Sex Advice From Gutter Punks

Q: “I found out my boyfriend used to work as an escort. Should I confront him about it?” A: “Wait, was his name Thomas?”

By Kelly Bourdet

Wolfy, 23

My boyfriend doesn't take showers as often as I’d like, and sometimes he smells. I'm neurotically clean and it bugs me a little. How do I ask him to shower without coming off as offensive? 
I don't take showers often. First, just to ease into the subject, ask him, “What do you call a crusty gutterpunk without a girlfriend?” 

What? 
Homeless. Second of all, when it comes down to it, if he's not on the streets and does have the opportunity to take a shower, what the fuck is he doing not taking a shower? Whoever this is, I’d love to get some contact information, because I'd like to take a shower. I will take as many showers as she wants, consecutively. And I will show her the time of her life in the shower, if she wants. I've actually had girls kidnap me from the streets, and they're like so: clothes to the laundry, you in the shower. 

Is that the perfect date? 
If you haven't taken a shower in a month! I haven't complained yet, but if you want your boyfriend to take a shower and he doesn't want to, stop kidnapping crusty kids off the street! 

My girlfriend wants me to stop watching porn because it makes her uncomfortable. I don't want to stop. What should I do? 
If you’ve got somebody standing right there in real life, I'd say do whatever you're into. If you're into the Hot Carl or into the Sloppy Johnson, anything like that, find someone who can do that. Otherwise, deal with what you got and enjoy that you can have it in real life.  

My girlfriend went out of town, got really drunk, and had sex with another dude. She told me, but I'm still upset about it. Should I forgive her or is drunkenness just her excuse for cheating on me? 
I am a professional drunk. Coming from a professional drunk, drunkenness is not an excuse for anything. I often use the excuse that if I don't remember it, it didn't happen. But people don't see it that way when they remember. They call them “spirits” for a reason: your true spirit comes out when you drink. You do what you do, you got what you got, and you're going to represent that when you're drunk. So no, it’s not an excuse.
 
But also, was she on a three-week bender? If she's on a three-week bender, then why aren't you on a bender with her? And why were you at home? Why aren't you out partying? If you're too boring to take a vacation, maybe that's your issue. If you're too boring, then yeah, whoops, sorry.  

I'm in a relationship with a great guy I met on a gay hook-up website. He recently told me he used to use the site for sex work. He doesn't do it anymore, and he's clean, but I'm still uncomfortable. How do I get over this? 
First of all, was his name Thomas? 

I don't know. All these questions are anonymous. 
Thank God. It's a great sign of respect that he told you. Why would somebody doing what they do to get by be immoral? No need to judge the past of another person. 

I keep reading about anal stimulation and how great it is for guys. I'd love to bring it up with my girlfriend, but I don't to freak her out. Any tips on a good way to bring that up? 
Start by holding hands, and mess with your fingers when you're holding hands. You’ve got to, as you're slipping across the butt cheeks, just find a way in there. If you pre-grease, you're probably better off. It makes it a little bit less noticeable. Just look at her and go, “Oh, that's where it went? Oops.”