Dear Di,
Trying to fuck my girlfriend lately hasn’t been working, and I need your help. I’m pretty hung like a Gee-Gee… Not so much in the length but in the thickness. I think the problem is that she’s too tight for me, which is why I can’t penetrate her deeply. When I get just the tip inside, she says she’s not sure she can handle much more. Do you have any suggestions? Would there be any positions that would facilitate the penetration or is it more of an arousal issue on my girl’s end?
—Big Dick that Can’t Get In
Dear BDCGI,
Your dick is not the size of a baby’s head, so it’s not too big to fit inside a vag. I’ll give it to you though, giving birth is not necessarily a comfortable experience; so yes, your girth might be causing some gargantuan issues in the sack.
There are definitely positions that can help you two out. Girl-on-top lets your lady control depth and speed of penetration. If she’s feeling stretched beyond her limits, she can ease off a little, keeping her thrusts as shallow as Paris Hilton. Missionary can work as well—just tell your woman to keep her legs together. That ups how much friction will be going on on her love button and also ensures you can’t plunge so far as to be painful.
That being said, I think you and your gal need to engage in some foreplay. If your girlfriend is afraid of the pesky pain that often comes with your pecker, nervous Nelly might be tensing up her down-there muscles and producing less below-the-belt juices than she might otherwise. Go down on the gal, play with her nips, tease her with your tongue. The more foreplay you have together, the more aroused your sweetie will be, and the more likely she’ll get soaked. The wetter she is, the easier it’ll be to slip your sugar’s v your p. Plus, invest in some lube.
Hope you enjoyed the opportunity to boast about your big dick, and that these tips ensure you’re not left jacking off into a loose sock.
Love,
Di
Dear Di,
I like short guys. I find myself so attracted to any guy under 5’2. If I see one in class or at work my panties just get really wet. I’m a 5’8 woman, but something about a tiny guy just gets my engines revving. I picture taking him to my place and having him fuck me silly in all sorts of ways. Plus, I think short men tend to be funnier. My problem, Di, is that short guys don’t seem to want me—occasionally I have one-night stands, but even those are rare and they never turn into anything meaningful. What can I do? Should I try to change my type?
—Short Expectations
Dear SE,
You have specific tastes—almost painfully specific. One thing that could be going on is that you’re secretly sabotaging yourself. By limiting yourself to individuals who meet very specific criteria—in your case, vertically challenged dudes—you’re possibly ruining your chances of having a relationship altogether. I’m no therapist though—I just really love sex. If you think you’ve got bigger issues going on, make an appointment with a real PhD!
On the other hand, some people are just attracted to a certain type. There’s not much advice I can give to you besides ‘hang in there.’ I can commiserate—plenty of men feel self-conscious walking down the street holding hands with a woman who towers over them, but don’t lose hope. Eventually, you’re bound to meet a short, funny guy who wants to date—and not just fuck—a taller woman such as yourself. I just can’t promise how long it’ll take for you to find him.
As for actively changing your type… If you thought that was an easy solution, you probably would have just decided to be attracted to guys of any height and wouldn’t have had to write in to me at all.
Don’t despair, though; you can broaden your tastes. It just might happen backwards from the way you expect. Rather than trying to change who you’re most attracted to and then dating them, just give someone you’re not necessarily super attracted to a chance. Date some non-petite dudes. I promise, there are guys of all heights who are hilarious, sweet, and want to bang you. Meeting someone interesting who doesn’t necessarily fit what you think you want, then having them charm the pants off you (literally, hopefully), might be just the thing you need.
Love,
Di
