After scores of lackluster dates and a ten-year dry spell, this independent Amazon in her 40s decided to take her love life into her own hands – or rather, turn herself over to someone else’s.
This story dispels three persistent myths. The first is that a desirable woman is spoiled for perfect sexual offers just because she has a phone full of unrequested dick pics. The second is that women will encounter judgment for choosing to pay for the perfect encounter. And most important, the one drilled into all the “good girls” from childhood, that we have to know and be in love with a man to open ourselves up to him sexually. The other hotel guests soon heard differently…
Every few years, I decide to give the ‘dating game’ a go and resort to the newest commercialised, and often humiliating, matchmaking app. At the end of my experimental periods, I am still single, unwittingly the owner of a card deck worth of ‘dick pics,’ and armed with a bucket load of hilarious dating encounters that have my married friends in stitches.
Much like these morsels:
- He was half an hour late to our first date because it was the first Sunday he’d had off in three months, and he wanted to sleep in. His mum forgot to wake him up. He was in his late 30s.
- His mates sat at a table not far from ours for the duration of our first date.
- Although he was a web page designer by day, his true passion was designing bondage apparatus in his garage at night. He wanted to strap my breasts into his newest creation (picture two 15cm planks of thick wood with airline-grade tie-down straps nailed to them).
- He was a 55-year-old man with braces and an inability to talk about anything except roof construction. So, I asked if he had any children. He showed me a photo of his 29-year-old son, and I went into instant cougar mode. There was obviously attraction but not with the man sitting across from me.
- He said he would love to travel with me since we share a similar passion to see the world. He said I didn’t have to be concerned because his wife doesn’t mind.
Despite years of sporadic attempts at internet dating, I always ended up emotionally and sexually dissatisfied – no surprise there. Then a friend introduced me to Her Confidant. At first, I thought… am I that desperate to pay for sex? Well, the truth was, yes: I was that desperate to pay for good sex.
Sexual frustration is a strong motivator, and although I love the freedom of my single life, intimacy was severely lacking. I’m a busy professional woman in her 40s with limited time to meet men, and they are not lining up outside my door like it’s a sex delicatessen.
I then considered the stigma attached to the oldest profession in the world. After badgering myself with moral and ethical questions and fearing judgment, I thought f*ck it and booked an intimate adventure anyway. I was not going to be defined by old-school societal norms. Besides, I needed to feel desirable without the commitment of a relationship. I had been in a sexual drought for over a decade, and I was not going to wait any longer for a ‘tall drink of water.’
My hardest decision was selecting the man I would lose my escort virginity to. My only requirement was that he needed to be as tall as, or taller than me. I’m six foot and by no means a frail delicate flower. I’m a strong, independent, and proud career woman in her 40s. My male friends often refer to me as their Amazon friend or Princess Warrior – so you get my drift?
My tryst was to be with Bokeem. It was his voice reading a piece of erotica that attracted me first, but his description — 6.1” tall, athletic, strong — was in no way discouraging. I was nervous making the booking, but Anna was wonderful. I felt immediately at ease discussing my needs with her. I even admitted my greatest fear was that I had forgotten what to do in the bedroom. I may have even asked if they had a user’s manual I could borrow?
I was in my lavish hotel room ironing my dress for Bokeem’s arrival when I received a call from Anna.
There’s been a mishap.
Nerves had me thinking he’d been in an accident, injured himself, or worse yet, broken his penis. Stupid, I know, but I was freaking out a little.
Bokeem’s good clothes for your appointment tonight have been damaged as his massage oil bottle leaked throughout his overnight bag. Would you mind if he turns up in the clothes he wore on the plane?
Good. No broken penis. Of course, I replied.
Wonderful, I will let him know, then Anna added, he should be there soon.
I finished ironing my dress and had just put it on when I heard a knock at the door. “Shit,” I exclaimed with a whisper. I took a breath and opened the door.
Wow! He was gorgeous. Tall, dark hair, piercing eyes, and a bronzed body. I could see the muscular definition of his body through his t-shirt and shorts. His attire instantly relaxed me, and I was grateful for his massage oil accident.
He said, Hi, I’m Bokeem.
I extended my hand, gave him a firm handshake, and invited him into the room like it was a business meeting. WTF am I doing? He smirked but did as instructed.
He sensed I was nervous but put me at ease instantly with idle conversation, light touches, and his soothing deep voice. He encouraged me to move to the bed for a massage, with my clothes on, allowing time for me to get comfortable with his touch. Then he leaned in to whisper in my ear, and I felt his erection on the small of my back.
Shall we remove some of your clothes?
That was the only encouragement I needed. I removed my dress, revealing the expensive lingerie I had purchased for the occasion. I stripped him of his clothes, and our lips met. I was on fire with desire – or more accurately, lust – and I wanted to be ravished by him. Let’s just say… mission accomplished. Apart from a knock on the door from angry hotel neighbours unhappy with the noise emanating from our room, it was the perfect rendezvous.
The experience was liberating, satisfying, and empowering in ways I hadn’t anticipated. At 40-something, I realised I had never enjoyed my sexuality more than I did now. I felt more comfortable in my own skin, more aware of my desires, and more confident in pursuing what I wanted – without fear, without judgment.
This wasn’t just about rediscovering sex; it was about reclaiming my power and embracing a part of myself that had long been dormant.
Sexuality in Your 40s
This story isn’t just about a first night with an escort. It’s about embracing your sexuality, no matter your age, and refusing to let societal norms define your pleasure and desires. For many women, the 40s can be a time of sexual rebirth — a period when you finally feel confident enough to explore what truly satisfies you.
Kim Cattrall said to Glamour: “Most women, they’re too nervous, too anxious, or they haven’t done their homework to find out what feels good,” she said. “Sexuality is not just about having babies, not just about getting off. It’s expressing something in a very intimate way.” She shared plenty about experiencing ‘late-blooming sexuality’. This newfound confidence and openness about it reflect a broader trend among women who are redefining what it means to be sexy after 40.
Even Jennifer Aniston had widely spoken about the liberation that comes with age: “I’ve had more fun post-40 than I can remember.”
The Science Behind it
Research supports this idea of a sexual resurgence in your 40s. Multiple published studies found that women in their 40s often experience a peak in sexual satisfaction, driven by emotional maturity, self-confidence, and a deeper understanding of their own bodies.
Dr. Linda Kirkman even said, “[My PhD] research shows … that people in their 50s and 60s were having the best sex of their lives.“
Moreover, hormonal changes that occur during this period, while often challenging, don’t necessarily diminish sexual desire. In fact, many studies from the Kinsey Institute highlight that many women report an increase in libido during perimenopause and menopause, as societal pressures to conform ease, and they feel freer to explore their sexuality.
Embrace Your Sexual Journey
So, whether you’re exploring new territories with a professional like Bokeem, rediscovering your pleasure with the newest toy on the market, or reigniting the spark in your current relationship, your 40s offer an incredible opportunity to redefine and reclaim your sexuality. It’s a time to break free from societal expectations, embrace your desires, and celebrate the unique, powerful woman you’ve become.
This journey is about connecting with yourself on a deeper level, understanding what you truly want, and giving yourself permission to go after it. Your 40s are not a time to settle; they’re a time to thrive, to explore, and to enjoy every facet of the life you’ve worked so hard to build.
The key is to do what feels right for you, without fear or judgment. And if you’re ever in doubt, just think of the many women who have come before you, who have refused to let age define them or their sexuality and have shown us that our 40s can be a time of empowerment, liberation, and, yes, incredible sex.
At Her Confidant, we’re here to support you on this journey. We believe that every woman deserves to feel seen, desired, and pleasured at every stage of her life. Whether you’re looking to explore new experiences, reconnect with your sensual side, or simply enjoy the freedom of your 40s, we’re here to help you every step of the way.
xx Anna
Her Confidant is Australia’s premier elite escort agency for women, founded by Anna Grosman. Anna is a powerhouse: a wife, mum, carer, and lover of all things sex. Her nurturing nature and commitment to helping others led her to create an agency grounded in compassion, empathy, and strong work ethics. If you have any further questions, you can always read through our FAQ or get in touch for a confidential chat on 0449 918 907.