Ouchie Sex Just No Fun

I've been dating a guy for a few months now and we started having sex a few weeks ago. The thing is, he has the longest, skinniest penis ever, and it hurts like hell, like a pencil jabbing me. I really dig the guy though so I want to know how to fix this problem. Can you help?

-- Sara

Kelly Says:

You've got to figure out a way to tell this dude that you want his pencil to doodle more and poke less. Some guys mistakenly think that all women get off the way female porn stars portray pleasure at being rammed and pounded, when really that kind of rougher rhythm feels good only to some and/or at certain pre-peaking moments. If you don't feel you can talk openly about his long and teeny weenie, try getting your message across through actions. Take control of your lovemaking positions by, say, getting on top. Move yourself on his penis in a way that feels good to you -- likely in circular motions or grinding forward and back (rather than squatting up and down). Be sure to make it clear that that's the way, uh-huh uh-huh, you like it, uh-huh uh-huh.

Brent Says:

Repeat after me: ultimately you are responsible for your own orgasm. Of course your partner should be concerned about giving you an orgasm, but he's not a mind reader. The first rule to a great sexual relationship is open communication. So, without telling him that he is a "pencil dick," I'd suggest talking about what types of things you both like sexually. When it's your turn, tell him that you like shallow penetration and describe how to hit your G-spot. That way the focus is on your desires rather than his problem. Secondly, there are many other ways of reaching climax without penetrative sex. Explore your oral options or try some manual stimulation. Unless you're dating Edward Scissorhands, I'm sure he can touch you just the way you like.

Older Woman Seeks Serious Stud

I am a 52-year-old woman typically more attracted to younger men. I find most men my age are 50 going on 80 in every way. I am not interested in younger men for a casual or purely sexual relationship. I am in this dating scenario to connect with someone I can develop a long-term relationship regardless of age. The challenge I am having is knowing when a younger man is serious and comfortable with an older woman/younger man relationship versus those who are just out to play. You would think at 52 I would be able to spot a younger guy who is just in it for sex, but hey, some of these guys are really good. What can I ask up-front of younger men that might help to determine their intention?

-- Glynis

Brent Says:

Here's the thing: if you're in the dating world you're going to run into a few players, no matter what your age. I'm not convinced the guys who aren't in it for the long haul are bailing because of your age. I imagine they are hitting the road simply because they are players. So, how do you spot a player? In my opinion, there isn't one simple answer to that question. Every player works a different angle -- that's why they are so successful. Personally, I think you should just enjoy the sex you are having and look at a long-term relationship as a bonus. But if you really can't get into that frame of mind, the only advice I can offer is to hold out on having sex for as long as you can. Why? The longer a guy sticks around without intimacy, the more serious he is. The downside is that you'll risk scaring off guys who are serious, but think you're leading them on.

Kelly Says:

Some guys assume that all older women in the singles circuit are just looking to get laid. I'm sure you're aware of the names they've come up with for the more desperate portion of this demographic -- cougar, puma, etc. And there are plenty of men out there willing to provide services, in part because of the stereotype that older women are wild, uninhibited and technically savvy in bed. I'm sorry to say the cards are slightly stacked against you in your quest to establish a long-term May-December relationship. But that certainly doesn't mean you should just lie back and accept your hot flashes as the only rush of adrenaline you're going to get in this second chapter of your life. Find out if the guys you're interested in have ever dappled in a Demi-Ashton relationship. Some men specifically seek out the companionship of more mature mates. Even if they haven't, you'll be able to tell from their response whether they're open to something steady and not simply steamy.