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An orgasm from a stranger had been my ultimate fantasy, but the reality was very different.
W hat’s your ultimate sexual fantasy ? Most of us have one, but what do you do after you’ve lived it out for real? This was the question I was confronted with after what was an innocent holiday massage ended became a sexual happy ending massage ... and ended in an unexpected orgasm .
A happy ending massage - or sexual massage - was something I’d always fantasised about, but I never dreamed it would actually happen. So, when I heard about the hotel spa services while on holiday in Cuba I booked my appointment without any expectations.
At the appointed time, I turned up at the ‘spa’ – a gauzy white tent on the hotel beach – and was assigned a male massage therapist. I wasn’t at all uncomfortable with that.
At first, the massage was utterly innocent. He was friendly but professional; not chatty or personal. He completely avoided my chest and bum (not true of all masseurs, I can assure you), and rubbed my body without any… lingering.
By the end, I was lying on my back while he massaged my legs and thighs, which is perfectly normal, by the way. But, as I’ve always found massage a sensual experience, I can’t pretend my body wasn’t responding.
When his hands stilled on my inner thighs, I thought it was part of the massage. It didn’t seem strange at all. He then began to apply pressure to my inner thighs, moving closer and closer inwards, until he brushed my bikini bottoms. It was like a jolt of static, and I knew something else was afoot.
It was like a jolt of static, and I knew something else was afoot
I couldn’t believe that my ultimate sexual fantasy was being played out. I’ve never been so turned on in my life, but I assumed he’d stop there. And he did, until I (almost unconsciously) began to shift my hips and tense upwards. He moved my bikini to one side, spreading my legs apart with one hand. I was enthralled, and had no intention of stopping him. It was an almost out-of-body experience.
Briefly, I began to grow nervous about someone walking in (we were in a tent, after all). But as he stroked my clit in sensuous, circular movements, I decided I didn’t care. Once he’d slowly and deliberately slid his fingers inside me, I couldn’t even think about anything else at all. I’ve never come so quickly, quietly or effortlessly in my life. Which was lucky, as it turned out, because another massage therapist walked in right afterwards. Then it was all business.
He used the towel to wipe oil from my body efficiently, while I lay blushing and giggling with my eyes closed. He turned, allowing me to dress, as if it had just been an ordinary massage. I didn’t make any eye contact at all as I settled the bill, and gave him a huge tip which is expected in Cuba. He asked my name, and told me to come again the next day. I smiled, knowing I wouldn’t.
At first, I was relieved she hadn’t walked in a few seconds earlier. That was until it dawned on me she probably knew exactly what was going on, and likely peeked through the tent to see when I was done. The thought made me feel sick with embarrassment. Then the doubts began to creep in. Had I exploited him?
There are a lot of male sex workers in Cuba, so I had to wonder if he was one. He certainly didn’t risk his job and livelihood because he was overwhelmed by passion for me. Slowly, I grew uncomfortable with how expert he was. This was a practised move, clearly something he did often, and did well. But he didn’t do it because he wanted me. Did he think he had to perform this for monetary purposes? Whether by experience or coercion, did he think it was his job to offer?
These things don’t exist in a vacuum. Just look at the blurred lines between the sex trade and massage industry of Southeast Asia. I’m strongly anti-exploitation, and the idea of one of my male friends allowing a woman to give them a ‘happy ending’ would horrify me. Many of those women are victims of human trafficking, sold into the sex trade as slaves – sometimes underage – or were drawn into the industry by the twin demons of poverty and opportunity.
These things don’t exist in a vacuum
I would argue that if you really respected them, you wouldn’t allow them to pleasure you for money in countries where the sex trade is so notoriously shady.
Had he exploited me ? Was I a victim of assault? My mind and body were saying yes all the way through, but I never consented verbally. What right did he think he had to touch me like this in a professional setting? Was I a bad feminist? I’m 100% pro-sex positivity and mutual enjoyment, and this experience didn’t seem to sit right with that. If he respected me as an equal, wouldn’t he have asked? Was I unintentionally “asking for it”? I was more than a little confused.
I told my best friends in confidence, but was embarrassed. They were supportive, but shocked. It was easier when he was just a disembodied hand in my fantasy. Sadly, fulfilling a ‘stranger’ sexual fantasy means actually having to confront the stranger, and the context. And I learned a fantasy is never the same in real life as it is in your head, precisely because it’s real life.
“After #MeToo we’re probably all much more aware of our potential positions as victims - and perpetrators - in non-consensual sexual encounters,” says Dr Meg-John Barker, a sex therapist who writes on the psychology of sexual activity. “This experience is a challenging one indeed, as it involves confronting both those possibilities.”
They recommended I take some time to sit with the feelings of being in both of those positions, and getting support if I found that difficult.
“Your story also highlights important questions about power and consent,” they told me. “As the tourist in Cuba, you were in a position of power over the masseur, especially given he could have lost his job. But as the professional in the encounter - and a man - he was certainly in a position of power over you.”
I would strongly suggest insisting on a more upfront conversation
Dr Barker, who also wrote Enjoy Sex (How, When and IF You Want To ) and hosts a new podcast “Meg-John and Justin” , explains the vital thing with consent is that everyone involved is able to give an enthusiastic ‘yes’ to what unfolds between them. They must be able to know for sure that nobody’s feeling pressured by power dynamics, or because it would feel awkward stopping things once they’ve started.
“Even if you find an encounter pleasurable - or orgasm from it - if that wasn’t there, it wasn’t consensual,” they add. “That’s not at all to say you can’t have hot encounters with strangers, or that consent can’t be communicated in non-verbal ways. But in future, I would strongly suggest insisting on a more upfront conversation, and stopping things, if you can, if any part of you was feeling as unsure or nervous.”
Dr Barker’s words helped me articulate and make sense of my confusion, but ultimately, it didn’t resolve the experience in my head. Of course, the further into the past it gets, the less I regret it – it’s certainly forced me to think much more seriously about sensitive issues of power and consent on a personal, rather than theoretical, level.
A hands-on experience, certainly. But I would advise anyone thinking of acting out a stranger fantasy, of any kind, to consider Dr Barker’s advice very carefully: an upfront and frank conversation with clearly communicated consent on both sides might not seem sexy in the moment, but you’ll appreciate it the morning after.
This article was originally published in 2018 and has been updated.

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~ refresh yourself, body and mind ~ Victoria, BC ~
Your time with me includes a happy ending – but I am not a full service provider so I won’t be using anything except my hands
Just as I will only be using my hands, I ask that you only use your hands as well. So, please, no oral or kissing

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