Dear DW:
I need a bit of advice. My boyfriend (who is also the love of my life) has cum inside me only once in the 6 months that we have been having sex. We have sex a lot and always have tons of fun. And he will finish for me with the combo of his hand and my mouth.
When we are having sex, he gets really really close.  We’ve tried various positions, pillows, mini vibes, kegels, breath-holding, nipple stimulation, etc. I can tell that he’s getting a bit frustrated.  I’m not concerned for myself on this. I’m having plenty of orgasms and I’m on the pill.  But I want to help pull him over. Any helpful suggestions?
Hopefully,
Helpful Honey
Dear Helpful Honey,
I had a boyfriend like this once and no matter how much I assured him that my IUD was a really solid form of birth control, he still wouldn’t come inside of me because he was afraid of knocking me up. We were together for three years and he only came inside me like five or six times. While it was a little frustrating, eventually, I came to understand and appreciate his gesture. I didn’t want to have a baby with that joker either!
He doesn’t want to knock you up because he’s only been intimately acquainted with your vajay for six months. I don’t really think pressuring him or making this a big deal is particularly fair — you have been dating for a really short period of time. No amount of nipple stimulation (his or yours? heh) is going to remove this mind-block he’s got on buttering your bean.
I also think you have to think about where your man learned to have sex — a lot of younger guys base their sex lives on their porn library. MOST porns end in the manner in which you describe — a sloppy beej or hand-job complete with jizzle in your eyelashes. It’s rare that a dude fills up his lady’s parts in porn and if it happens, it’s because they’re catering to a particular fetish.
Honestly, I think you need to cool your jets. You’ve been dating for six months and you’re calling him the ‘love of your life’? Really? Contrary to popular belief, I’m really something of a romantic and even I think that’s a little much. It’s causing me to shrink up my shoulders and make a face — no telling what that kind of statement is doing to your dude’s wang.
Is it possible that he’s less frustrated with putting the custard in your doughnut and more frustrated with you hassling him about this? There’s probably more to this story so I feel like I can’t really give you a straight up answer.
If it’s an issue of his inability to find release, check in next week. I’m going to look that one square in the eye. This sounds more like a mental decision on his part and one that you should probably respect.
Love,
DW
