He is Your Master Now Pt. 09

"Oh sweety, quitting is an exception. It's the component that tests if you can free yourself from Cassilda. It's my job to train you not to make sure you didn't get it in your head to have a hissy fit until they let you go. Training subjects is job enough."

Ambrose thought he had her, but her answer was delivered so quickly and in a practiced manner, that he believed her. He continued to pout on the verge of tears as the anguish he felt was too strong to completely suppress his emotions.

"I can leave for a few minutes if you need to be alone to regain your composure. Would you prefer that? There'd be no repercussions if that's what you want and if you're not up for an outing today, we can do it tomorrow. But personally, I think you need to get out of here for the day.

"Do you want me to give you a moment?"

With her warm, soft hands still on his face, Ambrose slowly shook his head no.

"Do you still want to go out today?"

He nodded yes.

Pippi pulled him in close and gave him a tight hug. She soothed the back of his head as they each rested their chins on the other's shoulders.

When she figured that enough time had passed, she pulled away and addressed him.

"Ok. All better then," she said. "So we're going out, but you're probably wondering why you had to be prepped."

"I forgot about that," he said, still somewhat gloomy.

"We're going to plug you early today. And it's going to be one we never used before."

"So--- I'll have a butt plug in me the entire time we're out," he said flatly.

That's right.

"And--- I'm guessing I won't be wearing men's clothing." He said nervously.

"Occasionally, Cassilda will want to have a 'girl's night out' with just the two of you. Remember, this is all for Cassilda. It's better that you start dolling up in public during the day because I find it's more effective for my students to feel exposed right from the start because they get over it surprisingly quickly."

He just knew there'd have to be some awful condition to this outing; wearing women's clothing and sporting a butt plug were it. He just hoped there were no other surprises.

She went on to explain that at night, her students kept experiencing an uncomfortable cycle of hope that they'd walk into dimly lit or dark areas for the cover, and then anxiety when they walked into well-lit areas.

"Except for the movie theater, we'll be in well-lit areas today. You're probably going to feel awkward as hell, but, like I said, you'll get over it much quicker than you would have at night."

"And I have no choice but to do this." He said dejected.

"I told you; you always have a choice. And now you know that you'll be given the clothes you came here with, and all your personal belongings and you'll be supported for months."

"But I'll lose Cassilda forever."

"That's the cost. Now you have to imagine both options sitting on a balance scale. Which one has more weight?

"Correct."

Pippi was right. He was weak. He took in a deep breath, closed his eyes and breathed out slowly. "I'll do it."

Pippi was exceedingly pleased. "Awesome. I'm so glad you said that because I have another pleasant surprise for you. You'll get it before we leave."

"What is it?"

"You'll see." Pippi got the new butt plug, which appeared to have chrome like plating, it was also rather large. It was the largest one yet. Pippi ran it under warm water and handed it to him for examination.

The first thing he noticed was that it was heavy. Its heft was so unexpected that he nearly dropped it. It wasn't chrome covered plastic after all, it was stainless steel and solid all the way through. That's why she ran warm water over it; to warm it up. By contrast, all of his other butt plugs were made of light materials or much smaller if they were metallic. Where it not for the fact that it was a sex toy, it could have been used as a paperweight at a news stand in Tornado Alley.

He was now experienced enough to know that it was going to be difficult to push it into him. But it was the bottom portion of the plug that really troubled him. It wasn't as rounded as all the others he had sported, and the stem between the plug and the cap at the base was dramatically thinner. Taking it out was going to be worse than putting it in. In fact, he might not even be able to pull it out himself. At least not easily.

He turned it over to inspect the base. He had expected to see an expensive jewel, or a broach like cameo or such other kind of art. What he found instead was an enamel picture of some cutesy, Japanese-style, cartoon bunny with an extremely happy expression. Somewhat humiliated, his skin flushed a little.

"We didn't design it. It was a custom-made job for someone else and they cancelled the order after it was made. They had only left a down payment, but even so, we got it for nothing because we're good customers. Not that we couldn't afford it. You're the first to use it.

"Now let's get you plugged up," said Pippi, ignoring his distress. She could still be cold sometimes when Ambrose was upset about something she saw as trivial, and she didn't want to spend the energy explaining things to him or to sooth him.

"You know the drill. On the table"

Absentmindedly, Ambrose got on the table face down and ass up with his knees positioned slightly apart. He put his hands behind him and held his ass cheeks apart, exposing his anus.

He heard the by now familiar tube fart noises as Pippi squeezed a copious amount of lubricant directly on to his asshole. For the first time, the lube was at a comfortable temperature rather than cold. Ambrose suspected that this was a small kindness paid to him to make up for the butt plug's mass.

She worked a finger into him and gently massaged his anus in ever widening circles to get it to relax. She stuck in a second finger and continued her ministrations, but she took longer than normal and also spread her fingers wider. This worried him as it illustrated just how difficult inserting this butt plug was going to be. She inserted a third finger. She had ever done that before. His anxiety increased. Then with two fingers, she held his asshole open and with her other hand squeezed more lube directly into the gape.

She worked it in vigorously.

He then heard her apply the lube to the butt plug.

"Ok. I'm going to count to three and then start working it in. But I'm going to go really slow--- but as always, you need to relax back here. We can take as long as you need, but this has to get done.

"One............ Two............ Three............"

She began working it in, alternately swirling and rotating it.

At first everything was normal, but soon it reached the point where Ambrose began to feel discomfort. From there it became exceedingly painful.

He imagined his asshole breaking like a rubber band, but instead of flying across the room, it would just unleash a torrent of blood. He'd die from blood loss--- out of his ass.

"Oh shit. I don't think I can do this."

"Nonsense. You can do it. I have a feel for these things and you being my best student ever, you need to have as much faith in yourself as I have in you."

"Ughhhhhhhhhh" he grimaced. He wanted to squirm but managed to exercise enough control to avoid it.

Suddenly, he jerked when the bulb passed through, causing his asshole to snap around the stem.

"You see, that wasn't so bad."

It actually was. Quite some time passed before the throbbing even began to subside.

"Whatever you do, don't hop down, get on the floor slowly."

She didn't really have to tell him not to hop or step down slowly; the feel of the big hunk of metal was telling him that.

She had to steady him as his knees trembled and threatened to buckle. When she was sure that he was steady, she told him to walk around.

He walked awkwardly as with each step he could feel the uncomfortable hunk of unyielding steel move within him. It was too big to feel like a turd threatening to come out, as had some of the others at first, until he got used to them.

"I don't think I can walk all day with this up my ass," he said worriedly.

"Honestly, for a while, you're going to be aware of it most of the time you move, but you'll become more accustomed to it as the day goes by. Now get back on the table slowly, again. Remember, don't hop, and sit close to the edge."

He felt uncomfortable pressure from the intrusive object as he sat. But still---.

"I promised you a treat. Are you ready?"

Ambrose felt he was being set up for some slight unpleasantness but answered in the affirmative.

Pippi began rubbing his lap and knees erotically. Ambrose could hardly believe what was happening until she parted his knee and produced the key to his cock cage and unlocked, setting it aside on the table. Before his liberated little pecker could get fully hard, she leaned down and planted a little kiss on it.

She looked up at him slyly.

"I want you to wiggle and gyrate your ass while I go down on you."

He did as he was told and suddenly, the invasive object didn't seem so bad.

Ambrose swooned as Pippi darted her tongue all over the tiny pecker and licked his balls.

All the while, he kept alternately wiggling and gyrating his ass. The feel of the butt plug competed with Pippi's expert technique. She engulfed him entirely in her mouth while managing to lick his balls in the process. He groaned in response, closed his eyes, and began breathing harder.

Damn, she was really good at cocksucking.

When Cassilda penetrated him, he'd have to wait until she came before he was allowed to cum. But between the chunk of metal in his ass and Pippi's earth shattering blowjob, Ambrose' subconscious began the process of associating the stimulation of his ass with sexual fulfillment.

He began gyrating more excitedly and tried to hold out but just couldn't. When it seemed that he was about cum, Pippi attacked his cock head with her tongue, all while keeping it and his balls entirely in her mouth. She licked hard against the head, making sure that Ambrose really felt it.

"HOLY--- " exclaimed as the cum squirted in her mouth.

The volume was not as copious as sex with Cassilda, but it was rather a lot and the force of his ejaculation was much greater than with anyone else. It was also of a different quality that he would later struggle to define.

Pippi took in squirt after squirt. When she was done, she stood up, pulled his head down and invaded his mouth with her tongue. She had yet to swallow any of his cum but he didn't care at all.

They alternately kept making out, swallowing and licking his cum off each other's lips and chins until it was all gone.

She pulled away. "I saved it to share with you." She said it as if it was a treat for him, which kind of worked as it was so soon after he came. He was even unaware of the butt plug at that moment.

"Some men don't like the idea of tasting their own cum. But I believe that when you share their own cum with them in a passionate kiss, there's a bonding that takes place, whether they're consciously aware of it or not. Your cum was a gift. Me sharing it with you was also a gift. I don't do that with everyone. At the very least, we will always be friends because we shared your gift."

What she said was ridiculous but the sincerity on her face was unmistakable. It was touching to the point where he found it a little hard to breathe.

"Ok. Let's get you all dolled up and ready to leave."

She got down to business right away but in a more relaxed manner.

"We need to make you sexy, but not night club sexy because it's daytime after all."