The Initiation

Chad was an exceptionally beautiful boy. 20 years old, long blonde hair and pretty blue eyes. A lean and toned athletic body, he was the exact kind of prey that Jessica hunted. She had been watching him from across the bar where he was working as a bartender.

Jessica was always on the lookout for young prey, she preferred her boys pretty and young. She liked to dominate, to be served and to wield her cougar power. At forty her considerable breasts were still perky and firm, years of exercise had ensured that. Her deep dark eyes were focussed on Chad for the last couple of hours when she finally decided that it was time to make her move.

She ordered another drink and slipped the waitress an extra fifty dollars. The waitress was more than happy to tell her all that she knew about Chad. The young man was trying to pay his way through college and the city life by working as a bartender. That's all Jessica needed to know, she had her move.

"Chad, right?" she asked, moving to the bar and finding herself a seat.

Yes, how may I help you? Said the young man, slightly surprised as she was already holding a drink.

Just come to this address once your shift is over, she told him, handing him an envelope and then left.

Chad was even more surprised, he didn't quite have time to react before she left. An hour later he was about to leave for home after his evening shift when he remembered to check the envelope.

There was her address, in an upscale part of town and a thousand dollars in cash. That was a lot of money for a young man struggling through college and city living trying to make it on his own. He knew there was a catch but he was terribly tempted to find out what.

Jessica had a curious thing going on. She didn't like hiring escorts but she almost always liked to buy the services of men like Chad. It added to the humiliation and she got off on humiliating her boys. And, she could afford it. Being a billionaire had its advantages.

And sure enough, it wasn't too long till the bell rang. She answered the door, still wearing her work clothes. High heels, a crisp suit and a mid length skirt. She hadn't changed yet, she anticipated that Chad would come and she wanted him to work hard to earn his keep. It wasn't a date and she wasn't going to freshen up for a whore!

Do you know why you are here? She asked.

I have a fair idea, he shrugged. No one leaves a thousand dollars and a address as a tip, he said, feeling a little cocky and bold. After all, she was quite good looking herself and what red blooded young man doesn't like the ego trip of being thought attractive?

You have no idea at all boy but you will soon enough! I have already given you more money than you make in a month and there's another such envelope waiting for you at the other end of tonight but to earn that you have to be the object of my pleasure.

Yes, can do! He was making a neat amount of money for having sex with a beautiful red head! Sure, it was slightly humiliating if he thought of himself as a whore but come on, two thousand dollars for a night of sex with a beautiful woman; it can't be that bad!

There would be no sex, boy! She said, almost reading his mind. You are to be my whore. You will spend the night pleasuring me and doing everything I ask of you. If that is agreeable to you then strip naked and present yourself to me now or you can get out and keep what I have paid you already.

This wasn't turning out like he expected but how bad could it be, he thought. Besides, as much as he didn't want to admit to himself, the money was a temptation.

He stripped almost immediately, one night, two grands and a beautiful lady. Too many temptations to resist.

She held his cock like a leash and walked him over to the sofa. It was a nice sized cock, circumsied and she liked that he kept it hairless. Turn around and strut your entire body slut, she said as she found herself a seat.

He felt a little humiliated but his cock had already hardened at her touch and curiously at whatever was happening to him. He decided to play to her whims, she was, it was clear, a very dominant woman, but if played his part right maybe he could get a shag out of tonight as well, he thought.

Kneel before your goddess, pet and show me your tongue. You are going to be using that a lot tonight. Jessica was moist already and couldn't wait to have her fat pussy worshipped but she needed to show him his place first.

Take off my heels, bitch boy and kiss my feet. Verbal humiliation was another turn on for her. He kind of expected this and went about his job in a professional way. He slavishly kissed her feet and sucked her toes knowing well enough that soon he would have to move up. He had been licking her feet for about ten minutes, when she finally asked for his mouth on her pussy.

Lick my pussy, slave she said as she pulled him by the hair, right into her crotch. Her skirt had been pulled up and panties moved to the side. His tongue entered her musky crevice and he found it wet already. But he hated the hair. He liked his women clean shaven down there. He wasn't calling the shots though.

Soon, she was naked from the waist down and his tongue was working her hairy jungle. Her hand reached into her blouse and popped out a delicious breast. She sucked on her own breast while he feasted on her pussy.

Work that slave tongue on my cunt, bitch. Earn your whore fees. Eat that hairy cunt, I want to see your pretty face drenched in my juices, she shouted as she gripped his hair tight.

Suddenly she pulled his face away and slapped him hard but before he could even react to the stinging slap, his face was pulled back into her tight vagina. She slapped him again and again, repeating the process twice which seemed to have sent her over the edge. She gripped him tight, her thighs closing in on his face. She came like the summer rains, drenching his face and mouth in her juices.

Swallow! Swallow my nectar you cuntlicker, swallow all of it. Five minutes later, he was still cleaning up her juices from her pussy and inner thighs. His head ringing from the slaps, his face red and wet. He was the most beautiful thing to Jessica at this moment. Covered in her superior juices, cowering at her formidable pussy. Her own private whore, her pussy licking bitch.

The evening had just started. As had the humiliations.