John, 62, New York, Sugar baby

I read Johns email in detail.

"Dear Jenny,

I am beyond thrilled that you have decided to respond to my inquiry earlier this year. Your interest in engaging in a relationship with me has sparked my curiosity. I am a well off man that desires an attractive young lady to join me when attending events and gatherings. I also admire your youth and beauty, attributes which lure me to you even more. Below is my picture. I see you are in NYC as am I. Let me take you out for dinner so I could learn more about you.

Love,

John"

I conducted a reverse image search on the pic he sent and quickly found his last name. using his name, location and age, I was able to pull up a lot of info about him. Johnathan Theodore Jeffries is recently divorced from his second marriage, 2 adult kids, an published author, art director and philanthropist. His net worth is over 6 million dollars and he has 3 homes in the US. This could be the man who saves my parents house. His children, both boys 30 and 33 years old, live out of state. His first wife Jillian was born in 1970 and married to John from 1981-1988) passed away in 1988 from cancer. His second wife, Ye-Jin, was born 1973 and married to Mr. Jeffries from 2010 - 2024. Little information about the divorce is available. His social media is limited, but older pics on Facebook show that his ex-wife Ye-Jin came from a wealthy Korean family. While I hate to judge other females, especially other females of Asian decent, it is beyond clear that despite her plastic surgery efforts, she is not attractive. The common denominator among his past is that both marriages appear age appropriate.

I think for a moment, I could be his granddaughter. Is this creepy or sexy? I stop thinking and respond to John's email.

"Hey John,

You and dinner sound amazing and yes, I'm in the city as well. I know it's short notice, but I'm free tomorrow evening. Would that work for you?"

I click send and within a minute, receive a response.

"Hello lovely Jenny,

Yes, I am free tomorrow. I got a reservation at the The Whilmore-Freidman Country Club in Midtown for 6:30pm. Wear a dress, it's fine dining.

Love,

John"

I thumbs up his massage in agreement.

Next day / Day of the Date:

I wake up nervous and quickly look through my closet. I only own one dress and it is super short and clingy. I bought it a while ago and never had the guts to wear it as I would feel extremely self-conscious. It is white and tight, leaving little to the imagination. If this is a fancy restaurant, I might look too slutty. I try it on and pose in the mirror, debating if I can wear it or not. I do look very sexy, but maybe too sexy. I can't wear a bra because the straps will show. I fix my top so that my tits are properly secured by my dress, then pull my dress down to remove the wrinkles and straighten my outfit. My figure is very tightly wrapped, exposing every curve of my body. My modest breasts look amazing and the bottom of my dress hugs my tight butt perfectly. The dress is so tight that it is almost see-through. Noticing this, I change my panties from traditional to a thong.

I think about it long and hard about this outfit. What if I get cold and my nipples pop through? What if my dress rides up and my bottom is exposed? What if I get side-eye from everyone for underdressing?

I don't have another dress nor do I have money to spend on a new one. This will have to do. Besides, the more eye candy I give him, the more likely I am to be able to help save my parents home. I must keep my eye on the goal.

I put my black heels on, enter my uber and head to the restaurant. While sitting in the back seat, I apply my makeup fix my bra and spray 2 squirts of perfume on my breasts and one between my legs. I glance up to see the Uber driver smirking. My mind immediately thinks "pervert!" but then I remember I'm going to meet an old man that DM'ed me from a sex story site to meet me. I decide to ignore his gestural response, finish tidying myself up and move on.

The Clubhouse:

I arrive at 6:20 and am stopped by a doorman. He asks my name and I reply "Jenny". The doorman moves to the side, gestures for me to enter and says, right this way, Mr. Jefferies is expecting you. As I pass a long, fancy hallway, I glimpse my reflection in the curved glass wall. I look hot as hell.

I enter the restaurant the restaurant and recognize John immediately. He looks exactly like his picture. He's Caucasian man about 6'2" tall and maybe 190 lbs. He has full facial hair including a mustache and beard. He's wearing a pair of well-fit black pants and a Brooks Brothers shirt. I notice a Rolex on his left wrist and no ring.

The doorman gestures towards John, indicating that I should approach him, and leave. As I approach the bar, John notices me and present a huge, warm smile and begins, "Welcome Jenny. It is a pleasure to meet you." He reaches in for a hug, which I accept. I feel him pressing very hard against me, embracing me more than I expected for an introductory hug.

His chest is pressed firmly against my breasts. He he pulls away, I notice his smile has grown. He is not so subtly undressing me with his eyes as he performs a full visual scan of my body. I sit down at the bar stool next to him, lock eyes with John and smile. His eyes are darting back and forth between my eyes and the hem of my dress, exposing almost my entire thigh. I should be creeped out, but it is surprisingly making my extremely excited. As I cross my legs, I notice his eyes disconnect entirely from mine and stare at my hips, hoping to get a glimpse of my thong.

He reconnects his eyes to mine and says, "You are as lovely as I imagined. Our table is ready." John, being a gentleman, offers a hand to help me off the bar stool. As we follow the waiter to our table, he places his arm around my lower waist. As we arrive to our table, he pulls out my chair and assist me to my chair, and pushes is in after I sit. I've never been treated with such class in my life! He then sits across from me. He takes the cloth napkin and places it below the tablecloth on his lap. I do the same.

The waiter asks, "Can I offer the lady and yourself a drink while you decide on your meal?"

John looks to me and says. "May we enjoy a cocktail while we enjoy our presence?"

I smile. Not only does he sound fancier then I am used too, he is flattering. I nod my head once while replying, "Yes please".

John arrogantly waves down the closest waiter and says, "A Manhattan for the lady Double shot of blue label on the rocks for me."

The waiter nods and leaves. As the waiter leaves, John looks my straight in the eyes and says, "you are an angel sent down from heaven. Quite possibly the most stunning women I have ever met."

I can't help but blush. I lower my eyes and reply, "Thank you. You are quite a hansom gentleman yourself."

John smiles as he reaches to hold my hand. He continues, "Your glow is magnificent." He starts massaging my hand as he continues, "You are smart, stunning and exotic, a dream women to join any man. I am thrilled to have you sitting across from me."

As he finishes his sentence, our drinks arrive. He orders food for the both of. When the waiter leaves, John raises his class and says, "cheers". I follow his lead, click glasses with him, and have a sip of my drink.

As I swallow my first sip, I feel something brushing against my ankle. A second later, I feel it begin to rise up my calf. I look at Johns eyes to see a lustful look. At that moment I realize he is rising his foot up my leg. His foot, shoes and socks off. He reaches my knee and continue to inch towards the hem of my dress. His smile turned into a smirk as he licks his lips. It's at that moment that I my initial guess was correct. John wants to fuck me.

I begin to feel a nervous chill as I again ask myself a million questions. Should I stop him? What if someone sees? This place is too fancy?

Should I...

1) Let him continue

2) Gently push his foot away

3) Remove his foot and make it clear his actions are not acceptable

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