Lucy was what many men refer to as a ‘cougar’ – a bit on the older side, but with the body of a twenty something and a sexual appetite to match. She had gained confidence in her years, and if she saw something (or someone) she wanted, she went after it. She didn’t mind the guys who played hard to get, but she much preferred those that fell to their knees, begging her to give them the time of day. Lucy was a different brand of cougar – she was a dominatrix with a thing for younger submissive men. She didn’t want a boy toy, she wanted a slave.

She had many of them in her years, ones that come to her as untrained puppies who think they are in for a bit of kink, and leave her well disciplined men that any woman would be lucky to have. The ironic thing was, as she grew older in years, the men who came to her for training seemed to get younger and younger. She’s even had to turn away a few over-eager seventeen year olds in her day, telling them to return when they’re of consenting age.

Recently, she had found herself without any submissives to play with. Her latest ‘boy’ had left her care after months of training, and she was now on the market to take in a new trainee. She had a number of men to choose from, as she had a waiting list that read like a phone book. She decided that she would pick her top three, and have a mini-session with each of them, to determine who was worthy of her tutelage. There was Mark, a 22 year old recent college grad who was trying to make his name on the banking scene, Tyson, a 19 year old college freshmen football player, and Brian, a 27 year old truck driver. Each had requested to come under Lucy’s care, and each patiently waited for her next opening. Lucy sent an email to all three to schedule a weekend where they would come to her home and prove themselves as a submissive that she would be willing to spend her time training.

….

Lucy had arranged to have a car service pick up Mark from the train station and bring him to her home in the countryside. When it pulled up, she watched from the window as the smartly dressed man take his duffel bag out of the trunk of the vehicle and tip the driver. As the car pulled off, Mark made his way up the cobble stone walkway and knocked on Lucy’s door. She closed the curtain behind her, and slowly made her way to her front door to greet her new arrival.

“Miss Lucy?” questioned the young man as Lucy opened the door.

“Yes, boy. Glad to see you have made it. Please, come in.”

Lucy’s home didn’t give away her fetish. Her kinky toys and bondage devices were all locked up in rooms that were not easily accessible to the general guest who enters her home. She directed Mark to have a seat, so they could have a brief chat before their weekend began. It was business right from the get-go.

“The rule are quite simple, Mark. You don’t do anything without asking for permission. You don’t eat, you don’t sleep, you don’t shit and you don’t cum. You lost all of your free will when you entered that door. Speak when spoken to and always remember that it is you that are indebted to me for this training. You have your own room for the weekend. Don’t worry, it’s not one of these stripped back closets with a mattress on the floor. You’ll need quality sleep to keep up with your training – that is if I let you go to sleep. You will address me as Mistress. Do you have any questions?”

“No, Mistress.”

“Good, let’s get going, then, shall we?”

Mark went through the routine that all incoming submissives into Lucy’s home performed – hot steaming shower where they were completely shaved from neck to toes, followed by an overall examination by Lucy. She cleaned out his body with an enema, since much of her training involved anal play. Lucy checked to see the size and shape of the trainee’s penis (both erect and flaccid), how tight their anus was, the length of their tongues, as well as their overall physique. She has seen pictures of Mark naked before – it was part of the application process – but in the flesh it’s so much different. Mark stood obediently, with goose bumps showing on his skin, more from the anticipation than the temperature. He flinched slightly as she probed his bottom with a long and lean vibrator, but his cock showed a different reaction.

“Never had anal, have you boy?”

“No, Mistress.”

“That will take up a significant amount of training then. I’d prefer it if you had a bit of experience, but at the end of the day, I suppose it’s that much more for me to enjoy teaching you.”

“Yes, Mistress.”

“Right then. Your room is right across the way. Wait for me in there while I set up my office. First, let me get this on you.”

Lucy pulled out a cock cage for Mark to wear. It resembled a codpiece that you see on suits of armor, but more a framework than full coverage. It opened at the side to slip over Mark’s dick and balls, and locked shut with a small padlock which Lucy kept the key for. It was attached to a harness that went around Mark’s hips and between his legs, which was kept belted into place with the help of a second padlock. Lucy opened the door to Mark’s room, and told him to wait for her to call him.

While Mark waited with baited breath in his guest room, Lucy prepared the space which she referred to as her office. She unlocked the door, walked into the room that took up nearly half her home, and opened the curtains while she readied for the evening. She uncovered a device that was pushed up against the wall – a set of four stairs, build out of a single large cube of wood so that they were freestanding. On each step were metal pipes that came up and out from the wood so that arms and legs could be easily trapped to restrict movement. She turned to the king size bed and made sure that the restraints that came up from under the bed were still held fast to the frame. Lucy then made her way over to the sex swing that was hanging from a doorway and readied that for its nightly use. Lastly she looked over her collection of anal plugs, vibrators, ball gags, clamps and clips that had been freshly cleaned and sterilized that morning. Everything was perfect and in its place.

She called Mark to her room, and directed him to the bed. Under her instruction, Mark stood at the edge, facing inward. He bent at his hips so that the top half of his body was laying on the bed, while his bottom half was still standing. Lucy attached his wrists to one set of restraints that connected to the opposite side of the bed, and his ankles to a set that were affixed to the floor. She unlocked the back of the chastity belt that Mark was wearing, so that there was nothing in between his ass and the free air. Lucy took out a vibrator that was especially made for those who were taking part in their first ass fucking – long, lean, slightly curved with a good strong motor. She rubbed at bit of lube on the tip, and teased Mark’s exposed rim with its cool plastic vibrations. She could just go full force and ram a fat butt plug up his ass, but she was planning on saving the anal torture for a little bit later in the evening. She slowly slipped the vibe into Mark’s ass as he let out a groan. She could see his body tighten around the probe, and she started to rhythmically pull it out and push it back into his virgin ass.

Mark’s cock hardened, and she could see it pushing up against the top of the cock cage. A drip of pre-cum had started to fall from his tip, and the thought to herself that she would make him clean that up later. Mark started to squirm with each thrust of Lucy’s hand, so she grabbed hold of her favorite riding crop and gave him a few quick smacks on the ass, admiring her criss-cross patters on his bare cheeks. Mark whimpered, but relaxed more as Lucy continued her anal fucking.

“Good boy”, Lucy complimented as she stroked his curly haired head.

She turned and looked over at her toy collection, debating in her mind where to go next. She had the option of now inserting a training butt plug and flipping Mark over so that she could get to work on his cock, or she could continue with the ass fucking, but slipping into a strap on rather than this skinny little vibrator. She decided on the former, and slipped the vibe out of Mark’s ass. She watched his body relax once again, relieved to have his bottom no longer occupied.

“Don’t get too comfortable, boy”, she directed.

Lucy took hold of the small red anal plug, and touched the red rim of Mark’s hole with it’s cool tip. With one quick motion, she pushed it in to its hilt, causing Mark to scream aloud in pain.

“What did I tell you about the rules? Did I give you permission to scream?” questioned Lucy.

She knew that this was the reaction she would get, so she wasn’t all too disappointed in Mark’s disobedience, but she loved to keep them on their toes. Mark’s ass was now filled to the brim with cool red latex, which was being held firmly in place with the tightness of his asshole.

She untied Mark’s arms and legs, and watched as he tried to stand at attention while having a butt plug up his ass. Lucy almost laughed to herself at the awkward positions that Mark tried to get himself in as to not put too much pressure on his bottom, but in the end she told him to sit on the black stool that she placed near her bed. Mark flinched as the butt plug went deeper into his ass, but soon settled after finding a somewhat comfortable position.

Lucy located her Hitachi vibrator and plugged it into the wall socket nearby. She planned on ending this session rather quickly so they could move onto other things later in the evening, and she knew that this vibe was the way to go. She ordered Mark to scoot forward so that his cock and balls were hanging off the edge of the stool, but his ass was still firmly filled with the plug. He struggled slightly, to which he was punished with a few smacks to his cock cage. The pain only turned him on that much more, and his firmness pushed against the tip of the chastity belt. Lucy took out her keys and unlocked the belt, leaving his stiff dick free to grow as large as it could.

She turned on the vibe, and it’s loud hum filled the room. Lucy took her hand and started stroking Mark’s cock in rhythm. He leaned back on the chair and moaned in pleasure. She placed the head of the vibrator underneath Mark’s balls, with his reaction being one of immediate stiffening. She knew it would be quick now, but she wanted to tease him a bit.

“You can’t cum without permission, Mark.”

“Yes, Ma’am” replied the slave-to-be.

Lucy knelt down and tongued a trail up and down Mark’s purple cock, moving back and forth slightly from the vibrator. She saw it twitching, and took her wet mouth away to give him a bit of space to relax. Soon she was back to his manhood again, this time teasing the tip with her warm lips. She could taste the saltiness of the pre-cum, and she lapped it up with one quick lick. Mark grunted and begged Lucy to let him cum.

“Not yet, boy.”

She moved in closer to him, and lifted her skirt, exposing her shaved pussy. She turned off the vibrator and set it on the floor. She then rubbed the lips of her mound against his hard cock, and Mark shuffled his body as to not cum right then and there.

“Keep still, boy.”

Lucy pressed her pussy up against Mark’s cock, took his dick in her hands, and started rubbing it against her swollen clit. She felt the rush of blood to her pussy, and started using that pre-cum as a lube for her own sexual desires. She moaned along with Mark as she turned his cock into her own personal pleasure tool. Her hand movements were getting Mark harder and harder, and his throbbing started to occur on a regular basis.

“I cum first. When I’m done, you can have yours” Lucy gruffly spoke while she was getting herself off with Mark’s dick.

She spread her legs slight as to get more contact between her ready clit and Mark’s cock. She pulled her own nipples through her shirt, and soon she was cumming. As she worked through her orgasm, her hand sped up movement to give herself as much of a ride as possible. With each tug, Mark steadied himself, waiting for her to finish before he exploded. Lucy screamed as she was brought higher and higher into a state of ecstatic sensation, and slowly began to come down off her high. When he breathing slowed and her screams subsided, she told Mark he could now release.

Mark didn’t wait much longer after those words before he let down his guard and sprayed Lucy’s pussy with a river of cum. He grunted and groaned through the whole process, and shuttered so much that Lucy had feared that he would fall off the stool. He rocked against the butt plug as he came, each time a squirt of cum followed through. Again, as his breath slowed, Lucy knew that he was finishing, but the night was only to start.

She looked down at herself, then again at an exhausted Mark, and knew that there was a long night ahead of them.