Sex Column: Sex With A Sugar Daddy

A beautiful friend of mine, who’s now happily married and settled down, shared details with me of her mischievous – some people might use another word – younger years, when she decided to navigate the legally grey terrain of a ‘mutually beneficial relationship’.

Julie came from an upper-middle-class family, had a college degree, and learned early on that her beauty and sexuality could be used as a commodity to fund her free-wheelin’, bohemian lifestyle. Some would see it as a form of prostitution. She didn’t care.
“I was still in college and fresh out of a rough break-up with my ex,” Julie recalls, “when I started navigating Craigslists’ Casual Sex encounters”.
CL is an American, consumer ‘want ad style’ publication.
“We didn’t have things like Tinder apps at the time,” she says. “It wasn’t so much that I was going to find a stranger online to have sex with, but it aroused me from my boredom and helped to distract me between finals, while I mourned the end of the relationship. Anyhow, I saw an ad that caught my eye, with ‘Seeking Mutually Beneficial Relationship’ in the title. It was an older gentleman, seeking a younger, college-age woman for a sexual relationship in exchange for financial support. Sounded fine to me since I wasn’t quite ready to start dating again – but I felt that I could have the physical companionship I was craving in a strictly sexual relationship.”

Fully Erect
What was the first meeting like?
“Trevor – that was the name he gave himself – arranged for us to have dinner first at a Thai restaurant,” she remembers. “That way we could scope each other out, in case the other turned out to be an American Psycho type. When I saw him, there was nothing about him that stood out to me. He looked normal for a 40-something-year-old man, with glasses, sandy hair, and a buttoned up shirt. He seemed sweet and very transparent in what he sought – so, I agreed to go over to his condo just a few blocks away.

“We agreed on a $1,500 per date arrangement – it was a random sum I threw out for the hell of it, and he accepted. It was intoxicating to win my first negotiation this way, and I learned that women hold so much power sexually. I would go on to have many more Sugar Daddy relationships in my twenties. The thing is that this was the one area where I held true negotiating prowess, because what I was selling was not something these rich and powerful men could buy just anywhere, and the allure evened out the arena between us.

“True, they could go to any prostitute to buy sex,” she adds, “but that was not my ‘brand’…It was like Gucci versus K-Mart.” She smiled at me, and I caught a glimpse of her allure. It was obvious what was in it for the men. But what about her? Surely there were risks? Was she scared at all?
“No, I wasn’t scared and I probably should have been,” she reflects. “These things can end up becoming murderous, but I’ve always had – or felt I had – a profound sixth sense of near-psychic sensitivity to people and I just knew I was safe. When we got to his condo, it was quite luxurious. He poured me a glass of red wine, and we sat in the living room finishing it, then walked upstairs to his bedroom. As we passed his office, I spied several Emmy awards sitting on the shelf.
“We got to his bed and he undressed me reverently. You could tell this man loved women, but also truly respected them in form and essence. He was a fine connoisseur of women. Or that’s certainly what he made me feel at the time. As I lay naked on his bed, he began to massage my body, relaxing me wholly. It was nice to be pampered this way and it was very different to most of the experiences I’d had with younger men, who were all about getting themselves off.
“He then put his fingers inside, gently transitioning the massage into erotic foreplay. My wetness was what turned him on, and until I was very wet and ready, he would not enter me. He then went down on me for what seemed like hours: time stopped because the pleasurable lolls of his tongue and mouth only wanted to serve me – without reference to his own needs. When I looked up, I saw his penis was fully erect. It was handsome: tall, sturdy, and full of girth in a proud, standing shape; in a way that was unexpected, like his generous lovemaking. When he slowly stretched it into me, my pussy was ready to receive him fully and we had a wonderful fuck.
“Afterward, we got dressed and walked down to his office where he took his cheque-book out. It was weird. At that moment, he looked just like my own dad, writing me cheques when I needed extra support or rent money. I found out later that he had two daughters close to my own age, and that he was an Emmy Award-winning producer.”

Warning Signs

Obviously you can see this as a form of exploitation. It may even be that. But that’s not what Julie experienced. It is certainly not the way she describes it. “His privilege gave him an air of aristocracy without the arrogance of the ‘nouveau riche’,” she says, “and it was his Old Hollywood pedigree, I guess, that made him philanthropic, even when it came to the blurred, and obviously transactional relationship of a benefactor arrangement such as ours.”
One part of me thinks: damn, I should’ve tried out this line of work in college myself! Another wonders was my friend just lucky? But Julie’s experience does say some fascinating things about the nature of sex and relationships that are too often blurred, or ignored completely. The first is that women make decisions like this of their own free will. She has no desire to blame the man. She knew what she was doing. There isn’t the slightest question in her mind about that.
The second is that love takes many forms. And sometimes, it can be found, in a genuine way, between people who have no thought of a romantic future together. Indeed it – real love – can be there in the very recognition of the individuals’ separateness. Equally, sex can be good – it can even be great – without any requirement to be in the service of a long-term relationship that’s aimed at either ‘settling down’ or marriage.

Some people spend their lives erecting warning signs and lists of things that are ‘wrong’ in relation to sex. Not Julie. As for me, I tend to want to embrace life, love and sex, in all of its variety and diversity. As long as it is between consenting adults, as the song says, whatever gets you through the night...