Category Archives: Virginity

If you are interested in the questions around losing your virginity, particularly with a male escort, then these articles and posts may be of interest to you.

One woman’s story

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I recently met a woman who had never had sex. I don’t think that I can say anything about our experience better than she can, so I’m sharing a very generous testimonial that she wrote for me after our first date together…

Getting out of my head

I had been checking out John’s website for years. About five, actually. I first stumbled across it as I went down internet rabbit holes on virginity as an older woman. I was mid-forties and feeling very, very isolated.

Mostly, my life is great. I am university-educated, at the peak of my career, I have a wonderful job, my own home in the city and a holiday home near the ocean. Sure, I have a mortgage, but I have enough disposable income to travel widely. I have many wonderful friends – people who care about me and who seem genuinely baffled by my decades of being single. I have never been in a relationship and have never had sex with another person. [I also never use the term virgin, except in those internet searches, as I believe virginity is an archaic concept, from a time when the purity of women was commoditised by men].

Somebody I’d once confided in assured me that ‘when the time comes, he’ll be a very lucky man!’. Whilst they meant well, actually that was part of the problem for me. I didn’t want a guy fetishising my age and lack of experience, or thinking I’d ‘saved myself’ for him. Even if I did meet someone, to me it would have felt excruciatingly more vulnerable to tell him that I’d never had sex, than to actually have sex. I wanted him to know, because it did matter to me; but I also needed it to be ‘no big deal’ to him.

I have been working with a psychologist to unpack how exactly I ended up in this predicament. As always – it’s complicated. One of John’s videos brought me to tears when he addressed this: it felt like he was in my head, he was describing me so accurately. [ShortTake – Virginity] Add some family dynamics, a career with gruelling hours, societal and religious shame about sex, and life was just passing me by. One of the things we often talked about in therapy is how I need to learn to get out of my head and into my body. Massage, yoga, meditation, being in the ocean – all of these helped, but the underlying ‘problem’ remained; and as the years passed, I was becoming increasingly reluctant to even discuss it.

As well as reading everything out there on virginity, I also explored the concept of asexuality. I could relate to the description of people who identified as asexual, saying “it was as if everyone else had a switch that flicked on as teenagers – but not me, somehow I didn’t get the message to start wanting relationships and sex”. I’m not sure if I feel sexual attraction, which is a definition of asexuality, but I do have a healthy libido and have a respectable number of sex toys. I have great orgasms. Ultimately I’ve realised that for me, a label doesn’t actually matter. What matters is knowing what I want (intimacy, kindness, companionship and a good sex life) and who I want that with (men, I think). It feels strange being 50 and trying to figure out stuff that most people have sorted by the time they’re through adolescence; but here I am: better late than never!

I began to realise the harsh reality that I needed to either do something about my situation, or accept that I might never have sex and just get on with my life. Staying in limbo was doing my head in.

When I contacted John during a holiday in Sydney, I wanted to talk with him about all things sexuality, to learn about myself and what all the ‘stuff’ in my head means. Of course, I knew he wasn’t a therapist, but he clearly had experience in talking with more women about this than any licensed therapists would ever have. I very nervously hit the send button on an email:

“….I’d be keen to meet with you for a couple of hours, actually mostly to talk and maybe a massage. Not planning to go all the way this time but considering in the future. …”

My heart jumped when I got a reply within a few minutes:

“….Thank you for contacting me. It would be my pleasure to see you. … Talk and a massage is perfectly fine. I understand not wanting to go all the way and there is no pressure to.”

From the moment I met John, it was clear that his website is a totally accurate portrayal of who he is, his values and how he works. He arrived on time, we started chatting and, in the absence of a sofa in my hotel room, moved to the bed to lie down and talk a bit more. Within half an hour, we’d gone from being complete strangers, to me telling him all of the above, and lying on a bed together, kissing (something I’d also never done, but he offered to teach me, without judgement). Then he asked if I’d like a massage – at that point it dawned on me that in our talking, I’d once again been fully inside my head, and that getting into my body was what I desperately needed to do.

Each step of the way the massage was done with utmost respect, kindness and consent; it also flowed naturally as he read my body. I had no idea how much I would enjoy nipple stimulation…. I had already decided I might be ok with oral sex at the end of the massage, so when John asked about removing my underwear, my answer was an enthusiastic yes. I got very close to climaxing, but after a (very) long time wasn’t quite there yet. I made a decision: “Um John, I think I need you to fuck me properly”. He promptly stopped, put his head up and with a kind smile responded “we can do that!”. And so we had sex. Then we chatted some more. And he asked if I’d like to have sex again (yes please, didn’t know you could do it again so soon….), he asked if I wanted to put the condom on and showed me how. I chose what position I wanted, and we had sex again. It was very, very good….

More talking, more cuddling and eventually our evening together came to an end.

I slept like a rock. When I woke, I couldn’t stop smiling. I felt in-control and empowered. As I left the hotel, I wanted to shout to the people walking the streets of central Sydney “I HAD SEX LAST NIGHT! And it was so much fun!”. For the first time in my life, despite not having had children (not by choice), despite being in a bigger body, despite having had a hysterectomy, I felt like a woman. A sexy, complete woman. I genuinely didn’t expect that a couple of hours with a stranger could feel so overwhelmingly good – both in the moment and in the change that I feel in myself afterward.

I know John says he can’t work magic, but I’m prepared to accept that something in me changed in a way I can’t fully explain: and it was wonderful. That switch that didn’t get activated in adolescence? It’s now dialled right up. Now, I feel like I’m walking around with the lights on and my eyes open. Life really does feel that different – even a few months later.

If someone had told me 30 years ago that this is how I would have sex for the first time, I would have been shocked, and to be honest, quite embarrassed. I spent years tortured by uncertainty about whether I was fundamentally ‘abnormal’ or if I ‘just hadn’t met the right person yet’. I feared what it meant about me if my ‘right person’ never existed. I hadn’t considered the possibility that perhaps my own body had wisdom to listen to. I certainly hadn’t given myself permission to just have a whole lot of fun with my body!

My only regret is that I didn’t ditch the dream of the white picket fence earlier, but I am grateful that I can now move ahead and fully embrace this one precious life that I have. Yes, my way of having first time sex was definitely unconventional, but so was my journey to get there. My mind was tying itself in knots trying to think its way out of this. Getting the hell out of my head, and into my body was one of the best decisions I have ever made. No regrets. And yes, I have another booking planned.

D.

John

Social anxiety and isolation and what a male sex worker can do for you

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In these post covid days social anxiety and isolation are on the rise. Perhaps we work from home – which can be a good thing – but that comes with more isolation. Cost of living increases make it harder to afford to go out regularly like we might have done in the past.

This can make life extra difficult when you are already dealing with social anxiety but want to meet a partner. Isolation can create a downward spiral that just makes it harder and harder to effect change and get what you want.

So here is my offer to you if you have social anxiety or are feeling isolated and lacking confidence to make connections with men:

For a modest fee I can talk with you – by text, email, phone, or video chat. You can be anywhere in the world. We can work out a program that works for you and allows you to build your skills and confidence.

I can give you an experience with zero risk and I’d hope, some fun too.

John

Never had sex

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I haven’t written about this topic in a while, partly because I think I have said most of what needs to be said. You can read my previous posts here: virginity (at time of writing there are 16 articles relating to first time sex). I have also written some articles which can be found here: My offer for virgins

However someone sent me a link to this recent article from the ABC so since it’s topical again I thought perhaps it was worth covering again.

https://www.abc.net.au/news/2024-05-05/dating-intimacy-sex-women-hook-up-ladies-we-need-to-talk/103780054

The part that stands out to me in this article is how “never having had sex” effects people’s lives beyond just missing out on actually having sex.

From the headline “…make her feel like an outsider” – I was talking about this twelve years ago back when I was new to the industry and it understandably hasn’t changed.

When you haven’t had the experiences that your friends and family have had and you can’t share them – or worse you can’t even relate to them it has serious negative effects on your ability to connect with the people around you.

If you have never had sex it puts you on the outside in almost every social situation and that can be a terribly lonely and isolating place to be that will absolutely make your life less happy.

Jo’s last words in the article are: “You don’t really miss what you’ve never had, right?”

I disagree. You may not be conscious of what you are missing, but our bodies have a lot of stuff hardwired into them and sex and reproduction are one of the most primal aspects of our biology and psychology. Even if we aren’t conscious of missing something there will be effects – emotional and physical. I think that it is reasonable to say that we can miss something we have never had, even if we aren’t aware of what we are missing.

I don’t expect that Jo will ever read this post, but other women in a similar situation probably will. Let me say this to you: almost every woman who comes to me who wants to have sex for the first time (and I usually see at least two or three each year ranging in age from 20 to 45) say to me afterwards: “is that it? Why was I so worried about it?” and often “I wish I’d just done it earlier, I feel like I’ve missed out on so much”.

It’s always heartbreaking for me hearing those words. Our society makes *such* a huge deal out of sex – “Don’t have it! You’ll get a disease/pregnant/go to hell!”, “You must have sex or you’re not cool!”, “You can’t have the sex you want because [reasons…]”

So many conflicting pressures, so much stress over something that is and should be a natural and easy part of our lives.

The reality is that everyone deserves to have safe, consensual sex. If you have never had sex and you want to get over that emotional and mental hurdle then reach out to me. I am happy to talk and discuss your situation and your needs and if it feels right, give you an experience that set you on the road to a fulfilling sex life.

John

Yoni massage

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If you have spent any time learning about, or in the sex positive community then you have probably come across the term “yoni massage”, but you may not be familiar with what it actually means.

While browsing YouTube recently I watched a video on the topic that I thought was quite a good explanation.

In short yoni massage is the massaging of the area of the mons pubis, inner thighs including vulva and the perineum, and inside the vagina. For a more detailed explanation the video does a great job.

If you are thinking about booking a session with a straight male sex worker like myself, but you aren’t sure if you want to go all the way to having penetrative sex then a yoni massage might be a great middle ground to give you an intense erotic experience without being too challenging!

It can be a very enjoyable form of foreplay or it can be an entire experience in an of itself. It can also be a great starting point for a woman who is a virgin and wants to have sex for the first time (or for the first time in a long while), but would like to build up to the experience of vaginal penetration.

John

It’s always ok to end a session early – I won’t be upset or embarrassed

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I recently met a woman for an overnight booking (and with her permission) I’m sharing a story from our session together.  Now she had traveled a long way to see me – to have sex for the first time, so it was quite a big deal for her. 

She chose to book me overnight, which I encourage for women having sex for the first time as it gives them the opportunity to experience sex several times and reach a point with it where they are comfortable, can get past their nerves, and start to experience the pleasure that sex can provide.

Our session went well and she got to experience intimate touch, had her first orgasm assisted by someone else, and then experienced penetrative sex in a number of positions for the first time.

We took a break and chatted about the experience and issues around dating and sex.

Now I was booked to stay with her overnight, but at that point she decided that she had experienced enough and didn’t need me to stay.  So we ended the booking early.  She paid me for the time we had been together and I went on my way.

The reason that I am writing about this is that she was worried about how I would feel about her ending our booking early and that I might be upset.

So I want to be very clear for anyone who is contemplating a booking with me – you can always end a booking at any time and I will not be upset.  If you are not happy with my service, or it’s not working for you, or you have had enough, or any other reason then you can tell me and we can end it there.

It is really important to me that anyone who sees me understands that and doesn’t feel that because they have requested a longer booking that I have to stay for that long.  It’s your session and you can end it any time you want to without upsetting or disappointing me – and I will always adjust my fee appropriately.

John

Ask me anything…

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If you could ask me any question what would it be? About me, about male escorts, about the industry, about a date with me, or something else?

Drop a comment below, email john@john-oh-escort.com, or text 0437 520 539 and I’ll do my best to answer it for you.

So I have a few questions that have come in overnight. Thank you to everyone who contributed! I’ll add more questions and answers as they arrive.

Here are a couple to get started, but you can read them all here.

Q. What happens if you don’t find me attractive?

A. In the thirteen years I have been working as a male escort this has never happened. No, all of my clients are not super models! Most of my clients are normal women with all of the variety of looks and body type that comes with.

I am extremely lucky though that I really only meet decent people who are respectful of me and I can make a connection with. I think that this comes in large part from the fact that the vast majority of women who book with me take the time to read a lot of my posts here on this website and in doing so they get a clear picture of who I, what I value, and what I offer. The women who choose to see me generally share my values and therein lies the key – if we can get along and have fun together out of bed, then that for me is the foundation of attraction in bed.

Q. Is sex work legal?

A. The answer to that question is “it depends”. Australia is one the most progressive nations in the world when it comes to sex work. New Zealand is as well, but they were a bit slower off the mark!

The bottom line is that here in New South Wales in Australia (and Victoria, The Australian Capital Territory, and the Northern Territory) sex work is decriminalised – meaning that it is treated like any other job and not regulated in any way specific to sex work (there are minor exceptions to this but they won’t effect you as a client).

Queensland, Tasmania, and Western Australia all allow sex work, but it is regulated or or less harshly in those states. South Australia remains the only state to effectively criminalise any form of sex work (South Australia needs to do better).

Q. Do the interactions with clients feel transactional?

A. No they don’t feel that way for me and I do my level best to make sure that they don’t feel that way for my clients. I like to be informal, to chat and have fun together. I treat every booking like I’m on a date with someone I’ve just met and am looking forward to getting to know better.

Q. Do you talk dirty to your clients? Do you mind if a woman wants you to talk dirty to her?

A. Dirty talk can be a fun part of sex – if that is something that works for you! I have no problem with being asked to talk dirty and will happily oblige, but it’s not something I will initiate as not everyone likes or wants it. So please feel free to ask!

Read all the questions and answers here!

Continue reading →

Disability and first time sex/virginity

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I realised that I have left somewhat of a gap in my writing for women with a disability.  That is that for some women with a disability looking to book my services it will also be the first time that they have sex.

So I think that it’s worth acknowledging that fact as it complicates two situations that are already challenging – booking a male sex worker and having sex for the first time while working around a disability of some kind.

I have negotiated this hurdle with three women with disabilities in the past and with a bit of planning and conversation beforehand and plenty of patience and communication during the booking it has always worked out well.

From my experience it is generally just a matter of lots of foreplay, going extra slow, and checking in regularly. Do that and it’s going to be a pain free experience of sex for the first time is.

If you would like to talk to me about first time sex and disability issue please feel free to drop me an email or text. I’m always happy to discuss your needs and work out a solution that you are comfortable with.

John

Dilators and dicks – a story of accommodation

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We tend to think of painful penetrative sex as being a problem for women who are having sex for the first time. And that is true for most women their first times, but it’s not the whole story. There is something of an assumption that once a woman gets past that initial hurdle that – unless the guy has a huge dick – that it’s all going to be plain sailing.

The reality is that for many women, used to partners with modest sized penises, having sex with a man who is only somewhat larger can be challenging and even quite painful. There’s also women who suffer from the side effects of surgery and from physical and emotional trauma. All of these things can lead to painful sex or not being able to experience penetration at all.

The point is that whether a woman is new to sex, or has been having sex comfortably for years, she can still find accommodating a larger penis difficult.

So what’s the solution?

Well one solution is gentle stretching with dilators. Doctors and physiotherapists will often recommend the use of vaginal dilators to help stretch the muscles of the vagina and “teach” them how to relax. It’s a lot like stretching any muscle of your body – it takes time and practice. No-one expects you to be able to touch your toes comfortably – or at all – without practice, if you can’t touch your toes.

Having sex with a partner with a larger-larger-then-usual penis is much the same – only with added complexity and emotional challenges. Dilators, which usually come in a set of five or six in graduated sizes, are a useful tool to help women reach a point where they can have the sex that they want without pain.

I recently met a young woman who came to me to have sex for the first time. We weren’t able to have sex in the end because she needed more slow stretching of her vagina than the time we had together allowed. She did make a lot of progress though during our booking, demonstrating that it was possible for her to experience penetration without pain. I recommended that she buy a set of dilators to practice with – I would normally have had a set on hand, but I hadn’t replaced the last set that I had given to another client.

I have remedied that now and will in the future always have a set on hand.

Not long after that a regular client booked a threesome with another male sex worker and me. She has plenty of experience with sex, but not with anyone with a larger penis than me. She discovered that he -being a little larger than I am – was actually too big for her to comfortably have the sex she wanted with him. To that end I recommended that she try practicing with a dilator.

There was the small problem though that dilators are generally aimed at women with more extreme troubles like vaginismus that require starting with a very slim dilator and working up. So they tend to only go up to around 3.5cms in diameter which is probably as big as the average man’s penis, but definitely isn’t big enough for a woman wanting to graduate to a larger guy.

Her solution was to find a nice silicon dildo that was about 4.5cms diameter, which represented a modest increase in size over me and was closer in size to the other escort.

Now I’m not going to try to explain the best practice use for vaginal dilators as I’m not a doctor or physiotherapist and you should definitely talk to your doctor if you feel you need to use dilators for painful sex, but I will outline the basics that medical professionals publicly recommend:

Use personal lubricant! It will make things a lot easier – and remember, don’t use silicon lube with silicon dilators – only water based lube
Once you can insert a particular sized dilator, leave it in for approximately 15 minutes each time you practice – this gives your body time to adjust and learn to relax
Only practice every second day – this allows your body to heal from any abrasion or other strain that you might experience as you increase the size of dilator you are using

Probably the most important thing though is to take your time and persist. It’s not a process that can or should be hurried. Persist and you will reach your goal!

John

Consent training and education – we are taking a step forward

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As a male sex worker for women, consent – giving it, getting it, and ensuring that it is still there – is something that I have to do with every client, especially when I don’t know them well, or with women with disabilities who may not be able to communicate effectively.

I also go out of my way with women who have little or no experience – or sometimes bad experiences – with sex and consent to try to help them learn how to ask for what they want and reassure them that they are allowed to say no, to withdraw consent for things that they may not want.

I believe that I do this well and provide a service that is safe and respectful.

That this is even worthy of note indicates just how big a problem “consent”, its practice, and our understanding of it is in this country.

So I am delighted to see (via this article – https://www.abc.net.au/news/2022-08-29/consent-education-mandatory-australia/101375564) that the teaching of consent is to be federally mandated in all schools in Australia.

This is exactly how we make our society a better place. We teach our children in school and it creates generational change. Over time the young people who have learned what consent means, how to ask for it, and how to give it become the majority and “the old ways” die a natural death.

Some people fear this sort of education by the state and will claim that it’s the job of parents to teach these sorts of values. To that I say “You can’t teach what you don’t know”. Which doesn’t mean that all parents don’t necessarily understand consent – just that knowing something that you probably learned more by watching what other people did than actually being shown isn’t a great basis for teaching that thing effectively.

We very obviously have issues with consent in our society – I literally hear it from women regularly – and I for one am very happy that we are taking real steps toward addressing it.

It won’t be an easy road though. As mentioned in the linked article teachers involved in this kind of education need to be taught themselves about how to provide it, how to be sensitive to the impacts that what they are teaching may have on students who have suffered abuse for instance.

It’s a complicated problem that requires sophisticated thinking and solutions. It won’t be resolved over night, but every year that students receive this training we will be making a better society and giving kids the chance to live better, healthier, safer lives.

John