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"He makes the older ladies pay to play."

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My name is Chas, short for Charles, but no one calls me by anything but Chas. I went with that version of my name when I was in high school. I figured it gave me something unique, maybe distinctive. It also comes in handy in my line of work. You see, I'm a male escort, a gigolo if you will. The ladies seem to love calling me Chas and, since they are paying to play, whatever they love works for me.

I'm 26 years old, 6'2" and 185 lbs. of lean, toned body. I was blessed with a large cock, just shy of 10" when hard and thick like a big fat hunk of sausage. You'd think that having a big dick makes me popular with my clients, and it does, to some extent, but having a large piece of man-meat is wasted if you don't know how to use it. Believe me, I know how to use it, along with other things. In this business it's how you treat the ladies that determines whether you're successful or not. I've been fortunate to have my ladies begging for more, and it's all because I know what makes them happy.

I specialize in mature women. I think it goes back to when I was younger and the hot 48-year-old neighbor, Carol, took a liking to me and seduced me. Every boy in the neighborhood fantasized about her, but I was the only one who ever fucked her. One afternoon I mowed her lawn for her and, when she invited me inside to pay me, she allowed her robe to fall open, exposing her still firm breasts and hairy pussy. I sprouted wood as soon as I saw her naked body and, once she got her hands on my throbbing cock, she was hooked. Being so young, I was able to fuck her five times that afternoon and by the time I left, she was gasping for breath.

Carol had me back to her house many times that summer. She couldn't get enough of my hard cock, but she also gave me some valuable lessons in how to please a mature woman. She showed me how to not only eat older pussy, but also how to appreciate the mature body, how to please her in ways other than ramming my big prick inside her. By the time the summer was over, I knew what I wanted to do in life. Carol had opened my eyes to a whole new world and I wanted to take advantage of what I had learned.

College was a bit of a bore for me. I just basically drifted through my classes and got a degree in Political Science, but the biggest thing to happen to me in college was during my Junior year when I met Vanessa. We met at a campus bar and wound up spending the weekend at her apartment. During that weekend I told her about my interest in older women and she offered to set me up with some of her mother's friends. She told me that if I was interested, some of these women would be willing to pay me to have sex with them. That piqued my interest, because what could be better than fucking older women and being paid to do it? She told me that she wanted a cut of my fee in return for finding me "dates". We agreed on a 15% cut for her and she said that she would have some possible dates for me as early as next weekend. I only had one restriction, and that was that the women had to be attractive. No big old cows for me, if you please.

It didn't take long. Vanessa called me on Wednesday and told me that two of her mom's friends were interested, if the price was right. I didn't have a clue what the going rate was for sex, never having paid for it before. I asked Vanessa what she thought I should charge. She thought $500 was reasonable. That gave her $75, and I would be expected to take the client out for either drinks or dinner. After expenses, I was looking to net around $300 or more each night. Not bad for banging an older lady, I thought. I told her to set it up for Friday and Saturday. Vanessa would pick up the fee in advance, so there wouldn't be any money changing hands between me and the client.

The weekend was a total success. I had drinks and sex with Miriam on Friday night and dinner and sex with Rhonda on Saturday night. Both women were very attractive and both insisted on picking up the checks.

The sex was outstanding. Both women really turned me on and I gave them everything that Carol had taught me. I left them both begging for more.

That was the beginning. Over these last six years I have established myself as one of the top freelance escorts in the area. My fees went up accordingly and I now command $1500 for an evening of sex with those mature women who wanted a young man in bed and could afford it. Vanessa did an outstanding job as my business agent and I was in such demand that my weekends were booked solid. Hell, I even did some work during the week. A horny older woman doesn't care what night she gets laid, so why should I? I also upped her retainer to 20%. I was doing well, so there was no reason why I shouldn't share in my success. My expenses were minimal, since most of these women, especially the repeat customers, were only too happy to pay for drinks and/or dinner.

On Mondays Vanessa and I meet for lunch, where she goes over the previous week's appointments, gives me my money and lets me know what is coming up for the week. We've never had sexual relations since that weekend we met. She's still a major league hottie, but we've never mixed business with pleasure.

This Monday, Vanessa had an interesting proposition for me. She was contacted by two women who live together who wanted to know if they could schedule a threesome.

They were bisexual, both 58, retired teachers and living together for 30 years. They had never done a threesome with another man, but when they heard about me they realized that it was time to try it out.

I didn't need to hear any more about them. I was eager to get it on with two mature women at once, but I didn't know what to charge them. It seemed unfair to charge them both $1500, knowing that I couldn't give each of them my undivided attention. I suggested a two-for-one discount to Vanessa. She laughed.

"What's next, Chas, a coupon? Maybe an AARP discount? What's gotten into you?"

"Vanessa," I said. "We've never done this before and I just feel like giving them a break. Besides, word might get out and we could make a killing on this."

"What do you have in mind?"

"I was thinking $2000 for the two of them." Vanessa looked skeptical, but I used a little logic on her. "Think about it, Vanessa. Look at it like a $500 bonus for the night. It isn't fair to charge them double, so I think $2000 is fine. You're still looking at a $400 fee. If we booked a single you'd only be getting $300. Everybody makes out if we do it my way."

Vanessa could only smile at my logic. "Okay, Chas, I'll tell them they are catching a break. They want to do this on Saturday night. Is that okay with you?"

"That will be perfect. If they are good, I'll have all day Sunday to recover. Don't book anything for Sunday, though."

Friday night I had a repeat customer, Ingrid. She was divorced and didn't want to dive back into the dating pool, so she decided to pay for her sexual needs. Ingrid was, how shall I say, a little tiny in the vagina. When she saw my big cock she really had second thoughts about going through with it, but I took my time with her and before we were done she was begging me to ram it home hard. She's been a regular ever since, seeing me once every 6-8 weeks.

Vanessa had given me the information on the two women for Saturday night. Their names were Patricia and Ramona. I was to meet them at a bar that I wasn't familiar with, so I figured to get there a little before 8 o'clock, which was our appointment time.

As I sat at the bar, I wondered what pair would walk through the door. I was sure they would be attractive, because Vanessa knew what I liked and what could be a deal breaker. I had barely ordered my drink when they walked up to me at the bar.

Patricia was a larger woman, not fat, but just big all over, like an Amazon. She had curly blonde hair, big tits and she had a devilishly seductive grin on her face. She looked to be a lot of fun. Her partner, Ramona, was the polar opposite of Patricia. Ramona was beyond thin, with a tight but attractive face and a pixie cut hairdo. She wore pants and a tight t-shirt under a black suit jacket. She was mysterious enough to make me wonder what her body would look like on all fours, with my big cock shoved up her skinny ass. I had every intention of finding out.

As we had drinks, Patricia was outgoing, laughing and outrageous. Ramona hardly said a word, but when I suggested that we adjourn to someplace a little more private, her eyes lit up and I detected a slight smile. Patricia told me to follow them to their place, and to try and keep up, because she liked to drive fast. Of course.

After nearly falling too far behind Patricia I managed to follow her to their home. It was in the hills overlooking the city, remote enough to guarantee privacy, but not too far off the main roads. I followed the ladies inside and we stood inside the foyer looking awkwardly at each other.

"So what do we do now?" said Patricia.

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"Is there some kind of protocol we have to follow?"

I shook my head. "No, we do whatever you want to do. We have all night, so we can go as slow as you want, although if your driving is any indication you don't strike me as the 'go slow' type."

Ramona smiled at that. "All night? I think I could get into that." She licked her lips as she said it, which made my prick start twitching.

Patricia took my hand and led me upstairs into their huge master bedroom. They had a custom-made bed that was much larger than a king. No problem fitting the three of us in that thing.

Patricia began to take her clothes off, revealing large, pendulous breasts. They hung down nearly to her navel, but there wasn't any fat on her. She was just a big woman. There was a small patch of hair just above her pussy that had to have been bleached. It was almost white, a strong contrast to the dirty blonde curls which framed her face. "Do you like what you see, Chas? I've shown you mine, so how about letting me see what you've got?"

I stood before her and removed my sport coat and shirt. She gasped when she saw my chiseled pecs and dark, tanned torso.

Ramona stood off to the rear of the room. She took off her jacket and pants, leaving herself with just that tight t-shirt and a flimsy thong. Jesus, she was skinny, but I could barely keep my eyes off her.

I removed my pants next, leaving me in only my boxers. I always wore boxer shorts for two reasons. First, they were comfortable and second, it was hard to guess I had such a huge cock. Briefs gave too much away, so I made a point of never wearing them while on a "date".

I slowly pulled the top band of the boxers down, just enough so that they could see that I was smooth-shaven, and then pulled them down quickly, exposing my semi-rigid cock in all its glory.

"NO FUCKING WAY!!" shouted Ramona. "That's a pussy killer!"

Patricia didn't say a word, opting instead for falling to her knees in front of me and taking it into her hands. Her mouth was all over my cock, taking as much of it inside her big lips as she could. In no time, the head and most of the shaft were shiny from Patricia's spit as she lavished all of her oral attention on it. I was hard in seconds and let her have her way with it.

Meanwhile, Ramona stripped off her t-shirt and thong. Her nipples seemed to poke out forever from her tiny tits, and her pussy was framed by a full bush, thick and black. It was so thick you couldn't see her slit, but I had a feeling that I would find it.

Patricia continued sucking and slurping on my cock, moving to a squatting position before me. Ramona saw this and lay down beneath Patricia, her head directly under her shiny wet pussy. Ramona sat on her face, gyrating as Ramona began to eat her. Her moans intensified the sensations she was giving me as my cock slid in and out of her mouth.

"Do you want me inside you?" I whispered to Patricia as she bobbed her head up and down. "I really need to bury this pole deep inside your cunt." We broke things off and headed toward the bed. I positioned Patricia on all fours and prepared to give it to her doggystyle. Ramona crawled underneath Patricia and lubed up her pussy with her tongue.

I held my cock at the opening to Patricia's soaking wet cunt and slid it in, slowly, inch by delicious inch. Patricia let out a little scream each time I went deeper inside her. Before I had it all the way in she had begun to move her hips back against me, fucking me harder and harder.

Ramona was trying to lick Patricia's clit as I fucked her, but she was having trouble maintaining contact. I gave her a little treat, pulling my shiny wet cock out of Patricia's gash and pointing it at Ramona's mouth. Her lips and cheeks were wet with Patricia's juices, but she took the hint and sucked vigorously on my prick.

She used her whole mouth and teeth on my cock, sucking harder than I had ever seen. She was aggressive as hell, nearly making me cum in the process. I pulled my dick out of her vacuum of a mouth and resumed fucking Patricia.

Round two with Patricia proved to be her downfall, as she began to cum just a couple minutes later. As she came, she bent her head down and began to lick Ramona's pussy. Finally she screamed and collapsed in a heap, my cock slipping out of her cunt with a wet, plopping sound.

As Patricia fell to the side of the bed I took Ramona by the hand and helped her to a sitting position. I took her head in my hands and kissed her. She kissed me back even more aggressively than she sucked my cock, as if she was going to suck my tongue out of my mouth. My hands pinched her nipples and that seemed to exciter her further, her hands grabbing at my cock.

"How do you want it, baby?" I asked. "I'll give it to you any way you like."

Ramona looked at me hungrily and then she spoke. "Eat me a little, and then you can split my ass with that monster."

I got between her legs and began to suck on her hairy pussy. My face was covered with her hair as I licked and sucked on her clit. She was writhing on the bed as I ate her, her hands holding my head close to her as she ground her furry muff into my face. She squirted a little as she came and then pushed me away.

"Don't you dare hold back, Chas. I want all of you up my ass. Do you hear me?"

I nodded my head and got her up on all fours. I eased the head inside her anal ring until I felt her sphincter relax, and then I steadily pushed my meat home.

"Oh, God, it's so fucking big," she screamed. "Don't you fucking stop, don't stop!!"

I began to pound her puckered flower with a vengeance. Ramona was good, real good. I had never found an older woman with her kind of energy since Carol. She took everything I had and kept begging for more.

Patricia had recovered and watched us from the side of the bed, her fingers working feverishly on her own pussy, aroused by the fucking I was engaged in with her girlfriend.

I picked up the pace even more as I felt my own orgasm building. The sight of my huge cock sliding in and out of Ramona's skinny ass, shining with her fluids on each stroke, was pushing me over the edge. Finally I couldn't hold it back and began to fill her ass with hot cum. Ramona pulled away and turned around, taking me into her mouth to get the rest of my seed. When I was finished, she licked me clean and then rewarded me with a deep, open-mouthed kiss. That was the first time I tasted the combination of my cum and a woman's ass juices. Ramona was a different animal, that was for sure. I wanted more of what she had given me.

I wanted to try some different things with Patricia, as well. These two women had a lot of sexual energy, and that gave me an idea.

The three of us lay on the bed, trying to recover. Ramona lay across me on one side, with Patricia on the other. Patricia lazily sucked on my cock, not to get me hard, but just to have it in her mouth. Ramona would occasionally reach up to kiss me.

"Carol was right about you," Ramona said. "She told me that you were the fuck of her life. When Patty and I heard about you I knew I had to have you. You could have charged us double and it would have been worth it."

Patricia raised her head from my lap long enough to nod her head.

I looked Ramona straight in the eye. "How did you know about Carol?" I asked her.

"Carol is my cousin. She told me about this boy in the neighborhood who fucked like a man. I begged her to let me in on one of your sessions, but she was selfish about you. I could only imagine what it was like. Now I know why she wanted you all to herself."

What a small world it was. I would never have believed that Ramona and Carol were related, although she did once mention a relative who was jealous of what she had. That was amazing, and it only reinforced the idea I wanted to share with them.

"Ladies," I said. "I have a proposition for both of you."

Both Patricia and Ramona broke off what they were doing, raised their heads and looked me in the eye.

"Next Saturday, the three of us get together again, this time at my place. No charge."

They looked puzzled at my offer.

"It's simple. I haven't enjoyed myself like this since I was seeing Carol. I want more of both of you and I'm not taking no for an answer. Who knows, maybe we can make this a steady date. What do you say?"

Ramona looked at Patricia. "Patty, I'm all for it. There's lots more exploring I want to do with this body."

This time Patricia was at a loss for words. She just smiled and nodded her head. Then she kissed Ramona and the two of them began to lick and suck my cock, getting me ready for round two.

Published 
Written by prairiedogg
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