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A male virgin and a much younger and more experienced girl - potential humiliation or a great opportunity?

Tagged as: Dating, Sex, Virginity<< Previous question   Next question >>
Question - (8 January 2012) 41 Answers - (Newest, 7 February 2012)
A male United Kingdom age 36-40, *ovember_rain writes:

Hello! This isn't the first time I've asked a question that is in some way related to this topic, but I hope it will be the last!

First, some important background information.

Somehow I have managed to get to the grand old age of 27 while retaining my virginity. When I was younger, I always thought I would meet the right person to have sex with. I was brought up with the idea that it was only certain types of people who slept around, and genuinely believed that I would find “someone decent” like me who would also be a virgin.

I have come to realise over the past 6-8 years or so that this is not the case; it seems that everyone sleeps around these days. From what I've seen, even a quiet, mild-mannered girl in her early twenties from a nice family is likely to have at least a couple of notches on the bedpost!

Although I have been out with a few girls, I couldn't even consider myself to have had a girlfriend. I have been on a few one-off dates with girls who usually didn't want to see me again, and I would spend months afterwards trying to work out where I had gone wrong. As a result of this limited experience, I have never been in a relationship as such.

Part of my problem has been a lack of confidence stemming from a fear of rejection and fear of failure. I have been working over the years to resolve this and I think I am much now more confident in many ways, but I am by no means “there”.

So, here is my question. I have recently met a girl at work and have been seeing her. We have met up a few times now and she seems very keen on me, but she is actually only 18 and I have felt a little awkward about the age difference right from the beginning. This was probably exacerbated by the fact that she isn't really the type of girl that I would normally consider dating.

At first she seemed quite shy, which I put down to her age and possibly lack of dating, let alone sexual experience. However, we have had a few “sexual” encounters recently, which although not intercourse, have made me realise she is not quite as shy as first appeared. Today she told me that she has had a few sexual partners, and I am inclined to believe this as she did seem concerned that it would make her seem sluttish. I told her at the time that it didn't matter to me, but in the back of my mind all I could think was, “This girl is nearly a decade younger than me, and she could show me a thing or two!”

This brings me nicely to my problem. She seems very keen to have sex, and in many ways I like the idea myself. The positives are that I would be able to lose my virginity, finally experiencing sex, and the whole experience could increase my confidence if I met someone else, as I wouldn't be worrying about my “first time”. The negatives are that it could go the other way; I may be nervous and not perform. I am worried about not knowing what to do and what positions there are. I am concerned that I may come too early and that I won't actually know how to do it in general! I'm not sure whether porn is a help or a hinderance!

The thing that makes it worse is that because she is a work colleague, if I do anything wrong and she decides to tell people, I'll be the laughing stock of the office. If that happened, I would have to quit my job and emigrate!

So, do I agree to have sex with this girl, even if I don't think I'll necessarily end up in a relationship with her, or do I hang on to my virginity in the hope of sharing my first time with the “right person” that may never come along? Do I gain the experience now while it is being offered to me on a plate, or do I risk facing the humiliation of being a virgin with someone I could potentially end up with if I didn't mess things up by being a virgin?

I know many people will say things like, “being a virgin isn't a big deal”, but it is to me and to almost everyone I have met!

I'm at my wit's end with society's obsession with sex, and the constant burden of virginity.

Please help!

View related questions: at work, confidence, girl at work, porn, shy

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A female reader, Moo's Mum New Zealand +, writes (7 February 2012):

Moo's Mum agony auntI honestly don't think you need to say you are a virgin to anyone even the person you choose to loose it with. Just get on and do it and don't worry about having to admit it to anyone. At the end of the day this is your business and no one else needs to have their nose in it :-)

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A female reader, Miamine United Kingdom +, writes (5 February 2012):

Miamine agony auntI'm not really understanding the big issue about virginity. I don't see many references to waiting until you find a virgin girl in the UK.. America is a very different thing.

At the moment your worrying so much about embarrassment that life and the girls are passing you by. At this rate you'll be an 80year old virgin because you was too scared to even try.

The age of the consent in the UK is 16, so yes, of course it's difficult to find a virgin if that's your intention. At 18 that young woman has been legally allowed to have sex for two years, and like most people didn't have any hangup's about doing that.

Your best bet is to go to church. There's probably 10 women for every man in there. That's where your likely to find a virgin over 18 if any exist. Or just go to a nightclub. In the UK, available women outnumber available men. Ton's of women are searching for a good man, and they can't find you because your stuck at home worrying.

Otherwise, don't even mention it. Find a girl you like and start dating her and then if she's the right one then do the sex thing. There are no signs that men are virgins, they don't bleed like us, and you explain any nervousness by saying your always shy with a new person, or it's been a long time, or you want her so much you just can't be causal about the whole thing.

It's already difficult enough to find love, without worrying about virginity and how to have sex. Pick up a book like "the joy of sex" or go and watch a porn film, that will tell you exactly what goes where. Then go out dating. Your issues over virginity, your obsession is ruining your life whilst the rest of the world is out there having fun.

Sorry, but you are your own worse enemy.

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A female reader, Tisha-1 United States +, writes (5 February 2012):

Tisha-1 agony auntI've been reading a book called "The Power of Now" by Eckhart Tolle. It contains some pretty interesting ideas on how our minds work against us. Sounds like yours is earning double overtime. You have to get beyond your inner tormenter, and I think learning to NOT think will be your best weapon in your current battle.

Time for a leap into being. Good luck.

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A male reader, november_rain United Kingdom +, writes (5 February 2012):

november_rain is verified as being by the original poster of the question

Okay, since this is nearly a month old, I'll leave it at that. Having re-read my last comment, it does appear to tail off into a rant.

I think it just makes me angry that every time I do meet a girl, which isn't often, it turns out she's very sexually experienced and it scares me off because my pride forbids me to admit that I'm a virgin.

I don't think my shame about being a virgin is entirely irrational. If any men out there are reading this, put yourself in my position. You are 27 and a virgin, and you've just met a really hot girl who is very interested. You find out she's had about 3 or 4 sexual partners. How do you deal with it?

I hope this still makes sense to someone!

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A male reader, november_rain United Kingdom +, writes (31 January 2012):

november_rain is verified as being by the original poster of the question

Hi,

I've read through your answer, and I've also searched the archives of this forum. I have found a few interesting points that I can definitely relate to. One person says that it becomes "part of who you are/your identity" if you are an older virgin. I can completely relate to this, although he seems to make out that it could be traumatic to lose your virginity. To be honest, I'd be glad to be rid of it. It's like I am carrying a weight around with me constantly!

I'm not sure that women can tell I lack confidence in every way, because I don't struggle in the slightest to talk to women. My problem is and always has been my lack of ability to ask them out. Over the past 8 years or so, this has also been hindered by my lack of experience, of which I have always felt deeply embarrassed, ashamed and frustrated.

I think you are right to say I am "stuck in my head", but believe me nothing is as simple as it may seem if you have never been in this situation. The reason I am reluctant to take advantage of this particular opportunity is that I am worried word might get out. I also have a sense of pride and telling a young girl of 18 that she is my first is something I just can't do!

Finally, yes I was originally thinking I'd eventually end up in meaningful relationship with someone, but I didn't expect it to take most of my adult life to just find one, when other people seem to just hop from relationship to relationship as though they grow on trees!

I still believe it would be nice to meet someone in the same situation, but I'm not sure this will ever be possible because I truly, genuinely do not believe they are there! I've lost count of the number of times I have found out things that surprised me about girls I have known!

I am giving the dating site option serious consideration, because at least I'm likely to meet someone who is a relative stranger.

My only concern here is, I didn't meet too many girls the last time I tried a dating website. I just wondered, would honesty really be the best policy? Would it not put them off?

I have seen questions on the forum along the lines of "My boyfriend is 30 and a virgin?!?!?!". I can see it entirely from the woman's point of view; who the hell doesn't have sex?!

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A reader, anonymous, writes (26 January 2012):

Ordinarily, I would advise someone with your sort of question (being older and a virgin) that they should just fake their way through it. I wouldn't advocate that they should lie, but they don't have to divulge their status. (If you take a moment to search the archive of questions on the site, you might realize that there are lots of people in your situation...some far older than you.)

There are two sorts of virgins I've met, the kind that are ashamed of their status and the kind that aren't. You happen to be in the former category. From the shear fact that you've managed to keep this thread going for 2 weeks, I'm guessing that you're slightly neurotic about your status and women can sniff out your self-esteem issues even if you can't...and that's what's keeping you where you are,not your "condition". I'm not trying to be harsh, but if you can't find a professional, I think your best bet is find someone in your situation via an online site, which is why I advise you to be upfront and honest in your situation. I'm just not convinced with your anxiety you could manage bluffing your way through the experience.

I don't mean to disrespect you. You sound like a very intelligent and thoughtful person, but from what I see, you are stuck in your head right now and you seem terrified to act on any opportunity that's offered to you. If you were originally saving yourself because you wanted to a have a meaningful relationship with someone before you had sex, I would say being honest via a dating site is your best option. This way you can find someone who is in the similar situation(they are there, no matter what your impression is) and build an honest relationship where you feel secure enough to have sex.

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A female reader, So_Very_Confused United States +, writes (26 January 2012):

So_Very_Confused agony auntwell then for sure you tell them. have some faith in human nature.

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A male reader, november_rain United Kingdom +, writes (26 January 2012):

november_rain is verified as being by the original poster of the question

What if I'm just looking for a bit of fun to help avoid the need to discuss my situation with someone more long-term?

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A female reader, So_Very_Confused United States +, writes (25 January 2012):

So_Very_Confused agony auntNot before you have sex with them.

If you are looking for a long term relationship then you will spend lots of time with them getting to know them BEFORE the sexual conversations come up...

ONCE you are ready to be sexual with them is the time to discuss it.

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A male reader, november_rain United Kingdom +, writes (24 January 2012):

november_rain is verified as being by the original poster of the question

So, you're saying I should tell everyone I meet that I'm a virgin before I can have sex with them? What happened to people not having a right to know your past?

The thing is, I know this will scare off the vast majority of girls! Maybe that means they aren't the "right girl" for me, but the way things are these days, who is going to expect a 27 year old man to be a virgin? Surely it's going to freak them out?!

As for mentioning my situation on a dating site, along with my picture, surely I'm leaving myself open to some serious humiliation! Am I right?

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A reader, anonymous, writes (20 January 2012):

"Basically, I don't ever intend to confess my virginity to anyone, ever. People are absolutely ridiculed over anything like that, and I believe that is potentially more damaging to one's confidence!"

Then prepared to remain a virgin. You are alternately letting your pride and shame get in the way of you having a sexual relationship with anyone. That anon poster wasn't ridiculing you, though you took it that way. I'm sure you would get a lot of responses on a dating site if you were honest about your situation. I for one would be interested in someone who was honest, forthright about their situation, and refreshingly new to the game. I'm sure I'm not the only one.

With all due respect OP, your "virgin" status isn't pathetic but your neurotic obsession and shame about it are. You've gotten a lot of good advice here. Why don't you try some of it out and let us know how it goes rather than go on endlessly about hypothetical situations? No one here can help you if you don't at least try to help yourself.

Good luck.

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A female reader, Tisha-1 United States +, writes (20 January 2012):

Tisha-1 agony auntAre there no professional matchmaker services in the UK? I'm sure you are clever enough to find one, if you put your mind to it. Good luck!

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A male reader, november_rain United Kingdom +, writes (20 January 2012):

november_rain is verified as being by the original poster of the question

To the last anonymous poster,

I am simply going to ignore that.

Tisha-l,

I'm not sure! Although it may very well be the case that I will then worry that I'm only a novice! However, at least I won't have to look her in the eye and say I've NEVER done it, because that would just appear pathetic at my age! I truly believe it would help my confidence in that respect, at least to some degree!

Basically, I don't ever intend to confess my virginity to anyone, ever. People are absolutely ridiculed over anything like that, and I believe that is potentially more damaging to one's confidence!

I do feel I've given you the impression that maybe I never get beyond a first date. Although this is often the case, there have been occasions where I have seen the girl on more than one occasion. What I think tends to happen is, I don't flirt enough, and generally I'm the opposite of what you said. I'm probably not "intense" enough.

I just think that girls leave their first date with me and think, "That was a nice guy. We had a nice chat, but he didn't touch me once/didn't flirt... etc..."

Hope that makes sense! What do you mean by a dating professional? Where would I get hold of such a person?

To the anonymous male,

I can relate to much of what you are saying, or at least understand it!

'My "girlfriend" then dumped me and went back to her ex (she let me know how great the sex with him had been)'

This is exactly the thing I am so worried about! I have had a very, very similar thing happen to me before, although it was only over kissing. I was told how BAD I was at it, and obviously that has led me to believe over the years that if I'm such a bad kisser, I may was well have no penis because I'll be even worse at sex!

I think I do need to try and meet more and more girls, with the sole intention of just sleeping around until I've gained some decent experience. I think the other problem I have there is that I still live with my parents, so there's never really been anywhere to do it anyway!

Once again, thanks to all for your help :)

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A reader, anonymous, writes (19 January 2012):

I suggest that you advertise on a free dating site, such as "Plenty of Fish", along the following lines...

Virgin at 27 and really don't want to be - please can anyone help?! then sit back and watch the offers come rushing in!

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A male reader, anonymous, writes (19 January 2012):

I was in a somewhat similar situation at your age. My opinion is more or less the exact opposite of what others have said. Your last post actually does make perfect sense to me.

Just focus on getting laid as much as you can. Don't worry too much about whether or not the woman is enjoying it the first few times. You are probably going to be bad at sex at first. I know this is going to sound horrible, but you need to find some women to practice with. It's actually better if it's someone you know you aren't going to want to be with long term because it will be easier to deal with if it doesn't work out long term (and it probably won't).

Don't worry about whether you work with her, if she's really your type, if you're actually very attracted to her, etc. It really doesn't matter. You need practice.

The first time I had sex I was older than you are. I lasted all of about 5 seconds, and that was after several failed attempts to have sex when I couldn't get it up because I was so worried about it. My "girlfriend" then dumped me and went back to her ex (she let me know how great the sex with him had been)

I spent a lot of time trying to get up the nerve to get back in the saddle again, so to speak. After quite a bit of trial and error I eventually got over most of my insecurities. But, I sure wasted a lot of time analyzing the situation. You've got to get out on the field and get some practice. Nobody walks out and throws a winning touchdown their first time out.

My advice is, when in doubt, be very affectionate, and lick her a lot. Try sucking on various things, but pay attention to how she reacts. Unless she is quite self-conscious (quite a few women are, and that's understandable)(women are only human as well) You really can't go wrong with lots of licking and sucking.

Now, get out there soldier and start licking and sucking!

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A female reader, Tisha-1 United States +, writes (19 January 2012):

Tisha-1 agony auntIt is easy if you keep trying. Sounds like you gave up a long time ago, because your thoughts keep going back to "I'm a virgin! She won't want to be with a virgin! She's not a virgin! She can't be a virgin! She's going to JUDGE ME!" And then the whole thing disintegrates.

So you lose your virginity, somehow. Will that magical clear up those thoughts, or will your brain pick a new thing to worry about? "I've only had one sexual experience! I'm a novice! She won't want to be with novice! She's not a novice! She can't be a novice! She's going to JUDGE ME!"

That's kind of the vibe you're giving off.

Work on just getting past the first date. I expect you put them off because you are a bit intense. Maybe you have a tic you're not aware of. Who knows? You need some feedback on this.

I'd spend the money on a life coach or a matchmaker. Tell her (preferably a her) what the deal is and get some honest feedback from a dating professional. We can't do this from our vantage point, but my guess is that you scare the women off due to some awkwardness or intensity that's not proportional to the situation. Go ask someone who can observe you and give you real honest feedback.

That's all I've got for you. Good luck.

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A male reader, november_rain United Kingdom +, writes (19 January 2012):

november_rain is verified as being by the original poster of the question

You make it seem easy, but it never feels it though! I'm not saying that I've never asked anyone out ever, and that's certainly something that I can work on given the opportunity.

The question is, if I meet someone, will it matter that I'm an 27 year old virgin? Some say it would, others say it wouldn't! I have drawn the conclusion that since it's nigh on impossible to find even a 16 year old virgin, I probably don't even live within 30 miles of a 27 year old virgin!

I don't think I'm going to find anyone to have a serious relationship with any time soon, and since I've had absolutely no sexual experience at this time in my life, I feel the only way is to have sex a couple of times so that when the time DOES come, I'm not going to be a complete loser in bed!

Hope that makes some kind of sense!

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A female reader, Tisha-1 United States +, writes (17 January 2012):

Tisha-1 agony aunt"I've enjoyed chatting with you very much. I'd like to get to know you better. Would you like to go out, for a cup of coffee? May I have your number?"

Can you manage that?

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A male reader, november_rain United Kingdom +, writes (17 January 2012):

november_rain is verified as being by the original poster of the question

Ciar,

Firstly, maybe I am over-thinking it, but that's why I'm here! I can't seem to do anything BUT think about it! That is not to say that I spend all of my free time on the internet typing away! As a matter of fact, I do try to spend as much of my free time as I can going out.

Secondly, I didn't say there was more than one film! I had to go and watch that at the cinema with my friends. I had to sit there basically laughing at myself!

I'm not trying to be rude or to offend, but try being in my position without being worried sick about it!

Tisha-1,

When you say social anxiety disorder, what exactly do you mean? What I'm saying is, I don't find it difficult to make friends, or to talk to anyone. In fact, I can be chatting away with a complete stranger, male or female, within minutes of meeting them. Not only that, I have flirted with girls before, but it's never really led to anything.

It's all very well saying I need to deal with it, but how?!

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A female reader, Tisha-1 United States +, writes (17 January 2012):

Tisha-1 agony aunt"I'm stuck between my morals and my penis." No, actually, you are trapped by your own shyness and social anxiety disorder. Deal with that first. The rest will follow.

Instead of analyzing how to lose your virginity, analyze how to lose the social paralysis. That would stand you in better stead.

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A female reader, Ciar Canada + , writes (17 January 2012):

Ciar agony auntThe way you think is not the issue. It's the volume of time spent doing it. You're over thinking it.

ONE film about a 40 year old virgin. ONE.

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A male reader, november_rain United Kingdom +, writes (17 January 2012):

november_rain is verified as being by the original poster of the question

Ciar,

Whilst I agree with you that I have looked at this from every possible angle and need to be "getting out there" more than I am, I must disagree with you on a couple of things:

Firstly, this has not devolved from a genuine interest. I was initially interested because I thought I may have met someone who wouldn't have any experience, therefore would not have been expecting much. I think it would be nice to meet someone like that, but I realise now that if a fairly quiet 18 year old girl has been sleeping around, there's no chance! My issue was whether I should go ahead and have some fun, or do I do the right thing and leave her alone?

Secondly, you say "the vast majority do not care a fig about" virginity. I don't know what it's like where you come from, but it's certainly made a big deal of here and in America. Why else would there be a film called "The 40 Year Old Virgin"?

It's all very well for people who probably lost their virginity in their teens, or at the latest their early twenties, to say that people don't care, or to "hire a pro", but I bet you didn't have to!

Ask yourself how you would feel about yourself now if you had done that. Would you tell your first sexual partner? Would you be ashamed?

Also, I have only spent a small amount of time on this site, and have been out at least five times since I began this thread. Admittedly, in that time I have met nobody, but at least I'm trying to be out and about!

Quite frankly, I find it very annoying to be told that the reason I'm a virgin is becoming more and more evident. As you say, it is a big step and deserves consideration. I really cannot help the way I think; I really wish I could!

I am still very shy about approaching women and have never even properly asked a girl out! I have spent hours flirting with girls only to end up saying goodbye without making a date, because something, I don't know what, stops me. Maybe it's stupid pride; that I think I might be giving something away in even asking. I have been trying to overcome this but there's only so much practice I can get meeting two or three girls a year!

All I want is to meet someone and for them to take me as I am! Why is that too much to ask?!

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A female reader, Ciar Canada + , writes (16 January 2012):

Ciar agony auntI appreciate that this is a big step for you and it deserves serious consideration, but the reason you remain a virgin is becoming more and more evident the longer this thread continues.

The time you spend here, typing, analysing, turning it over and studying it from every angle is time you're not spending in the field, so to speak.

This post has devolved from you having a genuine interest in this girl to talk of just getting the job done to rid yourself of your virginity (which frankly, the vast majority of people do not care a fig about).

You have already studied this issue from every angle before coming here and I don't think you are going to glean one more pearl of wisdom.

My advice is to leave your colleague alone and hire a pro. That way an innocent person won't be used and hurt and you can finally, pardon the pun, put this matter to bed.

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A male reader, november_rain United Kingdom +, writes (16 January 2012):

november_rain is verified as being by the original poster of the question

That's kind of it. I can't see it going anywhere and feel that it's almost stupid to let an opportunity to lose my virginity, something that has been bothering me since I was 19, pass me by! It's not just that I don't see it going anywhere; I think things could be very tricky if word got out I was a virgin. I just hope that I really am being “outrageously paranoid”! I know people can tell. In fact, people have actually told me they can tell I'm a virgin, which as you can imagine was a real boost for my confidence!

If I could finally say to myself that I'm not a virgin, then that would be great! A little fun would also be great if I could find someone who I trusted a little more, or who was distanced from my work and social life entirely. I don't feel pressured by this girl in any way, but I just feel that I should have made a start on all of this years ago so that by now I would be comfortable to just do it.

I have no idea whether she thinks this is going somewhere, but she has said something along the lines that she doesn't like guys who sleep with her and then disappear off the scene. That's what made me realise she had been sleeping around a lot already.

I think whether or not I wait for this mythical “special person” boils down to whether I'm going to meet a girl who is a virgin. Obviously it would be fantastic if I did, but how likely is that, given my age and the fact that girls ten years younger than me are doing it? Not very I wouldn't have thought!

Whilst I'm fully aware that I probably shouldn't have sex just for the sake of having sex, surely losing my virginity is something I'll need to have done as a bare minimum in order to build any kind of sexual relationship with a potential future partner expecting a good time in bed!

I am extremely worried about getting older and still being a virgin. I was worried when I was 19, and as the years have gone by it's just got worse and worse. Just over three years ago I got absolutely sick of it and I posted a question on this site. A couple of months later I joined a dating site and met a couple of girls but never got past the first date, which just added to my frustration.

I think you have a point about the number of people I've met; it's not many, but I just can't approach girls in clubs or bars like most guys can. If my friends are with me it's worse, because I don't want them to see me fail. I wouldn't go out on the pull on my own, so I generally end up relying on someone else in the group to do all of the work, which can't look good! I'm not sure where I go from there at the moment, but I'll need to try something soon or I'll go mad!

As you say, I'm stuck between my morals and my penis, at least to a degree! However I think the morals will just have to be abandoned to be honest. Morals are only any use when they match everyone else's!

Thanks for the reply; it was much appreciated. I think you've managed to sum up my situation pretty well! I know I need to try and meet more people, and “play the field”, but it just feels like my years of shyness towards girls have resulted in the field being very sparse!

I know I seem to end my messages on a negative note, but like I say I seem to have an answer to everything! To avoid this answer taking on another negative tone, I'd like to take this opportunity to thank everyone who has contributed with answers to my question so far.

Cheers :)

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A male reader, MrMcLovin United Kingdom +, writes (13 January 2012):

Ah I understand; so you don't want it to seem like you're just going to use her for sex because although you want sex with her, you already can't see it going anywhere...

Tricky. I understand that you obviously just want to have sex so you can say to yourself you're not a virgin but don't feel pressured. To be honest though, you're both adults and there's no harm in a little bit of fun I guess.

On the other hand, if she is under the impression that you and her are going somewhere then it could be seen as you misleading he.

I know when people are younger, like me, they imagine their first time as being "special" but you're a lot older now. So you have to decide whether you still want to wait for this special person...If so, don't have sex with her if you're not ready for a relationship with her.

IMHO, you shouldn't have sex just for the sake of having sex. And I believe this desperation(sorry if it's not the right word) for sex will push you to doing exactly that.

Maybe if you are worried about getting older and still being a virgin you should ask yourself about how many people you've met up to now. If the answer's not many then it's up to you to change it. Go out, meet people etc. People say the right person will come along; it's a cliche. The right person WILL come along, but you have to FIND them first to KNOW that they are the right person.

That's just my perspective, some of this might have already been said but since you commented back I thought I'd reply. You seem like an honest guy who is stuck between his morals and his penis!

Good luck mate,

MrMcLovin

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A male reader, november_rain United Kingdom +, writes (13 January 2012):

november_rain is verified as being by the original poster of the question

No, you haven't offended me at all! I sometimes need people to be frank in order to get across their message. I am one of these people who annoys people because I "have an answer to everything". It's not deliberate; these are genuinely the result of my thought processes following any advice.

Part of my problem is that, as someone mentioned, this girl is convenient. I like her in a lot of ways, but we are completely different types of people and I can't see it working in the long run. This and the fact that she has been having sex for a while and I haven't even started makes me all the more uncomfortable.

In many ways I'd like to go for it just because I can, as I have never even had the opportunity to have sex before, let alone having it offered to me on a plate!

The way I see it is I either go for it and risk people finding out (unlikely as long as she keeps up her policy of not telling anyone anything), or I don't go for it and risk waiting another year, two years or even ten years before another opportunity presents itself!

Thanks to everyone who has answered; I have taken it all onboard and it is all useful information. It's still going to be very difficult but hopefully something will happen soon!

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A male reader, MrMcLovin United Kingdom +, writes (11 January 2012):

I hope I didn't offend you, I just read my answer and it sounded a bit cold ;) But I know what you mean. To be honest, i doubt any girl will expect you to be a sex god or anything. I still think the best thing you can do it tell the girl and maybe explain you're a bit nervous; or that you're eager to get going haha ;)

My advice would be to not panic and rush it, foreplay and such to get in the mood. You probably won't even be thinking about your lack of experience once you get going. I'm sure your girl will help you out if you get stuck ;) Just enjoy it and stop worrying!

Good luck

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A reader, anonymous, writes (11 January 2012):

"so my questions was, do I take the chance I am being offered here, or do I run and just hope for the best some time in the future, which may never come?"

You have already got some very good advice and different perspectives on this very question. I think you are navel gazing now. You are wringing your hands and worrying about worst-case scenarios so you avoid approaching your actual problem, which is your sense of shame about your virginity. I have to say that it is your sense of shame which you are tripping over at the moment.

I know men in their 30s who are virgins. I know they are virgins, not because they have told me but how they react to any type of intimacy. They are skittish around women and they can't settle on anyone to date(even the people they like) because they feel they will get their first moment "wrong." No one is good enough for them. Stop being ashamed...you project it on to your potential partners. The problem is in your perspective, not in some "vicious cycle" that you believe other people create.

And as for your worst fear of an 18 year old girl going around telling people how bad you were in bed and condemning you to a life of celibacy...sorry to say it, but you are being outrageously paranoid. I've only once in my life heard of a girl putting down a man she had a sexual encounter with...and she was a 26 year old "technical" virgin (did everything but intercourse). She had no perspective on the issue, so she was an eternal critic. And I think you are in the same position regarding your life. I and most other women discounted her and her stories as merely self-promotion and immature narcissism. We thought her kiss-and-tell was very bad taste. Really...what women is going to listen to an 18 year old girl to determine if a guy is going to be any good in bed or not?

How many 18 year old's do you know that have discerning and taste in clothing or food? Do you truly expect them to have a developed taste in sex? Lighten up! Given your professional situation, this is not the girl for you, but there will be others. The nice thing about losing your virginity is that you have no expectations. If you approach it calmly and without shame, you can be better than any porn star because you AREN'T performing...you are just listening to your body and your parnter's...

Whenever it happens, have fun.

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A male reader, DoubleM United States +, writes (11 January 2012):

DoubleM agony auntMost guys in their teens and twenties are lousy at sex. The poor girls don't even know what they're missing until they get with an experienced man. Most young guys only care about getting their jollies, and if the girl enjoys it, then so be it. I'll admit that I was much the same in my youth. So don't fret so damn much about this obsession of yours. Get laid, dude! The planet will keep spinning.

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A male reader, november_rain United Kingdom +, writes (11 January 2012):

november_rain is verified as being by the original poster of the question

Maybe I should provide some clarification as to what I meant by "You need sex to get a girl". I simply meant that if you want just want sex, but you've never had it at my age, it's very difficult because girls will expect a level of experience befitting to someone of that age.

I think it is fair to say that I am in a very, very small minority as it is. Almost everyone is having sex these days, and I feel that I've been left behind.

The only conclusion that I seem to be able to draw is that I give up on getting some "sex practice" and carry on as before, in the hope that maybe one day I will meet someone who is "right for me", and that they will either be a virgin or I will "just know" that she will be understanding enough that I can trust her with the fact that I'm a virgin.

I think that anyone who gets to my age "cares". Unless you're doing it for religious reasons or something, it's not seen as normal. Believe me, if you do get to my age and are still a virgin, you will care.

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A male reader, MrMcLovin United Kingdom +, writes (10 January 2012):

"You need sex to get a girl"

That's the most stupid thing i've ever heard. I'm a virgin, but i'm still quite young. I'm not worried about anything. If I get to your age still being a virgin I won't care...

It doesn't define you.

I think you may be expecting to completely change once you've had sex and that once you've had it some divine intervention will help you pick up girls. It's not true.

Oh and with regards to you being humiliated. If she is not sensitive enough to take it and support you then she's not worth the effort mate.

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A male reader, november_rain United Kingdom +, writes (10 January 2012):

november_rain is verified as being by the original poster of the question

Maybe I am being stupid, but it's also easy to say that when you aren't in this situation, and probably never have been. The fact is, I don't want to remain a virgin, but I could never tell anyone that I was. The reason being, people are going to find out. Let's be honest; rightly or wrongly, there is a huge stigma attached to being a virgin. Sharing that information with anyone is potentially dangerous, but not sharing it could be just as bad.

I don't want to appear negative, but it is almost certain that any girl I meet will have had sex. Because of my lack of experience, it seems I will have to be especially careful who I choose to have sex with, as they may be the "kiss and tell type" mentioned earlier and start telling everyone how rubbish and inexperienced I was.

This narrows down my options, so my questions was, do I take the chance I am being offered here, or do I run and just hope for the best some time in the future, which may never come?

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A male reader, Hugh.J United Kingdom +, writes (10 January 2012):

Hugh.J agony auntYou ARE being stupid!

A former colleague of mine married a man much older the her, aged 68, and he was a virgin until their wedding night! Apparently, it didn't take him long to learn......

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A male reader, november_rain United Kingdom +, writes (10 January 2012):

november_rain is verified as being by the original poster of the question

First of all, many thanks to all those who took the time to answer my question. I really wasn't expecting any replies so quickly! I have taken the time to read all of the comments and just have a few follow-up questions if that's OK.

I must say, I always wonder whether I have "stuck to my guns" waiting for the right girl, or whether I have simply hidden behind this reason as I have been too afraid to do anything else!

Now while I don't think this girl is the kiss-and-tell type, I do agree that the professional issue comes first. The thing that really worries me is that if we fell out, she may broadcast how bad and inexperienced I was. If that happened, I really don't know what I would do.

From things she has said I understand entirely what you are saying regarding sex being regarded as the beginning of a relationship. However, one thing that I am not prepared to share with her or anyone else is the fact that I am a virgin. I am deeply, deeply ashamed that I have never had sex and I couldn't put myself through the humiliation of telling one person, let alone other people finding out!

As for whether the age gap and her experience is "part of the attraction", it is the complete opposite! I did hope that maybe she was a virgin but this turned out not to be the case. I think if she had been, I would not be asking this question because at least she wouldn't be expecting too much.

It's all very well to say my "time will come", but I am twenty seven years old. I feel increasing anxiety as the years go on that my life is passing me by. I see the younger generations starting to explore sex and I wonder whether my time will in fact ever come.

While it is nice to hear from the anonymous young lady that there is still the occasional virgin out there, I genuinely believe that the chances of meeting anyone in my age group who is still a virgin are next to non-existant. Even the younger girls such as this one will all be expecting some level of experience which I cannot provide.

I hope someone can tell me I'm being stupid, but I have a feeling that I'm stuck in a vicious circle where you need sex to get a girl, but you need a girl to get sex.

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A male reader, MrMcLovin United Kingdom +, writes (8 January 2012):

Look. The whole problem you are describing about not knowing what to do and "not performing" will apply to ANY girl that you eventually lose your virginity with.

IMHO you are in a great position. If she seems like a sensitive and nice girl then talk to her about it and be honest about your feelings. She might even like it, kinky ehhh ;) Tell her you're all hers haha!

Stop worrying, it'll be fun, you are a very lucky man, sir.

MrMcLovin

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A male reader, DoubleM United States +, writes (8 January 2012):

DoubleM agony auntMost every guy has "fear of rejection" to some degree. The key is to not give a damn. Just learn to forget about it and move on.

Your decision to have sex with the girl, or not, is another problem, but also a possible "solution" to your virginity obsession. First, it should not be such an obsession. It's ok. Your time will come. Workplace issues here may be the problem, but I was always adventurous in my youth and rarely turned down an opportunity.

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A female reader, anonymous, writes (8 January 2012):

Not everybody is sleeping around. I am 27 and a virgin. I know several people my age who are also virgins.

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A female reader, Ciar Canada + , writes (8 January 2012):

Ciar agony auntHer age, the fact that she is a work colleague and you haven't known her very long make her a pretty big risk and I suggest you either take a pass, or take it very, very slowly and really get to know her.

That's not to say that all office romances fail. In fact many of them have been successful. And she may turn out to be a great person, but it is just too soon to say.

She is not obliged to provide you with details of her sexual history, but her vague reference to 'a few' past lovers and her concern about your reaction to it lead me to suspect she may have understated her experience. I'm not suggesting she is or was promiscuous, simply that she may be more experienced than she is comfortable admitting at this point. I've read far to many posts from far too many men that I'd be remiss in not giving you a heads up.

The longer you're with this girl the more invested you will become and the more her experience and your lack of it will matter. I say this not because it's that way for everyone, but it is so for many and you've already expressed some concerns about it.

As far as first time jitters, it would help you greatly (and whatever partner you lose your virginity to) if you had a more informed and realistic set of expectations. It is VERY common for men to climax quickly, especially on their first attempt or after a long haitus from sex (women too, but it's less obvious for us). One of the benefits of sex is you get to do it again and again. If you treat it as so big deal you're partner will too and it would help her enjoy the encounter more if she didn't have to keep reassuring you. There are plenty of books and online articles you can turn to. Make your scenario open ended instead of trying to stick to a script.

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A reader, anonymous, writes (8 January 2012):

I don't think having sex with her this is a good idea for a couple reasons.

The professional issue is the first and the most important one in my opinion. People will find out...they always do.

This is also an issue: "she isn't really the type of girl that I would normally consider dating." I understand that perhaps you feel holding out for the "right" person is naive, but you don't seem to feel much for this girl...in fact you seem interested in her because she's merely convenient. Personally, I also think that holding out for the perfect person is a little naive, but I think you could do better. You could at least have sex with someone you felt something for.

If part of your attraction is “This girl is nearly a decade younger than me, and she could show me a thing or two!" then be prepared for disillusionment. If you do have sex with her, be prepared for her to think that you do want a relationship and that the loss of your virginity was the beginning of a relationship. Most people, and especially women at her age tend to interpret sex as an indicator of the relationship. If you can't tell her to her face to face that you don't want a relationship with her after the fact, then don't have sex with her.

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A male reader, Hugh.J United Kingdom +, writes (8 January 2012):

Hugh.J agony auntYour work situation is what makes this difficult. Because of that, I wouldn't go there unless you can be sure, really sure, that she isn't a kiss-and-tell type.

Not an ideal solution, but you could gain experience with a "working girl", who would treat you well, show you what to do, take your money and say goodbye!

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A female reader, Moo's Mum New Zealand +, writes (8 January 2012):

Moo's Mum agony auntI don't understand people who hassle virgins! Yay you well done for sticking to your guns and waiting for the right girl. My suggestion is to go to the library and get "The Joy of Sex" and some other such books and read up a storm. When the night comes round take it slowly and enjoy yourself. Girls like slow and gentle sex that escalates as it goes on. You will be fine enjoy and remember those condoms.

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