Training Sessions - Part 1

"Have you been helped, sir?"

The question was posed by the cute blonde girl sitting behind the mahogany desk. She wore glasses and a white satin blouse buttoned all the way up to her neck. Her hair was pulled back into a ponytail and she exuded an impressive sense of confidence, as if she had total control over her domain. Charles wasn't entirely sure what that domain was - though he was certain he wasn't sitting in the waiting room of a traditional therapy practice - but there was no denying her confidence.

"Yes, I'm...I came with my friend...I don't really know why he invited me, to be honest, but I came with him and I told him I'd wait."

The cute blonde looked at the screen in front of her and studied it for a few moments. Charles found himself staring at her and looked away out of embarrassment.

"Ah, I see, you came in with Mr. Albert?"

It took Charles a moment to realize she was referring to Eric. He never referred to him as Mr. Albert, nor would Eric have referred to Charles as Mr. Simmons.

"Uh, yes, my friend Eric."

The young blonde's fingers moved swiftly over her keyboard. She clicked her mouse a few times and resumed typing. Charles assumed she was finished talking to him and reached into his pocket to pull out his phone.

"Oh, I'm sorry, sir, but no phones allowed. You may keep it in your pocket, but if you continue to take it out I'll have to insist that you leave it with me until Mr. Albert is finished with his session."

Normally Charles would have argued with such a silly rule, but instead he slipped his phone back into his pocket and rubbed his hands over his knees. The denim felt warm and the friction was a nice distraction from the increasing sense of annoyance he felt at Eric for making him waste part of his afternoon.

A door opened to Charles's right and he turned his head and stared in awe at a stunningly beautiful brunette in a pair of thigh high latex boots and a bodysuit made from leather on the bottom half and lace on the top half. The woman that had fetched Eric for his appointment had been dressed in boots, a latex skirt, and a red blouse, which made it seem at least plausible that she was an actual therapist of some kind. The woman now standing at the mahogany desk was certainly not a therapist. There was no chance. Her presence made it obvious that Eric had brought Charles into some sort of sex club.

"You don't stand a chance," the woman said.

She was looking over her shoulder at him. "What?" he asked.

"You're staring and I want you to know that you don't stand a chance. I'm way out of your league."

"What? I wasn't...I mean...I'm sorry for staring."

"You should be. It's rude to stare at a woman like that. We don't mind when a man glances, but staring like I'm a piece of meat is something else entirely."

Charles felt embarrassed. Deeply embarrassed, in fact, though he wasn't entirely sure why. "I'm so sorry. I really am. I didn't mean any offense and I don't think of you as a piece of meat."

She turned towards him and put her hands on her hips. She was slender and fairly short, and yet she was an imposing figure that inspired a touch of fear in Charles.

"I'm afraid that's not good enough."

"What?"

"Your apology. That's not good enough, Charles."

"How do you know my name?"

She stepped closer. "You need to do more than simply apologize to make up for staring at me like I'm a piece of meat for you to possess."

"I wasn't...I didn't do that...I'm sorry. I am. I'm sorry." Charles felt fear, though there was no obvious reason for it.

"You need to kiss my boots, Charles. You need to get on your knees and kiss the tips of my boots."

Charles noted the dark red polish on her fingernails. His gaze moved to her boots and he found them oddly appealing. Perhaps it was how shiny they were. Perhaps it was the tight fit.

"Do as you're told, Charles."

He found himself sliding off the chair and onto his knees. His hands fell to the dark red carpet in the waiting area and he leaned down and kissed both of her boots.

"Now lick them."

He sat back on his knees and asked, "What?"

She grabbed a tight fistful of his hair and anger flashed across her face. "You heard me, Charles. Now do as you're told or I'll be forced to punish you."

As soon as she released her grip on his hair, Charles fell forward and licked her boots. He noted his pounding heart and, more alarmingly, the stirring between his legs.

"Very good. Stay there with your head down."

She turned and walked back towards the desk where the cute blonde sat. Charles couldn't see much, though, as he dutifully kept his head down. He saw the boots and the nylon-clad legs of the blonde behind the desk.

The woman in the boots turned and walked towards him again. Charles's heart pounded harder. "Sit back on your knees."

He did as instructed and saw her holding a collar with a leash attached. She reached out and slipped the collar - which was leather with a fur lining inside - around his neck. It snapped shut and she gripped the leash in her hand.

"Follow me," she said. "On your hands and knees."

She walked away and Charles remained in place. She pulled hard on the leash and he fell forward and began to crawl after her. Her boots squeaked a little with every step as she opened the door she'd emerged from and held it open for Charles to crawl through.

"Enjoy your session, Mr. Simmons," the young blonde called out from behind the desk.

The door shut behind Charles and the woman in the boots led him into a small room with a dark red couch, a black leather bench, an impressively elegant-looking wooden chair with a leather back and cushion, red velvet curtains hanging from three walls, and strings of lights hanging from each of the room's four corners.

"What is this?" Charles asked as the woman in the boots shut and locked the door.

She stepped in front of him, pulled the leash tight, and said, "My name is Mistress Eden. You may call me Mistress or Mistress Eden."

Charles was dumbfounded and he said nothing as he stared up at her. She tugged hard on the leash and jerked his head to one side. "Yes, Mistress."

"Very good." She reached out and ran her fingers through his hair. Her touch was surprisingly gentle and Charles closed his eyes as a sense of calm washed over him.

"You have a very generous friend, Charles," Mistress Eden began as she relaxed the leash. "He's treated you to a month of sessions with me. Today is your first session. You'll be with me for an hour. You'll come back each week at the same time. After a month you can decide if you want to continue your transformation."

"My transformation?"

"I'm very good at what I do, Charles."

Mistress Eden offered nothing more, though, leaving Charles wholly confused about...well, about almost everything. He'd deduced that Mistress Eden was a dominatrix of some sort, but her intentions were unclear.

"What is it you do?"

"I reveal the truth."

She said it with such conviction that she must have believed it wholeheartedly, but Charles felt no closer to the answers he desired. He wasn't scared, though. Instead, he was something a lot closer to excited, which was why he hadn't yet gotten up, walked out of the room, and ended his friendship with Eric.

"Stand up and remove your clothes."

Charles froze and stared up at Mistress Eden. She wore a very serious look on her face and she clearly expected him to do as she'd instructed.

"There's no point in resisting your fate, Charles. Doing so will lead to unnecessary pain. You're mine for the next hour. That time can be spent learning about yourself or it can be spent suffering by my hand. It's your choice."

As if compelled by unseen forces, Charles stood and began removing his clothes. Mistress Eden flashed a brief smile and he felt a moment of joy at having pleased her.

Soon his clothes were in a heap on the floor. Charles instinctively held his hands over his crotch. It was cool in the room and his cock was soft and rather small at the moment.

"Put your hands at your sides," she instructed.

Charles did so without hesitation and again she flashed a smile. Again he felt joy.

Mistress Eden slowly circled Charles, holding tightly to the leash as she did so. She ran her fingers over his arm, his shoulders, his neck, and down his back. She squeezed both his ass cheeks. He'd never felt more like an animal, though he was not entirely put off by the sensation.

With the leash still firmly in her hand, Mistress Eden led Charles across the room and sat in the chair. She crossed her legs, looked at his cock, and said, "Masturbate."

He hesitated and she pulled hard enough on the leash that he had to bend over. She grabbed a handful of his hair, leaned forward, and said. "You will do as you're told when you're in my presence, Charles. You will come to understand that it's a privilege to be in my presence, that it's an honor to be issued an instruction, that it's your duty to do as I say when I say it. Now masturbate for me I will bend you over and spank your ass until it's black and blue."

She loosened the leash and Charles began to masturbate. He felt deeply uncomfortable at first, but the tugging on his cock produced just enough arousal to wash away that discomfort. Soon he started to grow, his flaccid flesh transforming into something resembling an erection.

"Stop."

Charles released his cock and let his hand fall to his side.

"When was the last time you had sex, Charles?"

"It's been almost six months."

"And when you fucked this woman, did you make her cum?"

"I think so."

Mistress Eden laughed. "If you think you made her cum, you probably didn't."

He was embarrassed. He hadn't made her cum. He knew he hadn't made her cum. He'd been a little drunk that night and had struggled to stay hard. The girl - whose name he'd forgotten - failed to hide her frustration at his inability to keep his erection as stiff as she wanted it. The whole night had been something of a disaster, though that was hardly an isolated experience for Charles.

"I didn't," he said. "I don't know why I said I thought I had. I know I didn't make her cum."

Mistress Eden slapped his dick hard enough that Charles groaned and doubled over in pain. She yanked on the leash and he fell forward, nearly slamming his forehead into the arm of her chair before finding his balance. He ended up on his knees and thought better of trying to stand. Instead, Charles sat back and looked up at Mistress Eden.

"I don't like being lied to, Charles."

"I'm sorry. I shouldn't have lied."

Mistress Eden stared at Charles for an uncomfortably long time. He held her gaze, though. He wasn't sure if it was a test or if he was supposed to say something, but he remained quiet on his knees.

"Do you know what we do here?"

"Domination," Charles answered. "Like, paid domination sessions?"

Mistress Eden stood and moved behind him with her hand still tightly gripping the leash. He felt the latex of her boots press into his back and the heat of her thighs against his shoulders.

"I'm a trainer, Charles. I suppose you could call me a therapist as well, but I like to think of myself as a trainer."

Her fingers moved through his hair and she took a tight grip.

"I help turn men like you into useful members of society," she continued. "Men that are lost and struggling. Men that cannot seem to make a relationship with a woman work. Men that are just a few bad breaks away from turning into angry, misogynistic losers who spend all their free time complaining about how women are the source of all their problems in life."

Mistress Eden released her grip on his hair and moved in front of Charles once more. She stepped close enough that he had to crane his neck to look up at her.

"Every man wants to be an alpha male type. They want to be irresistible to women. They want to climb the corporate ladder with ease. They want to command big salaries, drive fast cars, and fuck whoever they desire."

Charles was willing to admit that all of those things sounded good, though he was equally aware that he'd never found it easy to achieve any of those things.

"Not all men are built that way, though," she continued while running her fingers over his lips. Charles found it oddly compelling to be touched in that way. "You're not built that way, Charles. Trying to be that kind of man is a struggle for you. A difficult, frustrating struggle. You don't have to struggle, though. There's a place for a man like you, for a man like your friend Eric. My job is to show you your place and then help you accept that it is, in fact, where you belong."

Two of her fingers moved between his lips and onto his tongue. They probed deep enough that Charles felt his gag reflex threaten to trigger. He saw a smile creep across Mistress Eden's face and experienced a surprising rush of satisfaction at having played some part in creating that smile.

"Your place is beneath a strong woman, Charles. Your place is to be led by her. Your place is to put her desires far above your own. In fact, your eventual place is to forget about your desires entirely and to focus all of your energy on making her happy. You are destined to lead a life where you embrace the reality that you are inferior to the woman you've sworn yourself to, where she is a goddess that you are privileged to worship. That is the life I will train you to lead, and when you're ready you'll be paired with a woman that is worthy of your devotion."

Her fingers left his mouth and she wiped the saliva on her thigh. Mistress Eden stepped back, pointed to the streak of wetness on her soft skin, and said, "Clean it."

Charles leaned forward and licked his fluid from her skin. It felt so good to press his lips against her thigh, to kiss her as he cleaned up his saliva while her fingers ran through his hair. It was such a simple act, and yet he felt a surprising sense of joy along with a healthy dose of arousal that had returned his cock to an erect state. Though he felt some resistance to how she'd described him and his destiny, Charles couldn't help but wonder if there was something to her assertions, at least based on how good he felt in that moment.

Mistress Eden released her grip on the leash, stepped away from Charles, and left the room. When she returned the young blonde from the front desk was with her.

"Charles, you've already met Lydia. Now you're going to get to know her in a far more intimate fashion."

Lydia began to unbutton her blouse and Charles turned away.

"You can look, Charles," Mistress Eden said.

He turned back, though it still felt awkward. Lydia was remarkably beautiful and her body was breathtaking. Charles's cock throbbed, though not because he thought there was a chance he'd be having sex with Lydia.

Once she was naked, the young blonde walked past him and sat in the wooden chair. She spread her legs as Charles looked up at Mistress Eden.

"Eat her pussy, Charles," she instructed.

He spun around and crawled towards the beautiful blonde. She reached down to grab his leash and pulled it tight, urging him between her legs at a greater pace than he was moving.

Mistress Eden's hand found the back of his head and applied pressure. Charles extended his tongue and licked the clit of the fabulously beautiful young woman in front of him.

For what felt like an impossibly long time, the only sound in the room was Charles’s tongue moving over the pussy he was tending to. He licked at a steady rhythm but not one moan came from Lydia's lips. Charles was suddenly awash in a sense of insecurity. Was he doing a bad job?

"That's enough, Charles," Mistress Eden said. "How was he?"

"His technique needs work. He uses the tip of his tongue far too often and he changes rhythm more frequently than he should. Most of the time he's going too quickly. That's not always unwelcome, of course, but a rapid speed should be used sparingly when a man is worshiping pussy."

Charles felt breath on the back of his neck before he realized Mistress Eden had knelt behind him.

"A man like you must always worship when he's lucky enough to be granted the pleasure of being between a woman's legs, Charles," she said. "I'm sure you've largely thought of eating pussy as a means to an end or a task to get through as quickly as possible. I'm afraid you're not the kind of man that can afford to behave in that manner, though. No man should behave that way, but some have enough to offer that a woman doesn't mind. You don't have enough to offer, Charles. You are not a superior version of manhood. Now, worship her pussy."

Charles leaned forward as he considered the notes he'd been given. Mistress Eden was right. He did think of eating pussy as a means to an end - getting a girl turned on so they could have sex - or as a task to be accomplished, usually when he'd had an orgasm and she hadn't and so he felt she'd be unlikely to give him an orgasm again if he didn't return the favor.

Gripped by a desire to do a good job, Charles pressed his lips against Lydia's pussy and extended his tongue. He dipped it as deep inside her as he could and then slowly dragged it up towards her clit. He licked slowly, using the tip of his tongue at first but massaging her with the thick part, too. Charles looked up at Lydia as he worshiped her pussy and was pleased to find a smile on her face.

"That's much better," she said.

Mistress Eden ran a hand down Charles's back and gripped his ass. That hand then moved between his legs to cup his balls and she teased them, eliciting a moan.

"Don't think about what she's doing," Lydia said. "Focus on me. Focus on my pleasure. On my clit. On the task of worshiping the superior woman that has granted you the intense joy of tasting her cunt."

Charles moaned, this time at Lydia's words. She rewarded him with yet another smile and then put a hand on the back of his head, closed her eyes, and moaned.

The sound was so beautiful. It struck Charles as real and it was thrilling. He'd made this beautiful woman feel good. He'd made her moan because she felt good.

"Keep working her pussy, Charles," Mistress Eden said softly. "You must get used to being on your knees in front of a superior woman for as long as it takes to satisfy her. You must get used to satisfying her without any thought of your own pleasure. That part will be quite difficult for you - it's difficult for all men - but over time you'll get better at it."

That's when she started stroking his cock. Despite the intensity of the pleasure he felt, Charles knew he was being tested. He knew she was trying to distract him from the task at hand. It worked. He was suddenly overcome with a desire to have an orgasm. He wanted to fuck Lydia. He wanted to masturbate. He wanted Mistress Eden to jerk him off. He wanted to cum in whatever way he could.

"Concentrate, Charles," Lydia said. "Focus on my cunt. Focus on the joy of being permitted to worship me. Don't abandon your technique. Don't think of trying to make me cum so you can get on with your orgasm. You won't be having an orgasm."

Despite his best efforts, Charles struggled to maintain the technique he'd tried on Lydia. His tongue moved faster. He moaned repeatedly. At one point his hand moved - seemingly without his input - between his legs to grasp his cock. Mistress Eden grabbed it and pinned it behind his back - painfully so, in fact - as she admonished him, but she kept stroking his dick.

"That's enough," Lydia said.

Charles sat back and looked up at her. She was angry, or perhaps annoyed. She wasn't happy, though.

"You failed," she said. "Failure is inevitable, though. Training a man is a long, difficult process that will be filled with failures."

Mistress Eden stood and left the room. Charles looked over his shoulder and Lydia jerked the leash, pulling his attention back to her.

"It's going to feel like you're being punished," she said. "And I suppose you are, in a way. However, what's about to happen will also be quite pleasurable for Mistress Eden and me. I will certainly cum. She might choose to cum. You will not enjoy yourself, but you're not supposed to. Sometimes, serving a superior woman means suffering for her pleasure. It often means doing something that isn't entirely pleasurable for you simply because it's what she wants. When your training is complete you will find yourself eager to engage in such acts, but today it will feel like pure suffering."

The door opened and Charles resisted the urge to look over his shoulder. Lydia stood and led him towards the leather bench. She directed him to lie face down on it. Charles did as he was told. Lydia slipped a cuff of some kind onto each of his wrists, effectively binding him to the bench.

Lydia released the leash and returned to the chair. She spread her legs and began to masturbate while she looked at Mistress Eden.

Charles finally surrendered to his curiosity and looked over his shoulder. He saw Mistress Eden stroking a black strapon cock. It was slick with lubrication of some kind and she looked deeply intimidating.

Mistress Eden approached the bench and moved behind Charles. She reached down and rubbed her lubed fingers over his asshole. Then she moved closer and the head of her strapon parted his ass cheeks and rubbed back and forth over his hole.

"I don't want this," he said.

Mistress Eden laid her body on top of his as the strapon began to penetrate him. Charles groaned from the pain, though it was far less than he'd expected.

"I know you don't," she said in a soft commanding, tone. "What you want doesn't matter right now. That's going to become a running theme in your life, Charles, and you need to get used to it. A man like you doesn't always get to do what he wants. A man like you must make sacrifices for the happiness of the goddess he gets to worship. Fucking a man's ass turns me on. It makes me wet, Charles. Making you submit to anal penetration drives me fucking wild with desire. Lydia enjoys watching when I fuck a man in the ass, which means you're going to satisfy two women. I'll bet you've never satisfied two women at the same time, Charles."

It was true. Charles even considered saying so, but Mistress Eden plunged every inch of her strapon into him and literally took his breath away.

Getting fucked was, in fact, less painful than Charles had imagined. It was uncomfortable, though. Having his bowels filled seemed to trick his body into thinking they needed to be emptied and the thrusting in and out played that trick on his brain over and over and over again.

There was also the humiliation of the whole thing. He was bound to a leather bench - one that was clearly used for this very purpose - and getting fucked in the ass by a woman he'd only just met as another woman masturbated to the sight of his anal virginity being taken.

It was a few minutes into the ass fucking that Charles had a significant realization. He wasn't being fucked against his will. He hadn't been collared and leashed against his will. He could have left at any time. In that very moment he could have said he wanted the anal sex to stop, that he wanted to be released. They would have let him go. They weren't his jailers.

Charles never considered asking to leave, though. Not once. Some part of him was enjoying the training session. Some part of him probably felt as though Mistress Eden and Lydia were right about him, that he was the kind of man that should surrender himself to the service of a superior woman. Some part of him probably loved the idea of being trained to be a good partner for a superior woman and then being placed with that woman.

That's when Charles started to moan. The anal sex didn't feel any better, but something about the whole situation had changed. Something about it felt better. Much better.

Lydia was masturbating quite furiously. Mistress Eden was grunting and groaning and moaning like she was actually getting off on fucking him. Charles felt no pleasure, but he was suddenly quite turned on.

"Fuck...I'm cumming!" Lydia cried out.

Charles watched her have an orgasm and a sense of genuine happiness washed over him. He'd never felt it before. Not to that degree. It was incredible.

Mistress Eden fucked him harder. Hard enough that it hurt. He couldn't keep quiet. The pain was immense.

Then she came. She buried her strapon inside him and he felt her body tremble on top of his. She'd cum while fucking him. Charles didn't understand how it was possible, but he felt that same sense of happiness.

Mistress Eden pulled out and Lydia stood to release Charles from the cuffs. He remained face down on the bench. He was breathing far harder and heavier than he'd noticed. His asshole hurt and yet he felt a strange sense of satisfaction.

Lydia stood and got dressed. She thanked Mistress Eden and left the room.

"Your first session is over," Mistress Eden said. "You may get dressed. You'll find a bathroom down the hall to the right if you need to get cleaned up."

"Thank you, Mistress."

She smiled. "You have a great deal of potential, Charles, and I've done this long enough to know that if you continue the training you'll come out on the other side a far happier man than you ever thought possible."

She removed the collar from his neck, bent over, and kissed him softly on the cheek.

"I'll see you next week," he said as she turned to leave.

Mistress Eden said nothing, but Charles thought he saw her smile.

It was all very confusing - a lot had happened in the short span of time his session covered - but Charles felt light and oddly happy in that moment and that was more than enough to convince him that coming back for another week was the right choice.