From Insecurity to Empowerment: My Journey with a Confident Sugar Baby

When I first thought about becoming a sugar daddy, I wasn’t in the best moment of my life. Work was taking up all of my time, which meant that I didn’t have a consistent workout routine or good eating habits. Alright, you can read that as, I never worked out, and I ordered take-out every night. I felt terrible, and worse, I felt terrible about myself.

So, you can imagine that dating was out of the picture.

Sure, anyone who’s seen Seinfeld saw George Costanza landing beautiful woman after beautiful woman, even though he was short and balding. But life isn’t a sitcom. And there are only so many times that you can approach women in bars and get that “how dare you talk to me” face before you give up completely. Blind dates were disasters. And online dating was even worse.

My female colleagues pretended to be shocked that I couldn’t find someone. “But you’re so successful and nice! And you play guitar! Women love that!” they’d say. But, then, they didn’t want to date me either.

So, on one, admittedly drunk, Friday evening alone, I signed up for a sugar dating site. Now let’s be honest, I’m not the richest guy you’ve ever met. But I live comfortably and thought I could definitely treat a girl to a weekly night out. Maybe we could even plan a trip to an all-inclusive resort in Mexico or Brazil someday.

And that’s how I met Mandy. Well, her handle at that time was Musical_Mandy because she was trying to break into the music scene. And we hit it off immediately. The conversation was easy. We talked a lot about music and her dogs. She pretended to be interested when I told her about my job. And we made a date for her to come over sometime to see my at-home music studio after we had gotten to know each other a little bit.

A few weeks went by, and we finally felt comfortable enough for her to come over. I didn’t tell her that my house has beach access (although I did tell her to bring a bathing suit), so it was a real treat to watch her eyes light up when I drove her home for the first time. While looking out over the beach from the back deck, I told her that maybe, after sunset, we could get in the water, and she laughed.

“After sunset? I’m getting in now!” she said. She was already slipping out of her shoes.

I started panicking. There was no way I could let her see me in my bathing suit, even if I kept a t-shirt on. I tried using every excuse I could think of. That the beach would be too crowded. That I wanted to have dinner first. That it was better to watch the sunset from the deck.

She clocked me immediately.

“You don’t have to be embarrassed,” she said. “You might not believe me when I say this, but I think you’re attractive. Plus, everyone’s got something that they don’t like about themselves.”

She proceeded to pull off the top she had over her bikini, exposing a pretty noticeable scar running from her right shoulder to just under her belly button.

“Car accident,” she shrugged. “For a long time, I would only wear one-pieces. And then, I realized that I felt less sexy in those than having people see the scar under a bikini top. So screw it if people stare. I’m not going to let that keep me from getting in that water.”

It was clear that I was either going to go with her or she was going alone.

And I’m not proud to admit this, reader, but that first time, I let her go alone.

I had a nice cocktail and dinner ready for her when she came walking back up the path to the house. But I still felt bad about it. And ashamed of my own insecurities. I thought for sure she would never answer my calls after that night.

But she did. And we made it a biweekly thing for her to come over, take a dip in the ocean, come inside for dinner, and then we would make some music in the studio.

And, this isn’t some magical story in which I started to love my body for the way it was. Instead, this is a realistic story in which I hired a personal trainer the very next morning after the first time she came to the house. And I started slimming down and putting on muscle and actually caring about what kind of food I was putting in my body.

Exactly six months later, I surprised Mandy by stripping down with her and getting into the ocean. And when we got back up to the house, I surprised her again with tickets to an all-inclusive trip to Brazil. She couldn’t talk me into wearing a Speedo, but hey, maybe I’ll change my mind when we get there.