Dater X: O, Baby

Over a month deep (giggity) with The Big Easy, we’re getting the hang of this “pleasuring each other” thing.

With a shoutout to my girl Miranda Hobbs – who reminded Carrie “Work of Fiction” Bradshaw, after a disappointing first encounter with Berger, that if she’s never had to “work on it” with someone she really liked, she should keep that to herself – we’re working on it. For one thing, getting me to climax is no small feat.  Well, that’s not exactly correct.  It’s a very small feat. Best accomplished by me. In the privacy of my own bedroom. With, ahem, the judgement- (and preference-) free aid of a certain pillow and no fewer than 10 minutes of quiet alone time.  Sure, I’ve fiddled around down there over the years to see if there might be a more partner-centric way to fire one off – read: fingers, a shower head, “marital aids” – but no dice.  And since I’ve never had any problem managing it myself, I figured when the right partner came along, so would my orgasm.

Try not to laugh.

And how have I dealt with this in bed before? I’ve faked it, frequently and with enthusiasm. The truth is that I really don’t have any problem with not reaching orgasm via intercourse, especially when I’ve become so efficient at getting myself there and especially when there’s also my partner’s pleasure to enjoy.  Sex can feel good without a climax. Yadda-yadda-yadda.

The thing is, I now find myself in a committed relationship with someone that’s looking more and more like the person I might be intimate with for the rest of my life, meaning that I have no interest in faking it, which would be tantamount to lying to him. And he’s as interested as I am (perhaps even more so) in making sure that I get there. The problem for me is that I know that. Nothing stops me deader in my tracks than someone asking me about how things below the belt are coming along.  As soon as I have to think about it, it’s “Game off! Get the net out of the street! Car!” in a scene that would make Wayne and Garth proud.

Pretty great, right?  I know what I like, but it’s difficult to accomplish with a partner, and I can’t stand to be asked about it during the act. Piece of cake!

…is now the right time to mention that while a couple of guys, notably the lead singer with the elastic hips and the wildly attractive investment banker who slummed it with me one summer, have come close, I’ve never gotten there with a partner?  Ever?

The Big Easy has been both patient and creative. We’ve been experimenting with different positions; I’ve been working on using my words like a big girl and telling him what seems to be working and what doesn’t.  For one thing, I’ve never really taken the opportunity to “work on it” with a steady partner before. Mostly because there haven’t been that many, and those that have stuck around for more than a couple of sack sessions were either spread out over several years of ongoing flings or my last committed relationship, nigh on a decade ago and a decade my senior, with whom I was frequently so intoxicated by the time we got to bed that neither of us gave much thought to the other’s satisfaction. I know: how romantic!

Young Dater X was kind of immodest with her choices. And now the Dater X of Today is stuck with a lifetime’s worth of great (fake) performances and little experience actually cresting the hill during intercourse. The Big Easy, on the other hand, is getting there with perhaps even a bit too much enthusiasm. Since this has all been horribly embarrassing to write about, why stop now? Story time!

Once upon a time, there was a girl named Dater X. Dater X held the unshakeable belief that Blowjobs Are For Boyfriends.  And while she relished giving them to the men she really cared about, she left them off the menu for flings and fuck buddies.  Seven years out from her last relationship, she was pretty sure she still knew how to get the “job” done, but it had been quite some time.

One day, Dater X met a guy named The Big Easy.  He fell for her the moment he met her, and hasn’t stopped; it took her a little longer to get out of her own chronically single-girl way, but she managed to see what was in front of her and cast it in with The Big Easy for the long haul. The Big Easy revealed that, like so many warm-blooded American males, he digs a BJ. Dater X prepared to come out of retirement, apprehensive but excited about the idea of doing something nice for the person who opens her cab doors and rubs her shoulders after softball and makes light of the hives (HIVES!) that her beloved pet gives him when he spends the night at her apartment.

So one night not too long ago, Dater X climbed into position astride The Big Easy and made her way downtown.  The Big Easy saluted her descent with fervor. She put to use the tricks up her sleeve, including an old favorite gleaned from her far more experienced college roommate involving enough saliva to make the inside of one’s hand feel like an extension of one’s mouth (Ed: Ladies, if you’re not doing this, trust me: start drooling.  A hands-free BJ really is a job.) The Big Easy twitched and gasped and finally achieved what Dater X has yet to accomplish in bed, coming hard in her mouth and thrusting at the same time. And Dater X gagged audibly, and then he just … kept … coming.  And some of it came out her nose.

Many good Kleenex were lost in the minutes that followed as Dater X and The Big Easy laughed at their bodies in a comfortable way that would have been unimaginable with a fling.  And while she still sneezes a little harder to this very day, Dater X was gratified to realize that A) she’s still got it and B) if she can handle the money shot coming out her nose, surely learning how to ask for what gets her off during intercourse can’t be far behind.

Want to contact Dater X directly? Email her at [email protected]!