We get a lot of advice questions coming in at EMandLO.com, but sadly, we just can’t answer them all. Which is why, once a week, we turn to you to decide how best to advise a reader. And frankly, this one is a doozie. Make your call by leaving your response in the comments section below.

Dear Em & Lo,

My boyfriend likes to ask me about my past sexual relationships with other men while we are having sex. How we did it, where we did it, things like that. He’s the one with an extensive sex history! While he finds it a turn-on, I find it a turn-off. It breaks my concentration on us and the moment to be asked to think about people I just don’t think about. Do any other women have this issue with their partners?

– Over It

What should O.I. do?

We get a lot of advice questions coming in at EMandLO.com, but sadly, we just can’t answer them all. Which is why, once a week, we turn to you to decide how best to advise a reader. And frankly, this one is a doozie. Make your call by leaving your response in the comments section below.

Dear Em & Lo,

My stepdaughter just confided in me she had recently lost her virginity with her boyfriend. She’s fifteen and doesn’t want me to tell her mom. She said that I’m the only one she feels comfortable talking about sex with. I’ve always taught her to practice safe sex, choose her potential partners carefully, and to be discreet about her personal choices. What do you suggest about her request not to tell mom?  I don’t want to betray her trust, but I’d also like to avoid the scalding hot water I’ll be in if it ever gets out I held onto this piece of info.

– The Secret Sharer

What should T.S.S. do?

Dear Em & Lo,

Under Pressure

Dear U.P.,

Do NOT to do anything you don’t want to do–it’s that simple. Just tell him you really like him and like hanging out with him, but you want to take things slowly and you’re not ready to do anything beyond kissing at this point. If he gets mad and wants to break up with you, then you should break up with him! If you know you’re not ready to get physical, he should respect that. If it’s a deal breaker for him, so be it. You’ll feel better if you stay true to yourself without him than you’ll feel if you get pressured into betraying yourself WITH him. And don’t buy any lame excuses from him about everyone else doing it, blue balls, doing it for love, or doing it for your country. You have plenty of time to explore things sexually as you get older, become more mature, and find the right guy(s) to experiment with in your adult life. Don’t let some jerk rush you into anything before then.

Good luck!
Em & Lo

We get a lot of advice questions coming in at EMandLO.com, but sadly, we just can’t answer them all. Which is why, once a week, we turn to you to decide how best to advise a reader. Make your call by leaving your response in the comments section below.

Hi Em & Lo,

For various reasons (long abusive relationship, thankfully ended, plus my own social ineptitude), I’ve only had sex a handful of times over the past 5-6 years and I feel so empty and frustrated. At the risk of sounding like an asshole, I’m fit and attractive, I look after myself, I’m moderately successful.  I’m 27 years old and would love to have a decent and fulfilling sex life, but have no idea where to start. I’m a quiet and introverted person, so I realise I’ll probably have to meet guys online. But how can I be honest about my inexperience without putting off potential partners? I sound so weird and needy — and that’s not who I am, or who I want to be. I have no idea how to initiate sex or get someone off and I would love to learn. I’m okay at building a rapport with someone I like, but how do I get over the physical awkwardness? I’d be so grateful for your help, as this is making me miserable.

– Too Old to Be a Newbie

What should T.O.T.B.A.N. do?

Dear Em & Lo,
I’ve been with my boyfriend for 3 years. I’m 21, he’s 28. He’s the only person to ever perform oral sex on me, so while I have no one to compare him too, I know that he is bad at oral sex. He pushes his entire face on my lady region and just moves side to side, as if that is supposed to feel good. He hardly uses his tongue and I don’t think he even understands he needs to focus on the clit. After 3 years, I have no idea how to tell him that he’s not doing it right. Help!
— Suffering in Silence

Dear SiS,

Oh dear. We’re tempted to tell you to dump this guy and start over with a new one, because it’s a million times harder to teach an old partner new tricks. This is in large part because there’s no easy way to say, “You’ve been screwing up for three years and I just never got around to telling you.” How would his ego ever recover from such a blow? How would he ever know to trust your sexual response in bed again? This is why we emphasize again and again and again the importance of communication in bed from the out-set — not to mention the importance of never faking.

But maybe he’s a good guy. Maybe you really love him. We’re going to assume you do, as there’s obviously a reason you stuck with him despite godawful oral. First off, it’s important that you lose the attitude (are we wrong in sensing a little attitude in the phrase as if that is supposed to feel good?). How on earth is he supposed to know what feels good if you never tell him? Maybe his last girlfriend didn’t like clitoral attention during oral (some ladies don’t) and that’s why he’s shying away from yours. Or maybe no woman has ever had the decency to tell him how to do it, which means he’s flailing away down there like a wind-up toy.

Once you’ve accepted that you’re as much, if not more, to blame as he is, you can start your gentle campaign to reeducate him. The next time he goes down on you, ask him — as if it’s a thought that just occurred to you — to focus on your clitoris. When he gets there, give him feedback — faster, slower, harder, softer, a little to the left, etc. And when he gets it right, go crazy with the positive feedback:  moan, call his name, say yes, whatever works for you. The next time he goes down on you, offer a different specific suggestion of something he might try. Again, guide him gently and go nuts when he gets it right. Don’t try to change his entire approach in one session — after all, you’ve waited three years, what’s another few weeks?

Oh, and next time you’re going down on him, why not ask what he’d like you to do? Just in case, you know, he’s been suffering in silence for three years too. Kidding! (Sort of.)

– Em & Lo

Dear Em & Lo,

I slept with a co-worker after our holiday office party. We were both very drunk, and while I don’t regret it, I don’t want anything further with him. Unfortunately, he’s giving me all the signals that he’d like for us to continue what was, for me, just a one-night thing. To be honest, I’d probably be up for the occasional booty call, but I think he’s looking for more. We’re both at the same level in the company, so it’s not like there’s a power issue, but it’s definitely getting more awkward every day. Any ideas on how to extricate myself without making things worse?

–Hiding Behind the Office Plant

Dear HBTOP,

We know this isn’t particularly helpful, but we’ve gotta say it: We told you so. What were you thinking?!

Okay, clearly you weren’t thinking; the eggnog was in charge. So your New Year’s Resolution for 2011 is this: follow our advice to the letter. When we tell you to avoid the mistletoe at your holiday office party, we mean it. (What, you thought we were just jealous because we work from home and didn’t have a holiday office party?!)

In the meantime, you need to extricate yourself from this sticky situation (was it literally sticky? Please don’t tell us you got kinky with the eggnog). Given that the oversized office plant isn’t always going to be there for you, it’s time for a little old-fashioned communication. Invite your colleague to coffee and break out the old “I don’t shit where I eat” chestnut–though we recommend using a more delicate turn of phrase. (Not the pen and inkwell one either, lest he mistake you for a 55-year-old executive who just slept with his secretary.)

But don’t go overboard and imply that you’re head over heels in love with him and that you two are star-crossed lovers divided by a cubicle wall, because he might just quit his job in order to be with you (even more awkward!). Just keep things as vague as possible. Tell him, “I’m feeling a little bit uncomfortable about what happened at the party and I hope we can still be friends.” Or make light of things and say, “I hope we don’t make it into the next company newsletter… in the meantime, do you think we can just chalk it up to the eggnog and be friends?” For his ego’s sake, don’t let on that you know he’s really into you…just act like you both got drunk and did something stupid, and let him play along. (If we know guys’ egos, he will.)

By the way, don’t consider this a permission slip, but if you don’t have the labes for a coffee date, then emailing him some or all of the above is better than saying nothing at all. It’s still wussy as all hell, mind you, but the sooner you break the news to him, the better.

And next time? Don’t make us say we told you so. It may seem as if we like saying it, but we don’t.

Still telling you so,

Em & Lo

We get a lot of advice questions coming in at EMandLO.com, but sadly, we just can’t answer them all. Which is why, once a week, we turn to you to decide how best to advise a reader. Make your call by leaving your response in the comments section below.

Dear Em & Lo,

I have been dating my boyfriend for two years. We are both so in love with each other and talk of marriage in a few years. He is Pakistani and I am white. His religious Muslim family approves of me.

A few months ago, I found out that him and his cousin who lives in Pakistan were writing love letters to each other for two years before we met. I confronted him about it and we settled issues for the most part. He claims to have never loved her. I believe him for the most part, even though the only reason he tossed the letters was because he knew I’d not tolerate or be with him anymore. He is very clingy to things of his past. It hurt so much that he wanted to save these letters because it’s as if they meant something to him.

Since then I have gotten over this issue for the most part because we talked about it many times and he promised me he never loved her. I don’t want to sound like a stupid girl, but I believe him. I really do.
The problem is, they still talk. And her being his cousin, it’s difficult for me to tell him that I don’t want him talking to her, because she is his family. I know he has plans to go to Pakistan on vacation and I am extremely hurt and mad because I know they will see each other. I don’t think I’d be able to be with him anymore even though I love him deeply. I know that if he were in my shoes he would not want me to see someone I wrote love letters to or talk to them, even if I really didn’t ever love them.

I have been avoiding this talk because I can’t bear to be without him, I love him so much. I know that him going to Pakistan is somewhat out of his control because it’s his parents choice, but I don’t know how to handle or approach this situation. I trust that nothing will happen between the two of them while he is there. But I know they will be hanging out a lot, and I cannot bear the thought of him being near her, the girl he thought he loved for two years.

What do I do? I don’t want to break up with him, but I don’t want to be that stupid girl who gets hurt like this either. Ideally he would never talk to her or see her again. Am I being unreasonable for wanting this? I don’t think I am considering he has told me that he does not want me talking to guys from my past. But then again, they were not my cousins.

– Dating a Kissing Cousin

What should D.A.K.C. do?

Dear Em & Lo,

Recently my boyfriend of six months has asked me to fool around (and maybe have sex) with another man, so he can secretly watch. We have a very healthy sex life (7-10 times a week) and both feel deeply in love, but he says that this desire is a real turn-on for him. I am not interested in having sex with another man, but can understand why it might turn him on.

My fears are that after the act, we would have trust issues and our relationship will be destroyed. I love him very much and do not want to lose him. I want our sex lives to be exciting and fun… but would this one exciting time ruin our relationship? I think it might be a turn-on, but I would never be able to allow him to do the same thing with another girl. Of course, I don’t think that is fair. What should I do?

–Conflicted But In Love

Dear CBIL,

You’re totally right to be conflicted. In fact, you’re totally right to be totally shitting yourself at the thought of doing something like this. That doesn’t necessarily mean that it’s right or wrong for your relationship, but you’d be an idiot if you went fearlessly into that kinky night. This is a huge deal, and something that is very right (and very hot) for some couples, but very wrong (and very destructive) for most couples. So, how can you figure out which kind of couple you are?

Let’s start with him. Has he ever done something like this before? Sure, the idea might turn him on, but how does he know the real-life version will? You have to be some kind of advanced human being — i.e., one who’s missing the jealousy gene — in order to handle this, let alone get off on it. Is there anything in your relationship to suggest that he’s this sort of being? Or, more pertinently, to suggest that he’s not? Ultimately, of course, he can make all the promises in the world, but there’s no guarantee that he won’t see you differently after something like this. In fact, something like this will change your relationship, there’s no way around it. Perhaps for the better (you both suddenly decide, I want to be almost-monogamous with this person for the rest of my life!)… or perhaps not. That’s the risk you take. Because without risk, where’s the taboo-breaking fun?

But it’s not all about him, is it? Listen, it’s one thing to try out a new position you’re not all that fond of, just because your boyfriend’s into it. But to have sex with someone when you have zero interest in doing so? Then he starts to sound more like a pimp than a lover. And have you told him that if you did something like this, you’d be incapable of reciprocating? If so, does he understand that you wouldn’t then “owe him one”? And that, actually, he’d kind of owe you one: next time, he’d be the one that had to indulge your fantasy.

Perhaps the two of you can start off in the shallow end of the kinky waters first; that way he can experiment with how much he’s truly comfortable with, and you can experiment with what sort of exhibitionism/voyeurism (if any) might turn you on. Try talking through this fantasy together during sex, maybe focusing on a specific guy. Browse online personals to fantasize together about who you might “pick.” Visit an adult chat room for a little cybersex with a stranger while he watches you type. Go out to a club together and have him watch you flirt with strangers, see how it makes him feel. Go to a saucy night club and dirty-dance with someone else in front of him. Go to a sex party but just have sex with each other — or just watch other people have sex. There are plenty of progressively saucier things you can try out before you actually take the step of bringing in an outsider.

It may be that any of the above is enough of a turn-on for both of you and you decide to stop there. Or one of you may find something too weird and ask for a time-out, which is totally, completely acceptable, by the way; if it simply doesn’t feel right to you, then you should say no, even if it’s a relationship dealbreaker for him. (Hey, no one said it was easy out here for a pimp.) Or perhaps you’ll both get so turned on that you decide to dive head-first into his original idea. But at least this way you’ll be going in with a little more information about how you might handle it, and how your relationship might withstand it.

Your friendly lifeguards,
Em & Lo

Dr. Kate is an OB/GYN at one of the largest teaching hospitals in New York City and she answers your medical questions every few weeks on EMandLO.com. To ask her your own question, click here.

Dear Dr. Kate,

Is there any way to prevent yeast infections?

– Itchy & Scratchy

Dear I.S.,

Not completely. The biggest risk factor for getting a yeast infection is having a vagina — not an easy risk factor to modify. But the more gently you treat your vulva and vagina, the less likely you are to get a yeast infection. This means three things: Limit your chemical exposure — no perfumed products like bubble baths and sprays, use simple soap in the shower, no daily pantiliners…and for god’s sake, no douching. Keep yourself dry, and let your vagina breathe — cotton underwear over nylon, no undies at night, get out of your workout clothes as soon as you’re done working out, change your tampons and pads frequently during your period. And limit your exposure to irritants — use just your fingers to clean yourself in the shower, no puffs or washcloths, and use a liquid clothes detergent over powder.

– Dr. Kate
Gynotalk

Dr. Kate is an OB/GYN at one of the largest teaching hospitals in New York City. She also lectures nationally on women’s health issues and conducts research on reproductive health. She generously shares her medical wisdom with EM & LO readers every few weeks. Check out more of her advice and ask her a question at Gynotalk.com.

We get a lot of advice questions coming in at EMandLO.com, but sadly, we just can’t answer them all. Which is why, once a week, we turn to you to decide how best to advise a reader. Make your call by leaving your response in the comments section below.

For a while now my girlfriend and I have been enjoying anal play, both of us giving and receiving, even with toys. My question is: is this ethically wrong on my part or hers? I mean we both get pretty turned on by it. I always thought gay men did anal so does that mean I’m gay? I love my girlfriend and love being with her and never dream of another guy — yuck! Plus, she likes feeling in control. She told a couple of her girlfriends and now they want to find a guy like me who is open to exploring what a man’s body can actually do. Am I just over-thinking this or are we seriously goofy?

This one is obviously a gimme.