Yes, Miss Jessica Pt. 02

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The story of my 3-year relationship with an older woman.
5.3k words
4.72
18.5k
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Part 2 of the 4 part series

Updated 06/11/2023
Created 10/11/2022
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Miss Jessica carefully pulled the head of the gold zipper up her back. Looking into the mirror, she surveyed her appearance. Her beach blonde hair was lightly curled. Her bright blue eyes clashed with the bright, crimson red of the form-fitting, professional-style mini dress. It cut off just an inch or two below her cheeks and somewhat matched the light pink freckles on the other ones.

To the unperverted onlooker, she looked as if she was about to step into the boardroom and command the attention of a group of older white men in some important meeting.

Except she wasn't.

Underneath that dress was nothing but a jet-black bra to keep her DDs from weighing down the top of the dress. It was lacey, sexy, and highly revealing but hidden beneath the thick fabric. The cleavage of this dress still showed off those beautiful breasts, but not as much as the top she wore to coffee with Hunter on Saturday. She revealed a lot to him that day. Tonight, she wanted to scale it back a little, to tease him, and make him wish he could see more.

There were no panties. Miss Jessica didn't wear them with anything but jeans and other hard-fabric pants or slacks.

In the two years since her divorce, she had embraced her sexuality fully. That meant being sexy in everything; in her opinion, panties weren't sexy unless they were lingerie. She loved feeling bare and exposed down there, especially during situations like tonight when she'd be taking Hunter out to dinner so that she could continue slowly seducing him.

She plucked the lipstick from the countertop, removing its shiny gold cap to reveal the equally crimson red, waxy lipstick inside.

Miss Jessica stared intently at her reflection as she meticulously applied it to her lips. It coated them evenly, changing the shade entirely to one that was equal parts striking and sexy. She positioned it in the pocket of her clutch and then dabbed the corners of her mouth with a little napkin.

She walked out of the bathroom, clicked off the light, and sat on her bed. Her feet, with their French tip toes, slipped into a pair of closed-toed, matte gold pumps. A shiny gold watch sat around her wrist, along with some simple gold diamond earrings in her ears. They glimmered in the incandescent lights of her bedroom, flickering in the mirror of her armoire while she sprayed her enchanting perfume about her.

Those heels clacked along the hardwood floor of the large, two-story house she got in the divorce. First, out of the bedroom. Then down the hallway, and the stairs, until she reached the foyer.

As she reached the door, she did one last check of her appearance in the guest bathroom mirror that sat just inside the entryway. She smiled, sure that she had put together another ensemble that Hunter would be helpless to resist.

She was going fuck him tonight and figure out exactly what she was working with.

Miss Jessica pulled up to his house on Fairview five minutes before 6. The heels clicked again up the concrete, followed by the knock of her knuckle against the slate blue, wooden door.

When it opened, Hunter was noticeably taken aback by her outfit.

"Wow. Hi." He said in shock, those green eyes glued to her like he was afraid she'd disappear if he looked away.

"Hi, Hunter." She smiled, scanning him head to toe like he did with her. "You ready?" She perked her eyebrows up.

"Yeah. Absolutely." She stepped aside to let him exit the house and saw his sister Lauren peeking around the corner. She gave a friendly wave, the one where her fingers moved back and forth rapidly, along with another smile.

Hunter looked back and chuckled. "Bye, Lauren."

"Bye. Have fun..." Lauren said, sounding like she had a suspicious attitude about her.

Hunter shut the door and locked it while Miss Jessica did another scan of his outfit. He had done a pretty good job on his task of dressing up. It seemed to be the same suit from his graduation ceremony last year, but it fits him well. He wore black shoes with it, clean Oxfords, and a silver Omega Seamaster that looked a single chain link too big. The distinct smell of Creed's Green Irish Tweed permeated the air and clashed with her own scent: Don't Be Shy, by Kilian.

Hunter caught her looking as he turned back around. She lingered on purpose. She wanted him to notice.

"You look good." She complimented him.

"Thanks. You do too." He returned, unable to be shy about his eyes.

"Hmm. Come on." She chuckled, grabbing his hand and leading him down to the white Mercedes SUV at the end of the walkway.

She left him at his door and kept his gaze as she walked to hers, clicking the doors unlocked with a single electronic beep.

They settled into the dark gray leather seats. Hunter's eyes kept darting over to her. She knew he was baited when she caught him struggling not to look at her tits when she approached him at the gym. The coffee date only served to pull him along, like a good little puppy chasing a treat. She was just toying with him tonight, making him desperately, painfully horny.

It was fun doing that to guys his age.

She kept her legs spread wide, knowing full well he was looking. The freshly shaved pussy beneath the hemline was growing wetter by the second. Playing these games made her feel more alive than she's ever been in her forty-five years on this earth.

Hunter, in particular, had her feeling like a powerful, dangerous woman. The sense that he would be more than just one of those flings continued to set in with her as the sporty engine whirred, and they sped off.

"You like Italian?"

"I do."

"Good. A girlfriend of mine and her husband own a little place just a few minutes from here." They pulled up to a stoplight, and they each turned to face each other. "Do you like red wine?"

"Never had it. It's kinda hard to drink when you're not 21, and high school parties aren't known for their wide selection of reds."

"Haha...mmm." She laughed promiscuously, tugging gently at her neckline with a single finger, bringing his attention to it. "Well, don't worry. You'll like it. You can't have Italian without wine."

"Sounds good."

"Hmm." She laughed again, keeping that eye contact until the light turned green. Hunter attempted to adjust himself discreetly, obviously having lost a fight to his potent hormones.

It wasn't discreet, though. Miss Jessica noticed it, and it increased the wetness that was building up between her legs.

The restaurant was a quaint building with an authentic feel. It was small, but the material that made up its structure felt as authentic as you'd get for suburban Philly. Vines grew on the outside of the building, and a little wood sign hung above the entrance with an Italian flag and the name "" etched into it.

It was a popular place, even for a Tuesday. People were already waiting outside just to get a table for the dinner hour.

Miss Jessica rubbed Hunter's arm in approval as he held the door open for her again. Inside was a lively, spacious dining room, dimly lit and filled with the smells of Italy.

"Hey, gorgeous." A beautiful, olive-skinned woman with dark hair came from around the hostess stand and gave Miss Jessica a hug. "This must be Hunter. Miss Jessica here has told me so much about you. I'm Fiona."

She extended her hand to him, and he met it for a handshake. Hunter didn't know what to say back and settled on the cliche, "All good things, I hope."

Fiona and Miss Jessica laughed enthusiastically, touching each other in a very friendly way.

"Let's get you to your table." Fiona grabbed some menus and ushered them down the aisle. "I like this one." She whispered to Miss Jessica as she walked past her.

"I do too." She replied with a wink.

Fiona led them to a small table near the back, partially secluded from the rest of the dining room. It had a candle in the middle and a vase of colorful flowers like the rest of the tables.

She presented the setup and stood back to let them take their respective seats.

"You want to start with your usual?"

"Yes, please. And a glass for Hunter too." She said softly.

Fiona grinned and pumped her eyebrows a few times as if she understood what was going on. Which she did.

She returned with the glasses rather quickly, almost like she had them prepared already, along with a bottle of wine with a sleek black and orange label.

Miss Jessica wrapped two of her fingers around the stem of the wine glass and stared at its dark red contents. With her head still angled down, her eyes shot up to Hunter. Her grin became devilish as she picked the glass up to display it for him.

"This is the Lambrusco grasparossa di Castelvetro. Taste it." She instructed him.

Hunter did as she requested, taking the glass to his lips and the wine into his mouth. He swallowed it quickly.

Miss Jessica laughed. "No, no. Slowly. Enjoy the flavor. Like this." She closed her eyes and lightly sipped at the glass, letting the velvety wine pass between her lips and onto her tonight. She slowly swished it around in her mouth and then swallowed, opening her eyes to catch Hunter staring as if hypnotized by her every movement. "Your turn."

Hunter again obeyed, mimicking what Miss Jessica did as best he could.

"Take it in your mouth slowly. Enjoy the taste." The double entendres made her pussy tingle, as did watching him follow her every instruction. He was confident and probably pretty hard-headed, but he appeared moldable. "That's good." She smiled. "How do you like it? "

"It's good. Very sweet."

"Just the way I like it." There was another one. She felt a bead of wetness drip out from her inner labia. "It's gonna help make our night."

"What do you mean?"

"We're going to have fun tonight, Hunter. Just you and me."

Hunter's chest was rising and falling more rapidly now. She was making him anxious, and she fucking loved it.

"Sounds good to me." He agreed.

"Good. I'm glad you think so." She took another sip of her wine, using the silence for dramatic effect. This time her eyes stayed open, keeping Hunter's trained on them and pulling him in deeper. "So, did you know my daughter Julia? You two were in the same graduating class."

"No. She and I weren't really that close. I knew of her, though. What is she up to now?"

"She's running cross country at Penn State." Miss Jessica answered. "I'm surprised you guys weren't closer. You're the kind of guy she tends to like."

"Well, I was in a relationship with the same girl from eighth grade until just before graduation," Hunter explained. "So I wasn't really looking for that."

"Aww. That's sweet." Miss Jessica gushed. "So what happened with that girl?"

Hunter was surprised by the question. His aura became suddenly guarded, and he was shaking his head. "You know, sometimes things just don't work out."

Miss Jessica understood exactly what that meant.

"She broke your heart." She peeled the onion back, exposing that next layer for him.

"Yeah."

She made a pouty face to feign sympathy and took his hand like she did at Starbucks on Saturday. "Did you guys sleep together?"

His face changed a bit. He was surprised and slowly wrapping his brain around Miss Jessica's increasing forwardness.

"Yeah. We did." He answered begrudgingly. "We lost our virginity to each other during freshman year. We hooked up a few times a week throughout most of high school."

"Mmm. I'm sorry. That must have been tough." She consoled him and then sat back in her chair with her glass in hand. "So, how many girls have you been with since then?"

Hunter laughed, his eyes wide at Jessica's increasing boldness.

"Come on, now." Miss Jessica implored him. "I know guys like you. You're handsome, charming, intelligent, spurned by a woman you loved."

"Fuck..." Hunter chuckled, sucking back more of the wine.

"Come on..." Miss Jessica pressed. "You can tell me. We're both adults here."

"Fine. But only if I get to know a little about you, too."

That really got her pussy going. She could tell he had been holding back with her, but now that her intentions were more or less clear, his true nature was starting to come out. He no longer felt like he was risking embarrassment, a lecture, or a drink in his face if he got forward and aggressive with her.

"Mmm. There he is. I'll tell you whatever you want to know, sweet boy." Miss Jessica agreed. "But you first."

"13."

Miss Jessica nodded with pursed lips, impressed but still of the mind that he was capable of a better number than that.

"13 girls. All while building up three businesses, fighting for custody of your sister, and caring for her. That's not bad."

"Thank you." He bowed his head.

"So, were they all around your age?"

"More or less. All above 18, obviously."

"Mmm. Which one was your favorite?"

"Danielle."

"Ooh. Tell me about Danielle." She prodded, crossing her legs the other way and feeling the soft squish of her lips down below.

"She was one of my best friends back in middle school, just after I moved here. She and Courtney both had a crush on me, and I chose Courtney." Hunter explained. "So after Courtney and I were done, I called her over to apologize, and we fucked in my bedroom. We hooked up every day until she left for college. We still do sometimes."

Miss Jessica was in love with that answer. She could feel Hunter's heart in it. It was the heart of a man who wanted to rise above his pain and be like her: wild, free, and able to manifest every good thing he wanted.

"I love it." Her voice was low and promiscuous now. Hunter hasn't taken his gaze off her for the entire conversation. He was eating right out of her hand. "So, what do you want to know about me? Ask me anything."

"Forgive me if it's too personal, but I noticed you're not wearing a ring. You're not married?"

"No." She began, "my husband Andrew and I divorced two years ago. Since then, I've been living a lot like you....having fun."

"So, how many guys have you been with since then?"

Miss Jessica bit her lip and blushed, laughing a bit maniacally and with a bit of guilt. "Hmmm..." she moaned. "9."

Hunter had the same reaction she expressed at his number, although he surely thought it would be a bit higher.

"And 5 girls." She finished her glass and poured them each another as Hunter grappled with Miss Jessica's bisexuality.

"Really? "

"Mmhmm." She replied nonchalantly as the deep red libation filled their glasses once again. "Fiona was my first. I've fucked her husband too. They're swingers."

"Wow. Ok. I definitely wasn't expecting that."

"Mmmm." She grinned sadistically, her tongue between her bright red lips. "You'll come to expect the unexpected with me, Hunter. But you'll love every second of it."

-

I felt the unmistakable temptation behind Miss Jessica's eyes as they sunk into me. Our conversation had me uncomfortably hard, but I was given a moment of relief when Fiona showed up with our appetizers.

A plate of beef carpaccio was set on the table, along with bruschetta drizzled with a balsamic glaze and honey. Strangely, I don't remember us ever ordering anything. Nor were we given menus.

The lineup for the evening was clearly pre-selected.

"You two enjoy." Fiona chimed and then leaned down to Miss Jessica. "I'll have the entrees out shortly."

"Thank you, girlie." Miss Jessica returned, grabbed a thin slice of raw beef on her fork, and held it up to me. "They make the best beef carpaccio. Here. Try it."

I reached forward and took the meat in my front teeth, pulling it back into my mouth with my tongue.

"Good, right?" Miss Jessica prompted me, gracefully taking a slice between her teeth.

"It's good," I confessed. "I have another question for you."

"Shoot."

"What's the craziest thing you did sexually during the last two years?"

Miss Jessica beamed at the question, looking me up and down like a piece of meat.

"I like you. Let's see." She sucked in and toyed with her neckline again. "It's hard to narrow it down. I had a threesome with Fiona and her husband. An all-girl orgy with her and a few friends. And I got spit-roasted by two guys on a trip to Mexico. To name a few."

Holy shit.

"Pff." I blew air through my lips. "Damn. Ok."

Miss Jessica's eyes kept evolving. They were demented now, like a succubus eyeing the prey she's already caught and is toying with.

"Like I said. We're gonna have fun."

My erection was pushing hard against my boxer briefs and dress slacks. It was the most turned-on I had ever been. This woman was sexy, uninhibited, and dangerously seductive. I couldn't stop this train even if I tried. Not that I wanted to.

We continued picking at the carpaccio and crunching down on bites of the milky, sweet, and tangy bruschetta.

Fiona dropped off the entrees a few minutes later. Just a few minutes through the meal, the bottle of red was empty, and another took its place.

I had already sensed weird energy between them, but I looked at Fiona much differently after hearing Miss Jessica explain their relationship. She was also a remarkably, naturally beautiful woman. Her dress was teal and white, flowing and long, but it delightfully accentuated her curves. Her breasts weren't as large as Miss Jessica's, but they were perky and still good-sized.

The bounce and the little pokies on her chest showed she wasn't wearing a bra.

She caught me looking. Rather than get upset, she was flattered and winked at me before walking off once again.

Miss Jessica caught me, too but said nothing.

At the end of the meal, there was no check to settle. Fiona came and collected the dishes and left us alone.

"Do you like mini golfing?" Miss Jessica asked.

"Absolutely. I'm pretty good at it."

"Oh, we'll see about that." Miss Jessica responded competitively. "Come on."

"Are you good to drive?"

Miss Jessica didn't answer. She simply looked at me, disappointed I was square enough to even ask such a question.

"Come on." She took my hand and led me out of the restaurant. There was no goodbye to Fiona. There were no leftovers taken, and the tab still wasn't settled.

We went straight back to her Mercedes. She didn't let go of my hand until we reached it.

The drive to the mini golf center was much different than the drive to the restaurant. It was dark now and finally cool. Miss Jessica rolled down the windows and cranked up the music. It was the music my generation listened to: pop, rap, and hip-hop.

I watched her the whole time she drove. Her hair was blowing in the wind, and she sat back, relaxed, twirling it with one of her fingers. I was pretty sure she was at least tipsy, but here she was without a care in the world. She was just living life, being herself without shame.

She was a genuinely enchanting woman but in a lustful, fleshy way. Her allure was more than skin deep, but her essence was purely sinful. There was no wholesomeness or holiness with Miss Jessica.

Miss Jessica wasn't an angel, but her gift was making you feel like she was.

We parked in the spot, and she redid her lipstick before handing me that same silver credit card I had seen at the coffee shop.

"Oh, that's ok. I can cover the mini golf." I offered.

"Ha. You're cute. But no." She insisted and then led me by the hand into the big, multicolored building to begin the activity portion of our date.

By this point, I wasn't fully aware that Miss Jessica was the one in control. I had just learned that with girls, sometimes it's better to go with the flow.

So I followed her up to the counter, holding onto her hand, walking next to her but somewhat behind. I waited patiently as she got our clubs and balls, which she handed to me.

We made our way out to the course and began the first hole. My dirty mind, still reeling from the conversation at dinner, sexualizes everything as we hit balls into holes with giant sticks.

12