Asey's Conundrum

I met Kasey at a truck stop. I was getting fuel and she was getting busted for shoplifting. I intervened, suggesting to the manager that she was with me and that I would cover her expenses.

"Listen, Mister, I can see you're trying to do a good thing here, but I saw you come in... by yourself. Nevertheless, I'm willing to forgo pressing charges if you take her with you and I never see her in here again. But I'm tellin' ya, you'd do well to leave her be and go your way. This kind's always trouble. I've seen 'em time and ag'in."

I had a gut feeling that he was right and that I'd probably regret it, but I had been on the road for a long time and wanted company, if only for a few miles down the road. I didn't know then that she was beautiful. She was wearing a ballcap with her hair tucked up underneath, baggy cammo pants and an olive drab army jacket and backpack. She didn't have makeup on and didn't look especially appealing under the circumstances. She had a hard look about her. But like I said, I was hungry for company.

"Your call," I told the girl. I didn't want it to ever be a thing where she claimed she was forced. Since it was obvious the manager saw through my scheme, it was no longer important to pretend she really was with me.

"You a serial killer?" she asked me.

"Not yet," I grinned. It probably wasn't the best time for a joke, but I tended to diffuse stress through humor.

"Rapist?" she queried.

"Nope." I answered. "Liar."

For some reason, that caught her funny bone and she grinned back at me. "Let's go," she said.

I paid the manager and thanked him for his forbearance. He wished me luck and we left.

"You okay?" I asked her as we pulled out on the Interstate.

"I am," she answered. "Thanks for getting me out of that jam."

"My pleasure," I answered. "This time. But let's not have any more drama. I will never lie to you and ask that you will never lie to me. Deal?"

"You mean if I ask you if my butt looks big in these pants, you'll tell me the truth?"

"Even if it kills me," I answered, grinning.

"It just might," she grinned back. "Okay. I swear I'll never lie to you." Then she asked, "Are you really a liar?"

"No. Are you a runaway?" I shot back.

"Not technically. I turned eighteen a week ago. But I was when I left home."

"How long ago was that?"

"After graduation in June. I left and never came back. My stepdad was a dick."

"He molest you?"

"No, but it was only a matter of time, I think, until he got up the nerve. I wasn't waiting around to find out if he ever did."

"I'm sorry. It must suck to have to live in fear constantly."

"Yeah. I thought getting out of there would be the end of all my troubles, but it was more like out of the frying pan into the fire. Being out here with no one is almost worse."

"The world is a dangerous place," I reflected.

"Yeah," she agreed. "I've met some pretty creepy guys."

"Any of 'em rape you?"

"No. But I figured they would if I gave 'em half a chance."

"Men are pigs," I agreed.

"Not all of 'em," she said. "I've met some, like yourself, who've been decent."

"I don't know that I'm all that decent," I remarked. I knew myself well enough to know that I probably wasn't any better than most of the guys she'd run across. I had often chastised myself for the hold that a pretty woman had had on my motivations, and I didn't feel especially virtuous.

"Well, you may not think so," she argued, "but I've had occasion to interact with plenty of men during my month-long journey on the road. I figure you'd probably want to have your way with me as much as the next guy, but at least you have the decency to keep it contained."

"I suppose that's true," I agreed. "But honestly, I didn't really even consider your appearance at all. I was just hoping for a little company."

"I learned early on that wearing clothing that revealed my figure at all would lead to trouble. I go out of my way to not look appealing."

"Yet my damsel in distress radar was fully engaged."

"That's why I said you were decent," she replied dryly. "I'm not bragging, but I look pretty good in a cocktail dress, although I don't have the boobage some men seem so fixated upon."

"I've never been one for big boobs. I prefer smaller, rounder boobs, the perky kind," I answered without thinking that it might be a faux pas if hers didn't fit the bill.

"Mine are too small to be anything but perky," she said somewhat ruefully.

"My father always used to say that anything you couldn't fit in your mouth was wasted anyhow," I told her. It occurred to me that it was somewhat surreal to be having this conversation with a girl I only just met who was young enough to be my daughter. At thirty-six, I could have produced offspring that would be her age by now.

"Sounds like he was a smart guy."

"I don't know about that. My mom was small-breasted, so maybe that was just what he told himself to make himself feel better. I know for a fact that he liked big tits. And my mom was always envious at the way he ogled them."

"Okay, maybe he wasn't such a great guy after all," she said.

"Well didn't we already establish that men are pigs?" I joked.

"Right!" she chuckled. "What was I thinking?"

"Listen, as much as I like talking about tits with a young girl I barely know who's young enough to be my daughter, I'm afraid I have to change the subject." She looked at me and turned serious.

"I'm Kasey Stafford. I'm homeless, jobless, and penniless. I'm not on drugs. I'm not a hooker--at least not yet. And, since I'm being totally honest, I have no idea what I'm gonna do about it. I've just been living a day at a time. I just wanted to put some distance between me and Ohio."

"When was the last time you talked to your mother?"

"What? My mother? Why do you ask?"

"Well, I figure she's probably worried sick about you and might like to know you were safe."

"Am I?" She paused for an instant, "Safe?"

"Well right now you are," I answered. "But I can only speak for myself. Once you get back out there," I made a sweeping gesture at the windshield, "you won't be."

"Are you offering to let me stay with you?" The look on her face was ripe with expectation.

"Well, it actually never occurred to me that you might want to, but you're welcome to stay as long as you like--as long as you're honest with me."

"I promised to always be honest with you," she said solemnly.

"Okay, then," I said as the gravity of what just happened washed over me. And then I handed her my phone and said, "Call your mother."

I listened as she assured her mother that she was safe and traveling with a truck driver she met at a truck stop. The conversation was short and unemotional which surprised me. Kasey explained later that she had never really gotten along with her mother and when she brought up her misgivings about her stepdad her mother sided with him. It was then that she made the decision to leave.

We drove on without speaking, both lost in thought. I have to admit I was excited to have the company. My mind drifted back to our earlier conversation about tits, and I imagined how nice hers must look. My reverie was broken when she quietly asked, "You married?" I realized then that I hadn't yet told her anything about myself, not even my name. Yet, she'd agreed to hang with me. She was either very stupid or very desperate. I didn't think for a moment that she was stupid.

"Nope," I answered. "Divorced. She couldn't handle me being gone all the time. Took up with another fella."

"That sucks," she summarized. "Got kids?"

"Nope. She said she wasn't ready. I guess she just wasn't ready to have any with me."

"So, you want kids?" she pressed.

"Oh sure," I said. "But I've kind of given up on the idea seeing as how I'd need a wife and a home to raise them in. I've got neither one."

"I want kids," she said. "Three or four of 'em."

I didn't know how to respond to that, so I just said, "By the way, my name's Jack Riley. Well, technically it's Richard Riley, but the nickname for Richard is Dick, and that didn't set too well with me in school, so I started going by my middle name."

"You have a rough childhood?" she asked.

"Not really. My mom and I never got along well and my dad was a trucker and was gone a lot. And there was the Dick thing in school that I caught a lot of shit for. I wouldn't want to relive it, but I wouldn't say it was rough. We always had a roof and food on the table. It was okay." I glance over at her. "What about you?"

"Well," she began, taking a breath, "I didn't have anything traumatic happen to me, but my mother had me when she was only seventeen. The guy that knocked her up, dear old dad, bailed on her. Her parents kicked her out when they found out she was pregnant. She ended up in an unwed mother's home until she got back on her feet. I think she always resented me for ruining her life, like she didn't have anything to do with it. So, we were never close." She shrugged. "I was an only child on my own for as long as I can remember."

"It didn't surprise me that she took his side when I mentioned how uncomfortable I felt around her husband. And since he never actually touched me, I really didn't see what else I could do besides leave."

"Well," I said hopefully, "maybe things will start looking up for you."

"Maybe," she agreed. "If you still want me around now that you know I have daddy issues."

"That depends," I said, grinning. "How do you feel about spankings?" I joked.

"I'm not sure," she said thoughtfully. "I like having my nipples pinched, so maybe. We'll have to try it and see."

She read the surprised look on my face and said, "You're not going to pretend like you haven't thought about having sex with me ever since I told you about my tits, are you? After all, we're being honest with each other. Right?" She had me there. I told you she was smart.

"I thought about it, sure," I admitted. "I just thought it would be too good to be true, so I never let myself believe it would happen."

"Baby," she said, shifting in her seat to look at me, "when you picked me up at the truck stop you were a short-term solution. When you asked me to stay with you, you became a long-term commitment."

She pulled her hat off and shook down her light brown hair. It was then that I first realized what a lucky man I was. But I didn't know the half of it.

"Jack, I know I'm young and inexperienced, but I know a lot about sex--there's this thing called the Internet--and I am going to do my best to make sure you never regret bringing me aboard."

She was so earnest, so sincere, that it really touched me. I wondered what I did to deserve such attention from a girl who could probably have any guy--and much younger ones at that--that she wanted.

"I don't feel like I deserve that kind of devotion from a girl as young and pretty as you are," I told her. "I'm just being honest."

Far from being dissuaded, Kasey patiently tried to reassure me that I was as worthy as anyone, and probably more so, since she already knew I was a decent human being. She insisted our age difference was not an issue for her--because of her daddy issues, she preferred a more mature man. Finally, she divulged that she did find me attractive and had noticed me even before I rescued her from the manager at the truck stop. "In short," she concluded, "I'm going to be your personal fucktoy."

She sat back in her seat and put her hat back on. "But I'm going to need a shower before that happens. Which brings up the question, do you like your pussy hairy or shaved? Cause I could go either way."

"Uh," I stammered, still processing her earlier speech. "Neatly trimmed?"

"I can do that," she grinned. "And how would you like me to dress? I can do cammo and stay incognito, or I can go completely slutty, which I've secretly always wanted to do."

"Slutty?" I queried, unable to think of a better way to phrase the question. I guess I just wondered how she thought that would look.

"Sure. You know, like leggings or short shorts, tight thin shirts with no bra underneath, that sort of thing."

"You mean that's how you would dress all the time?"

"Well, not to go to church," she said, grinning, "but in general, yeah. Or would it bother you if other men look at me?" The question seemed to be something that she only just then realized.

"It will only bother me if you look at other men," I answered. "But is dressing slutty something you want to do for you or for me?"

"I've fantasized about it for years," she said, "in fact, it's making me wet just thinking about it. But I could never do it at home, around people I know. Now, I'm not likely to run into anyone I know or will ever see again, and I have you to protect me. And I though you might like it, too. But if you'd rather I just stay low profile, or be more modest, I will."

"Well, I'm fine with you dressing however you want. I've always enjoyed running across scantily dressed women. I'm sure I will enjoy seeing you that way. But as far as protecting you goes, I'm afraid they'd just kill me and take you."

"Great!" she said, her face lighting up. "I mean, that you're okay with me looking slutty, not the getting killed part."

I laughed. "I was pretty sure that's what you meant."

"So, whenever it's convenient to pull into a Walmart maybe I could do a little shopping."

"Well, I need to drop my trailer when we get to Lincoln. After that, we'll have the night to ourselves. We can get a room and some dinner. I'm sure there's a Walmart there, too."

"And I can get a shower," Kasey added. "You can wash my back, or anything else you want to," she offered, casting me a sensual look.

"I'm looking forward to that," I said. "I've never really had the opportunity to inspect and fondle a woman. I always thought it would be fun."

"But you were married, right?" Kasey asked with furrowed brow.

"Yes, but she was never that forthcoming where sex was concerned. We had sex, but it was always in the dark, do it and done. She was too self-conscious to allow me to gawk at her private parts in the light of day."

"Jack Riley, I'm just letting you know, explicitly, that my private parts are your private parts. You can see them or fondle them whenever you want. Anytime. Anywhere. You just have to be able to bail us out of jail."

"I don't deserve you," I said. I meant it. This girl was like a real-life wet dream who just dropped into my life. "How come some boy hasn't snapped you up before now?"

"Daddy issues, remember?" she answered with a sweet smile. "By the way, some guy did snap me up. His name is Jack Riley."

"Damn!" was all I could say. I still hadn't seen her naked, but I was enjoying the anticipation. And even if her appearance didn't measure up to the perfection conjured up in my imagination, I was sure that her attitude would more than compensate for any shortcomings. Then again, I thought, she did just say anytime, anywhere.

"Kasey, I would like to see you naked now. I was trying to be patient, but since you offered..."

"Sure, Jack. I was wondering what took you so long. I'm learning that you are not the master of taking subtle hints. I'll work at being more explicit."

Kasey unbuckled and stepped behind and between the two seats where there was a space in front of the sleeper. She shed the jacket, then pulled off a t-shirt and undershirt to reveal that she hadn't been wearing a bra. She really didn't need one. In my rear view mirror, I could see her small, pert breasts jutting out proud and round from her chest. Not very far, to be sure, but far enough to be recognized as the beautiful breasts they were. Her areolas were about the size of a quarter and her nipples pencil eraser hard. I also noticed she had hair under her arms. She had mentioned that shaving hadn't been part of her regimen while on the road.

I did my best to keep my eyes on the road while Kasey unbuckled, unzipped, and pulled down her baggy camouflaged pants, letting them fall around her ankles. She stepped forward, into my field of view, and the view of anyone fortunate enough to be able to see into my cab. The first thing I saw was the thick fur covering her lovely pussy. She spread her labia a bit, just to give me a glimpse of the pink in between. Her pussy was so wet it was positively oozing! Then she stepped forward a bit and leaned over her seat, exposing her gorgeous ass, spreading her cheeks to show me both her rosebud asshole and wet pussy. I was probably more particular about a girl's ass than any other part of her anatomy. Kasey's was damn near perfect. It was for sure the most perfect ass I would ever get this side of heaven.

"You have the most beautiful body I've ever seen!" I exclaimed after she sat back down in her chair, still naked.

"That's the kind of response that makes a girl really want to fuck her man," she said, spreading her legs and fingering her pussy. "That level of appreciation makes me happier, and hornier, than you can ever know. You keep that up, Jack, and we will have the love affair to rival that of Tristan and Isolde."

"Who?" I asked, feeling suddenly uneducated.

"A couple in a Medieval romance story," she answered. "Before there was Romeo and Juliet, there was Tristan and Isolde."

"That's good, right?" I asked.

"Well, kind of. Their love was intense, but complicated since she was married to someone else."

"O-kay," I acknowledged.

"I was emphasizing the intense, part," she said as she suddenly gasped in orgasm. I was driving, so I couldn't afford the luxury of watching her diddle herself except for furtive glances. "I so needed that," she said, still out of breath. "Is it okay if I get dressed now?"

"Absolutely. I didn't mean that you had to stay naked. I just couldn't stand the curiosity anymore."

Kasey got up and put her clothes back on, except for the shirt and jacket. Her undershirt was the ribbed variety, very thin and form-fitting. I could see her breasts clearly through the thin fabric.

"That was the first time I'd ever seen a girl play with herself in real life," I told her.

"That was the first time I'd ever done it in front of anyone," she admitted. "Did you think it was hot?"

"Yeah, I did. I just wish I hadn't been driving at the time so I could have paid closer attention."

"No worries," she said. "I'll be happy to give you an encore presentation whenever you want."

Then she leaned over and kissed me. It was a long, sweet kiss, full of passion. I felt a stirring in my loins. But before things could go further, my GPS piped up that our exit was ahead.

At the terminal, I dropped my trailer as directed and found the one I was to pick up tomorrow. Now we were free to pursue our own agenda until tomorrow.

We pulled into a Walmart parking lot and Kasey spotted a Goodwill store and asked if we could go in. Why would I object? She rifled through a few racks to find a couple pairs of jeans in her size but were too long. "Not to worry," she said, "These are gonna be cutoffs." She found a couple tops she liked, the sort with thin fabric that clung to every curve. That meant I would like them too.

We walked over to Walmart to pick up some other items. Kasey picked up some skimpy fabric booty shorts, a package of wife-beater tank tops, yoga pants and tops, some makeup, and toiletry items. I suggested she get a small bag to keep it in so that when we stopped for showers, she would have easy access to her necessities. We also found her a cotton/spandex bodycon dress that showed that she wasn't lying about her figure. Also, some sandals that matched the dress.

I tried to discreetly place a box of condoms in the cart, but Kasey noticed at once.

"Are you getting those for you or for me?" she asked, parroting my earlier query about her choice of apparel. "Because I'm perfectly fine taking my chances with you. You want babies. I want babies. Let's just let what happens, happen."