I'm a 23 year old megavirgin (to be explained later) seeking some female opinions on my situation as well as advice on how to proceed forwards to better myself and get out of this situation.

But before we get to that, I think a bit of background information is necessary:

I am a 23 year old male and I am a megavirgin. By that I mean that I have no experience with women whatsoever: in addition to never having slept with one, I've also never kissed, never dated, held hands, flirted or anything like that. I am pretty sure that it is physically impossible to have done less with a women than what I've done. Aside from that I don't have any physical deformities or anything of that sort, I'm tall and quite muscular (I compete in weightlifting) with perhaps an average face and have a good job (I'd say my income is in the top 10-15% of people my age).

How did it come to this?
I have always been a bit of a loner, don't really have many friends and those I do have I am not too close to (including some geographical reasons which I will get to later). In high school I was never very social, I think I attended like 3-5 parties during my studying. I was never really invited to anything and to be honest I didn't make much effort to do something social either. So when everyone else was laying the groundwork for social skills and relationship experience I was sitting at home.
When I got to university, the same stuff basically continued. I never really made much effort to be social and hence didn't make many friends or go out much.

Now when it comes to dating/relationships/sex I feel like the guy who turns up to a class in the middle of the semester to find that he's hopelessly behind everyone else in terms knowledge and experience.

I've always felt a little uncomfortable in loud crowded places such as pubs. I don't drink and hence I feel a bit out of place. However more importantly I find that I lack the social skills necessary to talk to people in an informal setting (in a workplace environment I am usually the guy who is leading the discussion/group and who speaks out a lot). It gets especially difficult when I'm talking to girls and I find that I am absolutely unable to do anything flirty/seductive, I believe this is called love shyness and I have it 100%. I am amazed by how easily most other guys seem to be able to handle interacting with women so its no surprise to me that if I am an unskilled conversational partner then girls will lose interest after a while.

I recently started a graduate job in a new city with a leading global firm and I'm also studying towards becoming a chartered accountant (it may sound boring so some people but this is what I'm good at and CAs have some of the best salaries out there). This means that I currently have almost no social circle in this new city but I'm trying to make more friends among my coworkers. Though my firm does have a lot of socials which should provide all sorts of opportunities, the male to female ratio isn't favorable and I'm not sure about how good of an idea it is to try to dip my pen in the company's ink.

Anyway my questions are these:

1) For women: is there any age that you'd consider a "cut off" point for a guy in regards to having at least some kind of experience with women? By this I mean that after that age you'd rather avoid someone like them due to their lack of experience and would just like someone who knows at least the basics of relationships/dating/sex?

2) What are some good dating/talking to girls/socializing audio books to get? I've recently been listening to the works of Carlos Xuma and I've found them really helpful, I've learned a lot from them. What other good ones are out there?

3) I've been toying in my head with the idea of going to a speed dating event. Would anyone recommend this as an option to try out (if not for anything else, then just for the sake of a new interesting experience) for someone in my situation?

4) Are dating coaches any good? I'm considering trying one out, is this recommended or can I find a better use for my money? (and don't say escort, I'm not that desperate)

From the sound of things - you're well educated, intelligent, great communicator, young, ambitious, hardworking, honest, not paralysed or diagnosed with a terminal illness, and you also mention that you're tall and muscular with a career in the global financial sector - you'll be more than fine.
Answers Q1. No, women prefer meaningful relationships over experience; Q2. Anthony Robbins; Q3 Unsure, never tried; Q4 YouTube - coaching tips.
Cheers

My suggestion is to work on making friends before even thinking about losing your virginity.

Since you admit to having a small group a friends

That question can't be answered because it depends on the woman.
Don't know of any books. Just useful quotes. "Stay out of your comfort zone" and "You miss 100% of the shots you don't take". Those two quotes helped me gain a lot of experience.
Do it! You got nothing to lose.
The term "dating coach" reminds me of The Pick Up Artist (http://en.wikipedia.org/wiki/The_Pickup_Artist_(TV_series)). Personally, I'd recommend against a dating coach because 1) they're probably expensive and 2) they're likely going to tell you stuff you already know, specifically "relax" and "be yourself". On every date where I was relaxed, the date progressed into a relationship.

When I was a youngish woman, I fell head over heels for a shy, inept, bumbling pale nerd who never came out from behind his computer (before PCs) except to go out for food at to a.m. Why? Who knows? I was older and experienced and attractive enough. There was 'something about him.' A touch of willingness to be friendly even though I could see he was shy. I met him when he bought something from me in a store I was working in.

He was such a virgin he even held my hand funny when we started holding hands as we walked - he kind of held it up in the air like we were about to do a minuet. Didn't bother me in the least.

I don't see a need for books, courses, or coaches. Get out of the house, just a tiny friendly chat with everyone you meet, that's all there is to it. Nothing fake, and it doesn't matter if you stumble over words or get tongue tied.
Probability takes over.

I met the guy who would end up as my husband when we were college students at two different colleges and worked together part time during the dinner hour at a Y cafeteria. His serving vegetables in little bowls and my serving beverages and desserts around the corner of the steam table from him led to marriage.

No, you don't need a coach or books or special instructions. Volunteer at a library or nursing home or animal shelter or hospital just to get yourself out there to meet and talk to people of all ages. My megavirgin son joined a church and eventually found dates. And like one of our experts says, date 'em all, tall and skinny, short and chubby.

I was a virgin till 22, then I met a woman called Birgit, who was always interested in bad boys (you know what I mean, and how she got interested in me , a geologist, is a question I myself can't answer) - she loved me.

This relationship did not take off because of my faults, I was still in shock from another broken LDR, and could not focus on her.

Besides that one woman, I never met a single woman PERSONALLY, who means what she says. That being said, the bottom line is:

q1. If the target woman that you arre asking tells you that she had no cut off edge / has a cut off edge, that is no guarantee that she will act on this information. Instead, suggestion is you actually DO casually talk to some (preferably elder, mature) woman, and show them your humorous side. If they are to open up, they will open up, and tell you about there preferences. I know that this does not directly address your question, but you will see what they ACTUALLY hold for ideas about age.

q2. I can't answer this question

q3. Although you have nothing to lose, consider this: is losing the virginity your only question, or do you want a meaningful relationship. If you want the second, then also figure out how honest you are about your thoughts. I met a lot of people who will say "yes i am with you", and then on the first sign of hard life, they run away. I know this also does not directly address your question, but think about it.

q4. Dating 'em all is not an acceptable solution, as Tesla said: Edison could have saved a lot of experiment with a little fore-thought. So yes, assess your targets, then find out if any of them are available. Where I am , all the bachelor students are married... I hope your case is not that hard.

I love your word... "megavirgin." That is sweet! That's what I am. I call myself "extra virgin," like the olive oil. I'm 39. Female. Never dated, kissed, had a boyfriend, cuddled, none of it. I have hugged, though. I'll tell you what I told someone else on another board... it'll happen when it happens. :) I wish I knew more virgins my age in real life. Maybe I wouldn't feel like such an outsider then. :( Take care!