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Alright, I've got a problem which is causing me a lot of psychological stress. I've been recently dating a girl, we are both 30 years old, and things are going real good, I like her a lot and I feel she likes me back as much if not more so... The thing that gets to me is that she has had an incredibly wild past: worked as a stripper, dated and had sex with many men, appeared on online pay-per-view sex shows, has filmed herself with past lovers, is unafraid to show her body in public, is willing to have group sex and HAS done it before, has been caught in public a few times, has tried almost every type of drug there is... you see the genre...

She HAS had a difficult background, seperated parents, attempted and "successful" rape, moved from one continent to the other, etc... She's an incredibly smart girl, don't get any wrong ideas, she's is really incredibly bright, but very intense in her lifestyle...

I on the other hand come from a stable background and have gone through my childhood and adolescent years with a strong case of pathological shyness... It took YEARS to overcome it and unfortunately, I know there still remains some trauma deep within. This might all seem weird, but I know that, ever since I was a child, I've always been fascinated with the baser instincts of humans, but was never capable of actually freeing myself of scruples and just going along with it, trying, experimenting... I get the feeling that she has led a much "richer" (according to my standards) life than I have and I feel completely inferior to her in that sense... I feel like I've missed out on a bunch of mistakes, experiments, freedom and complete abandon. I feel like I've a scientific experiment raised in a controlled environment.

I HAVE experimented some things, I've done things she's never done before (foursome and that's pretty much it), but the quantity and quality are nothing in comparison to what she has went through. I often find myself comparing her life and mine and although I do not want to let it show too much, it's eating me alive deep inside... I'm happy with her, but at the same time, I am afraid and feel like a "mamma's boy". She's introduced me to countless things I;ve always wanted to do, but never had the chance, either through refusing to do them out of shyness or having my fantasies rejected by my former girlfriends/wife...

I seriously don't know what to do about these overwhelming feelings. Not a day goes by where I don't discover something new and completely over-the-top that she has went through in her life (she is actually one year younger which makes me feel like I haven't taken advantage of my lead start!). It's ridiculous... Sure, I realize there's absolutely nothing I can do about this, the past is the past, what's done is done... but I can't help feeling bad inside everytime I think back to what she has done (and what I haven't done) and I'm afraid it'll become too much for me to handle one day. I know I should just be enjoying the moment and feeling lucky that she is now mine and I truly feel loved by her. I have pushed away the idea of a relationship with her for the longest time and it's only recently gotten serious... but I really can't bare going through these envious stages on such a regular basis without going completely nuts..

I feel like I've missed out on so much... I love her, but I feel that engaging myself in a new relationship so soon after my last one (which lasted almost ten years - yeah I know, that's when I missed out on everything) is preventing me from really going wild, screwing around, taking risks, being dumb, having fun and enjoying every minute of life, guilt-free... That is basically what I envy the most about her... So I don't know what to do. I think she knows that part of my insecurities with her have to do with this, but I've never really confrontated her with all the details as I have here... I don't want to lose her, but to do that, I REALLY need help to cope with this and maybe some tips on how to resolve this situation.

I know she won't let me see other people unless she can, and I know she doesn't want me to see other people (she IS jealous of other women with me). Regardless of her past, she seems to have a WAY more down-to-earth outlook on life than I do... I really need help here, writing this feels like a ton of bricks weighing down on my heart and my emotions are absolutely out of control.

Please... help... anybody...

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I am 28 years old. I have lived the wild lifestyle and pushed the limits as much as I could. To tell the truth, I'm lucky to be alive. As attractive as the unknown can be, I'll tell you right now, you didn't miss anything good. There is an incredibly empty feeling associated with that lifestyle. It is difficult to have any one true friend. I spent over 10 years looking for something and had no idea what it was. Long story short, I just wasn't happy with myself. Again, you missed nothing. I'll admit that the experiences made me wiser, but I may have been better off remaining ignorant to more than half. I have no regrets, as I feel I have turned out quite alright.. but I think you get the point.

You are older and wiser now. To try to go back and live that way would be alot like going back in time and hanging with the 'cool' kids, throwing rocks at cars.

Lets talk about ego and self control.

It can be tough for guys to have a girlfriend with more sexual experiences than them. This is natural. The male ego will not accept it without a fight. It hurts our sense of pride and turns us into emotional wrecks. Thank goodness for our higher brain functions. You say in your post 'Sure, I realize there's absolutely nothing I can do about this, the past is the past, what's done is done...', and you are right!

Whenever you feel bad/inadequate when you think about her adventures, practice self control and remind yourself that its ok. It's ok that she did that, and it's normal for me to feel like this. Remember that while she was off doing her thing, you were experiencing life in a different way.. both your paths led you to eachother (and the same place).

If I were you, I'd feel pretty dam good that this amazing woman put that crazy life behind her and chooses every day to be with me. I would take alot of comfort in that.

All the best to both of you :-)
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I guess this is old farts by now, or maybe it isn't. But I have/had a similar problem with my ex, each time I saw her doing anything I felt dumbfounded at how decisive and resolute she does certain things. The thing is, I know about her weaknesses as well, but I can't help putting her in a place where I want to be so badly that sometimes I can't utter a single word in her company. In my opinion, there are two problems combined here: first, you are unhappy and insecure about your past because there were wishes and desires that never came true for you; second, meeting a person that is both attractive as a potential partner and apart from that is ALSO a person that you would like to be more than you can stand is a difficult position. The combination of both is an exponential combination of insecurities.

So what to do about it? Either you try and relax (and do NOTHING AT ALL, just wait, give it time, be yourself, lean back, let events unroll and watch her watching you) and see what you have that she doesn't have a clue about (believe me, there are things she doesn't have a clue about), or you go ahead and try to do the things you have always wanted to do. If you feel this is like throwing rocks with the guys, then do something else you have always wanted to do, and maybe invite her along, or don't, whichever way you feel comfortable with yourself. Start small. Plan a short vacation just for yourself. There is adventure if you don't stop looking. Adventure doesn't have to be about foursomes, group sex, fisting and anal gaping, alright? Forget this sh*t. If you want more sexual experience to feel good about yourself, then why are you in this relationship anyway? Adventure is about enjoying the things that you enjoy. If you can show that during your time on planet earth there was something you liked to do, then you are infinitely more interesting than someone who just wanted to increase their number of experiences. This is how cool people work. They don't let things stand between them and what they like. So don't let your envy stand between you and her maybe? See yourself as a pupil going to school again, and here you have the best teacher you can get. She will sleep with you, she will show you how to enjoy life, she will make you a better person in the end. Take advantage.

I think the best tip I can give you is try and make time for yourself. There must be moments in your life when you feel that you are enjoying yourself alone, without anyone's help. Take these moments and multiply them. You have one life to waste, one life to watch television, one life to scratch your ass...other people do the same! She will have done it! And if she didn't, maybe she is longing for someone to show her this side of life. Just hanging out in the same place forever together. And besides, she obviously needs something that you have that she cannot produce herself, otherwise she wouldn't be spending a single minute in your company, right? Find out what this is, refresh yourself thinking this is what you are really good at, decide whether you want to be that guy.
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