Dolly the Whore Pt. 02

Even though he dressed and came across as common working class, Jim was actually a very sophisticated man. He'd traveled the world as a merchant seaman, in fact that is how he'd saved enough money to be a landlord of several properties. He spoke Spanish, was well read, and was a gifted conversationalist. One would never know this to look at this ordinary looking man in blue workers clothes who drove a truck.

Jim had a mildly perverted side. He'd set up the table with table cloth, candles etc like a dinner party only I was in my lingerie, semi-naked, and it was like a date. Then half way through he'd come over and stand in front of me, and I'd suck him off. Jim insisted on shooting his load on my breasts and on my face, then he liked to have me sit there with cum all over my face and tits and we'd talk just like it was normal dinner party conversation.

As you can imagine, it wasn't long before I was straddling Jim and bouncing up and down on his cock. His enormous cock was giving my tiny little Asian pussy the juiciest squirting wet orgasms, and I was simply loving our little 'arrangement'.

I didn't mind doing it. I didn't mind any of it. I figured this was my side gig, and it was a hell of a lot better than having to take an actual second job to pay the bills.

About three months into our little arrangement, Jim floated a proposition. He asked me if I would like to make some real money, better than what I was making at my stupid job. I had a pretty good idea where he was going with this. His offer was for me to be his personal prostitute, and I would be allowed to stay rent free along with a small cut of the profits, 20/80 to be exact.

"Don't be in a hurry to respond," he said. "I want you to think it over very carefully." He went on. "You're the perfect little Oriental Barbie Doll. You will always make good money, men will love your little pussy. All you have to do is pleasure them for a short time until they are done."

Quite frankly, I was a bit surprised it took him so long suggest this. Jim pointed out how I already was doing it for money, so it's not as if I was crossing any kind of big threshold. When Jim mentioned how much more money I could be pulling in, and pointed out how I could quit my job altogether and have a lot more free time, I agreed to it.

"And not to worry," he added, "I will install a security camera in case any incidents arise, and I'll be nearby to help you out, to make sure bad things will not happen."

He was right, I made good money doing it. Jim managed things, he would line up the 'clients' whom I would 'entertain' about five times a week, and at first it was exciting. Before I was Dolly the hard working shop girl. Now I was Dolly, the Professional Woman. Dolly, Love for Hire.

I would meet the men who came to my flat dressed in the expensive lingerie Jim bought for me; sexy bras, G-string panties, sheer see-thru robes and of course thigh-hi's and heels. He had me done up as a perfect little Asian fuck toy, and based on the twenty percent I was pulling in for each 'date', the men were paying top dollar for my services.

But after a few months it got boring. As time went by, I would often just get naked and lay on the bed, the 'client' would do his thing and then he'd leave. There was only one time things got rough with a client, and Jim, true to his word, was in there in a flash. He came busting through the door with a gun in his hand and had that guy grabbing his clothes and out of there in a flash. It was a side of Jim I never saw before, and hoped I would never see again.

Over time I came to accept my role as a Filipina whore. Jim was my pimp, selling my pussy - and the rest of my body - to a list of clients that he brought in. I was Dolly, the Whore.

Still, it paid better than waiting on tables or working retail - a LOT better - and the hours were a whole lot better. I still played around with Jim, of course, only now he was tipping me each time because now the arrangement was different. I know this sounds strange, but with Jim it was more like we were lovers than anything else. Beyond his gruff, working man exterior, Jim was a sensitive, sophisticated soul, and I loved that part of him, loved being with him. The fact that I was his hooker and he was my pimp was besides the fact, something that didn't seem to make any difference. Other than the fact that if it wasn't for our special arrangement, we wouldn't really have any relationship at all.

We took things even further. It started out in the shower; I was facing the wall and Jim was behind me, rubbing his hands all over my soapy tits with my straddling his hard cock like I'd done many time before -- not in me, but me riding his cock like a witch's broomstick. Jim always paid special attention to my pussy and my ass when we moved our hands all over our soapy bodies. This time, I had my hands on the wall when Jim moved his thumb right on to my butt hole and slowly started pressing it in. "What are you doing, Jim?" I asked.

"I'm sticking my thumb up your ass, Dolly," he said, and in it went.

I went up on the balls of my feet, trying to escape his intruding thumb but there was no escape -- he was in there deep, and he was too big and physically stronger than me, all I could do was wiggle helplessly within his grasp while his thumb invaded my most private place.

At the same time he was rubbing my pussy with his other hand and once I got used to his thumb up my ass it really started to feel good. I was totally impaled, penetrated in the rear, pinned to the wall, unable to escape while at the same time being diddled and finger-fucked.

I began to slip into a strange out-of-body experience as Jim fucked me in the ass with his thumb. The effect of being fucked in the ass while my pussy was simultaneously finger-fucked obviously did it. Jim kept sodomizing me with his thumb, he was basically raping me in the ass, and I was loving every minute of it.

I began going into an extended series of orgasmic convulsions, incredibly enough, even as Jim's thrusts up my anus became harder and more purposeful. He had me pressed against the tiles, my face was up against the tiles, eyes shut, lips parted, the running water splattering down on me as I took it, took his big thumb right up my butt.

My pussy started gripping his fingers tight, clenching hard as he continued to plunge his thumb up my asshole. Then I finally went over the edge

"Ah... ah... AHHH!!!" I sighed as Jim's talented fingers brought me to an intense orgasm, one unlike I had ever experienced before. Wave after orgasmic wave rolled over me until finally I collapsed in Jim's arms, a quivering piece of meat.

Drying off afterwards, I said to Jim, "That was something different."

"Yes," he replied. "You need to learn how to take it in the ass."

"Why?" I asked.

"Because men will pay more to do you that way. A whole lot more."

By now I was completely sexually liberated, open to anything, but I asked, "Won't it hurt?" Jim's cock was a lot thicker than his thumb. So were most of my clients.

"That's why we have to give you training, to loosen you up, so you can take it back there," Jim said.

"Training?"

"Yes." Jim produced a box, opened it to reveal three curious items such as I had never seen before. Jim had by that time already introduced sex toys into our routine -- vibrators and things like that -- so I could only imagine what this was all about. They were metallic, bulb shaped with a stem and a flat base sort of like a wine glass. Each of these objects was larger than the next.

This was the first time I had ever seen a butt plug.

"Turn around," he said. I complied. "Bend over. Spread your cheeks." I did as I was told, as I always did with Jim. I felt something wet and cold being applied, and then some pressure. Jim was pressing one of the objects into me 'back there'. There was some initial resistance, and then it slid right in.

"There," he said. "It's in."

I turned so I could look over my shoulder at my back side in the mirror. There was a flat, circular metal disc in the crack of my ass -- the rest of the object was fully inserted into my butt hole. It was not uncomfortable.

And so began my butt plug training.

We went into the bedroom and then we had sex, of course -- Jim had not cum yet. I went down on him, using my lips and tongue on his big dick, while Jim stroked my wet pussy and played with my ass. When I went to straddle him, Jim said, "Wait a minute," and then he gently pulled out my butt plug. It felt good as it popped out, I was beginning to be aware of the sensitivity of my anal sphincter.

Jim's huge hard cock felt even better as I lowered myself onto it. As we were doing it, Jim inserted a finger into my lubricated butt hole. I was thoroughly clean back there, and quite stretched out already from the episode in the shower and of course the butt plug, so I actually enjoyed the sensation of Jim's finger in my butt hole at the same time I rode his big cock. Jim had huge hands, and his thick finger was all the way up there, knuckle deep.

I rode Jim's pole to orgasm. I always orgasmed with Jim, this time I experienced multi orgasms as he shot his load of hot cum deep inside me and them collapsed on top of him. Jim was a big man and I'm a tiny little Pinoy girl so for me it was like making love to a giant. I'm sure for him it was like having his own personal Asian Barbie Doll spinning around on the end of his dick.

Before he left for the day, Jim made me bend over and grab my ankles, and he inserted the second butt plug in my ass, the middle sized one. I went to the full length mirror and looked over my shoulder to see the flat disc shaped end of the butt plug in the middle of the crack of my ass. As I moved around my flat, I was very self-conscious of it. All my thoughts seemed centered around the butt plug in my ass.

"You must leave it in twenty-four hours," he instructed.

"Yes, sir," I dutifully replied.

"If you go out to the store, wherever you go, you must have it in," he continued. "You may remove it if you need to use the toilet, of course. And be sure to clean yourself very thoroughly back there before you put it back in."

"Yes, sir." I was always very respectful and obedient with Jim. It was part of our relationship, and like my Mammy used to say, it is a woman's duty to make a man comfortable.