Leah McSweeney is one bad bitch (her words, not ours).

In New York City in 2002, Leah witnessed a bunch of cops beating the shit out of her friend outside a Midtown club.  When her repeated pleas to stop were ignored, Leah threw a bottle at them. That’s when one of the responding officers punched her in the jaw, smashed her face into a subway grate, and knocked out two of her teeth. But what might have been yet another miserable encounter with the NYPD was the spark she needed to claim the life that was rightfully hers. Two years later, Leah was awarded a $75,000 settlement from the NYPD, which she immediately used to launch her clothing line, Married to the Mob — a pioneering streetwear brand built to promote Leah’s values of women’s strength, empowerment, and unflinching nonconformity.

Twelve years, five continents, and millions of dollars later, Leah is still kicking ass.  Whether she’s challenging the cultural illuminati by taking the piss out of revered brands like Supreme (Supreme Bitch, please!), beating the shit out of Andy Dick for being… well, A. Dick, or exposing her more vulnerable side on social media, Leah continues to stay true to who she is.
Leah is a mother and a fighter. She is a flawed, self-aware, emotional conqueress who understands that the best way to outpace life’s curveballs is to overwhelm them with drive, guts, and confidence. Most of all, she is completely unqualified to be giving us any type of advice. So, here goes nothing…

PAIN IN THE ASS
Leah, please talk about anal. What’s your take on it? I’ve always thought of it as something to save for my future husband. Well, I found him, and gave it to him, and I decided it was literally the best sexual gift you can give to your husband. What do you think?

Anal. The word alone creeps me out. I’m definitely not into putting things in my butt. I know. I sound prude and lame. I so want to be the girl who loves anal. I should be the girl who loves anal. Sadly I’m not. My ex claims we had anal sex once, but I’d taken a bunch of my nighttime meds and I have no recollection. I actually really don’t believe him since he’s pretty much a sociopath narcissist. But he insists I loved it and that he came in my ass. Again, I have no memory of this. To be honest, I’m scared I’m gonna shit on someone while we’re doing it.

It’s not for lack of trying...I’ve had the tip go in, but it just feels bad. I start to squirm and I’m like, never mind! When I was 16, my long-term boyfriend was fucking me, totally missed, and rammed straight into my asshole. Side note: His dick was huge and he was thrusting hard. I screamed and laid there… for 20 minutes… in tears… thinking I would never recover. So, that about sums up my thoughts on anal. I do think it’s very sweet that you saved your butthole for your husband. That gives me hope. Not just for anal, but for also maybe one day finding a husband. But more likely just anal.

FRUIT LOOPS
I see this young lady I don’t really know too much about. But when I turn to the side, I can see her (from the corner of my eye) putting her hands over her face like a little girl. Maybe she’s shy? It’s like she’s sensitive. I’m not sure if she’s had her heart broken before.
Well, we’ve all had our hearts broken before, but I don’t go covering my face with my hands when a man is standing next to me. Are you sure she’s playing with a full deck? Come to think of it, are you playing with a full deck? This “question” doesn’t make any sense to me. Maybe she has a big mole she’s trying to hide? I have no fuckin’ idea, dude. Just keep it moving!

THREE’S COMPANY
I’ve been dating my girlfriend for three years, and she is probably the girl I’m going to marry. The sex is great, but I want a once-in-a-lifetime experience with her before things get too serious. What is the best way for me to talk her into bringing another girl into bed so that I can get me a threesome?

This is a slippery slope. Usually you wait for your chick to initiate this type of thing. Bringing this up to her will probably end with the wedding not happening. She’s going to feel like she isn’t enough. You must wait for her to initiate it. But, there are ways to gently nudge the subject into existence. Is she into girls at all? Has she had any lesbo experiences? Hopefully. And if so, coax her to talk to you about them. Tell her it turns you on — thinking of her with another woman — but do it without inserting yourself in the situation.

Do you two watch porn together? If not, you should because it’s hot. Watch some girl-on-girl or threesome videos to get a convo going. Then, slowly and sweetly tell her how much it would turn you on to see her with another woman. Wait to for her warm up to the idea. I’ve only been the guest star in threesomes — which haven’t been many. But the woman initiated and brought me in every time. Those are the rules. I wouldn’t break them if I were you.

My ex claims we had anal sex once, but I’d taken a bunch of my nighttime meds and have no recollection.

REHAB REBOUND
I met this guy in rehab, and I’ve been seeing him for two months. We’ve had hot make-out sessions in rehab, but we’ve both recently completed the program (he actually got kicked out for smoking cigarettes). Since then, we’ve hung out a couple times, but he hasn’t tried to fuck me. He’s an ex heroin addict and on Suboxone [which is used to treat addicts], so I’m wondering if maybe he has some erectile issues. Now he’s saying he’s in a hospital with the flu. Help!

Girl… you are buggin’! Rehab romances never last, and they are never good for your recovery. This dude is not in the hospital because of the flu. He’s probably laid out somewhere, nodding off, making excuses. I’m an addict in recovery, so take it from me — I’ve been down this road. When I was six years sober, I dated an alcoholic. Great idea, right? Turned out to be one of the most traumatic experiences of my life.

Addicts want to get high. They do not want to take care of your pussy properly. Trust. They are fucking monsters. Stay the fuck away from this guy. He will probably end up destroying your life and ruining your sobriety. And yes, the Suboxone is probably making his dick like mashed potatoes. I know you’re probably super horny because you are off drugs and alcohol and looking for a distraction… but find yourself a guy who’s not also newly sober and can get a hard-on. Actually, go get a vibrator. Get a really good one and go nuts. Do whatever you need to do to get yourself out of this sexless situation with a guy who will turn your life into a goddamn nightmare.

Need Advice? Email leah@penthouse.com