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Jenny Ch. 03 – The Whiskey Sours

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The arrow on my computer screen is over Add Friend and my index finger is poised to hit RETURN as I ponder whether to ask Dr. Jennifer Friedman to be my Facebook friend.

Jenny, as she likes to be called, and I became acquainted while we were both college students, long before I became a billionaire. I had a crush on the pretty girl who lived next to me in the dormitory when we were freshmen more than a decade ago but the same was not true for her. Nevertheless, we became close friends. I treasured our non-dates to movies and the countless meals we shared during our four years as undergraduates. She was scrupulous to always pay her own way, lest I think that our friendship was something more.

She still has the same last name as in high school. But female physicians often keep the name with which they are born upon entering their profession regardless of their marital status. Her Facebook page says nothing about her relationship status. And the photos she has posted of the places she has vacationed are bereft of children or the good looking men I’m sure swarm about her, wanting her to be their partner or hoping at least for a fuck. Maybe she’s between relationships. So I might still have a chance.

Jenny is the woman to whose image I masturbate. But considering myself out of her league even after becoming wealthy, I had never Googled her, looked her up on social media, or even tried to locate her office or home telephone number to call and talk to her until now. I just jack off to her image in my mind.

As I think consider pressing the return button to send the friend request, I ponder the consequences of my actions. What if she’s married and hasn’t posted any pictures of her kids because she doesn’t want them to be scrutinized by internet trolls who may disapprove of how much body fat they do or don’t have? Would I then find it disgusting to get sexual gratification by masturbating to the image of a woman in my mind’s eye doing some of the tawdry and lewd things shown on TV whose little kids look upon her as a paragon of virtue who could never possibly engage in anything tawdry or lewd? What if she is a just a private person who doesn’t want to be bothered? Or what if she remembers me as an insecure nerd lacking social skills who was just comic relief for her back in the day?

I don’t get any action in the bedroom or anywhere else for that matter. Wary of golddiggers, I won’t get in a relationship unless I sense a connection to the person. As far as escorts go, what if I impregnated one? I couldn’t bear the thought of a life I spawned ending in an abortion or worrying that my child will be raised by a sex worker and follow in her footsteps.

I’m a nerd who feels most comfortable talking about the weirdness of quantum mechanics and alternate universes. My sense of humor is dry. Jenny always liked that, but alas, she didn’t like me the other way.

My competition for intimate partners are other tech billionaires who talk better than me, know how to dress, don’t have bad breath, and do exciting things in their spare time. The few women with whom I’ve felt a connection have always been in relationships with such men. And no matter how awfully their men treat them, they endure it or get into another relationship that is just as bad.

After graduation Jenny and I parted company; she to go to medical school and me to graduate school. Becoming wealthy was not something for which I had ever strived. I had embarked on a path to become a researcher but things didn’t work out in my favor.

The salaries of the postdoctoral fellowship positions I was offered weren’t enough to allow me to both eat and pay off my student loans. The best I could do was land a part time job as an instructor at a junior college. Instead of doing research that would lead to a Nobel Prize, I spent my life trying to find a full time job and form a relationship with an average looking partner with whom to start a family. Instead, I had no luck finding a job any better than the one I had. And the below average looking women that I ended up dating didn’t return my calls after going out with me three of four times.

Such was life until a student hooked me up with a friend who needed someone computer savvy to help with programming for the new social networking site he was setting up. He was pleased with the way the software ran, sought me out as a mentor, and trusted the advice I gave him. He generously compensated me with stock options that caused me to end up becoming a billionaire with a seat on the board of directors when the company went public.

My passion for Jenny has not ebbed. Full of myself and now used to getting my way, I had finally gotten up enough confidence to make my fantasy girl my real girl. Surely she will look upon me differently now that I’ve made something of myself. What woman wouldn’t want to be in a relationship with a billionaire?

But then the nagging doubts Antep Bayan Escort that have always plagued me take back over. Jenny, always a good judge of character, will certainly see my newfound swagger as phony and, if we reconnect at all, most likely continue to think about me the way she always has, just as a good friend.

But maybe just having her as a friend will be something worthwhile. Though loath to learn I might have just been comic relief for her back in the day, I press the return key and send the friend request.

My heart pounds. That I may actually communicate with Jenny after all these years terrifies me.

Though shy around women, I was never shy around Jenny. But things are different now. She was never in my masturbatory fantasies during the time we were actually together. It was only during the lonely waits in the laboratory for experiments to finish when I was a graduate student that her image replaced those of actresses, supermodels, and imaginary females of my own creation in my erotic thoughts.

My one relief is knowing I will probably not speak to her tonight. People don’t seem to call out of the blue anymore in the age of social media. So maybe messaging back and forth will be something I can handle. At least she won’t have to listen to me stammer as I often do.

The minutes pass. When will she look at Facebook and see my friend request-in minutes, hours, days, weeks, months, or years?

I wonder if she’s Googled me. It occurs to me that if she has, when she sees my friend request she’ll probably think I just want to get laid, which is true.

But if that’s the case, what if she’s gone bankrupt and needs money, which I have? Wouldn’t that be great? That could get me laid!

But then, horrified by what the most primal parts of my brain have cooked up, I empty my mind of such deprecating thoughts regarding the woman about whom I fantasize.

The five minutes it takes Jenny to accept my friend request seem like eternity. Then the Messenger window opens. My finger trembles as it hovers over the RETURN key while I ponder whether to open the message and see what she has to say.

My finger stabs the key and Jenny’s message appears.

“Hi Rick! What are you up to?”

To say I’ve become a billionaire and sit on the board of directors of one of the world’s hottest social media companies would be true, but what if she decides I’m bragging so she’ll let me fuck her?

So what can we talk about? The interests we share would be a good start but my infatuation with her is the only thing we have in common right now, an interest that she never shared. What can you say to your fantasy girl when it turns out she is more than an image in your mind when you pleasure herself? Tell her that the way she appears in your mind’s eye gives you, a mediocre teacher who until recently was made fun of by his students and disdained by unattractive women, great orgasms?

But now she is a busy obstetrician who I’m sure can afford just about anything she wants. So my riches won’t dazzle her. But the seven words she typed indicates that she may want to rekindle our friendship.

My response: “I miss you.”

“I do too,” she types.

After that comes bringing each other up to date. I tell her about helping the friend of a student with software for his social media company and being compensated with stock options that have made me as rich as Croesus when the firm went public. She did not know about my windfall and is happy for me. I tell her that she will deliver any babies I might have should it become possible for men to become pregnant. She thinks I am as funny as I always was and informs me she is still single, after which she laments the scarcity of eligible men her age. I let on that I’m lonely and feel uncomfortable with my wealthy compatriots. She tells me about being the low person on the totem pole in her obstetrics practice and how she now spends her vacations resting instead of traveling.

She would like to see me but has no time off for three months.

“Why don’t you come down here and visit? I have an extra bedroom in my house,” she types.

It goes without saying that my heart jumps with joy. But did she have to add the extra bedroom part?


But I take her up on her offer. The first visit goes well. She shows no signs of wanting our relationship to be any different than it ever was. But we continue to see each other.

Her friends find it odd that a young tech entrepreneur flies on his private jet every weekend into the midsize city where Jenny practices obstetrics. God knows, with all his money, women must be lining up to fuck him in Silicon Valley or from wherever he comes, so why go after an old flame who goes out on dates with other men between his visits?

But Jenny sees nothing strange about connecting with an old friend in such a manner. Nor does she find it incongruous to dine casually at the local franchise of a chain that her plutocrat friend might own when she could have hopped into his jet and flown with him to a five star restaurant almost anywhere in the Western Hemisphere.

It’s lucky for me that Jenny is as unlucky in love as I am. She tells me all the men she’s dated are either already married to their work or hope to live off the stream of cash that her job generates. Thirty-two years old, she frets that intimacy with someone she loves and motherhood are going to pass her by.

After a couple of months of weekend visits, I notice Jenny’s attitude toward me change. When she finally is allowed a few days off, I join her in Orlando for a medical convention. In our time together after the daily sessions, I see Jenny look wistfully at couples accompanied by their small children strolling through the theme parks. On the next to the last day, she grabs my hand and my heart races as I enjoy two hours of newfound intimacy while we promenade around Disney World. I hope for an invitation to her bedroom in our suite that night, but after killing a bottle of Cabernet Sauvignon together during my first taste of real French cuisine, we retire to our own beds.

The next weekend that we are together, I notice she is wearing more makeup, not that her flawless complexion ever requires any more adornment. Her outfits are no longer modest blouses and sweaters with well fitting but not tight pants. Instead, she presents herself to me clad in sheer tops with plunging necklines and yoga pants or skinny jeans. The days of hiding her curves are gone.

Our conversations over Skype become peppered with sexual innuendos, but her implications always are that I must be having a great time with the kind of women who thinks that hooking up with me would result in them never having to want for anything. Does she want to be that woman or is that the woman she doesn’t want to be?

It’s not long until the holiday season begins. Although Jewish and a member of a local synagogue, Jenny enjoys the festive atmosphere and the parties during which alcohol flows freely, making the stuffed shirts with whom she works let their guard down.

My flight is delayed and I arrive at Jenny’s house only an hour before her medical staff Christmas party. I pull the black Mercedes I have stashed at the airport into the carport next to her kitchen, and she answers the door wearing the kind of little black cocktail dress in which countless women have attired themselves to send a signal to a man.

The dress barely covers her ass and I like the look of her in it. But is the change I’ve seen in her lately just my imagination? Or is Jenny looking hot tonight for the good looking guy with whom she’s in love, the handsome guy who’ll meet her at the party, who doesn’t stutter like me and can make small talk?

On the countertop next to the stove stands a nearly empty bottle of Chardonnay. The rim of the single wine goblet next to it is stained with her dark red lipstick. At the bottom of the glass is not even a sip of the clear yellow fluid.

Her stride is unusually deliberate as she escorts me to the sofa. It’s as if she isn’t used to walking in the black stiletto heels she has chosen to wear tonight. But she has never seemed to lack confidence in heels before.

So why is she drunk? I’ve never known Jenny to drink alone. I doubt she is a closet alcoholic, for I’ve never even seen alcohol in her house before.

She looks down on me when I sit down. Her countenance is radiant. The foundation that she has chosen blends perfectly into her olive skin and hides every little blemish. Just the right amount of blush gives life to her cheeks. Black eyeliner and light blue shadow adorn her eyes, which plead the case she is making for wanting to be fucked tonight. Around her neck is a gold chain from which dangles a blue sapphire pendant surrounded by diamonds. Gold bangles adorn her wrists. A string of diamonds hangs from each of her earlobes. Gold bands embedded with rubies and diamonds adorn her fingers.

All the clues suggest that she is after someone. Many people who succeed in the tech industry are socially maladroit and may even be on the autism spectrum. I count myself among them, so that all of this is for me only one of a number of possibilities my mind entertains. Or maybe thinking up all those other possibilities is just the way my mind is preparing me for rejection.

“You look great,” I tell her.

“Thank you,” she replies, slowly and deliberately, as if she is addressing someone who can’t hear or doesn’t understand English well.

I inspect her jewelry, jealous that another suitor might have given it to her. But there are no promises between us and she has been careful with her affections. I have no right to an exclusive relationship.

She smiles as I ogle her, seemingly embarrassed to be seen decked out in this manner.

“Buying jewelry has become my hobby,” she explains.

“It’s beautiful.”

“The jeweler used to work for TIffany’s. It’s really fun to go online with him and see all the newest pieces. But don’t worry, he’s gay.”

I raised my eyebrows.

“Not that there’s anything wrong with that,” she hastily interjects, qualifying her last statement.

“Not that there’s anything wrong with that,” I agree. I keep myself from saying, ‘But you won’t fuck a nerd like me. Am I that awful? Why haven’t we fucked just once?’

“You can drive us to the country club in the Jaguar, OK?” she blurts out anxiously, evidently not wanting to be arrested for drunk driving.

Why has she gotten drunk before the party? Because tonight someone is going to be lucky, I reason. But is it going to be me? And how will I feel if it isn’t?

She sits down next to me on the sofa with her hands folded in her lap. Her eyes flit to the clock and then to me, and she says nothing. Then I watch her look around the room-first to the mantle above the fireplace on which are displayed pictures of her parents, then to the shelves lined with the nineteenth century novels in which she immerses herself, and finally to all the photographs from her travels around the world adorning the walls. My eyes settle on a picture a woman took of Jenny and I in Orlando holding hands.

Jenny sighs and glances at the clock again. Disappointment registers on her face with the realization that less than a minute has passed. She inspects the rings on her fingers, then starts tapping her right foot on the floor and, thinking better of it, quickly stops.

Is this the time I’m supposed to make a “move”? What kind of “move” should it be?

My more socially adroit wealthy cohorts would know exactly what to do, but I’m torn between wanting to finally express my love and holding back to avoid ruining the evening if Jenny still does not want an intimate relationship.

I think about kissing her and decide not to, lest I ruin her carefully applied face. So I place my arm over back of the sofa, hoping that she will lean back and sink into an embrace, but she just sits next to me not moving a muscle, not saying a word, her gaze fixed forward.

I begin feeling uncomfortable, wondering if she is getting up the nerve to tell me something that I don’t want to hear.

“I know it’s early, but let’s just go now,” she insists, breaking the silence.

Her right leg nearly gives way when she arises from the sofa and her blank expression changes to a fake smile as she tries to hide her inebriation. We get our coats and she takes my hand as we walk into the garage. I open the passenger door of the Jaguar and she nods in appreciation as she slides inside. What I can see beneath the plunging neckline of her dress makes my member harden.

The engine of the Jaguar roars to life as the garage door opens. I put my hand on the shifter between the two front seats and then feel Jenny’s hand atop mine. I turn to her and hear her say, “I’m glad you found me on Facebook.”

I move the shifter back to put the car in reverse, my hand still in Jenny’s clasp. She reluctantly lets it go when I have move it to the steering wheel, patting it gently as if to say thanks for being there for her. I then glimpse her patting the corner of her left eye with a tissue as if to wipe away a tear, then lean forward to inspect her face in the mirror on the visor, and finally sit back, satisfied that she had not spoiled her appearance.

We talk about my flight, what time I had awakened in the morning, and exchange other pleasantries on the short drive to the hospital where the party is to take place.

That our relationship is about to end preys on my mind. It must take a lot of nerve to turn down unlimited riches, hence her discomfiture.

But why should she turn me away when we’re always so happy together?

What else could it be besides my fetish?

Aroused by the sight of a woman bound hand and feet, I fantasize of rescuing damsels in distress rather than being the cause of their pain.

It is nothing that I have ever shared with anyone.

But what else about me could be so terrible that would drive Jenny, my soulmate, away?

She delights at my nerdiness.

She has fun helping me pick out the clothes I wear, keeping me from looking foppish when I need to be in control.

And I have never demanded anything from her or even raised my voice in anger.

So she must sense a darkness about me, something frightening, something that cannot be spoken of, something from which she must flee before it’s too late.

What betrayed me? Could she have penetrated the layers of security and seen the images on my computer of women rendered helpless with their wrists and ankles bound as they wait to be hanged? Or could she have learned of my interest in shibari through my online presence?

Is the woman sitting next to me afraid that I might slice her to pieces while in the throes of lust? After I get my goodbye, fearing that I will use my wealth to stalk her, will she assume another identity and be completely lost to me?

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