New York: The City that Sleeps Around?

Growing Promiscuity through Hedonism and Financial Gain


The City that Sleeps Around

The City that Sleeps Around

When describing New York, no matter where you come from, everyone first thinks of the cliché, “New York, the City that Never Sleeps.”

That may have been true when it was first said a million times back in the day, but these days we New Yorkers have a progressive spin on it.

My new progressive saying, “New York City…The city that…Sleeps around” stems from my observations around me from others.  The main incentive(s) of New York growing promiscuous involves hedonism and financial gain.

I am not making any judgments on anyone. I am a liberal and believe as long as you are not harming anyone or animals do as you please. I wanted to get that out of the way before I go into great detail about the people I have met that let me gain inside knowledge of sex in this great city of New York.

When I first moved to Queens, I settled down in Woodside. It is a quaint and old school (amiable people, mom & pop shops) that is close to midtown Manhattan and happens to remind me of the Bronx.

I rented a bedroom in an apartment with three other young, single women like myself. I grew close with two. The other one was an immigrant that kept to herself.  The two roommates that I befriended were both free spirits in their own right and, for the most part, not hard to get along with.

The first roommate, let’s call her Holly Golightly like from the novel and movie, Breakfast at Tiffany’s. She was very proper and friendly, and just like in the novel, it made you question if her occupation was a little unorthodox if you know what I mean. The way she described her job, it sounded shady.

Holly first told me she advertised for doctors who weren’t social and creative. Holly would come home late at night in tight, scantily clad dresses mostly drunk. She would tell me her clients took her out to a nightclub or strip club after work, and she has the company credit card to take unlimited Uber rides. I would see her hair nicely coiffed as she would catch a cab in a pretty dress.

I ran into her in the grocery store and heard this enchanting voice from behind me. It was her. It was impossible not to think this girl was so sweet and kind.

She was also very easy to live with. She was from Sweden, was very thin, and used to be a model when she was a teenager. She was very vain, however, and would come back from the dermatologist with swollen lips from collagen. She was obsessed with her appearance and staying as thin as possible.  As soon as I moved in, I loved her.  She was a cute girl with blonde hair and had the healthiest diet I have ever seen. I think she was afraid to eat anything fattening.

One time she came out of her bedroom, and she confessed to me that she just scarfed down a cheeseburger and felt so bad about it; you would think she was confessing to committing a crime. I admired her for being so committed to being healthy and staying so lean. She would always shop at organic grocery stores, and only once did she make anything caloric, and that was when I spent Christmas with her when she made this delicious Swedish Strudel.

She was more of an acquaintance to me than a friend. I could tell she wanted a boundary between us, not friends, but an amicable co-existing relationship for two roommates to share, and I appreciated that. We would have many conversations when we were both in the kitchen. After seeing her coming home late drunk on numerous occasions, I learned much more about her.

“I think this guy is stalking me! He works for the CIA and got all this information about me!” Holly said in this in sheer terror and told me she met him online on some dating site. She then went into great detail about how she is a sugar baby on Seeking Arrangements, an escort site where rich men look to date and spoil young women who are looking for money; it is like glorified prostitution.

It is mostly rich men seeking female sugar babies, but there are rich women on there too seeking male sugar babies.

Most of these sugar daddies are married. They take them on lavish vacations, buy them cars, pay for their living expenses, and more.

After Holly regaled me with this new piece of information about herself, I was stunned. She never iterated to me what she had to do in return to receive such lavish gifts, going out to upscale restaurants, and just being spoiled. Don’t worry, I can read between the lines. “I am done with men. They treated me horribly and used me, so why not turn the tables and use them?”

That was her ulterior motive for signing up for such a risky and hedonistic website for financial gain. She figured she could use men for money since she viewed love & romance in such a cynical light. It never ceased to amaze me how proper she acted when describing to me Seeking Arrangements. She then proceeded to show me how the site works. “Here is Matt’s profile,” she said as she logged on to her account.

“Men are supposed to fill in their income on the bottom of their profile. Some sugar daddies’ income is verified, but most of them don’t want to because they are afraid they will be found out.”

I had never seen any of this up until she showed me; I have heard of it but never met anyone that was on the site and showed me how it worked. Then Holly intimated to me out of despair: “I had to figure out all of this myself! I had no one helping me and had to figure out for myself how to play the game.

I need the money, and this is the best possible way to get it.” After she filled me in on her extracurricular activities, it dawned on me that her “occupation” as a marketing specialist for doctors must be a sham. It was shady to begin with, but now all the missing pieces of the puzzle have been completed.

Now it all made sense. The drunken nights, the infinite Uber rides, all that time, she was vacationing in Miami during the summer in a timeshare in order to advertise her “marketing skills.”  It all came to the surface. She then proceeded to tell me that she was dating older, established men in these timeshares in Miami.

“Ugh, he has a teenage son and keeps the house so messy,” Holly complained to me that her hedonistic bliss with this sugar daddy was shattered once his teenaged son came home to live with him.

One night very late, I thought I heard someone come into the apartment. I was scared and did not leave my bedroom till later. When I did, I noticed Holly’s bedroom was all of a sudden unlocked. She was in Miami at the time, so I was petrified. I automatically alerted my landlord. Holly came home shortly after in a tight sports bra and shorts looking beside herself. What could’ve happened? Was it a sugar daddy turned bad? A bad transaction?

I never did find out but was lucky nothing tragic happened.

This went on for months; I shared the apartment with her for up to a year when all of a sudden, she had another piece of news to share with me. I had this strong intuition that she was going to move out; I didn’t know why other than a sinking feeling in the pit of my stomach. She had told me that in addition to cozying up to sugar daddies in the timeshares in Miami, she was also conventionally dating online too.

She came home from Miami one weekend: “I met this great guy from Tinder! We spoke on the phone, and his new apartment was right where I was staying in Miami Beach. He pulled up in a Porsche and a dozen red roses and wined and dined me at Sushi Samba!” She was in love, I could tell.

I felt like this was a different person. Is this the same woman who was so cynical about love and said she would only use men for money? The same woman who signed on to Seeking Arrangements as a sugar baby just looking to make money?

I felt like she was possessed or something. For the next several months, she emphatically expressed to me that she was in love. She went to Florida every weekend to say with him. “I never thought I could believe in love again until I met Joe.”

I had no idea the circumstances of why she was moving out but knew she was going to.

I returned home one evening to find her cleaning out her kitchen cabinet: “Would you like the rest of my flour?” I was shocked. “You’re moving out?!” I knew it! “Yes, I am moving to California with Joe once he returns from Hawaii.” I was stunned and just in utter shock.

She met this man for like a minute, just started dating him here and there down in Florida, and now she’s moving 3,000 miles away to live with him? I didn’t think this added up, something shady again must be going on.

She would argue with him at times on the phone while they were both “looking for places to live” online with her being here in New York and him in Hawaii.

“Joe is missing!” I asked her what she meant. “Joe hasn’t come back from scuba diving yet, and I’m worried about him!” I told her she should call his hotel room; she was in shambles. Eventually, she said she found him, and he was ok. I’m telling you this whole relationship made no sense.

Then she showed me his photo. He looked very creepy with a huge grin on his face to the point that he didn’t look sane. I had googled his name, and it turned out he was once on a reality show, and people had said he was creepy.

According to Holly, he is a graphic designer and was designing his own bikini line, she said she wants to collaborate his designs with him and work together, and most of all make sure he does not get too close to the models she expressed with envy.

The second roommate was Carol. She was originally from Rochester, and we had become much closer and actual friends. She wanted to hang out with me, and I had accepted several of her invitations to spend time with her and meet her other friends. She was a social worker but had a great passion for acting and dance. She went to Cornell and majored in dance and was very talented besides. She was the textbook definition of a free spirit.

She was nice and helpful to me, and both our jobs at the time were similar, so she would give me advice when I was stressed out at work. We didn’t always get along, however, and would clash. She was notorious for leaving her dirty dishes in the sink for up to a week.

I never understood what the big deal was to wash dishes that only she used? It was only a few and wouldn’t take long to wash, but no, she left it lingering there forever, and it was one of my biggest pet peeves. I also have never met anyone with the biggest mood swings until her. After growing close to her and becoming very good friends, she had invited me to an underground rave in Brooklyn.

I didn’t know much about these types of parties other than the fact that a lot of people like to go to listen to EDM and trip on acid and ecstasy in an abandoned warehouse or building.

She already had told me that a lot of her friends had alternative relationships with their significant others. This was the first time that I heard about this other than watching couples attending swing parties on MTV.

She would tell me that all her friends had polyamorous relationships, meaning they were all married with children but had an open marriage and were free to form intimate relationships with other people, kind of like mutual cheating.

I found it pretty unique of her that her vibe attracted such free spirits who embarked on such intimately unconventional relationships. So, the night she invited me to this rave in Brooklyn, called House of Yes, I decided to accept her offer.

I was bored, and it was a Saturday night, and to be honest, I was quite fascinated about checking this out. We left very late that night. She told me that a few of her married and single friends would be there. It was the dead of winter and so cold out that night. The train ride was almost an hour, but I’m glad I went although I got back around 4 AM.

I met her married friend, he was nice, and I could tell he was hitting on me, he wanted me to be one of his new acquaintances in order to join his polyamorous lifestyle.

He didn’t bluntly tell me this, of course, and he intimated it by telling me that he wanted to cook me a “special dinner.”   I didn’t answer that night he asked me at the underground rave, I just said thank you.

Later I told Carol that he wanted to cook for me, but I didn’t feel comfortable, and she told me I should just tell him that. After that night was over, I wrote off ever attending again; it was more of a once in a lifetime experience for me. Plus, I felt too old to party like that all night long when I did when I was in my 20’s, interesting experience indeed but not for me to repeat.

Fast forward a few years to when I was at a singles party…I went to the bathroom and saw this woman who stood at 6ft1. She was enthusiastic and full of a lot of positive energy, so I said hi and introduced myself to her. She was one of the attendees of the party too, and told me she couldn’t find any of the food they claimed they were providing. She was full of life and so friendly, and I wanted to befriend this woman who was in my age range.

After all, she was single too and never married with no kids, that’s hard to find in my age group. After we exchanged a few pleasantries, we also exchanged phone numbers. I had begun a friendship with her that was unlike any other – and even that is an understatement of the year.

We both loved to eat and shop at the same stores, so we had that in common. At the beginning of our friendship, we would get together to indulge in food such as prime rib to Greek food. She liked to hang out too like me, and so we would go to the occasional bar or lounge and get a drink.

After participating in these activities together for a while, she finally confided something to me. “Now that we became good friends, I’d like to tell you something.”

It sounded like she had a dirty little secret. I couldn’t imagine what her confession was. She then proceeded to tell me that she recently started engaging in a hedonistic lifestyle that entailed attending sex parties, signing up for sites such as Friend Finder and Fet Life – websites that cater to people looking to hook up strictly. At first, I was a little taken aback but rebounded quite quickly.

After all, as I had previously said, I am a die-hard liberal, and as long as you aren’t hurting anyone who cares what someone does in their personal life?

I was somewhat curious once she told me this. She then went on to tell me about these sex parties. She first discovered them when she posted an ad on Craig’s List looking for a partner to go to these discreet gatherings. She found someone to join her and ended up meeting a man who organizes these events throughout the east coast.

He was an older gentleman and based in Georgia but would come up to New York and host his parties in upscale hotels such as the Gansevoort. I was in awe of the energy this new friend of mine had.

She could work all day and party all night with no sleep and repeat the next day while being all full of alcohol. It sounded like she wasn’t even human. She would tell me about her experiences on Fet Life, where she met couples at a discreet location to grab a drink and indulge in covert pleasure in a hotel room. I thought it sounded risky for a variety of reasons, but it seemed to float her boat and give her a new lease on life.

She had told me that one of her friends was a bartender at an S&M club downtown in the Financial District and was planning on going there after she hung out with me one night. On a whim, I asked her last minute if I could join her.

I ended up finding some rando on Tinder, who said he was a doctor to meet us and buy us drinks. So, after she said I could join her at the party but the admission was up to $100 and couples only. The guy ended up being a total jerk, but I took him with me, and we went as a couple. It was a dark and dimly lit loft in an abandoned building.

They played great music, and most people were wearing scantily clad patent leather outfits whipping each other—another once in a lifetime experience for me.

My friend looked great and all dressed for the occasion. She changed her outfit after we met, and she had on a silk top and short shorts. I thanked her for inviting me and ended up leaving very late at night, where I left much after her.

The doctor was such a jerk and just looking for one thing, so we ended up having a huge fight where he ended up abandoning me. My cell phone’s battery dwindled down to the point where the battery almost died, and I didn’t have a charger.

The party ended at around 4 AM, and everyone went pouring out in Uber rides except for me. The Financial District is desolate during non-working hours, so imagine how deserted it was on a Saturday at 4 AM?

Luckily on my last 5% of my phone’s battery, I was able to get a Lyft to drive me home but was panic-stricken, and it was very windy out and freezing being all alone.  Another night I chalked up to another once in a lifetime experience.

People have different reasons to engage in this life of hedonism. For some people, it is a hobby and a passion, like taking up horseback riding. For others, it’s a way of making money and paying your bills. I’m not judging these people who go on Seeking Arrangements or Fet Life, but isn’t it a bit scary and risky, to say the least? What if you meet a maniac or get a disease by engaging in such risky sexual intercourse?

I understand it is a tempting way to make money or for some a new hobby or outlet for them to enjoy life, but I feel like it is way too much of a risk and not worth the consequences.

  1. Avatar of sherri danziger
    sherri danziger says

    You have to be the funniest, just love your creative style, a great way with words. .. fabulous novella… loved it…. kudos.

  2. Avatar of sherri danziger
    sherri danziger says

    Your creative style, your wit so funny, love it.. Fabulous Novella. Felt like a flashback from Sex and the City.. A great read, fun, informative wow, to put a smile, and a chuckle for us lucky readers. Congrats, Kudos.

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