My Experience With Happy Ending Massages At 50+

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26-07-2025

Way back near the beginning of pandemic, I had a real-life Good Luck to You, Leo Grande experience.
If you're not familiar with the movie (now streaming on Hulu), a retired widow (Emma Thompson) hires a fine-ass sex worker (Daryl McCormack) to find some sexual adventure. (Spoiler: Adventure is found.)
In my case, there was no green-eyed Leo Grande. However, I did have two (2!) people working over my middle-aged body. Also, they weren't official 'sex workers,' though it did involve both sex and work.
I was getting a 'hands-on bodywork session,' basically a massage with a (possibly) happy ending. Oh, it was all on the up and up. It was through an organization, let's call it Yonis R Us (YRU), that hosts retreats in glamorous locales where women of all ages (seriously, ALL, like up to extremely senior citizen) learn to connect with their bodies, their sexuality and their desires.
And yeah, a happy ending might be had, but the bodywork sessions were about more than that. It was about allowing yourself to accept pleasure and feel sexual without any of the body image/performative/goal-oriented pressures of a lot of hetero sex.
Getting rid of that last bit was going to be a trick for me. I enjoy spending my leisure time worrying about things like that new spot on my leg (fatal????), people who don't text back immediately (dead???) and the like. My monkey mind doesn't just chatter away during my rare attempts at meditation ― mine is more howler monkey, always on duty, hyper-vigilant and screeching from the treetops, alerting me to a constant stream of imaginary peril.
To be honest, I was secretly looking for a Magic Vagina Whisperer, someone who would force me to chill the F out, know what I wanted even before I knew it, and could play my body like a piano, or whatever musical instrument is the equivalent of my body (Bagpipes? Theremin?).
When Nanette*, the founder of Yonis, messaged me one day and offered me a private session that night, gratis, I was immediately like, 'Yes, please!' It was to date, the best media perk I've gotten, and I am a person who recently received a huge box of weed products hand-delivered to my door.
About four seconds later, I panicked. The letting-strangers-touch-alllllll-the-naughty-bits wasn't the issue. I've interviewed several sex workers and came away convinced that sex work is an important helping position. Providing loving sexual touch to people who aren't getting it, for whatever reason, is a gift. I had no moral quandaries. Viva getting touched by a kindly, trained stranger/specialist!
But on that particular day, I was not feeling super fuckable. I already had a full-on pandemic body going on, even though we were just barely into it. Underneath my Bao -like belly, I was sporting a bush with the aesthetics of an abandoned parking lot.
As Emma Thompson told Vogue about the extremely last-minute preparations for her role in Good Luck to You, Leo Grande, 'I couldn't go off to a health spa in anticipation of forthcoming nudity.'
Nor could I, Emma. I couldn't lose the belly in one day, and in a flash of liberation, I decided I would leave the bush in 'as is' condition. I was gonna own this 'forthcoming nudity,' goddammit. The idea was strangely empowering. 'Screw it!' I thought. 'This is my body. Behold!'
That night I pulled up to a charming little house tucked down a shady lane somewhere by San Diego. I was greeted at the door by Nanette, who is short, curvy and warm, like a sexy fairy godmother. She introduced her associate, Rod Steele,* who is blonde, muscled and pretty much an ideal specimen of manhood, as well as being a lovely, gentle person.
There was a spacious living room and a large wooden dining table laden with snacks. I picked at the spread while we had easy talk about…something? Finally, they asked me to go into the bedroom, disrobe, and get up on a table similar to a massage table. I draped a sheet over myself and waited.
When they came in, they spoke to me gently and started giving me a massage. If you find yourself in a situation where two people want to give you a massage, I'd recommend you take them up on it at once. It was pretty great.
I closed my eyes as they introduced elements of sensation play, always asking permission first. There were scarves draped up my thighs, a little wheel toy with pokey things ― the idea was to stay in the moment and really focus on the sensations.
Somebody eventually started touching me where the bathing suit covers. There were some consensual flicks of a flogger and the introduction of a butt plug. It's odd that I can't remember the specifics of who was touching where, otherwise I could give you a play-by-play, like 'Bishop to e5.'
What does stand out is that it was dawning on me that I wasn't even close to having an orgasm, and I (ridiculously, I know this!) felt like I should ― like it would be polite to do so. And it felt absurd that it wasn't happening. I was being stroked and lavishly feted by two gorgeous, sexy, and attentive people. But I was lying there wondering if their hands were getting sore, and they regretted doing this for free.
So there I was: naked, the stimulation increasingly amping up, and still not having an orgasm.
Eventually (two minutes? 700 years?) they brought out the big guns, the hallowed Magic Wand. If you're not familiar, the Wand is a giant vibrator that's pretty much a jackhammer for the lady parts. If there ever was a vibrator that could easily be converted to gas power (rip cord and all), it would be the Wand.
They applied the Wand, but my body would not succumb to it. I felt my monkey mind cockblocking the insistent ministrations of my electric lover. 'Shit, it's still not happening!' I thought, which for the record, is pretty low on the list of arousing thoughts.
Then it dawned on me. I thought about my best sex ever and how raw chemistry goes a hell of a long way towards arousal. Yes, the simple biological manipulation of body parts is a huge part of sex, but it's just one part of a complex mix of lust chemicals, scents, the almost divine touch of someone who really does it for you and the particular appeal of a partner's jawline/chest/thigh/thick dick/whatever.
In this case, all manner of diligent rubbing wasn't gonna be enough. It's the same reason a glory hole wouldn't appeal to me. I'd need some backstory.
Here, I couldn't just lie down on the massage table thing, spread my legs, and get lost in it.
In discussing the 'problems' of sex in How to Think More About Sex, the delightful School of Life co-founder Alain de Botton writes, 'Great sex, like happiness more generally, may be the precious and sublime exception. During our most fortunate encounters, it is rare for us to appreciate how privileged we are. It is only as we get older, and look back repeatedly and nostalgically to a few erotic episodes, that we start to realize with what stinginess nature extends her gifts to us — and therefore what an extraordinary and rare achievement of biology, psychology and timing satisfying sex really is.'
But I digress. Through all this, the Wand was determinedly buzzing away, perhaps puzzled, not understanding why I was resisting its charms. I didn't know what to do, so finally I mentally pulled up the images of my favorite porn. If you must know it's the one with two college guys who, against their supposed straightness, get too turned on and simply must bone each other immediately.
Eventually, less being swept away by inevitability and more 'I will make this happen,' ala Annette Bening, 'I will sell this house today!' in American Beauty, I had the orgasm. Check. Not huge, but there. Hey, way to ruin goalless pleasure with a goal, self!
Once the 'sex' part was done, we moved back out to the living room. I sat on a couch, and Nanette and Rod settled in on each side. They snuggled in close and handed me an exceptionally good popsicle. We talked about what had gone down and how it was for me. Rod suggested I give the plug another try sometime. I had another popsicle (this is unrelated). It was A+ aftercare.
In the end, I still completely support this kind of work. If you can lie back and enjoy being attended to by two eager pretend lovers, get yer butt on up on that table. (Statistically, it's likely that you'd dig it: Multipartner sex is the most common fantasy, according to Justin Lehmiller's Tell Me What You Want.)
For me and my howler monkey mind though, the most thorough fuck of the night was the mind fuck I gave myself. It wasn't ideal, but lessons were learned. Sex with another person who hotly desires you as much as you desire them is a rare and beautiful thing. This was not it. But it didn't need to be that. It occupied a different space.
In this space, you can be sexual without worrying about pleasing another (or, like me, you can worry about it anyway) and that feels important. You can go to this place, go really deep sexually and emotionally with two other people, then be on your merry way, with no emotional reverb. And you might even get some popsicles out of the deal.