Luv Doc: A Very Honest Person

Hi, Luv Doc

OK I am about to be brutally honest here. I am a very honest person and believe the only way to get help is to ask for it and be extremely honest and open minded so here we go. Let me tell you a little about myself. I am an Anglo, white male, 54 years of age and will be 55 in March. I served 20 years in the U.S. Air Force and retired. My overall life and needs (outside of sex, relationships, and romance) have been good. Growing up in south Texas (Kingsville) I was bullied a lot, picked on and even beaten up by two girls in 7th grade. And many of my peers witnessed it. So I was on the bottom end of the pecking order. I never dated in school to include high school and remained a virgin up until 1992 when I met my second girlfriend while in the military. There are 18- and 19-year-old men that have had more sex than I have in my entire life. My wife and I have had a son together back in 1996. But as of about 2005 I have not been laid or had sex. Now my wife has told me I can have a hall pass if I want it. Or a little one night stand once in a while. But I have not cashed it in. I thought sites like Adult FriendFinder or Ashley Madison might be OK. But then I read in one of your articles that 60% of dating sites are a waste of time. So how can you help me? What are my options? How do I even approach a woman? Even though I have a lot of mechanical and technical skills, I am no pick up artist. Like I said, men in their teens and 20s are better at this than I am. What I am saying here to you is something I would like to talk with women about face-to-face to get their advice, too. So help. Life is quickly passing me by.

– James

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Let me break this down, just so I can keep it straight in my own head: You are a married male who hasn't gotten laid since 2005, and you have a hall pass from your wife for extramarital sex, but you feel that given your background and relative inexperience with women, you find it highly unlikely that you will be able to even meet, much less have sex with, another woman.

Damn dude. There is just so much here to unpack, but let's start with your wife. As nifty as it sounds, I am highly uncomfortable with the idea of a "hall pass." In this case, particularly, she is allowing you "a little one night stand, once in a while." There may be a chance that such a scenario could happen for you without paying a prostitute, but I think that is unlikely – precisely because that "little one night stand," if it somehow manages to happen without the exchange of money, will eventually blossom into a torrid, insatiable fuckfest that will spin out of control and ruin the comfort and tranquility of your marriage.

I get it. Maybe your wife doesn't even want to look at that thing, much less touch it, but before she gets too cavalier about her open-mindedness regarding your sexuality, she might want to consider you might eventually leave her for your new fuck buddy. On porn sites, the messy part of sex is the wet spots and the money shots, but in real life, the messy part of sex is managing everyone's feelings between orgasms. A belly button full of semen is an easy cleanup compared to the jealous rampage of a hurt and betrayed wife. Shit gets broke. So broke it can't be easily fixed.

So, if you have really hashed this out with your wife realistically and she is OK with the possibility of your marriage going tits up, I recommend you get on Adult FriendFinder and Ashley Madison and every other possible online site you can, because even if they are 60% bullshit, that's better than your odds are going to be getting some woman in a bar/produce aisle/book club to sit still and listen to/sympathize with the predicament you're in. Why? Because a story like that is something you don't drop on someone you just met. They are going to need to like you enough to summon up some empathy, and that's a tall order. It's going to take some time.