1971. The height of Josie and the Pussycats fame.
Valerie gazed from her hotel window down to the street level far below. She wondered idly which of the men approaching might be her 'escort' or male-ho. She'd specified the whitest boy they had on the books but elected not to spend time looking through their ever-expanding catalogs in advance. All she had was his name, from the booking. She understood that some agencies hired out escorts who would be taken for meals by lonely women, or other dates. Then, like the agency the Pussycats been introduced to by the band's manager Alexander a while back, some just hired out escorts to wealthy people for guaranteed-discreet fucking.
She narrowed her eyes as she saw the particularly milky skin of a forearm far below, and hoped it was her man. As far as Valerie was concerned, when it came to no strings attached tension relieving fucking, white boys were the best. Valerie liked the deep contrast of her dark creamy skin against a white guy's, but she also loved dominating them, making them service her. She patted her dark bushy hair and adjusted her cat ears headband. Mostly satisfied, she then adjusted the sash on her silky robe. Beneath, she wore nothing at all on her freshly bathed skin.
A polite knock sounded on her room's door. Valerie grinned and went to open it. She padded barefoot across the luxuriously soft carpet and opened it without checking through the Peep Hole. There was very little chance a crazy fan or other losers would get past the security at a luxurious hotel like the one she was staying in. That was, besides the discreetness, the other major advantage of the escort agency. All of the escorts were regularly health checked and guaranteed disease-free - something that certainly couldn't be said for using groupies or roadies.
Jay - not his real name - stood outside the hotel room door. He was very new to escort work and still pretty nervous meeting clients. He didn't know any other escorts with the agency, which was how the company liked it, and so hadn't been able to call on more experienced guys for advice. He did assume that they were mostly like him; good-looking guys from reasonably well-off families who just needed a little extra money, and whose future career choices should help ensure they were quiet about spending a spell fucking for cash.
His only two previous clients had supposedly been celebrities, but he'd only vaguely heard of one of them as being from a game show. He'd hidden it, though, for both made sure to drop in their shows and "be recognized". In some ways, it'd made the job easier than he was expecting - like picking a random girl up at college, except with everything geared towards what the women wanted, and nothing for his own needs.
Physically, Jay was exceptionally pale-skinned, with tousled orangey-red hair that wasn't quite true ginger, and even freckles on his face and down his arms. His skin always seemed to burn rather than tan, and so had to avoid the booths at the gym and slap on sunblock in the summer. His build was athletic without being over-ripped, and his height average.
The way the job usually worked was that the clients would book into a hotel under an assumed name, and it was agency policy not to tell the escorts who they were really servicing in advance. So it was that when Valerie opened the door and Jay instantly recognized her as one of his favorite performers he nearly cussed with shock. Anybody who said Josie and the Pussycats was only a band for teeniebopper girls sure hadn't heard or seen them play. Especially seen. Jay reined in his surprise and smiled warmly at the star. He even tried to maintain eye contact, though his head wanted to pull down the visible valley between her breasts. He would have succeeded if Valerie hadn't been checking out his body with obvious approval.
"Hello, Jay. I guess you know who I am, huh?"
"Yes, Ma'am."
"Well, come on in white boy. I want a better look at that butt!"
Jay entered the room as Valerie stood back. She swung the door shut behind him and shimmied around to grab his ass.
"Oh yeah, that's a nice ass. I bet you work out some, huh? Mmm-Mmm! Aren't you just delicious?"
Valerie noticed Jay seemed a little nervous, but it wasn't going to slow her down none. Theoretically, she had the whole night paid for with him, but she never seemed to last all that long. One or two orgasms were normally enough for the performer; she wasn't like Josie, who needed it all night long. Valerie would often drift off to sleep utterly relaxed after a fuck or two, with not a care in the world.
"You ready to get started, you need the toilet or anything first?"
"No, uh, I'm good to go."
"Strip off then, boy! Show me your body."
Valerie moved away from Jay and sat on the end of her bed. In Jay's nervousness, he didn't notice that she sat in a slightly odd position, more like a guy might sit if he wanted to hide something. He wasn't any kind of striptease expert, but he gave Valerie a bit of a show as he removed his clothing and piled it neatly to one side. If she noticed his inexperience, she didn't show it. She smiled and whistled to see his flat stomach and defined thighs. Jay's cock hung flaccidly down, a decent size even then.
'Exactly what I wanted,' thought Valerie, pleased with how Jay's buttocks seemed an even milkier, paler, white than the rest of him. She was able to hide her own excitement only through months of practice with tight clothing. She'd had to learn after The Countess, whose scheme was far more devious than anti-aging on that occasion, had captured the Pussycats again... Valerie beckoned Jay over to her once he was completely free of clothing, and got him to kneel on the carpet before the bed.
"I've paid for you to do whatever I want, right?"
"Yes, Ma'am."
"Call me Valerie. I don't wanna feel like I'm fucking the guy in the diner. I did as much of that as I wanted to do before the band. Now, in a moment I want you to suck on my nipples, play with my breasts, make me feel real good, okay?"
Jay nodded, "Sure Valerie."
"Good boy. Before that though, I just want to check. Seeing as I paid your agency and all and you agreed to come here you ought to be fine with it, but just tell me this: Are you okay with anal sex? I mean, I got lube, ain't talking 'bout forcing it in dry"
Jay blinked, "Uh, sure."
'Hey cool,' he thought 'never thought I'd get the chance to put it there.'
Valerie pulled Jay's head towards her chest, and he gently tugged open her robe. Jay's cock began to stiffen as he laid eyes on Valerie's dusky breasts. As fine a pair as he had ever laid eyes on, with the firmness of youth and the rounded maturity of a young woman. He licked his tongue around a soft black nipple and then kissed around it. Valerie moaned softly and urged Jay to suck harder. He eagerly complied, lathering Valerie's sensitive nipples with saliva as they hardened and stood out stiffly from her breasts.
Valerie pressed forward and pulled Jay's pale face into her cleavage. He nuzzled the valley of her breasts for a moment before she released her grip, and went back to her nipples. He brought his hands up, using them to stimulate Valerie further. Her moans grew louder and she thought his initial foreplay excellent. As Jay kissed up her collarbone while massaging her breasts, her robe was pressed open below the belt.
Un-noticed by Jay, Valerie's uncut penis grew proudly erect from her crotch. As the singer's arousal grew her cock hardened to an impressive length and thickness. Veins throbbed along the length as her foreskin rolled back around the slightly twitching dark purple crown. A stream of pre-cum leaked from the slit on the top. She felt her balls shift as she changed position on the bed slightly, hanging between her dark-skinned thighs.
"Yes, yes, white boy! You got my breasts feeling real good," Valerie groaned to Jay, "Now go down."
Jay's own cock had grown hard, and while not as impressive as Valerie's was certainly nothing to cause a shy bladder either. He kept his ginger bush neatly trimmed and had been circumcised just after birth. He caught Valerie's eye as she finished speaking to him and smiled, before looking down and feeling an incredible burst of shock.
"Holy shit! You have a...um... You don't have a pussy," he managed.
"Far as anyone outside this room is concerned, I do. I paid good money for you to do whatever I want, so suck it, cracker."
"But... how?"
"Ever hear of a mad scientist type calling herself The Countess? Got her own island?"
"N-no."