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My first time booking a male escort: What I learned

This post is from a client in their 50s about their experience booking a male escort for the first time. They give some great advice and tips.

I’d never booked a male escort before

I’m in my 50s, reasonably well-adjusted (most days), and not new to exploring my sexuality. But until recently, I’d never booked a male escort. Call it life, call it hesitation, or maybe I just never felt the urge — until I did. And when that urge hit, I started looking around and landed on this website —www.nzrentboy.com.

Let me say this upfront: it wasn’t about desperation or loneliness. It was curiosity mixed with a pinch of self-care. After years of focusing on work, family, and the usual responsibilities, I wanted to do something just for me. For pleasure, confidence, and, yes, connection.

Step One: Looking around NZ Rent Boys

The first time I clicked onto NZ Rent Boys, I felt a flutter — nervous excitement and just a touch of “what the hell am I doing?” But the website itself put me at ease. Clean layout, photos that actually look real (mostly), and profiles with honest and professional descriptions. Not too many sleazy guys, no annoying pop-ups, just real guys offering real services.

I took my time scrolling. Some were modelesque, others rugged, a few just adorably cheeky. Eventually, I narrowed it down to two: one a tall, tattooed guy who promised a “passionate GFE” (that’s girlfriend experience, ironically), and the other, a charming, boy-next-door type who offered “easy conversation and strong hands.”

I went with the boy-next-door. Let’s call him Leo.

Step Two: Messaging the escort

Messaging Leo was surprisingly easy. I introduced myself, mentioned I was new to this, and asked about his availability. His response was prompt and warm — no pressure, no jargon, just a casual tone that reassured me I wasn’t about to get hustled or judged.

Tip for newbies: Be upfront but polite. Escorts are professionals, not mind-readers. Let them know what you’re looking for, whether it’s a sensual massage, a night out, or a full-on erotic experience. Respect their boundaries, too. If they say no kissing or no travel, don’t push it.

Step Three: Making sure it was safe and fun

Leo offered to host, which worked for me. I wasn’t ready to bring a stranger into my home just yet. Before I confirmed the booking, I did a few safety checks:

I reverse image searched his photos to see if they were stolen stock pics (they weren’t).
I asked about safe sex practices, and he was very clear: condoms always, no exceptions.
I let a close friend know where I was going and when I’d check in afterward. (Yes, it felt like I was a teenager sneaking out to a party, but hey, better safe than sorry.)

When I arrived at Leo’s apartment, he greeted me with a big smile and offered me a drink. I accepted water (gotta stay sharp) and we sat on the couch for a chat. Within 10 minutes, I’d stopped feeling like a bundle of nerves and started feeling like… well, a man enjoying the company of another attractive man.

The main event: Expectations vs reality

I’ll spare the graphic details (I’m still a little shy talking about sex acts), but let’s just say Leo more than met expectations. He was intuitive, attentive, and made me feel like the centre of the universe for the entire hour. Nothing felt rushed. There was laughter, some awkward moments (on my part), and a level of intimacy I didn’t expect from a paid encounter.

One thing that surprised me? The aftercare. Leo didn’t just kick me out the door when we were done. He chatted, offered a shower, and even gave me a hug goodbye. I left his place with a goofy grin and the sneaking suspicion that I’d be back.

My advice for first-timers

If you’re thinking of booking a male escort, here are a few tips from someone who’s crossed that bridge.

Choose wisely. Don’t just go for the hottest guy. Read the profile. Look for someone who seems emotionally intelligent and genuinely enjoys what they do.
Be honest. If you’re nervous, say so. If you have preferences or limits, speak up. Escorts appreciate clear communication.
Respect the boundaries. This isn’t a fantasy where everything goes. Escorts have their own comfort zones just like you.
Don’t expect love but enjoy the intimacy. You’re not buying affection, but you are investing in a connection. And that can be incredibly affirming.
Pay what they ask, and tip if it feels right. These guys are doing emotional and physical labour. Don’t haggle like you’re buying a used car.

Final thoughts on booking a male escort

Booking Leo was one of the most unexpectedly affirming things I’ve done in years. It wasn’t just about sex, it was about feeling seen, touched, and cared for in a way I didn’t realise I’d been missing.

So, if you’re over 50 (or any age, really) and wondering whether this world is still open to you, the answer is a resounding yes. With the right approach and a little confidence, it can be not just a great time but a great experience.

Now, if you’ll excuse me, I’ve got another browse through NZ Rent Boys planned. For research, of course.

R18