The Training of Cecelia Ch. 02

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Proud woman discovers the joys of submitting to anal sex.
11.3k words
4.74
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Part 2 of the 5 part series

Updated 09/14/2023
Created 05/23/2021
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Summary: Proud woman discovers the joys of submitting to anal sex.

Note 1: Thanks to TigerSir for suggesting this novella and many of its themes, and for pushing my limits a little.

Note 2: Thanks to Tex Beethoven and TigerSir for editing this ambitious story.

Note 3: This is part two of what I'm certain will become a lengthy novella. (Including this installment, it's already slightly more than 37,000 words long, and once it reaches 50,000, which appears more than likely, it will qualify as a short novel.) Also, although it contains a lot of typical silkstockingslover themes, this one digs deeper into BDSM than I usually go.

In part one Cecelia, a CEO with a major ego, is put in her place by a company fixer who sees past her strong-willed female persona to her natural submissive nature, and he begins training her to be a completely submissive slut.

And now... the morning after her complete submission... or what she had thought was her complete submission....

The Training of Cecelia Ch. 2

The next morning: Sunday

I woke up feeling completely refreshed... I opened my eyes, and only then realized I hadn't slept in my own bed.

Then last night came flooding back to me.

I'd willingly cheated on my husband.

I'd allowed another man's cock into my mouth and my pussy.

I'd allowed another man to come on my face.

I'd allowed another man to fill my unprotected womb with his seed at a time when I was at my most fertile. He might have gotten me pregnant, and I absolutely hadn't cared! (Strangely, I still didn't.)

I'd allowed another man to tie me up, thus rendering me completely helpless.

Fuck!

I should have felt guilty of course, yet oddly, I didn't.

Instead, I felt liberated.

Instead, I felt alive.

Instead, I craved even more.

I rolled out of the bed... alone... wondering where he was... likely upstairs somewhere, since I was in the basement of his house... wondering what time it was.

I got up and stretched. I felt surprisingly refreshed after a night of such extremes of sexual debauchery. I didn't feel tired at all. I went to the phone in my purse and saw twelve messages from my husband. I read them all, and only the last three expressed some concern about my welfare.

I called him. "Hey," I said. "I'm alive."

"I was worried."

"I just needed a day without electronics," I said, which except for the vibrating toy, was actually the truth. "Sorry, I should have told you I was taking a technology break."

"Good for you," he said, having told me many times I lived far too much on my devices. Always having them on, responding to text messages and such at all hours of the day or night, including when we were out to dinner, or even during social gatherings.

"Yeah, I figured you'd appreciate it," I said, although my tone conveyed a slight hint of annoyance at his patronizing response.

"Woah. I didn't mean that in any way except 'Good for you'," he clarified.

Sure, he meant well; and he certainly wasn't trying to start a fight. But I was, so I said belligerently, "I know what you meant."

"Honey, I didn't mean anything at all," he attempted to backpedal, immediately on the defensive. Which was a position I put him into a lot, I realized.

"Sorry," I apologized, as I realized I was only trying to start a fight so I'd feel less guilty about cheating on him. "I'm feeling just a little sensitive," which was true; my pussy felt raw from last night's overuse.

"No worries," he said. "How was it to unplug and just let go of the rest of the world?"

"Amazing," I said, conscious of still telling him the absolute truth, even while misleading him. "Liberating, even."

"I said that you would," he said, again not deliberately attempting to start a fight, but oblivious to his own smarminess... he was who he was.

"Yeah," I said, ignoring his stereotypical 'I told you so', and instead saying, "It felt liberating just to let go." I stopped short of adding '...and to give free rein to my carnal lust'.

"That's great," he said, oblivious to what he was calling 'great'.

"Yes, it was amazing," I said, really enjoying telling him something scandalous, while he thought I was saying something far more innocent. "Literally life-changing."

"Awesome," he said. "Well, I hate to cut this short, but I'm attending a breakfast meeting."

"Sounds good," I said. "I need to go get some breakfast myself."

"Love you," he said.

"I love you too," I said automatically, now feeling slightly guiltier, although still not very much. I did love him. I really did. Just not with any passion anymore, and recently I'd realized I needed a lot more than just vanilla love.

We hung up, and after going to the washroom, I looked around for my dress, since I was wearing only the garter belt and stockings I'd worn beneath it last night. Not finding it, I shrugged and walked upstairs to where I assumed the kitchen would be. (The previous evening when I'd arrived, I'd been so preoccupied with other matters I hadn't noticed whether Paul's house even had a kitchen!)

To my surprise, he was already up.

To my further surprise, he was sitting at the kitchen table reading an actual printed newspaper! Who still does that in 2021?

And next to my astonishment, he had a woman wearing a maid's outfit kneeling under the table sucking his cock!

He didn't look up, as he said casually as if there wasn't an elephant in the kitchen sucking his dick, the dick I wanted to suck, the dick I'd been hoping would be my breakfast, "There's a full breakfast ready for you in the dining room. Be sure to fill yourself up, because you have a busy day ahead."

"Yes, Master," I said submissively, secretly glaring at the brunette under the table who was bobbing slowly on his penile masterpiece... jealousy and envy coursing through me.

I went into the next room, where a very nice spread was indeed laid out. I dished up some pancakes, some sausage (not the sausage I was craving), some bacon and some toast. It was only with the amazing aromas and food before me that I suddenly realized how hungry I was... all I'd eaten last night was some cum, and nowhere near enough of that... not for nourishment, anyway.

I returned to the table and sat down across from him. As I began eating, he asked, "How was your sleep?"

"Surprisingly refreshing," I reported.

"Why surprisingly?" he asked, finally looking up at me for the first time since I'd arrived upstairs.

"I don't normally sleep very well," I explained. "I tend to be a restless sleeper."

"That's because normally you're constantly thinking about work and never letting yourself go," he said, or more like lectured (but just pedantically, not browbeating me at all).

"I suppose," I responded as I ate some bacon. He was likely right. I was usually either working or thinking about work every waking moment of my day, regardless of where I was. But last night, from the moment I'd wandered curiously into his sex room, my work brain had vanished... I hadn't thought about work at all!

"Oh, there's no I suppose," he refuted. "I know what I'm talking about."

"Yes, Master," I said, loving his strong confidence and knowledgeable persona.

"You do know it's almost eleven?" he enquired.

"What? No way!" I gasped, having not even glanced at the time when I checked my phone, preoccupied with my husband's texts. "I never sleep in that late!"

"That's the freedom granted by your ultimate submission," he explained.

"I guess so," I laughed. "I can't believe it's eleven already." By now I would normally have worked out, read the news (on my iPad of course, not an actual newspaper), eaten breakfast, showered, and would likely be on my computer working, even though it was a Sunday.

"One thing about submission and surrendering your control completely, is the astonishing tranquility resulting from unthinking obedience," he said. "Or less wordily, once you let me do all your thinking, you're free."

"I hadn't thought of that," I admitted, not sure it could possibly be that simple, and yet I did feel a tranquility I was far from accustomed to... a relaxed morning, even on a weekend, wasn't something I normally experienced.

"Ah, but as of last night, it's no longer your job to think when we are together," he said, as if I should have remembered, which hurt just a bit, even though I vaguely remembered hearing him say something like that last night. "From now on, I'll be doing all your thinking for you. At least whenever you aren't working."

"Yes, Master," I obeyed, happy he'd included the addendum. What he was saying was that he saw me as his submissive slut whenever we weren't at work, but he still respected me as a career woman with a head on her shoulders whenever we were in the workplace... which was exactly the kind of relationship I'd been secretly fantasizing about, and even longing for, for many years.

"Good. Now once you've finished eating, and no big hurry, you may help yourself to seconds if you like, then you may go shower, second room on the right down that hallway," he pointed, "and then go to the next room on the right, the third one, and put on the attire I've arranged to be left for you on the bed," he instructed. And then he groaned, and from his expression, he'd just unloaded his morning load into the maid's mouth.

And pitifully, all I could think was, Why not my mouth? Which served me right I suppose; he'd warned me not to think.

"Yes, Master," I replied, still finding just mindlessly obeying his instructions not only as natural as breathing, but also completely liberating.

"Good," he said. "Barbie, you may come out now, and stand up."

"Yes, Master," she obeyed. A moment later, she was standing before me with a couple drops of his cum still on her lips, which she soon licked clean.

"Barbie, this is Seesee; Seesee, this is Barbie," he introduced.

I did a double take! It couldn't be! But it was! My eyes went wide! I knew this woman! Fuck, everyone knew her! She was a Senator from our state of Massachusetts. She was a role model for all women. She would possibly become the first woman U.S. President. Although her name wasn't Barbie, never Barbie, it was always Barbara. Except when you weren't addressing her as 'The Honorable Senator Brown'.

"It's pleasant to meet you, Seesee," she greeted me graciously. After she'd given me a thorough and approving look up and down my body, she thereafter ignored my almost total nudity, apparently viewing it as an inconsequential (but pleasant) detail of my presence here.

"Actually, we met a couple years ago at a fundraiser for women in need," I mentioned, in awe of the personage standing in front of me, and doing my best to act as if I weren't virtually naked.

"I'm sorry for not remembering," she apologized, apparently sincere.

"Please don't be," I hastened to reply. "I can only imagine the number of people you must meet on any given day."

Paul cautioned, "Now it goes without saying that whomever you meet, and whatever you witness in my house, is all one hundred percent confidential."

"Absolutely!" I agreed wholeheartedly, with so many questions swarming around inside me. But the main one was simply: how on earth had Barbara Brown, such a well-known politician and internationally respected feminist, ended up under a table wearing a maid's outfit, sucking Paul's cock and swallowing his cum? "But... Seesee? Really?"

"If the honorable Senator here can tolerate being called Barbie, I don't think it unreasonable for me to trivialize your name as well." Then addressing the cock sucking Senator, "Do you object to my calling you Barbie, your honor?"

"You know I don't, Master," she replied with a saucy grin.

"Then Seesee, it's settled. Barbie will help you to orient yourself after you've showered."

After she walked away with impeccable dignity, managing to do so wearing six inch heels, impractical for any woman under any circumstances, he said, clearly reading my mind like he always did, "Like I said, many strong women are searching for a man who can sexually put them in the place they crave."

"She's married, you know," I pointed out, although my own marriage obviously hadn't stopped me from handing over my reins to him.

"So?" he asked.

"Just saying," I said.

"Most of my pets are married; they're just never sexually satisfied until they've joined my "chosen family"," he said.

"Have you fucked her husband?" I asked, recalling his telling me he planned to fuck mine, and Barbara's husband was a nationally prominent businessman.

"I cuckold every husband of every woman I train," he said, not directly answering the question, but nevertheless conveying the answer. "Now go shower. We need to begin your Day Two's training."

"Yes, Master," I said, as he left the room and I headed to the bathroom.

I took a long, not quite scalding hot shower... cleansing myself of sin, while prepping myself for more sinning.

I got out, wrapped a towel around myself and went into the bedroom, where I found only a pair of white thigh high stockings and a white leather collar placed neatly on the bed. No panties. No bra. Not even any lingerie. The collar had a small metal ring for attaching a leash. I understood immediately that today would be an entirely new level of submission, compared to last night's.

I sat on the edge of the bed and slid on the silky sheer stockings... which were easily the softest, sheerest, silk stockings I'd ever worn.

"You look good in those," Barbara observed, slipping unobtrusively into the room.

"T-t-thanks," I said, in awe of still being almost naked with this woman I admired so much. I knew she was almost sixty, but she didn't look anywhere near that age.

"I see you're Master's newest recruit," she said in a friendly way, coming over to me, carrying a white leather leash in her left hand.

"So it would seem," I said, part of me ashamed to be seen in such a humiliating situation, yet the knowledge that she'd obviously once been precisely where I was now during her own journey, made it far less so.

"Don't be too concerned about what you're about to experience," she said reassuringly. "Even though it will be unbelievably challenging at first, once you give in to Master completely, you'll experience levels of freedom and pleasure you can't even imagine right now ."

"Do you feel that way now?" I asked, as she attached the leash to my collar.

"It took me some time, and some intense struggling against myself to get there," she explained openly and warmly, rather like we were sisters in arms. Except that she already knew the terrain lying ahead of me extremely well, while I couldn't even imagine it yet. "Like you're experiencing right now I suspect, I went back and forth between two extremes. Thrilling to my ultimate submission and often even exulting at times, but attempting to cope with my ultimate shame and guilt at other times. Can you relate?"

"Yes and yes," I said, this intimate conversation really buttressing my feelings. I had a difficult road ahead, but she had every confidence I'd eventually make my way along it, just like she herself had done. "But I'm hoping the other side is different?"

"Well, I'm not promising you'll ever feel totally guilt free, or at least not until your husband submits too, but the emancipating emotions of your submission, combined with the variety of pleasures you'll experience almost every step of the way, will usually override most of the guilt," she predicted.

"That's how I felt last night," I admitted.

"I'm glad," she said. "You're very pretty," she added, as she leaned in and kissed me. Not passionately at all, but warmly, reassuringly.

I felt wetness gush out of my pussy the moment her lips contacted mine while I mindlessly returned her kiss, in awe of whom I was kissing.

When she broke the kiss, she offered, "I'd love for you to come by my home for a visit sometime."

"Really?" I asked.

"Yes," she nodded. "I can promise you'll have the time of your life."

"I can imagine," I smiled.

"You see, I may be a submissive to Master, but I'm also Mistress to a number of submissive women," she said, a single finger gliding back and forth across the sensitive flesh between my bare breasts.

"I'd become your pet without any hesitation," I replied, literally trembling with excitement at the possibility.

"I know you would," she said, her finger slowly slithering down towards my fevered pussy. Just as a finger of her other hand was almost touching her own pussy underneath her black, extremely short skirt.

"Ohhhhhhhh," I moaned, without her finger even touching my core.

"Oh, would I love to fuck you right here and now, you pretty thing," she sighed, "but Master has given me very clear instructions."

Her hand moved completely away from me, and she tugged gently on my leash.

Understanding her silent instruction, I lowered myself first to my knees, and then onto all fours, symbolically becoming her pet. Or perhaps she was only serving as my pet sitter until delivering me to Paul.

"Follow me," she said, and I did, wetness leaking out of me, as I followed this submissive/maid/Mistress/feminist/Senator, like a bitch in heat.

"Yes, Mistress," I replied, the idea of perhaps ending up between the legs of someone as powerful and inspiring as Barbara was a major rush.

She didn't say anything, but I thought she might be smiling as she led me back down the hallway, awkwardly (me, not her) downstairs to the basement, and back to the scene of last night's criminal activity. (Not literally of course, it only felt like it.)

"Climb onto the bed," she instructed.

"Yes, Mistress," I said, doing as she instructed.

"Are you already stealing my new pet before I even get her trained?" Paul asked unexpectedly. I hadn't noticed him when I crawled in... since I was focused on the incredible legs of the amazing women who'd taken me for a walk. (I know, Woof! But this could be you someday, if you're extremely lucky!)

"Steal isn't the right word," Barbara said. "Borrow, I think is a better descriptor."

"She's quite a catch, with many possibilities," Paul said.

"Her possibilities are endless," Barbara agreed, "eventually anyway, but not just yet, at least not for me," as she stroked her hand enticingly over my ass.

"I'll see you when you return next week, slut," Paul said, obviously dismissing her.

"Yes, Master," Barbara said, sounding a little disappointed, just like I was. "It was nice meeting you, Seesee. Enjoy your training."

"Thanks," I said, wondering how soon I'd be able to become her pet too. But taking a step back from the thought, I couldn't help but shake my head at just what I was thinking. How quickly I'd shifted from a no-nonsense boss all my employees feared, to... to... whatever I was now.

"Don't worry," he said. "You'll get to play with Barbie someday."

"I truly hope so," I said, hoping she heard that, but I was facing the other way, and wasn't even sure she was still in the room.

"Oh, I guarantee that you will," she replied, still nearby and sending a real thrill through me! "But for now, I have a flight to catch."

"Bye, slut," Paul said, and hearing Paul addressing someone as prominent as Barbara with that slur was simply surreal!

"Bye, Master," she said.

"So are you ready for Day Two of your training?" he asked me.

"Yes, Master," I answered with some trepidation, but still willingly enough.

"Today's training will be more intense than last night's."

"That I can't fathom," I said, recalling how intense everything had gotten last night.