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Dealing With My Virginity as an Older man

Dealing With My Virginity as an Older man

Hi there. I am feeling like I'm taking a huge risk by posting this. I am a 50 year old virgin. I am still not 100% about how I got here. Apologies for the very long post by the way.

I think the issue started when I was in primary school where I was pretty much bullied from year one though to my final year of high school. From this I really, really developed a mistrust of everyone except my immediate family and shunned social situations like the plague.

This really carried on into my working live when I shunned social situations for the most part. I was interested in sex when I was a teenager for sure, but never really entertained the idea of have a girlfriend ever. It turns out I had undiagnosed Asperger's syndrome, which I would not discover I had until I was 30. So even when I was in social situations, I think I never picked up the non-verbal cues.

When I was 20, I met a woman at work and I don't know if it was love, but I really fell so hard for her, like I could never get thoughts of her out of my head. But I just felt frozen and didn't know what to do. After I left that workplace, I fell into a deep, deep depression which lasted for around four years.

I went and saw counsellors via the EAP program at work, but I felt like they just dismissed my concerns or gave me terrible advice. Afterwards I eventually saw a real psychologist when I was about 30 who was very empathetic, thought I had Asperger's and sent me off to a specialist who diagnosed me straight away. She offered to help me with the relationship issue, but I think I was utterly overwhelmed at how big everything was to tackle and was trying to cope with this diagnosis and I didn't want.

I think at this point somehow psychologically I had made sure I never fell in love again. It was like I had compartmentalised that side of my emotions off and locked it away. In the decades after there were a couple of times at work where I think a couple of women were interested in me, but I know really stuffed it up on one occasion, I think mostly because I had no idea how any of the social stuff worked. In addition I read this book about Asperger's and love written by a woman who was a partner of man with Asperger's. It really read as if it was the partner of the Asperger's man who took the brunt of the issues with the relationship and they always found it difficult. I was horrified and felt I really couldn't do this to any potential partner.

Literally, it took me two decades from there to figure out the social rules for talking to people. I think my the time I was about 40 or 45 I felt really comfortable making conversation, though sometimes I stuffed up. However I still shunned most social outings and felt happier being at home by myself.

However the depression and anxiety cause by my workplace reared up and with that feeling of utter sadness about the lack of relationship issues, more so as I got older and older. When I left that workplace and was bullied by some of the staff at my new workplace six months ago, the depression came back big time.

Along with me turning 50, something snapped. I went to the psychologist again but after a couple of sessions found her frustrating. However at the same time I sort of confided in a friend/work colleague a bit, but before then I think realised my predicament and sort of hooked me up with one her friends in December. So far we have had two dates, things seem to be going OK and she texts me reasonably often. I am literally making it up as I go along in terms of the dates, but everything seems fine. I am going to try and sort another date out once she gets back from the Elvis Festival this weekend.

In addition, I got sick of psychologist and decided to see a sexologist. I think she gave me some great advice, some of which I haven't taken up yet like using that Meetup app, but I asked her about going to see a sex worker, to demystify the whole process and honestly to take the virginity, and she said it might be a good idea. She gave me the name of a sex worker at a brothel.

So I pondered over for this a while and decided to take the plunge. The lady wasn't working that week, so last Wednesday I booked someone else, I just picked someone who was my type really. I went in, I could not believe how calm I was, got taken to the room.

TW: Sex

Content/trigger warning
I had no idea what I wanted, so she just started off with a bj, and it was terrible. It was like I had my willy stuck in a washing machine. She then tried to mount me, but it just wasn't happening, barely got in her, I was completely flaccid. No amount of terrible bjs in any positions helped with the issue. We both expressed disappointment, and I just ended up taking to her for remaining 25 mins of the hour we had.

Initially I don't know if I was happy that this had happened, but I felt zero emotion to all of this. Then soon after, so many questions, so much confusion; was I asexual? Did I not like having sex with women? Am I man that hates bjs? Am I even a man anymore? I pretty much immediately booked another appointment with the sexologist, but I can't see her for three weeks.

Since Wednesday, I have had a flood of emotions and have been so upset. This was meant to be an easy win for me, to have sex with a really beautiful woman who takes my virginity and try and help with my really low self esteem. It's just done the opposite instead.

I confided in my friend/work colleague who knew I was doing this, but she has been giving me terrible advice lately, doesn't believe in getting psychological help or medication and has been pushing me and pushing me to do stuff that is way beyond my comfort zone. As I result I feel the relationship is becoming strained and she is making me stressed.

At the moment I fighting my very, very deep seated beliefs that people cannot be trusted and will betray you if do trust them. And it is so, so very hard for me to overcome that, it has such a grip on me. My friend/work colleague has dismissed how I felt in regards to this and how horrendously hard it is for me which has made me even more depressed. It got so bad I rang Beyond Blue last night, which did help me a bit.

I still want to go out on a third date with this lady I've met, but now I'm very confused about my sexuality, my relationships/lust/desire for women and if there will be any reward for all this pain I'm going through. I just feel utterly miserable and wondering if the this journey of self improvement was a good idea at all.

7 replies

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In response to: Dealing With My Virginity as an Older man

Re: Dealing With My Virginity as an Older man

Hey @WJK ,

It sounds like you are doing what you can to better yourself. I'm sorry to hear that so much bullying has resulted in a severe mistrust in people.

The fact that you are taking active steps towards finding help is a great start. I recognise you are now pondering about your sexuality and trying to navigate things best you can.

Have you ever contacted QLife? You may find talking to them helpful. https://qlife.org.au/

Let us know how you go. We are here to support you. Well done on reaching out. This is a huge step.

In response to: Re: Dealing With My Virginity as an Older man

Re: Dealing With My Virginity as an Older man

Hi @tyme

Thanks so much for that. I'm am positively sure I am heterosexual. I have always adored women since I was young. After I talked with the lady at Beyond Blue I realised that I had completely switched off before I even entered the brothel, maybe even before I woke up that day. When everything was happening to me it was if I was watching a movie screen and it wasn't real. I realised the experience was really sterile, the environment feel that way too and just felt like a medical examination, utterly devoid of any sensuality, which I realise is really what I want now. I still have to go back to the sexologist and confirm this.

One thing which frightened me was the next day was a colleague, a young woman whom I really fancied, came to talk to me and really out of nowhere this thought came into my head while I was talking to her; "you have no sexual power over me now", and I'm like, what? Where on earth is this coming from? I just have had all these strange thoughts

about who I am what is going on, but I think it's because I have built up in my head over the last 40 years what sex should be and my relations to women and how I view them, and it went wrong and I've just gone bonkers really.

I think in addition to the bullying, not having a large circle of friends, and for most of my life no friends to speak of, really entrenched that deep seated distrust but also an incredibly deep seated hatred of myself, which I am finding extremely difficult to silence. It's got such a grip on me. It is really frustrating.

Thank you for replying so quickly.

In response to: Re: Dealing With My Virginity as an Older man

Re: Dealing With My Virginity as an Older man

@WJK welcome to SANE and possibly welcome to the LGBTQ+ community,

Have you thought of joining a neurodiverse discord server? they can be very enlightening and helped my guy trans daughter, when she found her true self. There are so many sexualities that people don't think of, for years I thought I was straight and realised that I have to have a emotional connection with someone to be able to be intermate with them, but in saying that I haven't had sex in almost 7 years and not really fussed about it. I think I'm somewhere between pansexual and asexual.

Have you thought about watching some "movies" to see what interests you?

This is your time to shine and work out who you are, this is your discovery, be you. If you ever want to talk you only need to tag me

In response to: Dealing With My Virginity as an Older man

Re: Dealing With My Virginity as an Older man

Welcome, @WJK , it's good you've joined 🙂

I really feel for you. I also have issues with sex and intimacy and trust. I do think you need to trust the person you're intimate with - at least, some people do and I am one of them. (I am a 52 year old female) Maybe that's why the session with the prostitute didn't work for you?

I would recommend a psychologist or counsellor to talk about some past issues with, like your trust issues, as well as your sexologist.


@WJK wrote:

I still want to go out on a third date with this lady I've met, but now I'm very confused about my sexuality, my relationships/lust/desire for women and if there will be any reward for all this pain I'm going through. I just feel utterly miserable and wondering if the this journey of self improvement was a good idea at all.


As a woman, I think the journey of self discovery you are on is admirable. I know I wouldn't go out with anyone, male or female, who wasn't trying to work on their issues.

I don't know you, but I know for me any sexual encounter needs to be very slow, caring, gentle and not rushed. That hasn't happened so I've barely had any sex in my life and have not enjoyed it. Which means I am also questioning my sexuality at age 52. I've decided it's far better for me to be single as well.

As your relationship with the lady you've been on 2 dates with progresses down the track, I wonder how you'd feel about telling her some of this? That might mean you have a helper along the road of sexual intimacy later on. Just a thought.

Anyway, I wish you heaps of good wishes as you struggle with all of this...

An important forum tip is if you type @ and then click on a name in the drop-down box, that person will get a notification and won't miss your reply.

In response to: Re: Dealing With My Virginity as an Older man

Re: Dealing With My Virginity as an Older man

Hi @NatureLover

Thank you so much for the well wishes. I'm sorry that you've had those issues in past relationships.

Having had time to calmly think things through (and I was absolutely not in the right mindset from Wednesday night through to Saturday morning), I think that was the issue with my first sexual encounter as it was neither slow, caring or gentle and was completely rushed and full on. There was no build up at all, just bang, we're on. I noticed as I got into the car, that my genitalia wasn't sore or hurt, but felt that it been roughly handled and it wasn't fun at all. I really felt she was all "get it over and done with and it's onto the next client". In addition, I do think subconsciously I completely dissociated myself from what was about to happen, maybe for self preservation.

I do think I have more of an idea of what I want and I'm sure it's sensuality and I do think it would be a thousand times better with someone who I got to know and trusted over a period of time. In addition I think you are 100% right and this will end up as an exploration of my sexuality and who I am, which feels weird at 50 and I feel like I should have done this as a teen, but here we are. I was told by my friend that when I saw the sex worker everything will happen naturally, and that was so utterly wrong and bad advice.

I know I will have to tell the woman I am dating at one point what is going on and my history. I'm really hoping she understands but from what I have been told she has dated neurodiverse people previously. I feel like emotion will get the better of me and it's just going to come out in one huge infodump and I'll be blubbering and crying my eyes out at the same time. I just need to figure out when is the right time to say that stuff.

I think will have to go back to a psychologist for the trust issues. I am seeing that sexologist three weeks from now so I'll see what she says and recommends. I think the issue for me and psychologists is trying to find one that understands and is compatible with me. I feel like some of of them don't listen at all and run through a script and I'm like, "hey, did you listen to a word I say? This is all irrelevant to my issues". I've had a few good ones, but they have all left the industry.

In response to: Re: Dealing With My Virginity as an Older man

Re: Dealing With My Virginity as an Older man

Hi @Miss-wish and thank you for comments. I'm glad you and your daughter have found out who you really are.

Do you have any recommendations for which neurodiverse discord server I should join? Going to be honest, I have never used discord before.

I've had several days to calm down and think things over, but I still think I am straight and it was just the shock of everything which happened. I think if it was a much more calmer and sensual experience rather than bang, let's go straight to it, it might have been at least a bit pleasurable. However I'm sort of open to whatever happens and I think if I discover who I am, I think I should be happy enough to go down that path.

But as I have mentioned before, I think the emotional connection and sensuality of what should be coming before hand is something I think I would like very much and was completely absent with the sex worker.

I have watched "movies" and do know what interests me. So I have always dreamed of the number one act men like (trying not to get hit by the censor here), but when she did it, it was horrendous. I sort of wondering if she was trying to remove it from my body via pure suction. It was just frenzied and uncomfortable and I could feel teeth at a couple of points. It was at the that point I sort of questioned everything as this was not what I expected or was promised. It was supposed to feel like I had gone to heaven. There is a good chance that she is just crap at her job and it was just a dud experience for me.

I would love to talk more, but I sort of feel a bit limited by message boards at times. I feel at times there is very limited opportunity from more back and fourth conversation. But I'm more than happy to continue the conversation here.

In response to: Re: Dealing With My Virginity as an Older man

Re: Dealing With My Virginity as an Older man

Hi @WJK , you sound calmer and your thinking sounds good.


@WJK wrote:

In addition I think you are 100% right and this will end up as an exploration of my sexuality and who I am, which feels weird at 50 and I feel like I should have done this as a teen, but here we are.


I can relate to this! But I was just trying to survive before now.

Good luck finding a psychologist to match. I took 18 years before I found two excellent ones in succession (one retired). So it's worth hanging in there till you find one that's good and that suits you. I know I've got a lot of healing through therapy. (I haven't really talked about the sex issues though yet).

Best wishes @WJK ...

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