Best of Sex Advice

Honestly, we wish we could get out there in the real world and take it upon ourselves teach the sexually dazed and confused masses some hands-on lessons in the secrets of love; we know from painfully awkward experience that all this online sex advice stuff doesn't hold a candle to actual firsthand instruction from bonafide experts. Unfortunately, we've been working very hard on other things lately. So until we get some time off, we'll just leave it to the authority of internet sex columnists to help you through those trying times. Proceed at your own risk.

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Nerve.com, Miss Information:

Know that just as bad as the two-pump chump is the guy who treats his girl's orgasm like it's a lifesaving mission to find her a kidney.

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The Stranger, Savage Love:

Gender isn't just about genitals--the mind is gendered, and some male minds are born into female bodies and vice-versa. While denying civil marriage to same-sex couples is an injustice, a fully transitioned transman--meaning he's got an "M" on his driver's license now, not an "F"--and a woman-born woman are an opposite-sex couple, penis or no penis. If society is going to reserve marriage rights for opposite-sex couples, then you have to let transmen marry their female partners. But a lesbian couple being able to legally marry and keep on grinding their glazed donuts--as long as one of the women gets a double mastectomy, a few hormone shots, and a soul patch--only goes to show how absurd our marriage laws are.

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DearAmy.net, Sex Advice for the Modern Player:

It seems as if the only way my body can discharge built up sexual tension is to cry. As in, I don't orgasm; I cry. I have never been orgasmic (not by myself or with a partner). I think it has something to do with relinquishing control in order to ride out the orgasm. It could also be gender related, but for the most part I enjoy sex - I just tend to block out the aspects of my body that I don't like (such as my chest and lack of a penis). I may add however that there is a certain amount of dissociation that happens, and that I seem to be stuck primarily in my head during sex. I'll also add that I'm pre-hormones.

I realize that you aren't a doctor and can't give me a certified medical opinion. I'm just trying to find out if others out there have had the same experience and see if there's anything I can do to become orgasmic.

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AskMen.com, Dr. Zimmer:

A few years ago, when my brother's daughter reached puberty, his wife decided the best way to educate young girls not to be tempted to have premarital sex and risk pregnancy is for parents to demonstrate to them how to satisfy themselves and their prospective partners via mutual masturbation when they are unclothed. He tells me that it seems to have worked wonderfully well. I'd like to see another point of view on this because our eldest daughter has just reached puberty, and my husband is not so sure about this.

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AllSexAdvice.com, Expert Advice:

This section of the forum calls itself "Expert Advice" and that's what I'm looking for. Here's my 'problem', and be patient:

I've been posting pictures of my wife's big gorgeous breasts anonymously on amateur sites for some years. I don't know why I love letting other men jack off to her tits this way, but I do. Recently, however, when we went to Arizona on vacation just to get away from everyone we know, I asked my wife if she would "be my whore" and wear some very revealing blouses and show off her tits in public. She did it for me, and we bought her some great sheer cleavage blouses and a bathing suit that showed almost her whole breasts! I loved parading her around while men all stared at her big tits, in the lobby of the hotel, at the pool, at a Giants game (Giants were playing in AZ that week). I loved it! Then, we went to Mexico a couple months later with my sister in law and her husband and I asked her to do it again, and I LOVED how my brother in law just stared at my wife's big tits every day, and she seemed to enjoy showing them off everywhere we went.

When we got back from Mexico, I sent a few topless photos of my wife to my best friend via email, hoping he would jack off to her pictures. Then, when he came to my office to go to lunch, I would load one of her topless pictures on my computer so he would see her breasts when he came in.

Now I've been fantasizing about having Jack Off Nights with two of my buddies, where all of us sit on the couch and jack off while my wife stands in front of us and shows us her tits, and lets my friends suckle her while they jack off. (That fantasy led to imagining them fucking her tits and her sucking them off while I watched. I find that fantasy VERY fun. I believe that's called "cuckolding").

A part of me is afraid she'll enjoy this showing off too much and might do it when I'm not there which might lead to her having an affair. (My first wife was a risque dresser and she had an affair).

I'm wondering if my desire to show off my wife's big tits has a name (you know, like "voyeur" or "exhibitionist", a name like that for people who like to show off their wife's tits). And I'm wondering why I like doing this. Most men don't WANT other men looking at their wives.

What's wrong with me and why am I this way?

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PuckerUp.com, Forums:

My girlfriend and i have recently been getting into mild scratching and nipple play when we make love. i was just wondering if there are limits to what you can safely do to your nipples, i read somewhere that pulling or twisting nipples increases likelihood of breast cancer. is this true? is there anything else we should be aware of before we get into this sort of thing?

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AdviceGoddess.com, Amy Alkon:

So, how honest is too honest? Well, if you want your insecure, recently deflowered boy virgin to feel comfy about his place in your life, taking him on a sex tour of your teen years probably isn't your best bet: "Yes, over here we have the infamous janitor's closet, and if you look out the window, you can see the 50-yard line and the long-jump pit...and I'll never forget that night we broke my sister's tree house!"

Yes, let a guy know you used to be kinda wild. As for whether you were with 12 or 20, in the conservatory with Colonel Mustard or in the kitchen with Professor Plum and Mrs. Peacock, it's really none of his business. What's productive in a relationship isn't total honesty, but judicious honesty -- telling somebody what they need to know to know you: what makes you happy, what scares you, and what you want from life, not a moment-by-moment replay of what went on in the back of some delinquent's car.

Even if you were, at one point, vying to be the Charlie Sheen of teenage girls, that doesn't give any guy the right to spend two years punishing you for having more sex than he did. After all this time, your boyfriend's crystal clear on whether it was vanilla or Cirque du Soleil with this one or that one, but he doesn't know you well enough to have a grasp on what matters: Will you sleep around, not did you? Clearly, it's his insecurity, not your ethics, that's the problem. Will that ever change? Probably only if you change boyfriends. Look for a guy who's secure enough to see your past as part of what made you the person he loves in the present. A guy like this understands that the only must-tell sexual history is the important medical and psychological stuff: funny uncles, communicable diseases, and whether somebody's actually lost their virginity or they've just been working really hard to ditch it at the mall.

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SexualHealth.com, Women's Sexual Health:

I have always been sexually active, but my boyfriend has not. He had intercourse for his first time with me, about a week ago. We have had intercourse twice. Our problem is that his penis keeps slipping out while he is pumping me. we have tried several different positions, and nothing seems to help.Even doggy style it kept slipping out! Could it be because he is just inexperineced, or could his penis be too small? He will just get it inside me, and it keeps slipping out. Any ideas on why this is happening?

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Scarleteen.com, Advice:

I'm 14 years old and a Freshmen in highschool. I've never experienced intercourse, but I have experienced other sexual acts before such as oral sex (being ate-out), and being fingered. During these acts, I have experienced orgasms, so it's not a problem for me to have one. As a matter of fact, they come quite easily for me. But for some reason, I still "come" everyday, even when I'm not being aroused. It happens when I'm just innocently kissing a guy and my pants are wet with it when I come home from school everyday. I haven't had any sort of sexual experiences for about 3 months now. But it's still happening. My former boyfriend, whom I had these experiences with told me that it's perfectly normal and that my brain just probably thinks that whenever I feel slightly attracted to someone, some sort of sex is going to follow so my body starts preparing for sex by coming. I want to know if this is correct and why I continue to "get wet" so often when I'm not even having regular orgasms.

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SexualHealth.com, Men's Sexual Health: