“Maybe you guys can have sex with a porn star together? That would be a fantasy for me, big-time.”

Sugar and Spice
Hi Leah, I saw you on The Millionaire Matchmaker when I was like 13. I knew you were one of the baddest bitches ever since. I’m a young girl, hustling, trying to follow dreams and make it in NYC, but as you know, our beloved Big Apple isn’t cheap. I’ve been considering becoming a sugar baby but I’m not sure if I should. The money aspect sounds great, but I don’t want to become soulless just for a check. Do you have any advice for me going about that process? I’m hella nervous and slightly skeptical that I might get snatched by an old man who’s actually part of a sex-trafficking circle.

You are too funny. I love that you were watching Matchmaker at 13 and could spot a baddy at such a young age. Kudos! From what I can tell by your email, you sound like an old soul in a youngin’s body. Okay, so being a sugar baby. It’s a nice term for prostitute/sex worker/hooker. Because that’s what it is. And that’s totally okay… if you can handle it. I don’t believe these guys just want someone to go to dinner with. The temptation for more money will probably entice you to cross that line from a companion to a hooker. It’s not a judgment. Look, we are all hookers in one way or another. If my daughter was asking me this I would say NO. But you aren’t my daughter. So I’m saying, think about it hard. Maybe try it once? There are websites that provide these services. My more sane and sound advice to you is, get an internship at an amazing company, find a mentor, put your energy into elevating your value and experience. It will be a lot more enjoyable then staring at an old ugly pervert while you eat lamb chops and drink champagne. Promise.

Garlic Nots
I’ve been with this guy for about a year. When we have sex, he pulls out and finishes in my mouth every single time. It’s not horrible, but it’s not my favorite, either. He’s a chef, so he often tastes like garlic, too, which adds another layer to things. If I had it my way, we’d do that like once a week, not once a night! I feel like porn has made it so men expect this now, and while I love this guy and I don’t want him to feel rejected, I feel like it’s a bit much. Help!

No, no, and no! If you don’t want extra protein every night tell him in a nice way. Tell him you want him to come on your tits instead cuz it turns you on. You are so right about men thinking porn is real-life. It’s nuts. If you love him, then you will make it work. Plus, he’s a chef which means he has a job and these days that’s hard to find (crazy how low my standards have become). I think once-a-week come-swallowing is very fair. And he should, too.

Furballs
The guy I’ve been seeing has two small dogs, and he lets them jump up on the bed and stay there all night, even while we’re having sex. I’m not into dogs, especially when they’re staring at me while my ass is up in the air. When I complain about them being around all the time, he just claims they’re lovable and says, “What’s the big deal?” Is this a deal-breaker, or should I mellow out, because otherwise this guy is pretty great.

This is a very sensitive subject. A lot of people see their animals as family members so you have to be careful not to offend. I think you should tell him that you got bit by a dog when you were younger and it traumatized you. And that you don’t mind being around his dogs, but during sex you want to be able to focus fully on him and instead you are fighting off your PTSD from being attacked when you were a kid. Explain to him that you want to be fully engaged while in reverse-cowgirl and not worried about getting mauled by his little furballs with teeth that are creeping up on your vag and his balls. If he isn’t receptive to this, keep it moving. Good luck, boo!

Born to Porn
The guy I’ve been with for a year now is really into porn stars. I’m not just talking about pleasuring himself to porn, which I think everyone does. He goes to the AVN awards in Vegas, and attends adult conventions a couple times a year so he can get stuff signed by his favorite stars. Sometimes when he’s talking about how nice certain porn stars are, it weirds me out. Oh, and on Sunday nights he plays Dungeons & Dragons all night with his friends — he’s been doing this since they were all teenagers. He’s a great guy, and we get along really well. Should I just let him have his interests and deal with it?

Girl, I’m more concerned with Dungeons & Dragons than the porn stars. How old is this guy? I didn’t even know that that shit still existed! As for the AVN awards, I mean, I wouldn’t be too into that, but at the same time I really love porn stars, too, and I could see how someone would totally fan out. I think you should go with him to the adult conventions. Maybe you guys can have sex with a porn star together? That would be a fantasy for me, big-time. Aside from that, it sounds like his somewhat nerdy and off-color interests don’t bother you that much. It’s all about what you are comfortable with. Great guys are hard to come by.

Man Up
Tell me if I’m being insensitive, or if you agree with me on this. I’ve been with a guy for about nine months now, and he’s awesome… except he cries really easily. Sad songs make him cry. Sad movies, too. Even those lame “send money to feed this villager” commercials! He’s a very stable guy, but this amount of vulnerability is making me think of him as less of a man. Is the problem that I’m expecting men to be lumberjacks who can’t cry? Struggling with this.

Sorry for being insensitive, but this made me laugh. It’s very odd. I’ve never been with a man that cried easily. Quite the opposite. And they all turned out to be psycho, so maybe this is good news for you. I guess it would be hard for me to deal with a man who cried more than me. But again, that doesn’t mean he’s not able to be a “man.” I think you need to judge his masculinity on other things. Forget about the crying for a minute. Does he fuck you like he means it, or does he fuck you like he’s a bitch? Do you feel protected by him? Like you can count on him? You have to ask yourself these things, then judge whether he is manly enough for you.

Photo Contributed by Leah McSweeney