Michael and Carol came to her apartment after their eventful evening at Carol's sex boutique. Michael had been sent to her shop by her friend Laurie to buy a strap-on and Carol had decided to teach Michael a lesson.
Carol's door opened into a wood paneled foyer and once inside her apartment seemed luxuriously furnished with big pane windows in the living room overlooking the city lights. Once inside, Carol pushed him into the spacious guest bathroom and ordered him to clean himself thoroughly. She warned him that he should scrupulously follow the typed instructions on the sink or his punishment that night would be far worse than he could imagine. Her directions on the note were explicit and he was again filled with the delicious mixture of shame and sexual excitement at what he needed to do. He hurriedly looked at what was in the bathroom. An enema was a requirement and he removed the chained butt plug to get started. As he turned around to look at his bottom in the full length mirror, he could see that the unusual plug had worked and he was not puckered shut but gapingly open. He used the nozzle to fill himself with warm soapy water and had to use the cloth padding to hold the liquid inside. After releasing the liquid, he then stepped into the shower to shampoo and soap himself thoroughly cleaning his penis and his bottom. His cock was painfully erect from his arousal. He longed to use his hands to bring himself off but the instructions were explicit about this and he did not dare provoke Carol's wrath. Drying himself, he used the moisturizing oil all over his body. He went over his face and neck with a brand new razor to make sure he was still smooth. He did not put on the cock ring and the butt plug as they were not mentioned in the instructions but cleaned and left them on the sink. The wrist and neck leather bands were required and these he dutifully refastened on himself.
He looked at the makeup instructions next and it came attached with the picture of a woman whose appearance he had to emulate. The image looked oddly familiar and then he realized that the girl resembled one of the identically made-up dancers from a Robert Palmer video. He started with his hair, gelled it, combed it back and cinched it in a severe ponytail. Big metal loop earrings went on his ears. He then applied the heavy pale pancake makeup followed by the deep red lipstick and the shiny gloss. Gluing on the extra long lashes and applying the thick coat of mascara took a lot of concentration as he was not very experienced doing this. Deep blue eye shadow and extra pink blush for the cheeks completed his face. His face could have passed for that of a street walker, albeit with much more expensive makeup. He dabbed on the strong perfume behind his ears, on his wrists and between his thighs. At that time, he did not think too much about why he was using waterproof makeup but the reason would be clear to him later that evening.
The clothes came next. He had to slowly slide on the black fishnet stockings so as to not rip them. A black lace garter belt came next to hold up the stockings along with a leather g-string. A micro-mini flared leather skirt, similar to the one Carol wore earlier that evening, fitted perfectly around his waist. The top she had set out for him was a black leather corselet that was adjustable with strings at the back. He tried it on a few times adjusting the strings till the fit was right and then fastened the small hooks in the front. Finally, the black platform high heels went on his stocking clad feet. He tottered up on the unfamiliar shoes and looked at the full length mirror to see an attractive girl, not very busted, but looking hot nevertheless. He could imagine himself as an escort, eager and available to service clients. The excitement increased his erection which pushed against the top of the tiny panties.
He walked out of the bathroom still a little unsteady on the high heels. Carol was not in the living room so he tried to sit on the leather sofa and found it uncomfortable with the clothes he was wearing. The leather skirt had flared open so he ended up sitting on his nearly bare bottom. It was now well past 10pm. Just then Carol walked in and he shot up from the sofa startled. Michael looked down at her feet as she closely inspected his new appearance. "Turn around", she barked, looking carefully to see that he had obeyed her commands. He looked just like one of her favorite girls and seemed to fit into her clothes very well. Voicing her approval she went over to the bar to pour them both drinks. It was then that he took a good look at her. Her feet were in nearly 6-inch tall stiletto heeled boots that went all the way up her thighs. The shiny black patent leather boots had rows of silver buckles on the outside. She was wearing a black crocodile leather patterned jacket that came to her mid-thigh. The coat's stiff upright collar covered her neck from the back so you could only see the top of her upswept hairdo over the collar. With her patent black leather gloved hands, she poured two large glasses of the Hanger One vodka with two cubes of ice each and turned around towards him. Her makeup was flawless just like earlier that evening although she had switched to more dramatic colors of eye shadow and lipstick for the night. She wore long dangling gold earrings and a thick intricately patterned gold chain on her neck. He could now see that she wore a tight black silk and satin corset that pushed up but left bare her breathtaking breasts. Her deep chocolate brown nipples stood out erect on her large brown mounds. The corset ended at her waist and left her proud shaven mound bare, adorned solely by the trim rectangle of wiry black pubic hair on top. He realized that if she so desired her coat could be snapped shut with buttons at her midriff, concealing her breasts and crotch to casual observers and preserving a modicum of modesty. She looked like a magnificent tigress out on prowl!
She handled him the vodka and ordered him to drink it fast. He gulped it down and the searing liquid burned through his throat down to his stomach. The alcohol quickly had its effect on his empty stomach as he felt wild, uninhibited and sexy. She too slugged down her drink and gestured for him to come close to her. She towered over him in her boots and he felt small next to her with his face coming up against her exposed beautiful brown breasts. Grabbing him by the base of his thick ponytail she bent down and pulled his face up for a deep kiss while her other hand cupped his bottom to lift him up to her. Her tongue invaded Michael's mouth possessively frenching him. Her gloved finger pushed aside his flimsy g-string and penetrated his anus. She used her finger to fuck him probing to press his prostate. He moaned with need as her finger filled him. When she abruptly released him he felt empty and slumped down next to her. "Slut, you will have a lot more of that tonight and I'll make sure your butt is nice and red with pain before I take you hard with the strap-on. But, I want your hands and mouth continually catering to my pleasure. You are my pet and I need you to be pressed up next to me. Don't let me tell you this again!" she ordered.
Michael hurried to the bathroom to fix up his makeup and hair. He was then dragged along on his heels as Carol rapidly exited the apartment building. It was now nearly 11pm and they were on their way driving fast to Carol's favorite club.
Carol drove Michael out in the Jaguar at predictably fast speeds down towards the waterfront. This time her hands stayed on the wheel and he missed her teasing of his cock. But fearing her explicit orders he pulled against the seat belt to bring himself close to her and ran his hands over her thighs but could only caress her leather boots. Arriving at the club which was in one of the many warehouses that lined the docks, she pulled up to a valet parking station and handed over her car. The valet's eyes nearly popped out of his head seeing her gorgeous bare breasts and naked pussy.