From Sugar Baby to Girlfriend of an Inmate: Part 1

By Katya

Dec 04, 2017

In November of 2014, I was fired from my waitressing job because of the toll that being a college student had taken on the quality of my work. I’d been unable to juggle a full-time job and a full-time education without compromising both (in fact, I’d had little time for anything but work, including any semblance of a social or dating life). The loss of my job caused me to realize I could’ve just as easily lost my education – something of utmost importance to me. My desires for more time to focus on school, for social/romantic interaction, and for leisure led me to resort to a strategy I’d used in the past: sugaring.

A Welcome Change

A much-needed break from sugaring had caused me to take the waitressing job in the first place. Thanks to sixty-hour work weeks, however, it wasn’t long before I began missing the benefits of sugaring: time to study, financial assistance, a sex life, nice dinners, travel, mentoring, great conversation – the list goes on. Moreover, I wanted to date, but I’d just lost my job because I was unable to handle my existing commitments. In other words, the last thing I needed was the added burden of a serious relationship. Therefore, it made sense to jump back into the sugar bowl.

Around the same time, I received a friend request on Facebook from a user named Dave*. His location was listed as Wisconsin (I was living in Manhattan at the time), he had a generic sounding last name, and he didn’t have a profile photo – things that usually would’ve caused me to decline a friend request. However, an unexplainable, nagging curiosity prompted me to accept.

Moments later, an instant message popped up on my laptop screen.

“Hey, gurrrrl!”

Still suspicious about him being a creep or otherwise untrustworthy, I responded curtly: “I need to see photos of you.”

“No problem,” Dave replied. “What’s your number? I’ll text them to you.”

I don’t normally give my number to strangers – especially random, mysterious men from the internet – but I wanted to know who the heck this guy was. (I later found out that he had simply seen my commentary on a mutual friend’s post.) I planned to get the answers I was looking for and most likely delete him – until I received his photos.

A Pleasant Surprise

I was captivated by Dave’s looks. He was rugged but handsome, with piercing blue eyes, high cheekbones, and a crooked grin. I was turned on by his masculinity, especially evident in a photo displaying his large hands and imposing stature as he worked on a Harley Davidson motorcycle, shirtless and clad in dirty jeans. As far as appearances go, Dave was a stark contrast to the professional, clean-cut type I was used to dating – and I liked it.

Dave’s personality had a more magnetic pull on me than his looks. He was charismatic, funny, well-spoken, and seemed genuine. We spent a few hours discussing our views, hobbies, and pasts. It quickly became clear that we had a lot of things in common.

After this conversation, we occasionally briefly caught up. Although we’d hit it off, I saw dating as an unrealistic prospect. I was unwilling to give up sugaring or be in a long-distance relationship. Whenever we chatted, however, our connection grew effortlessly and became harder to ignore. I found myself fighting what I knew deep down – that I had, in fact, developed romantic feelings for Dave.

In the meantime, I met my ex-boyfriend. We moved in together after a few weeks of dating. My ex didn’t want to “share” me with my sugar daddies, and I didn’t want to leave the sugar bowl. Still, my feelings for Dave had me longing for companionship on a deeper level than my arrangements offered. Because I saw a relationship with Dave as impossible, I looked to my ex to fill this emotional void by ending my arrangements and moving in with him.

During this time, Dave and I maintained intermittent contact. Although we kept things cordial and platonic, my attraction to him subconsciously nagged at me, and I began to wonder ‘what if?’ Things also weren’t going well with my ex. After a year of dating, he assaulted me and was arrested.

Letting My Guard Down

I moved out of my ex’s apartment and once again became lonely and financially burdened. A sugar daddy seemed like the perfect distraction and an ideal helping hand. I established an arrangement with an attractive thirty-something businessman who shared my childish sense of humor and affinity for “nerdy” hobbies, such as coin collecting.

As I grappled with the emotional aftermath of my ex’s abuse, Dave became a daily fixture in my life and was an unwavering source of support. Unlike before, I didn’t combat our rapidly growing connection with excuses about how we couldn’t work past our physical distance or how I was unwilling to give up sugaring for love. Our bond quickly superseded my attraction and feelings for my sugar daddy.

The Calm Before the Storm

In a perfect world, Dave and I would’ve proceeded seamlessly into a long-distance relationship. Unfortunately, however, it’s not a perfect world, and we were each keeping a major secret. Out of fear that Dave would judge, I’d remained silent about my sugaring. I later learned that Dave shared my fear of being judged, but for an entirely different reason: he was facing jail time, and his sentencing date was rapidly approaching.

To Be Continued…