As I explained in a previous story, my father had health issues that prevented him from working. Not working led to him struggling financially. Although money was tight, he was able to scrape enough together to buy an old car for $500. He bought it and gave the car to me so I could use it to go back and forth to school and to my part-time job.
However, like all cheap old cars, it was a clunker that was constantly breaking down and needing work. If my father had known what that car would wind up costing his daughter, he would never have bought it.
At one point, I was dating a guy named Alan. Now, Alan was a cute guy, but he had a problem. He was unreliable and inconsiderate. To make matters worse, he lived in the next town over, an hour’s drive each way. The only reason I continued to date him was because I liked his friends. In particular, one of his friends named Mike. Mike was very personable, and he gave me a tingle every time we talked.
I had tried to break up with Alan before this event happened, but he had begged for another chance, and I foolishly gave it to him. Alan treated me better for about a week, but now, after a few weeks, he was back to being neglectful. It was time for me to end our relationship, and I wanted to do it in person. I do have class after all!
It was a Friday night, and I knew Alan’s roommates were heading out for the night, so I called Alan and asked him about maybe getting together later in the evening, and he agreed. Thinking about what I was going to do, it seemed such a waste of a Friday night just to drive all the way to Alan’s place to break up with him. Especially since it was an hour-long drive each way. Mulling it over, I came up with a brilliant idea.
Since I knew what bar Alan’s friends, including Mike, would be hanging out, I figured that after I broke up with Alan, I could just happen to stop by the bar where his friends would be. I had my eye set on Mike, and it would be a perfect way to let him know I broke up with Alan. I wanted to look like a million bucks to catch Mike’s eye plus I wanted Alan to see what he was losing.
I went all out. I decided to wear a sexy black semi-sheer blouse, with no bra. If you looked close enough, in the right light, you could see my breasts through the thin material. I added a short black denim skirt, and a pair of black high-heeled ankle boots. I went with a short leather jacket that partly covered up the thin blouse. The jacket was perfect for a quick flash or tease. I do have to admit, I looked hot.
It was around eight pm by the time I got all dolled up and into my car to start the hour-long drive over to Alan’s place. I knew about a shortcut that would shorten the time it would take me to get there, but it meant taking dark country back roads instead of the main highway.
About halfway there, sure enough, the car motor started making strange noises. I was in the middle of nowhere, so I kept driving. The engine kept making more and more strange, loud noises until the engine just quit.
I tried to restart the thing, but it wouldn’t even pop—nothing, just turned and turned. I was at a loss about what to do; it was dark, deserted, and it was getting cold. My first call went to Alan. No answer! I thought, How could that be? He’s supposed to be waiting for me to get there. I waited a couple of minutes, thinking that maybe he was busy, and tried again, still with no luck. I thought, Damn him! Where the hell is he, anyway? He knew I was coming over; he should have been at home. It was just like him to have forgotten and gone out with his roommates.
I had my AAA card in the glove box. So I dug it out and called them. I told the woman on the phone that I had broken down in the middle of nowhere and that I needed to have someone come out as soon as possible. She sounded bored, but after taking all of my information, she promised that I’d be a priority and hung up.
Then I waited… and waited… and waited some more. The whole time, I kept trying to call Alan. The more I called, the angrier I got. I even tried calling a couple of friends, but it was Friday night and they were all out.
At this point, I was scared. A young woman in a broken-down car out on a country road in total darkness was not a good situation to be in. Hell, isn’t that how every horror movie starts out?
I should have listened to my father and stayed on the main roads, even though it took a bit longer. Finally, an hour and a half later, the tow truck arrived.
I stayed in the car, and when the driver came up, I rolled down the window and explained as best I could what had happened. He told me to pop the hood and try to start the car. He got some tools and a flashlight from his truck, and a couple of minutes later he announced that, unfortunately, he had no idea what was wrong with it. He asked where I’d like to be towed.
I tried calling Alan again, but still no luck. I finally got out of the car when the tow truck driver backed his truck up to the front of the car, and I asked, “What’s the chance of having the repair done tonight?”
The driver looked me over and told me most places were closed. It was about ten o’clock now. My phone battery was just about dead, and I just wanted to go home and cry.
He saw that I was shivering and asked me if I wanted to get in the truck to warm up while he hooked up my car. I did. It was a chilly night, and my nipples were hard from the cold and a little sore from being hard for so long.
As I walked up to the truck, I looked down at the front of my blouse, and sure enough, my nipples were prominently poking up through the thin material as my jacket was not done up. I was sure that’s what the driver noticed when I first started talking to him.
Once he got the car hooked up, I saw him making a call. He got in the truck and said there was one place that might be able to help me, so we headed off for the garage. The driver seemed friendly enough but kind of shy, or maybe just quiet. It was a pretty quiet ride to the garage. It was about a twenty-minute drive further into the darkness and in the opposite direction of home.
During the drive, he kept glancing over at my bare legs. I had visions of him stopping the truck on some dark dirt road and raping me. After all, I was dressed pretty provocatively, and I was in a vulnerable situation. Lucky for me, he didn’t.
It was kind of scary when we finally got to the garage. It looked like a tumbled-down kind of place. There were a bunch of cars in the parking lot, and half of them looked like they had been cannibalized. It was creepy, and I couldn’t help but think it was exactly like something you would see in a horror movie.
The driver pointed out that it looked like there was someone in the garage and told me to go in to talk to the owner while he got the car unhitched. As I started a slow walk to the office door of the garage, the driver quickly unhooked my car and drove off, leaving me stranded there.
I tried the door to the office; it was unlocked. I pushed the door open and stepped in.
“Hello, is anyone here?”
A man with white hair came walking out of the area of the garage where they worked on cars. He was wiping his hands with a red cloth. He obviously had never visited a gym in his life and was older than dirt. He had a shirt with the name Bill stitched on it.
“Can I help you?” he asked.
Oh good, I thought, this old guy probably hasn’t had sex in years. Maybe I can flirt and exploit him into fixing my car without charging me.
I was only twenty, but I had quickly learned the power women have, especially over men. I had often gotten a lot of things for free just by smiling and batting my eyes. Sometimes it required showing a little skin—accidentally, of course—but I usually got what I wanted. But that was with young, horny boys. Would flirting work with this older man? I was confident that I could pull it off.
I explained how my car had just died as I flashed a sexy half-smile with my head down, looking up at him through my eyelashes. I had the sweet, innocent, but sexy look down pat. I went to work on this old guy, no holds barred. Bill looked me over, eyeing me up and down. He told me the garage had been closed for several hours, and he was only there because he was working on his own car. I begged him to just take a look at it.
“Please, sir, I’m stranded and over an hour’s drive from home.”
“Let’s take a look at it, okay?” popping the hood.
Mr. Bill, as I began calling him, looked at the engine. I watched him push on greasy things and pull wires, then rub all of that grease on his chin, making “hmmm” sounds.
“Is it bad?” I asked, leaning on the fender across from him and making sure that he had a good view of the minimal cleavage that I did have.
“Oh yes,” he replied. “This car could have caught fire. You’re lucky it didn’t.”
Shock and fear gripped me. This sounded expensive. I leaned forward, giving him a better view of my charms. He now had a clear view down my blouse and could see most of my breasts. I couldn’t afford to take any chances if my car could catch fire.
I stood up straight, making a pouting expression but also making sure my jacket was fully parted. Of course, I pretended I didn’t realize my cold, hard nipples were pushing out my thin blouse, making my breasts almost completely visible.
He stared at my breasts for a long while before rubbing his chin and saying, “I can fix it, but it will take a while. I’ll have to drop everything that I’m working on now to work on it for you. I know that you are stranded and just want to get home.”
I was pleased and surprised that just showing a little of my cleavage worked so well on him. I leaned a little closer to him, making sure that his eyes never left my breasts. I now had to get him to not charge me for the repairs.
“I hope that it won’t be too expensive,” I said in a shy, timid voice.
“I’ll do it as cheaply as I can,” he said. “Is money a problem? This would normally be a $1200 job and take the better part of a day, but I might be able to fix it enough for you to get back on the road.”
My face dropped at the cost. I began to cry. As I sobbed, I told him about my ill father not being able to work and how I was struggling to pay for tuition with a part-time job. How I only had $40 in my bank account.
Mr. Bill wasn’t sure what to do. He just looked at me and then said, “Let’s crawl under her and have a look. It could be a little bit cheaper if the damage isn’t too bad,” he said.
I pulled myself together, as I knew that I had to keep him interested in me if I had any chance at all of getting this repair work done and the car back on the road. I had never gotten anything that cost this much for free before, but I was willing to do whatever it took. I had no money and, thus, no choice.
Perfect, I thought. My short skirt and thong could be used to great advantage with him lying on the floor. I needed him to think with his cock instead of his brain.
He got onto his creeper and wheeled himself under the car, then stuck his head out to address me. “At least the main line isn’t ruptured,” he said, disappearing back under the car.
I positioned myself over the spot where his head had appeared and spread my legs slightly. In a short time, I heard the creeper moving again, then nothing. I smiled to myself. I’m glad I’m wearing a pink thong. I waited a while, allowing him to enjoy the view before asking, “How bad is it?”
He slid out from under the car, forcing me to move out of the way. “I think that I can get you back on the road for $600, maybe a little less if I have one of the parts in the shop.”
My face went white. “Isn’t there some way that I can get on the road without costing so much?” I pleaded.
Mr. Bill stood up and moved towards me while he was wiping his hands. I used this pause to re-apply my glossy lipstick in a very sexual manner. His eyes focused on my moist and glossy lips as I puckered up. He looked me in the eyes and just nodded.
“Oh, I’m sure you can offer me something from the way you are dressed and behaving.” As he looked me over with an evil grin.
My mind was racing. Mr. Bill had just called me out. He knew what I was trying to do. I was in a bind with no other options. I couldn’t ask my father for money because he was off work and my boyfriend was useless.
I stood there in front of him in silence, unsure what to say or how to proceed. I bit my bottom lip sexily, as I always do when I’m in trouble. That’s when he reached out and gently opened up my jacket to have a look. I didn’t resist as he ran his hand over my breasts, feeling my rock-hard nipples through my thin blouse.
“Unbutton your blouse,” he ordered.
I took a deep breath and slowly unbuttoned a couple of buttons on my blouse. His eyes watched as my perky breasts peeked out of my parted blouse.
Without either one of us saying a word, he reached up and cupped one of my breasts. I gasped as he squeezed and pinched my nipple. I looked him in the eyes with a pitiful look that said I would do anything. “Please, Sir,” I begged.
“I don’t know; maybe I could knock off another hundred. It’s not often that a pretty young thing lets me fondle her breasts.”
“You can fondle them all you want. I really need this done, and I don’t have very much money.” I had accepted the fact that this was going to cost me a lot! Mr. Bill wasn’t like the horny boys I could easily tease and take advantage of.
“$400 is about as low as I can go, and it’s costing me money to do that,” he said.
He knew he had the upper hand, and he was driving a hard bargain.
“I don’t have that kind of money.” I pleaded as I looked into his eyes.
He moved his hand off my breast and reached back and placed his hand on my ass. He gave it a good squeeze before he slid his hand under my skirt and began groping my bare ass.
“This is going to cost me a lot of money. I’m not charging any labor, and I’ll eat another hundred bucks off the cost of the parts, but you’re going to have to get naked and play with me.”
Play with him; oh shit, this was going to cost me dearly.
“Umm, what exactly do you mean by ‘play with me’?” I cautiously and reluctantly asked. I was hoping that he didn’t want sex.
“Well, that’s up to you, young lady. For a decent blow job, I’ll knock it down to $300, but that had better be one hell of a blow job,” he said.
“I don’t have $300.” I was close to tears again. I felt so humiliated. I couldn’t believe I was having this conversation with an old, gray-haired man. I felt like a hooker negotiating a trick.
His right hand was still holding on to my left breast as I looked into his eyes. His other hand was softly exploring under my skirt. I took a deep breath and cut to the chase, as I knew where this was leading. The surreal words, “How about if I let you fuck me?” came out of my mouth as I looked up at him. I couldn’t believe I just said that.
“I’m losing a lot of money here; it can’t be just a simple fuck,” he said.
Oh, my gawd, what more can he possibly want? “What do you want?” I perked up a little at his admission that he might do the repairs.
“How much money do you have?” he asked.
“I have twenty bucks in my purse, but I’ll do whatever you want,” I said.
“You have to let me fuck you for as long as I want and in whatever way I want. You will have to do whatever I say until I say that we’re done.”
I thought to myself, How bad could this be? He’s as old as my father, so he can’t be that virile. I was thinking that a quick pull and tug and it will be over—if his pecker is even still working, that is.
“Okay, but I don’t have all night, and no anal or pain…Oh, and you have to use a condom,” I added. This was more than I had thought that I would have to do, but what choice did I have?
“No condom! And that’s NOT negotiable.” He said it in a stern voice as he stepped back. “Besides, you look like the type of girl who’s on birth control.” He was getting cocky now.
I knew he had me over a barrel. “Fine” was all I could say.
“And the $20,” he said.
“Really?” I looked at him.
I opened my purse and gave him $20. That was the easy part.
“Now we’ll go into the back room and you can strip, then I want you to undress me and rub those lovely tits of yours all over my body,” he directed. He walked over and locked the office door.
I followed him into the back room and reluctantly started removing my clothes. He watched intently as I slowly stripped naked for him. My jacket and blouse came off first. Then I unbuttoned my skirt and let it drop around my ankles as I stepped out of it. I stood there in only my ankle-high boots and my pink thong. I felt ashamed as I looked down, hoping to hide behind my hair.
I glanced up, and Mr. Bill nodded as he looked at my thong. I reached down and pulled it off, too. When I was completely naked, I approached him and started to unbutton his shirt slowly, one button at a time. I was trying not to look at him, as this was a new low for me.
“Kiss me,” he demanded. “Show some interest, or I won’t fix your car, little girl.”
I looked up at him, closed my eyes, and pressed my lips to his. I continued to unbutton his shirt as he slipped his dirty old tongue into my mouth. His mouth smelled of cigarettes, and I was doing my best not to get revolted.
He pulled me closer so that my breasts pressed into his bare chest. His breathing picked up, and I could feel his bulge pressing into me. I stepped back from him to remove his pants.
I kept reminding myself that he was doing me a favor, and this was the only payment that I could give him. He was older but didn’t really look that bad. It could be worse, I kept telling myself. I lowered his pants, and his gray, hairy cock sprang free. It wasn’t too large, about average in length, but it was thick, something I normally liked.
Well, let’s get this over with, I thought. I dropped to my knees and closed my mouth and tiny hand around his thick cock. I began stroking him with my glossy lips. I then used my tongue all over him before taking him deeply again. I closed my eyes and imagined I was sucking Alan’s roommate, Mike. Fantasizing about Mike was helping me get through this.
I was impressed by his restraint. Part of me wanted him to explode quickly so that I could be done with my payment, but another part of me, the fantasy part, wanted him to last. The entire situation was surreal, like an out-of-body experience. Why does shit like this always happen to me?
His cock was still in my mouth when he pushed me away. He grabbed an old, dirty towel and spread it on the floor for me. He directed me to lie on the floor. I lay back on the one small, clear spot in the cluttered little room. I could feel the dirt and grit attached to my back, but I didn’t care. The real and the fantasy had combined, and I was in the middle of it.
He removed the rest of his clothes and told me to spread my legs. He ran his rough, clammy hands up my leg, and a finger found my vagina as he sat on the floor overtop of me. He grabbed one of my legs and flung it over his shoulder as he crouched down and focused on the task at hand.
He rubbed his fingers over my now swollen clitoris and began exploring.
“Oh, you’re so wet; you must be enjoying this.” He growled.
I just continued to lay there with my eyes closed, imagining I was with Mike.
His fingers had isolated my tiny clit, and they began stimulating it with a rapid action. I couldn’t help but let out a moan as jolts of passion shot through me. His other hand reached around my leg and began playing with my nipples.
A finger easily slid inside of me and began pushing deep. He masterfully began fucking me with his stubby finger while his thumb continued to rub my clitoral area. I couldn’t hold back my arousal. I began breathing heavily. Mike, or, should I say, Mr. Bill, knew what he was doing. I couldn’t help but think how good he was with his hands. He was fixing more than my car now.
“Oh fuck, that feels sooo good,” I purred as he began curling his finger into my G spot. I was losing control now. He had me where he wanted me, and as much as I didn’t want to enjoy the experience, he had me purring and arching my back.
“Ohhh, ohh…” I began to whimper as sexual bolts of arousal shot through me. I couldn’t hold back any longer as a gush of pleasure crested and flowed throughout every cell of me. “Ohhh, my god!” I screamed as I climaxed for Mr. Bill.
I reached down and grabbed his hand as I tried to stop him from stimulating me further. I was over the top and absolutely sensitive. He continued to finger me and stimulate my clitoral area as I began thrashing and bucking. He was showing me no mercy.
“Stop, STOP, STOP…” I screamed at him, begging for mercy.
“Oh, you’re a firecracker, aren’t you?” Mr. Bill had a grin on his face as he pulled his wet hand away. “Here, lick me clean,” he ordered as he raised his soaked hand to my lips. I obeyed him and licked my juices off his fingers. His fingers had a strange taste of petroleum. “Did you like that?” He questioned.
“Hmm, uhh,” I sheepishly replied.
“Good, are you ready for the main course now?” He asked as he repositioned me on my back with my legs up. He moved between my legs and positioned himself to mount me.
I opened my eyes and glanced down in between my legs to have a look at what was about to violate me. His hairy cock was hard, gray-haired, and erect. He placed the tip at my entrance and slowly started penetrating me, pushing his head into my love tunnel, filling me in a way that I hadn’t been filled in a long time. His idea of foreplay was somewhat lacking, but my fantasy compensated. I closed my eyes again and imagined Mike entering me.
He raised my legs and plunged forward, filling me as much as he was able. It hurt because he wasn’t gentle at all. He thrust his cock hard and deep into me as I lay there, fantasizing that it was Mike fucking me. He huffed and puffed as he grabbed my ass and leveraged himself into me.
He was making all kinds of grunting and huffing sounds. I have to admit, he was also giving me a good fuck. The sex was good, but the concrete floor was uncomfortable as hell. Just when I thought he was about to cum, he stopped, turned me over, and took me doggie style.
Doggie style is my favorite position, plus this evening it had the added bonus of me not seeing who was behind me. His cock actually felt good as he forcefully thrust it into me. I could feel the abrasive concrete floor scraping my knees and hands with every deep thrust. I moaned and squealed with pleasure as I was on the verge of cumming for the second time. I was now right into it as I pushed my ass back to meet his thrusts. I came, letting out a loud moan, hoping he would do the same, but he was still going strong. I never imagined a man his age could last this long.
He abruptly stopped and told me to get up, as he wanted to take me against the wall. He positioned me, lifting one of my legs and wrapping it around his waist. He then began pounding into me until he let out a loud groan.
“Please don’t cum inside of me,” I pleaded.
But he just ignored me and let out a deep, animalistic groan. I felt streams of warm semen ejaculate deep inside of me. He continued to hold me pressed up against the wall for a couple of minutes. I could feel his once-erect cock now begin to whither until it slid out of me. I also felt a gush of semen pour out of me and down my thighs. He passed me a red cloth to clean up.
Finally, it took some effort, but Mr. Bill finally ejaculated. I thought he was done, and now he could fix my car.
I reached to gather my clothes, and he stopped me. “The deal was that it’s not over until I say it’s over.”
“Huh? You’re not done?” I had a surprised look on my face.
“Not even close, honey.” He grinned as he grabbed me and pulled me close. He grabbed my hand and led me out into the well-lit office area. I tried to resist, as it was one of those old-style gas stations with big windows all around the office. I could see car headlights as they passed by the station.
“I’ve always fantasized about having sex on my office chair.” He pulled me by my arm across the large office windows to behind his desk. He sat down on the chair with his stiff cock at full attention. “Come here and sit on me.” Spinning me around and pulling my hips onto his lap, I felt him adjust his cock as it slid into me. There I was, naked in only my ankle-high boots, riding his cock in a fully lit office visible to the world.
I bounced on his cock as he grabbed and mauled my tits. Despite my humiliation at the situation, he was having fun. As he fucked me, he was moving the wheeled chair with his feet. He spun the chair around in a circle as it moved all across the office. I heard a car beeping its horn, but I was afraid to look. Mr. Bill was having a great time.
But it didn’t end there. Mr. Bill wasn’t finished with me. After another short break, he was up and at it again. That night we ended up having sex everywhere in the little shop: across the hood of my car, on his creeper, on his office desk, up against the office window, and even inside the back seat of my car.
Apparently, Mr. Bill had a lot of work-related fantasies. I think I fulfilled all of Mr. Bill’s fantasies that night. Every time he came, I thought he was done, but he kept surprising me. For an old guy, he had stamina. I suppose I was right to assume he hadn’t had sex in ages; he sure made up for it that night.
I lost count of how many orgasms I had. But I do know I was more satisfied than I had been in a while by the time he was done with me. Mr. Bill easily outperformed my boyfriend, Alan.
It wasn’t until 5 a.m. that he finally put his pants on and began to work on my car. He replaced a broken fan belt and told me 15 minutes later that I was good to go. I would have no further trouble.
I was shocked. He just smiled, winked at me, and said, “Come back anytime, sweetie.”
I drove home as the sun was rising. I knew I was scammed. But I suppose it was my fault for trying to tease Mr. Bill into doing the work for free. It all backfired on me. Mr. Bill wasn’t like all the boys I teased and got my way with. He turned the tables on me.
I called and broke up with Alan the next day.
