Training Sessions - Part 2

Click here to read the first part of the story.

---

The woman sitting on the far side of the cafe looked familiar to Charles, though he couldn't quite place her. He looked her way half a dozen times, each time wanting to stare until his mind conjured who she was, though each time he did no more than glance so as not to draw her attention.

Her name never materialized, nor did his association with her, so Charles picked up his coffee and croissant and found a table looking out the window. He pulled out his phone and mindlessly browsed TikTok as he nourished himself with a buttery croissant made with obvious love and skill.

"I saw you staring."

Charles's head whipped towards the voice and he saw the woman from other side of the cafe. In an instant he recognized her. It was Mistress Eden, though she looked nothing like the woman that had subjected him to an hourlong session of domination that had included the first - and so far only - anal penetration of Charles's life.

"Uh...um...hi...how are you?"

She smiled so sweetly that Charles felt every bit of nervousness wash away. A moment later she was sitting next to him. She wore jeans and a white turtleneck with a pair of simple black flats. Charles was surprised by her attire, but he shouldn't have been. No one walked the world dressed in latex and leather. Those were her work clothes and it would be absurd for her to wear them to get a coffee.

"The baked goods here are divine, aren't they?" she asked.

Charles was still stunned - and his mind still conjuring images from his experience with Mistress Eden - so he struggled to say much of anything.

She seemed to recognize his discomfort and put a hand on his arm. "It's okay, Charles." She leaned in and, in a much softer tone, said, "I'm not going to bend you over the table and fuck your ass. That sort of fun is only for your training sessions. I'm a perfectly normal woman out here in the real world."

She reached for his croissant and tore off a small piece. It ended up in her mouth a moment later and her eyes fluttered as she chewed and let out a soft moan that conjured a memory of her having an orgasm while fucking his ass with a sizable strapon.

"Will you be attending your next session?" she asked.

"Yes."

"Good. You have such potential and I'd hate to see you squander it because you fear what might happen if you dive into the depths of your true self." Then she leaned in again and asked, "Has your ass recovered from the fucking I gave you, Charles?"

Her breath caressed his neck and raised goose bumps on the exposed skin of his forearm. Mistress Eden ran her fingers over the skin and leaned in a little more. For just a moment he felt her lips against his neck and Charles sprouted an erection.

"It hurt for a few days," he admitted. "But it's fine now."

"It won't be fine after your next session."

He closed his eyes and for a moment it was like she was inside him again, like her strapon was savaging his asshole while he watched Lydia masturbate to an orgasm at the sight of his anal humiliation.

She sat back, crossed her legs, and asked, "Do you have a girlfriend?"

"No."

Mistress Eden tore off another small piece of his croissant and popped it into her mouth as she studied him. "Are you dating, or have you given up on finding someone?"

"It's been a while since I've been on a date. A few months."

"You'll need to start dating if you want your training to have any effect. It works a great deal better if you put it into practice right away instead of waiting until you've finished your sessions."

Charles turned to Mistress Eden and, in a moment of unexpected bravery, asked, "Can I take you on a date?"

She smiled. "You're sweet, but no, I don't date clients. Plus, I think we both know I can do better than you, Charles."

Though he knew it was true, her comment was remarkably painful.

"I'd guess that you're underemployed," she noted. "You don't dress particularly well. You're not in anywhere near as good a shape as you could be. I require a submissive boyfriend, of course, but I prefer a submissive man that exudes the qualities of what people refer to as an alpha male. Really, though, it's just a man who works hard on himself, who works hard at his job, and who is exceedingly desirable as a result. It's far more exciting - enthralling, even - to dominate a man like that, Charles, and you have a great deal of work to do if you want to be a man like that."

With that, Mistress Eden stood and walked out of the cafe. In her wake, Charles felt aroused, insulted, and introspective. A quick internal survey indicated that she was, unfortunately, spot on in her criticisms, in particular the part about him being underemployed. He'd graduated from a good business school. One that would have landed him a six figure job. He hadn't looked especially hard for work, though, and had settled on a position in middle management at a declining company that handled ticket sales and accounting for small concert venues, amusement parks and county fairs around the country.

Charles wondered - foolishly, in all likelihood - if Mistress Eden would, in fact, go on a date with him if he corrected all the things she'd mentioned and was no longer a client. He shook his head to push away the possibility, for he understood that even considering it was a way of avoiding going on dates with other women, which wasn't something Charles was especially eager to do.

He downloaded Hinge, though. He didn't want to walk into his next training session and disappoint Mistress Eden by saying that he hadn't gone on a date. Charles suspected that she'd be unhappy with that, and that her being unhappy might mean something unpleasant for him.

---

Mistress Eden wore a fishnet body stocking, strappy black heels, a pair of black latex shorts, and a black latex bra. She had on a pair of latex gloves, too, and her fingers probed Charles's mouth as he sat naked on his knees with his hands clasped behind his back.

"When you submit, your body is no longer yours," Mistress Eden said. "It belongs to whomever you submit to. Right now, it belongs to me. I am free to invade your body as I desire. I am free to use your body however I desire. I am free to offer you pleasure or make you suffer. I am free to fuck your mouth with my fingers. I am free to make you choke on my fingers if I desire it."

Charles hoped she wouldn't make him choke, though he wouldn't fight it if she did, at least not intentionally. He wanted to submit. It felt good to do so within the safe confines of her room, which was the same as last week. The lighting had changed, though. This time the room was bathed in a hue of light blue, which he thought worked quite well with the black latex that adorned his mistress.

"Suck them clean as I pull them from your mouth," she said.

Charles closed his lips around her latex-clad fingers and sucked hard as she pulled them from his mouth. They weren't dry, of course, but as they emerged from the tight grasp of his lips they were largely free of saliva.

"You know, that technique tends to make a man very happy," Mistress Eden said. "Suck hard as you pull back. Swirl your tongue around the tip and stroke him with your hand and you've got a recipe for making a man cum in your mouth."

Charles was surprised that Mistress Eden ever gave blowjobs and his face must have shown it.

"Does it surprise you to hear that I pleasure men with my mouth?"

He nodded.

"Why is that, Charles?"

"I...I guess I figured that a dominant woman doesn't give blowjobs. It feels like...it feels like a submissive thing."

"It can be. It often is, in fact, though it's far from an absolute that a blowjob is an act of submission. It can be an act of dominance. It can also be part of an equal exchange of pleasure between partners." She bent over and smiled. "Though I'm not always dominant, Charles. Sometimes it feels good to switch, to play the part of a submissive with a worthy man."

She stood and walked behind him. Her fingers entwined in his hair and she pulled hard enough for Charles to wince.

"Could you suck cock, Charles?" she asked.

"No. Not a real cock, at least."

"A real cock?"

"One attached to a man. I couldn't suck that kind of cock. I could...I could suck a strapon."

She laughed. "I should hope so. You've already taken one up the ass. It's far less humiliating to take it in your mouth." She ran her hands over his shoulders and down his arms, bending over enough to kiss his neck. "And what about a cock attached to a beautiful trans woman?"

"I...I don't know," he admitted, preferring honesty over an outright refusal based in a fear of cock. "I've never...I don't think I've ever met a trans woman."

"Stand."

Charles stood and clasped his hands behind his back once more. Mistress Eden smacked his ass a handful of times, delivering painful blows to each cheek, presumably for no other reason than to prove that she could. His body was no longer his, after all. It was hers to do with as she pleased while he offered his submission.

Then, in an instant, her fingers were in his ass. Charles winced and very nearly stepped away before catching himself.

"Very good," she said while penetrating him repeatedly. "Your body is mine once you submit to me. Your mind will be mine, too, but that's harder to adjust to. Don't worry, though. You'll be a good submissive soon enough."

Mistress Eden pulled her gloved fingers free, cleaned them with an anti-bacterial wipe, and turned to Charles as she leaned against the wooden table that held various training implements.

"Have you been on a date?" she asked.

Charles nodded. "Two, actually. Neither was very successful, but I took to heart what you said at the cafe and downloaded Hinge."

"What made your dates unsuccessful?"

"Well, I know it's a little shallow, but the first girl didn't look anything like in her pictures and there was something off-putting about that to me."

Mistress Eden smiled. "I believe your instincts are guiding you well in that case. If someone posts misleading pictures they're likely willing to be dishonest in all manner of ways and there's little point in building a relationship with a dishonest person."

"The other girl was nice, but there was no chemistry at all. She seemed a little...I don't know, delusional about life?" Charles took a deep breath. "No, that's way too harsh. I'm sorry. I just mean that...well, when I asked what she did for a living she told me she was a poet. Then I asked her how she made money as a poet and she got angry for a second and then said that life isn't all about making money. I told her I agreed but that money was necessary to live life. Then she got mad again and then finally she told me that her parents pay most of her bills - she was probably 30, by the way - and that she was trying her best to make a living as a poet. So, that was weird, and that was on top of the lack of spark or chemistry or whatever you want to call it."

Mistress Eden pushed away from the table and sauntered towards Charles in a manner that made his cock stir to life. He instinctually reached to cover his genitals before catching himself and clasping his hands behind his back once more.

Moments after stopping in front of him, Mistress Eden reached out and took his cock in her gloved hand. The latex was warm and surprisingly soft as she stroked him slowly. Charles grew in her hand until his cock was swollen with desire. He felt it in the rest of his body, too, and the smile on Mistress Eden's face filled him with what he knew was misplaced hope.

"And when a date asks what you do for a living, what do you tell them, Charles?"

He looked away. "I say I'm in management. I try...I try not to talk about it."

Mistress Eden directed his gaze to her face, stared for a few seconds, and said, "Because you know that accurately describing your job will turn off most women?"

It wasn't exactly how Charles would have described his approach to talking about his job, but it wasn't wrong, either. "Yes."

She wrapped her fingers around his cock and squeezed. She kept squeezing, to the point that Charles began to panic that she might injure him.

"Have you applied for a new job?"

"What? No. You didn't tell me to do that."

She squeezed his cock harder and Charles felt his knees buckle. His entire body was awash in panic. Adrenaline flooded his system and just as he reached for her hands, Mistress Eden released him from her grasp.

"I am not your girlfriend, Charles. I am training you to be a better man, but much like physical therapy, if you don't do the work at home you'll never get better," she said. "Now, lie face down on the bench."

Charles turned towards the leather bound bench. His heart rate increased as he thought of the painful strapon fucking he'd taken on that bench the week prior. There was no point in resisting, of course, so he approached the bench and laid on his stomach. The cuffs were soon affixed to his hands and ankles, binding him in place for whatever Mistress Eden had planned.

"You need to be punished," she said. "You need to suffer. In part because it pleases me to punish a man and in part because I want you to remember this punishment - and feel this pain - when you consider being lazy in the coming week. I want you to feel this pain when you pass on applying for a new job in favor of masturbating to porn. I want you to feel this pain when you fail to put in the effort to connect with the girl you take on a date this week. I want you to feel this pain whenever you even consider being less than the best version of yourself this week."

Mistress Eden chose a device with a black plastic handle and a few dozen long, thin leather straps attached to it. Charles had never seen anything like it before, but he understood its purpose and remarkable effectiveness from the moment she brought it down on his ass and thighs. The leather straps spread as they moved through the air and struck a wide swath of his skin, delivering far more widespread pain than her hand could.

Charles was trembling by the time the punishment was over. He'd nearly cried from the unrelenting pain. In the immediate aftermath he felt absolutely certain that he wouldn't forget the pain, that he would absolutely remember it each time he found himself surrendering to his desire to be less than the best version of himself that week.

Mistress Eden uncuffed Charles and helped him stand. Then, to his complete surprise, she pulled him into her arms for a long, tight hug. Her body was warm and the material of her fishnet body stocking felt rough-but-reassuring against his skin. She held one hand on his lower back and the other on the back of his head. He felt secure and safe and comforted and he found himself wishing the hug would never end.

It did, of course. She stepped back and Charles was surprised when she reached up and wiped a tear from his cheek. He hadn't even felt it escape the corner of his eye.

"I'd like to cum now, Charles," she said. "I could masturbate while I make you fuck yourself with a toy, but you deserve something better after enduring that punishment, so I'm going to let you worship my pussy."

She unzipped her latex shorts and pulled them down. Her pussy lips were plump and wet-looking through the wide fishnets and she took his hand and led him towards the wooden chair with leather cushioning. Mistress Eden sat in the chair, inched her hips forward, and motioned for Charles to get on his knees.

He did so and she said, "You may worship my pussy until I cum."

Charles dropped to his knees, crawled forward, and tended to the throbbing clit of the beautiful woman sitting in front of him. It was slightly more challenging with the fishnets getting in the way a bit, but Charles found the perfect angle and licked Mistress Eden's pussy until she had a loud orgasm while holding his head with both hands. Her thighs closed around him for a few moments before bursting open as she screamed joyfully. She smiled, her shoulders slumped from pure relaxation, and she released his head from her grasp.

"Thank you, Mistress, for letting me make you cum," he said.

"You're welcome."

It felt oddly pleasurable to offer his thanks for the act of giving her an orgasm and Charles couldn't help but smile at that pleasure.

"We still have a little time," she said, "and I'm afraid that I planted an idea in my head when I mentioned making you fuck yourself with a toy."

Charles's anus tightened reflexively.

"I'm going to let you masturbate while you do it, though," Mistress Eden continued. "You'll find a selection of toys with suction cup bottoms on the table. Pick one of the smaller ones, coat it in lube, stick it to the floor, and sit your ass on it. Ride it while you masturbate. If you stop riding it you will be permitted to orgasm. This isn't about me watching you hold something in your ass, Charles. This is about me watching you fuck your ass while you jerk off."

Charles stood and walked to the table to survey the toys. Only two looked small enough that it wouldn't be outright painful to ride. He picked the black one, which had a smaller head. Charles opened the bottle of lube and applied it liberally. He squirted some in his hand, too, to lube his cock for masturbation.

The toy stuck easily to the floor and Charles turned to face Mistress Eden before dropping to his knees and sitting back until the head of the dildo pushed against his asshole.

He took a deep breath and sat down. The toy penetrated him and Charles winced. Mistress Eden smiled at the pain on his face and for some reason that made his cock surge to life. He wrapped his fingers around it and began to masturbate while riding the toy.

"That's it," she said. "Fuck yourself for me, Charles. Fuck your tight ass for me. Don't worry, this will get easier too. You'll take it up the ass during every training session. It's an important part of destroying your ego and it must be done with regularity. Eventually I'll have you doing this at home, too. Taking it up the ass and jerking off. Associating your pleasure with getting fucked. Separating you from the typical thinking of a straight man. Molding your mind to think like a submissive, to think like a man whose purpose is to be used for the pleasure of a superior woman."

"I'm close," he said while riding the toy far faster than Charles had thought was possible. "Can I cum?"

"Good of you to ask, Charles. Yes, you may cum."

His load spilled onto the concrete floor. He rode the dildo throughout his orgasm and sat down on it once he'd expelled his seed, leaving quite a mess in front of him.

"Now clean up your mess. With your mouth," she instructed. "Lick up every drop."

Charles found the idea revolting, but that was probably the point of Mistress Eden ordering him to do it.

He bent forward, lowered his head to the floor, and licked up his cum. It tasted awful. It was utterly humiliating. It did, however, put him in a submissive headspace. Charles could feel it. He learned a great deal about himself in that moment, for he liked being in that headspace even while he was suffering through the decidedly unpleasant experience of licking up cum.

Perhaps Charles really was meant to be a submissive. Perhaps he was meant to be with a superior woman that would take full advantage of his willingness to serve her needs, to give himself over to her.

If Charles wanted to be with a woman like that, though, he'd need to better himself.

As that thought occurred to him, he made a mental note to profusely thank Mistress Eden once he was finished cleaning his load. In two shorts weeks she'd managed to have a significant impact on his thinking, on his approach to life, on his impression of himself.

She was, as it turned out, very good at her job.