Entries Tagged 'He Says, She Says' ↓

Doug Dalton is a good friend and guest blogger who happens to be in “new relationship phase,” so of course, we wanted to get the juicy (and awkward) details from him on how it’s going. Doug eats, drinks, and dates in San Francisco, though he is most successful with the drinking.

In my last post on first-time sex with a new partner, I described the male orgasm as a foregone conclusion. For most men, if we’re having sex, then it’s going to happen, and often much sooner then we would prefer, tell our friends, or have led young ladies to believe. Conversely, my experience has been that the female orgasm is no guarantee, and often elusive. Many a woman (how many I care not mention) has not reached orgasm via intercourse with me, but luckily it’s been common enough to spare my ego.

For most men, their own orgasm is important, but bringing a woman to orgasm is also important. It signifies the completion of something and results in a sense of accomplishment and mutual satisfaction. Don’t get me wrong, men are not waiting for Alfred Nobel to show up at the front door, but the idea that something is happening as a direct cause of one’s own actions has a nice quality to it that most people (not just men) can appreciate.

To put it bluntly: making a woman cum is hot, and guys like it. If only it were easy.

Recently I became sexually active with a woman who I have not been able to bring to orgasm via intercourse. This is the result of more than one thing likely; some mix of me and her. Maybe it’s just me, who knows? And that’s the kicker. “Who knows” is the wrong question. “What is the best way for me to work with her to get her to orgasm” is a better question, and the answer will require “a talk.” Communicating about sex is the only way that will lead both you and her to what is hopefully a shared goal.

Waiting to stumble upon the answer will not work. It certainly didn’t work with other women. Save stumbling for your web browser. By having a conversation about her orgasm, a few things can happen.

• You will let her know that you actually care that her physically needs are being met. This alone may make her feel more comfortable and open around you. You may also find she is relieved or excited to talk about it. Neither of those seem like bad things.

• You might get some instruction out of it. Let’s be honest - a road map would be nice. While vaginas are shaped similarly, they don’t all work the same way. And, boy, you can get lost once in a while.

• She might tell you that she can’t orgasm from intercourse alone. Period. That’s not to say it isn’t a worthwhile endeavor, but at least it let’s you know where to prioritize your efforts. That’s why it’s never a bad idea to be good at going down on a woman, and be open to other ways of getting her off.

So that’s what I am going to do – talk to her about it. And if I wasn’t such a pussy, I would even bring it up sober. Luckily for her and the liquor industry, that won’t happen. With any luck, I’ll be writing, “what happens when you make a girl cum too much” soon.

Doug Dalton is a good friend and guest blogger who happens to be in “new relationship phase,” so of course, we wanted to get the juicy (and awkward) details from him on how it’s going. Doug eats, drinks, and dates in San Francisco, though is most successful with the drinking.

The background: you have successfully woo’d her. A few nights out for cocktails, a nice dinner or two, and she likes you. Against all odds, you have convinced her that you are not a total scumbag, and that you are sexually attractive or, at least, sexually acceptable (either will do). You have followed the base path taught to you so many years ago, which, while funny, is actually the pattern you follow every time: kissing (french), boob touching, then vagina, and finally sex. This base path is the Esperanto of making out, except it is actually accepted by most.

The setting: Now back at your place (or hers), you are going to do it, for the first time. How do you know when it’s that time? Well…that’s a different post. For the purposes of this, we will assume you are pretty, totally, almost completely positive sex is going to happen.

The challenge: Most every man takes for granted that he is going to cum during sex, and I think most women expect that, too. Beyond this straight-forward biological reality, you have a goal: pleasing her. Pleasing her, though, is actually a complex union of goals that include giving physical pleasure, boosting your ego, exciting her, and making things interesting, all while not horrifying her. For those of you who believe in the cliché that men have a one-track mind, I assure you there is a lot more going on up there than you think.

The analysis:  Since your own pleasure, to some degree, is a given, pleasing her becomes a complicated and even distracting pressure. There are a number of reasons for this, many of them selfish, but all are part of what’s going on in your head during the sexual encounter. Here are some of the reasons pleasing a woman is such a challenge:

• You want her to enjoy it. The first reason is simple – you want her to enjoy it. If she doesn’t like this, then you don’t get to ride again, er, unless you are either rich or one hell of a charismatic motherf*cker. Thus, pleasing her is important and openly intimidating.

• You feel inadequate. Thoughts of inadequacy, while not rushing to the front of your brain, do linger in the background like the guy no one exactly knows at the party who keeps stealing beers from the keg. It might be about size, experience, or endurance. Questions run through your head like, “What was the last guy doing? Was he more fun, more open, more forthcoming physically?” Knowing that you’re probably an average lover and not too much more doesn’t help, even if it does put you in the middle.

• You want to be an amazing lover. Admittedly, this is pure ego, but as a man the concept of satiating a woman to the point of either fainting, gasping for air, or paralytic nirvana is a goal worth attaining, or at least dreaming of attaining. You want her (when she finally comes to) to announce to the world (starting with her friends) exactly what a sexual beast you are.

• You want to stand out. Beyond just pleasing her, you want do something more. You want to give her a little something to separate yourself from the others, as well as to excite yourself.  It could be anything, a solid ass squeeze, rough on the boob grab, nibbling, some sort of hip twist… who knows. But we all do something that, while we wouldn’t call it “patented,” we can recognize as falling onto the “extras” menu. It’s off the base path and hopefully therefore exciting to her and adventurous for you.

• You don’t want to be too “deviant” the first time, though. Is a thumb in the butt too much? Fine, a jaunt off the third base line is great, but might it horrify her? While you want to please her and be exciting, you don’t want to horrify her. There are some things you don’t want to ask; you would rather just do and roll the dice. Maybe she is a gambler, maybe not; finding out can be fun and a bit of mischief.

In the end, when you are both lying on your backs, realizing how late it is and that you are going to have a hangover in the morning, you can look back and reflect. Reflect on an evening that was just like you thought and nothing like you thought. You realize you probably didn’t come close to pleasing her, and the thing you thought was going to be cool and exciting turned out to be blunder-full and awkward. Strangely, you are pretty sure she will have sex with you again. Hopefully someone will write a post “Girl’s Perspective on having sex with a new guy for the SECOND time” because that is the real mystery.

Happy HNT, in the holiday spirit!

With Christmas just around the corner, many out there are wondering whether they’ve been naughty or nice this year. Holly and Jason are tackling the issues that Santa just won’t touch, to give you a heads up on whether you should expect delightful presents under your tree or a lump of coal in your stocking.

Vibrators & Dildos: Holly Says

I have a girlfriend with quite a stash of sex toys who started dating a man. He did not like her toys. Like the beloved dog that she let sleep in the bed, the sex toys were an unwanted competitor for her affection, or so he thought. He whined like a jealous lover, denied her vibrating pleasure, and delivered an ultimatum: the toys go, or he goes. And so he went, to the lost & found box of unwanted boyfriends.

While vibrators and dildos are not exclusively for women, I suspect that jealousy or insecurity about them is exclusively male. Many a man has felt a little insecure because he did not vibrate at a particular frequency or grow to 12 inches in length. So if you have a guy who is a little insecure when you pull out your toy box, are you a naughty or nice girl if you keep playing with them?

I suspect Santa would say:

You’re nice if . . .

• You’re learning your body. Many women struggle to orgasm. Vibrators and dildos are good tools to experiment with to figure out your body and what brings you pleasure.

• You’re maintaining a healthy solo sex life. Coupled up or not, a woman can have a healthy solo sex life. Toys are a good way to get off when you’re single, and even better to use when your beau is not available.

• You share. There’s a lot of ways he can play with your toys, too. He can watch you using them on yourself, he can use them on you, or you can use them on him. As long as you remember proper maintenance and cleaning practices, you can share your toys like you’re in the first grade.

You’re naughty if . . .

• You never leave your house. If your favorite vibrator or dildo is holding you captive in your bed, then you’re abusing the toy privilege. There’s nothing wrong with getting off on your own, but you must go out for air and human interaction at least once a day.

• Your partner sex life suffers. If you prefer your toy to your boy and would rather get off alone, then you are just being a bad girl. While there’s certainly pleasure, not to mention efficiency, to come from your vibrator, it doesn’t hold you, whisper sweet nothings, or make you soup when you’re sick. Don’t neglect your partner for a battery-operated device.

• You use it to humiliate him. If you use the justifiable praise of the modern dildo or vibrator to make him feel inadequate, then that’s just mean. A man does not need to hear “my dildo doesn’t do that” when it comes to size, shape, hardness, or endurance. Well, unless you’re referring to something really spectacular.

With Christmas just around the corner, many out there are wondering whether they’ve been naughty or nice this year. Holly and Jason are tackling the issues that Santa just won’t touch, to give you a heads up on whether you should expect delightful presents under your tree or a lump of coal in your stocking.

Happy Endings: Holly Says

In nearly every neighborhood in San Francisco, you can find dimly lit massage parlors with names like “Moonlit Garden” and “Lotus Delight,” complete with a neon “open” sign and covered windows. They exude mystery and foreboding, unlike the tranquil, well-lit, high-priced spas that the city is also peppered with. It is hard to imagine that these seedy establishments can deliver a “happy ending,” but indeed they hold that promise.

As a woman, I’m sure the “Dragonfly Parlor” can’t service me as well as its male clientele. Further, I don’t understand the appeal. A romp with a prostitute in a dirty motel room seems more intimate than a handjob from an elderly Asian woman on a massage table. But perhaps it is the efficiency and sterility that makes the happy ending; it’s the like 7-11 of getting off. As far as I’m concerned, that’s why cell phones vibrate, but to each their own.

My gender-bias about the happy ending handjob aside, here’s how I think Santa would weigh in on the happy ending:

Happy endings are nice if . . .

• You’re single. If you’re a single dude getting an HJ at a parlor over your lunch break, it’s probably safer and less complicated than any other orgasmic experience with another person could be.

• It was a gift. If your woman is so kind and open-minded as to give the gift that keeps on stroking, then it sounds like you can have a happy ending and a happily ever after, too. Oh, and if your girlfriend or wife does get you a handjob as a gift, do pamper her with a trip to a day spa.

• You have an agreement. If you and your partner agree that a parlor is the best place to get a little extra stimulation on the side, then you don’t need Santa’s approval.

Happy endings are naughty if:

• You’re deceitful. Both Santa and your mother told you that lying is wrong. If your happy ending puts another’s happiness at risk because you’re being deceitful, that is just downright naughty. And not in a good way.

• You’re there when it’s raided. If you’re at a parlor when it’s raided, then you have a lot more to worry about than not getting presents this year.

• You don’t tip well. I support tipping well for any service, but certainly anything below the waist. I overtip my bikini waxer; you should overtip the first-generation immigrant who just wanked your weener.