Sex & Relationships

Ask Ashley: sleeping with Mister Big

Some of the girls I’ve been with lately complain that I’m too well-endowed and they don’t want to have sex with me anymore because it’s painful. I know a lot of guys might love to have this concern, but they don’t realize the problem it causes. Do you have any tips on how I can make sex less painful because of my size?

— Anonymous

Lately? So what did all the other girls before them say? Being too big could definitely be a problem. Honestly, I dated this football player for a little bit. It never got to the point where we were having intercourse, but I did think, “How is that thing going to fit inside me and feel good?” I mean, I didn’t know they made them like that! It was like 12 inches long and the width of a 5-liter Poland Spring bottle. I didn’t want any part of it.

I’m not sure if yours is anywhere near that, but I do believe it’s possible to work it out. The key is to be gentle. You may not be able to put it all the way in the first couple — even dozen — times, but remember: The G spot is only about 1 to 2 inches up, so you don’t need to go all the way in. She also won’t be able to be on top completely, so I’d suggest doing it doggie style or missionary. In a way, you need to “break her in” so she becomes used to the size of your manhood. I know you’ll find a girl who can handle it.

My husband comes home from work with perfume on his clothes. He says he walks through a department store on the way to his subway stop and women at the cosmetics counter spray him, but the perfume always smells the same. I don’t know whether to believe him.

— Marta, 27, Manhattan

I wouldn’t believe him. Every time I walk through a department store and that woman is standing there with that little bottle in her hand, I put my hand up, say no thank you and keep walking. They never just spray you. Now, let’s say he does walk though the department store on his way to the subway after work. (Why does he need to walk through the department store again?) And the girls do spray him, because, let’s face it, he’s a guy, and guys aren’t like us when it comes to refusing the perfume girl (who I’m sure is a different girl every day). What are the chances that she’d pick up that same scent every time? Or that the department store would be pushing that one perfume over and over again?

After you confronted him, the next time he walked through that department store, he could’ve told the girl, “No thank you. I have a wife, and I don’t want her to get the wrong impression.” It sounds to me like he’s been lying to you and thinks you’re stupid enough to actually believe him. The fact that you think he’s lying proves you’re not stupid. Look, if you can’t trust your guy, then why are you with him? I would follow him to find out if you’re overreacting. Either way, it’ll give you closure.

I have a platonic relationship with a friend I’ve known for 10 years. I’m very attracted to her and want to be more than friends. But I’m afraid to tell her, since I value our friendship. Should I let her know my true feelings?

— Mark F., 40, Union Square

So you want to break out of the “friend” category? This is super-hard. Because you two are so comfortable together, it’s difficult to switch over. You need to step it up big-time. You need her to see you and want you in a sexual way — not a buddy way.

Before you tell her how you feel, do a little “foreplay.” When you lean in, hold it there a little longer than normal. Perhaps change the way you look at her a little bit. Dress and smell sexier. Be confident. But let her shift out of it and discover the subtle differences on her own.

After slightly changing your habits, take her out to a really romantic dinner. Talk about life and what you’re looking for in a girlfriend and wife. Paint a picture. Show her that you know what you want. And then say how you see her as that person in your life. Tell her that you want to make this work with her, if she’s willing to try. Say something like, “I’ve been thinking about this for a while, and I haven’t said anything because I was afraid if I told you, I’d lose you. And I don’t want to lose you.”

At this point, you did your part. You showed her and told her how you felt. It’s up to her to want to take that chance on you. Even if she says no, I doubt it will harm the friendship — you’ll just have to decide if you can be just friends. That’s the hardest part, really. But it’s better than always wondering what could have been. Good luck! I’m rooting for you.