Stella

I was tempted to stay up talking to Stella, but it was getting late and I did need to catch an early train. Reluctantly, I said goodnight to Stella and headed downstairs after gathering in an innocent goodnight kiss. I had a big day the next day, but I knew what would be running through my head all day.

*

I was at the Mount Kisco train station early the next morning and studied up on my part of the presentation as I commuted down to Grand Central Station. The day was a busy one and very productive. All the members of our team assembled at the project manager's office and we parceled up our presentation and did a couple of dry runs. I was invited to hang out with the rest of the team after hours - to head out on the town for the evening - but I declined and said I had made plans to see friends.

I had received a couple texts from Stella during the day, just confirming where she had made a reservation and checking on timing. My social secretary was keeping me apprised of our evening's activities, but she was also making me excited for the day to end.

I was on the 4:30 train and back in Kisco by 5:30. I had texted Stella to my ETA. After a short ride I was pulling through the gate and up the driveway to an adventure that had little clarity in my mind at that moment. All I knew was I was going out to dinner with a gorgeous young woman for the evening and the chips would land where they would. I tried to drive the thought that she was my best friends' daughter out of my dirty little mind.

I let myself in the house and found Stella in the kitchen reading the newspaper at the large granite island.

"I'm home, honey," I joked.

"And right on time. Welcome back."

"Should I change into something more comfortable?" I was still wearing a jacket and tie and felt like I would be overdressed for a Wednesday night in Mount Kisco. But once I saw how Stella was attired I realized I didn't want to dress down too much. She looked like a million bucks.

"Sure, but you look pretty dapper the way you are. Maybe lose the tie and we're good to go," she suggested. "Our reservation is for 7 at a place called Winston's downtown. It only takes 10 minutes to get there. Freshen up and come upstairs for Happy Hour. It's on the house," she grinned.

As she spoke I finally had an opportunity to check her out. She was wearing what could best be called by its popular moniker - a little black dress. And where she had looked casual and flouncy the previous night, she looked sexy and exotic on this evening. She was wearing heels that had thin straps around the ankle and the dress itself was tight and showed off her considerable curvature.

"Damn," I said as I made no excuse for looking her up and down. "You look like you must have a hot date tonight," I joked. She smiled and I thought I was going to melt.

"I do, in fact, and I'm looking forward to it."

I excused myself and went downstairs. I took care of business, changed my shoes, put on a fresh shirt and splashed on a little cologne. I was ready for the evening's activities. I emerged from my lair as Stella was mixing martinis.

"Do I need a coupon for this free drink?" I inquired. Stella looked up as she picked up the shaker and gently shook the ingredients on ice. The upper slopes of her breasts shook just slightly with the effort and I shook my head in amazement.

"First one's free," she chimed. "Actually, we only have time for one shorty, then we should be on our way."

She poured a small drink into a fancy glass and handed it to me. We toasted.

"Just enough to wet your whistle," she purred.

I really needed to check my libido. I was reading subtle sexual nuances into every word she said. It was hard not to, however, given how incredibly hot she looked.

"You do the LBD proud," I stated, disregarding my own rule immediately.

"You like? I threw it in my suitcase when I left - just in case."

"Sure. Why not? It can't have taken up much room."

"You're quite right. It doesn't," she agreed with a smile.

We laughed and bantered as we sipped our drinks, but were out the door on time. She tossed me the keys as we descended the stairs to the garage.

"You okay driving Dad's Mercedes convertible?" she inquired.

"I think I can handle it, thanks."

She got in the car and the dress rode sinfully up the longest smoothest legs I had seen in some time. I was going to have to make sure I concentrated on the road and not the sinuous thighs now on display. We backed out of the garage, careened gently down the driveway and pulled out on to the open road. Stella had put her hair under a baseball cap and looked like she might be ready to go for a jog in her tiny black dress.

We parked in the rear of the restaurant and closed up the top. I veered around the rear bumper to open her door - partly to be a gentleman and partly to get an eyeful as she emerged from such a low slung vehicle. She took my hand and kept her lean thighs together properly as she swung and stood. The hat was gone and she looked like a movie star arriving at a premier.

"Why thank you, Jake. I hope you'll throw your jacket down if we come to any puddles."

"You know I will," I responded.

We entered the restaurant and were seated immediately up in the mezzanine at a very private table for two against the exposed brick wall and directly above the bar. It was a perfect table for a private conversation. We were right in the middle of things and could see the entire restaurant, but had no other tables nearby.

We ordered two proper martinis and perused the menu. The drinks were brought promptly and the waitress took our order efficiently. We toasted to what felt like the beginning of a wonderful evening.

I had noticed a few looks from patrons and the hostess as we had entered the restaurant. It was a hip young place and I had to figure that Stella might run into someone she knew. I was hoping my presence was not going to embarrass her in some way.

"I hope you're okay being here with me. It feels like the kind of place you might know someone, seeing as you grew up here."

She looked up at me and squinted like I was crazy. "Don't be ridiculous. I love being seen with a handsome older man." She raised her glass and smiled as I melted a little further into my chair. "And besides, I like it. Let them all wonder," she said with a lascivious grin.

Our conversation was free-wheeling to start. She asked me about my day and how the prep for the interview had gone. She brought me up to date on how things were going at law school. But as the buzz of one and a half martinis began to take hold, I could feel both of us relax. Our first course arrived and Stella began to ask me questions.

"So, how is life for you now - post-divorce, and all?"

"It's fine. It was probably as amicable a divorce as could be. I'm still working hard and that seems to continue to consume most of my time."

"Well, I guess I should be more specific. How is your private life, post-divorce...if you don't mind me asking?" I smiled at the question. She seemed to be very curious and I didn't mind going where she seemed to be leading us with her question.

"It's good. Strange being single again after 30 years of marriage. But I've rather liked it, I have to say. It's a bit strange getting back into the dating scene, but very exciting as well."

"I bet," she replied. "Do you have a girlfriend?" she asked bluntly.

"No, not really. I mean, I have a few women I date. I find I'm rather picky and don't just want to go out for the sake of going out, if that makes sense."

"I'm sorry. I'm really being nosey, aren't I?" she stated. "We can talk about something else if it makes you uncomfortable."

"No. It's fine. I'm surprised you find it interesting, but I really don't mind talking about it. I kind of like it, actually."

"Good," she replied. "Because I do too."

This was going in an interesting direction and I felt I needed to be light on my feet and steer the conversation accordingly.

"I do have two requests, though, if we're going to play 20 questions." She smiled and nodded. "First, whatever we talk about here tonight, stays between us. Okay? I'll be totally honest. But this doesn't go back to your parents or anyone else."

She nodded and smiled. "Of course. Goes without saying. And?"

"And second, when you're done, I get to ask you just as many questions."

She shifted in her seat and smiled again. Damn, she was so young and lovely. "Fair enough," she responded. "It's a deal." She held out her slender hand and we shook.

"So...tell me," she continued. "How many women have you been with since your divorce?"

I scrunched my brow as if in deep thought. I looked up at the ceiling and poked my fingers in the air as if I were doing addition in my head. "...carry the six, times four..." She smiled and rolled her eyes.

"You are such a...man," she giggled.

"Guilty as charged," I replied. "You don't happen to have a calculator with you, do you?"

She sighed, smiled and looked at me with skepticism as she tapped her pretty fingers on the white table cloth.

"You are so full of shit," she said

"The answer is seven," I finally said.

She smirked. "All those calculations and that's what you came up with?"

"Yup. Final answer."

"Not bad for two years. Tell me about them."

"Hmmm - pretty broad question. Well, I was celibate for a while after the divorce; didn't really feel like dating. But after a few months I started to need some company, so I had a one night stand or two. Okay, not great. And it made me realize that there are more than a few younger women interested in older men and that I should take my time and choose carefully."

"Sounds logical - and like a good plan. Did it work?"

"It did. I had friends and colleagues trying to set me up, but I used a dating website as well. I was just very picky - and careful - and that worked out. I met some really marvelous women."

"You can afford to be picky - you should be. Were they younger women?"

"All but one, yes. I tried my demographic, but...what can I say. I am drawn to youth. I suppose that's shallow, but...well, it's true."

"I can understand that. I'm not going to judge. Were any as young as me?" she asked with a devilish smile.

"Hmmm - you still have that calculator handy?" I joked. She rolled her eyes and I continued. "Well, yes, in fact. One was...mid-twenties."

"Oh, my. Tell me about her. How did you meet her?"

"Well, it was an erotic writing website - something I've dabbled in from time to time."

"Really," she said, more of a statement than a question.

"Yes. We met there - long story - but we hit it off and she actually lived not that far from Chicago and...we met...a few times."

"And? Was it good?"

"Yes, it was wonderful. I would still be in touch with her, but the distance thing was a drag. And she has a new boyfriend. But it was fun while it lasted. She was incredible." I reflected for a moment as she stayed silent. "You know, we may have grown up in the age of "sex, drugs and rock n' roll", free love and all that stuff. But your generation is so much freer than ours was in so many ways."

"How so?" she queried.

"I don't know. I think you're much less hung up on sexual mores. Perhaps the internet has changed all that, I'm not sure. But I will say my youngest lover was also one of my wildest, most carefree, most adventurous." I looked at Stella as I could see her nodding slightly with a wry grin before she continued the inquisition. I was loving it.

"Are you seeing anybody now?"

"Actually, nobody steady. I have one friend whom I see on a fairly regular basis, but we have an understanding. We're friends, we have good sex together, but it's not going beyond that. She's a gas, but I can't see spending the rest of my life together."

"Will you get married again?"

"Whoa. Tough question. I'm not sure, but I'd probably say...probably. Not right now, but I would like to have a good friend to grow old with. I think that is the scariest thing about aging without a partner...growing old alone."

"What's the best sex you've ever had?"

"Hmmm. That's a loaded question." I thought about the truthful answer, but decided to take a gamble and see how it went. "Can I answer that question before I leave on Saturday?"

Stella smiled wickedly and took a sip of her drink. "Of course. There's a 48 hour limit on all questions." She hesitated. "I have a few more. Did you ever go out with my mom?"

"I did not. She was with your father from the time I first met her. They've been a pretty solid duo as you well know."

"Did you ever fantasize about her?"

"Trick question. Well, in the early days, yes. She was a looker - still is - just like her daughter." I paused and looked at Stella carefully. "You have many of her best qualities - her inner and outer beauty. You're certainly as beautiful - and you may even have a better body than hers, though I can't say for sure, yet."

"Yet?"

"Well, you do have a pool and all. I figured..."

"Was she hot in her day?"

"Well, she still is in my book. But, yes, your mother was one of the most beautiful girls on campus - bar none. Every guy on campus wanted her. You're dad saw a good thing and never let go. He's a wise man."

"That he is," she agreed. "Last question. Have you ever fantasized about me?" Her eyes bore a hole in my mind as I steadied myself to answer - honestly.

"Yes," I replied, looking directly into her deep brown eyes. "Last night, in fact," I added, with a visible gulp. She smiled, satisfied with her inquiry. "I feel like I've been deposed. Did you get everything you needed?"

"Yes. I did, though I may have a few follow-up questions for the witness," she said with a glowing smile. "Your turn. "

"Oh my. Where to start?" I figured I should take advantage of every question and garner as much information as I could.

"So, how was your personal life in high school and college?"

"Whoa. Your first question out of the gate is an essay question?" I shrugged innocently and smiled in agreement as she took a deep breath and began. "Well, high school was high school, you know? Groping and awkward moves and back seat explorations. I did lose my virginity senior year, however, to a boyfriend at the time. It was actually in the guest suite where you're sleeping you'll be happy to know," she added with a wicked grin. "College was more of the same - boys and more boys. I dated around, had one serious boyfriend for most of sophomore and junior year. I think I had a pretty typical college experience - experimenting some, but dating around. Nothing too serious."

"And then you took off a year before law school?"

"I did. Moved to New York, lived in Brooklyn, lived hand to mouth. I had a boyfriend that year - it was good. But it didn't survive my move to Ann Arbor and I didn't want it to, actually."

"And how about law school? An active social and love life? A boyfriend?"

She hesitated unexpectedly and I wasn't sure what I had stumbled upon. "Well, yes and no. It's...complicated."

"How so? I mean, you either have a boyfriend or you don't. No?"

"Hmmm. I guess you could say I have...an arrangement. He's not really a boyfriend. He's more of a...friend."

"Sounds intriguing," I replied. "Are you comfortable explaining a bit more? I'm not sure I follow."

"Well, let me explain it this way. Once I started law school, I really wanted to focus on school. I didn't want my life complicated with a boyfriend and the whole emotional attachment thing. I don't know if that makes sense to you, but I didn't want another needy guy to deal with." She hesitated and took another sip of the wine we were now enjoying with dinner. "At the same time I didn't want to be celibate for a couple years. So I...well, you know what a sugar daddy is, right?"

I was taken completely by surprise by this revelation and she could see it in my face. "Well, yes, I do. But, Stella, I mean, your parents must provide well for you and all. Ummm, why?" I could see a look of consternation cross her face and realized my reaction had been wrong. "Listen, I'm not one to judge, believe me. I just want to understand. Try me." That comment seemed to assuage her and she continued.

"Well, I didn't do it for the money, really. But, I have to say, it's really nice. The gentleman I met gives me a nice monthly stipend and, well, I'm spoiled, you know. I like nice things and going out and buying clothes. My parents are generous, but this extra money is really really nice, I have to say."

"Okay. I buy that. But it sounds like there is more."

"Well, yes, there is. I figured this was a nice arrangement for me - no emotional attachment, but occasional dates and enough sex to keep my libido at bay. It seemed like a good idea - and is, in fact. But I guess there was one thing I hadn't considered - a good thing, actually." She looked at me with a teasing expression and I could tell she wanted to keep talking. I lined up my next question.

"And that thing would be" I asked, the question hanging in the air.

"Well, I never considered that the sex would be so incredibly good. That may sound strange; I've had my share of partners. But...I wasn't prepared for how much I would love the sexual aspect of this arrangement. It's been nothing short of remarkable and given me an entirely new opinion about older men." I shifted in my seat at this information and smiled; trying to be casual in my reaction.

"But, of course," I replied. "Everyone knows older men rock."

"Well, I didn't. But I do now."

This was getting very interesting and she knew she had me hooked. I needed to make the rest of my questions count.

"So tell me all about it. I'm fascinated. How'd you meet him? What's he like? Who is he?"

She hesitated as our waitress cleaned up our dinner plates and we decided to share a dessert.

"I met him through this "sugar daddy" website. I know it sounds cheesy, but it seemed like a safe place to start. I was very picky and in no hurry. I didn't want to cast about. I wanted to choose carefully and once. I lucked out. We got in touch, he sounded really cool and we met for coffee. I was hooked and the rest is history."

"Tell me more about him."

"He's a lawyer, ironically - a divorce attorney. His name is Oliver, he's 55 and a partner in a large firm in Detroit. He's married, a grown son, and a really incredible guy. His wife is quite gorgeous, in fact, but too caught up in the Grosse Point lifestyle and sort of not interested in sex anymore. I don't know - I suppose everybody going this route has a different story to tell. But his marriage is for show and he's got, well, a very strong insatiable sex drive. We match up well in that department," she said with a conspiratorial smile. "It's been a great arrangement for both of us - no drama, lots of fun and really great sex."

"What's he look like?"

Stella got a dreamy expression as she talked about her paramour - her sugar daddy. "Hmmm. Well, he's very handsome, tall, slender, and fit. He's got longish gray hair and wears glasses. He's so intelligent and funny - kind...he's just...great. And, to top it all off, he's got the most beautiful penis - hard or soft - just...gorgeous."

"Wow. Sounds amazing. I guess I understand. So, what's the arrangement like? How often do you see him? How long has this been going on?"

"I see him about once a month, sometimes more, usually in Detroit. He'll rent a nice hotel suite or an Airbnb and we'll get together from Friday evening through Sunday. I guess it's been about 18 months or so. It's an added benefit that he's a lawyer and can give me support sometimes on my own schoolwork. And it's nice that it's in Detroit and I don't have to worry about running into people I know."

"What about him?"

"Well, he's careful. We don't flaunt our relationship in public, but we don't hide it either. He's not going to advertise what's going on to his wife, but she is pretty oblivious to his comings and goings, I guess. She lives in her own world." Stella hesitated and I could tell she had more to say. "Sometimes we travel - maybe a couple times a years - and every so often he'll come to Ann Arbor when he just needs to see me real bad. He's been to my place a couple times."