Traveling with Charlie

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As an older man I find romance with a whore.
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oldbob68
oldbob68
178 Followers

This is sort of a continuation of "Passing Ships" that I wrote a few weeks ago.

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I'd just made this trip a couple of months earlier. I had attempted my third try a reconciliation with my wife and despite the promises she had made me, she made no effort to fulfill them. She was still the whining frigid bitch she had become in the last ten years. I had a good trip back home the first time with a very pleasant interlude on the second night. Too bad I didn't know her name.

My buddy George had located a place for me to rent. It was smallish but suited me just fine. What he hadn't told me before I got there was that it was a "clothing optional" place. He thought it was funny and he was right. I'm not the prize I once was but looking at sagging seventy year old boobs does not necessary entice me either. I went to my doctor for a check-up and told her that I had had unprotected sex with the help of one of the sample blue pills she had given me. She asked where I was staying now and laughed when I told her. She gave me a prescription for Cialis "Just in case the mood and opportunity arise," she said with a smirk.

After I was there for a couple of months I was sitting in a bar and George asked me for a favor. "My brother just had a stroke and can't drive anymore. He's giving me his pickup. Will you get it and drive it back for me? It's in Amarillo,Texas and you just made that trip. I'll pay all your expenses, including your airfare there and hotel, fuel and food. The truck is a F-250 with diesel and a crew cab. It's just what I need for work" George owns a construction company.

I readily agreed. I was in his debt favor-wise and one week or less out of my life at my age was nothing. He thanked me and said he'd make all the arrangements. I was sort of looking forward to the trip. I knew in my heart of hearts that I'd probably never get as lucky as I had the last time I took that route but when you're my age hope better spring eternal or you'll wither and die.

A week later George called me and told me it had all been arranged. The truck had just been serviced, detailed, and gone over carefully. The airline tickets were first class to Dallas and then a commuter jet in from there. He is truly a class act. He drove me to the airport a week later and handed me a tag, insurance card, and a credit card to cover everything else.

I arrived in Amarillo a few hours later. His brother's wife was there to greet me and take me to the truck. I told her I was sorry to hear of her husbands stroke but that George really appreciated the truck and had been talking about buying one for a few months. We pulled into the drive and there was the truck. It was a beautiful beast. Whoever did the detailing should be proud. I almost hated to take it on the road and smear it with crashed mosquitoes. She was prepared with a screw-driver for me to swap tags and I loaded up my small amount of gear and headed east. Her husband was back in the hospital, probably for the last time.

One thing that hadn't been taken care of was filling the tank. I was empty on one and a quarter full on the other. Luckily, I-40 was pretty close and I remembered there being a busy truck stop there. I waited in line and finally got a chance to fill both tanks. I knew it was a long way to Oklahoma City and that was my goal for the day. As I was fueling up I saw a young woman walking down the line of pumps. Even from a distance she had one, well make it two, distinguishing features. They had to be double D's. I thought she was panhandling and was prepared to hand her a five just for the show. I turned and opened the other filler cap and all of a sudden she was standing behind me. I tried to look her face instead of staring at her tits.

"Are you headed east?" Her voice was a bit husky. She looked to be quite young and was really somewhat plain looking. The tits were self-evident but the hoodie she wore could have concealed a nice flat belly or a paunch. Since she was turned toward me I had no view of her butt. What I did notice was that the backpack she was toting was expensive, as were her designer torn jeans. Her hiking boots probably cost three or four hundred bucks. If this young woman was a panhandler she must be a very good one. I told her I was indeed going in that direction.

"If you would like some company for I while I'd like a ride. I can be very good company." Even though she wasn't super pretty stocking cap on she definitely had a very seductive smile. I finished filling and took my receipt as I thought about the risks and possibilities.

"I have three questions for you before I answer. How old are you? Are you running away from the law? Are you carrying drugs?"

"I'm twenty-six. No to the second, and I prefer to get high on life and the people I meet."That last answer made me smile and I held the door for her and helped her take off her backpack. As she bent over to put it in the backseat I finally got a look at one very fine ass.

I opened and held the front door for her as she climbed up into the passenger seat. I got in the drivers seat and she told me that the only guys who ever held the door for her before were limo drivers. I grumbled that chivalry was dead and so was the appreciation of it. (Just a week before a woman had chastised me as sexist when I opened a door for her.)

She took off her knit cap and wonderful curly red tresses fell to her shoulders. One thing I had learned about redheads a long time ago was that sometimes, like big-game fish, they are occasionally hard to hook but if you do snag one you'd better hold on tight.

"Where are you headed and why are you hitching rides. Your gear and your clothes tell me you're not poor and homeless. That's why I asked if you were running away."

"Thirty years ago my mother was walking the beach at Daytona and spent ten days hitching across country until she could dip her toes in the Pacific. She told me it was exhilarating and certainly fun. I'm doing the trip in reverse. Two days ago I was in Newport Beach and today I'm in Texas. A girlfriend took me to Barstow and dropped me off at the western end of I-40. I found a ride on a truck that took me here. I told her she was lucky to find a ride that took her that far.

"Actually I was looking for more adventure like the ones my mother told me about. This was a husband and wife driving as a team. They only stopped to change drivers, fuel, and pee. It could have been good if they were interested in fun but all they did was listen to the bible on CD and try to save me. They had to deliver their load to a warehouse near where I met you and, thankfully, were headed back west." She ran her hand across the seat. "This is a nice truck. Have you had it for long?" I explained that it belonged to a friend of mine and that I was just delivering it to him.

"Good friends do thing for each other. Maybe we could become friends?" I caught the innuendo and felt my cock sort of gurgle. I didn't answer but changed the subject instead.

"Aren't you afraid of camping out alone?"

"Not really. I have few material things to steal and anything else an intruder or intruders want will probably leave all parties happy." The innuendo was melting away and my cock twitched again. "You asked my age. How old are you?" I told her I was sixty-nine. "Do you like it?"

I was still going to be a little coy. "I'd rather be twenty-nine and know what I know now."

She answered "That's not what I meant. I wondered if you like going sixty-nine."

"It's OK if my partner is into it occasionally. But really I'd rather take turns and please her and then have her please me, plus I once was with a young woman who came really hard and bit down. I still have scars as a reminder." That made her laugh.

"You must really know what you're doing down there. I only bite when it's wanted." My hard-on was raging and I had to adjust my shorts.

She saw me and smiled, "Its getting a bit warm in here. Do you mind if I shed this jacket?" I just shook my head. She unzipped it, pulled it off, and tossed it in the back seat. The rest of her clothes appeared to be new and fresh. Her shirt was an old spaghetti strap Tee that looked like it had been washed a hundred times. It was threadbare to the point that I could see the outline of her large areola and her big firm nipples. It was also about three sizes too small. She saw me looking and asked if I liked them.

"I think you can tell that I do."

"I think they are my fourth and fifth best assets."

"They look fantastic from what I can see. What could be better?"

She pulled her shirt up and over her tits and moved over closer to me. They were indeed beautiful; all creamy and smooth except for the firm pink peaks that crowned them. I knew exactly what I would like to do with them.

"I felt your eyes staring at my ass when I was putting my back-pack in the back. That would be next. I can make my anus open or wink on command. Next would be my pussy. My mother taught me how to pick a dollar bill up off the floor with it. But what most men and a few women think is the best part of me is my mouth."

She moved still closer and took one of my hands and placed it on her tits. I was having trouble driving.

Her hand found its way to my lap and she massaged my bulge. I was so hard it hurt to be confined but she relieved the pain a little when she undid the clasp on my shorts and let down the zipper.

She smiled up at me. "Believe me; I know cocks and yours is a beauty." She leaned over and kissed it as her hand found my balls. "Do they need some relief?" I was have trouble keeping the truck on the road. "Why don't you pull in at the next rest area and I'll ease your pain." I had just seen a sign that said the next rest area was sixty miles away. I pulled off at the next exit. It was in the middle of nowhere and I'm not even sure why it warranted an exit. I pulled onto the shoulder, stopped, pulled my shorts off, and turned to face her.

"I haven't had any cum in my mouth for almost a week. Don't hold back."She laid between my legs and I could feel those soft big tits resting on my thighs as she made love to my cock with her mouth and then throat. She took all ten inches in with such ease that I was amazed. I didn't last long and when she could tell that I was on the verge she pulled back off for a second and then took just my head in as I came. She kept me in and sucked until I was soft and dry, except for her saliva.

"Feel better?" I just nodded numbly. "Will you take me all the way to Florida? I saw your tags." Again I just nodded. "I told you I'd be very good company."

"That was probably the best blow-job I've ever had. I can't believe you took me all in so easily without even a bit of gagging."

"When I was a kid I used to gag just brushing my teeth. Then they took my tonsils out and must have somehow snipped a nerve. I can't even make myself heave. That mistake has served me well. As for being good at it, I've had a lot of practice and had an excellent teacher."

I put my shorts on and sat back upright to drive after giving her a warm thank-you kiss. As we got back on the highway I had to ask. "Who was your instructor?"

"It's sort of the story of my life. I'll tell you if you'd like but it will take awhile." She snuggled up next to me and I told her we had a long drive ahead.

"My mother was my teacher but we probably need go back further than that. Two years after she hitched across country I was born. She was, and still is a stripper. She named me Charlie after the guy she thought most likely to be my father. After she was a few months pregnant she couldn't work and found a guy to take care of her until I was born and for a year or two later. I was pretty much raised by babysitters. My earliest recollections are of her coming home with some guy or guys after work and seeing them leave in the morning. I was about five. We moved a lot. Now I know that strippers sort of wear out their audience after a few months but will do just fine at a new club in a new town. There was a progression of guys that I called "Uncle This or Uncle That." I started to catch on when my hormones kicked in."

"We finally moved to Vegas when I was a sophomore in high school but probably should have been a senior. I was the only eighteen year old in my class. Moving constantly had taken a toll on my education. Every new school told me I was either missing too many days or had missed some required class. I was also painfully shy. I know I'm not pretty. I had never made any friends, let alone boyfriends. I had been totally flat chested until just shy of that birthday." She saw the shock on my face.

"I went from a well padded A cup to a D cup in one year. That made me even more self conscious. I heard whispers that I must be wearing falsies."

I had to interrupt. "I have a couple of questions. When you took off your hoodie I had you pegged as double D's and how did you keep from getting stretch marks? I once knew a girl who grew half that fast and had small ones all over her tits."

"I was a D until a few years ago. Gravity is starting to take over. I figure in a year or so I'll have to get some help from a plastic surgeon. As for the stretch marks, my mother told me to rub them at least twice a day with cocoa butter. I do it 'til this day. Maybe you'd like to help me with that later? I read your mind when I took off that hoodie. You could grease them up really well and spill your seed on my face and tits. I'd love that." I told her, I'd put it on the agenda but I had a few other things in mind first and we had a few days.

"How many nights will we stop and when do you plan on doing that tonight?" I told her we could stop whenever she wanted. "How about if we just stop at the next rest area and I suck that beautiful cock of yours again? You gave me more than I expected but I need even more of that sweet and salty goo." Her hand was up the leg of my shorts and massaging my balls.

The next rest area was about forty miles away and I urged her to continue with her story but not to stop the gentle massage she was giving me.

"I was obviously the oldest oldest junior in the class after the summer break. My hormones were raging. I could hear my mother and Uncle 'Whoever' through the wall every night. I still had no idea what they were doing but somehow knew that I wanted to do it too. I read a few romance novels and that made it worse. I was getting some idea of what it must feel like to be taken by a man. The problem was that I was still considered the "falsie girl" at school. No boys ever asked me out and girls just shunned me. One guy who didn't ignore me was my next-door neighbor. Mr. Ames always gave me a big smile when he saw me and I could tell he was really smiling at my tits. He worked some weird shift where he was usually home when I got off school. His wife worked as a dealer in one of the casinos and left for work at about the time he came home."

"I decided that I'd be prettier for the boys if I had a tan and would lay out in the back yard in my bikini. Out of the corner of my eyes I could see Mr. Ames in his window looking out at me. After a week of this I decided to up the ante. I wanted this guy to make a play for me. I didn't care if he was old enough to be my father. He had shown interest! Each afternoon I would pull my top down a little more and pull my bottom piece down a little. I finally got to the point where my pubes were just visible and my top was virtually non-existent. I was so horny for him. To make matters worse I was constantly rubbing the cocoa butter on my tits and that made me hornier still."

"One day I just went for it all. I was buck naked on my blanket and rubbing the butter on my tits and playing with myself with the other hand. There was still no response from him even though I knew he was watching. I got pissed and walked over to his door carrying my bikini in my hand. I banged on his door and when he answered I could see his bulge. I dropped to my knees and pulled his shorts down. I had never really seen one before and the size of it took me by surprise. It was pointing straight at my face."

"I don't know why, but I wanted to taste it. I knew nothing about that but I just knew I wanted it in my mouth. He must have been seeping precum as he watched me. I just took him in and savored the musky and manly taste of his cock. Once he was there I had no idea what to do. I just held the tip of his dick in between my lips and let my tongue sample the taste. He took charge without saying a word and pushed his fingers through my hair and started to stroke in and out. He just fucked my mouth. I had absolutely no idea what to expect. Somehow, with all the different schools, I had missed a sex-ed course. With each stroke he went deeper and deeper until he was at the top of my throat."

"He finally made a sound and came in my mouth. I hadn't expected that but I loved the sensation and the taste. I got up and he reached down and rubbed my buttery tits. I left for home and neither one of us had said a word. We repeated the whole thing on the next two days. His wife had the two days following off and I deemed it best to just stay in my room. Self stimulation was just not enough however and I was still a virgin, albeit now a cock-sucking and cum loving one. When I got home from school that day I went to his door as I had before. I finally said something, 'I'm a virgin and I need you to fix that!' Again he didn't say a word but led me to the kitchen table and pushed my face down to it while he spread my legs."

"He shoved his cock in hard. It hurt like hell and I screamed. He kept hammering and the more I screamed the harder he went. He was like a dog on a bitch." I put my arm around her shoulder and drew her to me.

I told her that was a horrible first experience for her. Of course I remembered almost guiltily the no-name slut whose throat and virgin ass I had ravaged just two months before.

She squeezed my cock. "I'm just glad he didn't have anything like you. I told you I thought he looked big at the time but in reality he was actually a little sub-par. Anyway, it was probably a good thing that he took my cherry in the kitchen. I bled and bled. I left drops of it all over their kitchen floor on my way out. I sort of decided that I enjoyed sucking more than fucking. Mr. Ames and I had a dozen or so more encounters. One of the last was in my bedroom. My mother was supposed to be gone for the weekend and his wife was at work but I wanted him in my space. He came and as usual I was naked and on my knees waiting for him. He sat on the edge of the bed and started to fuck my mouth hard. I didn't hear my mother walk in the house or see her at my bedroom doorway."

"Apparently she had been there for a while. 'If you're going to go down this path you should learn to do it right. You control him. He doesn't control you; especially with that little thing!' Her tone was derisive. 'Watch me,' She ordered. She took all of him in and grabbed his balls. When he tried to dominate her she squeezed them until he stopped. She had him whimpering for relief in about ten minutes."

"My mother continued, 'Now that you have established control, enjoy yourself and get what you can from him. In the end you'll both be happy.' It's a lesson I'll never forget." I told her that her mother sounded like she knew what she was talking about. "Like I said; there was a parade of men that came home with her. She told me later that she wasn't a prostitute but she was always happy to reward the best tippers."

"A few days later Mr. Ames told me he had a few buddies coming over to play poker and his wife was out of town. He asked me if I could be there to act as hostess. I showed up at about seven and there were five guys sitting at the table playing cards. Mr. Ames gestured for me to get under the table and as I did I heard five zippers. I knew his cock well by now but the others were all new to me. One was longer than his and about the same thickness. Another was just huge, but not nearly as big as this baby." She bent over and blew a stream of her hot breath through my shorts. "One was very fat, and one was just tiny. I knew what they wanted and I desired it just as much. I made my rounds twice. They all tasted different as well. Some were saltier than others and the tiny one tasted terrible. I really had to steel myself to do him the second time."

oldbob68
oldbob68
178 Followers