BY: J.D. HARRISON
David Henderson had a wildly successful business career and retired before he turned 50. He now lives a life of simplicity and pleasure on New York City’s Upper East Side. David likes to focus upon—and honor—the women in their 50’s and up that he prefers. He is now facing complications from three women—a powerful business leader, a former colleague, and an heiress—with the challenging prospects of love, heartache, and danger. And he learns of the complications which link the three women to each other. Can he navigate the treacherous waters and continue his luxurious life? Will his comfortable existence change forever? David is forced to use his charm and his experience—both in and out of the bedroom—to forge his way forward.
I have a date tonight with a woman named Janet Saunders. We were introduced by a mutual friend, and all of our interaction so far has consisted of a few emails, back and forth, to confirm plans for tonight. I’m far too old to be a part of the Tinder generation, so I don’t arrange dates that will occur 20 minutes in the future. I’m 52. I’ve dabbled a little bit with Match, but other than that I’m not really into online dating.
The email exchange between Janet and me has occurred over the last week or so, for our Saturday night date. She suggested that we meet and have dinner at Patroon, on 46th Street, and I told her that it was a perfect choice. It’s a really nice place. Elegant. I’ve been there a bunch of times but not quite frequently enough to be called a regular.
It’s a leisurely July Saturday at home for me. I live on the Upper East Side (UES) of Manhattan, a block off of Central Park, in an apartment that I’ve owned for going on seven years. Other than my usual Saturday morning long run in the Park this morning, it’s a lazy day. I’m a pretty serious runner. I’m in the middle of my summer/early fall run-up to the November 26.2 mile stroll around the five boroughs known as the New York Marathon. This fall will make my 8th consecutive run. 15 miles this morning that were relatively smooth, so I guess I won’t keel over dead during the race. Other than the morning run, my day has involved nothing more than reading the Times, watching sports on TV, and a several block walk down to my local market to re-stock my fridge.
By late afternoon, I’m starting to think about the date a little bit. Janet and I have not met, so I’m starting to form a profile of her in my head, based on just a few emails, which is potentially dangerous. The only facts that she has shared so far is that she lives on the UES, has lived in the city for years, and works in the Financial Services industry. So that narrows it down to maybe only 10,000 people. And 10,000 profiles. My initial impression is that she’s very straightforward, no nonsense, and businesslike. Based on our exchanges so far, and the fact that she picked Patroon for dinner, which is mostly an old school place, I’m gonna guess that she’s late 40s or 50s. Like I said, this envisioning thing is dangerous. I could have it 100% wrong. But over the years I’ve learned that I’m getting pretty good at it.
Time to prepare for our date. I like having plenty of time to get ready and not having to rush—not that it really takes me that long, though. I’ve had women give me a hard time for my ability to get ready to go out in what is seemingly 5 minutes. I can’t do it in 5, but it’s not much more than that. A quick shave, just my neck, as I’ve had a beard and mustache for years. Neatly trimmed and going gray. Oh well. A shower, wash and condition of the hair, towel off, a splash of cologne, and ready to get dressed. I grab a gray suit, white shirt with blue stripes, and a tie that has a bunch of colors but the main effect is pink.
I am pretty anal about being on time for things. I know it’s not everyone’s thing, but sometimes I can’t understand why a lot of people suck at being on time, and suck at estimating how long something will take, as in “I’ll be there in ten minutes” and then they arrive in thirty. It’s not a long ride from my place down to the restaurant, and the ride goes relatively quick, so I’m early, which is my normal state of being. We’ve agreed to meet in the ground floor bar at Patroon. I grab a seat at the bar at around 7:15, for our 7:30 meet. The bartender thinks to himself “I think I recognize this guy” but he doesn’t take a chance trying to recall my name. He gives me a friendly greeting and a smile and serves up my usual cocktail, a Sapphire and Tonic. A tasty adult beverage. A lifelong friend of mine served me my first gin and tonic when I was 19 or 20, saying, “a good gin and tonic tastes just like a Sprite.” I don’t know if I would completely agree, but I guess it’s a fairly easy transition from a childhood of drinking a good number of sugary non-diet Cokes, Sprites, and Pepsis.
I’m facing the entry of the bar, so that I can watch for Janet. She has a picture of me, but I don’t have one of her. At 7:30 pm on the dot, a woman walks in and I’m pretty sure it’s her. My initial impression is that I’ve nailed the mental profile. She looks to be late 40s, fit, maybe 5’7”. She definitely looks like a business person. Very well put together. A trim figure. She’s wearing a very pretty gray dress, just slightly above the knee, heels, hosiery. No wedding ring and not much jewelry. She has dirty blonde hair, fairly short, looking perfect. She spies me at the bar and walks in my direction.
“David?” She offers. I’m already getting to my feet.
“Janet—great to see you!” Whenever I’m meeting a woman, especially for the first time, I always say “great to see you” rather than “great to meet you” so that anyone nearby doesn’t get the impression that I’m meeting this woman for the first time.
Standing in front of her, I place both of my hands gently on her hips and I kiss both her cheeks. This is pretty much the standard NYC greeting among adults of opposite gender (and sometimes the same gender).
“Wow—you’re a big guy!” I’m 6’4” and 200 pounds.
“Would you like to have a drink here, or go right to our table?” I ask her.
The seat next to me at the bar is open. “Let’s have a drink here,” she says.
We both sit. She doesn’t seem nervous at all, which is good. Maybe she’s approaching this like a business meeting. The bartender cruises over to take her order. “Grey Goose martini, dry, straight up, with olives and a twist.”
I smile at her and say, “A woman who knows exactly what she wants. I like it!!” And she gives me a half smile in return.
“Is Patroon a regular spot for you?” I ask.
“Yes—I’ve been coming here for years. It’s a favorite.”
“So, you must know Ken then.” Ken is the owner.
“Oh yes. Many drinks and a few dinners with Ken over the years.”
In reply I say, “I’ve been here a bunch of times, but I don’t quite have ‘regular’ status. It is a great place. The rooftop bar can be fun at times, but on a night like tonight, a Saturday night in July, there are too many smokers and too many young people for my taste. I’d much rather be down here with the civilized.”
“Completely agree. I can’t stand smoking.” Her martini is delivered, and she takes a sip.
“Me neither. My mother was a smoker for most of her life, and it created in me a genuine hate for smoking….and smokers.”
“Is your mother still around?” Janet looks directly into my eyes with some intensity.
“No, both of my parents have been gone for years. My dad died 30 years ago, and my mom 20. So, I’m pretty used to life without them. Given how and when they died, my sister and I never really had to deal with the whole elder care thing, which I know a number of my friends are dealing with now.”
“I’m sorry about your parents. And yes, I’m dealing with it. Not good. So, it sounds like you just have one sibling? A sister?”
“Yes. She lives out in the SF Bay area. She’s two years older than me.”
Janet takes another sip of her drink, and I sip on mine. There’s a bit of a lull in the conversation, but it doesn’t feel uncomfortable, at least not to me. This woman definitely seems to be comfortable in her own skin and I doubt that she feels the need to talk nonstop.
I look at her and smile. She puts her hand on my forearm. I love physical contact. And the invitation that she has offered. “Would you like to go ahead and grab our table?”
“Yes, let’s do that.” I looked at the bartender. “Can you send our drinks to our table, and put these on our dinner tab?”
“Of course, Sir.”
We then go up front to see the hostess and she leads us to our table. The arrangement is side-by-side seating, rather than across-from. That’s fucking awesome. My absolute favorite way to have dinner with a woman. Janet sits down and I slide in next to her. But not too close. I don’t want to get in her personal space. A moment later, our drinks are delivered. Along with menus and a wine list. The waiter gives us a short introductory spiel and then very smartly steps away.
We continue to sip our drinks and we each take a look at the menu. I figure she has it 100% memorized, and I’m about 50% with it. I mentally select a couple of options, then take a quick look at the wine list and do the same thing. The sommelier sees me holding the list and runs over to offer assistance. I send him away. I can pick my own wine, I’ve done this before. There’s only one sommelier in all of NYC with whom I have regular conversations when I’m in his restaurant.
“So, Janet, I’m sure you have this entire menu memorized—what are you thinking about for dinner?”
“I think I’m gonna go with the smaller rib eye.”
“A meat eater. I like it. I’m going for the beef tenderloin. We should have a bottle of wine. Do you prefer vanilla or strawberry?”
A puzzled look on her face. “What??”
“I’m sorry. It’s my stupid wine joke. White or Red? I’m assuming that you’d be up for a big red, but I could also do a white if that’s your preference.”
A wry smile. “Definitely a big red.”
There’s a Spottswoode Cab from a solid year that will do nicely. The waiter comes back and takes our orders for food and wine.
As the waiter walks away, after a moment I realize I’m staring at Janet and I catch myself. “You look really great. I love your outfit.” I mean it. I love this woman’s look and how well put together she is.
Janet smiles and says thanks. She gives me the intense look again, but at the same time puts her hand back on my arm. “Forgive me if this sounds strange, but can I ask you some questions? I need to know more about you.”
“Ask away. Ask me anything. I’m Mr. Full Disclosure.”
“OK, here goes. If you don’t want to answer any of these questions, just say so.”
In that moment, I can’t think of any question that she might ask me, that I wouldn’t be willing to answer.
“Where are you from? I don’t think you’re an NYC native.”
“I’m not. I grew up in the Chicago area. I’ve been in NYC for about 10 years.”
“Chicago proper, or Chicago area?”
“Area. Suburbia. Outside the city. My mom the smoker was pretty much June Cleaver.”
“What brought you to New York?”
“Work, originally. I used to work in a big consulting firm and I ran a project here for about 3 years, while I was living in Chicago. After a while I got tired of the corporate apartment, realized I really liked the city, and just moved here. I’ve had several different apartments, all on the UES. I’ve been in my current place for about 7 years.”
“You used to work in a big consulting firm—but no longer?” Her hand is still resting on my arm.
“No longer. I did really well there. Was able to make partner fairly quickly, and I was pretty lucky on the timing. After I had been a partner for about 5 years, the firm went public and we all got rich. I was only there for about another two years and then I just retired. It was my last real job. Now I just manage my investments and enjoy the city.”
“Where did you go to school?”
“Northwestern. I was a big math and science guy growing up, so going to a ‘local’ school and majoring in engineering seemed to be the logical thing to do. I got a degree in chemical engineering and then stuck around two more years to get an MBA, then I joined that big consulting firm. I never did work as an engineer, except for a couple of summer jobs while I was in school.”
“Have you ever been married?”
“Yes, for 8 years, many years ago. No kids. She and I got along fine, but the passion and genuine interest in each other kinda faded away after a few years.”
“Sorry. Are you into sports? What sports do you do?
“Well—spectator-wise, I’m a pretty big sports fan. I guess the sports I watch the most of on TV are NFL, some college football, some basketball, and a lot of golf. Participant wise, I play golf and I’m a runner.”
“Where do you play?” This is a loaded question, among New Yorkers. The answers can range from anywhere between the Van Cortlandt muni in the Bronx, all the way to Winged Foot and Shinnecock.
“Sadly, I haven’t ever gotten a club membership here, although I had a very nice one in Chicago. The truth is that I don’t play anywhere near as much as I’d like to. Playing golf as an NYC resident is pretty much a full day proposition. I’ll hit some of the nicer public tracks in the area, and I do have a few friends who have club memberships who are nice enough to host me from time to time. Curious—do you play?”
“Yes. I have a membership at Liberty National.” A relatively new club, by Metro New York standards, in Jersey City, NJ, with a front row view of the Statue of Liberty. Has hosted a couple of PGA events.
I give her a big smile and I reach out to touch her shoulder. “Janet, you and I are going to get along just fine.” She smiles back.
“OK David—I think that’s enough of my third degree for now. You’re right—you seem to be willing to answer any question. I really appreciate how open you’re being.”
“No problem. Nothing to hide and willing to share. Would you mind if I asked you a couple things? Nothing too personal.”
“When we were trading emails last week, you said you worked in Financial Services. Care to elaborate any on that?”
“I’m an SVP in the Corporate Strategy function in one of the stupidly large banks in the city. I’ve been there for 20 years, through lots of changes and a fair amount of adventure. I started out as a staff accountant, and then worked my way up through the Finance and Accounting organization. The current job in Strategy is a nice change from what I did before. Interesting work.”
“So, you’re with one of the stupidly large commercial banks, not one of the investment banks.”
She looks a bit startled, for a second. “Yes. How did you figure that out?”
“You said SVP, not Partner. 25 years in management consulting, you learn a couple things.” I smiled at her.
“Where on the upper east side do you live?”
“In the 80’s, between Madison and Park.”
“Nice. I’m about 15 blocks down from you.”
The waiter showed up with our entrees and the bottle of Spottswoode. I tasted it, it was great but needed some time to open up. I asked the waiter to decant it, which he was happy to do. I’m not big on all of the ceremony around the tasting of a bottle of wine in a restaurant. Open it, I’ll taste it, let’s get to enjoying it.
We started in on the food and the grape and continued to chat. Great, interesting conversation. This was a woman of substance, smart, with a sense of humor. And I think a sense of fun, buried in there somewhere. We touched each other casually as we chatted. Gotta love the touch.
We were winding down on the food and the decanter of Cab was sadly empty. The waiter asked if we wanted dessert. We looked at each other and both decided no. She suggested that we have one more glass of wine. An awesome idea.
“David—this has been an extremely enjoyable dinner. You’ve completely exceeded my expectations.”
I wonder what her expectations were. Oh well. “Thanks. I’ve had a great time. And let me say again—you look absolutely great. Love your look.”
She appreciates the compliment, but I’m wondering if some part of her won’t let her take it in fully. Does she understand how attractive she is? I’m not sure. I doubt that the other senior execs at the bank shower her with compliments about her looks. Maybe I’m wrong.
“Thank you, David.”
As we finish our extra glasses of wine, the waiter brings our check, and a platinum Amex card is placed on the folio. She touches me again, on the shoulder, and then slides her hand towards the back of my neck. A much more intimate touch. She looks at me with that intensity, but also something that feels welcoming to me.
“Let’s go back to my place.” She says quietly but intently.
“That sounds like a great idea, Janet.” I reply as I stare back at her.
We call for an Uber. The New NYC Taxi. It seems like 90% of the Ubers I ride in are Chevy Suburbans, but we luck out and this one is a very nice Mercedes sedan. We climb into the back seat and I’m very focused on the woman that is with me. As she sits there, her dress rides up a little bit and I see more of her very nice legs, which have been hidden under the table for the last two hours. I put my hand gently on her thigh, covered in very sheer nylon, and I lean over and kiss her. Directly on the lips, softly. She kisses me back. The rest of the ride back to her place passes in an instant.
We enter Janet’s apartment, and I can tell instantly that it’s an impressive place. Just standing in the entryway, my impression of her place is that it’s big, elegant, and impeccably decorated.
“Wow—I love your place!” Trying to not sound like it’s my first time in a luxury NYC apartment.
“Thank you. Its home. Could I interest you in another glass of wine? I have a Pinot in the kitchen that is begging to be opened.”
“Sounds perfect.” She leads me to her kitchen and hands me the bottle and a corkscrew.
“Love the kitchen. This looks serious. You must be a chef. You don’t eat out 98% of the time like most of us.”
“Yes, guilty as charged. I love to cook when I get the time.”
I get the wine opened and she leads me into her living room—another large and very impressive space—and we both sit on her couch. Close but not on top of each other.
“How long have you had this apartment?”
“Going on ten years. Best investment of my life. It’s my home.”
We do a quick toast with the Pinot. A quick taste. I look at her. “Very nice.”
“Are you talking about me, or the wine?” She says with a smile.
“Yes,” is my answer. She’s sitting next to me and OMG those legs are outstanding. I’m also now able to check out her high heels. Very stylish. The heels are on the high side. I’m not sure this is a pair that she wears to work.
She sees me checking out her legs and shoes. I’m totally okay with her seeing it.
My eyes go from her awesome legs back to her eyes. “I’m gonna take a guess—are those Manolos?”
“Fuck me!! How do you know that?” She gives me a devilish grin. I think the wine is kicking in a little bit. “Are you a cross dresser? No man knows that stuff.”
“Let me just say that I’ve been fortunate to spend a lot of time over the years with beautiful women who have money and often times good taste. I’m a lucky guy. Sometimes the topic of shoes will come up. And I pay attention. The easy ones to pick out are the Louboutins, with the red soles. But the Manolos are awesome too. Yours are beautiful. And you wear them well.”
“David, I think you and I are going to get along just fine,” she says with a warm smile. She grabs me by the tie and pulls me in. Kiss. This time it’s getting more intense. I open up my mouth and ease my tongue into hers. She welcomes it and returns the favor. We make out on her couch for a little while. My hands are all over her and I’m pretty sure that she’s enjoying it.
We pause. “You are a most excellent kisser, Mister,” she says and then she locks her mouth onto mine again.
She looks at me again. Miss Intensity on full bore. “Let me show you my bedroom.”
She stands, takes my hand, and walks me into her bedroom. She switches on a light. Soft, not bright. Perfect. Still with my hand in hers, standing by the edge of her bed, she turns away from me and says, “Help me out of my dress.”
From behind her, I unzip her dress, slide it to the floor, and help her step out of it. I unhook her bra and slip it off of her shoulders. She’s now standing in front of me—facing away from me—in her pantyhose and Manolos. Oh fuck. I get closer to her and press myself against her ass. She has brought me to full attention and I’m letting her feel it. I wrap my arms around her and kiss her on the back of her neck and her head. She presses herself back against me. I peer down the front of her, over her shoulder, and take in my first view of her breasts. Perfectly shaped. Not especially large. Her nipples are huge and are clearly very hard. I stroke her lovely boobs, and my hands explore everywhere—from her throat down to her thighs. I’m enjoying it. She’s enjoying it.
I gently guide her to sit on the edge of her bed. I slip off the Manolos and slide down her pantyhose. Oh My God, this is a beautiful woman.
“I need to get naked, too. You wanna help me, or am I on my own?”
“You’re on your own.”
I loosen and undo my tie, unbutton and take off my shirt. Undo my belt and my suit pants. Giving her a bit of a show, I know. I’ve already enjoyed her show. I reach down and pull off my shoes and socks. Hard to look sexy doing that. I slide my pants down and step out of them, so now I’m standing there in nothing but my boxer briefs. I pause for a moment, and just let her look at the package. She has me 100% at attention. I pull down my boxer briefs and step out of them.
“Oh My God—you are HUGE!” She gasps.
“Guilty as charged,” I say with a smile. I climb onto the bed and Janet scoots up next to me. She’s on her back and I’m on my side. We resume the making out that we were doing on the couch, and again my hands are all over her—enjoying the feel of her nipples, her tummy, her thighs, and her bush. I am thoroughly enjoying this woman.
“Would you like me to go down?” I whisper to her.
“Oh my God, yes!”
I position myself between her legs. Her pussy is absolutely gorgeous. I could get used to this. I tease and explore her with my fingers, lips, and tongue. I concentrate on taking my time, taking it slow, enjoying her amazing pussy and letting her intensity build. Teasing her clit with my fingers and my tongue. She’s starting to move and make little noises and puts her hand on my head and in my hair. I continue on my slow build. I know how to do this.
I need to fuck her now and I’m pretty sure that she needs it too. I put on a condom. When I’m with someone for the first time, I’m very conscious of how large my cock is. We need to take things slow. I get on my back. “Babe—get on top of me and lower yourself down onto him. Take it as slowly as you want.”
“Oh My God,” is all she can say. She does what I have suggested. She gets on top of me, takes him in her hand and guides him slowly—and carefully—inside her. She’s plenty wet, so he slides in easily. She takes it very slowly, but eventually he’s completely inside her and we’re moving together. My hands are holding her ass. She alternates between sitting up on me and laying down on me, so that she can kiss me while we fuck. I love being inside her and I love this woman’s body. As before, I’m concentrating on proceeding slowly and letting the intensity build as slowly as possible. She’s having a harder time maintaining her focus. Which is awesome. She is loving how I’m fucking her.
She looks at me. “I want you on top of me.” I’m able to roll her over while still inside of her and we continue. The rhythm of our fucking is perfect. She’s going crazy. I reach down, pull my cock out of her and rub him all over her pussy lips, teasing her. I think she’s going to scream. I stuff him back inside her. I can fuck and contain myself for a long time. I just keep on giving her my cock, kissing her, and feeling her move underneath me. On and on.
I can feel her approaching her orgasm. I keep the same rhythm and lock in on her face as she comes. It’s a wonderful mixture of pleasure, excitement, abandon, and I think a little bit of surprise. While she’s still going, I let myself go, and I come big, with my cock deep inside her. I pull myself out of her lovely body, collapse on her bed, on my back, and pull her over so that her head and the top half of her body are resting on my chest. We both just enjoy the other as our breathing returns to normal.
“You are so completely yummy,” she whispers to me.
“You are pretty fucking yummy yourself. And completely gorgeous,” is my reply.
We relax a while longer.
“That’s the biggest and best orgasm I’ve had in a long time. Thank you.”
“I’m glad. And you’re quite welcome.”
More time passes. She doesn’t say a word and her breathing is very steady. I’m wondering if she has fallen asleep. Just when I think she’s out, she says to me, “I think you should go. I need to get some sleep.”
“I can do that,” I say. I ease her off of my chest, look directly into her eyes and give her a soft kiss. “Thank you for an incredible evening.”
“David—there’s something for you on my dresser,” she says as I’m collecting my clothes and putting them back on.
“Thank you, Janet. Have a good sleep.”
I grab the envelope and the rest of my clothes and show myself out. I decide to call for an Uber, even though my place is only a 10-minute walk. The Uber guy shows up—of course it’s a Suburban this time, and I climb into the back seat. I look into the envelope and it contains $2000 in cash. A big stack of Benjamins.
In the immortal words of Tone Loc—I get paid to do the Wild Thing.
@2020 by J.D. Harrison