photo by Bogdan Suditu

Dear Em & Lo.

I’m a 48-year-old female and I can’t seem to achieve an orgasm during oral sex. It all seems too intense. However, I don’t have any problems when masturbating. I feel it is like… someone else scratching your feet… it tickles. If I do it myself, it doesn’t tickle. Is there anything I can do so that my man can achieve this wonderful thing for me?

– Don’t Tickle Me Elmo

What should D.T.M.E. do? Share your advice and experience below…

photo by batega

Dear Em & Lo,

First off, I will say that I love my boyfriend. We are extremely compatible in almost every way. Except sex, and here’s why. About two years ago my boyfriend ruptured a testicle. Sex is now extremely painful for him and he has difficulty reaching orgasm. As a result we rarely have sex. We have talked about it a lot and there seems to be no easy solution. He encourages me to have other sexual partners but I am worried doing so will make him feel inadequate. We do a lot of S&M in and outside of the bedroom and I don’t want him to feel replaced. He insists that it is ok with him and that he wants me to be happy, but im not sure if i can. I almost feel like if he can’t have sex than i shouldn’t be able to either. I know its messed up, but im not sure what to do.

– To Screw or Not to Screw?

What should “Screw” do? Advise her below…

photo by Vivian Chen

Dear Em & Lo,

Is physical attraction a gift or a curse? I’m writing this because a friend and I have been friends for a year. Let’s just say we’ve had our share of up and downs. From us being friends with benefits to helping him deal with his crazy ex-girlfriend. I enjoy being friends with him socially, being able to do regular normal things. We have a lot of similar interests. I’ve always been there for him.

But the downside is our extreme physical attraction to each other is very intense and strong. I don’t want that to destroy our friendship. He’s been cheating on his new girlfriend with me several times. He claims he loves her but she isn’t a very sexual person.

I know he feels guilty when he wakes up and I’m just numb and when I leave I feel like a whore. We’ve set up boundaries — like no sleeping over anymore — but over time I feel our sexual tension will start to build up again. What should I do ?

– Friend with Limited Benefits Plan

Dear FWLBP,

Here’s a better question for you: How many of your other friends make you feel “numb” and “like a whore” after you’ve hung out?

And here’s another question: How many of your female friends make you feel “numb” and “like a whore” after you’ve hung out?

You do have other friends, right? We’re assuming this dude isn’t the only person you share interests with, the only person you enjoy socially. So you don’t really need him, socially speaking. Read the rest of this entry »

photo by Brandon Baunach

Dear Em & Lo,

I have the opposite problem of last week’s advice seeker: My boyfriend is more than willing to go down on me, but I have a very hard time having an orgasm from it. I know it frustrates him that I don’t orgasm every time (or even most times).  I have orgasmed from manual stimulation once or twice and a couple of times from oral sex.  We are comfortable enough with each other that sometimes when he’s failed to bring me to orgasm, I’ve masturbated in front of him until I had an orgasm (which he enjoys).  I know it’s easier for me to do it than it is for him because I’ve had a little more practice, but how can I help him?  We are relatively comfortable talking about sexual issues, but we are usually both so frustrated by the end of the experience that we just want to go to sleep.  He tries so hard that it makes me feel bad when it doesn’t happen.  What should I do?

– Oh Oh Oh…No

Dear OOON,

It is sooooooo frustrating when you’re with a guy that you care for and are attracted to and want nothing more than to have an orgasm with, but it just never seems to happen. Unfortunately, many women find the ways they’re “supposed” to have an orgasm with a partner (during intercourse, or at least oral sex) don’t work for them. They internalize this cultural expectation which puts undue pressure on themselves, making it even harder to relax in the moment. And for most people, pressure is not an aphrodisiac. So they — and often their partners — try and try and try but to no avail and end up feeling like failures. Again, Frustrating with a capital F!

First, you’ve got to stop setting yourselves up for disappointment. Try to just enjoy sex without it being so goal-oriented. Sex doesn’t always have to end in orgasm for it to count; yes, orgasms are great, but making sure you’re both having a good time and experiencing pleasure is what really matters, orgasm or not.

Next, you’ve got to teach him exactly how you masturbate. Try to have him mimic the sensations and techniques to a tee. Be explicit about what goes where, pressure, pace, etc. Forget the idea that this somehow won’t constitute “real sex,” that’s it’s subpar because it involves his fingers rather than his penis or his mouth. Handwork is sex. Reject the notion that good sex should just come naturally, that it can’t be taught. Every woman’s body works differently, and some need more specific and precise stimulation than others — and that stimulation may not be intuitive for a guy to figure out on his own.

There are plenty more steps you can take to improve your chances of climaxing with him — you can read them here:

• 10 Ways to Increase Your Orgasm Potential
• Can Women Orgasm from Intercourse Alone?
• 10 Steps to Orgasming Without a Vibrator

After employing all these techniques, let’s assume he’ll eventually master your particular masturbatory technique. Hooray! After a while, you’ll probably want to find a new way to climax with him. Great, go for it! Just remember to keep your expectations low. Don’t start this new quest to the exclusion of everything else. And consider the possibility that you may just have one way to climax with a guy and that’s okay. After all, when it comes to orgasms, the destination is more important than the route you use to get there.

Give us an O!
Em & Lo

photo by Sara Bjork

When the heartbroken write to us, we usually offer up our patented 10-step program for getting over a breakup. But not even that 99%-guaranteed method sounds like it’ll work on this sad and pathetic soul. Help her out, people!

Dear Em & Lo,

I feel stupid to ask, but how do you get over someone? I had a terrible break-up nearly three years ago (he cheated, I couldn’t bring myself to take him back, he moved on to the next girl, and cheated on her too) and nothing I do seems to help. I gave myself a while to wallow immediately after it, and then gave myself a serious pep talk about getting on with things.

I’ve since tried talking about it and writing about it; I’ve gone on internet dates; I’ve made new friends, tried new hobbies, cut my hair, worked hard at my job, volunteered, exercised, travelled, cried. On one occasion I even lost my temper and shouted at him in public for his bad behaviour (not dignified but definitely justified and sort of cathartic). It’s been so long and I still don’t feel any better.

No one interests me, and none of my friends seem to have ever felt like this for such a long period, or seem to understand how awful I still feel — which makes me feel even lonelier. I think about him every day and still see him around, though I don’t ever speak to him. Friends have suggested I move away, but I love my job and the place where I live — it doesn’t seem fair that I’d have to be the one who moves. I don’t understand what I need to do to get over it. There must be something I’m missing, because I’ve tried so hard and I still feel as bad as I did the day it happened. What am I not doing right?!

– Heart Smoothie

What should “Heart Smoothie” do? Advise her below…

illustration via Foxtongue

Dear Em & Lo,

I love my boyfriend very much, but he comes so early on that I’m left hanging. Receiving oral sex ahead of time would sure get me that orgasm, but he doesn’t even do that! I NEVER orgasm, because as long as he gets his, it seems to not bother him that I don’t get mine! Totally ridiculous!

– Blue Walls

Dear Blue Walls,

It seems to us that your problem is not with your orgasm but with your boyfriend. If he’s not bothered by your lack of orgasms, then we’d humbly suggest that you not bother with him. Period. (Tell him you’ve found someone who’ll go down on you at the drop of a hat…er, push of a button.) If that seems too extreme for you, we suggest experimenting with other “inspirational” measures. For example, would he be bothered by a lack of blowjobs? Then try going on an oral sex strike.

Along with the strike — a plain old sex strike would work, too — we recommend a big Talk. (In fact, if we’re being mature, we’d recommend going with the Talk first and saving the strike as a last resort.) Tell him how much orgasms mean to you — we’re guessing he likes them pretty well himself, so this should be easy for him to understand. Tell him that there’s really one easy way for you to achieve said orgasms. Tell him that it’s physically impossible for you to do this to yourself — draw him a diagram if necessary. Then ask him, ever so gently, why he won’t do it.

If his answer is that he just doesn’t like it — or just doesn’t want to do it — then you’ve either got to compromise on another non-oral way he can make you climax or (back to option one) dump him because you’re just plain sexually incompatible. If he has a more reasonable explanation — he doesn’t know what to do, for example — then you’re already on your way to a solution. Here are some earlier posts from this site that may enlighten you:

• Wise Guys: Why Aren’t Some Men Up for Going Down?
• Wise Guys: Do Men Appreciate Oral Sex Directions?
• How Can I Smell and Taste Better Down There? *

*Note: This may be his excuse for not going down on you. If he’s simply squeamish about the taste of healthy vagina, then we’re back to the deal-breaker thing: You’ll need to ask yourself which you care more about, the man, the oral, or the orgasm? If you’re not ready to kick him to the curb yet — and you suspect that he may have a point — then the advice above may help. Keep in mind that he’s entitled to his own sexual preferences (maybe he’s fingers are more deft than his tongue), but not caring about your orgasm at all shouldn’t be one of them.

And if none of this works? Your mother may have told you once that there are plenty more fish in the sea. What she probably didn’t tell you is that plenty of those fish enjoy cunnilingus a hell of a lot more than your boyfriend does.

Hoping you get yours soon,

Em & Lo

photo by M31.

Can sexual compatibility improve over time in a relationship — or does it need to be there from the start for the relationship to work? Is bad sex necessarily a deal-breaker? Read the letter below and then advise “Underwhelmed” in the feedback section below.

Dear Em & Lo,

I’ve always been a fairly promiscuous woman, in between looking for Mr. Right, and I’ve enjoyed most of the sex I’ve had, and consistently gotten rave reviews. I’ve never had a shortage of lovers and only rarely found myself sexually incompatible with someone. I’ve got some skills.

And I was thrilled this year when I met someone with whom I actually connected emotionally, and really felt excited to be around, talk to, and spend time. I was excited and turned on by him physically and emotionally.

So I was pretty shocked to find that the sex is insurmountably bad. I’m excellent at giving head, and approach it with gusto, but around his cock my bag of tricks doesn’t seem to work. I’ve had guys who were too small for me, but this guy is actually WAY too thick. To the point that there are very few positions we can use and when I get close to orgasm and start to clench down a bit it actually hurts him a great deal and we have to stop. He probably only comes about 30% of the time.

I’ve never had a sexual relationship like this. With anyone else I would’ve just chalked it up to weird sex issues and gone on my merry way to the next dude but I don’t often fall into a “boyfriend” space with someone and I am crazy about this guy. He’s introduced me to his family, we’ve talked about moving in together. It’s clearly “going somewhere” but I know that if the sex doesn’t actually improve we don’t have a chance. He’s reticent to talk and, frankly, I don’t know how to make myself more commodious, or figure out what will get him off without him TELLING me what to do, especially since the moves and tricks that worked so well on the previous bazillion dudes doesn’t work on the one guy I want to keep around.

How to make myself bigger? It’s not a lube issue. I’m juicy. Just small. How to get him to talk? Should I go back to slutting it up? I’m in my 30s. I’d rather have this work than go back to the (albeit more sexually compatible) anonymous masses.

– Underwhelmed

What should “Underwhelmed” do? Advise her below…

photo by faster_panda_kill_kill

Dear Em & Lo,

So I have this guy friend who I met my freshmen year at college. We used to hang out a lot together and, well, I ended up liking him. The only problem was that he sometimes did not seem to feel the same way towards me. He would flirt back and lead my hopes of one day us being together. We even had a lil thing one drunk night, but in the end he would always get another girl or just call me sister, which I hate.

So, this has been going on for almost two years and I am just about tired of all of this. Every time I try to get myself into forgetting him and succeed, he comes around and I fall again. And every time my heart breaks more and more. I’ve never been the lovey-dovey type girl and I am not one to fall in love, but I think this time I fell and it sucks. I even tried that whole psychic thing and they told me that he is immature and that around June he’ll man up and it’ll work out. But it’s already June and it doesn’t seem like anything is going to be working out and I’m done with waiting.

I actually made up my mind to finally tell him so that I am able to move on and get the closure that I need, but my plan was a failure. There doesn’t seem a way that I can get him alone to tell him. Any ideas on how I’ll be able to do so? And trust me, me telling him we should hang out does not work. We have said that before and we just don’t hang out, not to mention that he is seeing someone and knowing him he is just not going to want to hang out. I am desperate to finally get over him, and in need of ideas, so any that you may have I will gladly welcome.

– Woman Down

Dear W.D.,

Oh dear. You seem to be in what we like to call a unilateral relationship. Kind of like Em’s relationship with George Clooney. You say that he “sometimes did not seem to feel the same way towards me”? (Italics ours.) Um, we hate to break the news, but it sounds to us like he’s never felt the same way towards you. You like him; he enjoys the attention and flirts back. You start falling for him; he initiates a drunken hookup. You want more; he hooks up with someone else. You’re thinking “boyf!”; he’s thinking “sister.” And you’ve been putting up with this for two years?! Girl, it’s seriously time to move on. Read the rest of this entry »

photo by sarahxic

Okay, we admit there isn’t exactly a lot to debate in this week’s edition of Your Call. Clearly this woman should leave her boyfriend, a.k.a. the Biggest Asshole Who Ever Lived. But we wanted to publish this letter anyway because (a) This poor woman needs a public record of all you telling her that she’s better than him and needs to move on; (b) This man needs to be shamed, if only anonymously; and (c) Maybe it’ll make you cut your own partner a bit of slack when s/he forgets to pick up milk on the way home or can’t keep up with the plot intricacies of The Hills. It’s a long one, so grab a snack, and away we go…

Dear Em & Lo,

My on/off boyfriend of 3 years and I have recently split up, for the second time and maybe for good. I fell totally head over heels when I first met him and thought he did too. The problems started the 1st time when he left for work one morning,he left me alone and I went to put his pajamas back in a drawer when I came across a pile of love letters, post cards, etc. The letters were quite intense and the dates they were written coincided with a time he was acting strangely with me because he was scared about his feelings.

He’d recently divorced and has two children. I asked him about it while out at dinner and he denied it, then said it was a one-way thing and that nothing ever happened. I believed him [ED: Oh no you did-n't!] and we sort of moved on, until I found out this woman was married with 3 children and lived around the corner from me.

I threatened to take the letters to her husband but instead let it lie. It was difficult to deal with as they all hung around in the same artsy crowd and there is a 12-year age gap in us, but in time the dust settled until it came to my attention that this girl was in fact best friends with his best female friend (who is also his ex wife’s sister!). They are far too close for comfort, he used to live with his ex wife’s sister and insists that they are not romantically involved and I have tried to be friendly when iIve seen her but cannot help but think that she is only respondant when he is there. She once gave him a lift to a party with his ex-girlfriend and they passed me in the street and he admitted to me that he hid in the back of the car when he saw me. Why do that?

We eventually split up because again he said he was confused about his feelings. I was pretty cut up and shot straight into a rebound relationship, got pregnant and felt as low as ever. I booked in for an abortion, something I am not proud of, as the new guy went back to his ex and I wanted to move on.

I was upset and my ex came to see me. I told him in confidence and surprisingly he was a rock of support throughout and even came to the hospital with me. It was the day after he made a move. [ED: Oh no he did-n't!] I was very emotional and told him I needed space to get my head straight.

Four months passed and we saw each other occasionally in passing and were civil, but I did miss him. After a couple of weeks things evolved and it was like we’d never been apart until I noticed him being secretive with his mobile. I realize I shouldn’t have done it, but after all the upset needed to put my mind at rest. I found numerous texts to his ex wife’s sister, telling her about how I’d gone to him and he’d helped me even though I was pregnant to somebody else.

I was horrified, I felt like I’d been stabbed in the back. I never even told any of my family or friends about the abortion  and now I just feel completely hurt that this woman I don’t even know knows the most intimate details of my life. He keeps ringing/texting to apologize, but now I just don’t know what to do. Please help, an outside opinion is really needed right now!

– Doormat Debbie

Okay, dear readers. Do what you do best…talk some sense into this sweet lady who deserves better!

photo by evil erin

Share your advice for this reader in the comments section below…

Dear Em & Lo,

My parents did not believe in circumcision so they left me natural, and I don’t have any problems with the way I am and I have not had any problems with ladies. But I would like to know what women really think about foreskin or no skin? I ask this because there seems to be a disconnect between what some people say publicly and what they believe privately. Is there a difference between the ethical and the erotic for women?  It’s easy to imagine a woman not wanting to hurt a baby, but might that same woman find circumcised penises more of a turn on? In this PC culture, it can be hard to acertain people’s true opinions. What are the majority of women’s ethical and sexual preferences when it comes to a circumcised or uncircumcised penis — and, more to the point, are those two things usually the same?

– Uncut Collegian

What should Uncut Collegian do? Share your suggestions in the comments section below.