Selling Rags

Author's note: the following story is purely a work of fiction and any resemblance to real people or events is purely coincidental. The author wishes to express his gratitude to rozezwild for her editing to make this a better story.

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Oh, man! I had my doubts about this new job. I had never done anything like it and didn't know if I could do it when it came down to the rubber meeting the road. I'd just have to try it and find out.

The problem was that I needed a job. I had to have some income, to save some money through the summer, or my first semester in college just wouldn't happen. And there were a bevy of jobs out there this summer to choose from. The economy was tight and so were opportunities to earn money.

So I took this job. I mean, it wasn't like I hadn't looked for something else. I had diligently scoured the want ads in the papers for something ... anything ... that looked more promising. There just wasn't anything. So I took it.

The job was the back end of a telemarketing operation. Yeah, I know, but back then, telemarketing had not earned such a bad name as it has today. I'll admit that our operation did a lot ultimately to add to the distastefulness of the industry but at the time it seemed innocent enough.

The set up had a large office full of callers sitting shoulder-to-shoulder making call after call. As soon as someone answered, the caller went into a spiel to try to get the buyer to take a series of magazine subscriptions. We had a list of 56 magazines to chose from, something for everyone, and the buyer got X number of subscriptions for Y dollars. As an added incentive, we had a big thick multi-color hardback illustrated cookbook as a "free gift" for purchasing the subscriptions.

When the callers got someone to agree to look at our stuff, they wrote up an order with the buyer's name and address. Those sheets were divided into different parts of the city and doled out to the four or five "closers." The closers went out to the buyer's house, got the buyer to make their magazine selections and provide a check for a down payment. In turn, the brand new cook book was left for the buyer. That is, if the closer could get the buyer's signature on the dotted line, which turned out to be the hard part. The problem was that our "subscription rates" were just barely lower than newsstand prices and much higher than normal subscription rates.

My first day on the job - a Monday, the manager of the operation talked to me about how to close deals. He emphasized that I had to know my stuff, to be confident, and to get in and get out. That was the way to make money, since I would be paid on the basis of the number of deals I got signed. Since that was also the first day the callers were working, I wouldn't actually go out to make any visits until the following day, when he would go with me to show me how it was done.

On Tuesday morning, we left the office about 9:45. Mr. Matthews said that you didn't want to get started too early because people were generally not ready to do business early in the morning and tended to reject all logic. Later in the day, they would be more receptive. Since my territory was in the southeast quadrant of the city, we had a 40 minute drive to get to our first stop.

Mr. Matthews took the sales slip and knocked on the door. A fiftyish woman answered the door and, when he had introduced us, invited us to come in. She sat on the sofa and he sat beside her, indicating that I should sit in the facing chair. He took the sales slip, with the list of possible magazine choices, and gave her a very polished spiel, covered the advantages of the free cook book, and got her to make her selections and sign the form. She got her checkbook and came back, writing a check for the initial amount. We were back in the car in about 35 minutes.

No one was home at either of the next two places so they went to the bottom of the list to retry later.

At the fourth place, we were greeted by another fiftyish woman, who escorted us into her living room. Again Mr. Matthews sat beside the woman and began to go into the routine. However I noticed a marked difference. The woman was wearing a pair of short cutoff jeans and a loose blouse. He sat very close to her and every chance he got, his hand would brush against her leg. Every time he would reach over to point out something on the list, his hand would brush her leg a little higher when he drew back.

When I first noticed the touching, I figured it was accidental. Then when it kept happening, I figured it was just a matter of time before she called the police or at least threw us out. But no! Her reaction wasn't like that at all! Instead her legs seemed to be spreading. Her left thigh was pressed against his right. She seemed to be moving backward on the sofa, leaving more of her legs open to his touch. Her eyes, instead of being wide open as they had been when she greeted us, were half closed as if she were in a trance. Having had very limited experience with women myself, I was amazed at what was happening.

But not nearly as amazed as I was when he blatantly dropped the palm of his hand to the center of her crotch and began rubbing. She fell back against the sofa cushion and sighed. The look on Mr. Matthews' face said that he knew he had her. She started mewling and he shifted his focus quickly to her blouse, whose buttons gave little resistance. She wasn't wearing a bra and he massaged her right tit while he lowered his mouth to her left nipple, licking and sucking the hard protuberance.

The woman seemed to be totally under his spell. I wasn't sure what had signaled him that she was ready but I watched, hoping to learn. He soon had the woman begging him for more as he manipulated her boobs. He shifted a hand back to her shorts and after a little fumbling, had them unbuttoned and unzipped. She even lifted her hips when he started working the shorts down her legs and followed them with her white rayon panties. She flipped them off her feet, the wet panties landing in my lap. I lifted them to my nose but kept my gaze on their activities.

Mr. Matthews slipped his fingers into her slit, spreading the soft petals and exposing her wet opening. He slipped his middle finger in past the second knuckle, working it in and out for several minutes. Then another finger slipped in by the first and, a few moments later, a third joined them. By then the woman seemed to have lost control of her muscles; her head was rolling from side to side and her legs kept closing and opening.

Finally he turned so he could take off his pants and shorts, kicking off his shoes and shrugging out of his coat. Then he turned back to the woman and half lifted, half pulled her over on top of him. Straddling his form, she quickly sat down and enveloped his raging member and lay on his chest. I wasn't even sure she made those moves consciously; she seemed to be in a sexual daze.

I sat there watching his cock going in and out of her pussy so very slowly as he used both hands on her buttocks to lift her up and then let her fall back down his shaft. Every time he squeezed her ass to lift her again, her globes would spread, leaving me staring at her puckered ass hole. He looked over her shoulder and saw me licking my lips and I'm sure he knew what my gaze was on.

After several minutes, he dropped a hand to his jacket on the end of the sofa. When it came out, he flicked something toward me.

"Hey, get your pants off and cover yourself with that. Then get over here and help me."

I wasn't sure what he had in mind - at that time, I'd never had a piece of ass and I'd never even thought about ... never even heard about ... a double penetration. But I did what he said. When I stepped over, he spread his knees, then spread her cheeks with both hands. "See that? That's your target. Take it slow and easy, son. I guarantee you won't be sorry."

I was kind of turned off by the sight of his hairy legs and knew that I couldn't get close to her without touching him. Ugh! But then that was not enough of a turn-off to make me stay away from that big round butt with its pretty puckered target in the center. I moved up close to her, pointing my greased pole at her unoccupied opening.

I heard him whispering to her, "Just relax. You're going to love it, babe."

I eased forward, watching the bulbous head of my dick push the opening out. Just as the head popped inside her ring of muscle, her head jerked back and I thought her mouth opened but Mr. Matthews covered it with his own and in a few moments she settled back down.

Her anus was unbelievably tight and I worked back and forth slowly, just a little bit at a time, little by little lengthening my strokes until finally my crotch mashed up against her bottom. I know I wasn't really experienced at sex but this felt so strange - I could actually feel his cock inside her pussy and it felt as if they were in the same hole rubbing against each other. I knew there was a thin layer of flesh between us but it wasn't noticeable.

I began to stroke in and out, being careful to keep stop when the rim of my member touched her sphincter. I hadn't thought about how it would work but it was amazing how the dynamics seemed to click. As I backed out of her tight ass, I pulled her body down Mr. Matthews shaft in her pussy. When I pushed back in, her whole body eased forward, pulling his cock back out of her cunt. They didn't have to do anything, because I was essentially fucking them both.

For a while, she lay very still on his chest. From time to time, she would swiftly turn her head from one side to the other and then lay back down. As time passed, the head turning became more and more frequent. I didn't think anything about it until she finally jerked her head several times in rapid succession and screamed, "Yesssss, I'm cummmmmiiinnngg!"

I could feel the woman's body shaking like a leaf in a high wind for several seconds and then it quit. She was so limp it looked like she had passed out. But Mr. Matthews gave me the OK sign and said, "Keep going, son. Don't stop now."

I resumed my probing cycles, loving to watch as my cock pulled back out of the woman's ass. Now I could also see that her pussy had apparently dripped her cum, letting it trickle down onto Mr. Matthew's thighs. It occurred to me that rubbing his hairy legs had not bothered me at all while my cock was plowing the woman's tight ass. Strange phenomenon!

Her ass seemed to be a little less tight so I picked up the pace just a touch. In and out, in and out, in and out. It was a wonderful feeling. For some reason, I began to rock my hips sideways every time I buried my cock inside her. That brought another thumb-to-finger circle OK from him so it must have been the right thing to do. A few seconds later the woman's head jerking resumed, slowly at first but rapidly gaining speed.

After several minutes, she again screamed, "I'm cummiiiiinnnnnnnngg! Do it!"

I kept pumping and rocking, watching the woman shiver though her pleasure. When she again relaxed, I grabbed her hips and began pumping faster. Mr. Matthews said, "Son, squeeze her tits and fuck the hell out of her."

I reached around her and filled my hands with her big knockers, feeling the hard nipples between my fingers. Using her hooters for leverage, I began pumping as hard as I could. It felt as if the friction between our cocks would start a fire in the woman's hot openings. It sure started a fire in my loins! A few minutes of that wild banging was all that I could stand. My balls began spewing hot cum into her bowels. Almost at the same time, I could feel the throbbing along the underside of my cock which signaled Mr. Matthews pumping his load into her pussy. Something triggered the woman again and she tossed her head back and climaxed one more time.

"Go find a bathroom and get cleaned up, son," Mr. Matthews said to me. "I'm going to hold our friend for a while until she's feeling ready to get up."

A few minutes later, I came back and dressed. Almost reluctantly, the woman rolled over and let him go to the bathroom.

"Would you hand me my panties and shorts, honey?" she asked.

I found them on the floor and actually helped her put them on, but not until I had inhaled the fragrance of her panties again while she smiled at me.

"Will you come by again to see me?" she asked.

"I certainly will if you'd like me to."

"I do. Just you, not your friend, Okay?"

"Yes, ma'am."

So we headed to the car with her check, the order slip, and a lot of satisfaction.

Our next customer was a man. The approach was similar but there was no touching. Since the man had an interest in a wide variety of sports, it wasn't hard to convince him to take the various sports magazines for his choices. We were back in the car in 40 minutes with his payment and order form.

The next customer was another woman, this time a late thirtys-early forties aged woman with a nice figure, although her face was scared from some disease. Again Mr. Matthews took charge and went through the spiel, touching the woman's leg with every movement. I could see the lust building in her facial expression.

She changed the game, though, when she leaned back and said, "I can't let you do what you want, honey. I'm married."

"That's okay, sweetie. How about letting me have a taste?"

She didn't say anything but her smile broadened. He dropped to his knees in front of her and began working her shorts and panties off. Then, with a hand under each buttock, he lifted her to his face and began to lick at her core. I knew he had found the right solution from the way she wrapped her legs around his neck. He took nearly 20 minutes to get her off twice but she was obviously loving the "getting there." When we left, we had her payment, order slip, and memories of a sloppy wet kiss for both of us.

With my instruction complete, I drove back to the office to drop off Mr. Matthews and pick up any new order slips. I took time out to eat a quick sandwich for lunch and then headed back to my territory.

My first two calls were no shows so they went back in the group for a later visit. The third one turned out to be another woman, forty-something, probably not over five feet tall but built like the proverbial brick shithouse. Not only did she have the sexiest looking body I'd ever seen, she had a good looking face too. I figured there was no way this lady would allow any advances from a kid fresh out of high school.

Nevertheless, I sat beside her on the sofa and started going through our offerings. She liked the cookbook but not enough to make a difference. She liked magazines but couldn't find any that caught her fancy. I began to ask about her interests and make suggestions that might be meaningful to her. Innocently after pointing out a possibility, I would graze her bare leg as I withdrew my hand. Intent on being helpful, I leaned my shoulder against her shoulder, my right hand "caught" against her hip between us.

At first the woman didn't seem to notice. Then just as I tried to point out a possible last choice, she drew back and asked, "What are you trying to do?"

"I beg your pardon?"

"What are you trying to do? Are you trying to feel me up?"

"No, ma'am. I was just trying to help."

"Oh, come on, be honest. You've been trying to touch me every chance you get, haven't you?"

I looked in her eyes and thought about lying but couldn't. "Uh ... yes, ma'am, I guess so."

"You guess so? You know so, don't you?"

My eyes cast down, I replied, "Yes, ma'am, I do."

"Why?'

"I'm sorry?"

"Why are you trying to touch me?"

I looked into her beautiful green eyes. "You're kidding me!"

"No, I'm not. Why are you trying to touch me?"

"Ma'am, you are so ... so beautiful I just couldn't ... couldn't help myself."

"You touched me because I'm beautiful?"

"Yes, ma'am."

"Didn't you know you'd make me horny doing that?"

"Huh?"

"Oh, come on! You've made me so horny. What are you going to do about it?"

"Uh ... eat you?"

"Then get to it."

I shucked my jacket as I dropped to my knees in front of her. She was already pushing her spandex shorts and panties down and I helped ensure that they came all the way off. Even with my limited experience, I felt confident after watching Mr. Matthews that morning. I began by licking the woman's tanned inner thighs and delighted in her sighs as my mouth settled over her pussy. My tongue worked up and down her soft crease before diving into her open vagina, then flicking out at her swollen clitoris. A few minutes of repetitive activity brought the woman to wrap her legs around my head and pull me hard into her core while she climaxed, huffing and puffing loudly.

I started my ministrations again but she pulled on my ears and said, "Honey, its time to fuck. Come here."

I stood up and she helped me get out of my clothes. Then she turned and lay along the sofa with one foot on the floor and the other on the back of the sofa. I climbed into her saddle and sank my throbbing probe into her wet snatch. She had opened her blouse and discarded her bra so when she pulled my head down to her tits, I curled my body around to suck on her twins. It was physically a little uncomfortable but well worth it.

Her pussy was as tight as any I'd ever been in; she told me her husband travelled a lot and she didn't get fucked very often. We both appreciated the way we fit together but it still took a lot of work and self-control to get her to climax twice before I filled her love tunnel with my load of hot sticky cum. We spent another 15 minutes kissing and hugging before she let me dress.

On the way out with her order in my briefcase, I asked if I could see her again. She said she wouldn't invite me back, because that would seem like she was betraying her husband. However, she said, she probably wouldn't turn me away if I were to just show up sometime. As soon as I got to my car, I made a note of her address for my personal records.

After that, I had two no shows sandwiched around three declinations that I couldn't turn around. I would have gotten discouraged except for thinking about the extra rewards I'd already received. Then I rang the next doorbell.

The woman came to the door wearing a lightweight robe that came down to mid thigh and was tied in front with a belt, the only fastening I saw. She was taller than my six feet by probably three inches and I guessed she was three times my age. However she had a very devilish smile on her face when she invited me to sit on her sofa.

The woman walked more like a man than a female and when she sat on the sofa, her legs spread like a man's, pushing roughly against mine. But I had never seen a man with the big heavy globes this lady had on her chest. So ... I went into my sales pitch and was soon gesturing at possible choices that might catch her fancy. She held the sales slip so close that when I pointed to a magazine name, I couldn't help but brush against her humongous tits. Then I'd rest my hand on her bare thigh only to start the process again a few seconds later.

Each time I brought my hand back, it stopped fractionally higher toward her pussy until I began to feel the heat coming from her core. By the time she placed an X on the last choice, my hand was resting on the curly hair over her twat, my middle finger wandering up and down the steamy slit. She leaned back, closed her eyes and sighed as I pulled the sash of her robe to reveal only naked woman beneath ... as I had expected.

I got up and doffed my pant and underwear. By the time I dropped to my knees between her legs, she had scooted down so that her ass was on the edge of the cushion. I guided my throbbing purple head into her dripping wet hole and watched her face show pure ecstasy. I think if I had left right then, she wouldn't have complained.