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.

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!

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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

Sharing our stories helps others feel better about their lives

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It happens often that I will meet a client who says to me “I thought I was the only one who…”.

It is counter intuitive that in this age of “connectedness”, via social media, phone, Zoom et al that people can still be left feeling that their situation and problems and challenges are unique.

But it’s true. And time and time again people tell me that they read a post on my website that included a story from someone I have met and in it they saw themselves – or an aspect of their lives – and in seeing that they realised that there was hope to change their situation and have a better, healthier life and (usually) sex life.

The reality is that although we are hyper connected through smart phones and the Internet – it is generally a superficial connection. We see the curated version of our friends and families lives. Not the hard realities of managing relationships. Of loneliness. Of bad sex. Or no sex. Of our inner conflicts over what we want versus what society tells us we can have.

It’s only when you dig deeper into the Internet (and end up somewhere like my website) that you start to find the stories of people who are prepared to share their real selves. And when you find that there is a chance to see yourself reflected and find validation of something that you may have been carrying for years with shame, or guilt, or sadness.

You are not the only one who has never kissed another person.

You are not the only woman who can’t orgasm easily – or at all.

You are not the only one who likes anal play or sex.

You are not the only person who doesn’t need to be in love to enjoy sex with another person.

You are definitely not the only person who is bi – or feels conflicted or excluded because of it.

You are not the only person who is bored of sex with their partner.

You are not the only person who wants a better sex life and is asking “should I book a straight male escort?”. The answer to that is “maybe” – but I’m happy to talk to you if you have questions about the services that male escorts for women provide and help to allay any fears you may have over privacy and safety.

John.

Help for couples with no sex experience – guidance and instruction about massage, touch, tantra, mutual oral, virginity, and more

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Not everyone who gets married has the sexual confidence and experience that they might like to have. It’s quite common for younger couples especially. Perhaps you come from a conservative culture and background, perhaps you just never had the chance to learn. It doesn’t matter how it happened – and it doesn’t mean you have to live with not knowing.

For many years now I have offered lessons to single women to help teach them about their body and help them explore their sexuality. I have also occasionally seen couples with similar needs, but I haven’t really written about this before and I thought that I should.

So here’s the bottom line – if you are a couple and one or both of you are inexperienced with sex (or even never had sex at all) then I can help you with practical instruction. I’m not a therapist who will just talk to you about what to do. As a straight male sex worker for women, I can provide practical experience in any area that you want to explore and gain confidence in. I can guide you and your partner through all of the things that you want to learn. I can demonstrate techniques (like how to give great oral sex to each other) showing both of you what works and how to learn about what each other likes. I can answer any questions that you have but don’t know who and how to ask.

My courses generally start with the simplest thing of all: touch. It can be literally just touching your partner’s body, it can be massage – which is a great way to explore and arouse your partner, it can be more sophisticated and sensual like intimate touch. I can show you all of these things and you can practice them with me and get feedback about how you are doing and improve your skills.

An extension of touch is oral sex. It’s an excellent way for a man to help his female partner to reach orgasm if she has trouble doing so through other means. I am very skilled in this area and can teach a man all of the techniques that he needs to be able to satisfy his partner. Conversely, I can show a woman how to touch her partner’s penis and teach her the techniques that make for great oral sex for him.

Are you a couple, newly married, and want to learn how to give each other erotic massage? I can help you with that. I can teach you how to give a massage that starts out relaxing and enjoyable, then builds up to sensual, creating lots of sexual tension and getting you both ready for some great sex…

Some couples are even in the position where one or both of them are virgins – have never experienced penetrative sex. I have met a couple from India in this situation in the past. This can be very stressful for both of you, but it’s a situation that I have been in many times and I can show you how to have sex for the first time without it being painful and help you to learn to make it great.

Techniques like tantra are especially good for couples to allow them to connect deeply and to make the sex that you have last as long as you want and to make it very satisfying. I can show you these things too.

Once you have the basics worked out, you might want to learn and experience more. If that’s the case, then I can help with that too. Advanced positions for sex, games like spanking, blindfolds, light BDSM. Anything that you can think of, I can help with practical guidance and instruction.

There is so much to explore for new couples and couples new to sex and I can be your guide. Safe. Knowledgeable. Discreet.

You can drop me a text, or email, or call me any time to discuss with no obligation and no risk.

John.

Sex for the first time – for best results, do it more than once!

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Every year I see about five or so women who want to experience penetrative sex for the first time. Now if this topic is of interest to you and you have read my posts and articles about it, you will know that I recommend a longer date – preferably overnight, but at least a full evening. The reason I do is that is it allows you to try sex more than once – preferably up to three or four times. That’s basically impossible to do in a one or two hour booking.

But why does it matter? If you’ve done it once, then you’ve done it right?

That is true – but it’s not the path to the best experience, and personally I think trying sex multiple times puts you in a much better position to enjoy sex the next time you have it.

Some background: when you have sex for the first time you are probably going to be tense and at least a bit nervous. You aren’t going to be really relaxed, even if you really want to do it. All of that is perfectly natural, but it means that the experience of having something as big as a penis in your vagina for the first time is going to be a challenge. It shouldn’t be badly painful – if it is then there is a problem and you and your partner need to slow down and perhaps go back to finger play and things that let you get used to the sensation and experience of penetration. At worst it should be just uncomfortable, with some occasional twinges.

Then there is the simple biological reality of the muscles of your vagina learning to stretch as required. In this regard, they are like any other muscle in your body – if you want to do the splits, then it takes time and patience to lengthen the muscles in your legs so that they can stretch easily without pain. Granted, vaginal muscles do this quicker and more easily, but it still takes time.

So. The first time you succeed having penetrative sex, you have mostly covered all of the stuff above. But it wasn’t going to be great sex – just like doing stretching exercises aren’t as much fun as getting to your goal.

And if that is where you leave the experience – especially if you are seeing me and don’t have options to try sex again soon – then you are going to look back on the experience and at best say “oh well, it was ok, but nothing special, what’s the big deal about sex?”

Well, the “big deal” may start to become apparent the second time, or the third time you have sex. I have seen it happen so many times – a woman having sex for the third time and saying “oh… now I get it! Yeah it’s still a bit uncomfortable, but it’s starting to feel gooooood!”.

So this is what lead me to recommending that women wanting to have sex for the first time book a longer date. When it’s over, you are going to walk away seeing the pleasure potential of sex and probably having actually enjoyed it. And that to me is the goal – not just to give you an experience that lets you say “well that’s done” but to leave you ready to explore your body and looking forward to finding out just how great sex can be.

I do realise though that a long booking may be financially difficult for you, or you simply may not want to commit to doing the whole thing in one go. In that case I recommend three or four short (two hour) bookings instead. Arranged close together, say over a few weeks, you basically get the same outcome and we can arrange it so it doesn’t cost more.

In conclusion: our society fetishises “virginity” way too much, to the point of it being unhealthy. But that statement also fails to recognise that having sex for the first time genuinely is a big deal for most women, regardless of their age or other experiences, and it really should be treated as such. Most men don’t respect that fact enough and society as a whole needs to find a balance between *OH MY GOD YOU’RE A VIRGIN” and “Virginity is a social construct!”.

It makes me happy to be a part of this conversation and to be able to offer an experience that many women want and need.

John.

No one needs to, or should live without the sex that they desire

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My entire life society has been telling me a lie. I’m sure that you have heard this lie too. And if you are aware of your needs as a sexual human being – and especially if they are not being fulfilled – then you are probably acutely aware of that lie.

The lie:

Sex doesn’t matter. It should come after every other responsibility in your life.

We hear this lie all the time. Everywhere. It usually won’t be explicit – unless we actually say that we want and need the sex that we are not getting – it’s usually a more subtle pressure…

Study has to be your priority, you don’t have time for a girlfriend/boyfriend.

Work comes first – you have to build a career…

As a parent you have to make sacrifices…

Each of these things are important. We do have to study if we want to improve our chances of getting the education and job that we want. We do have to build a career to provide for ourselves and our family. We do need to look after and provide for our children.

But these things shouldn’t always come at the expense of having a rewarding and satisfying sex life. If they do, then where is the room for having a sex life at all? Because we can always study more. Always work harder. Family will never stop making demands on us…

Part of the problem is that society tells us that we are only allowed to have sex under certain circumstances (in a relationship primarily). But what if we don’t want to have a relationship? Or what if we have a relationship, but it’s sexless? What if we are trying to find a relationship, but we can’t?

Why should a person be excluded from having physical intimacy just because we can’t be what society wants us to be?

At the end of the day, if you are a person who likes and needs sex in their life, then being denied sex will have real consequences emotionally. I know this, because I have been there. For much of my life I couldn’t have the sex that I wanted to. Now as a male sex worker for women, I have enough sex that I am satisfied – and I can see how it makes a difference to my mental health, my ability to concentrate.

Having a fulfilling sex life has literally changed the way my mind works, where once sex was a distraction that ate into my attention every day, now it is something that is in balance with the rest of my life. Letting me concentrate on other things as well that bring joy to my life that may once have been excluded by an unsatisfied need.

I know that I am not alone in feeling this way – because it is something that I hear semi-regularly from the women I meet through my work.

So, if you feel that you need more sex in your life – don’t let anyone tell you that it is not a valid way to feel. It’s ok to own your feelings. And it’s ok to want sex

John.

Performance anxiety – it’s not just for men

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Today I read an article in the local paper written by sexual health therapist Matty Silver. You can see it here.

It’s a good article focused on male sexual performance – or lack there of. It’s something that rarely if ever sees the light of day in the media. After all much of the time the media wants to paint men as either macho machines, or one dimension slaves to their penis, so talking about men feeling intimidated by, or unequipped for a healthy sex life rather breaks the stereotype du jour.

In reality men have their own issues around sex. Plenty of them. Personally I fought premature ejaculation for many, many years. I was lucky to come across a book by Canadian doctor Sy Silverberg. Along with some assistance from a kind partner, it changed my sex life forever, and allowed me to enjoy sex in a way that I had never been able to before.

All in all, I think that this article is a step in the right direction – it demonstrates that we are all complex, emotional, and more or less fragile beings. Something that should be respected.

What jarred for me though was the second last sentence:

Women don’t need to perform – they can just lie down and don’t need to do much – they can even fake an orgasm!

I understand what Matty Silver was trying to say with this, yes, there is a very obvious difference between men and women, women don’t need to get an erection to participate in sex, yes they can “just be there”.

But really?  An otherwise sensitive article that accepts that stereotypes about male sexuality are damaging then goes and drops another unhealthy stereotype on women. It seems wrong.

Not all women can just “lie back and let it happen”. Nor should they. And it’s a bad message for anyone with a platform like a major newspaper to be sending.

What I would rather see is the acceptance that women and men both can have performance anxiety. It may not be so clearly evident in a woman as in a man, but for a caring lover it should still be obvious through body language, through lack of vaginal lubrication, and lack of relaxation. These are all things any partner who cares to look for them can see.

I often meet women who come to me because they need a chance to explore their sexuality and build their confidence in themselves and their body and their ability to enjoy sex in a non-stressful, non-judgmental situation. It is something that I can offer, being an escort that (to many people’s surprise) women often can’t get in a relationship.

This really is the problem though, for both men and women, often regardless of age. We are never given the opportunity by life to develop the skills and confidence with our bodies that we need to have a healthy sex life. I do what I can through the services that I offer, but really there needs to be a community wide change in attitude to sex, sexuality, and relationship.

Personally I think that it is time for these issues to be given as much attention and priority in our society as learning maths and (in Australia) English.

John.