Night Drive
Part 1: Transformation
“How do u feel knowing ur such a slut ur driving an hour to take fat cock?”
My hands tightened on the steering wheel as Daniel’s message lit up my phone. Part of me still couldn’t believe I was actually going through with it.
My heart fluttered. I looked over at my bag in the passenger seat. Inside was everything I’d need for the night: a wig, some makeup, and black lacy lingerie, just like Daniel had asked for. That night, I wasn’t simply driving an hour to get fucked—I was venturing into my first sexual encounter as a crossdresser.
About a minute passed before I managed to text Daniel back.
“I absolutely love it.”
***
When I pulled into the motel’s parking lot, the night sky was thick and silent, except for the faint rush of freeway traffic somewhere out past the streetlights. The parking lot was mostly empty, which brought a slight sense of relief to my ever-growing mix of nerves and excitement.
“I’m here,” I texted Daniel. “I’m about to check in.”
Yes, I really was here. An hour away from home, in the parking lot of a cheap motel, all for a man I only knew through pictures and videos. Daniel had actually wanted to fuck me in my car, but I insisted on getting a room. I wanted privacy—the space to transform myself, to greet Daniel in a wig, makeup, and black lace. And I wanted to finally see him in all his glory, especially that big, beautiful cock, which I’d been obsessed with for months.
***
I first messaged Daniel on Grindr not long after I’d figured out how to use filters to sort profiles. One slow morning at work, my grid was full of young tops when I came across his profile—almost by chance, since he didn’t have a picture. What caught my eye was his profile text: Daniel was hung (he claimed his dick was a thick 7.5 inches), and he was into fucking women, femboys, and crossdressers. I wasn’t any of those things, but his preferences felt like a reflection of the kind of man I’d always secretly desired. So I messaged him and sent a picture I’d taken of my ass in the shower.
He replied a few minutes later, sending a picture of his cock. And I just stared at my phone, breathless, yearning, spellbound—unable to look away. Despite its thickness and length, his cock stood straight out, almost perfectly horizontal except for a slight curve. The head was plump, and the skin of his uncut cock was pulled back, gathering firmly at the base of the head. His balls hung low and heavy. All of it—adorned by a tangle of pubic hair I could almost smell through the phone.
Then his next message appeared on my screen: “U fem?”
“No,” I replied, “but I love to be submissive.”
***
Checking in was about as uneventful as I could have hoped. No “What brings you into town?” or other small talk. I figured the staff at these motels are probably used to seeing middle-aged men checking in late at night by themselves. Still, I wondered how many of those men come here not to fuck, but to be fucked. In lingerie.
I quickly walked up a set of concrete steps to the second floor and made my way down a narrow walkway to my room, which overlooked the parking lot. The room, which I’d booked less than an hour earlier, was a double: two queen-size beds with white comforters, burgundy carpeting, and a large, well-lit bathroom.
As I unpacked my things, my phone lit up with a new message from Daniel.
“Let me know when ur ready.”
***
I had crossdressed for Daniel before, but only through Snapchat. During our first exchange on Grindr, after he’d made it clear he was exclusively into femininity, he told me he might be down to fuck me—but only if I wore a wig, makeup, and lingerie. The idea had never really crossed my mind, so I was surprised by how instantly and intensely I was turned on by the thought of giving up my masculinity for the pleasure of a younger, more virile man.
Daniel was a construction worker, in town temporarily for a job. I couldn’t let go of him—or the potential thrill of dressing up for him and getting to see his perfect cock in person—so we added each other on Snapchat. Soon, we were regularly sending each other pictures and videos: his cock, my ass.
It took a few weeks before I built up the courage to order my first pair of panties—a red lace thong, skimpy and delicate, that hugged me in a way nothing else ever had. And Daniel went wild for it. It wasn’t long before I had a hidden stash of thongs in different colors, which I’d secretly slip into—at first only for Daniel, but eventually for other men who, like him, took pleasure in emasculating and dominating lesser men.
***
I stood in front of the bathroom vanity, the harsh white light buzzing overhead. My hands trembled a little as I fitted the wig onto my head, feeling the tight grip of the adjustable straps settle just above my ears. Wavy brown hair spilled to my shoulders, the center part falling forward to frame my face, hiding just enough. I barely recognized myself.
It had taken me months to buy this wig. Every step, every little purchase felt like a deeper surrender of my manhood—an offering to Daniel, to a version of myself I was only now becoming.
I glanced down at my body: sheer black pantyhose hugged my legs, a subtle floral pattern winding high across my thighs. The lace thong was a constant reminder, the back riding snug between my cheeks, the front holding my helpless bulge in a soft prison of mesh and lace. My black blouse fit snugly, stretching just enough over my chest, cut square across the bust.
My makeup was shaky, but serviceable. Red lipstick, too bold and a little uneven; foundation that barely hid the shadow of my jaw. A touch of blush, mascara, and eyeliner—enough to blur the line between who I was and who I wanted to be.
I picked up my phone and typed with trembling fingers:
“I’m ready.”
The words lingered on the screen. Then, three little dots appeared—Daniel was already typing.
“Omw.”
