Yes, Miss Jessica Pt. 01

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The story of my 3-year relationship with an older woman.
4.7k words
4.42
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Part 1 of the 4 part series

Updated 06/11/2023
Created 10/11/2022
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Some upbeat Jennifer Lopez song blared through Jessica's headphones as she set her dumbbells down on the bench to end her set. Across the weight floor of the LA Fitness, she spotted a familiar face giving his all on the chest-supported row. Two plates loaded on either side, his powerful arms pulled the handles back in a swift, controlled manner. The emerald green eyes that sat beneath his clean-cut dirty blonde hair had seen the worst of the world. Yet, they stared into the mirror at his reflection, determined to keep those handles and himself moving.

His name was Hunter Ambrose, a former classmate of her daughter Julia. Though she had never spoken to him outside of their familiar nods and waves in this commercialized temple of iron, she knew of him and his situation.

She vividly remembered his speech as valedictorian at Foxborough High just a year ago. It was so emotional, the pain on his face as he spoke of his grandparents' passing was unforgettable. Everyone in the audience felt the suffering of his heart, crying the tears he withheld. He stood on that podium in his maroon-colored cap and gown, stoic and unmoved, young and determined but alone, fighting for his life.

Jessica watched him in the remaining seconds of her rest period, as she had for nearly a year. That muscle shirt basically exposed his entire upper body, with its wide shoulders and booming chest. Even at 19, he was an Adonis, one that made Jessica feel the pull of fate tugging her towards him. He had the presence of a man whose magnificent destiny was written in the stars, but was plagued by mental and circumstantial blocks that kept him in a place he didn't belong.

As she was about to reach down and grab the 15s for her last set, Hunter looked over at her. He likely felt the psychic energy from her leering that said, 'turn around and look at me.'

That, of course, was deliberate.

And it worked.

They locked eyes for a split-second, and she sent him another message with a flirtatious grin: 'you're not leaving here until we talk, Mister.'

Jessica was familiar with his type, having raised two athletic boys herself. Hunter was young, bold, and determined but incredibly naïve and over-confident. If not for her intricate understanding of how young adult men act, those last two traits were evident in the smoldering expression he made back at her. Clearly, his mind was going to places all too familiar for 19-year-old boys.

Good.

Hunter reciprocated her energy, and it sent flutters through Jessica's body. Just to toy with him, she looked away as soon as his eyes set on her.

She took hold of the waistline on her spandex gym shorts. She hiked them up just a little further, wiggling about so that her fit ass would catch his attention. Jessica wanted to give him something alluring to look at instead of whatever he normally did during his rests. Even though she was no longer turned towards him, she could feel his eyes going exactly where she wanted them to.

It would be easy to take him under her wing- and fun.

And since a few minutes had gone by without his sister anywhere in sight, he definitely wasn't walking out those doors before she got her claws on him.

The glances continued throughout their workouts. At one point, she walked right past him and felt his curiosity follow her with each step, carefully watching that ass shake back and forth.

She caught him on the couch near the front desk when it was all said and done. He had a shaker bottle in one hand and his phone in the other, distracted and unassuming.

That was when she made her approach.

-

Just got done with my workout, so I'll be home soon. I'll pick up your prescription on the way. How are you feeling? I texted my sister Lauren.

She's been my gym buddy the last few months, but today she was sick and at home binge-watching our Gran's old rom-coms. My immune system was apparently bulletproof for the time being, so I had escaped it and was still living a free and normal life.

The plastic cap on my shaker bottle clicked open. I started playing Angry Birds to entertain myself while sucking down the watered-down chocolate protein powder inside.

I dragged my finger across the smooth touchscreen and flung that little red fucker towards his target when a faded shadow formed on the laminate concrete floor.

"You were looking pretty good on your bent-over rows." A sweet, moderately toned voice said over the little grunting noises coming from my phone- and a gray and pink Nike shoe kicked my right calf muscle.

I looked up and saw the woman I'd been making eyes with throughout my workout, which is something we've been doing a lot lately. I knew of her from her daughter Julia who was in my graduating class in high school. We've said hi a few times, but since Lauren's always with me, I never struck up much of a conversation. I was never close enough with Julia to get a formal introduction at any point, either. She apparently saw me alone and vulnerable and took that as the perfect opportunity to come make a move.

She's older but probably the fittest, youngest-looking forty-something-year-old I've ever seen. Unless I'm the dumbest guy alive, which I'm pretty sure I'm not, she seemed more interested in me than my bent-over barbell rows.

"Thanks." I laughed and stood up to extend my hand for a formal shake. "I'm Hunter."

"I'm Jessica. It's nice to properly meet you, Hunter." She grinned and reciprocated the greeting, her dainty but confident fingers wrapping around mine.

I was a little lost for a moment, distracted by the smushed but naturally large breasts in her sports bra and her bright, cobalt-blue eyes. I never associated them with that color at the time, nor did I register all the other details I would come to associate with my memories of her- but they diverted my typically sharp mind nonetheless.

She could obviously tell, too. In hindsight, she didn't hide how much she enjoyed watching me battle my biological instincts in our first few interactions. Amusement was written all over her face as I kept myself from glancing down at her cleavage and the slight camel toe in her crotch.

How old is this woman? I thought. I know she's at least 40, but she looks too young to be that much older than me.

"So you're still living around here?" She prompted the next topic, as I apparently lost all knowledge of how to talk to a girl- or woman, in this case.

"Yeah." I jumped into my answer, finally with something else to focus on aside from the hot, glistening woman in front of me. "Same place, actually, over on Fairview. Just across the 75."

"Oh, I love that neighborhood. Are you in school now?"

"No. I've been taking care of my sister. I'm an entrepreneur." I said confidently, still reminding myself to keep my attention trained on only the bright cobalt-blue eyes.

"Oh!" She exclaimed, impressed but also a bit patronizing. "What's your business?"

"I have three at the moment. I walk dogs for people in my neighborhood, and I also taught myself how to design websites and do SEO, so I've been selling those services on my own. My third one is my dream, though. It's an e-commerce brand that I'm doing through Amazon FBA called FIT."

"And what is that brand going to be?"

"It's a fitness brand, mostly attire to start," I explained. "I don't like the way a lot of companies design their gym clothes, so I'm working on a brand that will make something more for your traditional, dedicated gym goers. Once it grows, I think I'll branch out into other gym-related items, but I'm just sticking with apparel for now. My dream is to make it bigger than any of the other household names."

Jessica's face grew more and more impressed throughout the short elevator pitch for FIT. That troublesome smile sent chills down my spine. A part of me knew it wasn't just cordial, but at the time, I disregarded it out of horniness.

"That's really cool." Her smile got bigger. Thank god I was wearing compression shorts. "I'd love to hear more about it. I'm not sure if you're aware, but I'm actually a partner at Penn Capital. I've worked in business and finance for over twenty years. Maybe I could help you...and get to know you a little more."

My eyes grew wide. I wasn't sure exactly what the point of this conversation was yet. Originally, it seems like she was coming on to me, but now it sounded like it might be a business transaction. I was confused, horny, and way too invested in the first possibility.

"Yeah. Yeah, that would be great. Thank you." I replied, sounding as excited as I felt.

"Well, what do you say we grab coffee on Saturday? There's a Starbucks over on Montgomery that should be close for both of us."

"That sounds good." I agreed. I was feeling jittery, but I didn't know if it was leftover adrenaline from my workout or adrenaline from her.

"Well, you'll need my number." She held out her hand to request my phone, which I promptly handed over.

Being the hormonal 19-year-old I was then, I took that as my only chance to finally relieve myself and look at something other than her face. She had a nice one, but fuck, that body made her look like she was still in her 20s. Light tan skin aside, everything was smooth and perfectly toned. Her stomach was flat. Her tits were easily DDs at least. And she definitely did her squats.

She was hot, and there was no ring on her finger either. Was this a date? It sure seemed like it. Either way...goddamn.

"9 am sound good to you?" I snapped my eyes to her face again just before the number left her lips.

"Yeah, that sounds good. I'll see you there."

"Cool. It was nice to meet you, Hunter. See you Saturday."

Yeah, I was still confused, but I turned and watched her walk away. Her back was to me, so I could sneak in another three seconds of ogling without looking like a creep to anyone around. So I did.

After those three seconds, I looked down at my phone, and there was her contact, newly input into my iPhone 4:

Miss Jessica White.

We scheduled our little coffee date on a Wednesday, and Saturday came way slower than I expected. I didn't see her again at the gym except for Friday in the late afternoon. The only interaction we had was in passing. She smiled at me and said, "don't you forget..." in a sing-song voice.

I couldn't place my finger on it, but something about Jessica had me excited to get see her again. Maybe it was because I thought she was flirting and the prospect that I might get to sow my wild oats with a woman of her age. Or maybe it was that she offered to help me with FIT, but either way, I was buzzing when I woke up that morning.

My alarm went off at 7 so I could do some stretching and go for a walk before getting ready, and I put painstaking effort into my appearance. Looking good was usually a big priority for me, but I wanted to bring my best to this coffee date. One perk of being athletic is that really anything looks good on you. So I donned my slip-on vans, some shorts, and a good-fitting t-shirt and sprayed a few puffs of my Grandpap's Creed into a cloud around me, stepping forward to absorb its sweet, but musky scent.

Lauren was still recovering from her cold, and before I left, I went into her room to check on her and found her fast asleep. She knew I had a meeting that morning, so I left her alone to sleep in, sure to be back within the next hour or so.

The Starbucks was tucked back into the strip mall just a bit, but Montgomery Ave was alive and roaring with activity behind me as I stepped out of my car. Its energy fueled my own, and the buzz inside intensified as I approached the entrance. It was five minutes to 9 am, and Jessica was already there, sitting outside at one of the tables- waiting for me.

She looked up from her book and saw me walking towards her, hitting me again with that smile. I knew right away this would be an equally difficult interaction.

She was dressed in a white top that was even more low cut than her sports bra, with her cleavage wide open for viewing. Her jean shorts were short, just like the ones the girls at school used to wear. And on her head was a tan, wide-brimmed summer hat. The entire outfit was something you'd typically see on a woman half her age, but between her complexion and her body, she pulled it off without issue.

Jessica got up from her chair as I closed in and came towards me with her arms stretched out for a hug. I took a deep breath and obliged her. My hands carefully rested on her upper back, not wishing to do anything inappropriate out of misplaced arousal.

Her hands weren't so careful, though. I felt a single set of five fingers lightly rake the skin on the back of my neck just as her breasts squished into my chest. I got a whiff of her perfume next, sweet and sugary, and hoped to whatever gods are out there in the universe that my shorts would keep me from showing any signs of an erection.

She pulled away after a few seconds, and my mind began slipping into a foggy daze, which worsened when I saw her smile again. It seemed devious and seductive. Like everything she did, she did it on purpose to bewitch me.

"It's nice to see you again, Hunter." She greeted me audibly, checking her watch. "And five minutes early, too. I like that."

Her eyebrows perked up as she voiced her approval of my punctuality. All of these things I registered subconsciously, unaware of her game, but they had no less of an effect on me.

"Well, you know what they teach you as an athlete: if you're early, you're on time, and if you're on time, you're late," I answered, feeling her French tip nails resting on the skin of my forearm.

She pulled them forward as if to usher me towards the door. I obeyed and instinctively opened it for her so she could walk in ahead of me. She rewarded me with an even more devious grin as the smell of fresh coffee and the sounds of chatter and the bean grinders hit my ears.

"Remind me, what sports did you play?" She inquired as I walked up beside her.

"Rugby and wrestling, mostly. But I was also the punter and placekicker for the football team."

She turned as we reached the busy, backed-up line and gazed up at me. I'm pretty tall, six-foot-four, but Jessica wasn't too far off at her five-foot-nine. Still, she had a few inches to look up. Normally it's cute when girls do that, but with her, it felt invigorating. Again, I felt those nails on my arm. I lost track of where we were in line and got lost in the conversation instead.

"Oh my gosh, you were the one that kicked that game-winning field goal during homecoming last year, weren't you?" She asked enthusiastically.

"Yep. That was me." I smiled, recalling that moment vividly

"That was your longest kick ever, too. Wasn't it?"

I paused, feeling the rush from her interest in my accomplishments. "Yeah, it was. Good memory." I beamed.

"I went to all those games." She added, the nails digging in a little further before pulling away. "It's a shame I never caught any wrestling or rugby, though. Sounds fun."

"Yeah, rugby was by far my favorite sport. I watched it a lot growing up."

"You have such an interesting accent." She switched the subject as we continued stepping forward. "You weren't born here, were you?"

"No. I was born in Australia. Perth. My sister Lauren and I moved here when I was 12."

"Well, I love it." Those eyebrows perked up again. That smile tested the loyalty of my shorts. The perfume mixed with coffee strengthened my trance.

"Are you ready to order?" The perky barista asked suddenly. I realized we were already at the counter. Somehow. I don't know how we moved through that line so fast. That seemed way too short of a conversation to have lasted that long.

"Yes, I'll have a venti, iced mocha latte," Jessica responded and then touched my arm for the umpteenth time. "Order whatever you want. It's on me."

"I'll just have a tall black coffee, please. Pike Roast is fine."

Jessica fetched the Coach wallet from her bag and flashed the both of us a funny expression as if my order was too cliché for a guy like me.

"Do you want anything else? Get yourself something to eat. Gotta fuel those gains!" She prompted me, squeezing my bicep.

Not willing to deny her gentle command, I laughed and perused the display case that housed their food items.

"How about a sausage and egg breakfast sandwich too." I added.

"Perfect. Anything else?" The barista asked.

"No. That's it, thank you." Jessica answered for both of us, holding on to a silver American Express credit card.

From where I was standing, I could just see inside the right side of her top. She had huge breasts that appeared to be 100% real. A nude-colored bra covered them, but at this angle, I could make out a bit of her nipple. It was an unusually dark pink, almost magenta, and definitely pointed.

With so many eyes around, I couldn't stare too long, but I couldn't help sneaking a few split-second peeks under the guise of just looking around.

The barista smiled at me as Jessica finished paying, probably assuming she was my mom, especially when Jessica again placed her hand on my upper arm and guided me towards the other counter to wait for our order.

It didn't take too terribly long, but Jessica asked me more about rugby and wrestling in the meantime, getting me to talk about my interests.

After collecting our coffee and my sandwich, we sat down at a table outside, per Jessica's unspoken request.

She sat across from me now and commanded my attention with her eyes, keeping me trained on nothing else but her with an intense yet comforting stare.

"You love being...physically active, don't you?" She asked, emphasizing that word in a very intriguing way.

"Yeah, I do. After graduating last year, I got big into weightlifting. I walk a lot, too. Amongst other things."

"Yeah. I can tell." She took a sip of her latte. For some reason, I watched the entire movement, and for some other reason, she never broke eye contact. "So why did you decide to stay around here?"

I sighed and sat back in my chair. "Well..." I paused, gathering the strength to tell the story. "You know my grandparents both passed away last year, just before graduation."

"Yeah. I remember your speech at the ceremony." Jessica's tone became heartfelt. I could see and feel her pity.

"It was unexpected, and they were the only family we had. My sister was 15 at the time, and child services were trying to put her in foster care," I continued, unable to mask the emotions that plagued me from the events of the last twelve months. I sat up in my chair as if that would help. Jessica leaned forward too. "I love her more than anything, and I wasn't about to lose her and let her live that kind of life. So I used some of my grandparents' life insurance money, hired an attorney, and fought the state for custody of her."

Jessica took my hand in hers, mirroring me with her empathetic facial expression and sympathetic eyes. Her lips lowered into a frown. "That's really sweet. She's lucky to have you. Not a lot of guys are as high quality as you."

I simply nodded in response, unable to muster any other words on the subject. I didn't share how I had to work night and day, at the expense of my own emotional health, to help Lauren heal from their death. How I went to one of the Catholic parishes every day to pray the court would grant me guardianship over her. Or how I worked for 18 hours a day building a livable income on my own to help my case.

I felt a squeeze on my palm. Jessica's smile was warm now.

"You're a good young man. You're going to be successful, and your sister will live an amazing life because of you," She comforted me.

A single tear escaped from my eye, and I brushed it away with a laugh. My lip was quivering, too, but I couldn't do much about that, unfortunately.

Jessica continued looking at me, intent on going deeper.

12