Lee, 23, Sociology Student
“I hired an escort to help me lose my virginity”
I dated a boy at 14, but when we got going physically, things got to a point where I wanted to stop but he didn’t. It got ugly. I was raised by a single mum who taught me, “Don’t ever take shit. If you are uncomfortable, leave.” So I did, but from then on, it was very difficult to imagine being intimate with someone else. I would not go near men because I couldn’t get past that block of thinking that they can violate your trust. As I reached 21, I realised that sex was something I did want to experience, and I shouldn’t let that one bad memory affect everything else I do.
I didn’t want some random drunk guy in a bar who may not be kind or patient, but I also wasn’t ready to deal with all the elements of a relationship – commitment, time, risk and emotional investment – so I started researching male escorts. I decided to go for quality over quantity and looked up the most expensive man for hire. Jake Ryan’s body shots were over-the-top, almost too much for me to take in! I read his bio and testimonials, which told me everything I wanted to hear and nudged me over the line – they were understanding, warm, human. I was scared to meet him though. I hadn’t spent one-on-one time with a straight man, other than friends, for six years, yet alone an escort with a sixpack. But when I met Jake over dinner I thought, “Damn girl, I have won the lottery.”
I had special lingerie and three outfits sorted for the big day, and booked Jake for two hours. Although I felt dizzy in the lift up to his apartment, from the moment I got in there he made me feel welcome and comfortable. About 30 minutes later we were lying on the bed and started making out. I have quite severe generalised anxiety, so it was good to have all that just go away. I said, “I think it’s going to be better if you take the lead and tell me what to do.”
My biggest concern was that I wouldn’t be able to go through with getting naked in front of someone, but my worries evaporated as Jake took charge.
I was also concerned about how I would feel seeing a penis in real life, but I found Jake’s really attractive. I had asked to learn how to give a BJ,
so we started with that. I chose to go ahead and make love. My body was tingling and felt like it was going to explode with pent-up sexual energy.
He started at my feet and worked up my legs, prepping me so that I got worked up embarrassingly quickly. It was really good; I actually came twice. I did not want to see my own body, I am so self-conscious, and considered being blindfolded, but I became so turned on by him I wanted to see everything.
The experience was better than I could have ever imagined and I felt an enormous psychological relief. Using an escort had meant that I was safe, in control and free to explore without judgement.
I put the envelope of cash on the table, which felt somehow separate from our affectionate encounter. I could imagine someone who wasn’t fully mentally prepared totally falling in love with Jake, and that could get very difficult. But I was happy and prepared for the financial arrangement.
I’m a uni student, so it took a long time to save the money to hire Jake. But I think it’s absolutely amazing that women are able to take their own pleasure and confidence into their own hands. I’m so glad I did.
Emma, 42, Entrepreneur
“We hired escorts to enhance our marriage”
My husband Tom and I love each other to pieces. We met online, the fireworks hit and we moved in together within two weeks of our first date. We blended our four kids from previous marriages, then had our baby together. But as an aside to our gorgeous family, Tom totally understood when I said I wanted to step out of being a stereotypical mum and reclaim some of my life.
Once, when we were on holiday, another couple cruised us. We didn’t act on it, but it inspired us to do something outrageous and try another couple – on our own terms – back home. We could hire two professionals so it wouldn’t get messy, but we were clear that we wanted sexual exploration with escorts to
enhance, not wreck, what we have.
We discussed the double-booking at length. We wanted to know that we would come out of this unscathed – that is the scariest thing. Tom is the love of my life, so nothing was going to stuff that up.
I was super nervous about it. I usually need a really strong connection for sex, then there was the weirdness of seeing Tom flick through the photo gallery of tight-assed 20-year-old female escorts to make his choice. As risk management before the first booking, we assessed our individual strengths and weaknesses and promised to always be honest
about what we were feeling.
We both lost weight and got fit to feel better going into that sexual space, and agreed that we would stay in one room – everything out in the open –
so that no-one felt left out. It was an emotional journey and challenge, and it quickly went from fantasy to reality when we arrived at Jake Ryan’s working apartment.
Jake kicked things off with champagne and spin the bottle: everyone’s clothes came off within five seconds of being in the room. When the clock is ticking at $750 an hour for a double booking, you kind of have to jump in.
All our rules went out the window at a certain point. All the protocol – “no deep kissing, no oral sex” – gets forgotten as you look over and see your husband receiving a blow job. We did end up in separate rooms that first time, because it got so distracting to see and hear your partner with someone else that
you can’t concentrate on your own experience with a new person.
There was a massive relief after the first double-booking: a huge victory. We made it. We were so amped up that we were clawing each other back in our own hotel room afterwards, [and going] let’s do it again!
The journey has inspired Tom and I to get fitter and has taken us to a whole new level of intimacy. It has deepened our trust, as we supported and respected each other through the whole process. As a couple, you wouldn’t go near this unless you have great communication skills, can allow each other to express your true feelings and make a sacred pact to put each other first – no matter what.
This article originally appeared in the February 2020 issue of marie claire.