Training Sessions - Part 4

Click here to read the previous parts of the story.

After encountering his mistress at a bar - and serving her in the parking lot and her car - Charles returns for his regularly-scheduled training session and finds himself as eager as ever to please the woman that has revealed his submissive side and is training it to become the guiding light of his future love life.

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"Good morning, Mr. Simmons," Lydia said as Charles stepped into the well-appointed lobby. "Please have a seat. Mistress Eden is still with a client."

"Thank you."

Charles sat and reached for his phone. He thought better of it, though, instead choosing to remain in the moment, to show a sense of discipline, which was part of being a good submissive.

At first Charles merely stared straight ahead, but he found his attention drawn to Lydia. He'd gone down on her more than once as part of his sessions with Mistress Eden so it wasn't as if he was unfamiliar with her. Charles understood that it would be impossibly rude to speak of those sessions in the lobby, but he couldn't help but think of the taste of Lydia's pussy, of the way she moaned as he went down on her, of the time that he'd been fucked by a strapon while tending to her pussy with his tongue.

The third time he glanced her way, Charles noticed Lydia reach down and rub her calf. She winced slightly while doing so and he found himself possessed by a desire to serve her.

"May I rub it for you?" he asked.

He'd caught her off guard, at least based on the look on her face. Lydia studied him for a few moments, adjusted her glasses, and then smiled. "If I said yes, what would you do?"

"I'd approach the desk and fall to my knees. I'd ask for permission to come around your side of the desk. I'd crawl into position. I'd rest your foot on my thigh and rub your calf slowly, applying gentle pressure at first until the pain receded enough to rub with greater force."

"A very thorough answer, Mr. Simmons," she replied. "Yes, you may rub my calf."

Charles stood and approached the desk. He fell to his knees. He asked for permission to come around her side and was granted said permission. He slipped off her high heeled shoe and rested her foot on his thigh. He ran his fingers over her calf and rubbed it gently. She winced, but after a short while he felt her muscles relax. He glanced at her toes and noted how lovely they looked with a deep shade of red painted over her nails. Charles was momentarily gripped by a desire to suck on them, so he looked away, instead focusing on the area he was rubbing.

"Any submissive needs to be good with his hands," Lydia said, "especially when it comes to massaging his dominant partner. It's remarkable how much pleasure you can offer someone through a rub."

Charles continued to massage her calf, working all the tightness out of her muscle as Lydia's sense of relaxation deepened. It was when she leaned back and closed her eyes that he felt as though he'd accomplished his stated goal, which was when he asked if he could rub her other calf as well.

"You may," she said.

Charles wasn't the slightest bit embarrassed to have gotten semi-erect as he offered a massage. It felt good to be on his knees in front of a beautiful woman and it felt even better to be able to serve her in the manner Lydia had permitted.

"You know, if we weren't at the front desk, your head would end up between my legs, Charles," she said. "I'd give you permission to tend to my clit as a reward for your dedication to my pleasure."

"That would have pleased me," he replied. "Very much so."

Lydia moved one of her feet between his legs and massaged Charles's cock to a full erection. He tried his best to focus on continuing the massage, though the sudden burst of pleasure made it difficult to do so.

"A small reward," she said with a smile.

"Thank you."

The sound of footsteps created a gentle sense of panic in Charles before he realized that he was in one of the few places in the city where his behavior made perfect sense.

"Thank you for today, Mistress Eden,” someone said. “It was a pleasure serving you, as always. I...I'm so grateful for your training."

The desk blocked his view of the man speaking, but that didn't stop feelings of intense jealousy from washing over Charles. He had no right to think of Mistress Eden as anything more than his therapist - of a sort - but he clearly couldn't help himself. He suspected that having served her outside of the offices - and of her having made him cum during that service - had convinced him that Mistress Eden felt more for him than a typical client. He had no real reason to believe that, though, other than what was clearly a great hope that she wanted more from him than to get paid to train him in the art of submission.

"The pleasure was mine, Gregory," Mistress Eden replied. "You're making great progress. Remember, though, that you need to find the courage to try and be your submissive self in the real world. It's hard to find a woman that's eager to dominate a man, but you must start going on dates. You must put what you've learned in our sessions to use in the real world. That's the only way to know how much more you have to learn and it's certainly the best way for me to know how to refine your training."

"Of course, mistress. I'll see you next week."

Charles could hear the devotion in Gregory's voice and he wondered if he sounded the same way when he spoke to Mistress Eden. He wondered if that sense of devotion was real or if Gregory was putting on a show. He wondered if Mistress Eden liked Gregory better than him. Then he harshly instructed himself not to think of Gregory at all, for the other clients that Mistress Eden worked with had nothing to do with Charles.

"What's going on here?"

Charles looked up to see Mistress Eden smiling at him from the other side of the desk.

"Charles noticed that my calf was a bit sore. I went a little too hard in the gym yesterday and came away with a minor injury. He asked permission to rub me. He crawled behind the desk. He applied his skills in massage and he'd made a genuine difference. All told, he's been a very good submissive, so I'd say that your teachings are making a real difference."

"Are you ready for your session, Charles?" Mistress Eden asked.

He nodded and looked up at Lydia. "Thank you for letting me massage you. It was a pleasure."

She leaned forward and surprised him with a soft kiss on the cheek before Charles got to his feet and followed Mistress Eden out of the lobby, down the hallway, and into her training room.

"Strip," she instructed.

Charles removed his clothes and folded them by the door. He moved to the center of the room and stood with his hands at his sides as Mistress Eden watched with her arms crossed.

"Have you masturbated to the thought of me since I last saw you?" she asked.

He nodded.

"And what was the content of your masturbatory fantasy?"

"What we did in the bar parking lot. The way you punished me. The way you fucked my face with your pussy. The way you jerked me off while kissing me. The way I got to make you cum and the way you made me cum."

Mistress Eden unzipped her latex shorts and slowly worked them over her hips and boots, holding them aloft on the edge of her fingers as she approached Charles. He glanced at her pussy and spotted signs of arousal. The jealousy he'd felt earlier returned as the source of that arousal had likely been her earlier client, Gregory.

Mistress Eden turned her shorts inside out and extended her hand until Charles was staring at her juices on the latex. "Lick it up."

He leaned forward and licked her sweetness from the shorts. He ran his tongue over the spot against which her pussy had rested and did so over and over. He didn't taste much outside of the latex, but there was something truly thrilling about lapping up her wetness.

"Thank you, mistress," he said.

"What would you guess was the source of my arousal?"

"Whatever you did with your previous client, Gregory."

She smiled. "You picked up his name."

Charles nodded.

Mistress Eden tossed her shorts towards the door and moved behind him. She grasped his ass cheeks and kissed the back of his neck.

"Do you think it's possible that I got aroused when I saw you on your knees in front of Lydia? Do you think it's possible that my pussy is wet because I saw you and thought of your submission at the bar and in the parking lot?"

Charles chose to answer honestly. "I wish that I was the source of your arousal, but I suspect I'm not, at least not entirely."

She stepped closer and the warm latex of her sleeveless top pressed against his back. Her fingers moved up his chest until they rested against his throat. Her lips found the back of his neck and she kissed him softly while squeezing his throat, creating a gentle sense of panic as Charles's body sent signals of worry from head to toe.

"You're right that you weren't the sole source of my arousal," she whispered. "I do love my job, after all, and Gregory walked out of here with a severely reddened ass. He earned that punishment, though, as he masturbated when I allowed him to taste my pussy. His hand was on his cock for only a few seconds, but his disobedience was deeply frustrating, hence the punishment. As you know, I find pleasure in punishing a man, and so I found pleasure in reddening Gregory's ass."

Her fingers left his throat and Charles felt his body relax. Mistress Eden caressed his ass for a few moments and then moved her hand between his legs to grasp his cock and stroke him. Charles immediately found himself back in the bar parking lot, in the backseat getting a handjob while he kissed her and played with her tits, while she told him that he deserved to feel good, while she gave him the best handjob of his life.

"Punishing him is not the only reason my pussy was wet, though," she said. "Seeing you brought me back to the bar, to the fun we had. I was surprised at how vivid my memories were, in fact, how much warmth I felt for you as I watched you massage Lydia's calf."

"It makes me happy to know that I served you well that night, mistress."

Her lips neared his cheek, but she stopped short of kissing him. Instead, she squeezed his cock hard enough for Charles to worry and then stepped away and took off her top, leaving her naked except for her boots.

"Have you been on a date since I last saw you?"

He nodded. "Her name was Irina. We met on Bumble. I put something in my profile about preferring to be with a woman that likes to be in control. I got fewer responses, but the women that responded actually seemed a lot more interested in meeting me."

Mistress Eden smiled. "I'm proud of you, Charles. It takes courage to put yourself out there like that, especially since you're putting the purer version of yourself into the world. Rejection of your true self is undoubtedly more painful, and yet acceptance feels even better. How was your date?"

"It was good, mistress. Really good, actually. We went out for drinks and it went well enough that I suggested we get dinner. We kissed afterwards. It felt...electric, if I'm being honest. She must have felt it too, because she invited me back to her place."

Mistress Eden sat in her leather-bound chair and spread her legs. She grasped one of her breasts and ran her fingers over her taut stomach and between her thighs. "What happened at her place?"

"We had a drink. We talked. I...I offered her a foot massage."

A finger disappeared into her pussy. "And how did she respond to that?"

"She asked me if I was a foot fetishist. I told her I wasn't, that I assumed most women really liked a foot massage and that I wanted to do something that would make her feel good."

"Very good, Charles. How did it feel to be so honest with someone you barely knew?"

"Terrifying," he admitted. "Every word felt like it might lead to her laughing in my face."

"Did she laugh?"

He shook his head. "No. In fact, she let me give her a foot massage. I carefully removed her heels and set them on the floor. I rested her foot on my knee. I rubbed it slowly as we talked. I moved from one foot to the other and rubbed them both at the same time at a few points. I...I wanted to show her that I was really only interested in her pleasure, that I wasn't going to try and drag her foot to my cock to turn me on."

Mistress Eden stood and sauntered towards him. She stopped close enough that he could feel the warmth emanating from her skin. He looked down to see three fingers disappear into her pussy and was soon rewarded with the pleasure of sucking her juices off of them.

"It excites me to know that my training is taking hold, Charles," she whispered. "Were you permitted to do more than rub her feet?"

He nodded and she pulled her fingers from his mouth.

"After roughly half an hour of rubbing her feet she said that I could rub her calves, too. After that she said I could rub her thighs a little, though I wasn't to get fresh."

Mistress Eden fingered herself again, but this time she took his cock in her hand after pulling her fingers free from her slippery pussy.

"Eventually, after nearly an hour of massage and conversation, she spread her legs and invited me between them. My mouth, that is. She let me kiss her pussy through her panties. She let me take them off. She let me pleasure her with my tongue. She was generous enough to let me make her cum twice."

"And was she generous to you, Charles? Did she make you cum?"

He shook his head. "No. We did make out, though. She let me play with her tits a bit. She stroked me through my pants. She never moved to go further than that, though, and I didn't push for it."

"Nor should you. Your domme - even if it's a first date - should always have total control over your cock and your pleasure."

"Yes, mistress."

Mistress Eden stepped away and Charles turned to admire her ass and legs. She walked towards the area that held her many tools of domination and selected a strapon harness and a sizable toy. Once dressed and wielding a cock, Mistress Eden returned to her chair and sat.

"Worship my cock," she demanded.

Charles fell to his knees and crawled towards her. He kissed his way up her legs, starting with her boots and slowly working his way to her thighs. He kissed and licked his way up the shaft of her strapon, too, showing deference to the appendage and doing his best to be worshipful.

"Few men understand that it takes great patience to be a true submissive," Mistress Eden mused as he tended to her strapon like it was a real cock. "You seem to have grasped that bit of truth, though, as demonstrated by your willingness to massage Irina for more than an hour before you were permitted between her legs. To be a true submissive requires that you set aside your desires in favor of meeting your domme's needs, even if they don't entirely align with yours. I'm sure, for instance, that you would prefer to eat my pussy until I've cum on your face. That's not what I want, though. I want to see you throat my cock. I want to see your eyes water as you suck it. I want to see you suffer for my pleasure. I want you to get my cock wet with your saliva so I can bend you over and fuck you in the ass until I have a screaming orgasm."

Charles had worked half the cock into his mouth as she talked and he continued to push, lubing more of the shaft with his spit as he conquered his gag reflex. He knew better than to pull back to speak. He knew it was not his place to talk in that moment, that he was meant to suck her cock and do so worshipfully, that he'd surrendered himself to being a tool for her pleasure in whatever way she saw fit to use him.

After a thorough blowjob that left his jaw sore, Charles submitted his ass to a long, deep, hard fucking with spit as the only lubrication he was offered. It was uncomfortable, but that was the point. His ass was meant to be used as a vehicle for Mistress Eden to cum. Charles took the fucking while moaning as if it felt spectacularly good. He got spanked. His hair got pulled. He was called names. He took all of it in service to his mistress, to the woman he'd developed feelings of a sort for despite being told not to.

Mistress Eden came hard while fucking him. She pushed every inch of her strapon inside him, fell forward, and rested her naked body on his back as Charles closed his eyes and smiled brightly at how good it felt to be so close to her.

"Thank you, Charles," she said while still inside him. "That was an exceptionally good orgasm."

"It was my pleasure, mistress. Thank you for letting me worship your cock. Thank you for fucking me. Thank you for letting me make you cum."

She pulled out and removed the strapon harness. Charles got up from the leather bench he'd laid on for his fucking and returned to the center of the room. His cock was half hard and dripping precum as Mistress Eden sat in her chair, this time with her legs crossed.

"Do you have another date with Irina?" she asked.

"I do. This weekend."

Mistress Eden sat silently and studied Charles for what felt like an uncomfortably long time. Then she spread her legs, putting her pussy on display and drawing his gaze between her thighs.

"On your knees. Crawl to me. Place your face close enough to my pussy that you can smell me."

Charles did as instructed and once in place he inhaled deeply, filling his nose and lungs with the scent of his mistress. His body hummed with desire - need, even - as he waited for permission to use his tongue to please her.

Mistress Eden's fingers moved between her legs and she began to masturbate. Her wetness ensured a symphony of beautiful sounds and as they filled his ears Charles felt his desire to pleasure her deepen.

"You will not masturbate this week," she instructed. "You will not cum. I want your body teeming with desire when you're on your date. I want to see if you can still be a good submissive despite feeling a deep need to cum. If you cannot, know that I will punish you during your next session. If you can be good for Irina, though, I will reward you, Charles. Do you understand?"

"Yes, mistress."

Mistress Eden closed her eyes and masturbated to an orgasm while Charles watched from just a few inches away. He inhaled her scent. He listened to her pleasure. He yearned to use his tongue to please her. He was denied that opportunity, of course, and he handled that denial in stride, for it was his task to do so.

Afterwards, Mistress Eden laid on the bench upon which Charles had been fucked. He was not permitted to fuck her, of course. Instead, he was invited to worship her asshole while she answered texts and emails, largely ignoring him. It felt like both punishment and reward and Charles pondered the notion that patience was a significant part of any good submissive's repertoire. He suspected that her demand that he not cum that week was connected to the lesson of patience and that it would be more difficult to overcome his desire and dedicate himself entirely to Irina's pleasure.

That was the challenge, though, and Charles wanted - more than anything, really - to be a good submissive, so he resolved to do whatever it took to achieve that goal.