- Free Sample
“What’s going on?” Danielle asked with a raised eyebrow.
“Some new training,” Brenda said, winking wickedly. “I have you for the next two hours.” He pulled a key out from inside his camisole and teasingly dangled it. The key on a chain had a tiny dildo on the end. “Time to play with some toys,” Brenda said, almost excitedly jumping. He unlocked the wooden box’s padlock at Danielle’s bed’s end and momentarily rummaged around. “Hmm, let’s see. I don’t want to start you off too big,” he said, rubbing his chin. “This is something you work your way up to. A-ha.” Brenda stood holding two toys in his hands. “Oh, what memories,” he said wistfully. “I started on these same ones.”
“Ew, I hope you washed them,” Danielle said with a naughty glint in his eye.
“A sissy always maintains the highest standards of cleanliness in all things,” Brenda said snootily.
Danielle chuckled. “Mistress has trained you well, sweetie.”
“Of course! Now let’s start with the butt plug. You’ll be expected to wear this from now on.”
“All the time?” Danielle asked, his eyes bulging. “What happens if I need to do—err—you know?”
Brenda exaggeratedly rolled his eyes while letting out a loud puff of air. “You take it out, stupid,” she said haughtily. “Then, once you’re done, you put it back in. It’s not rocket science.”
“I suppose,” Danielle said and sighed.
“Just don’t let Mistress catch you without it. You don’t want that punishment, trust me.”
“What’s the punishment?”
Brenda closed his eyes and held his breath. Something Danielle had learned means he doesn’t want to talk about it.
“OK, so let’s get it in,” Danielle said, and Brenda relaxed.
“Good, now stand, and lean on the vanity with your elbows.”
Danielle did and poked his ass out for Brenda, who lowered his panties to reveal a firm butt. Brenda dropped to his knees, pulled Danielle’s butt cheeks apart with his fingers, and poked his tongue inside. The feeling startled Danielle, and he pulled away.
“What are you doing?” Danielle asked, standing and staring at Brenda with narrow eyes.
Brenda shook his head while gazing at the ceiling. “I need to lube you first, sweetie.”
“Then use lube,” Danielle said.
“A sissy’s mouth is the lube, always.”
Danielle laughed. “That’s silly. How do I lube my ass when I put the thing back in?”
Brenda took the butt plug and sucked and spitted on it. He then held it up for Danielle to see.
“All right, just warn me next time,” Danielle said, assuming the position again.
Brenda began riming him, poking his tongue inside his anus and tasting Danielle’s boi pussy. Then he fingered his pussy for a bit, which Danielle enjoyed. Eventually, he slid the butt plug inside, making Danielle squeal as it went into place.
“God, that feels huge,” Danielle said, touching his butt.
“Don’t be such a wimp. It’s only the small size,” Brenda said. “Wait until you graduate to the extra-large one that vibrates. Oh God, it’s heaven.”
“Do you have one in now?”
Brenda nodded, turned, and lowered his white satin panties to reveal the end of the butt plug nestled between his ass cheeks, a bejeweled end prominent. “Never leave home without it,” he said, repeatedly pulling his panties.
Danielle felt impressed. “So what’s next?”
Brenda took the flesh-toned dildo shaped like a real dick and stuck it onto the vanity, using the suction cup. The silicone/plastic cock sticks up in the air, five inches of pink glory.
Brenda announces in a high pitch, singsong voice, “Cocksucking practice.”
“Are you sure you’re not gay?” Danielle asked with a wry grin.
“I’m anything my mistress wants me to be,” Brenda said with his chest puffed out. “So, have you ever sucked a cock before?” Danielle blushed, and Brenda laughed. “Don’t sweat it. Most guys have. Especially, the small dick one’s like you,” he said, rolling his eyes. “OK, take a seat, and let’s begin.”
Danielle sat gingerly, feeling the butt plug inside him shift as his weight went on it. He had to admit the feeling seemed nice, so he wriggled around a bit to get the full effect. Brenda had recovered a small riding crop from the toy box and suddenly hit his hand with it.
“Ouch!” Danielle groaned.
“Stop messing about,” Brenda said sternly. “Now put your hands on the table, palm down, and don’t take them off until I say.” Danielle did as he was told. “We’re starting with deep-throat practice. Once you have mastered this, the rest is much easier.”
“This dildo looks pretty big,” Danielle said with a grimace.
“By the time you graduate, I expect you to be able to deep-throat ten inches without gagging,” he said. “But, as with the butt plug, we’ll start small and work our way up. Now, begin.”
“Small? This is not small.”
“Maybe compared to your clitty dick, no. But for a real man, this is small. Get to work.”
Danielle leaned forward, swallowed the fake phallus into his mouth, and let his spit run down it to coat it. As he began to bob his head, trying to take as much as he could into his mouth and throat, Danielle found after a few minutes. The teen could relax the back of his tongue, making the cock go deeper and deeper. He gagged a few times, especially at the start when he hadn’t worked out the trick to switching off his gag reflex. Saliva puddled on the vanity, and Brenda hit him with the riding crop. He remembered sucking off those two men in the toilet block at the beach.
“A good cocksucker doesn’t let anything escape his mouth. You’re not a whore in a porno movie,” Brenda shouted. “You keep those juices in your mouth; taste and savor him, for that’s the essence of manliness. Something YOU lack. Continue.”
The lesson goes on for a long time. Eventually, Danielle gets the whole five inches down his throat. The third time he gleefully took the entire phallus, Brenda grabbed his head and held it, not letting him get up. Danielle suddenly found it hard to breathe and struggled. However, despite Brenda’s sissy appearance, he’s surprisingly strong.
“Learn to breathe,” Brenda said. “Relax, you can do it,”
Danielle calmed himself and started breathing through his nose, and to his surprise, he found he could get air into his lungs. Brenda held him for ten minutes, urging him to suck, lick, and breathe. Eventually, he let Danielle go. The teen rose, leaving the phallus without any excess saliva on it.
Brenda stared at the dildo letting out a booming laugh. “I think you’re a natural at this,” he said, patting Danielle on the back.
“That’s what the guys I sucked said, too,” Danielle said with a knowing grin.
“Well, we only have about thirty-five minutes before Mistress expects us in the staff dining quarters, so we better move on to the next thing. I saved the easy one to last.”
“Oh?”
“Kissing, I need to assess your kissing skills,” Brenda said.
Danielle stood and took Brenda into his arms, and they kissed. Before long, their tongues were intertwined in a passionate mating dance inside each other’s mouths. They fell onto Danielle’s bed, humping their panties against each other as they kissed. Both have wanted to do this for a long time now, and the chance had arrived. Danielle didn’t even think he was French kissing a man. Brenda was a sissy, so he’s not a man.
That’s the mantra he lived by now. A sissy is not a man or woman. He’s gender-neutral. A female name will always address a sissy, but male pronouns are still used, not female ones. This keeps the sissy in the middle place between the sexes. Being gender neutral, as Danielle had learned, meant either true sexes could use him for their pleasure without feeling they’d be labeled gay or straight. A sissy never discriminated between the sexes, either. He took both with equal skill and enthusiasm. It’s always a sissy’s pleasure to serve.
Eventually, Brenda pushed Danielle off him and ran into the bathroom to wash his slimy little-caged cock. The last thing he needed was for Mistress to spot pre-cum stains on his panties. He’d be punished for such a faux pas, and as the senior sissy in the house, his punishments are worse as more is expected from him. Danielle followed and did the same.
“There’s nothing wrong with your kissing,” Brenda said, watching Danielle clean and dry his little caged dick. “But I’ll need to show you there’s more to it than just French kissing.”
“I think we needed that,” Danielle said.
“How big is it? Your dick, I mean. I’ve never had the chance to ask before.”
Danielle blushed. “Hard?”
Brenda nodded.
“Under three inches,” Danielle said and grimaced.
“I’m four, so don’t feel bad.”
Danielle suddenly smiled. “You know, I haven’t thought about it in three months now,” he said, puffing his chest out. “I used to obsess over my tiny dick. It was all I could think about.”
Brenda kissed him on the lips briefly to show his approval. “Come on, let’s fix our makeup and get out there. We don’t want to be late.”
*****
Later in the day, Mistress asked Danielle to wait in a small sitting room, which he did, wondering what her plans for him were. Feeling bored, he sat there for at least twenty minutes when the door opened, and his stepmom and stepsister came in. His face lit up as he recognized them, and he jumped to his feet and gave them both a huge hug and a kiss. The ladies returned his affection, then Laura held him at arm’s length and examined him.
“You’ve changed so much, Danny,” she said.
“Thank you, Mistress,” Danielle said with a blush.
Tina laughed at him. “Mistress? It’s MOM, you dope.”
Danielle bowed his head slightly to Tina and said, “All women are my mistress, for I am here to serve.”
Laura kissed him on the cheek and hugged him again. “Oh, Danny, Peta said you were progressing well, and I can see it. What a change?”
Tina guffaws loudly, making Laura and Danielle stare at her with raised eyebrows. “They’ve turned you into a fag, Danny. Look at you! You wear makeup, your hair and nails are pristine, and you have frilly pink panties. This is not the brother I know.”
“Tina, please—” Laura began.
“No, Mom,” Tina said, holding her hand up. “Sure, Danny was a wimpy, baby dick freak who jerked off ten times a day using our panties whenever possible. God, he was even stealing them from Mrs. Brooks’s clothesline. But at least he was our wimpy, panty-stealing, baby dick masturbation-addicted freak.”
Tears welled in Tina’s eyes, and Laura put her arm around her.
Danielle did too, and said, “Mistress Tina, I know my appearance seems strange to you right now, and you’re right. I’m not the same as when I first came home on spring break and we watched that horrible movie with the huge cocks. This is making me a better person. The boy you just described was out of control. He was going to end up on the sex offender’s registry.”
Tina shrugged. She’s uncertain these changes are for his good.
“I have grown a lot in this place,” Danielle continued. “I assure you when my training’s completed, you’ll come to appreciate your sissy brother more than the nasty freak you remember.”
Danielle motioned them to sit and left the room to prepare tea and cake, bringing it back in. Laura and Tina talk in anxious, hushed voices and stop as soon as he re-enters. The sissy served them and himself and grabbed a small chair so he could sit lower than them as a sign of respect. Danielle sat, feeling the butt plug move inside him. Laura smiled approvingly, knowing everything he did and why he did them.
Tina scowled and tried not to stare at this thing that was once her stepbrother. He sat and waited for Laura to take her tea and followed suit. The small talk rolled briefly as Danielle discussed their clothes, hair, makeup, and the latest celebrity gossip. Danielle did have one burning question that made his heart flutter, and he decided to risk punishment by asking.
“So, Mistress, where’s father today? Did he not want to see me?”
Laura glanced at the teacup she was holding. However, Tina saw this as an opportunity to upset Danielle.
“He didn’t wanna see his son acting like a fag. That’s why he’s not here,” Tina said coldly.
“TINA!” Laura said in a raised voice. “Go to the car and wait for me. I’ll deal with you later.”
Tina stood, and with hands on hips, she marched out of the sitting room, mumbling under her breath.
“Is it true?” Danielle asked, wide-eyed.
Laura paused to think about her answer. “Danielle, there’ll be many who don’t understand this life you’ve chosen. Most will assume the worst of you, I’m afraid,” she said softly.
“Mistress Mai had warned of this,” Danielle said with a lowered head. “So Father had chosen to disown me for being a sissy?”
Laura leaned over and took his hand, gazing into his eyes as warmly as possible. “As with Tina, he doesn’t understand, but when he sees what you’ll become, I’m sure he’ll change his mind. Give it time, OK?”
Danielle kept his head low, his hands trembling. “Do you approve, Mom?” he asked, looking into her eyes.
In a moment, both are in a deep embrace as tears run down their cheeks. “I’m so proud of you, Danielle,” Laura whispered in his ear. “Even in this short time, you’ve exceeded my wildest dreams. Keep going, believe in yourself and this life.”
“I will, Mom,” he said. “Thanks for believing in me.”
Suddenly the door opened, and Mistress Mai entered, making Danielle break from Laura and quickly use a tissue to dab his eyes. Laura and Danielle appear as two guilty children.
“I’ve been informed about a disturbance here,” Mai says strangely formally. “Is everything to your satisfaction, Laura?”
“Yes, mistress,” Laura said evenly. “My daughter was a little overwhelmed by the changes in Danielle and got upset. I’ll talk to her.”
“Are you overwhelmed by what Danielle is becoming?” Mai asked with a steely glare.
“Oh, no, mistress,” Laura said warmly. “I can see the flower budding and await eagerly when it blooms.”
Mai turned to Danielle and said, “The visit is over. Return to your room. I’ll call you when I need you.”
“Yes, mistress,” Danielle said, glancing briefly at Laura with a smile and nod.
The visitation ends.
*****
In the evening, his Mistress called him to her room and had him lean over her bed while she gave him ten smacks with a bamboo cane. The reason for his punishment, he’s told, is because he upset his sister.
“A good sissy knows how to please, not anger,” Mai said, leaving long red welts across his ass cheeks. She didn’t even bother to take the butt plug out. “What do you have to say for yourself?”
“I’m sorry, Mistress. Tina’s anger caught me by surprise. I’ll do better next time, I promise,” he said in a whiny voice.
Mai chuckled as she delivered the last blow. A resounding THWACK dominated the room for a moment. ‘His voice had changed so much,’ Mai thought. ‘The estrogen is transforming his body and his temperament.’ Mai examined his red bottom satisfactorily and ordered him to pull his panties up. Taking his hand, she led him to the cunnilingus chair, as he had come to call it. The only time she ever sat in this chair was when she wanted him to practice his technique, which for the last month had been only side-to-side over her clit. A method that hurt his tongue for a while. However, as time passed, his tongue grew used to it, and he had no problems.
Mai stood, wearing her riding pants and boots, and Danielle undid her pants, worked them off over her boots, and did the same for her purple panties. So she sat, spread her legs, and Danielle leaned in, again taking in her musky smell, and thus he began to sweep her clitoris side to side with his tongue. Mai leaned back and closed her eyes, enjoying how her clit throbbed each time his strong tongue swiped her.
After five minutes, she suddenly says firmly, “STOP.”
Danielle gazed at her rich brown oval eyes, his butt still throbbing in pain from the punishment he had just received.
“I’m tired of side to side,” Mai said evenly. “Tonight, I want you to suck my clit, as a baby sucks his mother’s teat. Give me your finger.”
He held his hand forward, and she took it, placing a finger in her warm, moist mouth. It made him shiver with lust. She sucked on it, yet not all sucks are the same. Her sucking feels like she’s playing a melody or a scale, with each suck offering a different intensity and force. After she did this for a while, she placed her finger in his mouth and told him to repeat it. Whenever he got the sequence or intensity wrong, she hit him with a riding crop on his leg, making the trainee sissy jump. Eventually, his method satisfied her, and she pulled her finger from his mouth and pointed to her clit.
Danielle knew what he had to do. So leaning between her legs again, he wrapped his lips around her clit and sucked the scale she had shown him. Again she leaned back into the chair, closing her eyes to feel her pleasure bud grow hard and pulsate through her body. Danielle enjoyed this method the most because he managed to get more of her juices into his mouth. Given that this session was occurring well into the evening, her pussy had an unwashed taste that made his needy caged dick throb. With his sucking and her moans growing louder, Mai suddenly orgasmed. Her body squirmed in the chair, and again she slammed her legs against his head in a vice-like grip, locking him in tight.
As he sensed her orgasm abating and in a moment of naughtiness, he switched to side-to-side. Only this time, he did it rapidly, flicking her clit the way she had shown him to do when she was getting close to orgasm. Mai’s eyes shoot open. However, before she could speak, another orgasm shook her body, making her squeal. Once she started her second orgasm, he returned to sucking, waiting for her to finish.
Then he repeats the process three more times, making Mai orgasm each time. Holding her in an extreme orgasmic pattern, for the first time, Danielle felt the power a sissy had. There’s power in giving extreme pleasure because you also could deny it. Once someone had tasted the forbidden fruit of intense orgasm, they’d do anything to experience it repeatedly.
Mai lay slumped in her chair, no longer the stiff posture of the woman in control. Her usually straight, long hair was all messed up, and her face was sweating. So Danielle stood, went to her bathroom, and ran the bath, lighting her favorite scent candles. He returned with her treasured silver and ivory brush and gently fixed her hair. Then the sissy gently undresses her, carefully folds her clothes the way she likes, and puts them away. Last, he picked her up in his arms and took her to the bathroom, lowering her into the warm water, being careful not to wet her hair.
Turning the spa on, he grabs a cloth and washes her gently. Mai eventually opens her eyes, stares into his, and sees tender love. Danielle sees the same returned for the briefest of moments.
“You can go to bed now. I’ll finish from here,” Mai said, trying to sound formal but failing.
“Yes, mistress,” Danielle said and went to bed.
*****
His reward for bringing Mistress to intense multiple orgasms included new lingerie, an Armani navy blue striped wool suit, and a light blue cotton shirt. He excitedly jumped as he examined his new clothes and immediately went about getting dressed. So with hair and makeup done and standing in his gorgeous suit, he stood at his Mistress’s door, waiting for it to open. Mai scrutinized him and nodded her approval, and Danielle thought the months of workouts with Brenda had paid off. Danielle had never looked this good in his life.
After his morning duties attending to Mistress Mai finished, Brenda took him into town to a spa. Danielle feels excited about a few hours of pampering when Brenda announces, “Sorry, Danielle, we’re not going to get pampered but to do the pampering.”
“What?” Danielle said, fluttering his dark eyelashes quickly. “But this suit? I thought—”
“Oh, the suit is a good thing,” Brenda giggled. “You must’ve pleased Mistress Mai to get that.”
The way Brenda glanced at him, Danielle knew he wanted the gossip. Danielle didn’t say a word as he knew part of being a sissy is keeping quiet about what happens in the privacy of the bedroom. Brenda gave up trying to pressure Danielle into telling him what happened and decided to keep talking about the spa.
“Anyway, you’re here to learn massage. Sensual massage in particular, because our mistresses love it before having sex with a bull,” Brenda said.
“I know how to do sensual massage,” Danielle said with a huff. “Mistress made me read every book and watch every DVD about it. God, I’ve massaged her to orgasm several times.”
“Oh, don’t brag,” Brenda said, rolling his eyes. “Today is a test. Sure, you can make Mistress feel nice because you’re comfortable around her and know her body.”
“So what?”
“So, today, you’ll use those skills on strangers. Women you don’t know, or maybe you don’t feel attracted to.”
“Why would Mistress want me to do that?” Danielle asked wide-eyed.
Brenda sighed deeply. “God, you’re slow,” he said. “A mistress may order you to serve anyone she wants, regardless of your feelings toward that person. Man or woman. Young or old. Attractive or ugly. Fat or thin. Our job is to obey and do what Mistress wants. Get it?”
“I only want to serve Mistress,” Danielle pouted.
Brenda laughed wickedly.
“What?” Danielle asked.
“You’re at that stage, eh?” Brenda said and smiled. “We all fall in love with our first Mistress at some point. It’s normal. She knows it too, and that’s why you’re ready for the next and final phase of your training.”
“Oh?”
Brenda smiled, his eyes sparkling. “She’s going to use the love you feel for her to break you and turn you into a total submissive slut.”
Danielle didn’t know how to react to the news. Given what he had endured so far, he thought she had already done that. However, maybe Brenda had a point. Perhaps this willful disobedience he’s feeling about massaging strangers all day is a sign that some of his old independence remained. He doesn’t want to think about it anymore, and as Brenda parked behind the spa, he steeled himself for a grueling day ahead. Massage may be pleasurable for the receiver, but it could be hard, repetitive work for the giver.
This eBook contains The Stepmother 1 & The Stepmother 2
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*This eBook contains adults-only taboo erotica. All human characters in this story involved in any sexual behavior or acts are over eighteen. Any similarities to real people or real-life situations are purely coincidental and unintended. This eBook is 100% fiction, none of this ever happened in real life. The taboo themes of this story are fine for sexual fantasy, but only a fool would do them in real life. Do not try this at home. This disclaimer voids GW Enterprises Publishing Company against any claim that our stories have been a motivation for criminal activity. You are responsible for your actions. Thank you for reading this free sample.