Yes, Miss Jessica Pt. 04

The most prominent sound in the room was my own panting. Just like in my dreams, Miss Jessica had the spotlight. It shone through the big window to the left, as if this was all planned to coincide with the full moon or some goddess like Aphrodite was her stage director.

My wrists tugged at the restraints as I fidgeted under Miss Jessica's looming presence which saturated the air around me.

"What do you want, Hunter?" She whispered in my ear, making my whole body shiver. I lost it when I felt her teeth nibble at the lobe and her tongue swirl around inside. I didn't move too much, though, since my ankles were bound too.

"Gahh...I want your pussy, Miss Jessica."

"Mmm...don't you love the teasing, though?" She kissed down my neck, aggressively at first, and then sensually, before licking her way back up my chin and then locking her lips onto mine for a split second.

"Fuck..." I whimpered, pressing my hips upwards as if I might accidentally, finally penetrate her.

"Hmm? Are you gonna be a good boy and answer my question, Hunter?"

"I love your pussy more."

"Then let me hear you beg for it...."

I felt her slip my head between her slit and grind it back and forth with her hips.

"Ugh...fuck."

"Beg for it, Hunter. Be a good little pussy whipped boy and beg for it."

"Fuck. Fuck! Please, Miss Jessica. I want your pussy."

"You want it?!" Miss Jessica wasn't entertained.

"I need it...."

"Oh, now he needs it...." Miss Jessica patronized me. "Well, you know how to get it."

Her hips kept grinding. I could feel the beads of wetness dripping down my shaft as it slid along the entire length of her pussy, just like it did outside at the pool.

Miss Jessica bent down so that our noses were nearly touching. She took my chin between her pointer finger and thumb again and looked into my eyes.

This was the moment Miss Jessica's lessons started clicking. I didn't just see lust in her eyes- I saw sadism. I saw succubus energy. She was getting off on torturing me, dominating me, watching me capitulate and bend to her demands, confessing things I would never admit if not under duress, all because of the power she held between her legs.

I was in my lizard brain. I couldn't think. I couldn't control myself.

So this was my penance, my lesson. It was all ultimately for my benefit.

The torture was the point.

"Beg."

-

Three margaritas. That's how many I had by the time we went inside. Miss Jessica had three as well.

She had me fetch every one of them for her, along with water and snacks. I reapplied her suntan oil twice and nearly came from the handjob she gave me in the pool and got a stern reminder that I still hadn't been permitted to cum.

Now, I was standing in front of her large walk-in shower in her newly remodeled bathroom, watching the room spinning around me as she started the warm water for us. We were both still naked, and my erection subsided only slightly. I didn't expect it to entirely go away for some time, not until Miss Jessica allowed it to.

She beckoned me to join her with a single finger, which brought the erection back in full force. The warm water hit my sun-kissed skin and spread the feeling of hot gold throughout my body.

Her nails dug into my chin and ass, and underneath the dual shower heads, we began to make out. That tongue of hers went crazy inside my mouth. I have no idea what shapes or patterns she made, but they sent me to the moon. I could've cum just from that- if she let me.

But of course, Miss Jessica wouldn't have it. She pushed me back when she felt me getting too worked up.

"Haven't I been a good boy?" I asked, eager, desperate, and out of breath.

"Ohh..." she made a pouty face. "You've been a very good boy. But you still have work to do."

I huffed and puffed with the steamy water on my back, which did nothing to calm me.

Miss Jessica took a bottle from the shelf next to her and held it out for me. "Wash me."

Without question, I grabbed it from her hand and dumped a fuck load of it all over her chest. There was no reaction from her. She just watched me and stood there as my hands wandered nomadically over everything, sudsing it all up with bubbles from the body wash. I was even allowed to touch between her legs, although it would be the only opportunity I'd have for some time.

Replaying the suntan oil situation, she turned and bent over in front of the wall after I had finished the top part of her body, so I could wash her ass and down her legs. There was no ledge for her to sit or prop herself up, which meant I had to get down on my knees to wash anything below mid-thigh. It was deeply uncomfortable, so I tried to rush through it.

But Miss Jessica was having none of that either.

"No, no." She corrected me as I attempted to stand back up. "You stay down there until I say you're done. Wash me thoroughly."

I dropped back down- or rather was pushed back down by the top of my head- and dispensed more body wash into my bubbly hands.

"Hunter..." I heard her voice get corrective again, in a superior, pedantic way. I looked back up and saw her eyebrows raised as if scolding me gently. "Don't stop being a good boy now. What do you say when I give you a command?"

"Yes, Miss Jessica. I'm sorry." I begged for forgiveness and proceeded to continue her washing.

"It's ok. You're still in training." She comforted me with wet fingers in my hair. "Believe me, I know better than anyone that these tiles are uncomfortable, but you look so cute down on your knees like that."

My erection was so hard it began to hurt as I imagined the things Miss Jessica might have done in this shower. Against my better judgment, I tried to envision them as I tended to those silky legs and feet. It got me into a flow state, and I must have spent several minutes in that position fantasizing about her other exploits before Miss Jessica helped me back up and pinned me into the wall.

"Now, that's a good boy." She moaned, stroking my cock as her soapy body pressed against me. "Are those balls feeling blue yet?"

"Yes. Yes, Miss Jessica. They're aching."

"Aww. Poor boy." She lamented sarcastically. "But I'm so sorry...you still don't get to cum."

"Fuck.." I whimpered. Miss Jessica's hand slowed, no doubt feeling me reaching the cliff of orgasm again. "Can I at least go inside you?"

"You have to help me make dinner first." She informed me over my heavy breaths. "If you continue to be a good boy. I promise you-" that hand slipped from my cock and down between my balls again, with another finger slipping back as far as it could go, teasing my ass. "I promise you. You will get to have sex with me. And you'll get to cum. I've got a special surprise for you."

"Goddamn..." I sputtered. "Is it a good surprise?"

"Oh, of course. It's gonna be fun..." she nibbled at my lip.

"Whew..." I sighed, not understanding that Miss Jessica and I still had very different definitions of the word 'fun' when it came to sex.

"But the real question is: can you keep being a good boy, Hunter? For me?"

"Yes, Miss Jessica."

"Oh, good." She beamed. "Wash yourself quickly, then. And do not relieve yourself. I'll know if you do, and I won't be happy."

"Yes, Miss Jessica."

"Good boy." She patted my cheek and pushed open the glass door.

I was nearly hyperventilating now, which wasn't good considering how drunk I was. In all the commotion, I don't even remember her washing all that soap off. "Fucking shit..." I complained in frustration and heard Miss Jessica cackling as she walked out of the bathroom with her towel around her body, which smelled of orange blossom and rose.

It was unbearable, but I obeyed Miss Jessica's instructions. If this was what she did when I was a good boy, I didn't even want to know what she would do if I upset her.

So I washed up carefully and then joined Miss Jessica back in the kitchen once I was dry.

Thankfully, the erection subsided a little in between, although my balls didn't stop throbbing. The kitchen was filled with Miss Jessica's scent, but the view had been taken away for the time being. Firmly tied around Miss Jessica's body was a hot pink silk robe. At certain angles, as she took ingredients out of her fridge and pantry, I could see between the lapel and get a tiny glimpse of the top of her breasts. But aside from her nipples which poked through the thin veneer, that was it.

I, however, was still not allowed clothes except for a flowery apron, which Miss Jessica had laid out on the counter for me.

I was allowed some things, though:

As she taught me how to make pasta from scratch, I got to hug her from behind- as long as my hands stayed put.

She touched me more, spanking me and groping me lightly every time she passed by.

And that was it.

Miss Jessica's robe mainly stayed in place despite all the moving around, and it remained that way throughout the meal. I was told to lose the apron once the cooking was done, and I spent the entire dinner naked and wishing Miss Jessica was too.

As we ate, in that old, dark house, with nothing more than the open windows and dozens of candles as our source of light, Miss Jessica asked me about my vision for the future- for myself.

"Tell me, my little entrepreneur, what do you want most from this life?" She asked, twirling her finger along my forearm that was resting on the table. "And don't give me some worn-out platitude about just having enough or living a happy life. What do you really want?"

I took my time thinking of the answer. It was hard to search my brain with her looking at me like this, but I wanted to give her something good.

Luckily, Miss Jessica knew just how to drag it out of me. She guided the hand she was tracing shapes on down to her leg and slid it up her robe.

"What do you want from this life, Hunter?" She repeated in a much softer tone.

"I want everything," I replied without any further hesitation.

"Oooh. Everything? Tell me more."

"I want you."

"Ha. I know you want me, silly. What else? Big picture..." She prodded, bringing my hand as far as it would reach, just inches from her pussy.

"Women. Money. Safety. I want to be a force to be reckoned with, with a big company and the ability to do whatever I want, when I want." I confessed. "I want everything the demons that possessed my parents tried to keep from me. I want to make the opportunities I was never given- I want to make them for myself."

"Mmhmm. Scoot closer. Keep going." Miss Jessica enticed me.

I moved my chair to the other side of the table leg that separated us, and Miss Jessica let my fingers move between her slit. She was soaking wet, just like she was out at the pool.

"I want to build a good life for Lauren and me...." I trailed off.

"Mmm. Good. Good." She nodded, letting me run my fingers through her, basking in the slickness.

"I want to be important. I want to be immortalized. Like all those people in the history books we read in school."

Miss Jessica inched her way in, her face illuminated by the mixture of candlelight and moonlight until I could feel her energy on top of me, washing over me.

"I see it." She smiled. Miss Jessica smiled a lot over the course of our relationship, but this one was my favorite- because it was the most genuine. It's frozen like a flash frame in my memory. There was nothing but warmth and truth in it. She meant what she said.

"Yeah?"

"Yeah." She nodded. "You're a rare soul, Hunter. You will be everything you've ever dreamt of and more. And I'm going to help you."

"How do you mean?"

"I'll help you." She repeated without any further explanation. "But if I help you...could I have you as my little plaything? Could I use this cock to get what I want?"

One by one, Miss Jessica's fingers wrapped slowly around my shaft, and she began stroking me. Again.

"And what do you want?" I asked timidly, my vocal chords shaking.

"I just want to have fun with you." She grinned wickedly. "What do you say?"

I nodded my head in agreement, happily, eagerly.

"No. What do you say, Hunter?"

"Yes, Miss Jessica."

"There's my good boy." Miss Jessica praised me. "It's time to finish your first lesson, then."

She released my cock and stood from her chair, undoing the tie on her robe and letting it fall to the ground.

"Come on..." she taunted me and walked out of the room towards her stairs. I hurried up from the table and followed her like a little puppy dog.

The path she took me on led back up those creaky, wooden stairs and into her bedroom.

When I arrived, she was already there in front of the bed waiting for me with a whiteboard and marker.

"Sit." She said, without looking up from whatever she was writing.

"Yes, Miss Jessica." I complied, sitting exactly where she told me, waiting for the surprise she mentioned earlier.

Miss Jessica finished writing and turned the whiteboard to me. There was a list on it, in black marker and her perfect, elegant handwriting:

Deep throat your dick

Anal

Let Miss Jessica have her way with you

Across the top, read a simple sentence: "Good boys always get rewarded."

"You see this list, Hunter?" She asked, checking my attentiveness.

"Yes, Miss Jessica."

"Good. Now, you are a very good boy. You've got a wonderful blueprint...but we need to work on you a little bit." She began, talking as if she was teaching a kindergartner instead of a young man. "And since you're a very horny boy, we're going to start with sex. I have three tasks for you tonight. If you follow my instructions and do as I ask, you will get to do every single one of these things with me tonight. Understand?"

"Yes, Miss Jessica."

"Good boy. Now, read that sentence at the top for me, please. Out loud."

"Good boys always get rewarded."

"That's right." She affirmed, nodding along and clearly expecting me to do the same. "I reward good boys, and I punish bad ones. Do you want to find out how I punish boys who disobey me?"

"No, Miss Jessica."

"No. No, you don't." She shook her head. Miss Jessica then bent over in front of me, her hands resting on my knees. I couldn't help but look down at her tits as they dangled towards the floor- until Miss Jessica corrected me. "So I'm going to confirm with you one more time...you're going to be a good boy for me, aren't you, Hunter?"

Miss Jessica nodded as she asked the question.

"Yes, Miss Jessica." I mimicked her.

"You're not going to disobey me?" - and she shook her head as she asked this one.

"No, Miss Jessica." I mimicked her again.

"Never?"

"Never, Miss Jessica."

"Have you ever done anal, Hunter?"

"No, Miss Jessica."

"You want to fuck me in the ass? I won't even make you wear a condom. You can cum in there if you want. It's so tight...."

"Yes, Miss Jessica. I want to."

"Well, maybe you will." She turned and bent over in front of me the other way, nearly shoving her ass in my face and spreading it so I could see one of the prizes with my own two eyes. "It's right here waiting for you."

Against my better judgment, I reached out and touched it- only to have Miss Jessica turn and smack my hand away so aggressively it stung for the next thirty seconds.

She turned back around, shaking her head again and wagging her finger at me.

"Careful, Hunter. Remember the promise you made me."

"I'm sorry, Miss Jessica."

"You've done very well at being obedient to me, but it's about skill now." She continued, handing me the whiteboard, facing it towards her, and starting to make her expectations clear. "So, eyes on me. Look at my body. Look at every inch. Tell me what you see- in vivid detail."

My eyes wandered over her as requested. It was a full moon, and her window was wide open, just as it was earlier. There was no other light in the room, which meant her entire body was bathed in that pale white moonlight, just like she was in my dreams.

She stood there naked, with her hands on her hips, waiting for me to fail.

I was hard again and felt like I'd been kicked in the balls a hundred times as my hormones threw a temper tantrum at still being denied pussy, and having to work to get it at some undisclosed future time. Much to both of our disappointments, it gave me no words- none that Miss Jessica was expecting, at least.

"You are just...so fucking hot...." I strained, unable to come up with anything else under this pressure- ironically enough for a former athlete.

Miss Jessica scowled at me like an angry school teacher, and I was a student who was acting up again.

"I'm going to give you one more chance to give me something better than that." She warned cryptically. "Describe me. Describe my body. What do you see?"

I panicked. I had absolutely no idea what she wanted, and I was beginning to discover what happened when I didn't meet her expectations. It was horrifically thrilling, and I hated how much it turned me on- and how helpless it made me feel.

"I don't know... Long legs. Big boobs-"

"Tsk tsk tsk...." Miss Jessica clicked her tongue and walked forward at the sound of the first three words. I felt the terror now, precisely as she intended, with my stomach dropping and nerves firing on all cylinders. I expected she would erase something from the list or something even worse than that.

But Miss Jessica wasn't done.

Not even close.

She grabbed the whiteboard, forcefully snatching it out of my hands and tossing it behind me onto the bed.

"Touch me." She demanded, now standing between my legs, just inches from me. "Touch my body, Hunter. Touch me everywhere."

I placed my hands on her carefully, nervously.

That wasn't good enough.

She put her hands on top of mine and pressed them into her. "Touch me like you mean it. I'm not gonna bite. Not yet, at least."

So I touched her again- and meant it.

I started at her stomach, waist, and buttocks, and then down her legs. My forehead got flicked as I tried to take one of the breasts dangling in front of my face into my mouth.

"I said touch me." She reminded me. "Tell me, Hunter. What do you feel?"

I took a few nervous breaths, mulling the possible answers in my head, still unsure of the proper one. "I feel your skin. Your ass. Your breasts."

"Yeah, I know." She replied sarcastically. "What about them?"

"They're soft. Squishy."

"That's better...tell me more. I said in vivid detail. Describe them to me."

I tried, but my brain just wouldn't work. All I felt was boobs, an ass, legs, and a pussy I still wasn't allowed inside.

"I'm sorry, Miss Jessica. I don't know what you want me to say." I apologized, bowing my head with closed eyes into her stomach.

It only rested there for a single second. Miss Jessica's hands braced either side of my face and pulled me back up.

"Look at me, Hunter." She ordered. I looked up to see those comforting cobalt-blue pupils dim a little from the pale light. They were still instructive and demanding, but they had softened now and looked at me like a young child learning about the world for the first time. Still, she didn't accept the failure. "Let's try it this way and see if you can redeem yourself. What do you want to do to me right now?"

"I want to fuck you."

She shook her head slowly and with true disappointment in her eyes which scared me to my core.

"A woman's body is a work of art, Hunter. It's erotic and inspiring, and so are the things you do to it during sex. You can fuck me in the ass and get your cock deep-throated when you describe those things in nothing less than language fitting of poetry."

"Yes, Miss Jessica," I answered, as she let me go and grabbed the whiteboard to erase those two items from the list as I watched.

The next thing she did was straddle me.

"Oh fuck..." I gasped, holding onto her hips for dear life as that aforementioned pussy enveloped my cock lengthwise- but still not letting it in.