Kate Educates Jacob #22
Tiffany's progress
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“It sounds like you’ve turned a corner, Tiffany, and I’d like you to share that with me.”
When Kate secretly unzipped my jeans, I froze in absolute horror, almost choking on a mouthful of wine. She gently undid the button on my boxer briefs and my cock sprang out, ready for action.
Kate stroked my shaft lovingly, leaned over and then kissed me on my cheek. She stared at me with a seriousness that was disconcerting, as though denying the cock she gripped tightly was real.
“I’m just having a private chat with Tiffany if that’s okay, honey.”
Without waiting for an answer, she turned back to Catherine’s new submissive slut and began gently wanking me under the table, giving nothing away to our fellow diners.
Tiffany shot a look toward Catherine, who smiled and nodded her permission to continue.
“I stood up from where your mother was brushing my hair and asked how she could help me. Mistress explained that if I wanted to drop the guilt, I needed to confess it, take a punishment, and then receive forgiveness before moving on. She swished the hand brush around and my blood ran cold because I knew then that Mistress meant to spank me.”
Tiffany looked excited to share her first time experience, sipping more wine before continuing. Catherine and Claire were engrossed in a discussion about horses at the opposite end of the table and Kate wanked me off smoothly but firmly while I feigned admiration for a wall painting opposite. The young woman serving dinner stood a discreet distance away and seemed bored, waiting for a diner to request a refill.
“Your mother told me to pirouette so that she could inspect me. She said I was beautiful in body and now in soul and then she lifted my negligee almost to my breasts. I felt exposed and frightened, but very turned on.”
Kate gripped my cock harder, pulled my foreskin backwards as far as she could, held it there for a few seconds, then stroked me forwards again. She appeared totally attentive to Tiffany, who had no clue that the cock she’s craved so badly was getting off on her story.
“She gently and slowly pulled my panties down, using her thumbs in the waistband. I was moist down below, and she noticed, complimenting me on the flavour.”
“The flavour?”
Kate sounded a little surprised and almost jerked my cock off.
“Um, yes… your mother dipped a finger, maybe two, inside my pussy, smelled me, and then licked them clean. I almost collapsed into an orgasmic heap.”
“Did you enjoy that?”
Kate wanked me a little faster, while blocking Tiffany’s view by leaning forward.
“Very much, and I asked her for more. She stroked my backside, slapped it a little and asked if I enjoyed that, too.”
“Did you?”
“Is it okay for me to explain all of this to you, Kate?”
“Yes, now answer the question.”
“I loved it, so she brought her knees together and told me to bend over her lap from the side. It took me a little while to get comfortable.”
My cock was going to explode soon, and I coughed so she’d know. Kate didn’t blink.
“Jacob, please clean that ketchup stain in front of you with your napkin, or it will become a problem in the laundry.”
I picked up the white napkin and gave the stain a cursory wipe, but I knew Kate meant for me to keep the white linen in hand to clean a different mess soon. Tiffany took another gulp of her wine and was about to reach a crescendo.
“It turned me on and your mother knew it, so for a while she stroked my back, ass cheeks and thighs. Then she spread my legs apart, exposing my pussy a little before fingering it, explaining that I needed to be very aroused before she could lay into me.”
Tiffany stopped and glanced at Catherine, who nodded for her to continue. The woman who’d been my nemesis turned back to Kate looking demure, peaceful and contented.
“Go on Tiffany.”
“I know she tasted me a few times while flicking my clitoris and strumming my labia, and that drove me wild. Mistress was so gentle with me and I didn’t want her to stop.”
“But she stopped, right?”
“Just before I came, yes, it was like she had a radar that knew when I was about to orgasm. That’s when she thrashed me. I felt the hand brush swish just before it hit the first time. It stung like an electric shock.”
I was going to cum any second, and Kate knew it. She wasn’t edging me or going for a ruined orgasm. My girlfriend was taking me all the way.
“Did you enjoy it?”
“My backside was on fire and I wasn’t sure I could take another one. I wriggled, so my Mistress lifted one leg and trapped both of mine under it so that I couldn’t move. She asked if I wanted another, I said I did, and then she beat me, counting every one to twenty. At first it killed me, but gradually I drifted off. You know what I mean?”
“Kinda, I hear that’s what happens.”
“She told me that when she reached fifty, I must let my guilt be released and move on, but she also explained it would get more painful as she went along. Then she laid into me, spanking both butt cheeks, going at each one with perfectly spaced timing. When she got to fifty, I orgasmed, making a mess of your mother’s lap because I squirted. I’ve never done that before, Kate.”
Kate pulled one more time on my cock and held my foreskin back while I emptied my seed. I covered the napkin over the top of my glans while a torrent of semen flooded into the neat linen folds, soaking them. My balls twitched, and I shifted in my chair to cover up each spurt that launched through my cock, saturating the square cloth.
I looked guiltily at Catherine, who smiled and winked at me. I wondered if she’d guessed I was being wanked off, and felt terrified that she might expose me.
“Did you cum again?”
I froze in terror, about to answer, until I realised the question wasn’t for me.
“Not right then. Your mother told me I was forgiven and should mention no indiscretion again.”
“Was that the end of it?”
“No, she told me I should take care of myself but that she’d get me started, so she inserted the hand brush handle into my pussy as deep as it would go. I felt really full, and squeezed with all my might, trying to crush the wood. Your mother fucked me so gently with the wooden brush I felt as though I was in heaven.”
“Did she finish you?”
“No, she said it wouldn’t be right for her to do that so soon and I should think things through. Just before I was about to explode, my Mistress stopped, sucked the handle and then handed it to me. She kissed me on the forehead, said goodnight and told me I had her permission to continue by myself.”
“Did you?”
“Yes, after she closed my door, I just went for it. A few times through the night, to be honest. I have to confess, Kate, I really wanted your mother to do it for me and stay the night.”
“Tiffany, I’m thrilled for you. It sounds like you found absolution and happiness. I’m sure things with my mother will progress however you two decide is best.”
“I really enjoyed the entire week, Kate, and it’s all thanks to you. Would it be inappropriate for me to ask if I can stay here for a while, please? I can work around the place to pay my way.”
“Of course you can stay, as long as you keep working at the program Mistress Granger has set for you. Don’t worry about employment. I have a new job for you, something we can discuss in the next few days.”
Kate smiled at Tiffany, then glanced at her mother, nodding appreciatively while raising her glass in a salute. Catherine returned the gesture.
I tucked myself away, scrutinizing everyone carefully to catch any sign that they knew what Kate had done for me. They were oblivious, and I settled down, comfortably and deeply satisfied. My girlfriend cuddled across to me, moving her dining chair closer.
“Was that good, baby?”
“Oh, god yes, and totally unexpected.”
“It’s your reward for looking after me so well this afternoon, I’ve never been so well attended during my period.”
We left the table before the others, because both of us were exhausted. We kissed everyone on their cheek but I refrained from Tiffany, unsure if it would be appropriate. Catherine hugged her eldest daughter, and they shared a chuckle.
“Sorry, Kate, please wait a second.”
At our bedroom door, I turned and walked back downstairs to the dining room, terrified because I’d forgotten my napkin. When I rounded the door, I saw Tiffany’s seat was empty, and I stepped into the room.
My head shot a look towards the head of the table where I saw Catherine in her chair with both legs resting on the polished wooden table.
She was mostly naked, stripped to the most delicious red rose coloured lingerie. Her blouse was partly opened and bra rolled down, with both breasts exposed and erect nipples clearly displayed.
The room was empty aside from my surrogate mom, and head firmly planted between her legs. Tiffany was servicing her mistress and, by the sounds of Catherine, she was doing an excellent job.
“Did you forget this, Jacob?”
Catherine held my napkin up to her nose and sniffed its contents. She stared at me, smiling when she’d caught my scent, nodding her approval as though she liked it.
“Don’t worry, I’ll ask laundry service to give your napkin an extra scrub to get the grease stains out.”
Tiffany didn’t pause for a second and, since it was none of my business, I waved at Catherine before making myself scarce.
I ran back to Kate, who saw my horrified expression. She gripped my hand and marched me towards our bed.
“You didn’t honestly think mother hadn’t realised you were getting some under the table, did you?”
I laughed and dove into bed, dragging the quilt over both of us, holding my sweetheart tightly. Her stunning blue eyes bore a tunnel into my heart.
“Are you happy, Jacob?”
“Yes, very. In fact, I’ve never felt happier. Everything will work out fine.”
“Yes it will, dear boyfriend.”
Kate’s Point of View.
Our relationship was in a good place. It hadn’t been difficult to mould my boyfriend through encouragement, love and a little discipline because Jacob’s strength and spirit were such as I’d never encountered in anyone before, man or woman.
He was a towering man in physical and emotional aspects, and I felt fortunate that he remained always willing to submit to me. I had never taken his loyalty or love for granted, knowing he could retract that at his absolute discretion and do so in a moment, leaving me heartbroken.
Jacob was the sort of man who would stay if valued properly, and disappear if he wasn’t. He was a gift from the universe and one I was determined not to squander.
As my boyfriend calmly slept like a resting knight beside me, I rifled my fingers through his hair and whispered a prayer to him.
Precious Jacob, may the universe keep you safe through the night.
May your cares and burdens be few and light.
May Natalia cradle you with her love.
May she bless your sleep and good health keep.
While she rests nearby, remembered always, I will guard you through the night.
I never told Jacob that he frequently talked in his sleep. It wasn’t clear to me how conscious he was during our conversations and, in particular, those we had after his night terrors.
I was fairly certain that my boyfriend had no recollection of the night. I held him sobbing and sweating in his arms while he pointed to the bottom of the bed, screaming for Natalia.
My relationship with Jacob’s family was embryonic, but his sister was keen to explore a friendship with me. When I called about his night terrors and mentioned Natalia by name, she explained.
“Jacob was part of a team that exhumed mass graves. One of the bodies he carried from a mine shaft to the temporary morgue was later identified as Natalia. She was six years old and was murdered with her whole family.”
“Is that the source of his PTSD?”
“Yeah mostly, but the combat he experienced impacts, too.”
“Why can’t he let go?”
“He won’t let go of Natalia, ever. The best you can hope for is that she becomes manageable.”
“Why?”
“Because he’s terrified that if he lets her go, she’ll disappear forever and nobody will ever know she even existed.”
I wept after that phone call because I couldn’t imagine the horror my boyfriend had experienced.
I came up with a poem and night time routine to help soothe Jacob as he fell into a deep sleep. He had fewer night terrors, so I assumed it worked. Every night, even when my boyfriend believed I fell asleep, he relaxed and went into a deep slumber. I soothed him, cradling my soulmate until he was completely at peace.
If Jacob woke, I comforted him until he could drop off again. I never mentioned it because he would come to me when ready.
It was the least I could do for a man that trusted and loved me so deeply, protecting me whenever he could.
We had challenges ahead, that was for sure. Daddy’s company was an unwieldy beast that must be tamed and trained, reformed and restructured.
I couldn’t do that without Jacob and so his education and my salvation would continue wrapped in a warm blanket of love.
Next Chapter:
What a lovely and loving chapter Kate, poetic in every sense of the word. Catherine is quite the firecracker, isn’t she? Yet another character developing nicely, as is Tiffany.