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Ask Trixie: Is it morally wrong for me to have sex with a married woman so I can lose my virginity?

Trixie - I am a 38 year old male virgin. I've had life long issues with shyness, social anxiety, and avoidant personality disorder. It has been a long, weird road. I've never had a relationship or even a fling. The most I've done is kissed. I am socially awkward and it is just really difficult for me to connect with women.

I got tired and decided to (finally!) take action to try to avoid become a 40 year old V-bomb. So I posted an ad to Craigslist (before they shut down the personals forever) explaining my situation. I got mostly bots, but one real reply. We chatted for a bit. She is understanding, doesn't mind my situation, is patient, we click conversationally, in terms of humor and more. The only hang up.......she is married. She says she is in a now-unphysical marriage, and has made a clear decision to seek out something to fulfill this part of herself before the idea finally passes over based on age and all. If not with me, it will be with someone else, that has been made clear, not that that excuses me from potential moral hang ups.

So basically I have before me someone who is patient and understanding about my quite late virginity, desirous to 'teach me', and I click with on several personality points. But there is a hang up. I don't really want to be involved with a married woman. I feel like I'm crossing a line of morality. But maybe it's overactive 'moral' lines that have got me into this predicament to begin with. Maybe I just finally have to let go of socially implanted hangups. Or maybe I have to not think of someone else's wife as a random girl to get off with.

I am lost. I want to move past this eternal hump and have sex and love, so I can get some experience and confidence and thereafter have a normal dating life and try to find something real. But I don't want to, after waiting 38 years, just flippantly be an absolute a-hole and spit on 3 separate hearts. Am I overmoralizing by not going for it, or being selfish by going for it. I feel I know your answer ahead of time, but is that based on socially implanted constructs, or real lines that should be respected?

I feel on some levels that, at 38, this might really be my final chance to get some confidence that I can then bring to the world.  –Lost.

Hi Lost! 

It's taken me a bit of time to respond, and perhaps you've made a decision since you wrote me, but if you haven't I'll weigh in with my two cents. Which is...I can't really tell you what to do. I can maybe give you a few things to consider, though.

Some marriages are not monogamous, and the partners have worked out a mutually agreed upon set of rules or guidelines about how and with whom they can have sex. So, you might want to ask her what the understanding is with her husband, considering she's telling you her marriage is sexless. 

Now, If she is doing this without his knowledge, it is totally her choice and she may well find another partner to have sex with if it doesn't work with you. I think you may give yourself too much power in this scenario to 'spit on hearts' and be a homewrecker. So, take a step back. You would not be the first person to have sex with a married person, and certainly not the last. In fact, I think you have a lot of company. Not that it excuses it, but it's also not that rare.

Finally, becoming a sexual person is NOT about one night with one woman. It's about a lifetime of learning and discovery, getting more comfortable with yourself and your partners, creating relationships (short of long term). So that one night might be great an help you get over the hump, so to speak. But then again, it might not.

If it personally bothers you to be in a relationship with a married woman, keep looking for another partner. If you think it will truly help get you on the road to having a healthy relationship with someone who is single and available, it might be worth it for you to do it. Just make sure you are both going into it with the same understanding and expectations of the situation. The really crappy thing would be for you two to have different expectations of what this means and what you want to get out of it. Be on the same page.

So, I can't tell you what to do, but hopefully this gives you a path to think about it. Good luck, and let me know what you decide.

Got a question about virginity, sex, relationships, feminism or filmmaking?  Ask Trixie here.