One Night with Becky: Chapter 6

The night with Jenna had been… awkward. There was no other way to put it. It wasn’t her fault, not really. She was sweet, open, and clearly trying just as hard as I was. But the whole thing had felt like two mismatched strangers fumbling their way through a bad date—the kind you would see on some pathetic reality show about virgins dating or something. Our conversation never quite clicked. Our movements didn’t sync. And when things moved to the bedroom, it was just… bad.

I tried to convince myself that I just wasn’t going to recreate what I had with Becky. Or, if I did, it wouldn’t be with some random trans chick. I wanted to think that the spark I had with Becky had nothing to do with her being trans… but I knew that just wasn’t true. Because whenever I thought back to that night, her ‘trans-ness’ was the first and most prominent thing that I would think about. Then, I would start to think about having a similar encounter with a biological female, and the fantasy was just so lacking.

I hated to admit it, but the trans aspect of Becky was such an important ingredient in what made things so exciting. 

So I kept trying to find a similar girl to fill Becky’s shoes. 

But nothing happened.

Nobody fit the bill. I tried chatting with a few girls that I matched on Tinder, but I just couldn’t muster up that same enthusiasm. For the first time in my life, I was starting to wonder if I was doomed to settle. Now, I knew what ‘the best’ was, and that just made everything else seem so… pointless. 

I quietly ‘unmatched’ with the few girls that I’d been casually chatting with. They weren’t Becky. 

I was back at square one. Again.

The void that Becky left in me still ached. And I hated myself for chasing it like a drug—searching for that same high, thinking I could recreate something that had never truly belonged to me.

But I didn’t stop trying.

I went on another date a few days later. Her name was Lexie, and her pictures had been stunning—flawless skin, sharp cheekbones, big doe eyes. I’d been nervous, but excited, wondering if maybe this one would be different. She was so spunky when we chatted, but so hesitant to actually meet. I kept insisting that it would be more fun to meet up and chat in person, but she always had an excuse as to why she couldn’t—until finally I talked her into meeting up. 

She was already waiting at the café when I arrived. And I knew, instantly, that I’d been catfished.

Lexie looked… completely unlike her photos. 

Not even close. 

She had used some kind of AI filter—one of those uncanny tools that smooths skin, reshapes bone structure, and basically builds a whole new person. Maybe it was a feminization filter, because the cutesy feminine traits from her pictures didn’t exist; they couldn’t exist with what she had at her disposal. She looked older in person. Rougher around the edges. And the discomfort on her face when she saw my surprise said everything. 

But I tried anyway. I tried to see past the fakeness of her profile, hoping that it was just an innocent faux-pas—a little low-self-confidence slip. 

We tried to talk, to push through the awkwardness. But it hung over the table the whole time. I was polite. She was too. But there was no recovering. Twenty minutes later, I feigned a work emergency, and I snuck off as quickly as I could. 

Back at home, I sat on the couch in silence, staring at the ceiling like the pattern of popcorn on the ceiling was hiding the answers to my problems. I was tired… Tired of pretending… Tired of being polite. I was tired of feeling like I was chasing something that didn’t exist.

Or maybe it never existed. I sometimes found myself wondering if my one night with Becky had just been a weird dream. How could I prove that it happened? I didn’t have any photos of us together—just that DM from Red Girls Media telling me the date was scheduled. 

I fell onto my bed, almost ready to give up. I found myself wishing I would have never found Becky—or that I wouldn’t have enjoyed our time together. But I just couldn’t stop thinking about how new and exciting it had been with her…

New and exciting…

And that’s when the thought hit me.

Maybe I just need to get this out of my system.

Maybe that was the problem. It was so new and exciting… but maybe I could make it less new and less exciting by just… numbing myself to it. 

Maybe I could burn this thing out of me. Fast. Clean. Like ripping off a bandage.

I opened my laptop and hesitated—my hand hovering over the keyboard like I was about to commit a crime. And… well, I suppose I was.

I typed slowly: escorts near me. Then added the word I’d been dancing around for weeks: trans.

A dozen sketchy-looking sites popped up, each more taboo than the last. I clicked on one that looked vaguely reputable, and instantly, I was bombarded with photos—some real, some obviously fake, and all of them screaming you shouldn’t be here.

But I didn’t close the tab.

My fingers hovered, trembling, over the “Trans” category.

This was pathetic. This was desperate. This was the bottom of the barrel.

And still, I clicked on the first profile that caught my eye. Her name was Nova, and her photos were stunning, but I knew that photos could be deceiving, so I didn’t get my hopes too high. High cheekbones, full lips, and a figure that was just chunky enough to make me want to latch onto her. 

I sent her a message, and within minutes, she responded with a price and a location: a very formal-seeming business transaction. There was romance-confusion like with Becky, no pretending like there was any chance of this turning into ‘something’. I agreed without hesitation, my heart pounding… was it excitement, or was it dread? 

An hour later, I was standing in front of a nondescript motel room, my palms sweating and my mind racing. I knocked, and almost instantly the door opened to reveal Nova. 

I was surprised by her authenticity. The pictures were actually quite accurate. She was pretty: tall, with long legs and an almost-intimidating confidence. She had the cheekbones and the big flashing eyes… though it was a bit more obvious in person that her features were the product of surgeries. The full lips looked much stiffer in person—and the breasts were almost unnaturally round seeing them up close. But her makeup was flawless, and her dress hugged her curves in a way that really made her look feminine.

A glimmer of hope crashed like a wave against my chest. Maybe I could get what I needed from Nova. Maybe she could replace what I was missing with Becky. I could save some cash each week and meet up with Nova, getting my fix of… well, girls like her.

"Come in," she said, her voice smooth and inviting, and delightfully feminine. I stepped inside, and she closed the door behind me, locking it with a soft click. The room was dimly lit, but musty as you would expect from an old motel room that had an hourly rate. 

As I turned to face her, I felt a strange detachment, as if I were watching myself from outside my body. She was smiling at me, but I could see in her eyes that this was all business; she was thinking about money… or maybe she was just wondering how long this would take so she could get back to doing her laundry. There was no romance here.

She moved closer, her hands reaching for my belt. I guess we were skipping the chit-chat. I guess we were going right into it. The clock had started. I let her reach for me, my body responding automatically, but my mind was elsewhere. She led me to the bed, her movements almost seeming rehearsed, as if she’d done this a few times already that evening. 

We undressed each other slowly, and I tried to focus on the sensation of her skin against mine, the softness of her lips, the way her body moved with mine. But it seemed like the more I reached for it, the more it slipped through my fingers. 

She wasn’t Becky.

But I didn’t need Becky. Becky didn’t want me. 

The room was weirdly silent. I was tempted to ask her to put on some music, to kill the awkwardness. 

I closed my eyes, trying desperately to lose myself in the moment. Nova's hands roamed my body, tracing every inch of me. It felt nice… really nice… But it wasn’t quite enough. Her lips found mine, and I kissed her back, even sharing tongues for a moment, yet it just didn’t seem romantic in the slightest. It almost felt… clinical, like it was another step in some sort of check-up. 

She pushed me down onto the bed, her body pressing against mine, and I could feel the hardness between her legs. She was hard, but it didn’t seem like arousal. Her tired movements didn’t suggest arousal. She had taken some sort of little blue pill to make it hard like that. And why was I surprised? It was her job. Becky had probably done the same.

She guided me onto my hands and knees, her hands gripping my hips firmly. I felt her cock, thick and hard, press against my fuck hole, and I gasped at the sensation. Nova pushed inside of me slowly, inch by inch, filling me completely. She was big. Not Becky big, but big in her own right. I moaned, trembling slightly as she began to move, her hips rolling in a rhythm that was so perfectly practiced that it seemed fake.

All of this seemed fake. 

But it was fake with Becky too… she admitted it to me. So… why did this feel so different? Was Becky just better at being fake? 

I tried to push the thoughts of Becky away, to focus on the present, on the woman behind me, her body glistening with sweat, her eyes locked on mine in the reflection of the mirror ahead of me. But Becky’s voice in my head just wouldn’t fade away… Her sweet moans… her whispered pillow talk. Nova's touch, her kisses, her whispers—none of it could fill the void that Becky had left.

Maybe it wasn’t the physicality that I was missing. Maybe it was something deeper: a feeling that Nova just couldn’t provide with her services. And maybe Becky had never provided it either; maybe it was my own stupid naivety that provided me that fleeting feeling.

As Nova pounded into me, our bodies slapping together, I could feel the pleasure building, inching me closer and closer and closer to my climax. It felt good, don’t get me wrong. I could feel her veiny cock sliding in and out. I could feel her fat, swollen tip. I could even feel the slickness created by her oozing pre-cum. But… something wasn’t quite right. 

“Want me to jerk you off?” she asked, her voice still feminine.

“Yeah,” I said, hoping a bit more stimulation would make things different somehow. She reached around and gripped me, stroking expertly… but still, something was off.

We reached the peak together. When I felt her spilling into me, I gushed onto that motel bed, groaning. Nova collapsed on top of me, her body warm. Then, a moment later, she peeled herself up and checked the time, as if to see if we had gone over so she could charge me more. Saying nothing, I went for my wallet and quietly put the agreed-upon cash on the dresser.

Then, I got up, dressed quickly, and left without a word. As I walked away, I felt a deep sense of dissatisfaction, a gnawing ache inside of me telling me that I would never have that satisfaction that Becky had given me. Nova was beautiful, skilled, and everything I thought I wanted. But she wasn't Becky. And no one else would ever be.

Hell—Becky probably wasn’t even the Becky I had built up in my head. I was chasing something that didn’t exist—and never did exist. I knew it, but that didn’t change anything in my mind.

Back at home, I sat on the couch, my mind a whirlwind of conflicting emotions. I had tried to fill the void, to numb the pain, but all I had done was make that longing worse. Becky was still there, in my thoughts, in my dreams, a constant reminder of what I had lost... or maybe what I never had.

I fell onto my bed, exhausted and defeated. Maybe I was doomed to settle, to spend my life chasing that ‘ghost’. I knew that I needed to let go, to accept that some things were meant to be fleeting, no matter how much we wished otherwise.