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Hello Ladies,

I am a married guy who occasionally reads your site for some ideas to share with my wife.  It seems like anal play both for him and her is a popular topic. My wife enjoys some occasional backside attention, and I’ve been trying to get her to give me some too. One time she used a butt plug on me while giving me a handjob. This resulted in the most intense orgasm I had ever experienced!  After that, I secretly used her dildo on myself just to see if it would fit, and it did. Now, I’ve asked her to use it on me, but she’s afraid of hurting me.  I don’t want her to freak out knowing I’ve already done it. Do you have any advice as to how to get her to play along?

Thanks!
Swimdad

Dear Dad (no wait, that’s all wrong…),

Have you heard of those urban legends of people getting their vacation camera film developed only to find pictures of their toothbrushes stuck up strangers’ butts? Well, this is practically the same thing… Read the rest of this entry »

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 on the letter below by leaving your advice in the comments section. 

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Dear Em & Lo,

So I met this guy clubbing and we ended up at a motel and got it on. I was expecting a one-night stand, but he asked if I wanted breakfast and the conversation was great and it lead to a next date with no sex.

For a few weeks he called and texted and we were sort of dating, though we never defined anything (on my birthday, he came with a present and a card). Then about a month after that, I realized he was losing interest. I was into him, so had “the talk,” and I decided to call it off — he seemed to understand, but no objection.

Then about 2 months after that, I called him and we met for drinks and it turned into a booty call. I felt a bit sad as I still had feelings, but he didn’t seem to. A month later, I drunk-dialed and we met and just did our thing. Then again last week. I now know why I am meeting up with him — it’s no longer for a relationship, I think it is because I like to be intimate with HIM and am currently not seeing anyone.

I wanna keep it less frequent but have ground rules, like, only when we are single and such. Also, all the booty calls were made by me and he would come to me. I sort of like it that way, as it is upon my convenience, but also wonder why he would not? I’m also scared that if I even bring up any kind of talk to define anything, he will will just vanish.

Some friends say to stay away as he doesnt seem to value anything. I dunno what to do… just forget it until I am in the mood again… is he not even f-buddy material?

– (A Different Kind Of) Rules Girl

What should Rules Girl do? Leave advice for her in the comments section below.

MORE LIKE THIS ON EMandLO.com:

• How Do I Know When It’s Time for “The Talk”?
• What Turns a Hook-Up Into a Girlfriend?
• How Can I Tell If a Guy Is Playing Games?

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Dear Em & Lo,

I’ve known this girl “Ashley” since high school band eight years ago. We instantly hit it off as friends the day we met because of our mutual liking of illegal substances. I know it’s cliche, but I’ve had a crush on her since our first band practice together. She has stated many a time how I’m her “best friend.”

However, this past summer we hooked up when both of us were mostly blacked out. That is, we both remember the initial make-out session but don’t remember how we woke up in the same bed. We also have yet to directly talk about that night. In addition, we hold hands in a “more than friend way” whenever we walk somewhere while inebriated.

Currently, I live on the East coast and she lives back home, for us, in the Midwest. I’ll be visiting her next month as a part of my spring vacation.

My questions for you are as follows: What are your thoughts on very good friends trying to become more than friends? What are some signs that one friend might have strong feelings for the other friend and, in your experience(s), is it worth it when two good friends try to date?

Thanks for the help,

Best Friend Wants More

Dear B.F.W.M.,

You had us at “high school band.” At least, you had Em, who suffered numerous heartbreaking unrequited crushes in her high school band.

Anyway. Hard as this might be for you to hear — given that you and Ashley bonded over illegal substances, only hooked up after blacking out, and only hold hands when you’re drunk — you’re going to have to approach this sober. In the cold, sober light of day, you’re going to have to ask out your friend on a date. The only way to know for sure is to be 100% blunt about it. We recommend actually using the D-word, as in, “Would you like to go on a date with me?” Your question has to be 100% obvious so that her response actually means something. (Meaning, if you ask her out to the movies and she says yes, that doesn’t count, because she might think of it as a friend-date.)

If she says yes — bingo! It’s true love, Hollywood-chick-flick-style all the way. And if she says no — actually, hopefully she’ll be a bit kinder and will use the excuse of long-distance — then you have your answer and you can move on and find true love, drunken hook-ups, and romantic hand-holding opportunities with someone else.

Seriously, it’s that simple. (And that fucking terrifying. Sorry.)

Cojones!

Em & Lo

MORE LIKE THIS ON EMandLO.com:

• What Turns a Hookup Into a Girlfriend?
• How to Buy (or Accept) a Drink
• Top 10 Worst Lines in Rom-Com History

photo via flickr

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 on the letter below by leaving your advice in the comments section. 

Submit Your Own Question to EMandLO.comTry Our New
*PRIVATE* Advice Service!

Dear Em & Lo,

Five-ish months ago, I broke up with my first boyfriend. Obviously, there were problems, but it was a really significant relationship. And, there were some really great things about it: the sex; the emotional and intellectual chemistry; feeling sexy, attractive, and flirty; etc.

About two months post-break up, I figured it was time to re-enter the dating pool. I didn’t want to lose the “I’m sexy, attractive, and flirty” feeling I had in the relationship. But, the more I dated, the more crazy, desperate, and insecure I became. Also, the more I dated, the more I missed the ex. I figured it was in my best interest to stop dating, truly get over the ex, and be alone until I was okay being alone.

I sort of miss the ex from time to time, but that’s pretty much over. However, I really hate this being alone stuff. So, my question(s) for you is this: How do you re-enter the dating pool? How do you get out of the I’m-lonely-and-just-want-someone-to-cuddle-with phase and back into the how-many-men-can-I-seduce-tonight mode?

– Water Wings

What should W.W. do? Leave advice for her in the comments section below.

MORE LIKE THIS ON EMandLO.com:

• How Do I Know When It’s Time for “The Talk”?
• What Turns a Hook-Up Into a Girlfriend?
• How Can I Tell If a Guy Is Playing Games?

Get Personal Advice Publicly on EMandLO.comTry Our New
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Hi Em & Lo,

So I’m a freshman in college and I have never dated before or even been kissed. Sometimes I really feel like I’m missing out. I’m pretty friendly, but is it bad that I still haven’t had a relationship yet? What should I do? Help!

Sincerely,

Never Been Kissed

Dear N.B.K.,

Regular readers to this site will know that we’re pretty prudish when it comes to talking about our own sex lives. For one thing, we think it’s a mistake to assume that what’s true for us will be true for you. And for another, we’re prudes! There are plenty of other sex columnists out there willing to bare it all (sometimes quite literally: We once saw Tristan Taormino insert a butt plug live on stage!), and more power to them. That’s just not our bag.

That said, we’ll make an exception today. This is from Em:

I didn’t have my first kiss until the summer before I went off to college, so I had barely been kissed when I showed up as a college freshman. I never dated in high school, never kissed anyone, never locked braces with anyone, never spent seven minutes in the closet with anyone (or whatever that game is that everyone else seemed to play and I only read about in Judy Blume novels). And it wasn’t like this changed overnight when I showed up on campus, either — it wasn’t until the very end of my freshman year that I had my second kiss (for the record: kind of disappointing).

Sophomore and junior years led to a few more disappointing hook-ups, and it wasn’t until my senior year that I actually dated someone.

Sure, at times I felt like I was missing out. At times I wondered what was wrong with me. At times I was convinced that if only I didn’t struggle with acne and debilitating shyness, I’d be the belle of the ball. But looking back, I’m pretty sure I didn’t miss out — in fact, I don’t know anyone who particularly enjoyed dating in college (or “dating” in college, a.k.a. drunken hook-ups).

You’re young! It’ll happen! Maybe this year, maybe next year, maybe not until after college, who knows. Don’t rush it, don’t let anyone make you feel like a weirdo, and definitely don’t drink heavily to try to make it happen (worst idea ever, I can report).

And yes, eventually I did have a second relationship — after college. I had a bunch more, in fact — some good, some bad, some indifferent. I got my heart broken once and my ego hurt a hundred thousand times. And then I fell in love and got married.

I’m pretty sure I didn’t miss out on anything wonderful — in fact, I’m pretty sure that my college experience would have been way less fun if I’d been hooking up on a regular basis.

In the meantime, just try to enjoy everything else that college has to offer. (You have no idea how many times we say to each other, “I just want to go back to college and actually appreciate it.”) A cappella group singing, anyone?

On your side,

Em & Lo

MORE LIKE THIS FROM EMandLO.com:

• Dear Em & Lo, I’m a Thirty-Something Virgin – Help!
• Dear Em & Lo, How Far Should I Go to Keep a Guy?
• Confession: Losing Your Virginity Ain’t No Big Thang
• The Virgin Diaries

photo via Flickr

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 on the letter below by leaving your advice in the comments section. 

Submit Your Own Question to EMandLO.comTry Our New
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Been married for thirty-six years and when we have sex he is really amazing. The problem is we have sex only once every 1 to 2 years! It has always been sorta few and far between.

This is what really bothers me: he says it has to be when he is ready, when he is in the mood. Believe me, if it was when I wanted it, it would be at least twice a month.

How can I get him to realize that sometimes it makes me feel like my opinions or feelings do not matter to him?

— Blue Box

What should B.B. do? Let her know in the comments section below.

MORE LIKE THIS ON EMandLO.com:

• Are Men Really Romantic Or Do They Just Fake It?
• 5 Ways That Getting Kinky Can Improve Your Relationship
• If He’s Being Secretive, He’s Either a Spy or a Player

photo via flickr

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Yesterday we answered a thirty-something virgin’s plea for help. Today, we tell her and this woman and virgins everywhere whether they should tell the first guy they’re going to have intercourse with that they’re still carrying their V-cards:

Dear Em & Lo,

Do I have to tell a guy I’m hoping to do it with that I’m a virgin?

–Sandra Dee

Dear S.D.,

Yes and No.

Here are the conditions that require a “Yes” answer to the above question (more than one may apply, but only one is neccessary for a “Yes”):

• If you’re hoping to have a relationship with this guy. You want to try to build a good relationship with this person? Then you should be open and honest about your situation — that’s what good relationships are built on, openness and honesty! And if he feels the same way about you, he’ll want to know.
• If you want to make sure you’re having sex with a man who would not consider virginity a deal breaker. Telling him is a way to weed out anyone who doesn’t want to take the time to make it special, can’t handle the pressure, is afraid you’ll fall too hard for him, etc. But don’t worry, not every guy feels this way, so you won’t be a virgin forever — there are plenty of men out there who will be over the moon to discover you’ve never done it before… because you’ll have no one to compare him to!
• If you want the experience to be as good as it can be. You’re going to have a lot of sex in the years to come, both good and crappy, but you’re only going to lose your virginity once. So why not try to make it special? We can’t guarantee that the earth is going to move for you the first time — in fact, for women, the first time is rarely orgasmic, and it’s often downright crappy. But that doesn’t mean that you shouldn’t even try to make it a bit special. If a guy knows it’s your first time, then he’ll be able to help you celebrate the occasion by going very slowly, paying extra special attention to the niceties like soft lighting and good music (so that you won’t have to remember for the rest of your life that you did it the first time with NPR’s “Fresh Air” playing playing in the background), and basically just being uber-attentive to your responses. (In an ideal world, your first time with any new partner should be like this, but damn it, we don’t live in that kind of world!)
• If he flat-out asks you. We can, under the right circumstances, condone a little reticence on the topic of your virginity, but outright lying in bed is for losers who don’t like orgasms.

Here are the conditions that might warrant a “No” answer (all of them should probably apply before deciding not to tell him):

• If you don’t care whether you see this guy again. If you see this as a one-night-stand kind of thing, with not a lot of emotion invested in it, then we guess you could just not mention it.
• If you just want to get it over with as fast as possible. If you don’t want to build it up too much, if you want to take some of the pressure off, if you want to be in the moment and not complicate things, then you might not bring it up.
• If you’re afraid the news of your virginity will scare him away. We’re not going to lie: Some guys won’t want to take your V-card. That’s a lot of pressure on a guy — for example, if he’s just thinking of this as a casual fling, then he may not want to be your first, as he might worry that you’ll get too attached. Probably not the most sensitive type of person to lose your virginity to, but maybe that doesn’t matter to you at this point.

If it’s not glaringly obvious, we strongly favor the “Yes” answer to this question. We think you owe it to yourself  – and to the guy — to fess up. Regret is possible with either approach, but we think your odds of big regret are greater by not telling him.

Whether you decide to tell or not, before you do it, do yourself a favor and read a good book about sex. Like, oh, perhaps our book Sex: How to Do Everything, to pick one totally at random. Seriously, though, a book like this will teach you the way around your own body, it will help you discover the various routes to your happy place, and it will give you a few ideas of what to ask for when you do find the right man. Because you should never expect any man to have all the answers when it comes to your orgasm.

Have fun storming the castle!

Em & Lo

MORE LIKE THIS FROM EMandLO.com:

• Dear Em & Lo, I’m a Thirty-Something Virgin – Help!
• Dear Em & Lo, How Far Should I Go to Keep a Guy?
• Confession: Losing Your Virginity Ain’t No Big Thang
• The Virgin Diaries

photo via Flickr

Get Personal Advice Publicly on EMandLO.comTry Our New
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Dear Em & Lo,

I’ll get straight to it: I’m in my early thirties and I’m a virgin. Not really by choice. It’s just never happened. It’s gotten to the point where I’m so worried what potential dates (and even platonic friends) will think if they find out, that I’m afraid it’s holding me back and I’ll end up dying along. It’s really starting to depress me. Help!

– Pre-Cat Lady

Dear PCL,

It’s great to wait for the right person for such an important life event. We’d even recommend waiting for love, however long that takes! But if you’ve made it to your thirties without making at least one serious connection with a like-minded human being–and you want to make this connection–then you’ve probably got some issues that need to be dealt with in therapy.

Do you have some social interaction problem–fatal shyness, insecurity, social ineptness, a mullet–that is preventing you from meeting people? Have you built up sex (and the person who gives it to you) to be this great, big, overwhelming, all-powerful, awe-inspiring ideal that can never be achieved unless the stars are aligned just so? (Prepare to be disappointed.) Are you a sexual person who has sexual desire and masturbates regularly? If not, you may have a hormonal situation that could be dealt with medically, or else perhaps you subscribe to an incredibly repressive religion that guilts the sex drive right out of you. Or perhaps you just think that nice girls don’t. (For the record, nice girls do.)

Whatever the case, it’s not the virginity holding you back–you’re holding you back. And it’s going to take some serious self-reflection to get to the bottom of why you’re not meeting people you’d even consider doing. Then it’s going to take some serious motivation to make the necessary changes to meet people you do want to do. Once you do that, read our advice on whether or not to tell him you’re a virgin.

Nice girls,

Em & Lo

MORE LIKE THIS FROM EMandLO.com:

• Dear Em & Lo, How Far Should I Go to Keep a Guy?
• Confession: Losing Your Virginity Ain’t No Big Thang
• The Virgin Diaries

image via flickr

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 on the letter below by leaving your advice in the comments section. 

Submit Your Own Question to EMandLO.comTry Our New
*PRIVATE* Advice Service!

I have been single for several years. I am a divorced forty year old woman with an almost 18-year-old son. I’ve been divorced for 7 years and have only been in one serious relationship and have had 2 short lived “flings” and now this. I’ve been seeing a 30 year old guy (single, never married, no kids) for about 4 months now.

Firstly, I don’t know how to date. Early on I freaked out because I was developing feelings and got scared and had a meltdown. We talked it out and I put all my feelings out there and since then I have just tried to be honest about how I feel. I haven’t played the game of playing hard to get or any of that. If I want to see him or talk to him I contact him and tell him.

He is a very reserved guy and likes a lot of alone time to himself. For the most part I am good with that.We have talked about how I feel when I want to see him and he declines and he has told me that I should not take it personally because he works two jobs and he does require alone time and it has nothing to do with me.

But my feelings are deepening and I want to have “the talk” with him to see how he feels about me. Lately I feel like he is keeping me at a distance more than when we first started seeing each other. He used to initiate spending time with me more than he does now and I don’t know what to do because it makes me feel sad and insecure about everything.

He previously had told me with his past relationships that at the 6 month point he figures he should know if the realtionship is going somewhere.(None for him have lasted more than six months since a 3 year high school relationship.)

My question is, do I have the talk with him now because my feelings get hurt when he doesn’t want to see me and I really just want to know where we are, or do I wait a couple of months and give him his space and see what happens? I don’t want to scare him off, but I do want to know how he feels, because I know how I feel and I want to get closer to him…and get out of my head because I want to be with him and when he doesn’t contact me for a day or two or declines seeing me if I ask to get together I get hurt and confused because I don’t know how he really feels and I’m not sure what to do.

Like I said, I don’t want to scare him off so I wonder if I should just hang in there and see what happens or just force the issue for better or worse so at least I know what’s up. Help?!

– Tongue-Tied

What should T.T. do? Let her know in the comments section below.

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Submit Your Own Question to EMandLO.comTry Our New
*PRIVATE* Advice Service!

Dear Em & Lo,

I have been acquaintances with this man for about 3 years, but recently (within the last few months), he started talking to me more and we’ve been talking regularly since then. Because of his behavior and some things he has said to me, everyone thinks he has a thing for me and I get that impression from him too. At first I chose to ignore it because he is around 35 years old (not sure of his exact age) and I’m only 22. However, lately I’ve been finding myself more and more attracted to him as we talk and joke around with each other.

I usually do date guys who are a little older than me, but I’ve never thought about dating someone a decade or more older. I know people get crushes all of the time and you don’t have to act on every crush you have… I’ll admit I’m not sure how I feel about the age difference. Is this something I should pursue or should I just let it go as a simple crush and nothing more?

– Miss May, Crushing on Mr. December

Dear M.M.C.O.M.D.,

Go for it! You’re twenty-two, what the hell do you have to lose? Just keep things light and fun and don’t lose your sense of self or your idea of what you want and need out of a relationship. Be just as demanding or flighty as you would be with  a twenty-two-year-old guy. It’s easy to let an older guy take the lead, just because he’s, well, older — but trust us, he’s not necessarily wiser.

In fact, this might be the only time you actually enjoy dating a thirty-five-year-old guy. Because when you get to your thirties yourself — should you find yourself still dating — thirty-five-year-old guys may well drive you crazy (and not in a good way). And yes, this is in no small part because of their continued obsession with dating twenty-two-year-olds despite a stated desire to get married and have children with a woman who is their equal in everything from intellect to life experience.

Not that we’re bitter or anything.*

- Em & Lo

* Seriously, we’re not bitter. Probably because we’re both happily off the dating market!

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