Chapter 5

The destitute babysitter Tiffany (Tiff for short) was making lots of cash at the Casino that was under the control of her new boss Carmine. She hated that she could not spend as much time with Billy and Jane Singleton because they had both been taking care of her nocturnal urges on a regular basis ever since the first night she had babysat for them.

However, she had to face up to the fact that she had squandered her income on cosmetics and clothes as well as some unusual sex toys that gave her tingles in all the right places. Her need for cash was too severe for her to ignore and she took the well-paying job at the Casino to entertain visiting VIPs willing to pay top dollar for renting the use of her nubile young body for their depraved fetishes.

In a way, she was appreciative of the fact that her clients were all perverts in one way or another and it was not just straight forward sex because it made it look more like gaining experience rather than plain old sordid prostitution. A few of her school chums had taken the bad girl route and she knew they were quite unhappy with their fall from grace and depraved lifestyle.

Some of the fetishes the rich and famous were obsessed with were so ridiculous to her that she failed to consider them as actual sex because it was so far from normal that she saw it all as a specialty act just like an actress on the stage for their uniquely personal entertainment.

She had to send the Singleton’s her regrets for this very evening because the Casino boss had promised her a fee of five hundred dollars for four hours work and she would be allowed to keep all tips for herself. The added incentive of the tips was a big ticket item because she had discovered that the tips often were more generous than the actual fee for accepting the assignment.

Apparently, she was to have an assistant on this party because the ex-military bitch from hell called Dixie was already dressed up in all black leather with openings cut out for her breasts and with an open crotch between her legs and a nice little round circle in back for her ass cheeks to be framed with a circle of thick black leather. The sight of the woman’s creamy white globes up above and behind were about as pornographic as possible and the fact that her face was nowhere near as beautiful as Tiffany’s didn’t seem to matter considering the perfection of her nubile flesh.

Tiff didn’t like the way Dixie grabbed hold of her ass cheek and squeezed like she was a piece of fruit for sale at the market. She was getting ready to call her on it when the girl reached down and slid her hand inside her panties and stuck her middle finger right up her sensitive vagina. It was so unexpected and uncalled for that she just stood there on her tippy-toes and realized Carmine was watching her for a negative reaction. She knew instinctively that he would probably slap her silly if she showed any reluctance and she pretended it was all a joke and opened her legs for Dixie to get in as deep as she wanted without any protest at all.

It was a lot different from the “fooling around” sessions with Mrs. Singleton where they timidly exchanged favors to make each other feel real good when Billy was too busy to give them what they needed at those special times after midnight.

Dixie reached down inside her dress to cup her breast with a demanding hand and devious fingers that pinched her sensitive nipple with a mean-spirited desire to make her whimper in distress. She refused to show the woman that she was shaken right down to her core and pretended that it was nothing unusual to be treated like she was a doll on the shelf ready for play.

The older woman took her by the hand and led her to the elevator taking them up to the penthouse suite where the high-rollers soaked up the free perks of gambling in six figures. The first thing she noticed was that there were no young guys under forty floating around the huge room that opened out onto a rooftop veranda with an Olympic-sized swimming pool that had diving boards on the far end.

Tiff was glad that she had worn her special French undies because she suspected her hidden underwear would be on display one way or the other before the night was concluded.

Dixie went over to the leader of the quartet playing upbeat modern jazz just inside the glass doors leading out to the pool area. He was a tall, dark-skinned guy in his forties with a throwback hairdo that made him look a bit younger. She came back over to Tiff and told her,

“Get your ass in gear, babe, we got us a couple of hot ones outside by the shallow end.”

Tiff followed her swaying solidly packed flanks out to the pool and Dixie walked right up to a table with two out-of-shape middle-aged guys both wearing glasses and looking like they wanted to eat a pair still teenagers girls in Brazilian swimsuits with absolutely nothing covering their ass cheeks except for a tiny little cord that ran vertically in their cracks like some offering to common decency.

Both girls had no tan line to mar their perfect brown skin and when they walked or jumped in or out of the water their buttocks bounced like rubber balls just released from the factory.

Tiff knew her own cheeks were just starting to droop a little because she had been doing little or no exercise lately with her busy schedule. Still, Billy told her privately that her slight compromise with gravity was sexy as “hell” and that she was still as tight as a teenager where it really counted.

The moonlighting babysitter had to admit that Dixie had a butt that put both of those girls to shame and Tiff figured that the ex-military female was hitting the exercise trails every day to keep her youthful appearance and her picture of healthy fitness.

She sat down silently next to Dixie letting her do all the talking for both of them.

“You boys must be Dave and Harry from Ledbetter Insurance, am I right?”