Stella

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. I waited until I was 18, believe it or not. 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 Pointe 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."

Stella's face took on a look of shyness all of a sudden, like she was a bit embarrassed.

"Have I told you too much? You must think I'm weird or a slut or something."

"No, no. Not at all. I find this fascinating. Please go on - I love hearing this. Tell me why the sex is so good."

"Hmmm. You're an older man - you know. He's experienced, patient, considerate. I don't think I have ever used those words with my former boyfriends. He just knows how to touch me and is so incredibly attuned to my body. I mean, to be honest, he worships my body and just can't get enough of it. That is such a turn-on for me - the way he looks at me, touches me, kisses me, goes down on me, the way he needs and appreciates me... Just talking about it gives me shivers. He's just so very focused on MY pleasure as opposed to his own."

"Well, I don't like to generalize," I responded, "but I would say that is true of most older lovers - male lovers, that is. A light bulb eventually goes on in our heads about how to treat a woman - how to please them. I think we all wish we'd known some of the things we know now when we were younger. But you have to learn them the hard way, I guess - by aging. Tell me more."

"Hmm - that's not enough?" she asked with a giggle. "Let's see. He makes me cum harder and more than any of my previous beaus. I guess that's what I mean by saying he's considerate. He'll make me cum three or four times with his mouth and fingers before we ever get around to fucking. Once in a while, we go right at it. But most of the time there's lots of foreplay, which I love." She lightly ran her fingers up and down the stem of her wine glass as she waxed on about her older lover. "He's very creative in bed and has introduced me to some kinda kinky things that I thought I'd never be into. He can be incredibly gentle and kind - and then he can turn it up and be rough, which turns me on."

Speaking of being turned on, I realized as we were talking that I was growing hard myself. Hearing my best friends' daughter wax on about her sex life being kinky with an older man had me on the edge of my seat. I decided to share that fact.

"Geez, Stella. This all sound incredible. I'm, well, it's turning me on hearing all of this. I feel a little guilty telling you that, but it's true."

She beamed when she heard my confession. "Really? Oh my - that's so exciting. Well, I'll have to tell you more, then," she giggled. God, her little giggle was infectious and so sexy.

"I think you're running out of questions," she said demurely. It sounded like she'd entertain a few more, so I went for it.

"Just a couple more - I promise. I think I'm up to 15 or something like that."

"Yeah, right. But go ahead," she said quietly and with a shy smile.

"Did I hear something about "kinda kinky things" in there, or was that my imagination."

"You did," she said, demurely with a shy smile. I wasn't sure she'd continue, but she did. "Nothing really crazy, you know, just playing with toys, getting tied up sometimes, blindfolds, plugs, sometimes getting a little rough, some spanking...that kind of thing. It's really not that crazy..."

"Oh my. Maybe not to you. Man, what a conversation." The waitress laid our bill on the table and I slipped my credit card into the leather binder.

"So, what do we do for an encore?" I asked.

"Well, I guess that depends on you," she replied. "Didn't you say you have to get up early tomorrow?"

I did, in fact, need to arise at the crack of dawn so I could be in Manhattan for our 10am interview. But we were all meeting at the PM's office at 8 and I would have to be getting up at 5am or so.

"Hmmm, yes. I do, unfortunately," I said rather glumly. I was struck with an idea as I considered the circumstances. "But I'll be home early tomorrow, you know, if you're not busy or anything. What's on the agenda at the Villa Stella Resort? Cornhole? Bingo? Must be something exciting happening on a Friday night?"

"Hmmm - let me check the schedule." She furrowed her brow as she pretended to check her phone, then brightened. "Oh, look at this. Topless martinis at 5pm. You lucked out."

"Stella, seriously. I...if you have something you should be doing tomorrow night, I'd understand. I'm kinda joking," I said sheepishly, secretly hoping she'd accept my offer. "I know you have old friends to see and all."

"Nonsense. I've seen everyone I want to see. I'm going to spend tomorrow relaxing by the pool. I'll be back in Ann Arbor on Sunday and reality will set back in. I'm going to enjoy my last few days of freedom and relaxation. So, I will make some kind of light dinner tomorrow and we can hang at home and, you know, see what happens," she said with a hint of glee in her silken voice.

"Sounds like a plan." We picked ourselves up and meandered down the stairs and back to the car. I was acutely aware of more than one stare in our wake as we departed the restaurant. As Stella had said - "let them wonder."

We were back in her kitchen in nothing flat and Stella poured us each a San Pelligrino on ice. We'd had our share of alcohol for the night. It was so tempting being alone in her house after the conversation we had shared at the restaurant. I knew I should get to bed, but I lingered and we talked a little more.

"You sure you can't stay up for a bit?" she asked so innocently. "It's clothing optional at the pool after 10pm at night, you know. House rules."

"Mmmm, Stella. You are tempting me. But, honestly, if we got into things right now - as much as I want to - we'd be up all night. I just can't - this interview tomorrow is too important. But...tomorrow night? I'll be here for martinis on the verandah. And I won't plan on getting more than a few hours sleep."