Yes, Miss Jessica Pt. 03

"What are you doing this weekend?"

"Uh..." I tried to keep my breath steady amidst the unexpected change of pace. "Lauren's staying at her friend's house till Sunday night, so...nothing- at the moment."

"Good." Her heel was now right between my legs, gently pressing against me and making the area it rested on increasingly supportive for those nude pumps. It made my skin crawl, and tingle like it was being pricked with a thousand needles laced with vapor rub. "Don't get too excited, Hunter. We're still in public."

"Yes, Miss Jessica," I muttered nervously as I felt the heel press in just a little more, making it even more difficult to obey her command. My body shuddered as if hit with an icy chill, and I looked around to ensure no one else saw.

"Pack a bag when you get home, and come to my place as soon as you drop her off." Miss Jessica instructed me, with her heel now pressing against a solid surface. "You're not leaving my property until you pick her up."

I was pretty sure I was visibly sweating at this point. Miss Jessica's 180 had me trembling. This was a situation I had never been in before. My body and brain were unsure of how to deal with a woman as beautiful and sexy as Miss Jessica, twice my age, digging her heel into my growing cock while getting lunch in a busy restaurant.

I fucking loved it, though. I had never been so turned on in my life, and that's saying something for a 19-year-old boy.

"You better calm down before we get up." She taunted me. "Otherwise, Abigail's gonna see your boner."

When I say I was at a loss for words, I mean whatever portion of my brain forms coherent sentences just stopped operating entirely. I looked back at Miss Jessica like a dumbass caveman whose dick controls all his life decisions. The light was on, but no one was home.

"Well? You want to fuck her, don't you?" I was freaking out now. Miss Jessica wasn't even attempting to keep her voice down. There were tables all around us, but somehow it was like we were in a video game, and all those people were just NPCs. Miss Jessica's words didn't seem to matter to anyone but the two of us, nor did the fact that she kept digging her heel into me harder and harder. It was like she had the master controls of the matrix. Dramatic, I know, but I was too overwhelmed to think of it in any other way. "Hmm? Are you going to answer me, baby boy?"

"Yes, Miss Jessica." I strained through a not-so-straight face. "I do."

"Mmm." She giggled. "Well, maybe I'll let you. But we've got some work to do first. Mr. Hunter Ambrose isn't even remotely ready to keep adding to that number of his. Not yet.." she dug the heel in further. "Wouldn't you agree?"

"Yes, Miss Jessica." I panted, to no avail, although I wasn't really sure what I agreed to. This situation was conflicting, though, because, on the one hand, I wanted her to stop; and on the other, I wanted her to keep going. I was wearing slacks, which meant everyone would see that boner the second I got up, but Miss Jessica finally released her heel and gave me some relief.

"Just be as good of a student with me as you were in high school, and you'll have no problems." She winked.

"What are you going to teach me?" I asked nervously.

"Everything."

The waitress came back and set the checkbook back in front of me. As soon as my debit card was back in my wallet, Miss Jessica was on her feet, which meant I was expected to stand up as well, boner and all.

Between the flexible Cotton and spandex of my boxer briefs and the light wool of my slacks, the peak I had underneath them was impossible to keep secret. So, I just followed her out of the restaurant, one hand in my pocket, fingers pressed forward, hoping it was enough. We walked right past Abigail, who said a friendly goodbye while I tried to hurry and angle myself so she wouldn't see my hardness as Miss Jessica had prophesied.

To my horror, Miss Jessica walked right up to her rather than heading to the door.

"I just wanted to say I think your hair is so pretty." She gushed, making Abigail smile, and making me stick around long enough for her to see my not-so-little pants tent.

"Aw, thank you!" Abigail blushed, taking those auburn locks between her fingers and gently running them downwards. "It's my natural color too. I love it."

"Oh. It's beautiful. It's like fire. And it's so long and luscious too! "

Oh. My. God. She was clearly doing this on purpose, and for reasons I don't want to psychoanalyze, it was making my problem worse. Abigail did, in fact, notice. Miss Jessica was standing at just the right angle so she could easily view me from head to toe.

The little exchange lasted just long enough for her to do just that, and she flashed me an awkward but arousing, closed-lipped smile.

Finally- FINALLY- Miss Jessica broke away and nodded with her head towards the door, prompting me to walk forward and hold it open for her- which I did happily.

Miss Jessica doesn't open her own doors.

In front of the restaurant, we hugged again--this time for much longer and much closer.

"You're a good boy, Hunter." She whispered in my ear, petting my erection and sending chills through my body like she did this morning. "Let's make sure you stay that way."

"Yes, Miss Jessica," I whispered back in a choppy voice. "Do you want me to walk you back to your office?"

"That's a wonderful suggestion, but I won't humiliate you anymore by parading this hard cock in front of everyone." She said as if she was showing me mercy. "Instead, I want you to go home and prepare for this weekend. Think about how much fun we're going to have, but don't you dare empty anything. I want it all to myself. Your cum belongs to me now. Got it?"

"Yes, Miss Jessica..."

Miss Jessica telepathically signaled her intentions for the weekend through the mischief she wore proudly on her face just before she turned to make her way back to the office.

I watched her every step, stuck in place with that noticeable bulge in the middle of my pants until she disappeared around the next street corner.

That boner lasted until I got home.

Lauren went to Angelica's house even earlier than planned, so I was on my way to Miss Jessica's around 3 pm.

She had gone home just after lunch and was patiently waiting for me to arrive, according to the text she sent with her address.

The warm, humid summer air blew through the windows of my Civic as I pulled into her long, winding driveway. The two-story brick mansion at the end brought my erection back when it entered my field of vision. It bore a quaint, picturesque design that looked old and storied yet innocent.

That appearance was a mirage, though. While Miss Jessica was ultimately a good woman, she was anything but innocent. Just like the simple, natural beauty of the trees and the landscape that enveloped the property, her charm and gorgeous appearance made you feel safe. But just behind that halo effect was the ultimate, conflicting dichotomy: the soul of a temptress with the heart of a mentor.

She'd return you to the wild twice the man you were when she found you, but she would have her fill of fun in the process.

And her fun was the torturous kind...

The playing games with you kind.

I was pulled to the black double doors underneath the front portico like a moth to a flame. The lantern above me was lit despite the high afternoon sun, and her doorbell's far-reaching, ominous chime rang out to signal my arrival.

I waited for two minutes, bag in hand until the figure of my new Mistress flashed in the glass side window.

The door opened with a creak, and there she was in a blood-red bikini with little red tassels hanging down the sides of her exposed legs, sunglasses hanging from her cleavage, drink in hand, and one of those big wicker hats on her head. Everything smelled of sun tan oil, making her look slick and shiny. There was a little bit of underboob peeking out of her top, too.

Judging by the glossiness of her eyes, she was already tipsy- which meant I was surely in for another wild ride. Although I'd soon figure out that 'wild' was the defining quality of every moment with Miss Jessica, for she was a genuinely wild soul.

"Do you want to touch me? Or would you rather keep looking?" Miss Jessica asked as I stood dumbfounded like a hypnotized, brainless oaf in her doorway. She had her other hand high up on the door, gripping it so it didn't move and causing her bikini to creep upward and expose more underboob.

"Uhh, fuck." I gasped for my fleeting breath. "Touching sounds...great."

"Well, if you come in, you can do both." She teased, taking another sip of her drink and looking down at my pants which were growing outwards again. "You can fuck me too...eventually."

"Ok," I replied nervously, stepped over her threshold for the second time, and shut the door behind me. There was that looming message in the air that I wouldn't be the same once I walked back out that door on Sunday night. Per Miss Jessica's instructions, I was stuck here until then. Not that I'd want to leave anyway, especially once the festivities commenced.

After today, I would never be able to look at brick houses with big lawns the same way again.

Her anchors were cementing themselves in my brain for good.

"Come upstairs with me. We'll set your bag down in my room, and you can change. Then we'll go relax by the pool."

"Ok. I'm sorry, I didn't bring a swimsuit."

"I didn't say you needed one." She grabbed my hand without wasting another second and turned towards her stairs. That's when I noticed the bottoms of her bikini were a g-string. From behind, she may as well have been wearing nothing at all, on the top or the bottom. Virtually all her skin was exposed, save for the tiny bits covered by those thin red straps and tassels.

I followed that ass up the stairs mindlessly, with Miss Jessica's hand guiding me. In her presence, I forgot everything except basic human functions. Walking, holding her hand, and doing what she told me were all the complex skills I was capable of at the moment, motor or otherwise.

This was the first time I saw her bedroom. On the surface, it looked completely normal. Most of the house had dark wood floors, and her bedroom was no different. There was a little sitting area in front of her bed with two expensive-looking white chairs and a wood-burning fireplace with a painting of a nude silhouette with bright red lips hanging over it. The bed was large and decorated with lots of whites, pinks, reds, and many pillows. A large, antique vanity with a little bench was off to the side.

Everything was lit by the bright summer sun streaming through the big window on the back wall, which had the shutter doors swung completely open.

It was a simple haven of romance and lust.

"Put your bag on the bed." Miss Jessica ordered, standing at the foot of her bed.

I did as commanded and set the bag down. Miss Jessica stepped in next and unzipped it as if it and all my belongings were no longer fully mine.

"Let's see, what did you bring?" She inspected the contents of my bag, invading it like she worked for airport security.

And, like airport security, she removed a handful of items with her free hand and placed them on the bed. I was distracted by the side view of her bikini, following every line and curve diligently. She had to snap to catch my attention.

"What's all this?" She interrogated me with a disgruntled expression on her face.

I looked over at the pile of clothes on her duvet. "Um...clothes?" I answered, confused. I wondered if it was a trick question.

"And what did you bring them for?"

"To...sleep in and hang out."

"You're cute. But no." She confiscated the clothes and walked behind us to her giant walk-in closet. I spun around and watched, unwilling to miss a second of that ridiculous body walking anywhere but also hoping I'd get an answer to this very confusing situation.

She came back out after a few seconds.

"I'm sorry, Miss Jessica. You said I was staying for the weekend, so I figured I needed clothes."

Miss Jessica walked up to me and took my chin between her pointer finger and thumb. "From this point forward, when I say pack a bag, I mean only your toiletries. Unless specified otherwise."

I was dumbfounded. It seemed like a setup, a hot one, but a setup no less, not to mention she expected my default attire in her presence to be nakedness.

"Got a problem with that?" She pressed harshly.

"No, Miss Jessica."

"Good." The ice rattled in her glass as she polished off her drink. Miss Jessica looked down to see me still in my clothes. When her eyes came back up, they were disappointed. "You're not ready for the pool."

"Sorry, Miss Jessica." I apologized and took my shirt overhead before removing my shoes and shorts.

"No. Everything." Miss Jessica ordered, referring to my boxer briefs.

So I removed those, too, exposing my nearly full erection.

Miss Jessica grabbed it immediately and tugged me forward so that the only space between us was the seven and a half inches of my cock.

"I told you to be a good boy, Hunter." She reminded me of our conversation earlier. "Are you going to be a good boy this weekend?"

My cock twitched, and my lungs nearly spasmed as well.

"Yes, Miss Jessica."

"Then do everything I say. I promise..." Her hand migrated down to cup my balls, squeezing them. Her lips went to mine for a quick kiss. "I promise I'll make it worth your while."

And with that, Miss Jessica released me and turned to the door. She pulled at the strings of her top as she walked away and removed it.

"Come on, Hunter. Follow me." She sang as she dropped it in the doorway and vanished from my sight.

I followed again with a twitching cock, down the stairs, along the hallway towards her kitchen, where there was a collection of liquors, mixers, fruit, and a bartending set on the granite countertops.

She took a shot glass and filled it to the top with Ketel One.

"You need to catch up." She held it out to me as I covered the remaining few feet I was trailing her by.

I took the glass eagerly and knocked it back, letting the alcohol sting my throat. Miss Jessica was ready with another one as soon as I set the glass back on the counter.

Remembering the little talk she gave me upstairs, I took the second glass and swallowed it quickly. The burning increased, but it did nothing to quell my hardness. Nor did Miss Jessica's breasts, which were staring me right in the face.

The alcohol started hitting my bloodstream very faintly as I watched Miss Jessica return the glasses to their place.

"Good boy. And since I know you're wondering, I'm a 34DD. And yes..." she grabbed my hand and placed it on them. "They're real."

She smacked it away as soon as I touched them and grabbed a pitcher from the freezer next to us.

"Ever had a margarita?"

"No. I can't say that I have." I struggled, physically incapable of taking my eyes off her.

"Well, you're going to love them. They're perfect for a hot day like this." She explained, dipping her pointer finger in the icy pitcher and sucking its contents off rather seductively. She repeated the process, but this time but held the finger to my mouth and had me suck it off instead.

The finger slid out slowly and was replaced by a slice of pineapple and then a peach which Miss Jessica fed to me.

She then poured two glasses full with the blended margaritas, placed little metal straws in each one, and then handed one to me before returning the pitcher to the freezer.

"Come on." Miss Jessica, thankfully, covered those tempting eyes with her sunglasses and walked out the back door without another word.

Again, I followed. Miss Jessica was the magnet stringing me along.

Her backyard was huge.

Outside the door was a big seating area covered by an open canopy strung with bulb lights. It was surrounded by a large, green lawn and a hedge of boxwood bushes. A little brick and stone staircase went off to the side that led down to the pool.

There was no fence around the yard, like most places around here. Privacy was ensured only by a large ring of trees that flanked three-quarters of her property.

Despite the lack of a real barrier, Miss Jessica strode down those steps topless and proud, underwhelmed by the idea that anyone could show up at any moment- like one of her two sons, her ex-husband, or even her 19-year-old daughter who was only three hours away at Penn State. Nor did it seem to bother her that her new boy toy followed in tow, completely nude and so hard you could hang his cock as a stud to anchor a large wall hanging.

It was quite a rush of both excitement and fear.

But I didn't dare object. I sensed that Miss Jessica would do something mean if I did, like not fuck me.

And I really wanted to fuck her again.

Miss Jessica sat on a lounge chair on the pool deck with a nice white towel draped across it. Another one was right next to it, meant for me. She sipped at her margarita and presented me with a dark brown bottle of sun tan oil.

"I need more."

I took the bottle from her hands and looked at its label, which wasn't what Miss Jessica wanted.

"That means rub it on me. Think you can manage?" She asked derisively, removing her hat and putting her hair up with a clip.

"Yes, Miss Jessica."

"Good. I'm ready." She announced expectantly, laying back on the chair and letting those tits jiggle about like jello before they settled back into place.

With my drink set on the concrete, I pulled my chair closer and sat on the edge, pouring the clearish-gold liquid into my hands.

Miss Jessica's body shocked me, although not with static. The jolt it shot me with was one of memory. My dreams from the last few nights, and the visions I still had of her on top of me in her living room, kept the blood flow heading downward.

Not only was her body as soft as I remembered, but the suntan oil, and the sun above us, made it hot and slippery so that my hands became one with her. I started down at her stomach and worked up slowly to her breasts, ensuring I got sun tan oil on every inch of her skin. I loved the texture they had in my hands; they were so delicate and tender. Her nipples were nice and perky, firm little dots on an otherwise unblemished landscape.

"Do you want to flip over?" I asked after a few minutes, under the impression that I was done with the front side.

"You forgot my legs." Miss Jessica reminded me, extending one of them out and wiggling her toes. "Feet, too."

I began to shift so I could be closer to her lower body, and Miss Jessica perked her head up, sunglasses down around her nose.

"You forgot something else, Hunter...."

My eyes darted up to hers, aware of my sin. "Yes, Miss Jessica. Sorry, Miss Jessica." It felt like overkill, but it was better to be safe than sorry.

I returned to work and repeated the same routine, this time covering her thighs and calves. They were smooth and hairless but extremely fit. Running my hands down the tenderness of her inner thighs, so close to another kind of tenderness, was even more erotic than massaging her topless upper body.

Miss Jessica let me take my time, especially when she noticed how much I focused on her feet.

They each got a minute or two massage, slow and sensual.

I was enraptured, totally and irretrievably.

"That's better. Good boy." She acknowledged and flipped over, which was more arousing than the front side.

The g-string might as well not have existed. Her ass was completely bare, with just a thin little red strap running up the middle and another along the top. Her asshole peeked out from either side, as did the lips of her pussy, giving me more flashbacks.

There were levels to this, apparently. I was only just getting started.

Distracted, I continued applying the oil. I rushed up her calves and thighs so I could take my time with that rear end. Miss Jessica chuckled into the towel that covered her chair and wiggled it around for my enjoyment.