Training Sessions - Part 6

Click here to read the previous parts of the story.

How does a domme reward her sub when he's been good and followed her instructions? There are so many options, for a sub finds so many things rewarding when it comes to his domme. The question, then, is how Mistress Eden will chose to reward Charles for being good and letting his new girlfriend Irina determine whether or not he gets to orgasm.

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Charles stood naked in the middle of Mistress Eden's room. His hands were clasped behind his back. She stood behind him, her breath warm on his neck, her body achingly close without touching him.

"I'm proud of you, Charles," she said. "You were vulnerable with Irina. You opened up. You showed her your true self."

Charles hadn't yet seen Mistress Eden as he'd walked into the room to find a note instructing him to strip, clasp his hands behind his back, and stare straight ahead until instructed otherwise. She'd walked in after what felt like an impossibly long time - though was probably no more than ten minutes - and after sharing the tale of his successful date with Irina all Charles wanted to do was turn around to catch a glimpse of his mistress.

Instead, Charles stared straight forward as she rested her fingers on the back of his neck for a moment. It felt like she was wearing gloves – shiny latex, he would have guessed - and as her fingers moved down his back, Charles felt a strong sense of relaxation work its way through his body.

"I promised I would reward you if you were good, Charles, if you refrained from climaxing and let Irina choose if you were permitted to experience the ultimate pleasure."

"Yes, mistress."

She grabbed a handful of his ass cheek and squeezed hard, though in a manner that struck Charles as borderline playful.

"The question, Charles, is what sort of reward do I want to give you?"

He knew better than to say anything, as it most certainly was not his place to express his desire for a reward without first being prompted by Mistress Eden.

"The wonderful thing about submissive men is that almost anything is a reward. I could make you hand wash the lingerie I got fucked in two nights ago and you'd almost certainly find it rewarding simply because I asked you to do it."

Charles was surprised to find rather vivid sexual imagery - featuring Mistress Eden - dancing through his head. For some reason he pictured her in soft, feminine lingerie while slowly riding a man's cock as they kissed.

"Your breathing just got a little heavier, Charles," she observed.

"Sorry, mistress. I was...I was thinking about you...about you having sex."

"Is that right?"

The imagery continued to play out in his head. Charles wondered if Mistress Eden owned lingerie like the baby doll he imagined her in, its soft material enhancing the considerable appeal of her body and offering an entirely different look from the dominant visage she put forth during their sessions.

"Does it excite you think about me getting fucked, Charles?" she asked.

"Yes."

Charles felt her breath on his neck, but Mistress Eden said nothing as the seconds ticked by. Then, finally, her lips caressed his skin and she offered a single, soft kiss.

"How interesting," she whispered. "We met at a bar. The same bar where you and I ran into each other, in fact. I didn't spank him in the parking lot and jerk him off in my car as a reward, though. Instead, I took him home. I made us drinks. We talked. We flirted. We fooled around."

Her lips offered a handful of kisses against the back of Charles's neck and shoulders and Mistress Eden moaned softly. It was enough to make his cock hard and Charles felt his legs tremble a few times as arousal coursed through him.

"I sucked his cock, Charles," she said softly. "I freed him from his pants, got on my knees on my couch, and took his remarkably beautiful cock in my mouth."

Charles's pulse raced and he could feel the depth of his breaths as his arousal manifested itself in multiple ways.

"You got my hand, Charles, and he got my mouth. I sucked him slow. I made him moan. I teased him. I don't give blowjobs like a supplicant who’s eager to please her man. I suck dick like a domme eager to control a man via his cock, and in his case it was an especially nice cock that my pussy was soaking wet for."

Her hand moved to his chest. Charles was tempted to look down, but he'd been instructed to stare straight ahead so he fought off the urge as her latex-clad fingers moved over his stomach and grasped his cock.

"So hard," she whispered. "All because you're thinking about your mistress enjoying another man's cock. Isn't that fascinating, Charles? Have you ever had cuckold fantasies before?"

"No. Never, mistress."

"It seems that you have one now, Charles."

Mistress Eden released his cock and her lips found his neck once more. The kisses were seductive and he suspected purposefully so, as she was trying to stoke the flames of his desire. She was doing a damn good job of it, too.

"I took him to my bedroom after the blowjob. I changed into lingerie for him. I put a condom on his gorgeous cock. I got on top and I rode him until I came so hard that my whole body trembled, Charles. I let him fuck me in missionary after that and he was skilled enough to make me cum again before unleashing his load in the condom."

She grabbed his ass and squeezed hard.

"Do you think you could fuck me to two orgasms, Charles?" she asked. "Do you think you have the skill to satisfy me like that, or would have been better off watching from your knees like a fucking cuck?"

Charles felt his legs tremble for a moment. His cock throbbed. He was awash in arousal he didn't entirely understand, and yet it seemed like Mistress Eden was right about his having a cuckold fantasy that he hadn't known about.

"I...I'm not sure I could fuck you to two orgasms, mistress. I think - with a woman like you, at least - that I probably would be better off watching from my knees like a cuck."

"A woman like me?" she asked softly.

"Confident. Dominant. Demanding - in a good way. Breathtakingly beautiful. Sexy. An exceptionally high caliber woman that possesses the skills to wrap any man around her fingers, that exudes the kind of confidence that makes a man want to give himself to her, to be in her service."

Silence followed and Charles worried that he'd crossed a line.

"Thank you, Charles," she said. "That's a lovely compliment."

Then Mistress Eden stepped in front of him. She wore elbow length black latex gloves, a pair of thigh high latex boots, simple black satin panties, and a sleeveless and skintight black latex top that was cropped short enough to leave her belly button exposed. Her cheeks were red and her eyes bright and Charles couldn't help but surmise that she too was aroused, though that had to be one of the perks of doing a job that aligned with her sexual desires.

Mistress Eden cupped his balls and smiled as she leaned closer. Her latex-clad breasts pressed into his chest and he held his breath for a moment at the pleasure of it. Her lips neared his neck, but no kiss was offered. Instead, the warmth of her breath tickled his skin before she spoke.

"You like Irina quite a bit, don't you?" she asked.

"I do."

"Do you feel guilty coming here now that you're with her?"

"A little," Charles answered. "I wouldn't be with her if I hadn't come here in the first place, though, and I feel like I still have a lot to learn. It's weird, I guess, and she might be really pissed when and if I tell her, but I just...I feel like I still have a ton to learn."

Mistress Eden squeezed his balls and pulled down. "It seems like she's in the midst of discovering her dominant side. If it becomes a part of her, she'll be grateful that you've had training. If not, your relationship probably wouldn't have worked out in the long run anyway." She smiled. "In case you haven't noticed, it should be clear that you need to be with a dominant woman to be happy, Charles."

"I know."

"Get on your knees."

Charles fell to his knees and looked up at Mistress Eden, who rested her fingers under his chin.

"Obedience makes my pussy wet, Charles," she said. "Especially when it's unquestioned. There's nothing finer than a man who simply does as he's told because he recognizes that the woman he's with deserves to be in charge of him."

"I like doing as I'm told," he replied, echoing a phrase he'd said to Irina that had seemingly unlocked some of her dominant desire.

Mistress Eden smiled, stepped back, and lowered her panties. Her fingers - clad in her shiny black latex gloves - disappeared into her pussy as Charles watched in utter fascination. It was the sound in particular that drew him in as it made perfectly clear how utterly soaked she was.

"Would you like to taste me?"

"Yes, mistress."

Her fingers were soaked as Mistress Eden pulled them free. She took a step towards Charles, extended her hand, and rubbed a single finger over his lips, coating them in her juices.

"You may lick your lips."

Charles did so slowly, savoring the sweetness of her juices as he looked up at his mistress.

"Part your lips for me."

He opened his mouth and she slowly placed her fingers on his tongue. He held her gaze while her fingers remained still, his taste buds now alive with her juices.

"Suck."

Charles closed his mouth around her fingers and sucked. He soaked up her juices. He closed his eyes. He moaned. It felt remarkably good to have any part of her in his mouth, even if there was a layer of latex between them.

"You're making me even wetter, Charles," she said. "I find myself thinking that I'd likely make you do more than watch if I cucked you. After all, a willing mouth is a terrible thing to waste."

There was only one thing she could have been referring to, and Charles thought of the strapon blowjobs he'd given in that room. It would be massively different to suck a real cock, of course, and yet he felt no sense of fear at the prospect, perhaps because in that moment his mind was entirely focused on serving Mistress Eden.

"Some men belong on their knees, Charles. You're one of those men. You want to be on your knees. It doesn't matter if you're with me or your beautiful girlfriend Irina. You want to be on your knees. You want to look up at a powerful woman and promise that you'll do anything to make her happy, even if it means taking a cock in this pretty mouth of yours."

Charles moaned and regretted it almost instantly. He didn't want Mistress Eden to think he was excited about getting to suck cock. He wasn't gay, after all. She smiled, though, and pulled her fingers free. They disappeared into her pussy once more with two more joining, leaving only her thumb free of the wet, plump folds of her loins.

"Perhaps I should bring a man to our next session, Charles. Someone I can order you to fellate for my pleasure. I can watch and masturbate while you suck dick for me. While your head bobs up and down in his lap. While he moans. While he puts a hand on the back of your head, calls you a cocksucker, and tells you to finish him off. I can watch and play with my tight pussy and have an orgasm while another man blows his load on your tongue, feeding you a cocksucker's reward that you will swallow once I've given you permission to do so."

All four fingers departed her pussy and entered Charles's mouth. She put her other hand on the back of his head and pushed deep into his mouth. Charles's eyes began to water and he gagged as Mistress Eden smiled down at him with an intense look of power-driven lust in her eyes.

She pulled her fingers free and wiped the saliva on his face. "Would you suck cock if I told you to, Charles?"

"Yes."

She extended her foot until her foot rested under the tip of his erect cock. "You may rub your pathetic dick over my boot."

He began to thrust, stimulating his stiff cock against the shiny latex of her boot. Moans followed as the surprising pleasure worked its way through his body, producing a steady stream of precum and leaving his loins tingling in a remarkably satisfying manner.

"Lick your mess off my boot."

Mistress Eden stepped back and Charles fell forward and licked his precum from the shiny, warm latex of her boot. He did so ravenously and driven by the arousal that gripped him, arousal Mistress Eden had expertly stoked to the great heights it now rested at.

"Stand up," she said.

Charles stood and Mistress Eden stepped closer and surprised him with a long, slow, deep kiss. Her hands moved over his body but he kept his clasped behind his back as he knew that a punishment would follow if he touched her without permission.

"You're a good kisser," Mistress Eden whispered.

"Thank you, mistress."

She kissed him on the cheek and let her lips linger. "Irina's a lucky girl."

Mistress Eden walked away and Charles stared straight ahead. She'd walked in the direction of her wall of toys and Charles suspected she was choosing a dildo for her strapon harness. He would soon end up on his knees once more, this time his mouth filled with a rubber cock instead of her fingers.

Imagine his surprise, then, when Mistress Eden returned holding a dildo that was clearly not meant for a strapon. Instead, she placed it over Charles's cock and fixed it over his balls with a rubber strap. It fit tightly over his erection and gave him greater length and thickness. Charles looked down and immediately understood the confidence of men with big cocks.

"You get to be inside me as your reward, Charles," she said. "I'm sure it's not quite as you imagined, but there's very little reason for me to settle for a cock as average as yours when I can enjoy something bigger and better."

"Yes, mistress."

"Wait here."

Mistress Eden walked out of the room. She returned soon after carrying an armless chair with a black leather seat and back. She set it behind Charles and directed him to sit.

Then she was astride him. She took his 'cock' inside her. He felt very little direct stimulation - the toy had gotten a bit tighter - but the warmth of her ass against his upper thighs and the sudden closeness was blissful.

"You may touch me," she whispered.

Charles moved his hands to her ass and caressed her smooth skin.

"You may kiss me."

He leaned in and kissed her neck as his hands moved up her back and over her latex top. She began to grind on the toy that surrounded his cock, sliding her hips back and forth and generating heat between their loins.

"You feel so good inside me," she said.

"Yes, mistress."

He squeezed her ass and kissed her neck and cheek, his lips moving ever closer to hers. Then, to his delight, Mistress Eden took his head in her hands and kissed him with remarkable depth and passion. Her tongue slowly moved into his mouth and she began to ride his cock, bouncing up and down, her beautiful ass falling onto his thighs over and over.

"I'm so wet for you," she whispered.

Charles couldn't feel much direct stimulation, and yet he was turned on to such a degree that he was no longer thinking straight. He was, in a way, having sex with Mistress Eden. It felt genuinely passionate, too, though a small part of him felt certain that she was simply playing a part, that she was offering the reward she'd promised and making it pleasurable for him by acting as if she was utterly enthralled with the sex.

"Charles...you're going to make me cum."

He squeezed her ass and they kissed again. It was a genuine kiss. It was deep and passionate. It had to be genuine, Charles told himself. It had to be.

She came while they kissed. She sat on his cock and moved her hips back and forth, her legs trembling as he held onto her ass and sucked on her tongue.

"Fuck...that was incredible," she whispered while holding his head against her chest.

"Thank you, mistress. I...I really enjoyed that."

Eventually, she stood and removed the toy from his cock. She held it in front of Charles and he stared at her juices and a bit of thick white cream that must have come out of her pussy.

"May I suck it clean, mistress?" he asked.

For a moment Charles thought he'd be punished for his boldness in asking for pleasure. Instead, Mistress Eden pushed the tip of the toy into his mouth. His lips stretched around it and he sucked, swirling his tongue over the head. He felt the thick cream in his mouth. He swallowed it. He couldn't escape the thrill at consuming something that had come from her body.

Charles sucked until his jaw was sore. He would have kept sucking, too, but Mistress Eden pulled the toy free and set it in his lap as she studied his face and smiled. He couldn't read her expression, but to Charles it seemed like she was looking at him as something more than a client. He quickly told himself that was pure fantasy, though.

The look washed away and Mistress Eden stood and moved back to her wall of toys. Charles stared straight ahead and waited.

When she returned, Mistress Eden was wearing a strapon. The cock was thick and lifelike, including the color. It even had a foreskin that would pull back when she stroked it. Mistress Eden's face was a picture of control, as if she'd become a different woman in the short span of time she'd been on the other side of the room.

"A good domme always finds a way to guide her submissive back into the right headspace, and that's especially important after receiving a reward like the one I just gave you."

"Yes, mistress."

She spit in her hand and stroked her cock, which looked remarkably lifelike from Charles's position.

"You're going to get on your knees and suck my cock. I'm going to fuck your face a little, too. It's going to be unpleasant. Then, you'll get on your knees on that chair and I'll fuck your ass doggystyle until it hurts. I'll have an orgasm. I'll spank you. I'll pull your hair. I'll call you names. I'll degrade you. I'll return you to your submissive mindset and then I can continue your training."

"Thank you, mistress. I'm so grateful for you. I want to be a good submissive and your teachings are invaluable."

For a moment her face softened and it looked like she was going to smile. Then, Mistress Eden pointed at the floor and Charles slid off the chair and onto his knees.

"Suck my cock. No fucking teeth, either, or I'll punish you. If you're going to suck a real man's dick for me, you'll need to do it well."

Charles went to work, though he found himself thinking of kissing Mistress Eden as she rode him, as she came on him, as she held him close after her orgasm. Was that really just her putting on a show or was there a chance she'd crossed a boundary and developed something akin to real feelings for him?

Charles wasn't sure what he wanted to answer to that question to be. He liked Irina a great deal, after all, and it seemed like they had a real future, and there was no real evidence that Mistress Eden had real feelings for Charles. Still, some part of him wanted Mistress Eden to have real feelings for him, to want to pursue more with him, to want him in a real way.

Charles brushed it all aside in favor of serving her in that moment. He offered his mouth and his ass. He took a good hard fucking. He took a spanking. He took her verbal degradation. He took it all and she had an orgasm while guiding him to the submissive headspace required for the training that would unfold over the rest of their session.

By the time the strapon fucking was over, the questions had been pushed out of his mind and he was on his knees feeling sore, humiliated, and eager to learn how to be a good submissive partner to a dominant woman.