We all say it's what we want, a guy who is well-endowed, but ladies, have you ever been with a guy who REALLY IS well-endowed? And I don’t just mean above-average here.

Have you been with a guy big enough where it may become a problem? Like a pain problem? If you haven’t been in that situation then be thankful, and if you have experienced it, I know you feel my pain…literally.

So Sports Guy and I have been dating for over two months now and things are great- he’s fun, cute, caring, and gives this Jewish princess all the attention she needs. He’s a great kisser, and we’re very attracted to each other, but no matter how much attraction there is in a relationship- it’s hard to fit a square peg into a round hole if you know what I mean.

Sports Guy is big. Like porn big. And I’m no porn star- just your average girl, who watches porn sometimes. When I first saw his ammo I thought, “Wow, Sports Guy!” not fearing for my nether regions in the slightest.

Then I did more than see it, I felt it inside me and I thought, “Ouch- that thing really hurts- but I’ll get used to it”.

And now over six weeks later I think, “OW this still really hurts. Are we sexually incompatible? Is it a deal-breaker? Can this be break-up worthy?”

It can’t be... right?

Once Sports Guy and I get that huge thing in me (after much foreplay, some deep yoga-ish breathing and intense concentration) it's good- better than good, but those first initial moments each time are what puts the buzzkill on the whole mission. It’s like flashbacking to my first time…everytime.

What a problem to have Jgirl, I know you must be saying- but think of it this way- all spontaneity is gone. I’ll never be able to just go and jump my boyfriend’s bones when I feel like it. Quickies in stairwells or backseats are out of the question. It has to be a whole production, complete with pausing for a hefty handful of lube, everytime. Or else it just literally won’t happen.

I even bought the fancy $22 lube thinking it would be magic. No such luck. It’s the same as any other lube, just in a fancy package. It’s been a problem for Sports Guy in the past and his answer is just more lube, more foreplay, more lube and more lube. It’s getting pretty messy round here as you can imagine.

So what’s this Jgirl to do? Squats? Yoga? Deep meditation? Can this really be it? I don't want to let this one go over something so little...I mean big...

Oy Vey.

Photo by Kriegerinhummel via Flickr