Sugar Baby Stories: Caitlin, aka Plain Jane

sugar baby stories series

Tell us about yourself: who are you?

Well, that’s a big question, one that I can’t answer at the moment. But I can tell you what I’m not – the typical sugar baby.

Or at least, the media’s picture of the typical sugar baby. For starters, I’m far from picture perfect pretty. I’m also a bit older than the average sugar babe. And I spend most of my days in yoga pants and sneakers – and not the sexy kind, either.

If you saw me out on the street, you’d never guess that I was a sugar baby. I love that feeling of being out with a sugar daddy and no one being none the wiser about the kind of relationship we have. It’s like the feeling of wearing red hot lingerie underneath a pair of baggy sweats – a delicious secret.

What were your goals in starting the sugar journey?

Time. Free time. MY time. After I finished my graduate degree, I realized I had no goddamn clue what I wanted to do with my life. But I definitely wanted the time and space to be able to explore my options.

Taking a full-time job would’ve paid my bills but it would not have granted me the leisure of time to try out new things, experiment and find out what I wanted to do with my life.

A sugar daddy, on the other hand, could have me covered financially and I’d have the free time to be able to “find myself.” Win-win, I thought.

What do you wish you’d known when you were first starting out?

Chemistry is…everything. I didn’t know any real sugar babies when I first became interested in this so I believed the media representation of what a sugar baby was supposed to be like, to look like, etc.

I lost some self-confidence because of that, thinking that I was probably not sexy enough or pretty enough to stand out to potential sugar daddies.

Well, it turned out that some sugar daddies really were not interested in me but some WERE and that’s all that really matters, isn’t it? And it didn’t have to do with my looks or how I dressed as much as our dynamic. The best sugar relationships I’ve had are the ones where we became friends and confidantes to each other.

I wish I’d known that sugar relationships are a lot like regular relationships is that emotional connection matters: find a sugar daddy who actually cares about you as a person and one you actually care about.

Where and how did you meet your sugar daddy? If online, which site?

I’ve had several over the years, but I met my longest sugar relationship through I sign up for all the big sugar dating sites – and even tried Craigslist – and was reluctant to shell out the cash for SugarDaddie, but it turned out to be worth it.

I’d say each of the main sugar dating sites have a different feel to them and tend to attract different people. For starters, don’t do Craigslist – I’ve never had even one decent sugar date from posting an ad there. The first and foremost assumption of any “sugar daddies” on that site is that you’re okay with pay-for-play. They’re basically johns posing as sugar daddies.

Anyway, SugarDaddyForMe seemed to have a lot of on-the-fly sugar daddies, young men who liked the concept of having a beautiful sugar baby and were ready to try it out.

SeekingArrangement had a more professional feel to it and the men on there seemed…polished? But also a little less reachable to me. was my “Goldilocks,” if you will – I met many intellectual types on there who were interested in taking it slower, getting to know each other and finding a really great, mutually very beneficial sugar relationship that worked for all parties.

Do you have any profile or online dating tips for aspiring sugar babies?

Yes, definitely: tailor your messages and responses to the sugar daddy’s personality and interests. NO sending stock messages! Sugar daddies are busy and there are tons of sugar babes trying to get their attention so make your message stand out.

For example, I was trying to get a certain POT’s attention – his profile stuck out to me ’cause it was smart and witty, which meant that he values that enough to take the time to craft such a profile. So I wrote to him with a Marx brother’s quote in the subject line (I guessed he’d get the reference, based on his profile), playing off something he’d said in his profile. He responded back in a few hours.

Always, always play to the POT’s interests – not yours.

What’s your favorite thing about being a sugar baby?

The TIME. The free time and the money to be able to make use of that time. I’ve had incredible experiences since sugar dating that I never would’ve found the time, money, or imagination to do if I’d been stuck at a 9 to 5 every month.

And it’s not just the experiences – one amazing benefit of being a sugar baby is that you get paid to get access to some really smart, successful people. Seriously, you know that these sugar daddies’ time is worth a lot, right?

IMHO, every sugar baby should be taking advantage of what she can learn from her sugar daddy – financial advice, business advice, his opinions on the world, etc. – ask and learn. It’s probably the most valuable thing you’ll get out of a sugar relationship. Check out the pros and cons of being a sugar baby!

How do you keep your sugar relationship spicy/fun/interesting?

After several successful sugar relationship, I’ve realized that the dynamic of a sugar relationship naturally changes over time – just like in actual relationships. But you’ve always got to maintain your sugar standards!

In the beginning 3 to 6 months, it’s easy to be your best behaved, most pleasant, wonderful sugar baby self but as the relationship progresses, you get more used to each other and it’s easy to stop making an effort. This is where sugar relationships and even regular relationships start to unravel.

I’ve been down that road in the beginning, so I remind myself to stay on my toes all the time. This means I make a lot of effort to be totally present, appreciative and happy when I’m with my sugar daddy. It’s a practice because it’s just so easy to get sloppy but remembering that it’s a sugar relationship – you get benefits and so does he! – helps on most days.

What advice would you give aspiring sugar babies?

Not to get too serious on you, but seriously – save and invest the money you make while sugar baby-ing. Instead of spending it on shopping sprees and bigger, better living, continue to live simply and save and invest your funds so you can be your own “sugar daddy” one day.

This is not just good for you, but your sugar daddy will respect that and be willing to help you out even more. So don’t just “get yours” – save and invest your sugar!

Having a backup fund also gives you the leverage to walk away from crappy arrangements. I actually agreed to a sugar relationship with a sugar daddy who I’d spoken to extensively before entering into a relationship with.

I thought he was nice and everything would go hunky dory until the first date of our arrangement – we were driving to dinner and I was talking about something when he suddenly looked over at me and told me to “shut up now.”

It was so unexpectedly disrespectful, I fought back tears. And then anger. I mean – I am not some robot or slave and this man clearly had no idea how to treat a woman. Thankfully, I had enough in savings to not even have to think twice about dismissing this rude man.

Please, sugar babies, don’t put up with rudeness and disrespect. It’s not worth the emotional damage – ever. Having your own emergency stash of savings will help you walk away from unwanted situations so always be saving!

This post is part of our Real Sugar Baby Stories series, written by sugar babies, for sugar babies. If you want to share your own experiences with the sugar world – write for us!

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