Money ruins everything.

“Can I see your ID, Hy?” he said suddenly.

“My ID?”

“Yeah.  Lemme see it.”

I dug in my wallet and handed it to him, his thigh pressed against mine in the horseshoe booth. He fumbled with something then pressed it back into my hand.  There was a $100 bill there now.

The tears I’d been holding back for the last thirty minutes sprang to my eyes.  What a relief!  We could finally talk about money now, I thought.

“I want to show you something,” I said and pulled out my phone and opened my banking account.  A little working wheel spun as we watched together.

Checking: -$88.83

Savings: $3.22

“You have no idea how badly I needed a little help,” and then with tears streaming down my face I explained to him the nightmare experience I’d been having with my bank and credit card over the past four days and how I had only $50 in my wallet until that moment.

I felt relieved, safe.  I don’t believe in white knights, but maybe I was wrong.

Will and I met on a sugar daddy site, a place where men seek [usually] discreet relationships with women who, in exchange for whatever kind of relationship everyone is comfortable with, receive monetary support.

The way the site is set up the SDs report their net worth and yearly incomes and what monthly expenditure they’re willing to provide.  The money ranges from “negotiable,” which has no value listed to “minimal” (a $1000 a month) to “high” ($10k a month and up).  Will listed his net worth at $2 million with a $250,000 yearly income, and as with most SDs had chosen “negotiable” as his desired support level.

When we first connected online I wasn’t interested, but his confidence and sense of humor won me over.  He asked why someone as beautiful as me was on a site like that one and I opened up to him like a cheap novel spilling all the dirty details.

How my divorce and staying home to start a family then start a new career had devastated my finances; how I sold stock, cashed out some of my 401k, and take on any and all side-work outside of my regular job I can possibly get in order to cover my bills; how I now make enough money to owe the IRS, but not enough to live off of; and how despite all that, my monthly expenses went up $1000/month last fall and I’ve been struggling to make ends meet ever since.

He told me he was impressed and reassured me that I’d done everything I possibly could.  I liked that this stranger’s sentiment countered my deepest fear of being a colossal failure.  “Life is hard sometimes, Hy,” he’d said.  “I’ve been there.”

When we met after three weeks of emails and texts I hadn’t planned to let him slip bareback into me while bent over my front seat, but I was overcome with passion.  We’d talked for hours and sipped our drinks in a plush hotel lobby and he assured me that he wanted to help in any way he could.  Later that night he’d text me “Don’t sell yourself short.  I can help you in so many ways.”

I wasn’t sure what he meant, but was encouraged nonetheless that he might be my fairy godfather of finances in this desperate time.

Accepting help from anyone in any form is difficult for me and asking for money is even more revolting; the situation in general puts me on my heel and while talking to potential SDs I felt raw and vulnerable discussing what they’d get from me in exchange for essentially being on their payroll.

Will had set himself apart quickly by not treating me like an object and so far everything he had said and done backed that up.  Everything was falling effortlessly into place: We liked each other.  I genuinely wanted to sleep with him.  He genuinely wanted to help me.

I stared at the $100 bill wishing my life were different, but feeling relatively lucky all the same; it was humiliating, yet overwhelming, a little hopeful.  I might really make it through this with his help.

I had cried en route to meet him, fearing rejection and humiliation at having to finally bring up our financial arrangment, but it was all for naught.  It was going to be ok…

And then, it wasn’t.

“You know, Hy,” he said as I closed my bank app and set down my phone.  “I’m so glad you waited to tell me about your situation until after I gave you the money, because had you opened with that, had you led with needing money, I’d have given you the $100 (because I’d already set it aside for you last week) and walked out and never spoken to you again.  That’s really wonderful of you because now I know you’re genuine and more importantly, you know I’m genuine.”

I couldn’t believe my ears.

The next hour the tears continued as we debated the logic of his words.  “I don’t know why you insist on being upset and ignoring my compliment!” he argued.

“It’s not a compliment, Will, because I was only lucky just now.  I came here knowing I would have to ask you for help because I’m so desperate and you’re telling me that had I done that you’d have walked out on me without discussing a thing with me and that’s shitty and wrong.  You have no idea how hard this is for me!”

“But why is it ok to ask me for help and none of the other guys from the other sites??” he asked angrily.

“Because,” I said between sniffs, “I already told you, those other sites aren’t set up to discuss financial situations.  Seeking Arrangement is!  I can’t tell men I meet on AFF, ‘Hey, I need help with my bills this month,’ they’ll think I’m a fucking prostitute!”

He talked to me slowly and calmly, like I was the village idiot; I shut down.  Nothing I said could convince him of my vulnerability or how what he said was so belittling, disempowering, and outright appalling.  A woman he met on a sugar daddy site is not allowed to discuss her financial situation with him first lest she piss him off and he take his ball and leave.  Screw you, Hy, for having needs and making them known to me before I asked.

I absentmindedly watched the bartenders do their busy work and wished I were somewhere else.

He reminded me that we’d only met twice and to have some perspective when I couldn’t stop crying. But how could I possibly stop the river of emotions that had spilled over the dam?  Humiliation, degradation, guilt, rage, helplessness, embarrassment, sorrow, fear.  Each one a torrent in its own right.

I felt deflated as I sat beside his bulk.  Something had just been bludgeoned between us, the little flame of hope and friendship was now a black, pulpy mess.  He was mad that I seemed to be deliberately missing his magnanimous attitude towards me and I was crushed that I was treated like an ingrate with no agency.

Numbly, I let him walk me to my car.  He made an inappropriate joke about fucking me by my car again.  I kissed him and tried to flirt, but I felt broken and listless.  I sobbed on the way home and opened a bottle of red wine.

Deep into my cups I reached out.  “I’m free Friday after all.”  He laughed and said he wished he was fucking me right then.

I felt lost.

What was I doing??  What was I trying to salvage?  This is not the arrangement I seek, to hope that the guy I’m seeing will toss me some cash because he’s in a good mood.  If I were financially stable, that would be fucking amazing, but I’m terrified each month that I won’t be able to pay my bills and I had made that abundantly clear to Will.  I want a friends with benefits who understands his cherry to the situation sundae is money as I understand my cherry is discretion and companionship.

Money is a delicate, powerful thing and it reminds me of anthrax.  It rips families and friends apart, destroys business partnerships and marriages; I’ve been reduced to tears because of it all week.  Money isn’t everything, but when you don’t have enough it’s all-consuming because it equals survival.  Money equals safety.

One thing that has become abundantly clear to me through all of this is I am wholly unprepared for how other people feel about their money as it relates to me.  Will became defensive and dismissive because I suspect he feared I was only there for his money and the irony of where and how we met appears to be completely lost on him.  It appears I wasn’t cut any slack.

In that booth with him, weepy eyed and defeated, I watched helplessly as he moved away from me, my tears and ingratitude driving him away and I felt even more sorrow because in that moment I realized that I had somehow also hurt him.  I didn’t hear from him the entire next day.

Clearly, neither of us are fit for this sort of arrangement.

A 40-something single mother who writes honestly about sex, body image, D/s, relationships, her nervous tics, and how much she loves to fucking fuck. She also likes to show you her tits.

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22 thoughts on “Money ruins everything.
  1. Wowzers….intense…..i think i am able to see both perspectives and i think you can too Hy…..but that doesn’t make it easier…….you are SO fucking right about money….it IS the root of all evil… are able to explain your feelings so well even though this is a difficult concept to grasp…..i am thinking about you!

  2. I hope I can make sense with this comment without coming across as a complete jerk. And if I don’t succeed, I apologize in advance. I should preface this by saying that, I could never be in the Sugar Daddy role because I just can’t afford it. I don’t use the services of escorts though I’m completely supportive of and if I’m being honest, intrigued by the sex work industry. Make no mistake, the ladies who participate with Sugar Daddies are sex workers, even if no sex actually takes place. And I don’t think they should be ashamed of that.

    As a man over fifty, it sounds to me like your guy had built up this knight in shining armor fantasy. He didn’t want to imagine you so much as a sex worker but the real GFE where he could provide you with cash without having to admit to himself that his gift was an exchange for something. By you revealing your need, he could no longer keep that straight in his mind. Sadly, you already liked him. You had no intention of being a sex worker, yet that was how he saw it.

    I have a close friend who lost her near six figure job suddenly, and very unexpectedly, two weeks before Christmas. She is a widow and she has a five year-old. She told me that as she scoured the Internet looking for jobs the idea of being an escort kept coming back to her. One ad on Craig’s List for jacking a guy for $80 in his car out of pure desperation led to several ads on Backpage for companionship at $120 an hour and within the first month she had figured out the game enough that she was advertising on high end pages for independent escorts where she now won’t even see a guy unless it involves dinner and $300. She very strictly watches the clock and she reports that actual sex happens less often than you might imagine. These men just want a woman to listen to them talk and make them feel special. She now is back at work full time but has retained a couple of her more generous clients. These are professional men who have such tight schedules that they can’t seem to make a “normal” relationship work, therefore they are willing to pay a woman for a stress free date that may or may not end up in bed.

    This isn’t me saying, “Hy, become a prostitute”. But what I am saying is that your guy would not have been on that Sugar Daddy site if he hadn’t had that type of arrangement in mind. My escort friend tells me that often, her clients want to ask her details about her business. How many men, how much do other’s pay, etc. She told me, The client is paying for a ticket to the Circus, not a peek behind the curtains. Your man gut a peek behind the curtains and it ruined it for both of you.

    1. How interesting! I wish I knew how to do that and make it happen. I’m always afraid of getting arrested and making it clear my body isn’t for sale, though my company could be. I’m not sure if the distinction is important to anyone, but me, but it’s there nonetheless.

      And no, you didn’t come off as jerky whatsoever. Thank you for your thoughts on this. It’s really helped me process what happened between me and Will that day. xx Hy

  3. We will never know… that is the meat of the story of life… your writing is wonderful… honest and raw. Money and power… what a fuckity fuck fuck mind screw it can be. Know you are loved and if I had it… well I’d share it.

  4. I don’t think you can go into that kind of situation and be sensitive. I wish you had taken his comments on the chin and moved on as this could have become a satisfactory arrangement for both of you. It still could. My man and I had a tough time getting together for many reasons. During our time apart and our time together we have given each other money to bail the other out, often when in a vulnerable situation.
    All relationships are transactional in some way. We just don’t always define clearly what we are exchanging.

    1. I was sensitive because I was negative in my bank account, not because he gave me the money. It wasn’t like I’d just turned my first trick, or something lol :)

      1. I understand why that would make you sensitive but using such a dating place you both knew the score and if you had an abundant source of income you wouldn’t have been using such a site in the first place. If he had other attributes, rather than money to offer, he may not have needed the dating service. You both knew he was the money, you were the babe- you both liked each other, wanted more, so ….
        May recently posted…Virgin at 41 – can YOU imagine what it must feel like?My Profile

  5. This was tough to read. I find it hard to accept money from others, but then I try to remind myself that people are allowed to make their own choices about money, and when the expectations are clear, there’s nothing wrong with receiving it.

    Some people expect nothing. Some people expect something.

    I’m sorry you had to go through this. I hope you come out the other side.
    Ani recently posted…Do Not Spare Me From PainMy Profile

  6. Oh Hy, how painful. I think you weren’t ready for this. He didn’t need evidence of your financial straits. You didn’t need to be critiqued on how you expressed your money woes. Can you both put the money to the side for a little bit as you get to know one another? Are you ready to feel beholden to a man? My heart goes out to you.

    1. It’s fair to say that is an accurate statement, Maggie. I know it now, but I wanted him to know why I burst into tears when he gave me the $100. We’re still talking… but it’s different for me now. I don’t trust him. But I’m not worried about feeling beholden, so that’s good.

  7. JFBreak nailed it what he said about a ticket to the circus, not a peek behind the curtain.
    Hy, I’m a former pro, and I still have a couple of long time SD’s so I do know what I’m talking about.
    I remember one client who used to be too personal and caring and it would always upset me. He would say things like I was too nice and innocent looking for the business, You don’t need to do this for a living, etc., etc. Hell it’s not like I always enjoyed doing it and then he’d whip his dick out and treat me just like the others. Gee Dude! Thanks for caring! LOL!
    Part of being a good SB is being part good actress. Give them what they want , and leave out the personal stuff. I know it gets confusing when you meet one who says he wants an open and intimate friendship, but really you mustn’t divulge all your woes as tempting as it may be. At least not until there is some trust built and you know he truly is caring enough to not get scared away. I’m not saying your reaction was wrong Hy, and I do think he was kinda confusing and contrary. I can understand completely why you felt the way he made you feel…. Been there… HUGS!!

  8. This made me nauseous. His actions and words; not yours. I don’t know if a relationship that is based on a financial arrangement can work for you or not… But in any relationship, basic respect is essential. Wishing you the best in love and finances and that someday soon you’ll be grateful they didn’t get too blurred.

  9. Forgive me; I’ve “bypassed” all other replies above, so as to take the “full risk” (and responsibility) of responding to you with my own words, uncolored by other responses…

    Firstly, I haven’t the FOGGIEST – really – re SD cuz I’ve never been one, and have never had a SM (if such exists; but in a world of “equality”, why not??).

    However, having read your story, AND UNDERSTANDING its TWO sides, I feel I should point out one thing which seemed very clear to me:
    If you had “opened” with your “need” FIRST, then you’d be “needy” and/or “desperate”; and in this, is how I see where Will was coming from…

    The (limited?) way I understand a “SD site” as a “dating”-type (or “connection”) site, is that it has the potential to bring together Men who WANT to spend their money they set aside, on Partners (is it _always_ women?) who are happy to have sex with OLDER MEN (hence “sugar DADDY”).
    That is to say, it’s NOT a “prostitute” site — it’s not Partners (women) who are “happy to have sex for money”.

    Is that a “fair” distinction for me to make, with my lack of experience?

    The distinction I make “revolves” around money, ONLY inasmuch as a “sugar daddy” concept — to ME at least — is that the SugarDaddy is GIFTING the money, NOT being ASKED for it, NOR being EXPECTED to PAY (as he would if it were a prostitute, “selling a Service”).

    Does this help, at all, in perhaps re-coloring “how” it MIGHT be seen that BOTH of you HAD A POINT, but from “opposite directions”?

    Also — as I lack relevant experience — is it “fair” to PRESUME that ALL SugarDaddies “always” want to GIFT some money (or even gifts!) to their SugarDarling (or whatever it is the younger partner is called)..?
    In which case — unless the Website itself (I’ve not looked at it) lays out “basic ground rules” which says otherwise — is there “no need” to discuss money “up front”?
    (Gosh, now I’ve used that phrase — “discuss money up front” — it makes it feel decidedly “prostitute-like”..) >_<
    That is, a SD doesn't "pay for services rendered".
    A SD "gives money/gifts" as a Dad might give to his daughter. It's SEPARATE. :)
    (Except the SD site "semi-formalizes an arrangement"…)

    I take Will's "now I know you're genuine", to mean "genuine" about being a SugarDarling (whatever), and about having Will as a SugarDaddy.
    i.e. he will give money cuz HE WANTS TO, and NOT because "you need it".

    It kinda implies that your position should be more of "I'm happy to be intimate with an older man", and that "for the fun of it", rather than "because he'll give me money later", no matter how much you need it, in YOUR core truth of the matter..

    Certainly, I'm sure everyone on a SD site will understand that SOME value (money/gifts) changes hands from Daddy to Other, but I feel that the overall concept isn't supposed to "expect" money/gifts, but rather to show Gratitude AFTER it's been received.

    I hope this helps…

    1. Sh*t … forgot something.

      It doesn’t have to even be about SEX.
      It could just be COMPANY / companionship.
      (Just an additional thought.)

  10. Hmmm. Why was he on a site looking for a lady to ‘spoil’ if he really did not wish to do so? Waste of time for everyone. I know we have a myth in our culture that a man is supposed to be able to get hot sex from any and every women he wishes, with no strings and conditions but life is not that way, not unless you are in a James Bond movie.

    In his case, it seems he knows such but still wants to be play a game, when dealing with reality.

    You were vulnerable. He was unrealistic, as humans often are.

    Sorry whatever friendship you could have created is ruined. But under the circumstances, it would be hard to create a friendship.

    Money is not toxic, it is the intent which can be.

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