Thursday 18th April 2019,
Jack Gary

Daddy’s Girl – Flirting With A Rich Girl

The old adage that money doesn’t grow on trees is certainly true. And the same saying goes for rich girls. In today’s fast pace, connected, information highway world, it’s hard to tell where anyone makes their fortune or how much of a fortune they actually have.  As part of what I do for a living, I’ve experienced enough business class travelling, sponsored VIP events, investor brunches, company owned charter planes, camel polo matches to know that life as you know it starts to seem like one giant, blacked out blur of shiny diamonds, platinum and privilege. This kind of life just comes with the territory, but if you’re not careful your moral compass can tend to get a little bashed on the 10-carat rocks along the way. You couldn’t sell my moral compass to the cheapest pawnshop in worst part of town. But the best part about being around the lifestyles of the rich and famous – if you can get through the thick layer of caviar and premium champagne – are all the ripe, nubile, of-age daughters with a family dowry that would make any unfortunate Russian orphan die of shock from envy. These girls don’t have to work a day in their lives so they fill their existence with shopping (all on daddy’s Amex) and sucking dick.

I met Anna when she was only 19 years old at a company sponsored polo event while away on business. The polo event didn’t have any polo or horses or mallets for that matter – just a white tent on a polo field on a hot, beautiful summer’s day.  Anna’s father owned the company. He got his fortune in kitchenware and they were hosting some kind of event for investors and company execs. This is the kind of company where top-level executive receive multi million dollar bonuses just because. So the event was all linen suits and extravagant polo attire. It was a real nouveau riche peacock show and I loved every second of it.  I was there just sort of checking out the scene, reveling and taking full advantage of the bounty of libations and free cocktail shrimp.  There is a distinct difference between regular rich and blasphemous rich. Anna’s family was the latter. Sure, money doesn’t grow on trees, but that is until you build something – most of the time a company like Anna’s father’s company – where you might as well have an entire orchard of money trees with lowly minions that scoop up the cash and bring it to you on a golden platter while you sit naked in a bath covered with more cash.

Yes, my moral compass and my sense of self might be a little off, but you never think about what a life like that would be like until you meet a girl like Anna. Girls like Anna actually live that life and it’s not some kind of reality TV fantasy. And I’ve been with girls like Anna before – so it’s nothing new to me. And I never did it explicitly for the money or the life – as most people think. I’m not that cruel and ignominious of a person. Even though I do love free things and pussy. Dating girls like Anna, your days are generally filled with extravagance, sexual debasement and depravity. Girls like Anna have the kind of privilege that most guys can’t keep up with for more than a couple of days.  Girls like her spend more money in a single dinner at a restaurant than most middle class Americans make in a few months. Have you ever tried a 1000-dollar bottle of vintage champagne? But you tend to look at these relationships like some kind of rodeo that if you only held on for the full 8 seconds you would win some kind of trophy. Even if it was some kind of sick and twisted personal trophy that simply said in some shitty font that I fucked the rich girl. Or maybe it’s the badge of masculine honor that your machismo and not your wallet or perfect pedigree allowed you to hold on for so long.

Truth be told, I am a very ambitious person and not just when I am looking for women to besmirch with my penis.  When I went to this company event I made sure to sit right at the head honcho’s table – even though I didn’t know it at the time. Anna’s father was an intimidating man to say the least. He was Iranian and although he wasn’t religious, he was very strict and came from the philosophy that you must work hard for success. This isn’t the same American philosophy where working hard is the equivalent of making it big and then resting on your laurels for the rest of your life. Anna’s father worked very hard everyday of his life and ran his company with an iron fist. Besides his company, he cared about his daughter more than anything. When I sat down at the table Anna was sitting right next to her father. She was young and didn’t look a day over 18. She was still daddy’s little girl and you could tell this by the protective shadow that he cast over her that reminded me of an eagle watching over it’s nest. But when he wasn’t watching over her – he was watching over his company. While he was eating, he would look up and give these fiercely territorial glances around the room at all his employees. His company was his lifeblood and so was his daughter. After about 5 minutes at sitting at the table I had the terrible feeling that I didn’t belong.

I was immediately attracted to Anna, but she seemed totally unavailable and not just because of the fact that was held on to so tightly by her father’s hairy Persian talons. Anna seemed like the kind of girl where if I tried to spark up a conversation she would shoot me down in that distinct demoralizing, I-own-the-world kind of way. As I was sitting there, trying not stare at her, she started making eye contact with me. It was one of those moments where you can’t believe the girl is actually looking at you. I was sure she was looking at someone right behind me. So I slyly look around the room and behind me to make sure no one was there. There was no doubt she was looking at me. It was one of those eureka moments. I knew I was in. I definitely wanted to bang this chick and knew I had a chance if only we weren’t at her father’s company event.  I was sitting at the table for what must have been an hour or so. Multiple courses came and went with a bevy of delights savory and sweet. But what the sweetest dish was definitely Anna. Between courses her father kept getting up and clanging on his glass asking various executive to make toasts and the obligatory hail to our leader mumbo jumbo to impress all the investors.  Even the plates, forks, knives, lobster shell crunchers were all made by Anna’s father’s company.

On first impression Anna didn’t seem prudish in the least, but did she seemed slightly conservative, and coy. That is until I got a glimpse of what she was wearing underneath her white summer dress. Eye contact quickly evolved into full on flirting. I was worried that we were being too obvious. At one point she motioned with her eyes and a subtle pointing gesture to look under the table. Classic. I look around to make sure no one is looking and intentionally drop my dessert fork onto the floor. Without letter her father catch me, I look under the table and notice that she is pulling up her skirt. She had on a pair of white tights with little white flower details, a garter and belt, but no underwear whatsoever. She gives me a full on view of her perfectly trimmed bush. Beautiful – she was full commando underneath her dress. I thought the table would lift up and flip over my erection was shooting so far out of my pants.

Flirting With A Rich GirlAt this point, Anna was in full on heat. I knew she wanted me, but it seemed like it was urgent at this point. If didn’t get something insider her in the next ten minutes I was afraid she was going to pounce on me from across the table. So with out letting one see my giant stiffy protruding from my pants, I get up and walk outside of the tent with the hopes that she would follow me. After a few quick breaths of fresh air, Anna comes out and grabs my hand. We race to a limo parked under a tree about a 100-yards from the tent. It was her father’s limo. The driver was still inside reading the newspaper. Anna and I get in and it’s ice cold, because the air conditioner had been left on. Anna tells the driver to take a hike. He gets out. We have the limo to ourselves. I was afraid he would immediately rush to the tent to tell her father that she was in the back of the limo with some guy, but she assured me that she has known the limo driver her whole life and wouldn’t do that. He was on our side, thank God. Anna lifts up her dress. She is skinny despite her incredible access to vast amounts of food. It takes African refugees years of famine to get that skinny.  She also had huge breasts – maybe that’s where it all goes – with pierced nipples. It was sexy to see a girl so reserved wearing nothing but a garter belt with pierced nipples bending over in front of me. And the danger of the situation – with her father so close – made it even more exciting.  I enter Anna from behind and her face and hands press against the tinted windows. Every time I thrust she lets out a little moan and her breath fogs up the window.

I go at it harder and harder and each time I thrust her nipple rings make a clinking sound against the windows. And just as I’m about to explode inside her, I hear the shuffling of dirt and the door opening. It was the limo driver and Anna’s father. Apparently the Anna was being a brat on the way to the event, so the limo driver was getting back at her. My lucky day. He catches us red handed. Imagine it: me behind his daughter with my cock inside her. Needless to say, he was beyond livid. I thought for sure in that moment that I was going to be murdered. He had every right to. I’m pretty sure it’s in the United States constitution that he was allowed to shoot me. It was his American right to kill me. She knew she really wouldn’t get in trouble and she had a devious smile as she tried to make herself composed by balling up her dress and covering herself with it. Anna’s father grabs me by my collar, as I’m wearing basically nothing below the waist except for a pair of loafers and high socks, and throws me out of the limo, but in his anger doesn’t throw my pants. By now every one in the tent could hear the commotion and came out to see what was going on. I was running down the polo field – completely naked from the waist down. What a sight.

After that day I never heard from Anna again. A friend of mind told me that he had read in the paper that she had gotten married. Another friend told me that her father had sold the company and was living on an island. Despite all that, I’ll never forget Anna. She was sweet and had a devious side. Just my kind of girl.

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