then, do you feel lucky? Punk?"

His gaze into my eyes widened. I swear that if I didn't know any better, I felt his erection grow from across the table. Was that crazy? Could you feel the energy of a hard-on? Its presence? Is there a feeling of spatial displacement caused by its increase in mass?

"I've never met anyone who could quote Dirty Harry." He leaned forward with a soft look on his face. At this point, I hated how he always seemed to challenge me.

"Well, don't get too excited. I've seen the movie once when I was seven or eight, and that's the only line that made it into pop culture." Why was I getting flustered?

A well-timed interjection from the waitress came as she dropped off our shots. "Do you know what you want to eat yet?" She asked.

James responded, "I know what I want to eat, but I don't think the lady has had a chance to look at the menu."Interesting phrasing.

"Alright, well, I'll give you two a few more minutes to figure it out then! By the way, the Ferris wheel next door was closed for about 6 months, and was reopened today. So, if you guys want to see the cityscape after dinner, that might be a fun option!" She left after we politely waved our "thank you’s.”

"Well?" He asked, diverting his gaze from me and opening the menu. "What do you fancy?"

"What do I fancy?" I laugh as I open my own menu. "Are you English all of a sudden?"

His matter-of-fact personality was evident at this point.

He responded, "I just want to know what you feel like putting in your mouth."

Sly bastard... Why did that literally make my pussy feel like a warm hug?

"I don’t know where you're going with that, but how about we start with these fine bourbons?"

"Cheers to that!" He said. We clink glasses, and both of us take only a moderate sip.

I continued, "I'm surprised you're not like the regular dudes. I thought you were going to  take it down the hatch."

"I thought the same of you," He responded with a laugh. I was glad he didn't notice that I measured his approach and would shoot it.

"So, what do you think about the Ferris wheel? It seems like it could be a fun option." He asked.

"I don’t know," I responded, "heights make me nervous, and doing that right after dinner might be a little more than we bargained for."

"Well then, let’s do it before dinner." He retorted.

"Right now? Don't you want to enjoy these fine bourbons?"

"We can finish these quickly, go, and then come back and eat. It shouldn't take that long. If you've never been on it,  I promise you an unforgettable experience." Again, a wolfish grin crept across the corners of his lips.

"Is that right?" I paused as I observed calmly the hopeful look in his eyes. Wondering what he had up his sleeve and not one to turn down an opportunity for spontaneity, I accepted."Ok, let’s do it."

He quickly left a $100 bill on the table and extended his hand to me as he stood up. Of course. As we left the restaurant, he moved my hand to the inside of his elbow so I couldhold onto his arm. Simultaneously, he assured our bewildered waitress that we would be right back.

There was no line, presumably because business only picked up after the closure. We got into our little gondola, and he told me, "You'll want to stand on this side to see the city." While a textbook move, the pressure of his hand on my wait to forcefully yet gently move me was… comfortable.

I did as he instructed and leaned against the railing to watch us rise over the city. And it didn't take long for me to guess what he was up to as he stood slightly to my right and behind me. His right hand grabbed onto the rail, touching my right hand. And his left arm wrapped around me to grab onto the rail on the other side of me. "You know, if you want a kiss, we're facing the wrong direction," I said when suddenly I felt  he was shaking. I turned my head to ask, "Are you cold..." The look in his eyes shocked the hell out of me. Never had a man's piercing gaze penetrated so deeply into my soul. Everything was clear. His deep brown eyes looked down at me, through me, and into me. A look that completely disarmed me complimented me and made me ashamed. It was narcotic. And no sooner had I been dazed by his desire than I felt his true intentions rubbing against my ass.

"Just look, enjoy the view." He shakily whispered. My free will degraded into obedience by what seemed like a tangible force of will. I should say no... right? His dick felt like a metal pole against my ass. I should stop him, maybe... He pressed it into me like he assumed I would take it. I'm not going to let him fuck me in the first 20 minutes of now... Why was I breathing so heavily? Why could I feel my pussy ignite into a wet fireball of unwanted lust? Why did I want to do exactly what he said?

With his forehead, he pushed my head into that glass. As I felt him take a hand to hike up my skirt. The up motion of the effort was matched with a flawless down motion of him unzipping his pants.

"You can’t..." It was the strongest protest my breathy voice could muster.

He pushed his head against mine harder as a punishment.

"I told you to enjoy the view." He reiterated.

And it was then that I felt it. If it was a metal pole before, it was now the hardness of a diamond as he used his dick to move my panties aside.

Apparently, I tried again, "You're not even wearing a condom." Why did I sound like I had just run 5 miles?

He put the head inside of me, and I grimaced in shame at what I was letting him do.

"This is going to hurt a little bit," he said as I felt him arch his back, a slight relief of pressure from my head that lasted about half a second as he thrust his entire cock into me. I wanted to cry from the disgusting pleasure as he hit my cervix head-on. I almost came instantly, as I’m sure he lifted my entire body off the ground with that thrust.

"You're a fucking asshole." That really put him in his place.

He started going at me like a mindless monkey. He reached across my chest and inside my bra to squeeze a nipple between some knuckles as he shoved his monstrous cock in and out of me. Almost every time, pounding my cervix head-on. I couldn't take much more.

The whole ordeal could not have been longer than 5 minutes before he squeezed the living hell out of my tit and shoved the head of his cock right up against my cervix, and groaned deeply as he held it there and began cumming inside of me. I couldn't remember if I told him to pull out, as I felt a new warmth coating my insides. I didn't want him to pull his cock out. He had broken me in so well by that point...

After several seconds of processing and catching our breaths… "I'm going to take my dick out of you now, and you're going to have to bring your legs together real quick. I don't want any cum on my shoes."

Fucking dick.

As he pulled his thick cock out of me, I could feel his cum begin to run out of my pussy, and my instinct was to panic at my disobedience. But there was nothing I could do. He left my pussy wide open, and it was all dripping down the inside of my legs. He stepped away as he put his cream-covered dick back into his pants. I arranged my panties as best I could and prepared myself for the insane amounts of shame I was going to have to endure walking back into the restaurant and into the bathroom with what seemed like a pint of cum running down the insides of my legs.

The gondola was reaching our exit as he interlocked his fingers with mine. He gave me an endearing smile and asked, "So, where are you from?"