Doin’ It With Dr. V: The 28-Year-Old Virgin

This week, I got a letter from a lady who has an itch she’s been meaning to get scratched. She just can’t quite seem to reach it.

I have a dilemma and am looking for some advice. I’m 28 years old and still a virgin. It isn’t something that I planned, and I find it a bit embarrassing. I dated the same guy all through college, but at first I just wasn’t ready yet. Even once I personally was ready, I knew that having my first time be with him wasn’t probably the best idea. (We were complicated, angsty, and breaking up/getting back together all the time, and I felt like having sex with him would just complicate things further.) I dated a guy for quite a while after college whom I wanted to sleep with. We had great chemistry, and plus I was really ready by then. He told me he didn’t want to because he “didn’t want to be the jerk who took it from me,” and eventually he cheated on me. It took a little while to recover from that, and I didn’t even date for a while.

I have dated since then, but nothing serious enough to think about sex. Now I’ve just started seeing a guy that I kind of like. It’s still VERY new, but I know we’re going to have sex soon, and I’m not sure what to do. I don’t really want to tell him that it’s my first time, but I’m afraid he’ll figure it out. I should mention that I’ve done everything else, and have had an orgasm, but I’m afraid that I’ll be bad at sex and won’t know what to do. One of my girlfriends who knows about my situation thinks that I should tell him that it’s my first time, but I really don’t want to. I never meant for sex to be a big deal, am kind of wishing that I had just had sex at some point over the last several years with someone I wasn’t serious with, and I’m afraid if I tell him that he’ll turn it into a big deal (like my ex did). It’s not that I want to lie, and I realize that he should be OK with it if he really likes me, I just don’t see a reason to tell him (other than I might be really bad at it). Any thoughts?

Sounds like you’ve been holding onto a lot of things for too long — so frustrating, I know! Hot stuff, sex is about letting go, opening up. Getting down and dirty. Going all the way with someone, no holding back. And honey, if you can’t tell a man what you’re thinking, how are you going to be able to show him, naked? I’m with your gal pal, you gotta tell him, and here’s why.

From your letter, I get the sense that you just want to give your virginity to someone, like a present. How generous! Sure, there’s a chance you’ll freak him out if you tell him you’ve never done it. But then is a guy that is willing to run away that easily the kind of dude you wanna do? No way. I cannot let you go down like that! So, I’m so glad your ex showed his true colors before you got too deep.

All the emotional stuff aside, even if you lost your hymen horseback riding at summer camp or something, sex hurts the first time. He’s going to need to go slow. You’ve gotta give him a heads-up, no pun intended, before your first time is more painful than it needs to be. And you know, stained sheets will give you away anyhow. Honesty is the best policy.

Besides, the idea of a tight virginal vag is, like, every man’s fantasy. Start thinking of it as a plus, not a minus. You hold the cards, er, the V-card. Plus, if you’ve been lovin’ this long on oral sex alone, clearly, you’re giving in the sack. That’s what we’re all looking for. You big giver, now it’s your turn to get your sexual fantasy!

Honestly, if you’ve gotten the foreplay down and orgasmed, well then, sugar dumpling, you’ve made it! You’ve got more than enough experience under your belt to have sex. And frankly, to get the P in the V really requires no skills — you got the hard stuff out of the way first. Now, you just have to sink one in the hole. But I would wait to put sex on the table until you two have just straight-up hooked up. Then, once you get your kinks worked out and both know how to please each other, you can go the distance.

That being said, I want to warn you: Sex doesn’t keep a man. In fact, in my experience, it is not uncommon that after they get what they want, they don’t want it anymore — even if you screw like a hybrid of Dr. Ruth and Angelina Jolie. So, just be prepared. He might bail on you after sex. Or you might hit a bump and break up shortly there after. But then again, nothing in life is certain. We’ve all got to take it where we can get it. And, might I add, get it while the gettin’ is good. Seems like this new man has real cherry-poppin’ potential, if you want to give him the chance to get to know you!

Hi, I’m Dr. V. I’m not a real doctor; I just play one on the internet. What I am is a lady, a lady who is a fool for love! And I love nothing more than sex. My deepest desires have happily led me on many adventures in the sack, but they have also, sadly, made me one of my gyno’s most valuable players. But I’ve lived to tell the tale(s)! So, from time to time, I will dish the dirt on everything from getting freaky to getting freaked-out. And please, if you have a question, email me. You know I love to read your smut too!