That was me just 1 year ago. I am actually no longer a virgin at 31, but I feel as though I got extremely lucky. It happened with a friend of mine who is an older woman and very open sexually. Threesomes, foursomes, and just about every kink you can imagine--she's tried it all. She lives a polyamorous lifestyle. I had known her for more than a year, and was very attracted to her, but have always been extremely shy for as long as I can remember.

I was also raised in a fundamentalist religious environment and after years of questioning I changed my mind about it and finally "came out" as an atheist about 3 years ago. I used to believe in "no sex before marriage", but I've changed my mind about that as well.

So after knowing her for more than a year, I finally worked up the courage to ask her out. She accepted and we had a lengthy email conversation shortly thereafter where I asked her if she was attracted to me and if she had ever fantasized about me and the conversation quickly turned naughty! I also confessed that I was still a virgin and she said she wasn't surprised (she knows about my religious fundamentalist past). The date turned into dinner at her place and after that we had sex and I spent the night.

But it ended almost as quickly as it had begun. I was very nervous that first time and got performance anxiety, and she told me afterward that she was concerned that I still felt some guilt over sex, like by having unmarried sex I was being a "bad person". I assured her I didn't feel this way, but she still felt weird about it and wanted to give it "time off", so I waited a month.

After a month, she told me that she has another reason she doesn't want to sleep with me again, which is that she's afraid I'll get too "clingy" if she's my only option and that she wants me to put myself out there and lay a few other chicks first before she'll consider having sex again with me.

So my one option quickly went back to being not an option and it looks like I'm back to square one. I would like to learn how to actually "go out there and hookup with other women", not even so much to get laid with my first again (I honestly don't think she's a good long term match for me anyway), but just to do what it was I was wanting to do in the first place--which was to go from a life that does not contain sex to one that does. Just losing my virginity does not mean I'm satisfied now and no longer want sex. In fact quite the opposite! Now that I know it's possible to get laid even for a shy, nerdy, awkward around women and very sexually inexperienced guy like myself, I'd really like to repeat the experience!

But I have no idea how. I feel like I got extremely lucky with the woman who was my first and it's unlikely a situation like that is going to happen again. I need to figure out how to consistently attract women and have something approaching a normal sex life.

Hello, Cogito.

Well, you are in the right place to start your transformation.

I would recommend to start with some David DeAngelo material, especially if you're new to this whole thing. You don't have to become a pickup artist to improve your love life. So, I recommend reading "Double Your Dating" ebook just to get you started. You will have to work a lot on your inner game, in the way you see yourself, and that can be difficult sometimes, especially if you feel like a nerd. You will have to change your self image and find the confidence to go out and do stuff. You have to know you can do this, just introduce some changes to your lifestyle, one step at a time. Start by changing your image, your style. Choose a style that is congruent with your personality, but is modern and not nerdy. Change your body language so that it reflects confidence. This is easier said than done, but as you improve your self confidence, it will become easier and easier. I also recommend Paul McKenna's program "Extreme self confidence" or something like this, google it. The important thing is you had your first experience and want to get this area of your life handled. You will find manny tips on where and how to meet women and approach them in the DeAngelo material and also how to get your inner game handled. Think about enrolling in some sort of a class or find other ways for meeting women during the day time if you're uncomfortable with the night scene and feel awkward in clubs and so forth. You will find many exercises to deal with approach anxiety and stuff like that. I think the most important thing is to just work on yourself, don't just fall in love with the first girl you have courage to talk to, but really try to get to the point you're comfortable with who you are and comfortable with talking to women. Then you can really start improving your game with all the different sort of material.
I had a friend who was somewhat awkward with women and he made a great transformation so I know it can be done.
I hope this helps and do let us know about your progress. If you need more info, you can PM me.

Good luck!