‘I’m a man in love with a woman half my age.’

Dear Dan: I’m a 40-year-old guy with a 30-year-old girlfriend. We’ve been together a year, and I can see a future with her. But there are problems. This girl comes after two minutes of stimulation, be it manual, oral, or penile. As someone who takes pride in my foreplay/pussy-eating abilities, this is a bummer. She gets wet to the point where all friction is lost during PIV and my boners don’t last. It’s like fucking a bowlful of jelly. Part of me is flattered that I get her off, but damnit I miss a tight fit! (Her oral skills aren’t great, either, so that’s not an option, and anal is a no-go.) I love to fuck hard, and that’s difficult when I’m sticking my dick into a frictionless void. Is there a way to decrease wetness? Help, please.

Can’t Last Inside Tonight

Dear CLIT: First things first: She’s not doing anything wrong, CLIT, and neither are you — at least you’re not doing anything wrong during sex. (When you sit down to write letters to advice columnists, on the other hand…) She can’t help how much vaginal mucus she produces or how much vaginal sweating your foreplay/pussy-eating skills induce, any more than you can help how much pre-ejaculate you pump out. (Her wetness is a combo of vaginal mucus and vaginal sweating — not a derogatory expression, that’s just the term for it.) And all that moisture is there for a good reason: It preps the vagina for penetration. In its absence, PIV can be extremely painful for the fuckee. So the last thing you want to do is dry your girlfriend up somehow.

Now here’s something you are doing wrong: “It’s like fucking a bowlful of jelly,” “I miss a tight fit,” “Her oral skills aren’t great, either,” “I’m sticking my dick into a frictionless void.” You’re going to need to have a conversation with your girlfriend about this, CLIT, you’ll need to use your words, but you can’t have that conversation — not a constructive one — until you can find some less denigrating, resentful, shame-heaping words.

Again, she’s doing nothing wrong. She gets very wet when she’s turned on. That’s just how her body works. Too much lubrication makes it harder for you to get off. That’s how your body works. And this presents a problem that you two need to work on together, but insults like “bowlful of jelly” and “frictionless void” are going to shut the conversation down and/or end the relationship. So try this instead: “I love how turned on you get, honey, and I love how wet you get. But it can make it difficult for me to come during PIV.”

If you don’t put her on the defensive — if you don’t make her feel like shit about her pussy — you might be able to have a constructive conversation and come up with some possible PIV hacks. If there’s a move (clitoral stimulation) or an event (her first orgasm) that really opens up the tap, CLIT, save that move or delay that event until after you’ve climaxed or until after you’ve reached the point of orgasmic inevitability — if PIV isn’t painful for her when she’s a little less wet.

You can also experiment with different positions to find one that provides you with a little more friction and doesn’t hit her clit just so — perhaps doggy style — and then shift into a position that engages her clit when you’re going to come. And there’s no shame in pulling out and stroking yourself during intercourse before diving back in. Be constructive, get creative, and never again speak of her pussy like it’s a defective home appliance, CLIT, and you might be able to solve this (pretty good) problem (to have).


Dear Dan: I’m a woman in an open relationship of four years. I adore my partner. When we were first dating, it was casual and there were no ground rules. During that time, I slept with a guy without condoms after he cornered me in a motel room. One of the biggest rules in my current relationship is to use condoms with other partners. My current partner has made it clear that he would consider exchanging fluids with someone else cheating. I’m worried he’ll somehow find out about that night in the motel room, and I feel bad keeping it a secret. If I tell him, there’s a chance that our relationship will end and I’ll be living in my car. What should I do?

Burdensome Unbearable Guilt Sucks

Dear BUGS: This thing happened — or this thing was done to you — before you made a commitment to your current partner, BUGS, and before ground rules were established. I’m assuming you got tested at some point over the last four years; failing that, I’m assuming neither of you has developed symptoms of an STI over the last four years. (And condoms don’t protect us from all the STIs out there, so even if you did come down with something, your partner could have passed it to you.) So cut yourself some slack, BUGS: You had unprotected sex under a sadly common form of duress. Fearing something much worse, you “agreed” to unprotected sex — you agreed but didn’t freely consent to unprotected sex. Too many men don’t understand that kind of fear or the de-escalation techniques women are forced to employ when they find themselves cornered by threatening men — de-escalation techniques that can include “agreeing” to but not freely consenting to sex, unprotected or otherwise. You’re under no obligation to tell your current partner about that night, as it took place before you established your ground rules, so it’s not really any of his fucking business. And if homelessness is a potential consequence of telling your partner how you were pressured into sex you did not want, then you’re lying to him now for the same reason you went bare with that asshole back then: duress.


Dear Dan: I’m a man in love with a woman half my age. We met shortly after I had to leave the city I was living in to escape a toxic relationship. I know this girl has feelings for me. My gut screams it. We also share a strange connection. It’s something I know she feels. She simply can’t help being tied to the energy I’m feeling. A while back, I hurt her. Unintentionally, but it hurt just the same. I was still not over my ex and very leery of ever experiencing that kind of pain in my heart again. The problem now is that this young woman won’t acknowledge her feelings for me. She swears she never had feelings for me. We found ourselves alone one day, and her actions were clearly indicating that she wanted to have sex with me but her words prevented me from taking the opportunity. How can I reach this girl? She knows I love her. I know I’m not wrong. She wants what I want. This love is not something I chose and I’m beginning to resent it.

In Lasting Love

Dear ILL: You are wrong. She does not want what you want. Your gut is lying to you. She is not in love with you. You do not share a connection. You need to listen to her words. She is not tied to the “energy” you are feeling. You have got to stop thinking with your dick. She was probably scared out of her wits when you managed to “find” her alone. You cannot reach this woman. She can sense your resentment and she’s afraid of you. In all honesty, ILL, I’m afraid of you. Just as this poor woman most likely fears becoming one of the many women murdered every year by men they’ve rejected, I fear being the messenger who got shot. But you asked for my advice, ILL, and here it is: Get into therapy. You need help. And my advice for her, if she sees this, is to do whatever you must to protect yourself — up to and including moving away.


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