Training 1


Penny had kept rick in chastity just shy of three weeks. It had been the longest term of denial yet and the results were palpable, although not always predictable. He displayed, at some moments, levels of obsequiousness that cause Penny instinctive arousal. At other moments, her slave became rebellious and surprising in other ways.

He had complained two weeks into his denial that it was beyond the scope of his expectations. He expressed his opinion with some anger, but remained partially restrained. It was the restraint that turned Penny on the most, because she knew he would lash out more if his genitals were not locked in chastity. She calmly met his stifled anger with her own.

“I can always extend the denial. It will help you understand and learn better,” she said with a calm voice.

Meekly the physically powerful man before her mumbled, “No. I don’t want it to be extended.”

“Then kneel down before me and apologize,” Penny instructed. She was still in the phase of the relationship during which immediate obedience, while gratifying and arousing, still took her with surprise. rick  knelt down and as instructed bowed his head to look down at her feet.

Penny stepped forward and unbuttoned the top of his shirt. Her motivation was singular. She wanted him in slavery, but still believed the seduction that lured him voluntarily lower and lower was the best methodology to employ. A former professional dominatrix was advising her and, to date, every recommendation made had worked perfectly. So Penny started teasing his pert nipples to elicit dulcet moans. rick calmed like an animal being tamed. Penny loved seeing the transformation and the steadily shrinking time between tantrums and obedience.

The coach told her it would be difficult and, depending on the style of dominance preferred, Penny could train in different ways, cruel and demanding or loving and calm.  Penny’s choice was the loving approach to induce voluntary compliance at all times, even to the most casual of suggestions. Her coach agreed this was her favorite approach, but did require some patience. 

“I don’t like when you talk back, nor when you hint of raising your voice to me. You agreed to the terms of your training weeks ago. It’s my responsibility to help you become the best man you can be. I believe the best man you can be is a weakling sissy.

“You remember the rules. We can take your chastity device off very easily,” she reminded him. “You only need to be in strict bondage so that I can safely remove your chastity. You know how tempted you get to touch yourself. That privilege no longer exists. You admitted you’ve been touching your little penis since you were a boy and need someone to help you learn restraint. I am that someone.”

rick was silent except for the soft moans coming out of his mouth. They were moans not as much about arousal as they were resignation. The chastity device in his pants restrained his penis to prevent an erection. He secretly knew that his recalcitrance could lengthen the denial even longer.

During the first week, it felt like a sexual game. But now it was more. His mind was being shaped although he didn’t realize it. He still believed at moments that it was still “role play.” He still thought he had choices, but Penny never intended to let that happen again.

“I just made a decision,” Penny said. “You are no longer permitted clothing in this household. You are a recalcitrant boy with no self-control. Your mommy never trained you properly. You are about to get the training that a mommy should give a boy. It means the boy should always be naked, humble, and eager to obey. I want you to go to the bedroom, undress, put your clothing away, and then return to me.”

Penny continued to play with the boy’s nipples and knew the strain was growing in his pants. These were the early stages of the power shift. Penny didn’t know even in her own mind how far she would eventually take her slave. The decision to keep him naked, she would later reminisce, was a mundane moment compared to the extremes she later had him endure.

She released his nipples and said, “now go.” He started to walk towards the bedroom and heard Penny say, “Quickly!” She giggled as he started scurrying in fear. She sat comfortably in a chair and smiled contentedly when he returned naked wearing nothing more than a metal device on his cock and balls. It was time to escalate the use of training utensils.

“Kneel,” Penny commanded softly. She never needed to raise her voice again. rickie was past the breaking point and she loved it. In her mind, he was no longer rick, the man the public knew. He was rickie, the Yin to her Yang. The obedience to her control. The feminine to her masculine. She was the power now. He was the bitch, a feminine animal to be conquered.

Penny looked down and observed a less than optimum position, because it was not humble enough. rickie knelt with his knees together and hands on his hips, elbows out. It was unacceptable. He hadn’t noticed the riding crop, nor the butt plug, Penny had by her side. She took the riding crop, tapped his elbows, and said, “Drop your arms.”

rickie obeyed and as her coach had instructed her to do, Penny once again said, “Good boy. Do you want to be a good boy?”

“Yes, Ma’am,” rickie said without hesitation. He was back in his place and Penny felt very gratified. Each episode of rebellion was becoming milder and milder, just as her training coach had predicted. Her coach insisted that the time would come when his will was fully broken. At that point, the rebuilding and molding of her slave could fully begin.

Penny took the riding crop and flicked it over her slave’s nipples. She then tapped each of his inner thighs and told him to spread, which he did without hesitation. She then instructed him to sit back on his heels and clasped his hands behind his back. He obeyed. She then told him to raise up so his genitals would dangle for her.

Penny had fantasized many times about spanking the testicles of an adult male. She considered it an entitlement to Female Superiority and a symbolic gesture of acceptance and servitude. The first spank caused rickie to flinch. The second was firmer and caused him to flinch again. “Don’t move, baby,” Penny instructed gently.

Throughout the initial training and conquering period, Penny continued to issue commands in soft kind tones, almost motherly. Her coach told her that the ideal situation was a lifestyle in which her husband would become her slave wife, accustomed to gentle vocal prodding. Penny reached out and played with a nipple, granting her slave the pleasure he needed and she started continuing a rhythmic tapping on his testicles.

She saw the strain as his penis futilely tried to grow. “Would you like permission for an erection?” Penny asked playfully. She knew the answer. She always knew the answers before her slave did. He moaned loudly and appropriately used the right words to earn the erection.

“Yesssss. Please, Ma’am. Please let me have an erection.”

“You know the rules, sweetie. I’ve a chair in the bedroom set up. It is where I will tie you and show you a little surprise. But first, we have to enhance your need. I’ve decided that you may only have an erection while strictly bound. You know this, yes?”

“Yes, Ma’am,” rickie moaned while feeling the confusion of arousal on a nipple mingled with painful spanks on his testicles.

“To teach you properly, I’d decided you need to be penetrated with this pretty little toy.” Penny held up a pink butt plug and watched rickie’s eyes widen. “From now on, you may be erect, but only if bound and penetrated.”

rickie had expressly told her early in the relationship that anal penetration was a limit with which he was uncomfortable. Penny assured him that she would test his limits and this was one of those moments. She was unsure if he would accept the conditions of her offer, but was firm in her position that it would remain purely “an offer.” If he refused, there would be no erection.

rickie looked at the device and felt he would not be able to handle it. He told her that it was too much and was shocked when Penny accepted his answer. She added that there would be no erection as a result. rickie’s eyes widened as dozens of thoughts went through his mind in a flash. 

Will I never get out of this, he wondered? Could I fit that in me? 

Could she fit that in me? 

Is this real? Did she wish for this? This is all for an erection? 

Will I ever cum again? 

I’m ready to beg for an erection, which will probably only frustrate me, but it’s worth it… 

Is it? She once told me to be careful what I wished for…“Wait.

I’m sorry. I want to try,” rickie said in a whiny voice.

“Aw. I’m sorry too, baby,” Penny responded while pouting her bottom lip playfully. “You had your chance. Perhaps another time. You need to learn. When Ma’am offers you opportunities, you should accept them. I promised you I would never make you do anything. Everything that happens to you will be because you want it, with the exception of your chastity. That is non negotiable. Eventually you will learn to beg for the things I offer.”

“Please, Ma’am,” rickie pleaded. This time he was less whiny and seemingly eager to obey.

“Please what, baby?”

“Please put it in. I want it.”“But you said you didn’t…”

“I know. That was a mistake. I should have said I was ready.”

“Ah, poor baby,” Penny said with mock empathy. “I don’t want you ready. I want you hungry. I want you to desire everything I do. I want you to share in that. I want you to want to be fucked in your pussy hole.”

Her words shocked rickie. He didn’t expect such vulgarity and realized she was much more powerful than he anticipated. He was fearful and helpless. “I do,” he finally said. Penny wasn’t sure if she believed him. In fact, she knew she didn’t and it was an even bigger turn on. It meant that she could get him to do things he didn’t want, but she did.

Penny stood. She looked down at rickie on his knees and saw him helplessly looking her in the eye. She reached down and started playing with his nipples again. “Beg,” She said.

“Please, Ma’am,” rickie begged while moaning and arousal. “Please put it in me. I want it.”

“Do you?” Penny asked while knowing her boy was in a state of near hypnotism.

“I do. Please.”

“I think you just want to be hard. But I want you to want to be fucked like a bitch.” rickie paused and Penny asked directly. “Do you want to be fucked like a bitch?”

rickie paused and finally said, “Yes, Ma’am! I do. Please.”

“Please what, baby?” She asked playfully. She knew he was hypnotic now with desire. She could make him run around the block naked, she thought. But the fun of making him admit his humiliation was even more delicious. 

“I don’t want to put it in you,” Penny said, emphasizing the last words. “I want you to want to be fucked. Do you?”

rickie moaned louder and begged. “Yessss. Please, Ma’am. Please.”

“Please what?” Penny asked calmly.

“Please fuck me.”

“Good boy… but not good enough. Try again.”

“Please fuck me, Ma’am.”

“Good boy. You’re getting closer. Try again.”

“Oh God!” rickie said, verging on panic. The floodgates opened. “Please! Please please please. Please fuck me, Ma’am. Please fuck my hole. Oh God. Please fuck my male pussy. Please.”

rickie ran out of words, but Penny had not. “Like a bitch?”

“Yes, please, Ma’am. Like a bitch.”

“So you’re saying you’re my bitch?” She asked, pushing him to the limits of humiliation.

“Yes. I am Your bitch.”

“Then how do you want to be fucked? Tell Ma’am.”

“Oh god!” rickie was out of control of himself and under the spell Penny’s dictates. “Please fuck me like a bitch. Please make me your bitch. Please, Ma’am. Please.” The last words were uttered in complete surrender. He knew it was over. She had checkmated him and there was nothing he could do.

Penny’s instinct told her to make him wait for another session, but her own eagerness to penetrate her slave for the first time overtook her. “Kiss my feet and apologize for your recalcitrance today. You’ve been a bad boy. You tell Me you want to be a good boy. But you’re not.”

She looked down and saw a man being broken. Her pussy moistened as the power washed over her body. rickie wasted no time kissing her feet and, when Penny kicked off her shoes, he began licking her toes. She extended her big toe of her right foot and said suck it. He obeyed without hesitation.

As he kissed her feet and sucked her toe, Penny used the riding crop on his bottom. The strikes were not loving taps, but instead punishment. He had been recalcitrant. He had complained about his chastity. He did not move quickly enough when she sent him to get naked. He needed to learn. After several lashes which left marks on his bottom, Penny said, “it’s time to learn a new position.”

“I will call this position ‘present.’ It means you will present your hole to me by facing away from me, raising your bottom in the air, moving your knees apart and extending your arms. In this position you symbolize total acquiescence to my power and voluntary acceptance of penetration into your male pussy hole.”

To his credit, rickie desperately continued kissing Penny’s feet and sucking her toes. Suddenly, she said, “Present!” rickie moved without hesitation. It was a beautiful sight for Penny.

She took her time, she admired his exposed bottom and immediately considered that would need to be shaved in the future. For the time being, she simply put lubrication on the toy and then held it at the tip of her slave’s anal orifice. “Push, baby,” Penny said softly. “Show Ma’am how much you want to be My little bitch.”

rickie pushed back, but struggled. It was hard for him to get the toy inside. Penny decided to show leadership compassion but coming off the chair and crouching beside her slave. She teased his left nipple while her right hand applied pressure to the toy. Rickie held firm as Penny started pushing until the thick nodule was almost in her slave’s body.

Penny thought she might orgasm from the feeling of power. She heard rickie moan in earnest pain, but was relentless in her decision and finally pushed the big nodule all the way in. rickie gasped and shivered in pain. Penny stood bent over him and then reached around him to play with both of his nipples. She was an owner domesticating a pet.

The pain subsided and rickie actually felt some degree of pleasure as his hole was recovering from the wide penetration and now only modestly stretched and relaxing. It was a unique feeling of arousal that caused his penis to twitch even more in his cage. Penny sat back in her chair and looked at her slave. He remained in the ‘Present’ position, much to her pleasure.

“It’s too bad you didn’t accept my offer immediately,” the Ma’am stated calmly. “You don’t deserve an erection, but I’m so very proud of you. I assured you that you must be bound and penetrated to earn an erection, but didn’t guarantee it.  This is one of those times you won’t be rewarded, because you don’t deserve it. But at least you know you are now a fuck toy capable of receiving penetration. That is a big milestone in your development. So think about that, as Ma’am goes to the bedroom and undresses.”

“You will think about the events of the last hour,” rickie’s Wife/Owner instructed. “I need you to ponder your behaviors and work to be better. I am proud of you, though, because your penetration and role as my new fuck toy has earned you the right to worship my pussy. Stay in this position until I summon you to my chambers.”

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