Her evening with Jon, for the most part, was a good time. Except she was getting really tired of dating or hooking up with younger guys. She enjoyed how desired she felt when she was with them, but the novelty was wearing off. She wanted an older guy, or at least someone her own age. Someone who was in a similar place in their life as she was, with whom she could possibly start a real relationship.
Well, those guys didn’t seem to exist. Anyone she did match with who was her age or older were either married and ENM, or divorced and bitter, and only looking for fun. Behaving in ways that helped her understand why they were divorced. At the same time, her other woes in life were creeping in, as well. Specifically, her financial struggles.
She had never been very good with money. However, since moving home, she had been able to pay off her student loan, as well as finance a car. Her big issue now had been the credit card debt she shared with her ex. Over the seven years they were together, she let him accumulate so much debt in her name, that she was still drowning in bills almost three after leaving him. She was diligent at making her payments, but the interest on both cards were just killing her and she had made very little headway in chipping away at the principle.
Finally, after several years of being back home, she was able to secure a consolidation loan to pay off the thousands of dollars she owed on her cards. Her new payments for her loan were much less than she had been paying, and the interest was much more reasonable. She was so relieved to finally be on track at getting her debt down. Even still, inflation and cost of living had increased astronomically, and she still struggled on the daily to even just get herself to work with gas prices being so high, just as one example.
One day, as she scrolled through Instagram on her lunch hour, an Influencer she followed was promoting her latest podcast, an episode entitled, “Sugar Baby Confessionals” … or something to that effect. The money struggle is REAL, and the idea of funny stories about young, smart, empowered women dating older men to better themselves financially actually really intrigued her.
She downloaded the podcast and gave it a listen. During one of the confessions, one of the women mentioned the website on which she had met her Sugar Daddy. Overwhelming curiosity compelled her to go check it out, but she couldn’t look through the selection of rich old men without creating a profile.
She never thought she would ever consider it – having a Sugar Daddy? Being a Sugar Baby? That was for dirty old men and gold diggers. Except here she was, mid-30’s, living with her parents going on 3 years, financial independence continuously feeling out of reach. She felt desperate. Was this a sign from the Universe that she was meant to pimp herself out to dig herself out of her financial hole?
Probably not. But like.. maybe?
She caved and decided to make a profile. She added the six required photos, having cut off her head in all of them to protect her anonymity. It also allowed a private album to add full face pics in case you connected with someone and wanted to share your identity. The only way to see that album is to request access, and wait for the other person to approve or deny.
She filled out the bio as vaguely as possible, and began to navigate the website. Within a few minutes, her photo requests had filled up and she had at least a dozen messages. Some of the men had blurred photos, some not. Some were as old as late 70’s, others as young as mid-30’s. Some were actually decent looking, most were old and creepy.
She scanned through the messages and found a somewhat decent looking guy. Late 40’s, only slightly balding. Heavier, short, but very rich. His message was friendly and he seemed sweet. What harm could it do to reply?
They started chatting and he immediately showered her with compliments. He asked her what she was looking for, to which she replied, “I have no idea. First timer. Just seeing what this is all about…” So he shared his story, instead.
He explained that he had been a Sugar Daddy for 11 years, and that he’s married but his wife was asexual due to a disability. He was looking to connect with someone to meet for intimate dates once or twice a month, and to reward with gifts or “donations”, as he called it, towards whatever she was struggling with financially. In her case, that would be donations to her Pay-Off-Her-Loan or Buy-a-House funds. He also bragged about his oral skills, and mentioned that he has “an extremely huge dick” – direct quote.
Well, now then. Doesn’t that just sound like the perfect scenario for someone looking for that kind of arrangement? She was intrigued. How bad could it be? Pretend to be into this not-great-looking rich guy, get off a bunch of times, and leave with $X to put towards her finances. Maybe she could be down for that?
After an entire day of chatting on the website, he asked if she would mind switching to Snapchat so they could converse more easily. She was hesitant, but agreed. Once they had added each other, he immediately asked for nudes. She declined, and asked for some better face pics before she agreed to send him anything.
He sent her two more pics. Both typical, older guy selfies. Like what your weird uncle might put as a Facebook profile pic. Still decent looking. Now that she had a more concrete idea of who she was talking to, she agreed to send him another pic. Not nude, she was wearing a bikini top and shorts, and he fell even harder for her. Furiously typing out compliment after compliment. Damn. She could get used to this!
He then asked her, “So are you sure you don’t think I’m like, gross?” She paused and really contemplated as to how to reply. She knew she had to be honest, and she was aware that some guys like this often get off to being put down. Not that that’s what she wanted to do, but her honest opinion was not necessarily complimentary.
She told him that no, he wasn’t her regular type, but that he seemed nice and she had been enjoying their conversation. She also reminded him that she was new to this and asked that he be patient as she got herself accustomed to the idea of this type of arrangement.
He replied saying, “I’m no one’s type. I’ve never had sex without paying for it…” She knew she was about to get sucked in to a pity party, but she still took the bait and said, “Well how can that be true? You’re married, aren’t you? Your wife has to have seen something good in you to marry you?” To which he replied, “She’s from another country, it was a a long distance, online arrangement. She’s also blind. The only woman who was ever willing to give me a chance can’t see how ugly I am. And even she doesn’t want to fuck me…”
She’s also what!? Blind!!?? How do you respond to that!?
It was both hilarious and kind of heart breaking at the same time. She took her time to formulate a non-offensive reply, and decided to go with, “Well, I’m really sorry to hear that. Sounds like you’ve had a rough go…”
He took a littler longer to reply than he had been, but then said, “okay take care”. She was confused. How could he go from one moment saying he wanted to spoil her and do all these sexual things to her, to then just blowing her off. At the same time, no way was she about to beg some sad, lonely, old guy to continue chatting with her. So she replied, “Oh… ok? take care.”
He replied quickly saying, “Well you said I’m not your type…” She was somewhat taken aback because she figured he would have expected an answer like that. She also felt that her reply had been fairly kind, and she was trying hard not to be hurtful. She took a moment to organize her thoughts, then replied:
“You asked me a question, and I gave you an honest answer. I told you that no, I don’t typically go for guys like you, but I also said that you seemed nice and I was enjoying the conversation. We met on a Sugar Daddy website. We’ve chatted for several hours now. Whatever arrangement that we might have come to would have been an understood exchange of financial assistance for physical intimacy, regardless of whether or not you’re my type. But you’ve ruined it now. I’m not here to play therapist, but I wish you all the best.”
As soon as she hit send, she decided that that was enough of a glimpse in to the Sugar Daddy world for her. Plus, she knew deep inside that she wouldn’t have been able to have sex with someone under those circumstances, even if she was getting paid well for it. Not only that, she didn’t have the time or the mental bandwidth to be someone’s emotional support lay.
She blocked and deleted him from Snapchat, and then deleted her profile on the website. So much for that financial boost. Not to worry, though. The Universe had another trick up it’s sleeve…