Kate Educates Jacob #18

Shopping Trip

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I parked my BMW at Kate’s City apartment. From there, we rode the bus downtown, sitting as close together as the seats would allow.

Kate held my hand wherever we walked. The mall and main shopping square were crammed because it was the end of summer. Retailers were shedding stock and discounting like crazy, preparing for their winter collections.

Kate tried everything on, in every shop, asking for my opinion on fit, colour, style and how well or badly garments suited her. We developed a scoring algorithm with a thumbs up or down result. We scored lingerie based on how well it fit, aesthetics, comfort and how easy it was to remove.

Once that was established, a ‘purpose of use’ multiplier determined its desirability. For example, if something were to be worn under a casual skirt on a walk through the park, then comfort and ease of removal were the prime movers for an overall score. If it were something to be worn around the house, then we combined fit, look and removal scoring. It was a complicated exercise in futility, but fun.

Kate planned lunch at a secluded Italian restaurant on the outer fringes of the shopping centre. Once we were seated, she ordered a half bottle of Pinot Grigio while I browsed the menu, selecting antipasti and a pizza for us to share.

We planned the next few week’s activities to help get to know each other better. Kate had upcoming social engagements, some of which required my attendance. My parents would visit my aunt in about a month, and she insisted we invite them to stay.

We scheduled time for work, planning a complete transition for both of us from her car rental company to the Global Defence campus.

“Do you think Tiffany could do my job at the rental lot?”

“Not yet, maybe after your mother completes her training and even then you’d need her brought up to speed in leadership and how to manage. Why would you choose her?”

“Because she asked for help. There’s nothing worse than someone struggling who won’t ask for help. I’d rather employ a person who’ll seek me out than one who buries their head in the sand, pretending a problem will go away.”

“You’re also referring to me, aren’t you?”

“Why would you think that?”

“Because of my night terrors?”

Kate had said nothing about my PTSD, but when the terrors visited, she held me close, comforting my trembling body and tortured mind until I dropped off again. My nightmares manifested themselves in visions where the innocent dead from mass graves in Bosnia rose up and walked towards me.

“I’m sure that if you need my help, you’ll ask me for it, Jacob. I was only referring to Tiffany.”

She smiled sweetly, but I knew Kate was reminding me she was ready to help when I needed her, but wouldn’t push unless invited.

Kate was beautiful, clever and engaging without being bossy, yet firm and commanding. It felt like we decided things together, although the lead always came from her. I slipped away to the toilet and my phone buzzed while I washed my hands. Kate had sent me my first honey do list on an app designed for that purpose.

When I returned to our table, she smiled and raised an eyebrow. “If we don’t plan our diary and carve out free time, we won’t have much fun, especially with the challenges at dad’s company. Our time will drain away like sand through our fingers.”

She was explaining why she’d sent me a list although it was unnecessary.

“Will you ever refer to GD as your company?”

“Probably, but only when I feel deserving and most likely only to my kids.”

“Your kids?”

“They would be my kids if I gave birth to them, yes.”

I noticed her wry smile and knew I was being teased.

“Would they be my kids, also?”

“I hope so, Jacob.”

She seemed pleased I’d asked. Kate had a way of making me feel secure and happy. My heart skipped a beat although many guys would run across miles of broken glass when hearing talk of babies so early in a relationship.

It comforted me that Kate saw us as a long-term proposition.

“It won’t be for a while yet though, Jacob, so don’t worry.”

“I’m not worried in the slightest.”

She slid closer, hugged me, and we held hands under the table while nibbling through our meal. Kate stroked my thigh, squeezing to show her happiness, then she scraped the seam of my French knickers through my jeans with a sharp nail.

“Don’t worry, we’re halfway done with the shopping trauma.”

“I’ve thoroughly enjoyed it so far.”

Kate rewarded me with a lingering kiss when her warm tongue searched my mouth. A rapidly growing cock close to where her hand rested in my lap rewarded her good work. I felt uncomfortable in her itchy lace panties and shifted my butt to find relief.

Our server had deliberately seated us in the most secluded booth in the restaurant. It was most likely where lovers met for privacy and he’d spotted that we were in that category. Even the music wafting through the restaurant was meditative by the time it reached us. We were in a romantic oasis.

“That’s unfair.”

She rubbed my cock shaft extra hard to ramp up my discomfort, smiling, teasing and torturing in the most seductive way.

Kate kissed me on the lips, scratching the lace and my skin beneath it, while rubbing my cock up and down.

“Sorry babe… I’m feeling horny again and I can feel my knicker lace through your jeans.”

“It’s hard for me to hold back, Kate, I’m trying really hard to abstain because you told me to.”

“I know Jacob and I treasure that. I’ve decided you don’t need to be caged. Your obedience to me is off the charts and I just don’t think it will add anything. We’ll only do forced chastity if it pleases you to try and for fun.”

“Do you trust me, Kate?”

She smiled and bit her bottom lip, curling a tongue tip to the corner of her mouth. When Kate stared at me, her soul was laid bare through her beautiful blue eyes.

“I trust you with my life, Jacob. We are soulmates.”

“I believe that too.”

An erection almost tore the buttons loose from the jeans I wore. Kate noticed my discomfort.

“I’ll help you out because you’ve been so restrained and very attentive so far today, but please don’t make me regret it later.”

The table and its white linen cloth covered my lap with no line of sight to it from any other guests. I was shocked when Kate slipped my fly buttons open, then pulled my cock out of her lacy knickers because it was an enormous risk to both of us.

My exposure felt dangerous, although the release of my cock from a tight, lacy prison felt wonderful. The cool air and freedom excited me when my cock shaft extended fully.

“You said I couldn’t cum until tonight.”

“I said you couldn’t orgasm until tonight.” She corrected me. “I can still get your cum without an orgasm.”

I felt my cock head rub against the linen cloth pinned to the underside of our table until she peeled my foreskin backwards and pushed downwards. She pulled her lacy knicker band underneath my balls where it cut a little, but nothing would stem the flow of blood to my proudly upstanding cock at this point.

When she peeled my cock a second time, Kate wanked me gently, and my nine and a half inches reared up fully. She bent my shaft towards my stomach to avoid knocking me against the table.

I felt a heat and wetness under my foreskin and knew my glans was lubricated with pre-cum. I’m not circumcised, so when she reversed her stroke upward, Kate slipped her thumb underneath my foreskin, rubbing pleasantly.

She dug her fingernail in, delivering a mild shock jolting me. I felt semen rise through my urethra, powered by a highly stimulated prostate gland. It felt like I might explode and paint the underside of the table and my shirt bottom with cum. I worried that I’d ruin the cloth or worse, provide the next customer with an unwanted creamy dessert in their lap.

“It’s all about timing, my dear. Let’s work together to take care of your problem while making sure you don’t orgasm.”

My head was totally fucked, many thoughts ripped through my mind while I struggled to keep a straight face for the other diners. My cock was being milked by the woman I loved.

“I want to stand on the table, beg you to finish me and squirt my load in front of everyone while declaring my undying love for you.”

“We might need to give more than a fifteen percent gratuity to get away with that.”

“That tastes lovely, babe.”

Kate sucked gently on her thumb, before sharing my salty flavour through a kiss. She stroked my shaft, wanking it slowly, occasionally soaking her thumb in the wine from her glass before rubbing it into the top inch of my cock.

She used her nail to flick the eye of my penis gently, daring me to hold back my orgasm, keeping my cum load stored for when she would summon it. When she thought I might orgasm, Kate stopped, and hauled me back down from the edge, while chatting casually as if seeking my opinion on her hair colour or choice of shoes.

My cock throbbed because its shaft was solid, and my balls were full of semen. The tube that led to their release was chuffing like a steam train. I was ready for more wanking but already felt partly satisfied having closed in on and then lost my orgasmic.

She’d taken me to the edge three times, easing back just before an explosion. When an orgasm approached, Kate stifled it, bent my cock downwards and pinched the base of the tube that would otherwise violently eject my sperm through a veiny, solid cock.

“I feel my cum seeping up gradually when you release me,”

I moaned, then whimpered gently while scanning the restaurant to see if anyone was onto us, terrified of drawing attention to myself.

“Each time you get close, I’m ruining your orgasm, Jacob. It's good discipline training and you should enjoy it enough to survive until later.”

“It f-f-feels f-fu-. It feels great.”

I hauled back the obscenity she disliked so much, with an image of Beauty and Kate’s riding crop as an incentive.

“Good boy Jacob, I’m thrilled with your progress, but please restrain your orgasm. Let me get release ejaculate now, then we can save the best till later, when we can both enjoy your orgasm.”

“I’ll be empty.”

“Only for an hour, you’ll be fully loaded for when I want you later, but you won’t be stomping the ground like a prize bull until then.”

I shuddered, ascending towards a tipping point and Kate stopped wanking me again, holding my pleasure above a chasm while sipping her wine seductively, swilling it around her mouth. She wrapped her hand around my shaft, squeezing its base tightly, almost forcing my cum backwards. Kate squeezed and released me several times with a vice like grip that felt painful and joyous.

The pressure in my shaft subsided from a high point when she allowed it to, and my orgasm passed once more as a non-event. Kate wouldn’t masturbate me to completion and her stifling of my climax had just enough satisfying effect to prevent me bouncing off the ceiling. When my orgasm was no longer a threat, she continued wanking me gently while chatting in a relaxing tone.

“I might change the yellow blouse, honey. I prefer the light green in the same style.”

She casually sipped wine, steadying the glass with one hand while compressing my cock with all her might in the other. My orgasm built, and expression couldn’t hide it, so she used my rippling face muscles and the tension throbbing through my shaft as a measure.

Kate stopped suddenly, denying my orgasm again.

“Which blouse do you prefer?”

She smiled cheekily and winked.

“I think you should… ahh, try the green blouse… umm, and we can compare both again,”

Kate snuggled closer into me while maintaining her vice like grip at the base of my shaft, keeping my precious seed where she wanted it to stay for now.

“It’s a long walk, and might be for nothing.”

She was testing my resolve and obedience.

“Ahhh, It’s… err, good to walk, and worth it to be sure the blouse you buy is the right one for you.”

My voice wavered under extreme sexual duress, but I held the line.

“Fuck… Jacob, you’re damn near perfect.”

Kate nudged me with her free elbow in amazement. It was a surreal moment because my cock throbbed, jerking gently while fully loaded and ready to blow the restaurant doors off. My girlfriend continued cuddling me, teasing my orgasm up and down, while asking my opinion about her purchases.

“This is the best day out I’ve ever had, darling.”

I sipped my wine awkwardly, with a shaking hand.

“I feel the same way. You have serious discipline, Jacob, and you are a very attentive and loving boyfriend.”

“You make me want to be a better man, Kate.”

Her eyes melted and tears welled up. I knew I’d pleased her.

“I’m not done with you yet.”

Kate pulled my foreskin back to the point of pain and held it so that I bucked in my seat.

“Hold on honey, don’t get ahead of yourself.”

After ten-seconds, Kate released the pressure on my cock with an upward stroke, covering my pulsating glans with its protective foreskin. She scanned my face for signs of an impending orgasm.

“This is called ‘edging’ babe, and it’s one technique that I’ll use to manage your current condition. Does it feel good?”

“It’s amazing. I can’t believe I haven’t blown my load.”

“I won’t let you orgasm, Jacob. I won’t abuse, misuse or neglect you either, because I love you.”

“I love you too, Kate.”

“I know.”

She shuffled my cock up and down quickly for half a dozen strokes.

While talking to me, Kate continued wanking slowly, with a firm hand on the downward stroke, forcing me back up to the edge. When she felt my orgasm rise, she slowed down, stopped, reapplying pressure where it was needed to contain me, before starting again when I’d settled.

She squeezed my cock tightly, then pulled down much harder than before, summoning a server while holding me fully back. I almost exploded when the young man approached.

“Can we get the check, please?”

“Yes, of course, madam.”

“And some refreshing mints too?”

“No problem. May I clear the dishes away, please?”

While our server gathered the plates and glasses, Kate released my cock for an instant, then hauled my foreskin back to pile more pressure on my glans. He was oblivious to her good work under the table and ignored us while she leaned on the table with her free elbow, whispering lovingly to me.

I had an apoplectic fit trying not to look at the guy collecting dishes so close to my bulging cock.

What if I cum while he’s standing right there?

“Are you satisfied, darling?”

Kate asked innocently, and I nodded.

“Do you need anything, Jacob?”

“No, no… err, everything is fine.”

I mumbled in a state of panic. The server glanced at me, momentarily concerned, and scanned my face.

“Are you okay, Sir?”

I look and sound like a fucking maniac.

“Oh… god, yeah of course, I’m fine… umm… err… oh, it’s lovely food here. Definitely five star servicing… I… err, mean, service.”

I nodded, smiling normally, hopefully confirming that I was fine. He moved away with our dirty dishes.

Probably thinks she’s taking her mentally handicapped brother for lunch.

Kate laughed, released my cock and I regained my composure, but was sure there was more to come.

“When you get hot and bothered this time, try to switch gears and focus on your breathing. Take long inhales counting to six each time, exhaling from your stomach.”

“Okay, but I’m struggling a bit. Can I cum please, please? Please, Kate?”

I begged, far more desperately than intended.

“I’m giving you a ruined orgasm, but don’t worry because it’s not as bad as it sounds. I’m going to milk you dry while stifling your precious orgasm, then we’ll snuff it out together later, babe.”

She’d already begun masturbating me again with gentle, full and firm strokes.

“Argh… its building, Kate and I can’t hold it.”

I pleaded for her mercy then stopped when the server returned to our table with a bill and placed his card machine in front of me, less than a cock’s length from my erection.

Kate fished out her credit card from a purse using her free hand and passed it to me.

“You pay Jacob. Fifteen percent gratuity, like we discussed.”

She whispered her PIN number, never letting go of my cock.

The server held the card machine while I rammed her plastic into the slot unsteadily. I waited, selected a fifteen percent gratuity that she’d agreed to, and entered her PIN. She’d stopped wanking me again, and I felt her thumb block the semen load halfway up my shaft by pressuring my urethra.

Another orgasm subsided, partly because of Kate, but mostly because of the server and his threat to my sanity.

Kate was determined to release my cum without the orgasm she said might change my attitude. If she failed I felt sure the restaurant would have both of us arrested while trying.

We waited for the payment authorisation, while she wanked me up and down again slowly, smiling at the server, then at me and then at him again. I rode her induced orgasmic edge, barely able to see the words on the payment reader.

For fuck’s sake, authorise it, you cunt.

My semen settled further up my shaft this time, and her thumb blocked it just in time, almost daring my load to rise further.

If she misjudges this, we’re fucked.

Our server tore off the receipt slip and handed it, along with Kate’s card, to me.

“I’ll get those mints for you shortly.”

He had other customers to look after and sauntered away, happy he’d got a good tip with no idea what Kate was doing with mine.

“Oh, thank god he’s gone.”

My voice was strained, my cock even more so.

“If I were only edging you, I’d stop now, but you’ve been such a delight today I want to give you something special, a halfway house to absolute satisfaction. It should tide you over until tonight.”

She wanked my solid shaft again, stopping before the edge of my orgasmic heaven. My semen rose further, then stopped and this time, she used her thumb to push upwards instead of blocking it. There was no explosion, and I felt numb, yet content, while my cum seeped slowly from the slit at the end of my cock, which jerked gently as if stifled.

Kate teased the slimy cream out, squeezing my urethra from the underside of my shaft. I felt a dull, pulsating throb while she emptied my balls, milking them, stroking me back and forth expertly, holding me on the edge of oblivion and ecstasy but never taking me beyond that into orgasm. My cum flowed, and I felt relieved but there was no climax.

She splayed her thumb and forefinger wide to hold my cum rather than allow it to drip to the floor, onto my lace knickers or mess up my jeans. Once my cock finished jerking, she reached into her bag with her free hand, pulled out a wet wipe, using it to clean the slimy cum from my cock.

“Hold that dear.”

Kate handed me a cum filled wipe while taking a second one. This time she pulled back my foreskin to its maximum extent and cleaned my cock head completely, paying particular attention to wiping the banjo string.

“Flush those down the toilet, Jacob.”

Kate handed two more cum filled wipes after cleaning her hands.

“And use these clean ones to finish cleaning, I can’t abide a smelly cock.”

Our server returned, oblivious to my condition, and set a plate of mints on the table, then left. Kate kissed me hard, before unwrapping two sweets while I buttoned myself.

“Thank you, Kate.”

I felt strangely satisfied, but ready for more. A calm had been granted before going into the storm.

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