Musings

This week’s mini blog series on my sex work experiences is coming to an end. For this instalment, I’ve partnered with Rachaels London Escorts to tell you a story I’ve never really opened up about in detail before: that time I was a sugar baby for a little while.

I used to dream of having a sugar daddy who would buy me lingerie and handbags and luxury sex toys. I mean, who hasn’t had some version of this fantasy at one time or another? Though I played around on SeekingArrangement (the best-known “sugar dating” site) and mentally mapped out how I’d spend a generous benefactor’s money, I didn’t think I’d ever actually have a sugar daddy; men with the means and desire for this type of relationship are usually inundated with fit blonde conventional beauties in their early twenties, and I am… none of those things, so it seemed like a long shot.

However, one day in 2017, I got a cordial email from a man whose name I didn’t recognize. He introduced himself, heaped on compliments about my blog and podcast, and asked if I’d be open to a (paid) phone-chat session with him sometime, as the phone “happened to be a favorite play medium” of his. He attached two photos of himself, serious black-and-white formal portraits in which he smouldered at the camera in a suit. I was intrigued.

I was used to charging in 15- or 30-minute increments for such services, so I was surprised when he wanted to book a whole hour. “Please let me know how to render the honorarium and I’ll handle immediately in good faith,” he wrote – music to the ears of someone who so often has to harangue potential clients to finally, reluctantly pay. We agreed on a price and a day and time, and he sent the money promptly, in advance. What a dream.

He opened our first phone call by telling me he planned to approach it as a “first date” of sorts – i.e. he wanted us to chat and get to know each other, hopefully as part of an ongoing connection, not just a one-off phone-sex encounter. That first night, chatting is all we did: he complimented me and my work profusely, told me about his career and interests, and explained his own journey with non-monogamy and kink, which had led him to me. He had a wife, but they both dated and fucked other people with each other’s full knowledge; he, however, preferred to pay dates rather than seek them out organically for free, because he said it simplified the process. He was a highly busy small-business owner and didn’t have the spare time and energy to trawl Tinder or OkCupid, besides which, those sites rarely connected him with the open-minded, kinky, smart women he was seeking. Hence paying me by the hour for a phone date.

We enjoyed our conversation so much that when the hour was up, he asked if I had time to stay for another – with proper compensation, of course. When I said yes, the amount landed in my account almost immediately, and we carried on chatting about our lives. I was amazed that I’d just made the equivalent of 20-30 hours of minimum-wage work for a two-hour phone call that hadn’t even felt like work. He was eloquent and charming and I’d enjoyed our chat. I’d basically been paid to be complimented and flirted with for an evening. Pretty ideal.

I took myself out for a fancy solo dinner the next night, spending some of his money on pasta and cocktails I worked my way through while leisurely reading a book. The decadence made me feel guilty. This wasn’t my life. But maybe it could be.

We continued having these get-to-know-ya phone chats on and off for a few weeks. I learned that he lived in New York, that he had followed me and my work for quite some time, and that some soul-searching on the topic of kink had brought him to the realization that he was a daddy dom. That role spoke to him because he liked guiding the action of scenes and having consensual control over sexual partners, sure, but also because he longed to give guidance, structure, and wisdom outside of the bedroom. I warned him that I wasn’t comfortable calling anyone “daddy” just yet, having recently had my heart broken by my first daddy dom, but I could open myself up to a new dom by another name, perhaps.

We had phone sex for the first time late one night, once he’d established I wanted it, and had (of course) paid for my time. It was long and slow and lovely. I felt guilty taking my time to come as I listened to him spin sentences about giving my clit and labia lots of attention, but he assured me repeatedly that he liked the arousal process, he liked listening to me getting closer and closer to orgasm, and he intended to pay me for any extra time we spent because he wanted to hear me come. He was true to his word.

Sometime after that, he floated an idea he’d been pondering this entire time but hadn’t felt brave enough to bring up yet. He wanted to work out an “arrangement”: he would pay me an agreed-upon monthly allowance so we could talk and text and email organically as our schedules allowed, in lieu of paying by the hour to talk only at certain times. He offered, too, to cover my airfare for all trips I took to and from New York while we were “a thing,” even if I only saw him once during the entire trip. This especially excited me, as my best friend lives there and so did a new person I was flirting with and potentially wanted to date. I’d been wishing I could afford more NYC trips, and now here was a person offering to fly me there once every month or two. How perfect!

The arrangement began; the money flowed in. I bought a Coach handbag and a microwave. I stared at my bank balance sometimes, half-bewildered, half-turned on. I felt better about my financial situation than I have ever felt in my life.

We started planning our first in-person date, slated for mid-December. Pasta, musical theatre, a night in a hotel. I mentioned casually in passing that I’d also be seeing my new beau while there, and I heard my sugar daddy’s voice waver a bit. He told me that, despite having been non-monogamous for years, he still struggled with jealousy occasionally – and this situation triggered it especially, because the other person was “right in [his] own back yard.” I was confused, because he’d known going into this that I had other partners, but I told him I was sure he could work through those feelings and that I could provide some poly-newbie resources if need be.

However, just 10 days before I was scheduled to fly down to see him, he called me and confessed that his jealousy had gotten the better of him. He wanted to “bow out” of our arrangement. He’d thought he could handle me dating another New Yorker, but he couldn’t. I was disappointed – not just because of the money, and not just because it was another rejection in a year that had been full of rejections for me, but also because I had grown genuinely fond of this man. Hearing his supportive voice over the phone had become a comfortingly dependable tradition, and I was sad to lose that. I went over to another partner’s house later that day for a scheduled date and he held me and consoled me and got me high and fucked me well. (Good poly is so good.)

I’m still sad from time to time about the loss of that arrangement. It fulfilled so many of my core desires: to be cared for, and appreciated, and listened to, and pleasured, and spoiled. It topped up my bank account while also topping up my self-worth and my sense of being supported by someone who wanted the best for me.

But there is also joy to be found in making my own money, treating myself to nice things when I can, and developing relationships with people who aren’t threatened by my other potential paramours. I like having people I can depend on, and I also like feeling independent to some extent. This foray into sugar dating taught me more about my ideal balance in between.

Thanks to Rachaels London Escorts for sponsoring this post! They’re open from 10AM to 1AM (amazing!) and are available for a range of booking opportunities, such as dates, massages, parties, and naughty nights in hotels.