The Jockey: 14, 15, 16

In spite of its description as “Fiction,” this story is actually an embellishment of real experiences I had with a girl during my time on the radio. The first several chapters are absolutely true, save names and locales.




XIV. “Dean? How are you doing, Baby?” Ashley’s voice and a hand on my back.

Without actually thinking about it in my half-asleep malaise, “Good. How are you?” A kiss on my ear and I smiled. A sharp smack on my ass stung me into alertness as I jerked, turning to see Kim smirking at me.

“Good morning, pretty boy.” Pretty? I couldn’t recall ever having been addressed as “Pretty Boy” before.

I looked up at her as I finished turning onto my back. “Anyone ever tell you that you have the bedside manner of a porcupine?”

She put a hand on her hip and posed herself a diva. “I try.”

I looked back at Ashley to find her admiring me. My heart stopped again in her beauty, and I reached up my hand to stroke her water-streamlined hair, now slicked back against her head. She smiled bigger, and sighed, as Kim picked up my own dampened towel in lieu of her own cum-stained one, and dried herself as she walked into the house.

“We’re hungry,” she began. “We’re thinking pizza. Whaddaya think?”

I hadn’t had pizza in a while. “Sure.” Then I remembered where we were. “Do they deliver here?” I was unfamiliar with the dynamics of a gated home.

She smiled at my inexperience. “No. We’re too far out. We’ll have to go get it.”

Having delivered pizzas myself a few years before, I suspected that it also had something to do with the fact that people with money don’t tip. A guy in a trailer park will slip you a fiver, but people in houses like this one want exact change, and I despised them for it. Then I remembered that some money couple’s hot young daughter had just jerked me off beside their pool, wiped my cum from her arm with their plush towel, behind their million-dollar home, and I found some closure.

“Do you want me to go with you?”

“Of course, silly.”

I contemplated the scenario of leaving to go get pizza, and decided it to be an acceptable one.

“Okay, let me get up and get dressed.”

She smiled gingerly. “Oh, you don’t need to get dressed; you’re not getting out of the car.”

I stopped. “You’re kidding, right?” She couldn’t possibly be serious.

“Nope,” she said smugly. “You don’t need clothes if you stay in the car.”

I had to object. “Actually, I’m pretty sure I do.”

Ashley started at me intently. “Are you sure about that, Dean?” I fucking hated that. I couldn’t tell if she was threatening me or not, and it made it hard for me to like her. As I was deliberating, her expression changed to cheeriness, and she added, “Think about it, Sweetie, why would you need clothes? No-one will see you. I tell you what, I’ll get Kim to take the Land Rover; its windows are tinted. How does that sound?” It was less of a question and more of a request for confirmation.

I knew I wasn’t going to win, and the Land Rover sounded much better than Kim’s wide open Subaru. “Okay.”

“Great!” She asked me what I liked on my pizza, and I told her that I was easy to please. She giggled as she went to dry herself. When she started into the house, she tossed me her towel, and I dried myself before following her. I noticed that the clothes I had been wearing earlier had disappeared, and I was unsurprised. We found Kim in the kitchen, dressed again and brushing swimming tangles aggressively from her hair.

“Pizza’s a go,” announced Ashley, as Kim winced at us in pain, finishing her bout of brutality with the brush and setting it on the counter. I asked her if I could use it for a moment, and she made another jab about the length of my hair before giving permission. Ashley smiled at out exchange, passing out bottles of water she’d procured from who knows where, then said to Kim, “Okay, you call it in. I’m going to get dressed,” and walked hurriedly to the stairs, leaping up them in a moment. She was amazing.

Kim watched me and my hair for a few moments uncharacteristically in silence. I returned the brush to her when I was done, and she asked, “Why is your hair so long?”

I explained to her that I’d had short hair all my life until a couple of years ago, due to various reasons, and when I’d finally had the option of letting it grow, I’d gone with it, just to do it. I’d grown quite accustomed to it in recent months, as it had finally become long enough to become manageable, so I was not keen on cutting it.

She went silent again for a few moments before reaching for the phone and asking, “So, no clothes?” She had apparently noticed that I was not dressing for our expedition out to retrieve the pizza.

“Nope,” I responded, my dissatisfaction evident in my tone.

Kim ignored my delivery as she was dialing. “Didn’t think so.” She smiled at me a different kind of smile, and I felt she was beginning to warm up to me.

I asked her where her bathroom was before disappearing down the hall. I reentered the kitchen a few minutes later to find them waiting for me. Kim had redressed in her earlier clothes, and was now sporting a cap, and I thought the look suited her. Kim said, “Okay, let’s go,” and we shuffled through the den back into the garage.

As we piled into the Range Rover, Ashley and Kim in the front and me in the back behind Kim, she declared, “Dean, if you stain my mother’s seat with anything, so help me God, I’ll fucking kill you.”

So much for her warming up to me. “Yaz’m,” I replied, trying to lighten her mood with humor. Ashley chuckled, but Kim was unaffected.

“I’m fucking serious, Dean. Don’t fuck up my mother’s upholstery.”

A more direct approach was apparently required. “Got it,” as I shut the door, and remarked to myself what a shame it was that such a beautiful girl as Kim should have such an abrasive temperament.

The garage door opened, and Kim carefully navigated us onto the street. Ashley and Kim started talking about something that sounded school related, and I had no frame of reference, so I tuned them out, watching the scenery go by as the little boy in my head kept tugging on his mother’s arm.

Momentarily, I had stopped thinking about the enjoyment of my time with them, and was seriously trying to think of a way out of my mess. Before even considering the possible danger of opposing Ashley, I had to consider the fact that I was naked, in a strange car, soon to return to a strange house. Once I was back in the house, if I could manage to get my clothes back, I still had no idea how to get to my car.