Love & Sex

Everything I Learned from Having a Sugar Daddy

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The ad read: "Young Student Seeks Mature Mate For Fun."

Admit it, ever since you first saw Anna Nicole Smith and her much older beau, you've secretly wanted a sugar daddy of your very own. Much to our collective dismay, however, obtaining a sugar daddy isn’t as painless or quick as you may think. Although my personal sugar daddy experience wasn’t by any means calculated, I still had to try to make the “relationship” work. And it didn’t just happen, an older papa didn’t just single me out in a bar and approach me to boldly ask if I’d be interested in a mutual relationship, one in which sex and amity were exchanged for financial assistance.

It started during my first year of college. One night after work, I found myself too exhausted to go out and get wasted with my friends, but my mind was still restless – so I decided to do something just for thrills. 

I opened up my Facebook and stumbled upon an article on Craigslist encounters. I remembered talking to one of my friends about all of the weird "Missed Connections" posts on the site and somehow thought it would be humorous to make my own post. I wasn't looking for anything serious. I mainly wanted to see the types of responses my post would garner. 

To my surprise, my post, which was cleverly titled "Young Student Seeks Mature Mate For Fun," received numerous responses in a mere 20 minutes. While most of them were creepy and involved a variety of fetishes that I'd rather not specify, there was one that caught my attention. The sender’s name was Tom, and according to his initial email, all he wanted to do was “talk.” So that’s just what we did. He seemed shy yet down-to-earth, even through emails. We talked for days, until we finally met in person one night.

Before we met, I insisted he send me an image of himself, because you should never meet anyone from online without knowing what he or she looks like first. It’s Internet Safety 101, kids. I received a modest photo of him in an oversized navy blue sweater. His hair was slightly disheveled, but I found his smirk sort of cute in a dorky way.

I asked him to pick me up on a random street corner a few blocks from my dorm, since I didn’t want a total stranger and, for all I knew, possible crazy man knowing my actual address. As his car, an older Oldsmobile, approached me, I attempted to steal a quick glance at his face through the front window. Though it was dark out, I immediately noticed his piercing blue eyes, and that Navy blue sweater again. After exchanging awkward greeting gestures, I nervously entered his car, and we began to talk. We talked about practically everything. He reassured me that he simply wanted my company. It wasn’t until later that sex and money entered into the equation.

I might’ve been a “struggling” college student to a partial extent, but I wasn’t in a severe financial rut. I definitely wasn’t scouring my college town for an older man to supply me with things. Who knew creating an ad on Craigslist for kicks would lead to something actually substantial and pretty worthwhile? (Well, while it lasted.)

After Tom and I hung out a few times, I noticed that he would pay for everything. He never let me pay for dinner, an ice cream cone, or even my own shoes. Whenever I asked if I could chip in, he would reply, “It’s my pleasure, Viet.”

Because Tom was an avid collector and even established his own antique shop, he would always surprise me with an assortment of nifty knickknacks. During one of our first outings together, he let me explore his shop and pick whatever bracelets caught my eye. Surprisingly enough, I still own two keepsakes – an ivory bracelet with elephant engravings and a glass egg Tom gave me when he once visited me at work.

He never let me pay for dinner, an ice cream cone, or even my own shoes.

When I think about the typical sugar daddy archetype, I imagine an older, dignified business-type who spends extravagantly and lives in a decked out loft. Tom was an aloof, solemn business owner, who kept his purchases at a minimum and didn’t do too much, besides buy the occasional crepe and string his guitar. That’s the one thing I admired about him; he was extremely down-to-earth and lived simply, even though he grew up with money. Plus, when we were together, I didn’t mind that the only thing he noticeably spent money on was me.

Although Tom wasn’t unattractive in the typical sense, he didn’t sport a full head of hair or care too much about his physical appearance. He’s the type of guy who would parade around in the same hunter green plaid shirt and worn-in jeans almost every day.

But I found his modest sensibility endearing, and even refreshing. Maybe it was because I’m the type to overanalyze and freak out about things, so being with someone so at ease and unruffled felt almost comforting — our contrasting personalities balanced each other out. So yeah, I found him cute in his own spunky way.

Sex, on the other hand, was a totally different story. Our first sexual encounter was interesting, to say the least. I was hanging out at Tom’s place one night when he leaned in to kiss me, like he usually did, but this time, his arms pressed against mine as he pinned me down on the couch. This somewhat startled me, so I said, “Whoa, what’s going on?” He assertively replied, “I’m ready. Let’s do it.” By this time, we had been spending time together for many months. So the idea of sex felt right – or as right as it could.

As he went down on me, I noticed his huge bald spot, which was a slight turnoff for me, so I asked if he could slip on my beanie. I apprehensively muttered, “You look cute with it on.” I asked him to wear it the whole time, and from that moment on, I made him wear that beanie every time he gave me head and every time we had sex. That was the only way I could muster up enough energy to go through with each sexual endeavor.

I didn’t think about it before, but when someone is willing to pay you for certain “favors,” they’re most likely expecting “something extra” in return. Tom started giving me small amounts of cash from the get-go and – to my dismay – didn’t ask for anything in return, besides my companionship and company.

However, when things started to escalate on a physical and sexual level, he wanted certain things in the bedroom. He would even threaten to end things (in a joking but still serious way) if I couldn’t follow through. Tom was fond of role-play, and always wanted me to wear panties if we were about to do it. I honestly loathe panties and have no idea how girls can comfortably strut their stuff in them. The role-play part wasn’t too awful though. Tom enjoyed reenacting many scenes from some of his favorite TV shows –including Batman and Charlie’s Angels. Yeah, that’s right, Tom was Charlie, and I was always one of his distressed angels.

In the end, unless you have looks of steel and an on-the-clock plastic surgeon, your beauty will fade, and your supposedly clingy and steadfast sugar daddy will move on. He’ll find someone else to lust after and spend all of his cash on.

I mean, mine didn’t. But yours will.

Overall, Tom was an optimistic man, but he was prone to life lesson-filled rants of hilarity. Tom consistently advised me, “Never grow old if you can help it,” bursting into cynical laughter. What I believe he meant was that I should strive to maintain my childish affections. That’s the most important life lesson I learned from him. Growing old doesn’t have to dictate how you look at the world. Yes, it affects you physically, but like Tom, it’s totally possible to still have a wrinkle-free heart and spirit, despite all the accumulated age spots.

I finally decided to call it quits with Tom after about eight months of seeing each other. Our relationship became too emotionally and physically exhaustive too handle. Tom hated that I insisted on working. He hated that I always picked school over him. And he hated that I couldn’t spend almost every waking moment with him. Tom became evermore clingy and needy, and I couldn’t take it. I realized that our relationship was moving in a rather disastrous direction, and I needed to get off the sugar daddy train before it was too late.

I haven’t spoken to Tom since I ended things three years ago. Based on what a mutual friend told me, I’m pretty sure Tom found a new twink to financially fixate on relatively quickly. As for me, I’m happy to have my own financial independence. But I still treasure that glass egg.

Image via Jaysin Trevino