Yes Miss Jessica Pt 03

'Eyes up here, Hunter...' Miss Jessica's ethereal voice sent shudders through my body, raising the hairs on my skin and echoing around in my head like a pinball machine. It didn't stop. It reverberated off the walls of my skull, hijacking and replacing my own internal dialogue with the script she wrote.

'Fucking touch me.' I felt her whisper gently fill my left ear with the heat of her breath. Then, Miss Jessica grabbed my hands and placed them on her body so they could roam. Every inch, every sound, every moment of her was disorienting and bizarre, like a trip down some Alice in Wonderland rabbit hole where everything is meant to enchant and trap you forever. The more I touched her, the more I wanted to touch her. And the more I wanted to touch her, the more I wanted her to touch me.

But it was never enough. She was water that never quenches your thirst, food that never satiates your hunger. It was a feedback loop of bottomless seduction, of mesmerizing skin.

Her entire body was bathed in the limelight, aided by the glowing white of the moon seeping through the shutters on her living room windows. Her skin glowed as if she was a fantasy, a mere figment of my wildest imagination- a fever dream.

Those lips, so luscious and enticing, manifested within me whatever they spoke as if I was helpless in the matter, hypnotized and under her complete control. My reality was whatever she said it was. My actions and thoughts were whatever she wanted them to be.

And they became my biggest desires as well.

'I'm Miss Jessica to you. In public and in private. Got it?'

The warmth of her skin. The chill down my spine. The sopping, hot flesh that was gripping my cock from every angle.

It was too much.

I couldn't last any longer.

'Yes, Miss Jessica. Yes, Miss Jessica. Yes...' I breathed.

Then she disappeared again, and I was left with nothing more than my white stucco ceiling and the golden yellow sunrise filtering through the curtains of my second-story window.

Despite the ceiling fan swirling on full blast and the AC set at 70, I was in a cold sweat and exhaling as if I had just finished a sex marathon with the real Miss Jessica.

"Fuck..." I breathed, then realized the warmth and moisture I had been feeling between my legs was, in fact, real. It was normal for me to wake up hard but wet dreams, not so much. At 19, I thought I was done with those- but I guess Miss Jessica had other ideas.

She always did.

I reached down to check the damage, and much to my displeasure, it wasn't just my boxer briefs and shorts that were soaked through. My sheets were too.

Again.

"You've gotta be fucking kidding me...." I groaned and rolled out of bed to check my phone, just in case she had finally texted me back.

It was Friday now, and I woke up haunted by Miss Jessica every day since that Tuesday night. That entire night paradoxically seemed like a blur and a timeless daydream, but I remembered the right parts. She was in my dreams, whispering to me, instructing me to touch her and look into her eyes to say her name.

And every day since that next morning, I had texted Miss Jessica but got no reply.

The game was evident to any impartial third party but not to me.

All I knew was that I wanted more. I needed more. And that was precisely how she wanted me to feel so that I would chase, so that she would have the power.

And I would have none.

I tapped my phone to bring up the lock screen.

Nothing.

Disappointed and sexually frustrated despite my body's involuntary releases, I ripped the sheets off my bed and threw them into a pile on the floor before doing the same with my pajamas. Instead of donning new clothes and heading to the laundry, I just stood there butt-naked, half-erect, staring at the heap.

My mind and body were as restless and messy as the tangled ball of linen, cotton, and cum.

14 girls. That's how many I had been with before Miss Jessica.

I had been inside 14 pussies.

I had looked into 14 sets of eyes.

I had felt 14 bodies.

I had listened to 14 mouths whisper things as we fucked.

But never had I ever experienced anything like I did the other night...

It wasn't the age difference or the mystique of the "MILF".

It was her.

The other girls I had been with, like Danielle, were just physically attractive. They got my dick hard and occasionally had cute little looks, quirks, and mannerisms that added depth to their character or uniqueness to the experience.

But everything about Miss Jessica was sexy:

The way she talked to me.

The way she handled and manipulated me.

The way she dressed.

The way she carried herself.

The way she kissed and touched me.

All of it was intoxicating.

Although I didn't realize it yet, Miss Jessica had me going through withdrawals. I was an addict who got his first taste, his first hit, and then suddenly had all the supply in the world disappear overnight.

I walked back to my phone, unwilling to accept the prison of Miss Jessica's chase cycle, and determined to see her again. I couldn't have any more wet dreams. I couldn't keep washing my sheets every fucking day. I needed the real thing.

I needed her.

She was driving me crazy.

My fingers blazed through my passcode and contacts to find her name, pressing call and unwittingly playing right into her hand.

Within seconds, I held it to my ear and hoped the ringing would be replaced by that enthralling voice that still dominated my thoughts. My stomach knotted up as my body told me that I was giving up all my leverage and power and dropping it straight into her open hand.

But I didn't listen. I couldn't help it. Miss Jessica was smarter than me, and I wasn't yet the man she would make me into. There was no winning here, not in the traditional sense, and certainly not with Miss Jessica.

I was too oblivious and spellbound to even realize any of that at the time.

The only victory was seeing her again.

As of now, the first step was complete: the ringing stopped.

Finally...

"Hello..." That voice came, and my heart skipped a beat.

"Hey!" I answered back excitedly. "Hey, I'm sorry I know you're probably headed to work soon, but I was curious if maybe you'd want to get lunch today or something."

'Come on, come on. Please say yes. Please say yes!' I pleaded with the gods, feeling alert and jittery from my hyperactive nerves. I held the receiver end of the phone away from my mouth as much as possible so she wouldn't hear my frantic breathing.

"Mmhmm. You're ok, sweetheart." She returned in a calming, matronly way. "Have you missed me or something?"

'Fuck. What do I even say to that?' My brain scattered. No woman had ever talked to me like this before. It was turning me on, though. Wet dream be damned, I was no longer semi-erect.

"Well, uh, I had a really good time on Tuesday. Didn't you? I thought we might keep that going." I wasn't even remotely sure if I was doing this right. Fourteen women before her, and this felt like riding a bike without having training wheels first- or even knowing what a bike is. She wasn't an ordinary woman.

My five-year teenage relationship and thirteen other 18 to 20-year-old hookups did nothing to prepare me for this. She was two and a half decades older, with that much more experience, and she used every bit of it to overwhelm me into submission. This was like trying to argue your own case in a government court without an attorney to represent you.

I was trying not to sound as desperate as I was feeling. It was compulsive, though, and there was no disguising it.

Not that Miss Jessica cared. This entire sequence of events, and my corresponding reactions, were manufactured by design, just like everything she did.

"Mmmm. Tell you what, lunch today sounds great. You pick the place and time and text it to me. I'll meet you there. Ok?"

"Yes. Ok, I'll do that." I agreed instantly, already trying to think of every restaurant between my house and her office near Logan Square.

"I'll see you then. Bye, Hunter."

"Bye, Miss Jessica."

She finished with a laugh, a muted version of the one she expressed while riding me on her couch- the same one that hounded my psyche for the last 72 hours. It left me with goosebumps and made my erection worse as I heard those three beeps signaling the end of the call. I was horny and ready to cum again, but masturbating was out of the question. Miss Jessica had given me an assignment, the first of many.

"Fuck. Ok." I sighed and hurried over to the desk, so I could start up my laptop and survey the map of possible options. Miss Jessica seemed to have expensive taste, and I didn't want to disappoint her on what I believed was my only chance to keep things going.

After a half hour of searching, I found the perfect spot.

Let's go to Oyster House. I can meet you there at noon. Does that sound good? I texted her, attempting to appear decisive and respectful simultaneously, careful not to make it seem like I was trying to boss her around.

I had a feeling Miss Jessica wouldn't like that...

My eyes stayed glued to the screen until I saw the little gray typing bubble, and then I waited eagerly, with butterflies in my stomach, until the answer popped up.

Perfect. See you there.

That was all I needed to get my ass into gear with new shorts and a trip to the laundry room. I was on cloud nine now after days of being stuck in limbo. A big stupid grin made my cheeks hurt, and my cock took its time, calming down from the excitement of just being near her again.

Thankfully, it still timed things perfectly because Lauren came in just as I was stuffing everything into the washer.

The washer and dryer were both front loaders, so she immediately noticed the contents of this load, even though I tried to disguise the presence of my shorts and underwear.

"Again? Should I even ask?" She jabbed, 16, and aware of the reason I'd be throwing all these things together in the same load for the third day in a row. Lauren was, and still is, incredibly nosy and way too smart for her own good. There was no hiding or lying with her.

All the boys loved her at school, but they were also scared shitless of her for that very reason. She's like a psychic, seeing right through you and calling you on your shit. She still is to this day. Only now, it's a thousand times worse.

"Just washing my sheets, Lauren." I sighed, pouring the thick blue detergent into the machine.

"Mmhmm. Sure. How's 'Miss Jessica'?" She teased, dramatizing her name as if she was Juliet on her balcony calling out for Romeo.

"Is this why you came in here?"

"To tease you for having a crush on an old woman? Yeah. Absolutely." She smiled smugly, crossing her arms and leaning against the door frame. Her bright green eyes were way too full of energy for a teenager awake at 7 am during her summer break. After the hardships of last year, I'd gotten her into a routine of shadowing me in my work, which means she starts the day when I do, no matter the season. I was happy about it because it meant she was healing. But I was also slightly regretting it now because she was twice as annoying as she usually was.

"She's not an old woman. She's 45. And I don't have a crush on her."

"Oh, please." She laughed, mocking me ruthlessly as only siblings can do: "Can we get lunch today, Miss Jessica? Please, Miss Jessica? I love you, Miss Jessica. You are so obsessed with her. You weren't even like this with Courtney."

I whipped around as the machine started its cycle and glared at her. She knew better than to bring that name up with me.

"I'm sorry." She apologized instantly and hugged me. "That was too far."

"It's fine," I mumbled into the side of her head. "What did you actually come in here for?"

Lauren took a step back and assessed me with a horrified expression. "Are you ok? I'm sorry, Hunter. I really am. I didn't mean to- "

"Lauren, really, it's fine. I'm over it. I just don't want to talk about it. Now, what did you come in here for? "

"Can I go stay at Angelica's this weekend? Her parents will be home, and there will be no boys. I promise."

My body got a massive dump of dopamine at that question. For one thing, my horny brain hoped that meant I might get to spend some time with Miss Jessica. But more importantly, Lauren hadn't done anything like this since before our grandparents died.

Their passing, and the events that followed, took a massive toll on her. She was depressed and unwilling to leave the house for months. She had recently gone out for a few hours to start spending time with her friends again, and occasionally they would come over for sleepovers, but Lauren never stayed on her own overnight. It took patience and painstaking effort to get her to this point, so I was happy to let her take that next step.

I couldn't help but smile again, proud and delighted at her progress and healing.

"Of course. That sounds great. And you know I don't mind if you hang out with boys. Just be careful." I answered her.

"I know, Hunter. I'm not gonna end up like mom, I promise. I want to be like you." That made me smile too. She poked my stomach as if to skirt around the awkwardness of being endearing to her older brother. "All the boys I know are dumb anyway."

"Good. Are you going over there tonight or tomorrow?"

"Tonight, if that's ok. Can you drop me off? After your lunch with Miss Jessica..." the joking tone came back.

I rolled my eyes. "Sure."

"I'm just teasing, you know. It's weird that she's literally old enough to be our mom, but I'm glad that, in some creepy way, she at least makes you happy. Just be careful too." She shifted again, this time to her protective sister's voice. I knew what she meant. It was another veiled reference to she-who-shall-not-be-named.

The message: be careful getting attached so quickly. You know what happened last time.

But with Miss Jessica, I didn't have a choice.

My fate was already written.

By her.

-

I arrived at the restaurant earlier than usual to calm myself down before she came. Something felt different about this encounter. It seemed hopeful but also like a crossroads. Everything with Miss Jessica felt like a test like she was watching me to see what she was working with. I didn't know what she was looking for, but choosing the right path entailed doing it well.

For some reason, despite how simp-ish the behavior was, I wished I knew what it was.

I just wanted to make Miss Jessica happy.

I wanted her approval.

I wanted her love and affection.

I wanted her to pick me as her little boy toy...

Her play-thing...

Her sugar baby.

I was never the type of guy to be into that, but Miss Jessica made it impossible not to be. She was incredible and worth every second of working my ass off to please her.

The Oyster House was busy when I got there, like most places downtown usually are on a Friday- but I had made a reservation in anticipation of the crowds. I wasn't going to disappoint Miss Jessica with a thirty-minute wait on her lunch hour. Not a fucking chance.

Miss Jessica walked up five minutes to noon, punctual as usual, and was delighted to see me standing there waiting for her. Seeing her in that navy blue dress got me excited in more ways than one. It was much different than the red one she wore on our last date, the neckline was closer to the pearls that rested on her collarbone, and it stopped just above her knees rather than just below her ass. Still, it was sexy, hugging her figure tightly, assisting the imagination about what lay underneath.

Her hair was lightly curled again, though, parted in the middle as usual, and her eyes were popping from the color.

"Well, well, look who beat me this time." She grinned happily, extending for another hug. Now that it was clear this relationship was somewhere between sexual and romantic, I let my hands go to her waistline and caressed that slender figure as it pressed into me, her perfume making me weak in the knees as it wafted into my nostrils. The dress was a similar fabric as the previous one, and under my hands, her hips felt the same as they did that night: pantiless.

"Now I know how to impress you." I joked. "Just gonna keep arriving five minutes earlier every time."

"Mmmm. You're cute." She giggled as she fixed the collar on my polo, those eyes giving me flashbacks of my dream from this morning. "You picked a great spot, Hunter. I'm proud of you. This is one of my favorites. Did you make a reservation?"

"Yes, I did," I replied, my heart fluttering with happiness from knowing I did a good job on my task.

Miss Jessica was proud of me, and her hands brushed down my shoulders while examining the rest of my outfit: my only pair of gray slacks and brown dress shoes.

"Good boy. Come on." She whizzed past me, making a bee-line straight for the door. I half walked, half ran to catch up so I could open it for her. The look she gave sparked deja vu, like I was living in the twilight zone, replaying moments of Miss Jessica's approval. I sensed she was also proud of me not only for my choice of lunch spots but also for being a quick study.

I was learning: Miss Jessica doesn't open her own doors.

Unlike the last two times when she took command of the situation, Miss Jessica paused just before the host stood and looked at me. This was my reservation, my choice of restaurant, and my plans. It was my turn to show initiative, and I felt her eyes analyzing me as I walked up.

The hostess caught my attention, too. She was shorter than both of us but had fiery red hair and petite, perky little tits that dangled under the u-shaped neckline of her blouse. Its black color starkly contrasted with her milky white, freckled skin.

It distracted me for a moment, especially when I darted back to her name tag, which read, "Abigail."

"Hi!" She greeted me happily with Granny Smith green eyes, which took a little liberty upon themselves in terms of where they wandered after noticing how mine had started the trend.

"Hi, I have a reservation at 12 under Hunter."

"Yes, we can get you seated now." The cute redhead smiled, continuing to check me out and then looking at Miss Jessica. "Right this way."

We walked to a table near the back corner. Abigail's figure was as lovely as the rest of her, and since she was walking ahead of us, I could admire it without much effort. After the hostess set the menus down, I sat on the far side while Miss Jessica stayed put. Her eyes were scanning me again, critiquing and analyzing.

"Thank you, Abigail." She asserted before doing the same to her.

I won't bore you with the details of the lunch itself. All you need to know is that the conversation was bland and uneventful, unlike all of the previous ones- and that's not what you came for.

The most exciting topic was sports. We discussed how well the Phillies were doing, and I disappointed her by divulging that I'm a Yankees fan.

Other than that, it was mostly about work, how the rest of the week had gone for each of us, and her telling some childhood story about how she went to Phillies games with her dad at Veterans stadium back when they had that hideous light green astroturf.

Miss Jessica didn't touch me, and she flirted only occasionally.

That didn't change until just before the check came.

"Oh my god...." She groaned after rifling through her purse. "I'm so stupid. I left my wallet at the office. Do you mind covering this?

"Yeah, of course!" I sprang into action immediately. "I was planning on doing that anyway. Don't worry about it."

"Are you sure?" She double-checked, acting like she really felt bad for making me pay. If you haven't figured out where this is going...she didn't.

"Yeah, absolutely." I reaffirmed and grabbed the bill as soon as the waitress returned.

The moment my card hit the little black book, I felt Miss Jessica's heel creeping up my leg. Her eyes abandoned corporate professionalism for promiscuity and lust. And yes, it was that sudden. It stunned me into helplessness.