Annie's Game

The room inside was a stark contrast to the grimy industrial estate. It was warmly lit, the ambient glow from sconces around the walls illuminating a gallery of fetish artwork. In each piece, a dominant lady, dressed in the sharp, severe lines of leather and latex, stood in various poses of domination over usually naked, supine men. The air was thick with the scent of expensive perfume and old leather. In the corner of the room, next to a large leather Chesterfield sofa, was an imposing mahogany desk. An older lady sat behind it, her gaze fixed on the glowing screen of a Mac. A Waterford crystal ashtray held a single, smoking cigarette, its curling smoke adding to the room's intoxicating atmosphere.

As Gary approached, the lady looked up from the screen and smiled. It wasn't a warm smile, but one of appraisal, of ownership. Gary was about to introduce himself when his phone buzzed in his pocket, the specific, insistent tone he had set for Annie. He glanced down at the message. "Do everything Miss Lizzy tells you to do, and if you're a good boy, this will be waiting for you." The message was followed by a picture that made his cock twitch instantly: Annie's hand holding open her wet and puffy pussy, a glistening invitation he was desperate to accept. He smiled, a foolish, hopeful grin.

"Eh, hem," the old lady interrupted him, her voice a low, throaty purr that cut through his thoughts. Gary jumped and apologized. "You must be Gary. Miss Annie has told me a lot about you." Gary was surprised he had been discussed with other people, but in his current state of obsessive devotion, he let it go. He assessed the older woman as she stood and walked from behind the desk. She was perhaps sixty-five, her long grey hair tied in an unruly bun that suggested barely contained wildness. She was surprisingly tall, maybe an inch shorter than Gary's six-foot-two. Her figure was formidable; large, heavy breasts threatened to push open the thin nylon housecoat she wore. Her arms were covered in a tapestry of tattoos, intricate coils of ink that disappeared down her impressive cleavage. She wore a little too much makeup, but it didn't detract from the raw, natural attractiveness she exuded.

"Let's get a look at you then," Miss Lizzy told him, her eyes sweeping over him. "Get those clothes off."

Gary was shocked, and a nervous smile played on his lips. "What?"

"Your clothes," she repeated, her voice losing its softness, taking on a sharp, commanding edge. "I need to get you all measured up for Miss Annie."

"What do you mean?"

"Take your clothes off. Very simple. Or do you need help? I can call Barry in; he'll be glad to help." The mention of "Barry" and the implied threat was enough. He remembered the text, "Do as Miss Lizzy tells him." He started to strip down to his underpants. "Them as well," she commanded.

Gary slowly slid his boxers down, his hands instinctively moving to cover his soft dick. Lizzy smiled to herself as she grabbed a cloth measuring tape and a notepad from the desk. She walked around him, her movements economical and precise, measuring every part of his body, from his neck circumference to his inseam. "Be a dear and move your hands," she said, her tone leaving no room for argument. "I need to get measurements there." He felt himself go red as he placed his hands beside his hips, exposing himself completely. She measured his balls, his soft length, and his girth. "Nice," she told him, taking notes. "No wonder Annie likes you." Then she said, "Can you get it hard for me, poppet?"

He hesitated, and Lizzy tutted dramatically. She moved forward, her hand closing around his flaccid cock. As she stroked him, she moved close, her lips brushing his, then her tongue slid between his open mouth. His cock twitched to life under her expert touch, the kiss a potent drug. She pulled away. "There, that's better." She quickly measured his erection, jotting down the numbers and writing "4C" beside them. She walked behind him and asked him to put his hands behind his back. Before he could process the request, her skilled hands snapped a pair of cold metal cuffs around his wrists, locking them together.

"What the fuck?" The slap was hard and fast, a sharp backhand that made his head ring. "Gary, there is no need for that kind of language," she scolded. Then she called out, "Barry!" The door opened, and a mountain of a man entered. "Take Gary here to the dressing room. Make him comfortable on one of the benches."

"Yes, Miss Lizzy," Barry said, his voice a deep rumble. He grabbed Gary's arm and the back of his neck, propelling him through another door and down a small, grey corridor to a room that looked like a medical bay. The walls were white-tiled, the surfaces gleaming stainless steel. Gary was pushed onto a leather bench and made to lie down with his arms still cuffed behind his back. Barry then strapped a thick, six-inch-wide leather strap around his chest, locking him in place. Next, he pulled out a pair of metal stirrups from the side of the bench and locked Gary's ankles in place, leaving him spread and exposed. The final indignity was a wide ball gag. Gary tried to fight, but Barry hit him hard in the stomach, knocking the wind out of him, and then shoved the gag in his mouth, securing it tightly behind his head.

Within the next ten minutes, Barry had shaved Gary's groin, his balls, and up to his mid-stomach, then between his arse cheeks, leaving him smooth and bare. Gary groaned as Barry took his now-hard cock in his mouth. Gary had never had any male-on-male inclinations, but the skill of the man was undeniable; it felt like one of the best blow jobs he had ever received. He arched up into Barry's mouth as much as his restraints would allow, feeling himself getting close, the pleasure overwhelming his senses. Then he heard Miss Lizzy's voice as she entered the room. "Stop, Barry. That's enough." Barry pulled off with a wet plop and smiled at Gary, a knowing, predatory grin.

"Well, Gary," Lizzy began, her voice echoing slightly in the tiled room. "Annie loves what you do together, how you've adapted. But she wants to broaden your horizons." She let him know that Annie was at home, probably with their pet between her legs, watching him through the camera in the corner of the room. Gary looked up and saw the blinking red light for the first time, a cold dread seeping into his arousal.

Lizzie started to release her hair from its bun, shaking it out so it fell in a grey cascade around her shoulders. Then she unbuttoned her housecoat, one button at a time, slowly. She smiled at Gary as she released her large breasts, the nipples hard and pointed, a dark, commanding brown. She picked up a bottle of oil and poured a little into her hands, moaning softly as she massaged it into her nipples. Then she opened her coat a little more, revealing a firm, tattooed stomach. She smiled as she slid the housecoat off her shoulders, and Gary's eyes widened in shock. There, jutting from her hips, was a substantial, erect penis. He panicked as he realized what was about to happen.

Lizzie poured the oil over her cock, making it glisten. She moved between his spread legs and pushed a couple of fingers deep into him, pumping them, stretching him. "Annie wants you to be more... versatile," she whispered, smiling. She then introduced him to her cock, pushing the head into his prepared arse. Tears ran down his face; he was confused, humiliated. Why would Annie want to do this to him? He grunted as Lizzie began to fuck him, her strokes long and deep, her hips slapping against his bare skin. He felt used, violated, a piece of meat in a scenario he hadn't agreed to, a pawn in a game whose rules he didn't understand.

When she was finished, Gary reappeared and handed her a wooden box with "C" stamped on the side. She slid the top off and pulled out a black metal object. His now-soft cock was unceremoniously placed inside a titanium cock cage, the cold metal clicking into place with no visible lock. He was eventually released from the bench, his body aching, his arse sore, his spirit crushed. He was given his clothes and instructions to tell Annie it would be a week. He had no idea what she meant. As he left, he got another text. "Good boy. Now thank Miss Lizzy, kiss her feet, and then come home for your treat. I'm horny and missing you."

That was all the motivation he needed. He fell to his knees, kissed Lizzie's feet, and thanked her, his voice a mumble of shame and desperate need.