I’m nearly 70 — it’s time to fulfil my biggest sexual fantasy

This week’s diarist is embracing his new kink (Picture: Getty Images)

Welcome to How I Do It, the series in which we give you a seven-day sneak peek into the sex life of a stranger.

This week we hear from Leopold*, a 69-year-old former English teacher who lives in Spain.

After separating from his partner eight years ago, Leopold has kept his sex life alive with the help of sex workers and masturbation sessions.

And despite almost turning 70, he’s proving it’s never too late to discover a new desire: he wants to find a dominatrix to spank him.

‘I’ve been fascinated by spanking and domination for a long time, but always as the dominant. It suddenly dawned on me that maybe I wanted to be in the submissive role instead,’ he explains.

‘I’ve become obsessed with this fantasy and pleasured myself intensely with it for five days straight, without even the need for Viagra, which was a surprise.

‘I’m ready to begin a new chapter of sexual exploration.’

Without further ado, here’s how Leopold got on this week…

The following sex diary is, as you might imagine, not safe for work.

Monday

You’d think I’d be able to find a woman to give me a good thrashing — if not someone I’ve accidentally irritated, then at least among the professionals. But no.

I’ve been in touch with quite a few sex workers, but many don’t reply, and others want money even to just consider my request for a session.

I haven’t made it easy for myself either, since I’m in Spain but want to be dominated by ‘an English gentlewoman’.

I’ve seen my sex worker, Juanita, fairly regularly over the years. She’s travelling at the moment though, so today, I’m meeting a woman called Susi.

I like to prepare myself, so I shave my penis and balls, and as I have been to the chiropractor in two months, I head to a nail bar nearby for a pedicure.

Tuesday

I have the Viagra ready. I take one an hour before the session, and then one 10 minutes before Susi arrives.

I think she’s leading me into the bedroom, but the language barrier between us becomes apparent as she takes me into the bathroom and tries to position me over the bidet to wash my penis.

I’m a little hurt by this as I’ve already spent time preparing myself — but it’s likely she does this with every client, and she’s not to know I’m already squeaky clean.

Back in the bedroom she starts kissing me but I’m a bit distracted by the constant pinging of messages to her phone. I try to ask her to put it on silent, but instead she pushes me down onto the bed, and places it on the pillow beside me.

I give up and try to concentrate on her enthusiastic caresses before she asks me if I want a blowjob. Juanita will spit on my nether regions a lot when she does this, and it drives me wild with desire — but when I try and ask Susi for the same, she doesn’t understand.

She holds the phone to my mouth and makes me repeat it, translating it so she can understand, which leaves us both laughing.

When we move on to penetrative sex, I let her know that I only really have the stamina for cowgirl, regular or reverse. She does this well, though my encouraging cries of ‘ride, cowgirl, ride’ mean another session with Google translate and a lot more giggling.

All in all, a very pleasant hour for £85, and I will always remember the laughter. Even though it’s a transaction, I do feel a little bit of an emotional connection.

Wednesday

I’m back at my computer looking for someone who will dominate me — I feel sexually and emotionally incomplete without this experience.

I would never look down on another’s consensual kink, but I’m not interested in some fantasies that others are: I wish to avoid being dressed in feminine undergarments or rubber, having my parts locked into a cage, being insulted, or having my balls kicked.

Neither do I get any pleasure from watching other men being dominated, though the occasional well-written description has struck a chord.

For me it’s all about the spanking of the buttocks. I’m comfortable with the spanking part, having received the odd slap from partners and, recently, practiced on myself.

I do worry about the implements or impact tools, as I’ve heard them called, though — I have a vague fear that, after a stroke or two, I’ll leap to my feet screaming my safe word.

I check my emails, and still no response from anyone wishing to fulfil my request.

Thursday

With sex on my mind, I book in a session with Juanita. She provides the girlfriend experience: she greets me with a passionate kiss, takes my hand and leads me to her bedroom.

She tells me to undress and falls to her knees. Then she pushes me onto the bed and undresses herself, as I watch, entranced by her beauty.

We caress and kiss for a while and then she starts to go down on me, until I tell her to turn around so I can return the favour.

Then it’s penetration time. She puts a condom on me (‘XL’, I bet she says that to all the boys) and climbs on top, as she knows my preferences. First it’s regular cowgirl and then I tell her to turn around so that I can watch her magnificent bottom in action.

She won’t accept a proper spanking but says she is is quite happy with the occasional encouraging slap. As for spanking me, she says she is horrified by the thought of causing pain.

The finale is always the same; she goes down on me and I finish, covering my face in case I look especially ugly in the moment.

Friday

I get in touch with Juanita, asking if she’s free again this weekend, but she’s not available.

I know she’s not really my girlfriend but it feels like a rejection, and I wonder if she’s finally had enough of this old man.

I see her Whatsapp status update, which says she will be unavailable for a few days. Not just me then, which is a relief. I rarely think of Juanita and we hardly ever exchange messages apart from when I ask for a session. And yet, for that hour or two, I am completely in love.

Saturday

Still no answer from my prospective doms but looking on X, I find an interesting possibility. A woman offers her bottom for spanking sessions and, while I am particularly keen to find myself across a woman’s lap, I’m still interesting in being the spanker.

So, I get in touch with Greta, and we go about setting some boundaries. She tells me she doesn’t actually touch men, but I can touch her wherever I like.

I say that, at some point, I might want to masturbate and she says that’s fine, but she won’t watch me. Our compromise is I’ll send her to stand against the wall, displaying her reddened bottom while I pleasure myself.

Her response is a smiley emoji along with a devil, which I take to mean we’ve agreed. We set a date three weeks away.

Sunday

Thanks to my new found fantasy I’m feeling, almost constantly, low-key horny. I seem to have lost all sense of guilt and shame about wanting my sexual desires satisfied.

I’ve also been reading about the prostate, and how regular ejaculations are good for it. Apparently, around 21 per month is a healthy number to aim at and, since I can’t afford that number of sex worker sessions, I’m going to have to up my masturbation game.

No porn today; I’ll just run through the script I’ve written in my head for my session with Greta and daydream about, one day, getting that spanking.

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