Anal Queen 1

Anne Courtney was the bastard child of a floozy named Beatrice Courtney. Beatrice was a hooker that worked the east side of Cleveland, Ohio during the 1930s.

Beatrice's little accident, as Anne was called, was raised in flat above a shabby furniture store, just a block from Stoney's Bar, until the age of 12.

Beatrice worked out of Stoney's Bar and specialized in half and half scenarios. She would suck, and edge guys, then let them cum in her pussy, followed by a quick douche. This normally kept her safe from pregnancy, but was not foolproof, as little Anne would attest.

Beatrice would put Anne to bed then head to Stoney's to work her trade. Beatrice and several other girls kept a flat above that same furniture store, where they turned their tricks. After turning a trick, Beatrice would sometimes check on little Anne, but not always.

Some nosy busybody turned Beatrice into Social Services, and Beatrice was hauled before a local Judge for child neglect and endangerment. The Judge ordered Anne to be removed, and put into Social Services protective custody. From that time, until she turned 18, Anne was in and out of Foster Homes. At 18, Anne returned home to be with her mother.

Beatrice, was now servicing clients in her own flat, saving the cost of a second flat. This is the environment that Anne had returned. Anne was far from naïve, and was well aware of her mom's work.

Anne had grown into a stunning young lady, and soon became an attractive addition at Stoney's bar. Anne would sip ginger ale and pretend to be drinking something stronger. She easily passed for 21.

Men hit on her constantly, even Stoney. Anne realized how easy it would be to make money from her mother's profession, but she was paranoid about getting pregnant, like her mother, once did.

Stoney offered Anne a full proof alternative. He suggested he fuck her in the ass. No chance of getting pregnant that way. He even offered her $15, which was the going rate for a half and half. Anne was not sure, and told Stoney, she would think about it.

Stoney continued to work on Anne, as he desperately wanted to bugger her. He assured her, she would not get pregnant, and that if she liked it, it would be a great way to make money.

Beatrice helped Anne, make her decision, as she informed her, she needed to start helping with the money situation at home. Beatrice said she was more than willing to help teach Anne the trade. Anne said she would think about it, but secretly decided to take Stoney up on his offer.

Anne needed money, but her paranoia of getting pregnant, made her opt for Stoney's offer. Stoney was ecstatic, when Anne told him she wanted to try his suggestion.

Stoney took Anne to his apartment above the bar and asked her to strip. Anne complied, and as her clothes came off, Stoney removed his cock and began stroking it to full hardness. Anne stood nude in front of Stoney, and heard a low whistle from Stoney, as he took in her voluptuousness. Anne's eyes were fixated on Stoney's hard cock.

Stoney thought, damn, this young honey is so awesome, I could make a fortune, as her pimp.

Inexperienced Anne, was not aware that Stoney's cock was much bigger than average.

"Baby I need to prepare you for what you are about to receive. My cock is bigger than most, and I do not want to cause you a lot of discomfort," Stoney said.

Anne thought, I appreciate that, I think.

Stoney removed his clothes and took a bottle of lubricant from a drawer. He told Anne to lie down on the bed face first. Stoney applied a large amount on lubricate to his fingers and inserted on Anne's tight ass. Anne felt some slight discomfort, but not a lot. Then Stoney inserted two fingers, followed by three. As Stoney finger fucked her ass, Anne felt a warm feeling coming over her. It was nice.

Stoney was opening her up for his cock.

Stoney applied a good amount of lube on his cock before inserting. Once he started entry, Anne felt a little more discomfort, but not much.

Stoney said, "God, baby your ass is tight, but you're doing great."

As Stoney penetrated deeper, the warm feeling returned to Anne, and it felt wonderful. It was all Stoney could do to restrain himself from jack hammering her ass. Stoney began fucking her deeper and deeper until his big cock was fully inserted in her ass. Then all bets were off, Stoney began fucking her ass with almost wild abandon.

Anne thought, fuck, I love it.

Then Anne could feel an orgasm welling up inside of her. She was about to experience an anal orgasm. Stoney was on the verge of orgasm, as well.

Stoney and Anne reached orgasm almost simultaneously. Anne screamed out in ecstasy, as Stoney bellowed. The noise of the bar below drowned out the sound.

Both Anne and Stoney were well satisfied and sated. Chatting later, Stoney explained to Anne that she had great earnings potential, but needed a handler, a.k.a. pimp. He further explained that he had contacts with men with money that would pay big to fuck her in the ass, and offered to be her handler and manager. All he wanted was 10%, and the chance to occasionally fuck her awesome ass.

Anne said she would have to think about it.

"Here is something to think about, that also ensures you will not get pregnant. It is called cunnilingus. These same men who will pay big to fuck you in the ass, and will pay to eat your gorgeous pussy," said Stoney.

Anne was intrigued, but also at the same time, somewhat dubious.

The next time they met, Anne said she was interested in Stoney representing her for anal sex dates, if the price was right. Stoney suggested that they start at $50 per trick, and if things work out, perhaps raise that to $100. That would ensure a higher class of clientele. Anne was in agreement.

Stoney then asked if Anne had considered the cunnilingus part. Anne replied, she had never been eaten before, so she was not sure. Stoney was more than willing to demonstrate for her.

Anne got naked, and climbed on Stoney's bed, and spread her legs. Stoney got between her legs, and snaked out a long tongue. As he swiped his tongue across her pussy lips, Anne lurched, and thought, damn that felt good.

Stoney was very good at cunnilingus and soon had Anne screaming and bucking. He brought her to orgasm when he took her engorged clit between his lips and sucked it like a small cock. He brought her to many orgasms before she feinted, dead away.

When she came around, she said, "Damn, Stoney that was awesome."

Stoney's devious mind thought there was another way to make money with Anne, and that was, to make her available for Lesbian cunt munchers. But that can wait, he thought. He knew he had a sure-fire money maker in Anne.

Stoney contacted a well-known Cuyahoga County Judge that was known for favoring young ladies. The Judge was intrigued when Stoney said she was available for buggering for $50. Stoney further explained, if the Judge wanted to eat her pussy, the price went up to $75.

The Judge thought the price of $75 was a bit steep, but if Anne proved to be as good, as Stoney claimed, she might be worth it.

The Judge kept a suite at a hotel that catered to prominent men in the Cleveland area. Anne arrived right on schedule, which pleased the Judge, and the old gent was virtually drooling at the sight of this nubile young lady. Stoney had purchased her a sexy outfit, which best displayed her assets.

Anne found the Judge to somewhat distinguished looking, with a bit of a tummy, but otherwise, not intolerable.

The Judge greeted her by say, "My dear Stoney's description of you was not exaggerated, you are simply divine."

A nervous Anne responded, "Well thank you sir."

The Judge appreciated her good manners.

"I thoroughly love the sexy outfit you are wearing, but would love it more, if you removed it," the Judge said.

Anne, did her best strip act, as she slowly removed her clothes, until she stood nude, with the exception of her high hill shoes. The Judge was breathless.

"Oh my god," the Judge said.

"Am I the only one to be nude?" Anne asked.

"My dear, I want to request you undress me," the Judge said.

Anne did, as requested, and began removing the Judges clothes, one piece at a time. When his hard cock came into view, she viewed, her first uncut cock. She also noticed the Judge's cock was not a large as Stoney's cock.

Once both parties were totally nude, the Judge said, "I want to taste that lovey pussy of yours."

Stoney had prepared Anne by trimming her lush bush into a neat small strip above her pussy lips Stoney knew the Judge did not like excess pubic hair. The Judge was impressed.

"Get on the bed, my dear, and spread those lovely legs," the Judge said.

Anne did, as requested, as a cold chill ran through her entire body. The anticipation was intense.

The Judge crawled between Annes legs, and snaked out his long tongue. He was delighted to find a pussy that was already wet. Just like with Stoney, Anne lurched and moaned, when his tongue licked her pussy lips.

This was not the first rodeo for the Judge, he was an experienced pussy eater, and he proceeded to give Anne his best. His attention to her now engorged clitoris, had Anne on the verge of her first orgasm. Anne was thrashing about on the bed, and moaning and mewing.

Damn, he is even better than Stoney at eating pussy, Anne thought.

Soon Anne was rolling with small orgasms, with the big one building deep inside of her. When it arrived, Anne bucked her cunt up against the Judge's face, and coated his lips and face with her orgasmic juices, before slumping back down on the bed.

The Judge never had a woman cum quite like that before, when he performed cunnilingus. He was delighted, and felt his hard cock ache.

Both the Judge and Anne needed a short break before continuing. During the break the Judge's cock deflated some and he was concerned it would not get hard enough to bugger this sweet girl.

That is when he said, "I will need some assistance before fucking your ass."

"Assistance," Anne queried.

"Yes, it would help, if you sucked my cock back to full hardness," the Judge said.

Anne was taken back, even Stoney had not requested she suck his cock. She had not contemplated that, and said, "That was not part of the deal."

"My dear, if my cock does not get hard enough to fuck your ass, you will be making $25 not the $75, that you expect," the Judge said.

After considering what the Judge said, Anne agreed to suck the Judge to full hardness, but she warned the Judge, "I have never sucked cock before."

The Judge presented his semi hard cock to Anne's lips. Anne opened her mouth to speak, but the Judge shoved his cock in her mouth. "Suck," he said.

Anne began sucking, and was quickly admonished, "Watch your teeth girl."

Anne felt the warmth of the Judge's cock, as it began to throb and grow. She was actually enjoying sucking his cock. As much as the Judge wanted to bust a nut in Anne's mouth, he wanted to fuck this hot young lady in the ass even more.

"Better stop," he said.

The Judge then positioned Anne on her back with her legs in the air. Anne first thought, he is going to fuck my pussy, and said, "No, no, not in my pussy."

"Not to worry my dear, I'm going to fuck your ass, I just want you in a position I can see your face as I'm buggering you," the Judge said.

Anne relaxed, as the Judge lubed her tight ass, and his hard cock.

When the Judge presented his hard cock to Anne's, puckered hole, Anne felt a rush, and was ready for the Judge to make entry.

As the Judge's cock eased in, Anne felt a slight tinge of discomfort, but that was soon replaced by the same warm wonderful feeling, she had experienced before.

After bottoming out in her bowels, the Judge picked up the pace of his strokes, and was soon slam fucking Ann's ass.

Anne was moaning and mewing, as the Judge grunted.

"Damn, what a tight wonderful ass you have. Better than any cunt I've fucked," the Judge bellowed.

Anne followed up by screaming "Yes, fuck me!"

Anne felt an anal orgasm building. The Judge also felt his orgasm building, while he continued to pound away.

Then, as if by magic, they each reached a mind-blowing orgasm simultaneously.

After coming down from their orgasmic highs, the Judge's cock slipped from Anne's ass, and he said, "My dear, that was wonderful."

Anne could only nod in the affirmative.

When paying her, the Judge gave Anne an extra $25 saying, "That is for sucking me hard again, you need not tell Stoney about it. Just consider it a tip"

Anne said, "Than you sir.

"No thank you, and tell Stoney I will be in touch., I know a lot of prominent gentlemen that will pay handsomely to fuck your sweet ass. I can think of parties where you could make as much as 500 to 1000 dollars. However, I suggest you work on your cock sucking skills," the Judge said.