On The Road Again Pt 01

I must give credit to my editor SlaveGirl70. She was a vital contributor to this story, and corrected many blunders on the part of the author. I can't thank her enough.

Daunti

*****

On The Road Again

An Exercise in Middle Aged Fantasy

Tim had been driving alone for nearly six hours. He'd stopped for gas and a cup of coffee about thirty minutes ago, but as usual his mind tended to wander when there wasn't anyone around.

Three A.M. on a Friday morning, forty miles south of Kingsville, Texas on highway 77 south. Why am I here? I'm here because I'm headed home from a meeting in Austin. I could have stayed over but if I get home now I'll have all day today off and no one to answer to. If I have breakfast and stall a little, my wife will be at work when I get home, and I can have the day to do what I want. Not that I don't like my wife, but when we're both home during the day, even on the weekends, she's always demanding my attention and I get bored. Beside, I've been true to her for twenty-two years, but lately I've been wondering what it would be like to pursue a young, slender, girl with firm, perky tits, silky skin and a great figure. I've never had one of those, and it's tempting, but the problem with that is that I wouldn't have the foggiest notion how to approach one. Do I pick one out in the supermarket and get myself arrested for propositioning her on the spot? Probably not a good idea... Go to a bar and try to pick one up? Even if I could get enough time out of my wife's sight to go to a bar, I can't imagine a twenty something year old taking me seriously. There's nobody at work for me to hit on; they're all either as old as my wife, or fat, or ugly, or as stupid as a cow, or all of the above. I can always hope the boss will hire a looker but there's not much chance of that. His wife would kill him if he did, and he knows it. Even if he did hire one, what would she want with a forty-year-old fart like me? And the worst problem of all is that it's wrong. I made my choices and I can't go back on them now It's fun to think about but I'll never do it. Well, so much for that idea.

Forty miles south of Kingsville on highway 77 there was nothing but a fence on each side of the divided highway, and beyond the fences, sagebrush and cactus. There wasn't any civilization for another thirty miles. It's a desolate stretch of highway that was even more so at three o'clock in the morning.

Tim shook his head to try to wake up. It was always dangerous on this stretch, especially if you're fatigued. It tends to lull one to sleep.

Then he saw it: a red sports car stopped just off the road, on the shoulder, with the emergency blinkers flashing and the hood open. It looked like a Jaguar convertible.

Should I stop? Good question. If I was stranded out here at three in the morning I'd appreciate some help, but I'm alone. On the other hand, it doesn't seem likely that somebody's going to set a trap at this time of night, when there's not much traffic, and it's as apt to yield a highway patrol trooper as an unsuspecting victim. Of course, the Jag is good bait...

Tim slowed down and pulled off the road behind the red Jag. He put on the emergency flashers and turned off the headlights, but left the parking lights on. Just as he opened his door to get out, the driver's door of the Jag opened, showing a shapely female leg.

As she got out, the only thing he could tell about her in the dim glow of the parking lights was that she was trim and wearing shorts and a halter-top. She eyed him with some hesitation, cocking her head as he walked toward her, but finally took a step toward him and said, "Thanks for stopping. I was afraid I'd have to spend the whole night by myself out here in the boonies. Being a city girl, I don't think I've ever seen any place as dark and empty or as frightening as this is."

"Hello, I'm Tim Henry. What happened?"

"Hi, I'm Jessica Long. I don't know what happened, the damned car just quit."

"Nice to meet you, Jessica; it's a shame it has to be under these circumstances. I'm sorry I don't have any tools along on this trip, but it wouldn't help much if I did. With the new cars these days, it takes a whole shop full of equipment just to find out what's wrong. The best I can do is to offer you a lift. Where are you headed?"

"I was on my way to Padre Island for spring break."

"Well, what would you like to do? We can call someone to tow your car, but not till tomorrow. There's no cell phone service this far out, so we'll at least have to go to Raymondville. I'm sure there's no towing service open overnight there. It's just a small town."

"Mr. Henry, if you can just get me to someplace where I can get a room, I'll call my insurance company in the morning and they'll get the car towed to a dealership. It's still under warranty so it'll get fixed, but I'll need a rental to get on to Padre Island. I'd hate to miss even a day of spring break just because my stupid car broke down."

"Please, call me Tim. May I call you Jessica?"

"Actually it's Jess to my friends, and I'd say helping me out like this makes us at least friends."

I wonder if he's married. A little old, but then I haven't tried an older man yet. If he cheats he may know how to supply orgasms...or maybe not. Let's see what happens.

"Great, Jess. Raymondville is the closest town, but I'd suggest you stay in Harlingen. It's only another twenty miles or so down the road from Raymondville and it's on the way to the island. A lot more facilities there, and a better choice of lodging and car rentals, unless you'd rather go on to the island tonight. Where are you staying for spring break?"

Jess hesitated, wondering whether she should tell him anything more. She'd been burned before by men who seemed nice and safe, and she didn't want her vacation ruined by some snake that just wanted to use her. She picked her partners, not the other way around. "Tim, I really appreciate your helping a lady in distress, but I'm cautious about inviting strange men into my personal life. I'll be happy to pay you for your trouble, but I'd like to keep it on a 'strictly business' basis. My reservation is for today, but I can't check in until three o'clock this afternoon, so I'll have some time to kill. How far is Padre Island from here? Is it on your way?"

Tim understood her reluctance to get too chummy, so he answered, "It's a couple of hours from here. I live in Harlingen, about half way to the island from here. I'll be happy to keep my distance, but I'm afraid you'll have to either get in my car or wait here until I can send someone to tow your car and get you to civilization, which is apt to be several hours at least. I assure you I'm not a sexual predator or anything else dangerous, and you'll be quite safe with me. On the other hand, out here in the middle of nowhere isn't a very safe place to be. I'd suggest that you let me take you to Harlingen and see if you can rent a car at this time of night. I seriously doubt that you can until morning, but I'm not sure. You won't be able to contact your insurance company until their offices open anyway, but I think you can probably get a tow truck on its way as soon as we get there. I'm sure we can get you a room if you want, where you can wait for things to open, rent a car, and get on your way. So, what do you want to do, Jess?"

Jess didn't really have any doubts what to do, but she still didn't want to give Tim any hint of a come on...yet. She hesitated, as if thinking it over, then said, "I think waiting here a couple of hours more wouldn't be a good idea for me, so I'll choose you and your car over a scary, dark, side-of-the-road wait."

"Good decision. Let's go." They got her bags and things transferred to Tim's car, closed the hood and locked her car securely. When they were underway, Jess could see Tim dimly by the illumination of the dash lights, and, as women are wont to do, evaluated his looks. She found him pleasantly appealing; he was probably about her father's age but in better shape. She'd never considered a liaison with an older man but it might be an interesting change from the nitwit, overgrown, spoiled brats she'd encountered at college. As she continued to appraise him he remained quiet; in fact, he hadn't spoken since they got into his car. Was this his way of keeping his distance? She didn't quite know where to go from here.

"The air conditioning sure feels good. It's hot down here even at three in the morning. Did I upset you when I wouldn't tell you where I was staying on the island?"

Tim didn't answer right away. Finally he said, "No, I can understand that being picked up in the middle of nowhere, alone, by a strange man at three o'clock in the morning, doesn't happen every day. As appealing as you are, I can imagine that unsolicited seduction efforts must not be an unusual occurrence for you. I'm just glad for your sake that you decided to trust me. The next guy to come along might not have been safe at all."

"You think I'm appealing?"

"Young lady, that can't possibly be a surprise to you. You must have mirrors in your room and young men flocking around you day and night. Of course you're appealing. I'm old enough to be your father, but I'm not dead yet."

"Are you married, Tim?"

"Yes."

"Do you cheat on your wife?"

Tim didn't quite know how to deal with a question that direct from a stranger, an attractive young female stranger at that. He thought a minute before he answered.

"Haven't yet, Jess."

"Does that mean you might?"

"I suppose. I'm as susceptible to temptation as anyone else, but I've not gone out of my way to stray. In all honesty if the opportunity presented itself, I just might succumb. I know my wife has on occasion, so I suppose I could plead justification, but I never was skilled at seduction, and no woman has come after me seriously yet, so the decision hasn't had to be made."

Tim was considering whether or not she was making a pass at him, but decided that was wishful thinking on his part. He decided to come back with as direct a question as she'd asked. "Have you ever slept with a married man, Jess?"

She remained quiet while she thought about what he'd said. Out here in the middle of nowhere, alone with a strange man, at the center of an adventure that was outside her experience, she was tempted to do the outrageous.

Jess had never had to seduce a man. Every one she'd ever met wanted her in bed the moment he saw her. She'd given in to more than one, but they'd mostly been disappointments, and she wondered if an older man might be different. She said simply, "I haven't yet."

"Does that mean you might?"

"Touché to you Tim,"

This is the first man I've met since I grew breasts that seems totally naïve about how to get a woman into his bed. He's embarrassed to even approach the subject. If this is just a technique of his to get women in bed it's a very effective one. Give them a challenge they can't resist by playing an innocent. The problem is whether he's and innocent or a letch. Should I take a chance and try calling his bluff? If he really doesn't know what he's doing it won't take much to shut him down, and I'm apt to lose my chance. On the other hand if he's gaming me I don't need that. So what do you do now Jess? You stall, that's what you do.

Tim didn't quite know where to go from here. On the one hand he was terrified of even considering sex with someone besides Georgia. How do you approach sex with a totally strange woman whom you've no idea how to please? On the other, he was excited that Jess might be interested in him, even if he couldn't figure out why. He finally managed to say, "It seems we're both sailing in uncharted waters. Unfortunately, me more than you."

In spite of her caution, Jess didn't appear to Tim to have any inhibitions at all when talking about even the most intimate things, as she asked him, "Do you enjoy sex with your wife?"

"I guess I'd have to say I do. After twenty-two years it tends to get a bit routine and predictable, but it's still enjoyable. Don't you think that's a dangerous subject for you to be broaching with someone you don't want to let into your personal life?"

"Tim, we've been alone with each other for nearly an hour now, and you haven't even made an untoward remark, let alone any threatening gesture toward me. Since I'm not raped and lying dead in the ditch, I don't think a little frank conversation is out of order, do you?"

"Well Jess, it isn't something I'm much accustomed to from the opposite sex, but I guess that depends on what you're after. Since I don't have any experience at all in the pursuit of recreational sex, if you're hinting at a one night stand, I don't know how to play that game. I'd just be stumbling in the dark, and I don't mind telling you I'd be terrified. On the other hand, if you're after a longer term relationship, I'm not a good candidate for that either, because I'm not willing to risk my marriage for some clandestine affair that ultimately has to end.

I was raised at the tail end of an era when sex without consequences didn't exist. Pregnancy, disease, emotional injury, religious punishment...they all made sex before marriage a dangerous, socially unaccepted activity. Yeah, a lot of people engaged in it, but polite society denied its existence, and people certainly didn't talk about it. Extramarital sex was looked at the same way. People did it, and still do it, but it wasn't accepted except under cover of deceit. You certainly didn't flaunt that you were cheating on your spouse.

Things seem to be different today. TV and movies sell incidental sex as the norm, and I have to wonder if they lead or follow our social customs. I think one of my philosophies about life is that if a relationship has to be hidden, you shouldn't be in it...shows you how old fashioned I am."

Jess didn't know how to react to what Tim had just said. She'd never met anyone both as mature and naïve at the same time. While she was trying to sort out where she wanted to take things next, something she wasn't at all accustomed to doing, Tim was thinking,

I should learn to keep my rambling mouth shut. She isn't any more interested in philosophy than any other twenty year old female, and it's sure not helping my cause any to bore her to death.

What is my cause? Can I really pursue seducing a twenty year old for a one-night stand? Is it apt to be worth the price? I don't even know what she looks like in decent lighting. Pretty enough face and hair and it looks like she has a great body, but that's all I can tell. Of course, what the hell else do I need? It's not like I get to try my hand at getting some strange without any commitment or much danger every day. If that's what she's really making available...

Jess, on the other hand, had understood everything he'd said. The longer she was around Tim, the more she thought getting to know him was something she wanted to do. He was certainly more interesting than the football jocks she spent most of her time with, but did she want to just spend time with him, or did she want to do more? She was becoming convinced that he really didn't have any experience outside of his marriage, and wondered if leading him astray, as easy as it should be to do, was something she could live with afterwards. It's one thing to spar with a single guy, but being the first to bring a married one to cheat on his wife is something else. Spring break seemed less and less important all the time.

She took the bit in her teeth. "Does not hiding a relationship mean that if you spent the night with me, you'd feel compelled to tell your wife you had? Or would you need to have told her first that you were going to? Sorry, I'm getting ahead of myself. You haven't even said you wanted to spend the night with me, have you? I guess that makes me an egotistical bitch for assuming you'd want to bed me, just because I'm here. I need to quit assuming every male on the planet wants to as well."

"Jess, I'd suggest that wasn't an unfair assumption. At the risk of turning you off, could I defer a decision on asking you to sleep with me? There's a lot more to be decided here than just whether I want to have a one night fling with someone young enough to be my daughter. I've never had the guts to try that, and it goes without saying that part of me wants to very much; however as the philosophers say, every action has consequences. I haven't even figured out what those consequences might be, let alone whether I'd be able to pay for them."

Jess was beginning to enjoy this cat and mouse game. "Like what, Tim? What's to be decided besides whether you jump the fence or not?"

Jessie, if you don't watch out you're going to have this guy all over you. Is it just because your ego doesn't want you to be turned down for the first time in your life, or is it the challenge that's turning you on? You really can't afford to fall for this guy...can you? This is supposed to be a two week fuck party, not a fall in love with your father trip.

"Frankly, Jess, I'm not at all sure I can provide an exciting romp in the hay for you anyway. I told you that my wife has slept with other men and that doesn't bode well for my ability to satisfy a partner, does it? I'm sure I don't have the endurance or the aggressive enthusiasm that you're accustomed to from your male peers at school."

"Don't overestimate my male peers, Tim. At least you have some concern for satisfying your partner, which is more than I can say for them; and endurance isn't one of their strong suits either. What else is giving you a problem?"

"Jess, I get the feeling that starting down this road may be a bit like starting cocaine. It could easily lead to an addiction that can't be stopped, and I can't help wondering if even the most exotic encounter is going to be worth the long-term problems, especially when I don't have any idea what those problems are, or if the encounter is going to be as exotic as I'm imagining. I really don't want to turn in to what some of my male acquaintances seem to be. They spend most of their time scouting out possible conquests without any attention to what those women might have besides a willingness to sleep with somebody they don't know. They don't much care what they look like, act like, or expect. Maybe that's the norm for human males, but if it is then I'm a long way from normal. I don't think I could fuck a strange female just once and then walk away and forget her, like nothing happened between us."

Jess eyed the black asphalt moving under the car at seventy miles an hour and thought she might be moving almost as fast towards coaxing a stranger into her bed. He'd handed her a challenge and she couldn't resist testing his logic. "Do you think it's possible to separate recreational sex from making love with your longtime partner, without adversely affecting that long term relationship? Do you think your wife has managed it, or is she just hanging around because of the kids and out of habit?"

Then Jess had a brilliant idea and asked Tim, "If you really believe you're such a lousy lay, wouldn't you like a second opinion?"

There you go Timmy, I'll give you a challenge and an incentive to match mine.

Tim's mind was turning over as his body responded to the thought of getting something he'd fantasized about for years.

Well old buddy, you're going to have to decide what to do. She's made up her mind to charm you with logic to overcome your great-sounding doubts and reservations, and if you stall too long you're apt to lose her interest. It's time to put up or shut up.

"Tell me, is this the sort of thing girls your age do these days? I can't imagine someone like you needing to hit on someone like me. Half the guys at the University must be just aching to get their hands on you."